Group Coaching Questions

Following are questions that have been answered in Ditcherville (i.e., my group coaching community):

Is strategic advising a valuable differentiator for a developer?
I currently sell my time hourly as a Rails developer (and before that as a Mac IT guy). I’m trying to find what I do differently from other devs, and I’ve noticed I often end up strategizing for/advising clients. For example, one client has a frustratingly broken dev process, so I’ve been talking to everyone from the junior dev to the CEO to understand the landscape and determine the cause, and coaching the lead in our weekly one-on-ones into fixing it, without (so far) stepping on anyone’s toes. (He jokingly says the sessions feel like therapy.) Or another client who often asks me for my “strategy brain,” rather than my “dev brain,” even specifically reaching out during a period where I wasn’t doing dev work for them. I think the skill is something like “listening, asking the right questions, synthesizing, and getting to the heart of complex situations”. But I’m not sure how to position that. Businesses who “know” they need websites don’t even usually know they need untangling. Is this even a differentiator? I think it’s more than just “being good at the Why Questions”? I guess my question ultimately is: is this idea worth being part of my positioning, or is it/should it be just part of delivering good results? (timestamp: 4m23s)

What’s your favorite use for ChatGPT currently?
After reading your daily email “Next Big Thing” I am officially a convert to ChatGPT. What do you love using it for right now? (timestamp: 16m40s)

How can I improve my coaching retainer options?
I’ve started a couple monthly retainers for advising/coaching. I give 3 options in the proposal: 1) one zoom call and unlimited emails with response time 4 days, 2) 2 zoom calls unl emails response time 3 days 3) 3 zoom calls unl emails response 2 days. I’m trying to think of better options to offer to encourage the middle option without including only my time as differentiator. There’s no real “deliverable” - just pure coaching/advising. Are there better ways to create the options here? (timestamp: 25m41s)

Should I focus on Google Ads Scripts or broaden my offerings?
I am a Google Ads consultant, specializing in Google Ads Scripts. I have a mailing list of ~5k Google Ads professionals interested in Google Ads Scripts. I’ve been selling scripts and scripting knowledge at small scale. Now I am considering creating an online course and a paid community around Google Ads Scripts, but not sure if this topic will still be popular 3 years from now. Should I go all in on this topic, or go for a broader positioning? (timestamp: 34m1s)

How can I price an MVP for a potential SaaS solution?
I do have a client who is looking to build a custom tailored solution for their own business. They want to build an MVP first, adding new features and improvements later. It seems that eventually they want to sell that as SaaS for their clients (there is no business plan for that just yet). So my question is how would you discover the value of such projects? Otherwise it seems not possible to fix price that. (timestamp: 39m11s)

How did you gain early authority in the mobile space?
Your initial path into the authority space was via mobile, and it seems you caught an early wind when change was afoot in that space. What did you do that enabled you to get out ahead that others didn’t do? Asking under the influence of watching all the movement in AI these days. (timestamp: 48m14s)

How to transition from technical work to consulting quicker?
My current path to consulting with clients typically starts with technical hands work, and then when I’ve build context through the hands work, bringing along the ability to do proper consulting. How best can I/someone shorten that pipeline (and not lock in on doing hands work) and still get sufficient context to give helpful advice and ask good questions? (timestamp: 57m17s)

What are some signs that you need more authority in your space?
I’ve previously heard (potentially from yourself even) that people buy from those who they know, like, and trust. I’m not 100% sure which of these I’m lacking, but I feel like I lack the authority that some of my competitors appear to have. For example, I often get positive feedback from social media DMs and from my email list, but I don’t feel like I get enough interest in my products/services. (timestamp: 2m54s)

What’s the easiest way to pick a niche that will bring in good side money quickly?
To make ends meet, I want to niche down into something I’m good at with a market that has a need. Think “Websites for Therapists.” But, there’s already someone doing this exact thing (different business model though). Should I pick something else? I can’t be the ’one and only’ if there’s two of us, can I? (timestamp: 13m3s)

What are reasonable expectations when building a new audience from scratch?
I’ve been building an audience for just over a year, I’ve almost cracked 1,000 social media followers, and 100 people on my email list, but is this slow? I’m doing this alongside my main source of income working for completely random clients, with my time split being approx. 70% on client work and 30% on audience building. But I’m nowhere near being able to replace my main source of income. (timestamp: 27m31s)

How do you know if you need to get better at marketing and sales?
The dev/engineer mindset and the marketing/sales market are so different that it feels hard to switch from one hat to the other. What can be the AHA moment that could lead fellow developers to realize that they need to learn more about marketing and sales? (timestamp: 34m34s)

Do you know any ways besides a mailing list to own your audience?
I ask because I want to reap the benefits of a mailing list, but my ideal buyer despises mailing lists. Maybe they’re bluffing and maybe people from all positions say this, but I’ve heard a couple of my clients specifically say, “I’ll never sign up for a newsletter.” (timestamp: 39m32s)

Are paid 1-on-1 coaching calls more of a funnel to more expensive services, or are they a revenue stream unto themselves?
Do you consider the 1-on-1 consultation calls as a funnel to retainers or as a product in itself mostly? Has this changed over time for you? Under what circumstances would you focus more or less on 1-on-1 calls as a funnel to retainers? (timestamp: 47m26s)

How should I experiment with positioning as I get back into full-time freelancing?
I am a generalist (full-stack web dev, IoT, Smart TVs) because of my current work (previously a whale client) but I want to move back into full-time freelance. My plan is to start with implementation in any of the fields and then try advisory once I better understand specialization and chosen niche. What would be a high level path to that? a)Try one specialization after another for appropriate niches b) Try to spawn multiple separate offerings in each specialization for different niches? (timestamp: 54m49s)

How do I break through an income plateau?
I feel like I’ve hit a bit of a plateau with my JavaScript Education business, and I’m not really sure where to go from here. (timestamp: 68m15s)

How do your positioning and the sun in your “content solar system” relate to each other?
Could you share how your “positioning” could be, and maybe should be, different than your “sun”? (timestamp: 80m3s)

What’s a good way to do cold outreach to “big time” CEOs?
I was inspired by your BoA “Cold Outreach” podcast. I niched down to be more specific (Brand strategy for CEOs of companies on path to going public) and I love Rochelle’s idea that cold outreach can be simply “warming a prospect to be less cold.” But I’m stuck on HOW to warm a cold prospect, when this audience has such time/attention scarcity. When I targeted lower level people, I’d ask them for coffee, but CEOs are resistant to that. Ideas for cold outreach that doesn’t turn off bigtime CEOs? (timestamp: 85m34s)

How should I structure an ongoing client relationship after our initial project winds down?
I’m winding down my first big client engagement and they want to continue working. Since they tend to have a lot of projects they need help with, I’m thinking of a more open-ended fractional role. How would you think about structuring that with tiered options so it doesn’t overwhelm someone? Another ditcher uses a monthly retainer with: 1 - Advisory only 2 - Oversight for a critical project or initiative OR coaching 3 - I take full ownership and responsibility for an area of their business (timestamp: 94m15s)

Do you have a framework or process that helps identity and prioritize optimal niches and offerings? (timestamp: 100m11s)

What should I do if my ideal buyers are engaging with me on LinkedIn but aren’t subscribing to my mailing list?
I get my ideal buyers engaging with my daily writings on LinkedIn but I have very few, if any, join my daily mailing list. Would you keep publishing to the daily mailing list or consider making changes to the frequency or even killing it and just posting to social? It’s been a good three years that I’ve had my list but I’ve just been posting daily for the past one year. My list is filled mostly with peers instead of my ideal buyer. (timestamp: 4m0s)

How can I test whether my chosen niche is too small?
If you suspected you were too niched or narrowly focused, how would you test it? (timestamp: 8m48s)

How can I speed up my subscriber growth?
My daily email and podcast are growing — but slowly. I’d love to accelerate my list growth for both, and get the benefits of a bigger list sooner. What are some ways I could do that? LinkedIn ads? Direct invitations? (P.S. - I’d love to avoid approaches like answer-bombing and webinars, because those require generating even more content.) (timestamp: 16m52s)

Should I niche down even more?
I’m a Squarespace 1 day website designer. I’ve narrowed my target market to expat business owners in Germany. However this can be anyone from a trailing spouse starting an Etsy shop to an established expat running a multi-7 figure business consulting automotive companies. It makes messaging and crafting offers difficult. Do I need to niche further? For example by industry or business size/maturity or both? (timestamp: 34m1s)

How fast should my list be growing?
What is a normal list growth percentage and speed to expect for an authority business? E.g. “Expect 1% growth per week, so a list of 100 would be 101 after a week, and a list of 10,000 would be 10,100 after a week.” Or, what was your growth like? (Bonus: same question for podcasts.) :) (timestamp: 44m38s)

What are my options for pricing follow-on implementation work?
I Started consulting and PS to a company last November. Leads have been dry and now need to move client to some sort of retainer, where do I even start in terms of offering and pricing without looking at hour/month? We go Live in 2 weeks and have a roadmap which I could include as project (which might open up for Proposal with competitors) or try to fit into a retainer (for a much needed monthly income) (timestamp: 50m28s)

How can I validate a new positioning statement?
When you’re researching a possible new position, what criteria do you use to determine that it is promising enough to change your website/LinkedIn? (timestamp: 62m31s)

How can I tell if a new opportunity is actually a distraction?
A “watering hole” / community forum where I learn about my target audience is looking to grow. Possibly with help from a software developer, possibly by taking on sponsorship. How would you evaluate this as a potential opportunity to get more involved with this community, versus a distraction from helping or learning from the people within it? Thanks! (timestamp: 66m0s)

How much should I spend to have shorts created from my long-form videos?
I started my Big Idea SketchCast project. So far I have sketch-interviewed three people. It is fun, and I’ll try to get more famous interviewees in the future. I think I need to do a sped-up 3-5 minute version of the video. (Or what?) This is a lot of work. But I found an editor who does a great job for 230$, How do I best leverage this, to get the most out of my investment? Or, should I find a cheaper editor? (timestamp: 67m43s)

Is selling IT services door-to-door a good idea?
Dealing with busy decision-makers makes it hard to get their attention over emails, etc. So, I’m wondering if there are any tactics you can recommend for selling IT services door-to-door, and whether it’s a good idea at all. Let’s say you’ve done your research having a list of companies with decision-maker details. How would you execute the door-to-door message delivery and does it make sense to try to approach mid-big size companies that way? (timestamp: 3m36s)

How do I convince prospects that my service is valuable BEFORE they experience it?
Had feedback call with a beta tester for my productized service. The biggest takeaway from my client (seed stage startup Founder) is that they in retrospect could easily say the service was worth money to them. At the same time, their point, which was well taken, was that it would have been hard for them to know the extent of the value upfront. My service is a 90-min design clinic where I help the CTO/lead engineer optimize their designs, saving their team months of time on development. (timestamp: 14m23s)

How do you go from ‘zero to one’ in terms of a mailing list?
If I have no or a very low number (less than 25 let’s say) of subscribers sending out emails seems like I’m talking to no-one. How do I get that initial set of subscribers to make sending emails “feel useful”? Something like a blog feels like it would be a better starting point? (timestamp: 23m45s)

How do I explain the value of API integrations in business terms?
I’ve had a couple of clients that paid me for a custom database combining info from an in house database and an external CRM with their clients. One was in Real Estate with leads on a separate “Real Estate leads” website, another was in corporate education with courses hosted on a separate “course hosting” website. How do I explain this offering in business terms? (timestamp: 30m52s)

What should people think about before starting an online community?
Would you be able to talk a bit about when you first decided to make your coaching group? What drove you to do this, what were your concerns, etc.? I have rough plans to start a community for my audience, after I get a few other things out of the way as well as verify it’s something that will be valuable for them. So I’m curious to hear the journey you’ve been on with it. Thanks! (timestamp: 42m14s)

What’s the best way to structure an email course?
I have a video course launching soon and I want to create a mini email version of it as a lead magnet. I currently have five emails drafted and each is around 500-700 words or so. The content of these is derived from the first module of my course, and the final email includes a link to the course’s sales page. Does this sound right, or what would you recommend? Thanks! (timestamp: 56m10s)

Is it okay to write about tactics when what I really want to sell is strategy?
I find it much easier to write about technical (but still relevant) topics for my email list, instead of strategic ones, but I want to focus less on “hands work.” What are some good ways to stay on higher-level topics? (timestamp: 59m54s)

How/when do you deem an audience too hard to reach?
(timestamp: 1m24s)

How and when do you prune your email list?
Do you prune your (daily) email list? How do you decide when it is time to do so? And how do you do it? (timestamp: 5m53s)

Do you recommend diversifying by holding multiple, very different jobs?
Or do you think that is too much of a distraction? For example, being a business owner and holding a mainstream job (such as being a realtor) at the same time. (timestamp: 9m37s)

Would you let competitors into your private community?
Would you let your competitors / similar service providers into the online community you’ve created? (timestamp: 13m54s)

As I move toward more advisory engagements, how do I support my clients who still need implementation?
My background is primarily doing hands on. As I try to raise my level of engagement how can I help my customers still get the hands on work they need completed? Any suggestions or resources on sourcing development team, helping them skill up, etc? (timestamp: 15m11s)

How can I revive a deal where the prospect ghosted me after seeing the price?
I shifted to meet w midsize biz (away from F500) where my services would be of more help (maybe more value). However, I’m struggling on price. I had 1 decent why conv & it seems there is value, they asked for pricing & I pushed my assess project & then they went dark on me. Guessing pricing was too high or they didn’t see the value (which I never saw with F500). I want the project, interesting/potential future opps. How would you save this lead/should I save it? Should I drop assessment pricing? (timestamp: 19m19s)

What kind of questions should I be asking during the initial market research stage?
Can you talk a bit about initial market research and the key questions to determine what your ideal customers need? If you are wanting information about what they would purchase in a service format versus productized service versus product and/or some combination do you get at this in your initial market research? Or do this later or in some other way? Thank you! (timestamp: 27m50s)

How do you measure customer satisfaction during an engagement?
I’ve heard you say you hope people are measuring customer satisfaction, as opposed to certain other metrics. Can you talk more about this? What are some ongoing ways to do this, beyond your testimonial approach at the end of a project? Thank you! (timestamp: 34m29s)

How can I generate a prospecting list?
What would be the best approach to generating a solid email list / cold call list for productized consulting services? (timestamp: 41m41s)

How would you approach getting guest blog writing to get backlinks?
(timestamp: 48m36s)

What’s your advice for how to launch a video course?
And would you offer future access for free? I should hopefully be finished with my video course within a month or two, but I’m not 100% sure how to launch it (e.g., should I have some kind of introductory offer?). Also, would you suggest offering future access for free? Or only access to that iteration of the course? As I’ll be updating it over time. Thanks! (timestamp: 1m25s)

When is it a good idea to broaden your niche?
I currently work with wedding celebrants/officiants but the primary problem that I help them with (getting new clients) is also a concern for other wedding suppliers (e.g. photographers/videographers). These other suppliers also have potentially higher buying power. Would it be a good idea to broaden my niche from celebrants/officiants to wedding suppliers instead? (timestamp: 12m9s)

How should I grow my podcast audience?
What are the top 2 or 3 activities you'd suggest to grow a podcast audience? This is an interview style podcast in which I talk to the technical leader of a startup in my niche each week. I've been publishing episodes weekly for almost 6 months now, with an average of 75 downloads per episode. The audience is growing, but much slower than I expected and much slower than my newsletter grew when I started it 2 years ago. Any advice? (timestamp: 19m22s)

How do you balance being tactical vs. strategic while building an audience for a daily list?
Especially if you don't think of yourself as a “thought leader” (I resonate more with “curious learner.”) For example, I find it easy and quick to write tactical tips but also know I need to be refining my thinking (which takes much longer). People seem to like “actionable tips.” (timestamp: 28m46s)

How can I get “big” guests for my video podcast?
I need a proper media channel. Because what I do is visual, a YouTube channel is better than podcast. My idea is to interview “celebrities” and draw their big idea. Something like “The Big Idea Sketchcast.” Ideally, this should be people with an audience, and interesting for my ideal client (software CEO) - and for me. One possible topic is AI. Do you have ideas about who I could approach for those skech-interviews, and how? (timestamp: 34m46s)

How do I test for demand in a market?
In reference to your TBOA episode “Why Your Stuff Isn’t Selling”, where can one learn more about this idea of an “active” market with existing buyers and sellers vs a specific segment of the population? I have been working on a specific niche for the past 4.5mo and I have some concerns that there isn’t a “known” market or any demand. You mentioned doing something to quickly test out your market, the demand, and one’s appetite for delivering the solution. My question is how? (timestamp: 2m8s)

Should I include estimated timelines in my proposal?
In my proposal, should I tell an expected completion (e.g. 2-3 months) under each option? If not, what if the client explicitly asks “how long will this take”? (timestamp: 16m10s)

Should I enforce a minimum level of engagement?
I recently re-read the Win Without Pitching Manifesto, and it made me curious to hear your thoughts on minimum levels of engagements and what situations (if any) you’d recommend this kind of approach :) Thanks <3 (timestamp: 19m14s)

How should I price productized services?
How can one determine a price for simple productized services, such as a 1-hour strategy call? When would a call cost $1K+ vs. $500, vs. $200? What factors should one consider to decide whether to put a higher or a lower price? Thanks! (timestamp: 23m36s)

When might taking a day job to support my business make sense?
My income from my business is about 1/3 of what I was making when I was working as an employee, and I’m considering going back to working as an employee and doing my business on the side. What thoughts do you have about me managing both paths while trying to move back to having my business only? I’ve had my business for 8 months. (timestamp: 29m45s)

When a client asks me for work that is outside my expertise, should I refer it out or hire a contractor?
Should I create a productized service or formalize a referral arrangement? I have had a few people ask me if I can help them with SEO. I’m semi-experienced in this, so I thought I could offer it as a productized service delivered by a contractor that I oversee. Another option I’m considering is to refer people to a specialist in my niche, but I’d want to get a cut of that somehow. What would you suggest here? (timestamp: 36m33s)

How should I add webinar registrants to my mailing list?
If you were to host a webinar with a business goal of growing your mailing list (and ultimately generating leads), would you automatically add the webinar registrants to your mailing list or give them the choice to opt-in? (timestamp: 39m27s)

Would offering a productized service be a good way to compete with big agencies?
Any suggestions on productized services for technical content marketing that competes with agencies? My client loves the content I make, but I am not sure how to avoid looking like a pair of hands. I was considering a tiered done-for-you service that packages what the technical CEO liked most from my engagement: open source third-party integration with video and write-up. 2nd option adds a sample app showcasing the integration. 3rd option is to build a video/hands-on course around that app. (timestamp: 44m58s)

How could I increase engagement in a community of busy executives?
My ideal buyers are extremely busy which has made engagement, in my newly formed online community for them, a challenge. The members have each expressed genuine interest and excitement for the community, but are so busy they don’t participate. What are your ideas on how you’d design a community for busy folks? (timestamp: 60m40s)

How will I know when it’s okay to quit my day job and go full time on my solo consultancy?
At what point would you recommend quitting a day job to go from part-time to full-time with a one-person consultancy? What general indicators should one consider to ensure a smooth transition? (timestamp: 66m29s)

How should I handle social media if I sell two different things to two different audiences?
My ideal clients for my 1:1 service (executives) are on Linkedin, so that’s where I’m currently active. They are not interested in my courses. The people who buy my courses are (also) on Instagram and Facebook. Would it make sense to split my marketing, giving tips about drawing on Insta, and talk about messaging on Linkedin? Or is it better to be the same everywhere? (timestamp: 71m24s)

How could I test which types of media I’m best at?
The usual advice is: publish in the medium you’re best in. If you’re good on video, do videos. If you’d rather do audio, do that. But how do we know whether customers like our voice, or our style of writing, or how we feel on video? Can you suggest some ways to test that? (This is a question about charisma, not content.) (timestamp: 75m7s)

How could I improve my positioning statement?
Is “Mobile & web developer for Tech startups” a good AB positioning statement? I’ll work on the XY statement as I become comfortable with it. (timestamp: 80m9s)

What is the one thing I should be doing to get more leads?
Looking around I realize I have many plates in the air all aimed at helping me accomplish my goal of generating more leads and, in turn, doing more business. If you could pick the ONE most beneficial thing I could prioritize to accomplish my goal, what would it be? (timestamp: 1m53s)

Why is my mailing list not growing?
In your Pigeonhole Yourself talk, you mentioned getting 100 leads/week. After 6 months of daily posts, cross-posting to Twitter/LI in different ways, networking within my target market (B2B software marketers), and trying different positioning angles, I have no inbound leads to show for it and mailing list is stuck at 20 subs. My client engagement is going well but I don’t think I can get a Perfect Testimonial yet. Where would you start with debugging this? Doing a webinar next week! (timestamp: 8m39s)

How do I sell more strategy engagements when it seems like the demand is for implementation?
I am a former small nonprofit Executive Director with expertise in Program/Project mgmt. roles. In the Altitude of Involvement, I am mostly at the Implementation level in Operations and Program Delivery (step in as a co-ED with a new ED; project mgmt.), and am at the Strategy level in Leadership/Strategy. Q: How should I factor in urgency in my client base for implementation (e.g. turnover of key staff/willing to pay $$$$) and saturation of others doing strategy in my business strategy? (timestamp: 21m16s)

How do I justify up-front payment terms when there’s a 6-digit option 3?
Clients will never agree to that. (timestamp: 31m0s)

What advice would you give to someone creating their very first video course?
I went through TPS last year and I found it invaluable. Your teaching style is something I aim to emulate with my first course. What advice, resources, tips/tricks do you have to pass on? Thanks! (timestamp: 40m27s)

What are the pros and cons of a daily vs weekly newsletter?
My weekly content schedule is 3x LinkedIn Posts + 1x Newsletter. Question #1 — what are the con’s of this approach vs. daily email? Question #2: My concern is that I’ll have to lower the quality of content to keep up this pace. Is that a valid concern? Any tips on how to hedge? (timestamp: 53m50s)

Should I promote my daily newsletter above all other services I currently offer?
On my social media profiles, I link to a landing page that has the newsletter sign-up, a link to my YouTube page, a few productized services, and a waiting list for a new service. I promote all of these other things in my newsletter footer anyway, so would you suggest directing prospects to my newsletter only, so as to not overwhelm people? Thanks! (timestamp: 1m15s)

How should introduce a new email list to subscribers who have purchased my training products?
I have a list of around 4500 people from sales on Gumroad. Up until now I’ve only sent occasional product announcements (4 - 5 times a year). I’m finally ready to start daily. Any advice on how to introduce that to the existing list? Just opt everyone in and give them an easy way to go weekly or announcement-only? Or should I start an entirely new list? The topic is still the same: mastering Laravel - moving from competent to confident. (timestamp: 9m35s)

Should I meet with prospective clients who are interested in my productized service?
Do you recommend having the value conversation with clients interested in productized services? After TPS9, I created a productized service that I’ve sold a handful of times. I opt to have a meeting before people can buy it, as I like to double-check that it’s exactly what they need. Recently though, I’ve had a few calls result in the potential buyer walking away, even after it sounds on the call like they need it. This is why I now wonder if I should be structuring these calls differently. (timestamp: 9m49s)

What are the pros and cons of selling to two different audiences?
There’s a particular type of project that we’ve done many times in the past and we are good at and enjoy. I am wondering if it would be a good service for us to package up and offer, but it’s buyer (product development manager) is slightly different from our ideal buyer (innovation manager). I’m curious to hear your thoughts on offering a service that requires marketing to a different audience. (timestamp: 14m22s)

What should I promote in a targeted ad?
I’m considering purchasing a paid editorial style advertisement on a site that focuses on expats in Germany. My target audience is expat solopreneurs/entrepreneurs in Germany. Should the ad link to my lead magnet (30 great resources for starting, running and growing your business in Germany) OR directly to my services page (website design packages ranging from 1200-6k). Thanks! (timestamp: 19m22s)

How do I figure out how to describe what I do?
I think I’ve finally uncovered what value I’m adding for my client. They are based outside the US and they like that I have enterprise experience and can help them increase trust/confidence with Fortune 500s and speak to those developer audiences. So an XYPS might be, I help tech companies outside the US win over Fortune 500s. But I don’t know what discipline this might be. Sales enablement? Growth consulting? Fortune 500 Closer? Ideas welcome. :-) (timestamp: 23m24s)

How do I start shipping better products faster?
Jonathan - since you launched your product business, you have been prolific in shipping products and services. Does this ability come naturally? Do you believe it can be learned? (timestamp: 33m35s)

Should I post my daily emails on social media as is?
I’m writing daily emails but am hesitant to post them on LinkedIn because it feels spammy without a custom spiel, especially when there are no other posts coming from the same account (automated posts only). Adding a custom spiel to each post significantly adds time to the process. What’s your POV? (timestamp: 37m12s)

Should I refuse project offers that come through agencies?
I’ve received an opportunity but I don’t own the relationship, but instead reached out through an agency as a subcontractor. I don’t have a way to assess value. Should I turn down the offer or instead stick to the hourly x 1.8 pricing model? (timestamp: 40m47s)

How are you liking ConvertKit so far?
I’m considering switching to ConvertKit. How is it so far? Anything you miss about the old setup? Anything great about the new setup? Any little disappointments? (timestamp: 44m52s)

How do I stop clients from asking for “hands-on” work in an advisory only engagement?
When a proposal includes a “Just Advising” option and an “Advising+Doing”, how to make is clear that one includes doing work and one is just answering questions? (timestamp: 50m15s)

How should I get started as a soloist?
I’m a marketing-minded generalist designer who is rebooting his professional life as a solo practitioner. The good (and bad) news is that my career is a blank slate. Problem is, I’m trying to tune several dials at once: my expertise, my positioning, and moving toward strategy rather than implementation. I’m an inch deep and a mile wide. How can I move forward to find the optimal mix for me? Thank you! (timestamp: 54m8s)

What’s a good CTA to use on a webinar if I’m trying to sell five-figure service engagements?
What are the best ways to present an offer at the end of a free training webinar for 5k to 10k Done-For-You service? Every article or book I’ve read on this topic focuses on info products or education. And what are some Dos and Don’ts? Cheers (timestamp: 63m53s)

How many services should I offer when starting out?
Is it better to start out with a range of services or just one service? (ways you can help your ideal buyer solve their problem) (timestamp: 69m2s)

How could I improve my positioning statement?
How would you rate my positioning? I help midsize manufacturers generate new revenue with AI and machine learning services. (timestamp: 74m19s)

How many lead magnets should I have?
My plan is to generate 1 main lead magnet: A 30-minute presentation “Generating Revenue w/ Data-Driven Products in MFG and Industry” and funnel all traffic there. This would be the main thing. Would you pushback on this tactic? (timestamp: 79m35s)

Under what circumstances should I consider changing the name of my business?
I’m getting ready to launch my new website and through the process of doing it I’m realizing I might be now be a consultant. How do I know if I’m ready to change the name of my company from what it is now to First Name Last Name Consulting. Also, I have a daily email and I’d have to change the “from” line too. (timestamp: 81m35s)

Is YouTube a suitable replacement for a mailing list?
If you are posting videos 6 days/week on YouTube, is it necessary to also have a mailing list? (timestamp: 86m44s)

What are the pros and cons of taking on implementation work?
A potential client wants to engage and hire me as a freelance CTO, but this involves taking responsibility. I offered them consulting instead but they’re not sure if they should take it. How should I proceed? Will this hinder building my business? (timestamp: 92m5s)

Should my audience’s ‘biggest’ problem be my entry-level productized service? If so, what type of solution should I aim for (e.g. email course)? I DM’d Instagram followers over 6 months asking the ‘biggest challenge’ question, and “finding new clients” was the winner. Raising awareness and managing clients was the second and third answers. I have a productized service targeting the third problem, but I don’t sell it that much, which is why I wonder if I need a cheaper option to act as a gateway. (timestamp: 2m26s)

What’s the equivalent to advisory retainers if you target soloists with lower budgets? Would it be a paid group like Ditcherville, these calls, or are there other options to consider? Thanks! (timestamp: 14m33s)

How do I prevent my new online community from becoming a ghost town? I am creating a watering hole community for my ideal buyer. Do you have any advice from your experience on how to keep them engaged and repeatedly coming back to participate? All the other communities I’ve bench-marked are GHOST TOWNS which I desperately want to avoid. (timestamp: 28m29s)

How can I validate that my central theme resonates with my ideal buyer? I am working on defining my “sun.” I’m leaning towards something like, “Innovation doesn’t have to be so risky!” since my ideal buyer’s job-to-be-done is to determine what products their company should create next and what we do is visualize their product ideas for concept testing. My question to you is, how would you go about testing/confirming that this “sun” resonates with my ideal buyer? (timestamp: 40m41s)

How do you know if a business model is broken? Particularly, I’m doing CRM implementations- and it seems like the whole field is pretty much a single meaningful interactions (Setting up the CRM for the first time), followed by a series of transactional interactions (creating a report, making a modification etc), which eventually drive you down the hourly path. Am I missing something? (timestamp: 49m10s)

What methods are best for growing a mailing list? Is podcasting—whether your own or appearing as a guest on others—your preferred way of growing an email list? In any case, can you recommend other methods you’ve found useful? (timestamp: 61m37s)

How do you deal with stress? (timestamp: 69m43s)

How should I stay top-of-mind with prospects I’ve spoken with but aren’t ready to buy? What are good ways to stay in touch with promising potential clients who reach out to me, but where a project doesn’t come together this time around (ex. I’m unavailable in their timeline). Suggesting they join my email list seems a little pushy, but I’d also like to think of me in the future. Thanks! (timestamp: 74m41s)

What are the most effective ways to generate leads with my writing? If you were not able to write daily, what is the next-best lead generation method you would rely on? What would be the next-best method involving writing be (weekly email, book, etc.)? (timestamp: 81m33s)

How do you determine which of your older daily emails are worth re-sending? Occasionally, you send out daily emails that are repeats of past classics (and they’re great). How do you determine which ones were strong enough to resend? (timestamp: 92m18s)

How do I get over my loner/social anxiety nature and get good at hosting a sales call? (timestamp: 99m34s)

How can I now offer a 3 tiered proposal when they already know exactly what they need? Someone is reaching out to me for implementation, after already having a roadmap in place. How can I now offer a 3 tiered proposal when they already know exactly what they need? (timestamp: 109m40s)

Using the testimonial template from for my new website, should I publish their answers verbatim? I’d obviously want a review-like format. (timestamp: 1m32s)

How do I write a proposal for the 2nd phase of a multi-phase project? Do I have the sales pitch and why conversation all over again? Say, they chose option 3, should the follow-up proposal only include a single “Done For You” option or still offer 3 options? (timestamp: 6m13s)

How should I price my first retainer? I’ve been working with a client for 12 months and she’s keen to work with me. I’ll be mainly providing strategic advice, attending client meetings, leading design workshops, technical advice and a little implementation (although I’m thinking making it “strategy only” would be better?) I imagine the work will take half a day per week, but there may be times I need to do more / less. (timestamp: 18m44s)

When trying to build a consultative/advisory-oriented business, how do you manage clients who also want you to do the implementation? In my (admittedly limited) experience, the value to many businesses drops off considerably if the implementation isn’t part of the deal. (timestamp: 30m14s)

When a relative approaches me for my work, the “why did you choose me” question usually boils down to our personal relationship. Should I just skip this question altogether? (in general, the why conversation is less formal, how do I handle such cases?) (timestamp: 41m36s)

My current “retainer” for a few clients (before I started your “brains” focused models) includes both strategy & implementation. I can control what I “do” & they trust my judgment, but going from hourly-block-of-hours “retainers” to high-priced (their perception) advisory retainer (no doing) is a hard move. How do I deal with this as any new clients are getting the new way & I want to transition these older folks somehow (even if over time). If I don’t I’m going to resent them in time. (timestamp: 44m4s)

When do I know that supporting a software client is no longer in scope of “bug-free guarantee” but should start asking a retainer? (timestamp: 49m54s)

Do you have any techniques for writing to a specific audience and not slipping into writing to your peers? This has always been a huge struggle for me to the point where I wonder if I should just be selling to my peers instead. (timestamp: 1m10s)

After narrowing my positioning, how much time should I give it before concluding whether this version is working? (timestamp: 7m54s)

I’m trying to create an LFPS. I’m a software engineer with vast experience so creating a niche feels limiting. But on the other hand, I feel like my target audience is a bit too wide (I’m thinking to focus on local businesses as a demographic niche). Can you please do a teardown? “I’m a software engineer who helps business owners with custom software implementation. Unlike my competitors, I deliver a complete solution as speedy as possible, effortlessly” (timestamp: 14m42s)

Is product-market fit my problem here? I’ve written a daily email for 6 months now and am happy with its progress. I’ve kept up a consistent social media presence also and have 500+ followers on my platform of choice. Yet in this time I’ve only made a handful of sales. I get really positive feedback from readers and followers, but it doesn’t amount to many sales of one of two productized services I offer (a customized CRM and one-hour consulting call). Product-market fit, or impatience? Thanks! (timestamp: 25m33s)

On the spectrum of consulting to coaching, where do you believe corporate training workshops and courses land? (timestamp: 32m37s)

I’m struggling with the idea of offering team training workshops to Innovation Managers (who we currently serve with our design services) if I’ve never been an innovation manager myself, let alone have proof of success as one. Would it be better to aim workshops at my peers (other designers)? (timestamp: 38m18s)

I want to transition away from implementation work for a web application. I told the client in late 2021 that I would help on-board a new developer or team over the upcoming year. This was done on an hourly basis. Their plans fell through and they will need support again in 2023. I think my availability is worth more than the bits of hours I end up billing. How can I transition them from hourly support to a retainer style contract for this type of work? (timestamp: 45m20s)

How many qualified daily email subscribers are needed to support a thriving solo authority business? (That might be hard to give a universal answer to. If so, how many subscribers do you have again? How many do your most successful students have?) (timestamp: 51m16s)

Right now I require a structured roadmap phase before entering into a months-long custom engagement (my “program”), how would you explain this clearly on a sales page to outline the benefits (for them, moreso than me)? (timestamp: 56m24s)

Many of us struggle to get traction in our new business. How much of the problem is not having found a strong “expensive problem” to solve? What makes a really really good one? (What expensive problem do you focus on?) (timestamp: 61m55s)

How do I subcontract my work? I’m a single member LLC. Do they need a 1099 tax form? Do I need to report their income? Do I report income from them differently than my other income? (timestamp: 69m35s)

How does a Sales Tax Exemption Certificate work? What would be a reason to get one? (timestamp: 70m23s)

In the context of a fully custom software project (where the cheapest rung is an already expensive custom solution) is added features (which they might or might not ask for down the road) good for a product ladder? Otherwise I can’t see how to add value 5-fold. (timestamp: 70m55s)

When I’m having trouble in the why conversation, should I just ask outright “what’s your budget”? (timestamp: 79m52s)

I seem to be stuck between my ideal buyer either being a non-software CMO or non-marketing technical founder. I know you say target the top dog but the non-software CMO was my entry point into my current client, but the CEO signed the check. If they both express the same “want”, just shoot for the top? It definitely affects my marketing strategy as you can imagine speaking to either a non-technical or a technical person. (timestamp: 87m11s)

This probably overlaps with an earlier question: I’m also aiming to transitioning a client from advisory+implementation to just advisory. They have an ongoing dev team contracted, but I’m “their guy” for a specialized piece they don’t want that team to take. Any suggestions around an all-advisory three option proposal? Or is it just much easier to anchor against at least some implementation when that’s what someone is expecting? (timestamp: 90m5s)

I’m looking at creating a podcast to interview leaders in the data space. Are there any good templates out there for inviting someone on your podcast(that does not yet exist)? I’m trying to come up with a way to showcase that it will be beneficial for their careers and their authority. How does this work for you when you ask someone or get asked to join a show? (timestamp: 95m22s)

Can you comment on my LFPS? I’m a test automation expert who helps companies with scaling their printed circuit board testing. Unlike my competitors, I focus on small companies that are manually testing 10s of boards slowly to automated testing 100s of board very quickly and more thoroughly. (timestamp: 98m15s)

How would you handle a client asking for an NDA to be signed, for an R&D productized service? I think some of my ideal buyers have a valid reason for it, but it also undermines the “productized” part. (timestamp: 1m19s)

Can you go over some of your process for planning and recording Doing Daily? For example, do you plan to keep asking the same or similar questions? How did you choose the questions to ask? Do the answers help inform any other part of your work other than Email365? I don’t currently plan to start a podcast, but if I did, Doing Daily is the type of format I’d want to emulate as it’s quite informal and I think that would resonate with my audience. Thanks! (timestamp: 3m16s)

I want to make an MVP for a video course. How should I approach it so that it doesn’t get too detailed too fast? I’m not worried about the time investment of creating the course so much, as I can make videos and screen recordings really fast. I’m more concerned about making it overly detailed for an audience who aren’t all that tech and/or design savvy. You previously suggested that I start with webinars, but I can’t really commit to anything live just now due to having a newborn in the house. (timestamp: 8m32s)

You offer three types of advisory consulting (that I know of): Private coaching, group coaching, and a one-off coaching call. How did arrive at the relative price points for each of these? How would you advise someone considering offering some or all of these as well? How should they determine their price points, and should they offer all three at once, or start smaller? I already do a one-off call, and am considering adding private coaching next. Suggestions? (timestamp: 14m27s)

I’m charging hourly but my clients and I do all of our work together in that 1 hour. I show up with very little prep work and we get through as much of the work as we can on the call. We work 1 hour per week, week by week, to write their website. There’s no contract. They can cancel anytime but all of them come back the following week. Yes, it’s hourly but it feels more like how a physician or therapist works. Is this a bad thing? (timestamp: 24m6s)

How to set to create a business that doesn’t require your involvement to operate (owner-operator style). Even looking at your business, some significant components, like the slack community, the newsletter writing, and the bi-weekly calls, are dependent on your performance so if you want to take 3 weeks to unplug in the woods (or alternatively, if god forbid something medical happened to you or a member of the family and you’re unable to work), it’s not possible to go offline.How to balance? (timestamp: 27m35s)

Your private coaching sales page feels quite long. How intentional is this? (timestamp: 33m14s)

You mentioned on a TBOA episode that you’ve only worked with someone who was in too small a niche/specialization once. How did you determine that their ideal client profile was too narrow? For someone in this rare situation, how would you recommend they approach broadening to a somewhat larger market? (timestamp: 34m30s)

I’m worried my emails are getting lost in the Gmail Promotions tab. I give the standard tips in my opt-in (whitelist me, drag me to main) but it happens anyway. Any tips on how to get out of people’s Promotions tab -- once they are a subscriber? This one fix could bump open rates a lot. (timestamp: 40m27s)

Which yields the best results- speaking at conferences, podcasts, blogs, email list, anything else? When should you start seeing results? a quarter? (timestamp: 44m51s)

I work on front-end innovation projects so I very rarely have permission to show client work on our website. In an effort to add credibility & an understanding of what we help with to our website, I have added client testimonials and example project work (mostly studio-initiated projects). I want to add case studies as well, but cannot show any of the work or mention the client’s name. What are your thoughts on anonymous case studies? Is having anonymous case studies better than having none? (timestamp: 1m17s)

You said that writing daily “has been the single best thing you’ve ever done for your business.” How long after you started writing daily did you notice an uptick? What business improvement(s) did you notice? (timestamp: 8m37s)

If you focus on serving an audience, rather than on a specialization, what’s the best way to answer prospects who ask about this? For example, I don’t state that I’m a ‘marketer’ or a ‘graphic designer’. I prefer to focus on my positioning statement and the results I deliver for clients. But when prospects ask me what I do, it’s typically after they hear my positioning statement, so it feels like they’re after the ‘marketer’ or ‘graphic designer’ answer. Help! (timestamp: 15m8s)

If you notice that your services are being purchased by people adjacent to your target buyer, should you include them in your marketing messaging as well? Or is it best to keep the messaging ultra-focused on one main client type? (classified by their job title in my case) (timestamp: 29m18s)

How would you handle your emails and social media presence in a situation where you have two totally different authority businesses with two different email lists? This is during a transition period where one is growing and one is being retired (but you’re not sure how long a transition it will be). (timestamp: 37m37s)

What would be your Twitter replacement? :) (timestamp: 45m36s)

For a daily publishing habit to have a positive effect on an authority business, how many times a week would you guess is the minimum? You do 7 days / week. Others do 5, or 3. (timestamp: 48m21s)

Should blog articles and email newsletter pieces just live in those forms, or should they also be published in their entirety on LinkedIn, Twitter, etc. at the same time? Is there more value to keeping them in track-able, owned platforms? Or more value in broadcasting as much as possible to the widest audience? (timestamp: 54m46s)

You spoke at the MYOB conference in Atlanta recently (nice to see you there!). You used to speak at conferences frequently. Did that conference have any good results on your business yet that you know of? Could you imagine a world where you no longer need to travel to speak? (timestamp: 57m27s)

How can I leverage value pricing for UX services? UX is so far upstream to make any significant impact on the bottom line, like devs/engineers. (timestamp: 61m1s)

Should I send my “Book a paid call” page, when someone emails me a promising project inquiry that I can already tell I won’t have availability for? If so, can you suggest wording that feels less pushy right off the bat? Thank! (timestamp: 66m19s)

Could I get a last minute positioning teardown (and you can reply in Slack if that’s easier)? LFPS: I am a Developer Education Consultant who helps small open source companies with removing friction in their learning experience that prevents adoption. Unlike my competitors, I infuse my game design passion to create “gamified” educational content that inspires developers who have literally called it “lovely.” (timestamp: 72m12s)

If you were doing paid promotions/sponsorships/ads for an education product business, would you send people to specific product, or your newsletter? My gut says "start with the list, the first ’product’ in the funnel." (timestamp: 2m38s)

A potential competitor turned a polite twitter conversation with me into a blog post on medium and LI, trashed my content for his purposes, quoted but didn’t attribute and then brushed off any attempt at having a discussion in public. How can I leverage the social media impact to my advantage while (nicely) slapping his head? (timestamp: 4m36s)

Multiple & Passive Income Streams I’m considering: • Writing a book • Should I self-publish my book or go with a traditional publisher? • How would I go about writing the book, publishing, proofreading, etc.? (timestamp: 5m58s)

How do I get help, but not an employee? How do I hire a contractor or similar position? Does working with such platforms as UpWork beneficial? (timestamp: 8m36s)

I’m in the process of creating a corporate team training workshop. I want to follow your advice of running three betas before launching the workshop to the public in order to improve the workshop and understand how to price it. Who would you seek out to be a beta tester and how would you find them? (timestamp: 10m34s)

How do you know when it’s time to quit? I’m not asking based on any recent experience in particular, but this was a topic recently covered on Ryan Holiday’s Daily Stoic podcast. So, I was interested to hear your general take on it. For some added context, on the podcast they covered walking away from things that don’t align with your beliefs and making decisions in service of a larger goal. Thanks! (timestamp: 14m0s)

Looking for a different client I have one client (my first) and would like to work with a different client instead. I haven’t found a different client, but would like to know how to find him/her. (timestamp: 20m23s)

Looking for clients by using their products I am currently trying to get relationships started with potential clients by using their products and getting help using their products by contacting their technical support. This seems like a way to talk to the end user or at least to get my name known to potential people in their organization. What do you think of this? (timestamp: 23m25s)

What are the top 3 or so ways to market my business? Things I’ve thought about: • YouTube • Twitter • LinkedIn • TikTok • Website • Testimonials • Car Sign • License Plate Frame • Business Cards • Blog • Paid Ads • Cold Calling • Email / Mailing List • Ask experts for an interview - I tweeted Elon Musk and asked for 5 or 10 minutes of his time. • Surveys • Podcast (timestamp: 28m25s)

Dealing with project delays caused by waiting for customer How do you manage a client who keeps holding you up because you are waiting for something from them. Waiting may be a waste of time. Adding another client could come back to bite you when the first one is ready to resume. (timestamp: 32m42s)

Pricing the whole project or phases of it Should I price the whole project or individual phases of it? It seems like their could be a large possibility of the project changing as it is being implemented and that the business needs could evolve as well. This may make much of the proposal not in sync with these evolved needs. (timestamp: 37m21s)

Managing the Pipeline My workload for my existing client is diminishing each week and I’m ready to take on a second client as I now have more time. How would I manage my workload when multiple clients overlap? (timestamp: 43m27s)

Project is a lot more involved than expected after accepting client How do you handle unplanned work that pops up? Can you ask for an example of system that your project will integrate with? (timestamp: 48m52s)

Hi Jonathan. Your own positioning statement says you teach ’experts’. Experts is a broad ’niche’, of course: people can be experts in almost anything. Is this a way to be a specialist and a generalist at the same time (that appeals to me!)? And what tips (other than just ’look at LinkedIn’) do you have for finding experts… (in my case, I help people produce books: how would you identify people who have already written content that now needs help of this kind?) (timestamp: 52m39s)

I have an idea for a workshop that I feel will serve my existing client type well (just solving their problem in a different way than I already do). I don’t want to launch the workshop to crickets, but also don’t want to require myself to do so much due diligence prior to launch that I waste time or psych myself out. How would you strike a balance? (timestamp: 64m38s)

My automation agency helps businesses automate their customer and employee onboarding workflows. I want to create recurring revenue without selling hourly retainers I’m struggling to find a way to a put a usage limit to keep my costs to a certain level. I have in mind a product where we would have a backlog of ’things’ that need to be automated and tackle those items each month... Do you have an idea on how to “limit” without talking hours? (timestamp: 68m58s)

How would you re-engage an email list you’ve just collected with a lead magnet but that you never emailed (other than for the subscription opt-in)? (timestamp: 77m32s)

I’m struggling with figuring out the correct tactics for this overall objective: Make it simple for clients to find me and purchase from me (at higher altitude – no coding) I have more of a platform spec. & any content I’ve put together interests devs (not buyers). Is this best place to start? Could you share how you solved this via your mobile business. When you wrote books was the target the dev groups that were trying to solve these problems or was it the CIO/CEO that were the actual buyer? (timestamp: 79m12s)

What speaking opportunities have generated the most leads for you?
Out of the various speaking opportunities you’ve had, which did you find had the greatest ROI for you (lead gen wise) and why? I.e. Being a podcast guest, speaking at a conference, hosting a workshop, hosting an AMA, hosting a webinar, other. (timestamp: 1m30s)

How can we test whether a target market is too small?
We’ve niched down to offer a very specific service to a very specific client and while we have done many of these projects over the years, new clients are extremely hard to find. I’m wondering if we need to push our marketing efforts even harder or widen our target. How would you test whether or not the target market you’ve picked is too small? (timestamp: 6m43s)

What are the pros and cons of paid referrals?
What do you see as the PROs and CONs of offering past (good) clients a referral program where you pay them personally a 20% commission for any new client projects they push your way? (timestamp: 13m46s)

Did you claim your big idea / “Sun” (i.e., ditching hourly billing) after or before you got a positive reaction from your audience on it?
(timestamp: 18m5s)

Is it better to speak to the promise or offering in an elevator pitch?
In an elevator pitch, is it better to speak to the promise or offering of your value proposition? For example, I help Innovation Managers get their stakeholders to act. OR I help Innovation Managers generate & illustrate their product ideas. (timestamp: 21m49s)

What should I do if a competitor launches a podcast very similar to mine?
OH NO! I was on the verge of starting to record the very first podcast in my little niche, after 5DPC and months of planning. This week, a competitor scooped me. They launched one with 3 shows released and 10 recorded. They’re now the first. Very similar to what I planned. What should I do? Record my first shows and launch anyway? Observe theirs for a while and then launch mine as a fast follower? Or call it a learning experience about procrastination, and move on? [Muffled crying noises] (timestamp: 29m51s)

Would you review my laser-focused positioning statement?
I would love to get some feedback on my LFPS. Here goes: “I’m a career coach who helps Java students land their first development job. Unlike my competitors I help students focus their job search on a certain type of company to speed up the job application process.” (timestamp: 33m45s)

Should I broaden my brand to encompass newer offerings that fall outside of the current one?
Over the last 6 years, I’ve grown my brand as the “Vanilla JS Guy.” I’m considering expanding into adjacent topics, like CSS/HTML. Should I add those courses under the Vanilla JS umbrella, or rebrand (to something like The Lean Web)? (timestamp: 40m59s)

How do you handle procrastination?
Have you ever dealt with procrastination (either in yourself or others)? If so, how did you handle it? Thanks! (timestamp: 47m42s)

How important is it to have a memorable brand name or tagline when positioning yourself solo?
Your Makeover Maken series is awesome as a positioning 101. How important do you think it is to create a memorable brand name or tagline when positioning yourself solo? I ask because my name can be hard to pronounce/memorize... Or does that not matter really? Just curious how you think about that. (timestamp: 54m27s)

Should I add a minimum # of months commitment to my membership program?
My current services portfolio consist of 2 productized services and 1 membership (CEO Mastermind). I am thinking of offering all three of them ’as a Service’ (Predictable Traction as a Service) cause put together they offer the biggest impact for my customers. The challenge I am trying to get around is this: Should I add a minimum # of months commitment (f.ex. 6 months) to cover for at least the front loaded value (my main productized service which typically is sold for 15K upfront). (timestamp: 60m45s)

How would you grow a solid product business that has plateaued?
After six years, my JavaScript education product business seems to have hit a bit of a plateau. I’m trying to figure out how to take it to the next level. I’m worried I’m struggling from “what got you here won’t get you there.” I have time to think about this strategically. What should I do? (timestamp: 70m1s)

How do I know if I’m doing enough to generate inbound leads?
I’m currently writing a daily email, posting three times a week to Instagram (the main platform my audience uses), and I’m about to start posting weekly YouTube videos. I feel like this is manageable, but is this too much or too little? I also spark up conversations via DM on Instagram every day with those in my target audience (which would count as outbound, but it’s another tactic I’m implementing). (timestamp: 3m8s)

What if my target is facing too many different types of problems?
Say you’ve narrowed down a target audience. You start interviewing people and quickly realize there is a lot of variety in the problems they’re facing. Do you a) keep at it, you know you’ll eventually find a problem you’re qualified to solve or b) try to niche further/identify a subsector of your target market? Also, is the goal to find a problem you can solve (diamond in the ruff), or to identify commonalities amongst the group and then make a decision based on what you can help with? (timestamp: 7m2s)

How much should I engage in a watering hole that my target market hangs out in?
I’m a bit confused on when to and when to not engage in an online community (where our ideal clients hangout). I understand that showing up and being helpful by sharing answers/content is a good way to attract leads. I also understand that NOT posting anything and just lurking is the best way to learn about our ideal clients w/o drawing unwanted attention to ourselves. So what do you recommend we do in these “watering holes” that we get into? (timestamp: 15m29s)

How might I extend my business from just serving to B2C to B2B as well?
I’ve been doing B2C coaching for years. I have a ton of published content for that audience. My audience is tiny, but quite engaged. Lately, I’ve been building a separate B2B business providing (mostly ghost written) content, copy and strategy for tech companies that also serve my coaching audience. I’d like to hear your thoughts on how to combine the marketing efforts for these two businesses? As they both align with my overall mission. (timestamp: 19m31s)

Do you think B2B clients care about Behind-The-Scenes content?
(where you show a more human side of your business workings or personal life). (timestamp: 27m31s)

What do you recommend putting for your LinkedIn headline?
Positioning statement, personal tagline, or something else? (timestamp: 33m46s)

Do you believe in advertising?
(Explicitly promoting your offer where your ideal buyer hangs out) (timestamp: 37m5s)

What’s a good target % of time to dedicate to content marketing?
For a specialized engineering consultant, what’s a good target % of time to dedicate to content marketing (professional articles, email newsletter, social posts, etc.)? I’m currently targeting 40%, but I’m also in the early phases. (timestamp: 39m13s)

Any tips for making daily writing feel ‘snappy?’
On a mission to find some engagement, I’ve resorted to TikTok and finding it surprisingly enjoyable. Great for not overthinking stuff and getting into the ’make it snappy’ mindset. Any tips for getting that feeling into daily writing? What do you do before you hit ’send’? (timestamp: 42m41s)

How can I sell new things to my existing client base?
I was recently introduced to the practice of “hunting the farm” to generate more business. It’s where you propose unsolicited ideas, opportunities, or brainstorms to existing clients to drive additional work with them. I’ve always steered clear of up-selling to avoid being slimy, but I am starting to imagine how valuable/appreciated it would be if my clients had someone seeking out additional ways for them to succeed. Are you for or against it? If you’re for it, how would you go about it? (timestamp: 49m24s)

How do you recommend pricing monthly agreements with no set scope or pre-determined value?
I’m transitioning to a different market, but maintain a few client agreements that are hourly-based. I recently had a client push back on this as they were unhappy with the number of hours in a billing cycle. I know this is probably a dumb question to ask the ‘Ditching Hourly Guy’, but what approach would you suggest here? I will eventually drop this work but for now this is ‘keep the lights on’ money. (timestamp: 57m31s)

What guarantees should I offer for roadmapping and recruitment?
I recently offered two new services: 1. Application road-mapping: This is a typical road-mapping and high-level timeline offering. 2. Team recruitment & app selection: To interview and hire a team of consultants for the client and also recommend some internal working apps (Trello, JIRA, etc). For each service, I’m not sure what kind of guarantee to offer. Any suggestions? (timestamp: 64m3s)

Did I niche down a little too much?
I’m working on implementing Zendesk but getting leads flow consistently has been a struggle. Should I broaden my work to other platforms? Where do you cross the line between over-niching and over-spreading? (timestamp: 73m12s)

What does Ditcherville mean?
(timestamp: 82m22s)

Is it better to have a large number of small clients, or a small number of large clients?
Several Ditchers said they are always anxious about losing a big client. You have said you are deliberately moving to a many-small-clients model. Is that model less stressful? (timestamp: 83m36s)

In what situation(s) would you offer a productized service for free in exchange for things like feedback, etc?
I don’t actually know whether my prospect has an exact need for what I’m offering. The only reason I think to work with them is they’re in my target audience and we have a good relationship. How to think about this? (timestamp: 89m38s)

Can you cover the pros and cons of niche vs platform specialization?
The majority of my leads come from word of mouth refs for having a platform specialty (ie being an expert in X tool) - The tool itself (Power BI - data visualization) seems like just a conversation starter and I end up helping the client in a variety of ways (some not specific to the tool - ie dev workflows, modeling, etc) Can we cover the pros and cons of niche vs platform specialization? (timestamp: 93m16s)

Does it make sense to use domain redirects for marketing?
I saw you doing that a lot but I am wondering what is a real outcome of that. On my opinion if you show up the redirect domain people will remember the redirect url but not the final destination which is more important unless I am missing something. Also there is a chance that you may forget to pay for that fancy domain name some day... but that is another story 🤣 (timestamp: 1m49s)

How can a junior developer learn the skills to help senior decision makers?
I’m working as a junior developer but my goal is to move towards coaching senior decision makers on how to be more successful. How can I learn the skills to help them if all my current work is hands on and I’m not a part of any strategic processes at this company? I can identify business problems at work and have thought of some theoretical solutions, but I’m not sure how I can get the experience to validate that those solutions work. (timestamp: 9m5s)

Does it make sense to put a services calculator on a website?
Does it make sense to put a services calculator on a website for custom development, prototyping (not advisory services) ? The idea is to show the price ranges based on params like project size, urgency, number of iterations, etc. so yeah it is not a fixed priced calculator. However maybe it is worthwhile to experiment with that but I wonder if it makes sense to have such a calculator on a website at all, have you seen anything like that and would you recommend that at all? (timestamp: 24m4s)

Does it make sense to pick a niche if my services would be the same for anyone?
I’m toying with niching down to serve expat solopreneurs. I’m one, many of my clients are (though I do no messaging on this). Hosting a summit, figuring out which groups to join, etc. immediately becomes clear. But the problem is there’s no problem. Expat solopreneurs have the same problems as any other solopreneur. I wouldn’t know how to market with this ‘angle’. My web design approach or process doesn’t really change when the client is an expat. So is this a dumb niche idea? (timestamp: 29m16s)

How do I know if I picked the right target market?
What should I be looking out for to ensure I’m on the right track when entering a new market? Since TPS 9, I’ve been actively speaking and working with a few clients in a new space. The work I’m doing isn’t even remotely close to replacing my income from my larger clients. I’m not put off by any means, but I suppose I have a bit of self-doubt. As I’ve been in situations before where pivots have flopped, so I’d like to ensure I stay on the right course. (timestamp: 38m37s)

Should I start a podcast or a YouTube channel?
When starting a new YouTube channel, what approach would you recommend? I saw you mention in a recent presentation that people should do writing and speaking regularly. I have daily emails for writing, but I don’t currently do any regular speaking. I considered starting a podcast but creating videos is much more up my alley. What would you suggest is a good strategy to use here? Topics to cover? Video length? Frequency? Thanks! (timestamp: 50m32s)

Is cold outreach a necessary part of bootstrapping a consultancy business?
And how much effort should you put into that vs writing/podcasting? i.e. in the early stages “keeping the lights on” vs “tending the garden” (timestamp: 58m6s)

Should I make my daily emails public or just send them to the subscribers?
You mentioned recently early on you didn’t make your daily emails public. For new daily publishers, what do you think about starting off with punk marketing and publishing everything freely? I auto-post to Twitter where a lot of my audience is. (timestamp: 65m46s)

How do I deal with regional differences in terminology on my mailing list?
When building an audience, should I focus on targeting those local to me in my niche or should I always be keeping a wider, more international audience in mind? I work with people who officiate at weddings. In the UK they’re called ‘celebrants’ and in the US they’re called ‘officiants’. That’s a small distinction, but legally there are quite a few big differences. And when writing my newsletter, addressing both gets a bit long-winded sometimes. (timestamp: 2m32s)

What should I do if I uncover organizational dysfunction during a discovery project with a new client?
A discovery project seems like it would uncover internal politics or cultural issues. Would you address those directly with your buyer, let sleeping dogs lie, or pull the plug? If your buyer is happy with the roadmap and success measures, would you still propose an option to do execution in that environment? (timestamp: 10m25s)

Is a 24/7 advisory retainer a good fit for someone who highly values structuring their time?
Hi J, could you please talk through some different ways an advisory retainer might look in practice for someone who really values structuring their time & is a little terrified of 24/7 access? I want to stop selling time for money, but I don’t want to sacrifice my well-being. I currently divide my day into blocks so I can focus on deep work & concentrate on one thing at a time. Longer response times? Batching responses? Set office hours? Would love to hear any & all ideas please 💕 (timestamp: 15m50s)

Should I focus on the 20% that bring in (much) more than 80% of my income, or should I keep working my ass off offering courses?
Background: I offer 1:1 visual coaching to help people sort out their ideas. We talk, I draw. It works well, and I will have the best revenue year ever - mostly from one client (IT CEO) and a handful other happy 1:1 clients I also have a membership “Visual Thinking for Business”, that I love - but it doesn’t run by itself. Yet. (timestamp: 26m25s)

What’s a good approach for offering discounts in exchange for referrals?
I just had a meeting with an organization that accredits professionals in my audience. They said they’re happy to refer their members to me but they’d like to offer them a discount, which I’m happy to do. But I’m assuming I should make that time-bound? Or limited in some way? (timestamp: 32m26s)

How do you decide when to raise prices?
I’m considering raising the price of my flagship product (a cohort based online workshop) by 25% (from $795 to $995), in the hopes of growing revenue. Is this a bad idea? Are there any things I should be thinking about before I do this? PUT DIFFERENTLY: How do you decide when to raise prices? (timestamp: 39m19s)

How do I know if something is a good candidate for a productized service?
Google is upgrading the environment in which Google Ads scripts run; all scripts need to be migrated before end of Oct 2022. There are a lot of scripts that need minor adjustments to the code. Most Google Ads consultants don’t know how to make these adjustments. I can do this for them within an hour. Is this a candidate for productized service? It feels like something I can test with little effort. Would you try this, if so, how? (timestamp: 50m15s)

Is there a maximum dollar amount that I should publish on my website for a productized offering?
Hi Jonathan. Wondering if there is a maximum $ amount that should be shown on a website for productized offerings. I have 2 types of training programs where I plan to show pricing per participant with a requirement for a minimum number of participants. For my Strategy Workshop Facilitation product, I would show a fixed fee. For example, the training cost could be between $1,200 to $2,000 per person but the workshop fee could be $15,000 to $20,000. (timestamp: 56m7s)

Does it make sense to front-load my membership community with a basic course that new members go through?
I am planning to launch a subscription based Design Thinking training/coaching community. My idea is to get participants started with a basic course in Design Thinking (Intro plus 4 modules) and then drop an additional module every month. I would also offer drop-in coaching (similar to this). Wondering if front loading the learning makes sense. (timestamp: 62m33s)

How should I pick a niche?
Any suggestions on picking a niche and getting started building authority. Context: I started with Rails dev but can completely manage a project from scoping out the work, evaluating the business case, and running a small team, but my experience is broad, SaaS startup through internal business tools, not focused on one vertical for example. (timestamp: 2m48s)

What’s a good approach for validating and creating a short video course?
I have an idea for a video course (maybe 60 mins or so of content) that prospects and clients have shown interest in, but I’m not sure how to approach it. I’m happy beta-testing new services with clients, but what’s a good approach here to avoid creating a bunch of content to have it flop, or for people to say it’s not all that valuable to them? (timestamp: 22m32s)

What’s the ideal length for a daily email?
I’ve seen short ones, like Seth Godin and yourself, but also much longer ones, from members of Ditcherville. (timestamp: 25m50s)

Is your weekly Ditcherville comic just for fun or is there a strategy behind it?
Love the Ditcherville comic, look forward to it every weekend. Is that just for fun, or is there a strategy behind it that would apply to other folks doing content marketing? (timestamp: 29m41s)

How do I grow my daily mailing list?
A Ditcher in Slack recently posted: “So I’ve been writing daily for over two months now and I’ve had zero more sign-ups and in fact lost a couple. Erm, progress!? I was wondering when exactly to spend a bit of time reviewing my posts and possibly making a lead magnet out of the best ones and how often it might be appropriate to do that?” I’m wondering the same thing. Can you go over some tips on how to grow an email list if it’s not growing? (timestamp: 33m5s)

How does someone brand new to consulting get started with value pricing?
I’m brand new to independent consulting work (previously doing individual contributor-type work under several corporate layers) . . . how do I approach pricing when I don’t have prior background in understanding the client’s perception of value? Assuming the “why” conversation goes really well, how do I translate that to a price in a proposal? Trial and error? Looking at comps from others in my space? Something else? (timestamp: 42m58s)

Should my home page focus on one entry level service or show all four?
I am currently going through a redesign of my website and am pondering over the following: Profile all (4) services on my homepage or just focus on 1? And then the next question related to that (if it’s just 1) - which one: The easiest entry for a customer (f.ex Roadmap) or my signature service where I deliver the biggest value). What’s your take on this? (timestamp: 52m12s)

How do I know when it’s time to broaden my positioning?
I’m have target buyers adjacent to my usual ones, who tend to have much more expensive problems using the same skills. They still find me occasionally through referrals, but they aren’t really who I’ve been speaking to over the last 5+ years. How would you evaluate pursuing an adjustment in positioning? I like this audience as well, but I have dramatically less clarity on what to write to help them—any suggestions on how I should think about this situation? (timestamp: 57m38s)

What should I do when I get an attractive lead from outside my chosen niche?
Let’s say you found your niche, it starts to work: How do you deal with request for something you’d find a cool project but it’s not a great fit your chosen niche? (timestamp: 62m13s)

How do I know what to write in the benefits section of a project proposal when I’m just starting out?
If you’re at square zero with no client results, and you’re working on your first proposal, how do you fill out the benefits section with any quantifiable information? (e.g. Increase leads by ???) (timestamp: 5m22s)

Should everything I sell have a 100% guarantee?
I wonder if 100% guarantee is valid thing for everything you do? (not talking about a proposals here). Would you keep 100% guarantee for each tier within your solar system? To be more specific is there any reasons for having 100% guarantee for top tier, say for 3-5 week 1v1 mentoring, as buyers of that option are usually people who already trust you and probably already bought a couple of smaller priced things from you. Can it potentially devalue that top offer in the eyes of buyer? (timestamp: 11m35s)

How can I ensure I’m asking prospects valuable questions?
I have several conversations with prospects via Instagram DMs, which are typically more short-form due to the platform. I often find myself starting with, “What is your most challenging business problem?” but then end up asking multiple questions all in one go after that, but I’m conscious that this could be overwhelming. Any tips here? As I’ve noticed in Slack that you are very succinct and effective with questions. Thanks! (timestamp: 18m16s)

How can we break out of the “rent-an-engineer” monthly model?
My company embeds with startups to engineer new IoT products. The client’s situation is always chaotic, there is no revenue (just investment $), and the client’s engineering team is drowning. It’s very hard to have the “why” conversation and value pricing while the buyer is drowning (“what, exactly, is the value of this life preserver to you?”). So, we almost always fall back to monthly billing (basically rent-a-full-time-engineer). How do we stop this cycle? (timestamp: 26m48s)

What should I do when there’s a leadership shakeup during an active project?
One of the Founders of the NGO I’m working with is stepping down after 8 weeks of being on leave. Am on good terms with the other Founder who I believe will be taking over. My biggest concern is that neither of them have really been involved in the project and consequentially it’s been hard to drive the project forward which has meant it has dragged on longer than I’d like. Might be worth clarifying who is the “project owner” + roles/responsibilities. What do you think would be most effective? (timestamp: 39m43s)

What is your thought process when you go about pricing your ebooks?
(timestamp: 46m44s)

How do I value price services that don’t provide any financial ROI?
Part 1: For those who have a service based business that benefits the client with lifestyle improvement rather than seeing a financial improvement, how can you have a stab at what they’d consider the financial value of your service to be? Part 2: How you value the worth of something is linked to your own sense of wealth, so with a global recession heading our way, how do you hold your nerve to ask the higher prices when you know that the general feeling is of financial unease? (Sorry to be gloomy!) (timestamp: 50m8s)

How do I raise my fees for existing clients?
What’s your advice on how to approach raising retainer fees? I have a handful of hourly-based retainer contracts with existing clients. I’d eventually like to transition away from these, but I’m not able to yet. However, I need to raise my fees for a few of them as I haven’t done so in a while. What’s a good way to do this without simply citing something like inflation (which is what I’ve done in the past, but didn’t feel all that great). (timestamp: 4m30s)

Should I explain value pricing to my prospective clients?
Have you ever explained to the client you’re doing value-based pricing? Have you seen students (or personally) where a client already comes to you understanding VBP (like other consultants)? If so, what was that like? (timestamp: 15m38s)

Are there times when 10/22/50% “Goldilocks” project pricing is a bad fit?
In what situations, would you advise changing the price calculation to be something other than 10% (lower or higher)? (timestamp: 26m19s)

Should I make up a “catch-all” term for the two different types of target markets in my positioning?
Am working with both early-stage, mission-driven startups and tech non-profits. My idea was to fold both client types into a broader “social impact” category around which to focus my positioning so that I can a) work with any business no matter the structure/model, and b) because I think I will get a lot of energy from this category. I’m having some difficulty with the “social impact” positioning because I think there are pre-existing connotations (such as that it refers to the social sector). (timestamp: 30m44s)

Would it be confusing to include an advisory retainer as an option in a project proposal?
Would you ever suggest putting an advisory retainer as part of a tier 3 proposal option, or does that get confusing? (timestamp: 43m37s)

Should outbound be part of a solo consultant’s bizdev strategy?
I’ve published regularly over past few years & built up some authority in my space (AWS cloud), but I’m still not getting enough leads. I feel my mailing list (over 1k) is mainly devs rather than senior roles that might hire me for consulting. I’ve shyed away from outbound (LinkedIn, cold emails) but feel I should try it, even if only to have more conversations. Have you seen any outbound tactics work well for software soloists? (timestamp: 49m17s)

What should I do when I have time to work ON my business instead of IN it?
What should my focus be while I have some spare time? Most of my clients are larger firms who pay me a monthly retainer, so I’m not too worried the current lull I’m going through due to summer/holidays. But I’m actively transitioning to a more soloist audience, sending daily emails, and sparking up conversations where I can on social media. Should I be focussing on building my audience, creating productized services, or something else? Or all of the above? (timestamp: 2m38s)

How do I know when a value priced software project is done so I can start a new one?
I’m nearing the end of a value priced software project, but not exactly sure when it will end. I don’t want the next one to overlap. When you have people interested in working with you personally, incl. the current client, what steps should you take? Long-term, I know I need more low touch options in my product ladder, but short term I’d like to have better conversations around when I am next available for custom projects. Thank you! (timestamp: 7m34s)

How much validation do I need to create a productised service?
I’m having quite a few conversations with prospects, but I’m not able to steer them to a point where they 100% validate my assumptions. For example, plenty of them currently use or have dabbled in Google Ads. This is a service I already provide but haven’t productised. Should I go ahead with templating it out and beta-testing it? Or do you have suggestions around how I can get more confirmation from prospects? (timestamp: 18m4s)

What exactly is a roadmap?
Is it just an outline of a process, with a schedule? Can it be more than that? Any pointers to resources to learn more? That reader success story got me excited to sell some. (timestamp: 28m45s)

What would a “tools and guidance” business look like for some one with a software background?
Hi Jonathan! The ‘hybrid’ (‘equip and guide you as a group’) model seems to be popular - and attractive - as you can make a high impact with a lower touch than custom/1-on-1. (I think of your Pricing Seminar). From your own experience - and your students - do you think this hybrid model could work for software-focused expertise? If so, what do you think a progression would be from hands-on custom projects to this model? Thanks! (timestamp: 38m56s)

Is a daily email useful for any kind of expertise-based business?
A daily email seems perfect for experts who essentially help people improve over time (eg., Ditcherville). But is it right for all experts? What about someone who sells a one-time service, like initial setup of business software for beauty salons? How would you strategize the content of that daily email? (timestamp: 45m9s)

How many subscribers is enough?
Based on your numbers, what is the ratio of total email subscribers versus how many of them purchase a book? Group coaching? Private coaching? What is the ratio of how many subscribers hit reply to your emails? Essentially, how many subscribers is enough? (timestamp: 56m22s)

How can I expand beyond my initial target niche market if it’s too small?
I’ve already published a book about SEO and now I’m focusing more on productize services for that. My worries is that the niche is too small and I wouldn’t be able to expand later to other audiences outside of SEO People like you’re doing today with billing and expanding to architects. Do you think this is a problem or something to figure out later? (timestamp: 65m50s)

How can I pivot to a new area of expertise when I get sick of the old one?
I recently realized I don’t really have an interest in my expertise area. I am good at it and I am an expert, but it’s really not interesting - it kinda where life lead me. However, I gotta keep going to pay the bills. Any advice for a soloist in this situation? (timestamp: 73m23s)

What if I offer a money back guarantee and a client invokes it after I’ve done months worth of work?
You suggest asking a client for payment up front and offering a money back guarantee. Imagine a nightmare scenario where I work on a project for many months only to find the client wants their money back at the end of the engagement due to miscommunication or bad faith on their part. How does one minimize the risk of this happening? Should one simply not offer a money back guarantee on work that extends for multiple months like this? (timestamp: 1m51s)

How should I validate new ideas to add to my product ladder?
Can you recommend a strategy to validate new ideas for productised services? I have a handful of clients that I feel comfortable asking for feedback, but what’s a good approach here? Should I simply prepare a laundry list of ideas and ask them for feedback on which seems the most valuable to them? Or is there a better approach to utilise? Thanks! (timestamp: 13m33s)

What’s the maximum viable complexity for a productized service?
We’re reaching a level of standardization in our website production processes that could allow us to pull this off despite being months-long projects. What I’m wondering is whether it makes sense marketing-wise since potential customers would need to understand a fairly complex process in order to decide if it’s right for them. (timestamp: 18m29s)

How should I handle it if my buyer hands me off to a micromanager mid-project?
Had a project with a client (a bank), and they sent their IT manager to check the progress of the project. The problem is that their manager is micro-managing me even though I gave a fixed price for the project. She’s been asking for reports of the progress in a rude manner and at the beginning She asked for an estimate of the project before sending my quote. I told her to be approx. 2 months (with some uncertainty) and She turned that into a deadline. What would you do in this situation? (timestamp: 25m23s)

What factors should I include in a pricing calculator on my website?
I came up with a number of fixed priced consulting-advisory productized services that I want to launch sometime soon. I want to build a pricing calculator that will be placed on my site to help to qualify the leads. I am curious what the best pricing factors should be included in such a calculator and what pricing multiplicators should be used accordingly. For example number of iterations (1 iteration - 1x, 2 iterations - 1.5x, 3 iterations - 2x), urgency (not urgent - 1x, urgent - 3x), etc (timestamp: 35m18s)

How do you keep track of what you write every day so you don’t repeat yourself?
When writing a daily email or blog, how do you keep track of what you’re written, so that you don’t repeat yourself? I sometimes find myself writing an entire blog post about the same subject that I wrote about a couple years ago. Does repeating yourself not matter? (timestamp: 40m42s)

How do I down-sell clients who don’t need my primary offering without sounding desperate?
What should my course of action be when speaking with a prospect who has already solved the main problem that I focus on? For context, my main productised service is a CRM, but I’m in the process of adding more rungs to my product ladder. A few prospects I speak to already have a CRM, but I often find that there are other areas where I could help them. How do I communicate this without sounding pitchy/desperate? (timestamp: 43m50s)

How would you price an ebook?
We have two free ebooks and one paid ebook. The free ebooks have been downloaded over 4k times, but the paid book sold less than 100 copies. It’s currently $35 with a $10 add-on for interactive exercises. I’d really prefer to get it in more hands than to view it as a significant source of revenue. Should we lower the price? How much? This is especially relevant since we’re about to launch v2 of the paid book and set up a marketing sequence to free ebook downloaders. (timestamp: 51m55s)

How should I justify my prices with only a couple of projects in my portfolio?
I am a Flutter Developer who has experience with building two social media apps before. The problem is that it is challenging to find social media applications that uses the tech stack I am an expert in. How can you understand that you are narrowing down your niche too much? The other question is: I am 25 years old. I have only two years of experience in the field. What should I do to justify my prices when the number of results I can showcase is not too much? (timestamp: 62m53s)

How can I divorce my prices from my location?
I am a software developer living in Turkey. Most US companies assume that I will be a cheap option due to my geography. When I price my services close to the US prices, they freak out. How can I divorce my prices from my geolocation? (timestamp: 75m31s)

Is hourly billing nuts for all types of labor, including full-time employees?
How would a barista or receptionist or... Wal-Mart greeter... handle VBP? There are different levels of skill in those jobs, too. (timestamp: 82m35s)

How might I control scope with an on-going retainer where I am doing implementation?
In simple terms, how would you explain the difference between how you price a fixed scope project vs an on-going engagement? In my case, I am speaking to an agency Founder who works with the same types of clients as I do, but who runs their business differently and doesn’t appear to be familiar with value-based/custom pricing. (timestamp: 88m43s)

What can I do to grow my daily mailing list?
After starting an email list and emailing daily, what should the next steps be? I’m very early into my audience building journey, but I’ve already had someone from my list enquire about one of my productized services and book a call with me. Thinking ahead, should my primary focus be on growing my list before adding more services? Or what’s the next step, now that I’ve got the ball rolling here. Thanks! (timestamp: 4m22s)

How do I clearly distinguish between the free calls and paid calls on my site?
I’m experimenting with a new productized service to help a Laravel dev “get unstuck” on a Zoom call with me. I want to add this to my site, but my current CTA is “book a free 30 minute call”. That’s geared at qualifying ongoing coaching/dev clients for much higher ticket engagement. How can I add the productized service (a call to help) without confusing it with my current CTA (call to see if we can help)? (timestamp: 11m51s)

Are startups much harder to sell advisory work to than more established companies?
Are startups much harder to sell advisory work to than more established companies? Someone I respect said to me last week: “the nature of a startup bakes in the assumption that they already know the best way to do a thing & the problem they need solved is simply the thing getting done.” I’ve been trying to sell advisory-only productised services (roadmap, retainer) to startups over past 12 months with very limited success. Almost all leads I get want me to write the code to build their product. (timestamp: 17m36s)

How can I keep my daily emails short, sweet, and valuable?
Been daily publishing for two weeks. It’s been helping me refine my thinking and build metaphors, but it takes awhile to tease them out. What are your guidelines for keeping your emails short, sweet, and most of all, valuable? (timestamp: 25m29s)

What’s your take on partnerships with other service providers?
What’s your take on partnerships, or informal agreements with other service providers? My audience are soloists, and some have suggested that I partner with another person in the space operating in a training/accreditation capacity. I’m involved in more growth and execution (i.e., after people have trained and are qualified and want to grow their business). There’s a tiny amount of crossover, as they offer some basic training on areas I specialise in, but it’s very surface level. (timestamp: 32m13s)

What are some good examples of productized design services?
Have you seen any good examples of productized design services? Since the nature of the work is iterative it’s kinda hard to come up a model that make sense for the customer. Most of what I’ve seen is selling time, like monthly subscription, but I’m not a fan. (timestamp: 35m1s)

Should I mix training workshops into my advisory retainers?
What are your thoughts on offering a project-level retainer for technical training/tutoring? What I mean here is going beyond the gap analysis in scope for project oversight — this offering would include project oversight — to proactively deliver custom internal tutorials/workshops as I see fit to remedy staff skill gaps within my area of expertise, while staying above the I-do-it-for-you altitude of involvement. (timestamp: 41m29s)

What general guidelines would you offer about when to document a process?
What general guidelines would you offer about when to document a process? And once you’ve decided to, what initial steps do you take to get started? If you’ve talked about this topic elsewhere, I’d love to learn more. (timestamp: 48m49s)

How do I choose a more focused audience to write for?
Publishing daily is making me realize my audience definition is incredibly insufficient, which is eating at me productively. Do you have resources for helping get focus around this? (timestamp: 58m11s)

Can I include both business and personal results on a sales page?
Do you have ideas about what “desirable results” to list for advertising my “Simple-Illustration-for-Business” course? Apart from the obvious, like not having to pay for illustrations. I have a hunch that they secretly want to be artists, and the “business” part is more of an excuse. (timestamp: 71m50s)

How do I get booked as a guest on podcasts that my target market listens to?
How do you approach other podcasts to get interviewed? (timestamp: 80m0s)

How do you capture ad organize your ideas for a daily mailing list?
I started emailing daily this week. So far, it’s been a lot of fun! I have tons of ideas and jot them down on all sorts of places, but I feel like it quickly gets disorganized. How you manage all your drafts/ideas/brainstorms? I am eager to learn some of your best practices in daily emailing. Can you please share some general tips or words of wisdom on this? (timestamp: 4m36s)

What should I do if a buyer leaves the client company before approving my proposal?
What happens if a buyer is forced to walk out on a proposal due to reasons beyond your control? I had a proposal sent and then an event caused my buyer to need to take leave (of unknown length). In our first meeting, the CEO was present, but the proposal wasn’t geared for them. Is it worth trying to salvage the proposal with new Why conversations with the CEO? The person taking my buyer’s place lacks context and doesn’t have the same level of authority. (timestamp: 12m35s)

How should I respond to a CEO who wants me to step into an interim executive leadership position?
I just delivered one of my productized services to a new client in Poland. They’re happy and want more. I spoke with the CEO who asked: Can you be our interim Head of Product Marketing? He wants me “to work with his team to execute on a range of (still undefined) deliverables.” How would you go about this making the offer? I don’t want to revert to hourly billing. Already starting to think of the 3 options - but without deliverables it’s hard to scope… (timestamp: 15m25s)

How can I get better at spending time daily ON my business instead of IN my business?
Speaking of where thoughts come from, I work Mon-Fri, but not equally well. My most insightful thoughts about my own business don’t occur to me until Thursday. As a longtime solopreneur consultant, any tips on how to get motivated and think better all week long? #ThursdaySyndrome (timestamp: 26m32s)

How do project oversight retainers work?
Can you say more about project oversight retainers? Who is best suited to offer them? Where do they fall price-wise in a list of proposal options, vs. other retainers? When is it a bad idea to offer one? (timestamp: 32m34s)

What are the pros and cons of switching from a “buy once, own forever” infoproduct/course model to an “all you can eat” subscription model?
The current business model for my JavaScript education business is “buy once, own forever.” I’m considering moving to a subscription-based model, where for a monthly or annual fee, students can access all of my courses as often as they want. I can elaborate on the business drivers behind that if desired, but I’m wondering if you (or anyone you know) has made a similar transition, and what kinds of things I should be aware of or thinking about that might not be obvious to me? (timestamp: 43m11s)

What products or services have you stopped offering over the years?
You mentioned you might do a course on daily emails (sign me up). This made me wonder: what other successful courses, services or products have you offered in the past that you no longer offer? Some of your successful early steps might be worth trying for us newbies too. (timestamp: 52m5s)

How do I politely push back on “out of scope” requests from a good client?
I have a resonable client that has suggested some changes during our (value priced) project, that’s beyond our current focus. (Ex. design updates to an area we agreed to leave as-is.) I think gently reminding them it can be left for a future phase / it’s not our focus will suffice, but can you talk about strategies for having this conversation effectively? Thanks! (timestamp: 56m9s)

Should I trade in my M-F whale client for a W2 full time job to make space to build my authority?
In a recent TBOA, you and Rochelle described one of the “edge cases” for folks that might still bill by time-and-materials that describes me well: making a tidy living billing for time (day rate, not hourly, but still), zero market presence, but working my ass off. My current arrangement really only holds up with an almost full-time commitment. I’m torn: do I put in the added time as things stand to build authority in the market, or take a W2 in the meantime to make the space to do so? (timestamp: 63m16s)

Will offering a product with slightly different positioning compromise my overall positioning?
I have worked hard to get my positioning right - selling „brand clarity“ instead of „illustration“ in my 1:1 service. Now I’m focusing on my courses. I notice that it is much easier to sell “Simple illustration for business“ course. That’s what people want when they see my drawings. „Brand storyboarding“ is harder to teach, and harder to communicate. I love both topics. But would focusing on “simple illustration” compromise my Big Idea - if I still offer Brand storyboarding 1:1? (timestamp: 73m7s)

How much should I worry about picking a business name if I might want to sell it in the future?
How much importance should you place on building a business with the aim of selling it, or exiting at a certain point – especially if you’re a soloist? I’ve heard you say previously that what you name your business doesn’t really matter, but if you’d like to sell it later wouldn’t its name have an impact? Especially if it was tied to your own name? Or is this not a concern for a soloist as your business is nothing without you anyway? (timestamp: 77m43s)

How do I come up with two additional options for a proposal when the prospect has requested a specific scope of work?
I am a big fan of the proposal template. I struggle though when clients ask for a specific engagement scope. I find that I can convert the requested scope into option 1 and then add elements for options 2 and 3. Problem then is that pricing for option 1 is no longer a “no brainer” and I am losing deals. I am working on having online, self serve options to include in a less expensive option 1 going forward but I am not there yet. Thoughts? (timestamp: 87m18s)

I suspect that my pricing might be scaring clients away... what should I do?
Connected to my prior question...starting to wonder if my pricing is too high...I struggle to bring the why question to a tangible number to represent value even though all the work I do is highly strategic. How should I evaluate that? (timestamp: 93m48s)

How can I create a system that keeps me consistently building content for my business?
At this point, you have a system that works for keeping consistent in building content and gardening your business. What was the path to get there? What approaches didn’t work, or misled you along the way? (Worried I might be caught in one myself) (timestamp: 100m8s)

How did you transition from development to consulting to coaching?
What was your journey like going from working in software development to consulting and then coaching? I’m interested in taking a similar path as you, but find myself in the first stage here, with much more implementation work than consulting. I’d ultimately love to end up in a coaching role in 10 years or so. Were these transitions actively planned, or was your experience more serendipitous? Thanks! (timestamp: 3m16s)

How do I find clients who value beautiful work?
The measuring beauty email got me. I try to do design work that is both effective and beautiful. Business experts tell me that I might value beauty -- but my clients don’t. I’d love to interview some clients about the additional premium value of beauty. Can you suggest some specific questions I could ask them? (timestamp: 10m2s)

Should I have more than one positioning statement?
Should I have more than one positioning statement? Like: (1) a core LFPS on a post-it on my monitor just for me (2) an XY based on that to put on my home page (3) a couple variations on that XY for different sales pages (4) a “simple English” version for everyday conversation (From a Slack conversation just now) (timestamp: 20m56s)

How do I find non-profits with the most money?
Nonprofits are a dream client for many solopreneurs. If maximum price = ( BUYING POWER * DESIRE ) / AVAILABLE OPTIONS, what are a few ways to figure out which nonprofit clients have the most buying power? (Sorry I can’t watch live!) (timestamp: 27m8s)

How can I make my market research offer more compelling?
From slack: What to do when your ideal clients aren’t responsive to your research outreach and you know this is because your offer isn’t compelling enough? My ideal clients are seed-stage, startup founders who are extremely strapped for time. They need to perceive the exchange as valuable. How to know what they would find valuable? I’m reluctant to share/produce content based solely on my own assumptions of what they might want, but what are my options? Feels like a chicken & egg situation (timestamp: 37m42s)

How does daily writing improve your thinking?
Last week you said that writing daily improves your thinking. Can you offer an example? Maybe where you had an idea or opinion that, through the course of writing about it (and maybe getting feedback from readers) that your position evolved? (timestamp: 49m29s)

Is there any value to a strategy engagement if my client doesn’t follow through on it?
I’m drafting my first proposal to a CMO to increase developer adoption. Their positioning is close but need clarity to get best-fit leads. I feel confident I could assess and deliver insights they could use to take action themselves (hire an expert, DIY, etc.). Struggling with value mindset: How should I think about the value of giving them that clarity without a guarantee they’ll take action? How would you lay out options? It feels “half done” without them actually implementing the advice. (timestamp: 58m22s)

What steps did you take to create this membership community?
Can you please share more about your process with creating this paid membership community? Especially the early days from scratch. I’d like to replicate similar with a in-house junior to mid-level marketer audience. (timestamp: 66m39s)

Should I get a lawyer or is something like LegalZoom good enough?
What advice would you have on finding a good lawyer, beyond just hiring someone in your state? What are the 3 biggest benefits you have received from working with one? I believe you had mentioned working with a lawyer to go through the process of registering as a business. Plenty of services allow you to do this without one (ie. LegalZoom). Would you still recommend doing this with a lawyer? Why/why not? (timestamp: 71m44s)

Is there an interplay between ditching hourly and one’s self-worth?
Some great questions today and they’ve inspired me to ask this one. How is ditching hourly related not just to monetary wealth but self worth? Can it be an attitude more than just a pricing strategy? (timestamp: 79m40s)

How might a strategy engagement be broken up into tiers?
A warm prospective client (very large housing association) would like me to submit a proposal to write a strategy report on the future of their widespread CCTV video surveillance. Of course, I’d like to offer three widely-spaced options. How might a Strategy assignment be laid out as three nicely differing options? (timestamp: 86m28s)

How many hours per week should I spend on marketing?
How many hours per week should I spend on client work, versus hours spent on marketing (emailing/ podcasting)? (timestamp: 6m51s)

How can I explain the benefit of paid discovery projects to new clients?
Enjoyed your recent episode with Alex Hillman on paid discovery projects. Two questions: If the client is not aware that they need help to clarify their vision, and they are not as readily able to admit it as Alex was, how do you know that they still stand to benefit? How to even articulate that to them, nevermind the benefits, especially if they need to convince someone else (it happens, even the top dog has to answer to someone) ? (timestamp: 10m39s)

What should I do to launch a new productized service I’ve created?
Any advice on how to launch a productized service? Assuming that I have the sales page, lead magnet, and nurture campaign setup. How should I announce the new service on LinkedIn and my mailing list? In case it’s relevant, the productized service is a 2-3 week engagement to create a strategic plan for solving a common challenge in my niche. (timestamp: 16m57s)

Does daily emailing improve revenue?
Does daily emailing improve revenue? Emailing daily is intimidating. Does it definitely increase a solopreneur’s earnings (as opposed to weekly)? Or is it more about something else? Have you manually emailed every day for years, no automation? (timestamp: 23m28s)

What can cause a drop in leads?
What can cause a drop in leads? Someone in Slack noticed a drop in new leads that she couldn’t explain. Scary. Did you ever notice an unexpected decline in leads or revenues? What caused it? What did you do to fix it? (timestamp: 29m21s)

How should I approach the WHY conversation with a large multinational company?
I’m having a hard time identifying the actual value when having the WHY conversation with a prospective client. They book a 20-min introductory slot on my website and then tell me about the problems they face. They are mostly large multinationals. When I ask them about “what value this project would pose to you”, they either don’t want to share a $ figure (no NDA) or haven’t thought about the actual value they hope to get from a consultant. How should I approach the WHY conversation in this case? (timestamp: 34m11s)

How can I start reaching CEOs instead of director level buyers?
What’s your best advice for consultants to reach more senior stakeholders with their marketing? In my experience, CEOs / VPs have limited time budgets to read blog posts/ listen to podcasts. They also tend to have limited understanding of the subject matter (in my case ecommerce) and often let their Directors search for consultants. Do you have any advice on how to “climb up” the marketing ladder to reach more senior stakeholders? (timestamp: 45m31s)

How can I establish credibility selling a new service to a new market?
I’m considering a pivot away from serving the financial industry as a designer/copywriter. I want to be more on the strategy (head) side instead of the hands side and I’ve completely lost interest/faith in this industry. Still going through the process of what audience to now serve, but once I do that, what are some good methods for establishing credibility in a new market, especially since I don’t have social proof from people in this new group. Thank you! (timestamp: 51m56s)

What should I pay attention to while delivering my first big value priced project?
I am starting a 4+ month long project in a few weeks. First big ticket VBP client. I am still new to VBP and transitioning from hourly billing, but I already know in the future it may be better to sell this in smaller chunks. I didn’t have the know how to be able to do that this time around. What are some specific things I can do during/after this project, on my own and with the client to learn and set myself up for success later? What else can I do besides keep a log of all of my activities? (timestamp: 57m50s)

How do I figure out my positioning once I have chosen a clear target market?
I have a rough client profile with specific traits/characteristics (women, product leaders, impact-focused), and two industries that I know today I like to serve (healthcare and climate change). I am addressing one problem: the lack of worthwhile UX and product development knowledge/processes specifically for launching b2b products. I simply can’t figure out what my market positioning would be (vertical, horizontal, or some combination of both) with the above. Do I need to keep drilling down? (timestamp: 65m3s)

What are some tips for conducting The Why Conversation in-person?
Best, practical tips for “in-person” why conversations? (timestamp: 70m5s)

What results should I expect from guesting on someone else’s podcast?
When you guest on someone else’s podcast, what is the typical direct result afterwards, in terms of increase in email list signups or product purchases? (timestamp: 73m26s)

What’s the best way to get pricing guidance for a new productized service from beta clients?
What’s the best approach to find out how much a client would pay for a future productised service? I’ve almost finished running three clients through a new service I’m testing, so the next step would be to ask them what I should charge others for it. Is it as simple as saying, “Hey, what would you pay for that?” or is there a better approach here to get more useful feedback in general? I was also planning on using your perfect testimonial template. (timestamp: 76m50s)

What should I do when I’m not the best option for a prospect?
Sometimes when I am unavailable for a project or when I client budget is too low they ask if I know anyone else who can work [with their time frame or budget] -- How do you manage a list like this? Should it be a long list? Should I ask the masses for their portfolios/prices and curate it on my own? Do I spend time on this at all? TY (timestamp: 81m8s)

Should I pivot away from a new target market that I’m not loving?
I know that you say that you should give 3-6+ months targeting a niche, however I’m feeling an early pivot coming on. I’m not sure I like the target market enough to bother. Pull the ripcord after 4 months with 1 client or give it another go? Try to find another client harder? Have more conversations? (timestamp: 84m47s)

Could you help me narrow down my niche?
Hello everyone! Could you help me narrow down my niche/target? I work exclusively in the Quebec market so I already feel like I’m pigeonholing myself. ;) My main services are 1) Marketing consultation 2) Marketing strategy and plan 3) Brand messaging 4)Website copy. And I’m currently targeting “experts” which seems way too broad. My shortlist of ideas now include: environmental/animal loving brands, startups, or innovative founders. (timestamp: 4m10s)

You recommend focus, but does that mean NOT having multiple income streams?
Today you recommended “Publish as often as humanly possible”, “Have a laser focused ‘sun’ in your content solar system”. I hear that most wealthy people have multiple streams of income. Do you recommend not trying to maintain multiple streams? Is that just too difficult when doing things your way? What do you see with your successful clients - do they have multiple streams? If so, how do they manage to laser focus on each? Asking because I have 2 streams, I like the hedge, and want more. (timestamp: 17m52s)

Do I need to niche down on a target market?
I’m curious about your thoughts on this topic: Niching down My value niche: I help my clients get Software Products actually delivered and retain Engineers Do I need to niche down on a target market? There is this nudging thought that I really need this to do effective marketing, to provide more value etc. Sure, my service is from higher (monetary) value to Enterprises than to SME where a crippling software project may cause dramatic damage to their business and reputation. (timestamp: 22m55s)

Would adding a paid call to my service offerings act as an authority signal?
I’ve started a weekly podcast, I’m committing more attention to my newsletter, already have a few freebies and this week I’m launching a free email course. I will roadtest this content with my current client and will use these tools to engage with other (large) clients. No products yet. Thinking about a paid call. Question is can that act as an ’authority signal’? (timestamp: 32m11s)

How do you handle the fear that comes with publishing your ideas?
Re: punk marketing I find myself struggling with thoughts like “oh boy, that’s so obvious, you’ll be perceived as an idiot if you decide writing about it” and that’s where I flinch and stop. How do you and others cope with that? So basically hindering myself from becoming an authority by not publishing all the drafts I have on shelf. Best Erik (timestamp: 35m59s)

How do I prove the value of market research to my clients?
I’m in the market research space. How do I calculate value-based pricing and ’prove’ ROI to a company I’m pursuing? (timestamp: 42m5s)

Should I continue publishing my content in three languages?
RE: Punk Marketing: I have been writing content in three languages (English, Dutch, and German) for the past few months. I feel that having to write and translate in multiple languages creates friction. It makes posting things daily almost impossible. What questions should I ask myself to decide which language(s) to publish in? (timestamp: 52m8s)

Should I accept other types of clients from my ideal buyer’s industry?
For the last few years, I have positioned myself as a consultant that helps sheet metal companies increase productivity by automating processes. Lately, manufacturers of machines, robots, and software makers have been contacting me about my industry knowledge and expertise. They seem to have good budgets and interesting projects. Should I change my positioning to both parties? If so, would you split the positioning? Or just position as an industry expert (more solely on a vertical)? (timestamp: 54m26s)

What should I do after an advisory retainer ends?
After finishing up an advisory engagement, what should be the things I do for myself and the client? (timestamp: 8m53s)

How do I know whether I’m working enough if I don’t track my hours?
What tips do you have for achieving a healthy work/life balance? I’ve always tracked my hours to ensure that I get enough time at my desk, but it feels counter-intuitive if I want to move away from hourly billing. What tips/tricks do you have for making sure you put in enough effort without overworking and burning out? (timestamp: 15m8s)

How does The Why Conversation square with Chris Voss‘ assertion that asking “why” makes people defensive?
IIRC, you have also read Chris Voss, Never Split the Difference. He says “why” is accusatory, so only asks it when he wants people to be defensive. Otherwise, he asks “what” & “how” to get expansive answers. Does/can this work better in The Why Conversation? (timestamp: 27m18s)

Should I write a proposal now for a project that I can’t start for a couple months?
I have an existing client with a new project I think is worth doing, who’d like to work specifically with me, but I don’t have availability for a couple of months. Would you write a proposal now, with a farther-out start date? Or simply stay in touch, and defer writing the proposal? I realize this should be a good situation, since they have said they only want to do this work with me, but I know I need more practice at telling clients there is a wait to work. Thanks! (timestamp: 32m50s)

What would you say my big idea is?
I want to clarify my Big Idea. I do Brand Storyboarding sessions= „Brand Clarity through visual thinking“ Now I’m concentrating more on my classes that are all revolving around „illustrate your business“ e.g. „Drawing on social media“, or „Find your message“. What is my big idea? Drawing is good for your business? Brand building for visual thinkers? Is this too broad? (timestamp: 40m4s)

What can I do if I over commit to client work?
I am building two proposals, both for ~3-4 month long MVP projects for two clients who know I am the right person for the project (chances of them hiring me is high). I am still working as an employee ~30hrs per week with my current company. I usually am able to take on one project with no difficulty balancing between my day job and my project work. How do I know if I am taking on too much by accepting both projects while still being in my day job? (timestamp: 48m58s)

How can I protect my course IP so students can’t steal it?
I’ve been working on grow my authority engine -- been featured on some podcasts. I’m writing a book and working on workshop material. A listener from a show reached out and wants to be in the workshop as an early student, but mentioned they are looking to build their own course. How should I go about protecting my IP and making sure students/mentees don’t turn around and try to repackage my course material? Should I have legalese around my workshop IP? (timestamp: 53m51s)

How long does it take to go from zero to $250k with a solo authority business?
After starting a solo authority business from scratch, how many years does it take realistically before you are netting a good income (say $250,000 a year in a big city)? Background: I am the same age as you, and I want to transition from firm owner to soloist. But I don’t have 10 years to wait — or another 10 years to recover if it fails. Do I have time to make the leap? (Extra credit: how can I be sure it will work?) [Sorry I can’t be on the call live, eager to watch the replay!] (timestamp: 1m56s)

What should I do after beta testing a service with a new client?
What next steps would you suggest after beta-testing a service with a new client? I’ve been providing pro-bono consulting/implementation work for clients in a new niche. I am almost at the point where I’m ready to start thinking about what comes next (e.g., pricing, new website, productising). I’m also going through TPS9 now, so maybe there’s some crossover to come here. Thanks! (timestamp: 6m54s)

What is the thinking behind your various pricing models?
You said recently that there is science behind the “magic numbers” in value-based pricing models like Goldilocks, Might-As-Well, and Plus-85. Can you say more about where those numbers come from, or suggest additional reading? Eg., why is the Goldilocks middle 2.2x? I really want to use those big numbers, but knowing where they came from would give me a big confidence boost! (timestamp: 10m51s)

Should I host my podcast on my main domain or a different one?
Hey J, could you talk about the reason why you decided to promote your podcast on an entirely different domain and not add it on your main website? I recorded a couple of episodes with guests, and I’m deciding where I should promote my show besides on Spotify, Apple, Google, etc. (timestamp: 21m41s)

How much “hands on” work can I include in an advisory retainer?
Is there a smart way to do a retainer that includes some hands-on work? Examples could be writing a report, adding some metrics to a PowerBI, writing a script to mass update some data (for me to run one-time; not to put into production). My ’old’ retainers were hourly based. So it didn’t matter if I was thinking or doing. I just don’t think I’m at a place yet where I’m advising on things that the client is able to ’do’ on their own. I hope that makes sense. (timestamp: 26m25s)

Will my new focus hurt my follower count on social media?
Have other students expressed concern that, as they build their audience on social media (say, LinkedIn) and they focus their content on value for their ideal buyers - it won’t be relevant for the majority of their followers? Over time, new followers will be closer to our ecosystem of prospects and related experts ... but how about early on? Something to even worry about? (timestamp: 35m39s)

How do I keep the lights on while trying to attract my ideal buyers?
I recently completed my first VBP engagement and can’t seem to bring myself to apply to jobs like I used to. I have been working on my website/positioning so that it is at least in the short term somewhere between where I was and where I want to be, but it’s definitely a long game to update my public profile and farm those “ideal clients”. This takes time and I still need to pay the bills. Is the only way to fully transition to keep hedging on both fronts for X amount of time? (timestamp: 40m6s)

What should I do if I’m attracting low quality leads?
Would you recommend putting a few questions on your booking page, so that clients can provide info ahead of the initial call? I got a lead through a “low commodity” freelancer job board and I wonder if it makes sense to introduce some questions to give them a sense of what it’s like working with me. But maybe this can be better achieved on the call itself. I think my fear is stemming from the poor quality of the job site, and wanting to present as a high-value consultant. Thoughts? (timestamp: 44m24s)

What can I include in my retainers beyond advising a single contact?
You generally recommend a focused advisory retainer definition (e.g., available to one person in org. for consultation). Under what circumstances (if any) would you allow your primary point of contact to pull you into an occasional broader discussion with their team? For example, I’ve heard you mention occasional travel on-site for your past advisory clients. Was this under the retainer or an engagement they added on? (timestamp: 47m20s)

Do you have any tips for recruiting a small team to help me on a client engagement?
My value based consulting ability to wow my star client is threatened by my ability to recruit my first sprint team. What tops do you for finding high quality tech & design leads in this super competitive employees market? (timestamp: 51m25s)

Could you provide feedback on our draft positioning statement?
We are shifting our software agency to support non-technical founders in the early stage. We would need a teardown for our positioning statement draft: We help non-technical founders to build their software product from zero to €5 Millions MRR. Unlike our competitors, we apply a fast-paced lean startup process to delight your early customers and absolutely thrill your investors. What‘s your opinion on that statement? (timestamp: 56m1s)

What tech do you use for hosting your podcast?
Followup on the podcast website question. What tech do you use for ditching hourly podcast site? I see a transistor integration but you said it’s not hosted there right - just for distribution? (timestamp: 60m14s)

Can I market to both CEOs and non-exec level employees?
I am mindful of the advice: “the altitude / door you enter an organization is how they will continually view you. It is difficult to gain altitude.” My strategic level advisory services are best suited for the CEO but domain-specific / tactical materials would be valuable for others in the organization. Would it make sense to push the latter into a membership environment so I can still market to non-executive customers and try to keep some separation between the two? (timestamp: 5m13s)

My clients only want to pay me for the shortest time possible. How do I sell longer contracts?
I offer advisory services structured around weekly meetings with support in between meetings. I am running into an issue where clients only want to hire me as short of a time as possible. This makes my engagements short and choppy and a very unpredictable. How do I sell longer contracts? I offer advising on a technical subject matter directly to engineers on the project. (timestamp: 10m56s)

What mindset shift has had the biggest impact on your business?
What mindset shifts have been the most impactful on your business and your coaching clients’ businesses? - other than not billing hourly :) (timestamp: 17m49s)

Have you ever considered doing a daily podcast?
Have you ever considered doing quick “microcast” audio recordings of your daily emails and handing them off to someone to clean up and push out onto a podcast feed? Thoughts on this as general idea? (timestamp: 26m59s)

What steps should we take to transition a 13 person agency from hourly billing to value pricing?
What step by step “Transition Path” shall we follow to transition a software agency from hourly to value based? Background: We plan, design and implement MVPs for SMBs and Startup, having a team of 8 developers, 2 designers and 3 consultant people. What challenges and risks do you see for the transition? Shall we push people in developer roles to move up to more strategic and consulting roles? (timestamp: 30m35s)

Should use The Why Conversation on lower value clients?
I could use more clarification on the why conversation. I know now that it’s really for much higher price points - say $30-$50K and up. I tend to sell quite a bit below that. How much of that initial why conversation should I salvage for a lower price point prospect i.e. do I leave out the “why me?” or just scrap the 3 why’s altogether? (timestamp: 43m56s)

Is it fair to sell an advisory retainer to a new client for less than an existing client is paying?
Does anyone use the 3 proposal options on consulting services? I’m meeting a client today who wants consulting. But I don’t think they would go for $10k/month. And honestly, a couple of weeks ago I wouldn’t have dreamed of suggesting it😂 But since I now have someone on an advisory retainer for $10k I feel it would be disingenuous to sell the same thing to a different client for less (maybe this is bad thinking?). Not that’s what has me thinking about lower levels. (timestamp: 55m43s)

What exactly does a roadmap consist of?
I’ve heard you talk a number of times (here and podcast) around offering a ‘roadmap’ service as an entry service. Do I get it right this is not more/less than a step by step overview of the steps they can/should take to realize their objective? (timestamp: 63m37s)

How can I get more clients like one I’m currently working with before I get a testimonial from them?
I’m in the middle of my first value-priced advisory engagement (yay) and I think I want to attract more of the a similar customer in a similar space. It’s too early to ask for a testimonial as I’ve not delivered quite yet. What could I do to promote my services right now to find my next client? (timestamp: 68m39s)

Do people outside of my target market need to understand my positioning statement?
Is it normal/acceptable to have two positioning statements? One for your web site, and one for social settings? Or does the feeling that I need two mean I haven’t achieved perfection yet? (timestamp: 75m18s)

What should I sell to a client after my initial project wraps up?
I am nearing the end of my first value-based project with a client. I am working on the final milestone with probably ~2 more weeks to go. I think my client and I both know that there is still a lot of work to be done, but we haven’t had any conversations yet with regards to whether they still need my expertise. Do you typically let clients come to you first with the request? Can you share different examples of how you’ve handled this in the past? I imagine it’s not a one size fits all approach. (timestamp: 3m5s)

Should I post prices on my website?
Some people tell me I should be putting the price for my services on my website - other advise strongly against it. I know you are pro-mentioning - but are there any circumstances where this works better than other? (timestamp: 15m31s)

How do I know if I picked the wrong niche?
I recently decided to niche down to work with early-stage B2B startup founders. The Founders that I work with tend to over-index on Product and don’t spend enough time building out their GTM strategy. I sometimes feel like what they really need is business coaching. There are some designers trying to fill this gap by offering value proposition workshops, etc, but I’m not sure whether that is something I want to offer. I don’t think this is the case here, but have I picked the wrong niche? (timestamp: 21m40s)

When should I start creating content for my business?
What resources would you recommend for folks who want to learn more about whether generating content is right for their business? I am early in my consulting journey and still learning what my clients pain points are. I don’t know whether I’d be able to generate a following since I am still growing my knowledge of both my niche (early-stage SaaS startups) and specialization (UX Design). Is generating content something you’d usually recommend doing once you’ve reached “expert” status? (timestamp: 30m41s)

How might I pivot a prospect from considering me for a project instead to an advisory retainer?
This is a followup to a slack question about a ‘whale prospect’. (I hope you remember it) After thinking about it, I’m not sure I WANT the project. BUT . . . since I know more than anything about building software around this inventory system, I would LOVE to leverage that for an Advisory Retainer. How could I reframe the conversation to position myself as a valuable advisor instead of offering him our product? (timestamp: 37m14s)

What should I wear to look more like a consultant?
Hi Jonathan, it’s exciting to join you all! I’ve long wondered about establishing ‘a look’ that is distinctive (in a good way). Years ago at an existing client’s Reception area wearing my ‘consultant’ blue suit & tie, and I realised the receptionist just treated me like any salesman who was honoured to be let into the building to try and sell them something. Ok, my ego at play here(!) but how might I appear as “wow, our consultant has arrived!” (Ok, joke, but I’d like to change it up). Thanks :) (timestamp: 47m53s)

How many 1:1 coaching program members should I be able to handle as a soloist?
My offer is training and ongoing 1:1 ad-hoc access for ‘star’ individuals. There is scope to replace the training by pre-filtering ‘stars’ into a high-fee structured 1:1 coaching programme. Looking for your perspective on how many people to onboard for that at any time, ensuring they have a valuable experience, some of these will want to continue with ad-hoc access afterwards. Ad-hoc access now runs at 6-8 people per quarter, that’s manageable. (timestamp: 56m22s)

What if my prospects don’t want the thing they actually need?
“Don’t try to sell something people don’t want” is the kind of solid advice that’s obvious once you hear it. What’s your take on “things people might want if they were aware of them, but not on their radar?” A specific e.g. might be a different lens on team process consulting. (Super-specific individual take is “repurposing the solution-focused brief therapy approach & mindset for business consulting”, which remains niche enough that I’m hesitant even to ask about it.) (timestamp: 67m25s)

I uncovered an expensive problem, but I’m not sure I’m interested in solving it... what should I do?
I’m currently having meetings with soloists in a new niche. After a few meetings, I’ve discovered that not having automated systems is a huge pain point. I already have a case study of solving this. But my current specialty and interests aren’t related to automation and more to design/marketing. Would you suggest going all-in on solving this pain point for as many people as possible? Or should I use this only as a segue into what I want to do (which they also express a need for)? (timestamp: 78m11s)

What should I do at the end of a paid coaching call?
I had my first paid consulting call recently, and want to improve a few things for next time. - I offered a money-back guarantee. Is the best way to check they are happy to do this casually at the end of the call? Or should I email after, or just let them bring it up if they aren’t? - Should I use the whole “Brain Audit” testimonial process, even for these short engagements? - Should I send that request immediately, when everything is fresh? Thanks! (timestamp: 11m23s)

How should I go about renegotiating a fixed price contract if I realize it’s going to take twice as long as estimated?
I am contracting with a small consulting firm on a series of 5-week projects. We agreed on a flat fee for each project, and estimated it would take about 42 hours total to complete each project. Unfortunately, the first project took nearly double the amount of time for me to complete. I want to re-visit our agreement for future projects. Curious how you would go about doing that? (timestamp: 18m5s)

At what point is it not worth swapping niches?
I’ve recently been working with a soloist for free while I test a theory, and I’ve gotten them some great results. I’m now looking to test this further with 2-3 more soloists to get case studies and testimonials. This soloist is in a very distinct niche (wedding celebrant), which is entirely different from the current niche I serve (higher education). What would you say are the pros/cons to working with soloists vs. larger institutions? At what point is it not worth swapping niches? (timestamp: 30m26s)

How formal should an agreement be between podcast co-hosts?
When you collaborate with someone else on a podcast (such as your approach with TBoA), do you try to define some kind of loose “ownership structure” and/or advance plans if the collaboration eventually ends. Most niche podcasts won’t be direct money making machines or acquired by Spotify. But there is some inherent value in the feed/subscribers if the hosts decide to go their separate ways someday. (timestamp: 40m21s)

How do you handle a week of vacation when you have active monthly retainer clients?
Given that you do a monthly flat fee for consulting services for a customer, how do you handle one week of vacation you want to take? (timestamp: 46m6s)

How to I keep scope creep within reason on a value priced project?
Talking about scope, I have trouble differentiating between deliverables vs. results delivered in terms of value-based pricing. In my mind, I’d do anything it would take to get the results delivered for our agreed upon price because it’s a true project as opposed to just mere deliverable delivery. Of course then, the scope can grow or shrink quite dramatically. (timestamp: 51m1s)

How would you value price an engagement that isn’t meant to deliver a financial outcome?
I had an engagement to help create a content platform for a purpose driven client, where I think I failed to nail the objective in a measurable way. I think the reason is that there is no money to be made but rather the founder is on a mission to help other saas startup founders avoid avoidable mistakes, in other words reduce their risk of failure. How would you approach uncovering a measurable metric from a client for whom it is a very emotional mission? (timestamp: 63m1s)

If I niche down on a specific industry, won’t clients worry about me working with their competitors?
Sometime ago you talked about making sure the niche we choose is likely to be willing recommend us to their peers and you said something about “plastic surgeons” being special about that could you elaborate on that ? Or do you have other examples of niches where a “satisfied” client would not want to share a successful engagement because of some “culture weirdness in their industry” ? (timestamp: 74m6s)

How should I handle price increases for clients on annual retainers?
I have an access retainer offering that often started with a 4 month retainer, and then converts to an additional annual retainer. The annual retainers priced at a discount as I know the client and get an annual commitment. I have a few of these entering renewal stage again. They will likely ask for a lesser access/ and or price. Meanwhile I have since increased my prices on the first 4 month retainer. I want to be careful of my clients - comparing my pricing. Any advice in that regard. (timestamp: 79m12s)

How can I keep my proposals from getting too long?
I’ve been using your proposal template and I feel like my documents are still super long. Any suggestions on being more succinct? (timestamp: 81m20s)

Can a soloist really make seven-figures per year?
I just noticed that the blurb for the Business of Authority podcast says “A weekly show for independent professionals who want to go from six-figures to seven while increasing their impact on the world.” Whoa, is a seven-figure annual net income really within reach for us? What percentage of your students achieve this? What stops those who don’t? (timestamp: 3m14s)

How should I set client expectations about my availability?
How do you answer questions from prospective clients about your availability/working style? I am thinking of adding a section called “How we will work together” in my proposal with a few bullets. I think clients want to know how available to them I will be during the project. Any advice to set yourself up for success here? (timestamp: 7m11s)

How should I structure post-project engagements for clients who want continued access to me?
How do you address questions from clients about what your availability will be like once the project is complete? I have heard this directly from clients. They are afraid to commit to retainers at the onset of a project but may want to “reevaluate” their commitment later on (because “they don’t know what they don’t know”). It’s obvious to me that my availability cannot be guaranteed. Do you have any additional advice? (timestamp: 12m26s)

How can I pivot to a new business that I don’t have experience in?
Before you were a business coach; you did mobile consulting. What gave you the confidence to decide you were going to become a business coach even though you didn’t have prior experience with it professionally? (timestamp: 16m25s)

How should I set prices if some of my clients have lots of money and others have very little?
What are your thoughts on sliding scales for different company/org types (say, community-based non-profit with a small budget vs. a deep-pocketed large corporation)? What approach do you recommend? (timestamp: 21m15s)

Should I accept some emergency “hands” work from a new client as a possible gateway to “brains” work in the future?
Today I had an intro call with a company that needs some help after a botched CRM implementation. They have a structured way to work forward now (after project failures) but they more need my hands right now to help fix things short term and then help with ’culture change’ later to prevent a repeat. A great ’in’ and possible future work. I don’t want to do hourly billing so a monthly retainer? How to prevent this becoming ’hourly billing by default’? Suggest say 2 months retainer then project? (timestamp: 27m1s)

What if a client chooses option 1 from my proposal but doesn’t understand the risk of such a low level of involvement?
With value-based conversations so focused on outcome as opposed to deliverables, how to handle when clients feel that choosing option 1 is still the best option, even if you know that it doesn’t necessarily help them to achieve their underlying business goal? How to know whether this is clear to the client before charging ahead with the project? In my case, I am past the proposal stage and this particular client has already opted for Option 1. Unclear if they know the risk they are taking on. (timestamp: 34m32s)

Should I worry about media release forms for podcast guests?
Media release forms seem way too formal for interview style podcasts. Do you do anything less formal along these lines when booking in a guest (particularly, one you don’t know as well)? Setting clear expectations about the process seems like it should be sufficient? At the end, would you ever send them the episode before it goes live? Thanks! (timestamp: 41m7s)

Why can’t creative agencies take on more than 10-25 clients?
I’ve heard a lot of consultants say a creative/marketing firm can only successfully handle so many clients at one time (regardless of firm size). Usually somewhere around 10-25 clients. Heaps of other professional services firms have far more clients (eg accountants, lawyers). Why is the cap on creative firms so low? (timestamp: 45m12s)

How do I build an authority brand?
How do I make myself an authority in a certain topic? What has worked best for your students or yourself? (timestamp: 49m38s)

Should I offer retainers to new clients? Or existing clients? Both?
As someone completely new to the idea of an advisory retainer but wanting to add it to my product/service ladder, how would I go about pitching one to a client? Would you suggest only offering these to new clients, or are existing clients an easier sell and better fit? Curious to hear your thoughts. (timestamp: 54m6s)

What tasks should never be outsourced?
What tasks would you suggest should never be outsourced? Would writing fall under this? Such as writing blog articles, social media posts, etc. (timestamp: 57m56s)

Should I drop clients as I add new ones or figure out how to scale up to meet increasing demand?
I’ve heard that I should structure my consultancy so that I get a client I provide a service 3-6 months clear objectives on my offering and that the service ends get my testimonial, get next client. Rinse and Repeat. But I’m now a year into my consultancy -- I’ve kept all my clients. I’ve now added 3 clients this month. I’m faced with the question(s) -- am I doing this wrong? Should i drop clients? Figure out how to scale? It’s okay to keep clients for long engagements (multi-year)? (timestamp: 62m30s)

How do I get practice with value pricing without putting myself out of business?
What did your initial ramp look like in terms of figuring out when to go value-based? Did you do a bunch of free work first? Right now, I’m getting the chicken-and-egg experience of not having a ton of exposure to the initial sales and scoping process, so don’t have an established reputation. (timestamp: 68m35s)

How should I share my new lead magnet with my target market?
I’ve just finished making a lead magnet and want to start sending it to connections on LinkedIn in my niche. What approach would you use here? My first thought was to send a link to the lead magnet and mention that I’m looking for feedback from experts like them. Although I’d like to send them a lead gen page, that seems too pushy for a cold connection. (timestamp: 7m6s)

How do you value price an outcome that can’t be measured in dollars?
How would you approach pricing services when the value you bring isn’t (or isn’t primarily) financial? I help organizations both design more equitably and produce more equitable outcomes. There can certainly be a business case for this (Google’s Product Inclusion lead wrote an entire book about it), but a lot of companies hire me/my peers for values-based and ethical reasons. (timestamp: 15m0s)

How do I find expensive problems to solve?
What is the best way to identify expensive problems a vertical or demographic faces? I am trying to decommoditize my dev shop and specialize is solving one specific hard and expensive problem but having issues identifying which vertical to go after and how to identify and scope a problem. Thanks (timestamp: 27m54s)

How might value pricing pertain to employee compensation?
We mostly think about value pricing from the client perspective, but what about from the employee’s perspective? Can we apply value pricing principles to employee compensation, workload, benefits (such as paid time off), and if so, should we? Can we instill the value mindset in our employees by example (the way we compensate and treat them)? (timestamp: 41m23s)

Should I publish the prices for my productized services publicly?
I want to offer some productized services (paid pick-my-brain calls, training, monthly advisory service, etc.). I wonder if I should publish the prices for these services on my website. None of the other companies that work in my niche do this. I still sometimes get (hourly) work through an agency and I’m not sure if publishing prices could disturb my relationship with them somehow. (timestamp: 51m20s)

Should we choose one offering to market or run simultaneous campaigns?
How to choose the right product out of your mix to maret? We have a small but engaged list (1k or so) with high open rates and conversions around 3.5-4%. We offer a membership, a self paced video programme and a “power hour” plus consulting gigs but growth is slow and it’s getting difficult to know which marketing lever to pull. Should we run simultaneous campaigns in parallel or is that only going to confuse things? Thanks! (timestamp: 56m43s)

How did you come up with your 85% multiplier for two-option proposals?
For your x1.85 pricing strategy, how did you come up with 85%? Should this multiplier be different for fields with more/less risk? If so, can you suggest a strategy for selecting a suitable multiplier? For context, I work on machine learning projects which do tend to have a larger uncertainty for the implementation time and level of success of the resulting algorithm compared to other software projects. (timestamp: 63m19s)

Would having a weekly topic help me with writing daily emails?
Do you have any suggestions on how you can talk about one weekly theme from different angles in your daily newsletter? How do you handle that part of content creation? For example, are 5 emails stand-alone subtopis of a weekly theme, or is it a continuous thing? I’m struggling to see how to structure and expand one idea to a week worth of content for my daily list without a “system”. (timestamp: 77m45s)

What if a client cancels a project after the initial phase?
Using your proposal template, do you ever give folks the option to stop work after the advisory phase if their needs have changed? Do you include an early term fee, or just bake it in and not worry about it? I know they’re supposed to pay up front but my gut is they’re going to want to spread it out. (timestamp: 84m50s)

How should I reconnect with busy C-level contacts in my network?
One area I’d love some help is this: Anecdotes/examples that worked for you to reconnect with C-level contacts in your network and open a helpful conversation (about solving their most valuable problems). Context: for me that’s Founders/CEOs of B2B SaaS Scaleups (+1M - 5M) - i.e. pretty busy people. (timestamp: 3m20s)

What are some good daily email lists I can use for inspiration?
Who are the best writers of daily emails not named Seth Godin or Jonathan Stark that a soon-to-be-daily-emailer should subscribe to for inspiration? (Can’t make the live session, but will be listening to the recording.) (timestamp: 10m17s)

What is your process for getting approval to put client logos on your site?
Do you have a recommended process for getting permission to use well-known clients’ logos? This would be for something like your “Brands I have worked with” section on your old site. In one case, my contact might still give me a testimonial, but is at a new company now. Going forward, it would be interesting to know if you suggest getting explicit permission for this along with the testimonial questions. Thanks! (timestamp: 16m58s)

Should I pay my contractors hourly or on an outcome-basis?
I currently have 2 contractors working with me who are compensated on a hourly basis. I am just about to add a third. I have the option to pay hourly again albeit at a higher rate. I am considering paying the new contractor by the project instead. Any thoughts on how to structure outcome-based contractor payments? (timestamp: 27m27s)

Do I need a framework to build my authority?
Do you think it’s necessary to have a “framework” to build your authority on a topic, or is a content solar system (or whatever you call it) enough? Framework meaning something like “I’ll help you using my proprietary SNAP method” S=sales, N=notice, etc… (timestamp: 42m35s)

How do I balance the relationships when an agency brings me to work directly with a client?
An agency initially approached me for pure “hands work.” Using some of your advice (thanks!), they now want something more advisory instead, and are actually introducing me directly to their end client. Any general suggestions for successfully balancing this scenario? Ex. If an agency approached you for mobile consulting, did you ever end up working directly for the end client, with the agency still involved? (timestamp: 53m8s)

Is sending an NPS survey a good thing to do after a project is complete?
Is it important to do post project surveys to generate an NPS score for the company? (timestamp: 68m41s)

Does it make sense to put logos of former employers on my site?
Following on from the question about showing logos on your site…would it make sense for me to put former employer logos on my site? (Microsoft, GoDaddy, T-Mobile) I did web/UX/sales funnel work for those companies and that’s basically what I do now too but for solopreneur coaches launching their courses. (timestamp: 70m21s)

Should I send my email list messages from my regular email domain?
As your daily email list has grown, have you run into any major issues with you people flagging your address/domain as spam and creating issues with spam filters? (Even though you have pretty obvious/ethical practices in place, people don’t always remember signing up – or act rationally in general.) Is using a separate domain variation for the email newsletter to avoid risk of 1:1 emails to important clients hitting spam filters something that is worth worrying about? (timestamp: 3m4s)

How do you know when you reach “expert” status?
How do you know when you are “expert enough” to start establishing yourself as an authority? (timestamp: 9m56s)

How could I transition a live event series into a podcast format?
Any suggestions for transitioning a live event series into a podcast? For years, I’ve run a free speaker series meetup for my niche. It’s been on hold since the pandemic started, so I’m considering making it an interview-style podcast instead. I’m think the upside of the existing event’s credibility and audience, outweighs the flexibility that might come with starting fresh, but curious to hear what you think. Thanks! (timestamp: 16m19s)

What if I’m halfway through delivering a productized service and I realize it’s not going to work?
I’ve sold a new client a two-month productised service with a money-back guarantee, but have realised after a month that their website is a huge turn-off for their customers. They even admit it badly needs redesigning. They want to continue with the rest of the service, but I’m hesitant, as I don’t think it will provide them with good ROI because of their website. What would you do in this situation? (timestamp: 23m4s)

How much should I screen clients before I let them buy my productized service?
When offering productised services, can you rely on a screening process or details on your landing page to set correct expectations and weed out any bad fits? Or should you always be conscious to do this yourself when offering productised services, and not assume the client has self-diagnosed themselves into your service correctly? (This is a bit of a follow-on from my previous question) (timestamp: 30m39s)

What’s the ethical way to transition people who downloaded my freebie to my email list?
I’m starting a fresh email list with this business and contributed a free product ($50 tutorial video with coupon to get it free) to a bundle that an influencer friend created. Now I suddenly have 700 people tossed into convertkit, from my Gumroad delivery method. There was no double opt in so no express consent to join my email list. What would you do? Email and ask them if they want to consent? Or add them to newsletter with a thank you message and just start emailing? (And maybe add a link to unsubscribe just from the newsletter but stay on the list for product updates on that freebie course they got? (timestamp: 38m41s)

Should I use my name or a product name for my website domain?
Is it better to have your website be your name or something related to your product? Ex: ******* vs **** I ask because no one assumes the correct spelling of Crews. (timestamp: 45m38s)

How do you balance working on the business with working in the business?
How do you manage your time and projects? I now have multiple clients and want to also be producing content. What have you found helpful to stay on top of everything. What percent of the time is spent maintaining vs building new content? (timestamp: 51m29s)

How should I structure a new podcast that I’m planning to do with a co-host?
I am finally wrapping my head around getting a podcast going in 2022. I have found a cohost I would like to work with. I really like the cohost format and prefer it over the single host construct. Any thoughts on how to structure the podcast? I’m thinking in terms of topics, guest spots etc. Thanks. (timestamp: 59m33s)

Is it too restrictive to target a podcast at just women?
I feel like we could have compelling messaging for women who are thinking of leaving the corporate world and becoming independent. Is it too restrictive to target the podcast at women? Personally, I think the messaging would work just as well for men. (timestamp: 69m11s)

I can help any kind of business, so how do I figure out which niche to focus on?
I’m a developer who specializes in Mathematical Planning. I’m trying to figure out which niche to focus on though. What are some ways that I could find a potential market to find an underserved niche? I can help a lot of different companies but based on your shows it’s easier to focus on a particular problem. (timestamp: 3m51s)

How do I price new requests that come in near the end of a value priced project?
Let’s suppose we do value-based pricing for a website project. This website consists of 30 pages (just an example). A client comes back to us at the end or before the very end of the project and asks for additional five pages. These pages are not high-value pages but are needed. What’s the best way to charge for additional scope? Do we take an average price of a page on this particular page and multiple the price with the number of additional pages or... (timestamp: 11m53s)

Is niching on a problem domain a viable approach to positioning?
Is it possible to niche on a problem domain? Scheduling people for shifts would be an example. Companies across industries and at all scales face this problem. Is this niching approach viable or a difficult road? (timestamp: 19m39s)

What should I say when someone asks for a discount?
How do you politely say NO to clients who are asking for a discount? (timestamp: 26m40s)

How do I get my first subscribers to a brand new mailing list?
For someone going from zero (no existing list) to daily email, how terrible of an idea would it be to cross-post daily items to a place like LinkedIn (at least to start)? I get that it kind of undermines the incentive to subscribe, but I think it would be more motivating to know that the messages are being seen by at least some people in my network early on. (timestamp: 28m23s)

Should I use “starting at $X“ pricing on my website?
I listened to your recent podcast with Blair Enns about productized services. It sounded like he was very opposed to having prices on the website for productized services. What are your views on the pros and cons? What do you think about a middle ground approach like “Starting at $12,000” on the web? (timestamp: 38m9s)

How should I present my proposed prices for a project?
How you feel about presenting pricing for a project in a meeting (rather than in a written document)? I have a call with 3 sponsors that I work with at a particular client. One of the projects has evolved into a different, bigger engagement that needs to be repriced. I have a number in mind but prefer to send it through after the meeting. Thoughts? (timestamp: 48m24s)

What are the difference between horizontal and vertical positioning?
I am a business consultant focusing on helping small businesses improve their business processes and technology stack. I typically focus on creatives and professional across multiple industries. Is this a horizontal or vertical niche? Would you recommend further specializing? (timestamp: 57m10s)

How can I start offering services that use my brains instead of my hands?
How do you start to move from hands on work to higher level work when you don’t have a specific niche skill or authority to build on. For context I do Rails development, mostly as a solo, planning and building projects typically for internal business automation, timesheets, invoicing, project management etc. (timestamp: 64m0s)

How should I handle The Why Conversation when the client has multiple projects on the table?
How to approach the Why conversation when the braindump reveals there are in fact many related projects on the table of different sizes ranging from 1 month to 10 months+? Do you have a Why conversation before every project? The client knows their wishes will be tackled one at a time, no need to convince them to break it up. But the nag is that some projects are low risk “add these incremental features to the software”, and others are high-risk greenfield endeavors where R&D needs to occur. (timestamp: 1m38s)

How should I structure a monthly retainer for coaching a team of junior devs?
When offering programming coaching retainer, such as pair programming, how to limit the amount of time available per month? For advisory retainers I’ve seen your answer to this question: most business folks won’t monopolize you. But for a junior dev team, I could see them wanting to pair or receive help 2-4 hours a day every day! (Context: client is large non-tech firm with a fresh software product dev team, that needs CTO style direction) (timestamp: 13m38s)

What marketing activities give the best “bang for the buck” for someone just getting started?
Suppose you would be back at the beginning again... In what order would you start producing your marketing content? (blog post, newsletter, social media posts, your podcast episodes, etc.) When would you know you need to start adding new marketing channels? (timestamp: 23m28s)

How would you decide whether or not to accept an invitation to contribute a chapter to a book?
I have been approach by a client (who was once my coach 20+ years ago!) to contribute a chapter to a book she is compiling on “Building Coaching Cultures and Organizations”. I am reading The Authority Code and I know I have to start publishing. Wondering if this construct might be a good starting point? I am not feeling the “Hell Yes” for this opportunity but thought I would ask. (timestamp: 29m23s)

What should I do to generate leads while doing client work 40 hour per week?
I’ve taken on a freelance contract which I expect to take up 40 hours a week of my time for 6-12 months. What should I prioritize in terms of lead generation / business development to make sure I don’t get a drought when this finishes? The contract is flexible hours-wise so I’m not tied to strict 9-5 schedule. (timestamp: 34m36s)

Should I hire a digital marketing agency to help with my SEO?
I have been out on my own for 2 years. I am up significantly year over year from a revenue perspective. I have done little to no marketing beyond being on a podcast or two. I have not explored SEO and rarely to company posts through LinkedIn. I still have a steady stream of leads but would like to have a wider net of client options. I am pinged by Digital Marketing companies through LinkedIN on an almost daily basis. What are your thoughts about engaging a digital marketing company? (timestamp: 43m32s)

I have a client who is very slow to respond and it’s impeding progress... what should I do?
I have a fixed fee arrangement with a client across 3 initiatives. We have made varying degrees of progress on the initiatives based on client availability to engage. I have been billing on a monthly basis since signing the SOW in September. Last payment is in December. Work will need to continue into Jan/Feb of next year. How do I set the client at ease that they are paying monthly for work that has not been done yet? We have a project review coming up and I expect the question. (timestamp: 52m6s)

How should I follow up with great potential clients who can’t seem to pull the trigger?
I seem to be having a fair number of really strong initial meetings with clients/collaborators. I am curious about how to manage the follow up in a way that doesn’t seem pushy or desperate (which I am not). I know people are busy and this might just be the nature of the beast. I haven’t done the math but I suspect I am having a 3-4 out of 10 conversion rate for opportunities. (timestamp: 58m9s)

What should I say to a prospect who knows I’m working with one of their competitors?
I’m working with a client in the education space here in Scotland and seeing really good results. So I’m looking to reach out to similar businesses further south in England. But I don’t want it to end up looking like I’m working for competing companies. Is there some minimum distance, or locale, that you’d suggest staying aware of? And how could I leverage my success with my current client without it looking sketchy to new ones? (timestamp: 65m29s)

What can I do when the results of the Why Conversation are wishy-washy?
Separate from the why conversation, would you suggest (or caution against) doing research into the company to gauge indicators like revenue, employee count, etc. to inform pricing decision? Perhaps to use as an anchor during the why conversation or afterwards if the why conversation ended up wishy-washy. (timestamp: 71m34s)

How should I decide which geographic markets to target?
I’m an American based in France and today, I work with a mix of French, European and US clients. Casting a wide geographic net is becoming a barrier for more deliberate sales & marketing efforts (e.g. creating content/doing events in multiple languages & time zones, figuring out who to build relationships with, etc). What questions should I ask myself to decide on my geo markets? I’m currently looking into market readiness and sizing the market opportunity. Thanks! (timestamp: 2m11s)

What should I do with my clients if I can’t service them anymore?
I currently live in the UK and most of my clients are UK or Europe based. In 3-4 years, I’ll be moving back to New Zealand, but I’m not sure what to do about all my clients (it’s mainly the time difference I’m concerned about). I’m a soloist with a handful of freelancers I work with on projects. Is there anything you would suggest putting in motion now to prepare (e.g., training someone to manage my client accounts, trying to find new clients for when I move, etc.) (timestamp: 12m13s)

Should I hire a business coach?
How do you know it’s the right time to hire a business coach? (timestamp: 25m9s)

Should an e-book be more generalized or specialized?
When writing an e-book as a tool, how much do you worry about how applicable your guiding principles are? The more it needs to fit everybody, the more generalized it gets and the less useful. And there are so many caveats and “it depends.” I do fundraising events and there are a lot of behind the scenes strategies, as well as tactical steps. Should I do a general book with a more detailed companion “handbook”? (timestamp: 28m41s)

We service three types of clients. How do I pick the best one to niche down on?
I run a small 3d architectural visualization studio, our clients are architects, interior designers and property developers. Let’s assume that my positioning is laser-focused, what would be the best lead generation system for this type of prospects? (timestamp: 36m4s)

How should I price building an application based on a prototype I created previously?
Pre-pandemic, I helped a client answer their immediate questions with a prototype. Now, they have a stronger business case to justify building the full project. Beyond the Why conversation results, any extra suggestions for pricing for a client like this, with some existing expectations? I appreciate that “start with new clients” is probably the best answer here, but this would be useful for the one or two that fit my positioning really well still. Thanks! (timestamp: 43m1s)

What goes into writing a good email course?
Been thinking about building an info-product course. I found your email-course funnel the ditching-hourly massively helpful, what actually captured me. Curious if you could talk about the email-course strategy and any lessons learned/tips. (timestamp: 61m22s)

Should I start a non-profit as marketing for my for-profit LLC?
People in my target market often feel good about working with/through non-profit organizations. I am considering starting a 501(c)(3) company, separate from my for-profit LLC, in order to fiscally sponsor and obtain grants for volunteer work that align well with the “sun of my content solar system”, so to speak, that is, as part of my marketing efforts. Is this a terrible idea? (timestamp: 69m9s)

How long should The Why Conversation be?
I’m in the middle of an extensive “Why Conversation” with a new client (that is mine if I want it, no direct competition). At this point, I’ve had four meetings and 6-7 hours total. Is this overkill? I’m drilling down more on outcomes and scope each step of the way. Ideally, I’d want to do even more upfront analysis before guaranteeing for them what I can do... (timestamp: 74m0s)

One of my competitors offered to pay me to train them. Should I do it?
What do you think about us specialists training or even partnering with generalist ‘peers’ (agencies, consulting firms) on our niche? While I don’t think these generalists could rival me in expertise after just a few trainings, my gut tells me it’s risky to give away ‘trade secrets’ to competitors who may co-opt my materials/approach (even if they do it less well) and go after my potential customers while cutting me out of the equation. Am I overthinking this or is this an actual risk? (timestamp: 2m27s)

How do I find a central theme for my content?
I’m struggling to find a central theme for marketing. I’m running workshops mostly for startup teams, for different type of problems and goals e.g. product validation, product strategy or company strategy and what would be a centre of my Solar System. (timestamp: 18m55s)

What should I point my paid ads at?
I currently run paid traffic to a productised service that costs around £1500, but don’t get any interest. I have a couple of clients on this service, so I know its valuable to my niche, but neither were reached via paid ads. Would it be a good idea to run paid traffic to a lower commitment offer/lead magnet that builds towards the productised service, or what would be your approach? (timestamp: 30m50s)

How do I quickly find good watering holes?
How can I rapidly distinguish between watering holes / channels / conferences / forums where my ideal buyers express pains versus places where most activity is marketing or presentation of projects/solutions? I seek the former and keep finding myself in the latter. (timestamp: 39m3s)

Is it ever a bad idea to offer a guarantee?
I sometimes feel like the “money back guarantee” is very sale-sy - almost cheesy. I know you use it a lot...and recommend it. Can you talk more about why you like it so much? (timestamp: 45m6s)

How should I package and price an online training course?
Hi Jonathan. Do you have any advice on how to price online training courses? I am in the planning stage...thinking through how I might package up and offer Design Thinking training in a series of modules. Do you have thoughts on pricing levels and models? For example, do you recommend a unit pricing or subscription model? Any other thoughts for how to get out of the gate? (timestamp: 51m56s)

How should I promote an online training course?
Related question: What sorts of teasers for these online training courses (instructor-led workshops in my case) do you think are most effective to getting people to buy? (timestamp: 67m24s)

What if my price creates sticker shock in the buyer?
How do you respond to a client that gets to the pricing section of your proposal and immediately says “Oh, boy, that’s a lot more than I was expecting.” (timestamp: 3m51s)

Should I track my hours to make sure my projects are profitable?
How do I internally track my effort for fixed-price projects, as opposed to tracking output? I hope to track the latter - the progress and success of a business outcome - through metrics I collaboratively articulate with the buyer, as you have suggested. However, how do I know that I have “profited” on a project, or that I have gotten more efficient over many projects? Do I track hours like before and examine categorized time spent? (timestamp: 9m35s)

How do I stop scope creep on a value priced project?
How do I manage a value priced project so that the scope doesn’t creep out of control? (timestamp: 14m18s)

Should I worry if my current clients don’t fit my new niche?
On the last call, you suggested making my LinkedIn profile super targeted and specialised toward my target niche market. Should I be worried about alienating current clients if they don’t match that new market? Or are there ways to mitigate this? (timestamp: 25m58s)

Should I resort to cold calling if I can’t connect with my ideal buyers online?
I’ve changed target markets now, but a few months ago I was trying to target those in motorcycle sales. I found it was difficult to find their email addresses, and they aren’t on sites like LinkedIn. Would you suggest resorting to cold calls in this instance? I’m not great at cold calling, so hoping there’s another strategy here to keep in mind for the future. (timestamp: 30m16s)

What if a new productized service would be too expensive for an existing client?
I have a client looking for something that would lend itself well to a single-day productized service like Knapsack, but I’m pretty sure they aren’t going to go the price I would find it worth doing for. In this case, would you offer something like this ad-hoc as a test, and simply outline the premise in the email? Thanks! (timestamp: 35m35s)

How would you grow your email list if you were starting from scratch?
If you were starting a consulting business from scratch today, can you walk us through the 1 or 2 content marketing tactics you’d use to grow an email list? I’m loosely defining content here - could be video, podcast, blog posts, etc. Thanks for being specific with what you’d do e.g. “I’d interview people who have blogs in my niche to rely on their distribution” or “I’d write lots of high intent content optimized for search”. (timestamp: 1m53s)

What should I do with old testimonials from clients that not in my new target market?
What’s the best way to leverage past wins with clients who came as referrals in a niche that you’re not overly experienced or well-networked in? I’m targeting independent, higher education providers here in the UK. It’s early days yet, but aside from some low-budget paid campaigns and some cold outreach, is there anything else I should be doing? (timestamp: 21m6s)

How should I approach cold outreach to a new target market?
I’m about to start contacting startup-founders about my consulting. My aims are: 1) To test the hypothesis I have that the problems I’m looking to address are ones they’ll pay to solve 2) To generate ideas for content marketing subjects 3) To find out if there are any opportunities for me to sell my consulting. (timestamp: 27m47s)

Which of these target buyers would you pick?
I like to work with scientific researchers. Researchers in academic institutions are often not economic buyers, making it hard to ditch hourly billing. I’ve come up with the following as potential ideal-buyer targets: CEOs of small (<500 employees?) manufacturers (that want materials innovation); R&D team leads at small manufacturers; materials researchers; materials research software engineers; scientific program managers; research project managers; computational materials scientists. Which would you choose? (timestamp: 35m13s)

How can I value price a three-party deal?
I am a member of a digital platform company’s “Expert Network”. The company pays consultants like me to help their clients leverage the platform. Both the platform and client benefit from my work. I am trying to find the sweet spot from a pricing perspective. Any thoughts for how to approach this one? (timestamp: 45m35s)

What would you do to generate leads on LinkedIn?
If you were using LinkedIn to generate cold leads for a productized service, what would your approach be? (timestamp: 53m47s)

How should a sales-averse solopreneur approach end of year business development?
I want to firm up my bizdev muscles and build up my selling confidence -- I’ve gotten by with referrals and a bit of content marketing, but it’s not enough. Any tips on how to approach end of year business development for a sales-averse solopreneur? My focus is short-term revenue wins and to start to lay the groundwork for collaborations next year. (timestamp: 1m38s)

How can I add additional value to my proposals?
What are the various levers/knobs/dials to modify value based proposals, the terms in agreement? (timestamp: 12m16s)

How should I structure my home page if I serve different types of clients?
Does it make sense to have a home page if you offer few services (2-3) for different clients? If so, what should be the structure of the home page? The example that got me thinking was the Services section from Annie Hansson page ( Each service would have “learn more button” which take you to its own sales page and addresses only one target customer. What’s your take on this? (timestamp: 29m33s)

How can I translate value into financial impact in a one-hour sales call?
Can you share some tips about how to structure a one hour business development call to make sure that there is enough time for the (financial) value conversation? Do you recommend proposing an agenda for the call? I generally do a good job of probing on the “why” which results in rich conversations at the macro level about the value of the work. I am not good (yet) at translating that into the financial impact part of the conversation. I worry that things will spin out. (timestamp: 47m28s)

How should I respond if presented with complex “legalese” from a potential client?
If a contract is required, what copyrights would you retain or give to the client, what indemnification do you provide if any, and how do you handle/respond to the red-flags that come from General Councils/attorneys? (timestamp: 65m11s)

How can I use my open source project to attract potential clients?
I have a software library that helps potential customers try out fonts on my type designer-clients’ sites. I’d like to open source it, probably with prominent newsletter signup on the demo page. Some of the audience is active on GitHub, at least for bookmarking. If it’s more focused on the “fix” than purely docs, does that seems like it could be an effective strategy? Maybe an email course on the underlying problem would be better instead? Thanks! (timestamp: 72m51s)

How do you part ways with a client?
How do you fire a client professionally? I’ve decided to let go of my last standing hourly billed client (a software company) and work exclusively with my target audience (metal working businesses). My work included doing onboarding for their key accounts, and they quite heavily relied on me so far, so they might get in some difficulties if I quit. (timestamp: 79m42s)

What’s the best way to structure a audit + roadmap + retainer agreement?
I’m talking to a previous client of mine who is keen to work together once they have acquired more funding. They’ve suggested that it would be helpful for me to do an audit of where they are with their setup, and help them develop a roadmap for what needs doing once they have funding. I think there might be a good opportunity for some retainer work to help keep them on track. What’s the best way for me to structure this? (timestamp: 83m29s)

What should we do once our new marketing starts bringing in dream clients?
After rebooting your business development approach and refined your methods you land the ideal product management contract with a great client, a model for the future value based pricing work you want. The client is in a growth mindset, ready to learn/grow, cash flush, aligned to your business values & mission. What things would you do next to build on this? (timestamp: 91m7s)

What can I do while still a full time employee to ease my transition to consulting?
I am fully employed right now and I am building my expertise authority through a blog to create a following and an email list. My plan is to wait at least a year before I go solo and start a consulting practice. I would love to get your feedback on how people like me (fully employed) to carefully and safely transition to consulting. Thank you! Note: love your podcast 👏 (timestamp: 97m12s)

Should I self-publish my book or go with a traditional publisher?
I’m contemplating writing a book. I’m currently weighing whether to write it in public (content marketing for my site and email list) and give it away for free online; with option to buy a dead-tree book. What would be any advantages or disadvantages to this approach? I’m also weighing going with a well known tech publisher. If I do that, what are the pros and cons to writing it solo vs having co-authors? (timestamp: 1m21s)

How do I ditch hourly billing if I really want to work with government and higher ed?
You say to “help people you like get what they want.” I fear I am doomed to like people who work in academic and government institutions with time-and-materials and milestone-payments-in-arrears procurement policies for custom project work. Should I bail on custom project work and focus on info products and productized services in order to ditch hourly billing? (timestamp: 22m36s)

How do I transition a disorganized client from fixed project fees to a monthly retainer?
I broke my own rule and took a somewhat challenging friend on as a client. She and the Chief of Staff at the company each have fixed fee proposals from me that they accepted verbally. They are somewhat disorganized and then asked for a monthly retainer model (which I had floated based on your advisory retainer option) but based on hourly rates. I refuse to do hourly with them and am now looking to transition the two proposals to a fixed fee monthly rate. Any thoughts? (timestamp: 28m47s)

Should I ask for a referral fee when introducing a vendor to my client?
Question about taking some margin for introducing other vendors to a client. In this case, I introduced a visual design company to my client. They have a skillset that my company doesn’t. I have collaborated with the founder in the past. For this project, I invested quite a bit of time to make and manage the connection so I do feel like some remuneration is reasonable. I get the sense that 10-15% is pretty standard. Any thoughts on this one? (timestamp: 50m27s)

How focused should I be about the ideal reader for my newsletter?
How focused should my idea of my audience be before I re-start writing my newsletter? How much do you feel like you refined that through sending it? Before, I would have said I wrote “about” typography. Now, I’m trying to make it about helping typeface designers and graphic designers. But that’s still two different people I work with and could write to, and I’m having trouble deciding between them. (timestamp: 56m15s)

Could you do a teardown of my home page draft?
Could I get a Site Teardown please? (timestamp: 67m59s)

Could you do a teardown of my LinkedIn profile?
If you have time, I’d really appreciate a teardown of my LinkedIn profile. I’ve contacted some clients from previous projects and got a couple of recommendations. I’m going to be doing direct outreach to people who fit my client profile starting next week initially to do market research as suggested in a previous call, and hopefully to generate some interest for follow-on work. (timestamp: 88m24s)

How quickly should I get on a call with an inbound lead from social media?
If someone reaches out to you on LinkedIn (or other social media), what steps do you usually take to move the conversation to a different channel (e.g., a call)? Do you qualify potential consulting clients through chat? Or make them go through your funnel? In other words: How quickly do you get on a call with them? (timestamp: 1m26s)

What’s the best platform to host my upcoming online course?
Do you have any experience with these new self-serve platforms for developing training content? I have been exposed to HowToo (from Australia), Thinkific, Teachable and Udemy. I also have an option to create a course with Madecraft that then sells the content to clients like LinkedIn and Spotify. I know I want to offer online training...just wondering where to start. (timestamp: 5m41s)

How should I respond to a prospect who thinks they are an expert at what I do?
If a potential client acts on the phone like they are the expert themselves, how do you usually (politely) steer the conversation to open up about the problems they experience in their business? (timestamp: 7m45s)

Is it okay to mix cash and equity as compensation for an ongoing advisory retainer?
How would you approach a mixed advisory retainer + freelance CPO/head of product opportunity in terms of asking for cash + vested equity? Loved your BoA episode on retainers, seeking more on this. Goals I have: this startup is aligned to my mission, but they’re at square zero with only a business plan and my vision & strategy consulting work to date. They have decent funding from prior startup profits. Also want to maximize cash flow so I can fund the reboot of my consulting & advisory practice. (timestamp: 13m25s)

Knowing what you know now, what changes would you make to your old sales pages?
Looking back at one of your earlier sales pages (, what improvements would you make today? (timestamp: 18m26s)

How should I respond to an advisory/training client who wants me to directly assist on one of their client projects?
I need to update my contract with one of my consulting clients. I am currently on a monthly retainer that covers training, office hours and general advisory. The client now wants to bring me in as sub-contractor on one its client projects. They sold a fixed fee project and their margins are tight (apparently). Planning to give 3 options but expect a battle with this value conversation. (timestamp: 29m44s)

Should I charge a fee for referring work to one of my retainer clients?
Same consulting client. I want to add a referral fee component to the contract. I get the sense that fees are generally in the 10-15% range for a referral. Can you share your experience with this? How would you structure the conversation? Thanks! (timestamp: 39m57s)

If my prices are on my site, when do I bring up 100% up-front payment terms?
If your prices are on your site, do you bother sending a proposal? If not, when do you bring up up-front payment? (timestamp: 42m27s)

How can I bring ghosted deals back from the dead?
At some point (can’t recall where you shared) - you referenced a tasteful one-line (one-time) email outreach script. Can reshare that resource? (timestamp: 48m15s)

Should I partner with a company to co-brand my podcast?
One of the companies I interviewed on my podcast approached me to “collaborate” on the podcast. They are a startup selling a product to companies doing in-app subscriptions. They just raised some money and want to build authority in the marketplace and grow their international reach. One avenue for this is through podcasting. Two options are on the table right now: - a sponsoring audio billboard in the podcast - cobranding of the podcast Thoughts? (timestamp: 54m25s)

Can I get a home page teardown?
Can you do a teardown of my new productized service homepage? Fyi video is in the making. (timestamp: 64m39s)

How do handle the internal war between “being polished” vs. “just ship it and iterate”? I am specifically thinking about a course I am developing. (timestamp: 2m9s)

There are many experts in my technical field, but they are either academics, internal employees, or owners of manufacturing companies. How do I highlight on my website that I am the only consultant with strong online presence in my field? (timestamp: 4m53s)

Hi there. I am curious about 2 things. Should we ask potential clients what their budget is before sending a proposal? Should we strive to price our offerings (x for a particular type of engagement, y for another) rather than coming up with individual value-based estimates for each engagement? (timestamp: 14m14s)

How do you distinguish and structure an advisory retainer engagement versus coaching? Are there other kinds of productized services that are longish-term (4 months or more) and that don’t have the clear beginning, middle, and end of a custom project? (timestamp: 25m38s)

How to help prospects define the desired outcome that is measurable when it comes to creating new apps? Context: Call with the candidate was around a new product opportunity for his self-funded startup company. The goal was to make an MVP; he’d would take over the marketing. However, he couldn’t understand how to measure the success of this MVP project other than 0 and 1. (timestamp: 41m31s)

I quoted my client 3 options based on value after a sales call. My missing link was putting a number on that value with the client. The proposal went far beyond the initial request for facilitation support. My pricing was out of alignment with her expectations. She went dark. I sent an email offering to work with her on pricing but she still didn’t respond. Should I just let it go or close out with one more email with a link to highly relevant content as placeholder for future discussion? (timestamp: 55m29s)

Just launched a new consulting site with tight specialization + positioning. Would be grateful for a teardown if you’ve got time. (Leaving out the specialization to see whether it’s clear when you visit the site). (timestamp: 74m3s)

I’m building a side hustle solution for this company: They manage homeowners associations at residential communities. I found this convention from 2020 My assumption is that people in HOA management are the types of people in attendance at this event. Can you help me find a watering hole for HOA Management companies? (timestamp: 101m8s)

Submitted a retainer proposal about a month ago; and gave a month expiration. It expired a few days ago. Sent a follow up today and received a response that budget approval wouldn’t come until August at earliest. How do I handle this since I have already told client in writing that the proposal would expire on a given date? (timestamp: 1m 20s)

I’m booked out with retainer clients through the end of the year (thanks in part to a lot of the things you talk about here!). I’m considering adding a group coaching offering to expand my impact & take on more clients w/ less time investment. Thoughts? Advice? Things you would do differently the 2nd time around? (timestamp: 8m 39s)

Can you talk a bit about the pros and cons of using formal contracts with clients vs. just having a proposal with some plain language terms spelled out (and getting paid while you still have leverage)? (timestamp: 16m 29s)

How to convince ideal buyers to talk to “get the insights” for copywriting material? I’m becoming more and more aware that I speak my own language and not theirs. I’m in the process of rewriting a productized offer. (timestamp: 26m 59s)

In a previous group coaching session the topic of prospecting came up. I was wondering what avenues you recommend for prospecting. As a tutor for a standardized exam I was thinking Reddit communities for the test might be a good place to start. What are your thoughts on that? (timestamp: 33m 18s)

Have you even run into a scenario where you were paid 100% upfront for a project, delivered some of the services (call it 40%), but then the client decides to cancel the project? Do you give them a partial refund or credit for future services, or do they usually just look at it as sunk cost and move on without complaint? (timestamp: 45m 45s)

Follow up on the prospecting question. Is it a bad idea to re-publish the responses I create for people on Reddit later as blog posts, etc. So not sending people to a blog post from Reddit, but creating materials from those materials to publish elsewhere. Seems like it would be an efficient way to create content while prosopecting. (timestamp: 56m 45s)

I want to position myself as an expert on one thing (thank you Blair Enns), and I want that expertise to be in something I can value price. Problem is that I’m a young designer and I’m not sure the breadth of what’s out there that can be priced that way. Can you give some examples of what you mean by custom projects? (timestamp: 2m 20s)

I loved the recent episode about retainers. You mentioned a few landmines to avoid. What landmines should one avoid when defining deliverables for technical oversight? How to prevent defining deliverables that can be tied to hourly billing? (timestamp: 10m 57s)

The niche I’m looking at is helping tech startups who want to develop their own in house data & analytics capability so that they can give better information to their investors, and guide product development & marketing. I’ve done this for a client through another business I was involved with and they got a lot of value of it. I want to offer productised services, advisory retainers, coaching & support to the client’s tech team. Any feedback on that as a niche idea would be appreciated :) (timestamp: 23m 7s)

This morning I started the process of picking a niche - knowing from your prior messages that a properly narrowed niche will help the sales process. I was wondering if you would be willing to give some feedback on what I came up with? Feel free to share in your emails if you want as well. Here it is: “I build eCommerce websites for local construction equipment distributors.” Pick it apart. Rip it to shreds if need be. (timestamp: 34m 56s)

If you have time left, could you do a brief services-page breakdown? It’s targeted at CEO’s or plant managers of manufacturing companies that want to digitalize their businesses. (timestamp: 43m 43s)

You mention on delivery terms when a client pushes back on 100% up front to potentially let them pick the date. If the project is expected to take a minimum of 6 months or a year; it doesn’t seem reasonable to let 6 months or a year go by to let them pay the other 50%. What do you suggest to do in the case where the project is long lasting? (>6 months) (timestamp: 2m 47s)

For advisory retainers, what is your process? Any initial meeting to agree on outcomes? Or do you not worry about outcomes because you’re a brain to pick? How do you scope lengths of advisory retainer agreements (your site used to have month, quarterly, and yearly plans)? What do you do in cases where the client didn’t want roadmapping due to price but wants an advisory retainer? The fear being trying to get the work from the road mapping during a retainer (timestamp: 7m 2s)

If the project price is high (let’s say >100K) are your terms still 100% up front? What if it’s over 200K? If the project is slated to last 6 months, does that change how much (if you choose monthly?) what about if the project is slated to last a year? (timestamp: 24m 21s)

Can you talk about the role of self-discovery/reflection, peer-learning, and guru coaching in a solopreneur business? Also, curious, do you/did you have a business coach? (timestamp: 26m 1s)

I have two types of technical advisory clients: (A) Clients who need my help to progress, perhaps even to fight fires. In this case I sell myself as a leg in their 3 or 4 leg chair (B) Clients who see me as a wonderful technical resource, but they don’t believe I am a critical “feature” of their project. It turns out that Client B is a lot more fun to work with. What’s the best way to get more B-types? Also, if I find a hot prospect who is Type A, should I pitch them Type B services? (timestamp: 30m 28s)

Q:How to handle situations where client is unhappy with bugs popping up, but imposes deadlines that force the team to act quickly? Context:Client changes their mind or requires quick turnaround to meet internal deadline (ex: custom feature for a sale event). In order to meet the aggressive deadline, we have to forgo quality standards and bugs slip through. We’re at budget reneg and they’re asking to have bugs handled at reduced cost but the reason we have bugs is due to pressures applied to us (timestamp: 38m 39s)

How to politely decline long term commitments and even employment offers from clients? Often executives and owners try to invite me into their teams. It could be as simple as asking me to lead a team for a project with more than 3 months… or outright offer interim positions. Just saying “hey thanks, but no” sounds a bit harsh to me. How do you usually communicate that your not intending to be part of a company, but rather run your own business. (timestamp: 43m 33s)

How do think about reselling software with consulting projects? For example, a client approaches me with a project request for a web portal. The client thinks it needs to be custom build, but I know a few good SaaS solutions that could solve the need faster, cheaper and more reliable. Would you then also make a deal with SaaS provider for reselling (commissions / VAR), or prefer to just make the introduction? For context; I often get offers from SaaS providers to resell their products. (timestamp: 45m 47s)

How to start writing and structuring email course (lead magnet), what to avoid during the process? (timestamp: 50m 10s)

Is there a way to ask for testimonials to use it for personal brand from clients if you’re still working as employee in agency? (timestamp: 53m 30s)

How do you estimate value of a project for an organization with no profit motive like a non-profit or government agency? It’s obvious on the cost side (e.g. this project will save us $100k per year) but what if they want help with an objective (e.g. we want to change our data science process to promote reproducibility). How would you think about putting a number to a value/objective like that? (timestamp: 58m 28s)

Teardown of the sales page for Summer Functions with Queen Raae and the Nattermob Pirates. Looking for input on structure, functionality and if I am missing content; I will have an editor check for spelling and one of the pirates will make it pretty. (timestamp: 67m 49s)

If there is time, I’d love to get feedback on my course salespage. I have a hunch something is missing, but I have stared myself blind. (timestamp: 93m 58s)

How does marketing and creating online technical training courses differ from marketing to individuals vs. to companies themselves? (timestamp: 2m 0s)

I’m putting together a proposal using your 3-option template and I’m struggling to come up with a compelling Option 3 with ~5x the value of Option 1. What’s more important: the pricing formula (1, 2.2x, 5x) or the number of options? (timestamp: 5m 54s)

Clearly, the Why Conversation is important for pricing. But a prospect mentioned she wants to use this upcoming conversation to talk about her costs. How dogmatic should I be about not discussing price during this conversation? Are ballparks OK? (timestamp: 14m 59s)

I’ve heard/read that it is better to do short engagements vs. long ones. Can you elaborate more on the benefits of short engagements vs. long engagements? Also, how does this fit in with the idea of an advisory retainer. (timestamp: 23m 4s)

Hi J, how to choose the most suitable type of lead magnet? How to test it and get good feedback? And finally, how to create an autoresponder sequence in terms of content structure, where you try to sell a service, e.g. Business Strategy or Design Sprints? (timestamp: 30m 58s)

I have a customer with which I currently have an open-ended contract for strategy consulting. However, I would love to go on vacation this summer. How do you usually communicate/plan this? Do you usually put contracts on hold? Or do you just stay available / work part-time? (timestamp: 40m 31s)

I have a prospect who’s looking for some contract help managing a dev team while their FTE is on mat leave. Their desired outcome is to keep the team humming and keep output high so executive stakeholders are happy. The team’s goal is to drive $xx million in annual recurring revenue. My prospect’s instinct was to ask my hourly rate and I told her I priced based on project and outcomes. Would you price this as a project? What outcomes would you use? How would you price relative to rev. goal? (timestamp: 44m 33s)

I often struggle to define my target market in a consiste way mainly because I lack vocabulary that describes precisely a certain category/subculture (English in not my native language) . Any directions or ressources to help with that ? (timestamp: 48m 46s)

Could you do a proposal teardown for me? It’s for a B2B SaaS backed by Private Equity in growth mode. Here’s a link [redacted]. I’ve removed the identifying information; but haven’t removed scope or price. (timestamp: 54m 14s)

I want to work on strategy with my clients, but they never have the technical nuts and bolts together for the basic work so I get sucked into hands on work. Therefore, I am creating paid courses to capture all of my technical knowledge, so when I engage, I can direct the client to my courses for technical info, which frees me in a strategic advisory retainer. How does this sound? (timestamp: 1m 56s)

Hi Jonathan, How would you deal with a client with whom requirements are constantly changing? Even at the outset of a project, requirements end up being completely different. How would you manage this when it is happening all of the time, seemingly across every project, making it impossible to plan? I’m tired of playing whack-a-mole! (timestamp: 7m 6s)

Lately, I have written quite a few retainer proposals (with the pricing tiers) for product teams that need outside help. Here I have a challenge. Primarily I’m a Product Designer. Clients usually want me to take their product idea to the research phase and design. I have a challenge in combining product development, which is research+consulting and hands-on work, which is design. I find it hard to get a deal one without the other. How do you even structure something like that? (timestamp: 19m 28s)

Any tips for growing a podcast audience? Our format is short 15-minute episodes every two weeks with me and my partner. We just published episode 22 and haven’t missed a beat. Growth is slow and steady, around 2000 downloads total. I post new episodes on Twitter and just started on LinkedIn this week. Inviting a guest is a possibility we’ve considered, but with the short format seems limiting. Any recommendations? (timestamp: 30m 33s)

I find that engineering directors/managers like the idea of doing things the right strategic way, but as soon as any pressure come, they drop all good practices and start their teams on frantic short-sighted work processes, thus the consultants work gets undermined. Any advice on how to deal with this shift in client attitude? (timestamp: 45m 51s)

How would you deal with a client who has shown they can’t be trusted to deliver things on time(feedback, assets, copy, even payments), but whose project is actually fun. How would you correct course? (timestamp: 55m 46s)

How would you structure a technical advisory retainer where you would be available to a whole engineering team ranging from 2-10 people? Both advice on mechanics and pricing would be appreciated. (timestamp: 2m 13s)

Creating content that answers expensive questions for expensive customers and markets those content. What are the processes and how long does it usually take for one to start seeing results? (timestamp: 13m 55s)

I’d love your insight on offering an “exclusivity” option to clients. As in “I can offer [SERVICE] for [$RATE]. If you’d like to be my exclusive client in [THEIR INDUSTRY], the free would be [$HIGHER RATE].” Happy to provide additional context in the chat if that would help. (timestamp: 28m 30s)

How should I disengage from a long time client who is annoying, has unrealistic expectations, and is needy? I am planning to help them outsource all of the execution work I am doing, formally teach them all of the common sense stuff, and continue on an advisory retainer with clear terms. (timestamp: 38m 48s)

As a designer/developer, I usually land bigger projects when I’m referred by an independent CMO since he is trusted by larger businesses. Should I focus on building relationships with more consultants rather than bidding on projects directly? (timestamp: 45m 59s)

Recently you posted [somewhere] about the impact of privacy changes on podcasting though you still support it as a “speaking channel”. Any more insight on what the challenges will be? What do we need to know? (timestamp: 55m 59s)

How would you structure an engagement which is going to address an urgent problem for a client (like root cause analysis product failures)? What if you can’t predict the amount of time it will take or if you will even be successful? How would structure the engagement and collect fees? In the past, I have tried to guide the client’s employees to do the investigation, but I am realizing that I need to do it in order to provide results. (timestamp: 1m 40s)

I’m currently working on “gathering” for the pivot in my business: coaching for CTOs of growth stage b2b SaaS companies; I still need to hunt. How do I handle this duality on the web? Let’s say I’m “hunting” for strategic architectural advice on microservices. (Which dovetails into what CTOs may need advice on). Do I advertise the hunting (architectural) part on my site/LinkedIn to get inbound leads while still working on the long term gathering? (timestamp: 17m 30s)

This is a positioning question. I am a marketing specialist and have been on Upwork for the last 3 years helping clients scale brand growth by providing SEO, PPC, and full account management services on Amazon. My current focused target market will be brands that need full funnel programmatic media planning on and off of Amazon with DSP Display inventory and I would like to pivot this current stream of income to an increased value position. Q: What strategy to use to reach this goal? (timestamp: 33m 24s)

I used to offer retainers (niche dev work), but have moved to projects b/c I didn’t like being “on call” for questions & bug fixes. Projects take about a month, but clients usually repeat engage for 4-6 projects in a row. When they reach out about little stuff outside of scope, I handle it b/c they are a great repeat client. So I’m back to having a de facto retainer and feeling like I am on call to answer questions & fix things. :-( Is there a better way? How else could I be thinking about this? (timestamp: 54m 4s)

I’m formalizing my client onboarding process and am looking for best practices on how to streamline things (inquiry & discovery calls, proposals, project scoping, statements of work, contracts) while building trust and setting a good impression. At the moment, scoping sucks up the most time, as my engagements are primarily based on fixed pricing and are customized to the client (I’m working toward productizing). The projects aren’t big enough to use value-based pricing. (timestamp: 2m 0s)

I’m doing customer research for a new target audience (B2B SaaS CTOs), I know a few B2B SaaS CTOs personally and have reached out to conduct interviews with them. I’ve also cold-reached out to other B2B SaaS CTOs via LinkedIn; and as of yet don’t have a great response rate (6.67% total, all of which have been personal reach-outs). Should I keep doing cold-reachouts on linked in or just accept that personal network and friend-of-personal network is who I should stick to talking to? (timestamp: 24m 54s)

I’m interested in your perspective on building an email list from nothing (literally). I have a strong LinkedIn network, but have just gone out as an independent. Some options I’ve been exploring: • Organic growth through blog post publishing to LinkedIn • LinkedIn lead magnet • LinkedIn post asking for subscribers • One time email, asking for an opt-in • Adding a sign-up button to my email signature What approach(es) would you recommend? (timestamp: 33m 1s)

I have an advisory retainer offering where weekly meetings are the main focus. The issue is that sometimes the client doesn’t make enough progress to want a meeting that week or they change priorities without a plan to resume. So, they get some extra weeks. I don’t like managing that. How can I structure my offering/pricing to avoid makeup weeks. Should I make them pay for 6 months at a time? Should I say there are no cancellations and if you disengage, the cost to reengage is twice the cost? (timestamp: 39m 44s)

When meeting with a new prospect for the first time, I like to do an intro slideshow, about 5 mins, about how & when I started the company, our core values, primary services and standard methodology. I usually do this before I ask them to brain dump, because I want to give them perspective on my company and how we can fit into their plans. If it’s a company that I already know, or if they sought me out first, then I ask for the brain dump first. What are your thoughts on the intro? I sometimes find that people don’t want to brain dump before they feel like they know me just a little bit. (timestamp: 42m 19s)

I’ve been paid for about a dozen different services over the last 14 years and I’m looking for a way to niche down. Two questions you ask are “What do you want to be known for” and “Who do you most want to help”. Do you have a framework or other questions to help identify a niche beyond those? (timestamp: 47m 49s)

If you are bad at writing content for a blog or creating videos but have been able to generate enough revenue to have someone else solve that problem. How would you go about finding the right person to do that? For example, explaining to a writer my past experience as a VP of Engineering and how that can help prospects avoid failed projects and have the writer create the blog. (timestamp: 57m 3s)

How can I answer the question: “When are you available to start?” when talking to multiple leads -- worried about losing credibility by saying I am talking to someone else, so move quickly if you want to be my next client. (timestamp: 1m 23s)

Can you explain the steps to create and publish my first paid course offering? Which platforms are working for your students? (timestamp: 4m 26s)

How do you decide if a particular piece of content should be a freebie or require an email address to access? For example, if you have a five day guide to something, how to decide whether to make it a 5 day email course, pdf requiring email, pdf not requiring email, or blog post? (timestamp: 15m 41s)

I am still navigating the tension of: “Do I want to stay a solo-expert or shift to becoming a small firm. I know some of this depends on volume of work - but some of it is mindset and positioning from the beginning. As an example: one may choose to use their company name in the title of their podcast branding versus their personal name. Any insights into when one should look to commit to a path - resources to check out - or decisions to consider along the way? (timestamp: 23m 35s)

I’d like a teardown on our book landing page (Bio and testimonials will be added in the next version) (timestamp: 34m 1s)

Is there a way to value price a fixed output job like a data scraping project? (timestamp: 46m 31s)

I charge $3,500/month for advisory retainer having a once a week meeting with some light support between meetings. I recently added a $495 one- time call. These two offers don’t make sense to me - wouldn’t 4 meetings/month cost $2000/month? I want to continue to offer $3500/month retainers, but I find that the $495 calls don’t fit with the pricing model and I fumble when explaining the two options. (timestamp: 1m 10s)

I’d love to get some tips on how to proactively identify and go after short and mid-term high ROI opportunities. I’m feeling frustrated about spending time and energy on activities (small scale projects, content marketing with somewhat limited reach, free workshops) that provide benefits to my business but don’t yield the highest returns. Maximizing my profit is a big priority for me at the moment after a difficult 2020 (Won’t be able to join the live session, but thanks in advance!) (timestamp: 5m 45s)

I’d love a critique of a positioning statement I’m working on: “We help Architects and Builders [in New England] clarify your message, stand out from your competition, and attract qualified leads through award-winning websites.” - (I may leave off the bracketed location part.) (timestamp: 16m 57s)

How do you recommend we tactfully handle project delays, specifically for website redesigns. Often a project will get delayed because we’re waiting on the client for some reason (copy, etc.) which causes a number of issues but the most painful is that we start other projects in the meantime and then are doing double duty when the original client(s) are ready to move forward. (timestamp: 30m 26s)

HELP! My to do list includes launching some software (as products), improve my email list, develop a course offering, develop an e-book, direct marketing campaign, do online outreach, conference presentations, YouTube videos, systematize my consulting work, develop a podcast, write SEO articles for my website. How do I decide what do to do? As you can see, some things are long term and some are short term. Some things keep the business going and some things build the business. (timestamp: 37m 0s)

How do I determine if my prices are too high for my advisory retainer? (timestamp: 51m 9s)

How do you know if you’ve spent too long trying to get a channel to work? For instance, with an email list; is it no growth over days? weeks? Months? At what point do you re-evaluate experiments? (timestamp: 54m 22s)

What products, that currently are not part of your ladder, did you try and decide to ditch? Why did you ditch them? (timestamp: 60m 14s)

On the question of “my to do list is insane” part of your answer was “first get a 20h/w job to secure cash flow”, to which George asked “what if you need to bill full time to secure cash flow.” Your answer was a couple of things, but included what I think amounts to: 40 full time & 20 on business? Ok. 60 hour wk. That’s ok if it’ll work. For someone serious about it, that’s not too bad. Presumably it’s temporary until the 20 starts paying off. You mentioned increase the profits/double the rate, etc. Sometimes, not possible -- eg. “full time” cash flow is “job”. So if that’s the only really viable option, I don’t mind a 60 hour week if it’ll work. Have I understood correctly, or did I miss anything important? (timestamp: 64m 49s)

What do you think about this linkedin tagline for a R&D product development consultant: “Expert at guiding R&D engineering teams on how to complete projects with pride rather than with excuses.” (timestamp: 1m 16s)

Hey J! 👋 You and Rochelle talked about the central theme for everything you do - newsletter, podcast, blog, books, pretty much all the marketing material. Would you validate the theme before you go all-in? And if so, how? Also, on that note, how do you know the theme isn’t “too much board” or “too much niche”. Example, for a better idea: Testing Business Ideas vs Design Sprints for validating Project Management product ideas. (timestamp: 9m 20s)

My standard package is: “Find and articulate your message through Brand Storyboarding” (3 sessions) I have arrived at 1800$, Sold it once so far. But some don’t need to clarify their message, and still are drawn to my work. For “just illustrations” I feel the price is too high. Should I differentiate my service, work on my mindset, or send them away? Or is the 1800 for messaging consulting even too low? Is my “designer identity” getting into the way? (timestamp: 19m 1s)

Just made a Mondo pivot last week. From ~pure technical consulting, I’ve moved all new business development to R&D product development consulting with my own unique flare. What are the steps to get this off of the ground in three months? (timestamp: 25m 3s)

Just got this in response to asking for 100% up front. Have you dealt with this before? “The problem with paying you up front is that we has nothing to show in the event that you fall ill or pass away during this engagement. During COVID this is an even more pressing concern particularly when working with an individual versus a firm where there may be back-up support.” (timestamp: 34m 57s)

Our first productized service is something we call “Discovery Phase” (Project Briefs, Service Blueprint, Personas, Red Routes Map and Wireflows). It’s meant as a phase before we start to write tailor made software. Something we missed in so many projects before to ensure a good result. It’s focused on SMBs. Usually, they don’t know what the deliverables (blueprints, maps, wireframes,...) are or why they need them. How would you explain it to them? Webinars? YouTube? White papers? Website only? (timestamp: 37m 8s)

Can you give me your thoughts on my positioning statement: I’m a brand strategist who transforms B Corporations brands from ho hum to heck yeah! Thank you. (timestamp: 43m 2s)

Hey Jonathan. Can you do a quick website tear down of my site? Thanks. (timestamp: 50m 11s)

I’m really struggling with efficiently producing regular content (blog/LinkedIn posts, newsletters, etc). What seems to slow me down is the pressure I put on myself to write things well and concisely (I’m pretty verbose). Do you have any tips on how to the process more efficient? What’s your take on quality vs. quantity? (timestamp: 1m 26s)

How would you recommend pricing low-touch webinars and workshops (those that are fairly templatized)? Looking at offerings on the market in my field (innovation/design), I’ve seen things priced anywhere from $20 to $100 for individual sessions lasting 1-2 hours. The upsell opportunity would be coaching, larger-scale professional training/facilitation and strategic advisory. (timestamp: 14m 46s)

In “Win Without Pitching”, Blair is adamant about not giving away consulting for free. I’ve heard you talk about giving stuff away to the internet as a marketing technique. Can you talk about how you think about this? Is it simply a matter of not giving free consulting to an individual client? Or do you differ from Blair in your approach? (timestamp: 23m 7s)

Tried value pricing deal for company that is losing thousands per day due to bad website. My pricing was 24k to just fix their problem. (Couldn’t get them to endorse other options that could have gone into calculating a variety of pricing options unfortunately.) After ghosting for a few weeks and a couple of prodding emails they finally got back to me and said “Currently, we cannot justify spending that amount of money on enhancements/improvements.” Should I bother trying to make something work? (timestamp: 29m 50s)

Should I invest time in creating technical e-books and technical course offerings when what I really want to do is start moving away from (only) being the technical advisor to more of the strategic advisor? (timestamp: 43m 41s)

I decided to create an email course to teach PPC marketeers how to get started with Google Ads Scripts to automate some of the tedious tasks. The goal would be to funnel them into some of my paid services. I have never created an email course before. What mistakes have you maid that you could help me avoid? (timestamp: 50m 12s)

I posted a question in the slack channel regarding figuring out the value for a Shopify e-commerce website. I do not own the relationship with the client but being hired as a design/dev implementation partner. They currently make $100k in e-commerce but want to make 5M in 2 years. What do you think the project value would be for this? (timestamp: 58m 3s)

Have you seen daily emails work for tech heavy content? Like from a developer doing mostly tech tutorials and paid dev courses etc. (timestamp: 65m 55s)

I routinely do workshops for $99-149 price. Recently others in the field are doing lots of free webinars. Of course they advertise their products during webinars, whereas I scrupulously do not, and my workshops are hard-core instruction. I’m wondering though if I should record a few short videos for YouTube that include some of my workshop content, as a contrast to the freebies out there? (timestamp: 68m 16s)

I redid our website after TPS5 and I think I’m ready for a tear down (timestamp: 69m 56s)

I use technical tutorial youtube videos as the top of my marketing funnel. With regards to CTA’s in the description, I usually see a whole bunch of links and information, from actual video descriptions, links to more videos, and links to get on email lists. Is there any best practice? Does this shotgun approach work for youtube descriptions? (timestamp: 1m 13s)

What is a good rule of thumb for how much time to spend each week on prospecting vs. client work? Now that I’m so focused on building the business, I sometimes find it hard to find the time to actually do the work! I’d like to set some sort of schedule that I can plan around and stick to. (timestamp: 7m 8s)

How important do you think innovation is when trying to make a dent in a niche or to establish yourself as an Authority? As I pivot to a new niche, I always find myself trying to create something unique, or at least a bit better. I’m not sure if this is my most valuable skill or a complete distraction! Should I focus on better tactics and execution or building a better mousetrap? (timestamp: 18m 19s)

Listening to prior episodes, I think I heard you say that you wouldn’t have the why conversation for a job under $50k. Is that right? If so, how do you value price smaller jobs ? (timestamp: 29m 30s)

When should you offer credit card options for payment? Did you offer them when you did retainers? Obviously, credit card comes with extra charges for the provider, but ease of payment for the client. (timestamp: 40m 47s)

Follow up... Two weeks after your sales page teardown, I now have a live info product! Can you comment on my launch plan? (1) ~10 free copies to people I want testimonials + feedback from (2) Personal emails to ~10 people in my network “Do you know anyone who would want to buy?” (3) Email sequence to my list (4) 5 LinkedIn posts (5) A guest podcast appearance (timestamp: 45m 28s)

How to move forward with someone (e-bike leasing founder specifically) who has asked if they could pay me for some hours of no-code advice/help and make it a non-hourly thing? (timestamp: 57m 2s)

I get leads via email. Most of the time the request is pretty vague (ie: “I want to start automating Google Ads using scripts, can you help me?”). I dont want to schedule phone calls. Do you have tips for having the Why conversation via asynchronous communication like email? (timestamp: 1m 35s)

A client with whom I have an ongoing relationship asked me to sign an NDA, ostensibly to protect their own clients. I would’ve declined the opportunity had the demand been made in the beginning. After some deliberations and legal advice, I ended up making some changes to the document. I haven’t received a response yet, but expect one shortly. Any advice on how to face the current situation and avoiding similar ones in the future? Sorry if this is not enough context or the question is too broad. (timestamp: 7m 24s)

I’ve been starting to think about tiered pricing however I’m falling into the trap of thinking of the price tiers in terms of more time/features which I want to avoid because the time spent doesn’t determine value. Do you have any thoughts or resources on how to frame your tiered pricing based on value/benefits? I’d like to offer web design support but struggling to think of how I’d split this up into tiers beyond more hours. (timestamp: 10m 30s)

What are differences in marketing to small business owners vs. corporations? (timestamp: 21m 33s)

Can you recommend a product ladder that would be appropriate for a solo consultant who does technical advisory engagements for corporations? Specifically, would corporations buy a single consulting session? I think they would expect an intro call to be free, even if I did promise actionable outcomes from the meeting. (timestamp: 28m 35s)

Can you do a quick website teardown of my home page? (timestamp: 36m 14s)

How do you value price someones idea? Example someone comes to you with an idea for the next great social media app. They have a good idea, they want to build but the why is something less tangible than money. They want to “change the world”. Only thing I can think of is to pull from my experience in what it takes. (timestamp: 2m 10s)

I have an hourly billing corporate client that I would like to change to a retainer model. I have only spent 7 hours yet. The work I am doing is providing an instructional course, weekly meeting, and an open ended research project. I would like to change to a retainer payment. They have already prepaid for $6k of hours. How do I get these guys to a retainer? For a new client, I would be happy charging $9k a month, but this seems too high based on an hourly rate parallel. (timestamp: 16m 52s)

After a client chooses an option and signs the proposal, do you then send them a work agreement that covers more specific details regarding cancellation terms and liability? Or is the proposal generally the only document you have signed? (timestamp: 22m 16s)

When you’re specialized and focus on a vertical, sometimes it’s hard to get testimonials and case studies when your clients are essentially competitors. Testimonials may be easier, but case studies with actual results may be harder. After all, clients don’t want to advertise their numbers to the competition. Any suggestions around this? (timestamp: 26m 37s)

I’m (finally) coming to the end of a 2-year project. Can you suggest any resources for best-in-class offboarding my client? I want to capture testimonials, get the green light on case studies, and make sure they feel supported as I transition away. (I have plenty of time on this one, so I want to do it right.) (timestamp: 30m 37s)

I’m preparing a productized service for a digital product validation - design sprint workshop. I’m targeting C-level people, with little time and high risk in strategic product decisions. In a previous company, I only had one such client that perfectly matched my ideal buyer persona profile who needed such a solution. How to find more people like this to ask them about their problems, wants, needs and convince them in an interview? Happy holidays to you and your family! (timestamp: 37m 3s)

Quick question regarding hourly billing, which I still do for the moment. I’ve also had day rates in the past. If part of the work has to do with researching a particular item/solution that more than one client happens to need, how do you handle billing? Do you bill clients equally, bill based on a weighted average of how much each client pays compared to others, or some other way? I want to do things with integrity. Thanks in advance. (timestamp: 53m 24s)

Is there a way to define a measurable goal for my Brand Storyboarding? (Listened to the experience economy podcast today...) (timestamp: 57m 20s)

How would I communicate/get agreement/or deal with pushback if I want to send an assistant/junior person to a client meeting on my behalf in case of scheduling conflicts (whether the conflict is a doctor appointment, car change, another client meeting)? I would not be billing that client for the person who shows up...that’s on my own dime. (timestamp: 63m 18s)

Huge headache: middleman contracts with recruiting or prime vendor firms. I recently posted my typical addendum on a webpage for clients, based on my personalized proposal template. However, on rare occasions, the other party doesn’t want to amend, only say that they never enforce the parts that I balk at: (i.e., intellectual proper, work for hire, etc). How do I not get trapped in sending everything to an attorney each time, or caving to their verbiage? (timestamp: 68m 16s)

Requesting a sales page teardown for my 3-tiered infoproduct... (timestamp: 74m 14s)

I need a new “why” conversation. The US Dept of Defense recently published new cybersecurity regulations so I’m talking to lots of prospective new clients. They conversation: Why this? “because I have to” Why now? “because I have to” Why me? “because you’re an expert” So how do I value price these jobs? The value is flipped in this situation, because they aren’t trying to grow their market or improve user experience, nothing positive, rather they are trying not to go out of business. (timestamp: 1m 57s)

I want to start a weekly email newsletter but am stuck on what to write about that would be interesting to my audience (manufacturers who want to optimize their website). I currently write about my craft of web design and development and attract my peers and companies that want me to do the implementation. But how do I attract and nurture a CEO/CMO who may not understand or care about the details of my craft but more the results they provide? (timestamp: 16m 36s)

I am a Google Ads specialist, using a lot of small scripts to automate the work. I am considering a service where people pay for the scripts I created to run my Google Ads agency. Occasionally I sell them as one offs, without support. I have a library of scripts that people are willing to pay anywhere between $100-$1000 for per piece. What business models would you suggest? (timestamp: 20m 4s)

How do you get from technical consulting with technical teams and project managers to strategy consulting to executives on technical matters? (timestamp: 26m 8s)

My offerings are purely B2B-focused (high-touch engagements), but I see some market potential in building training/coaching programs targeting end users (includes some interaction/support). What are some of the pros and cons to consider in pursuing a hybrid B2B/B2C model? How could I know if the upfront investment is worth it or if it would just distract me from my core business? Should it be potentially spun off as a separate brand since the positioning would be a bit different? (timestamp: 32m 30s)

I had a few clients who went through a Brand Storyboarding process and found a position and message they were happy with. And then... they don’t act on it. What to do? I want them to succeed, but can’t force them. Thinking about adding a few months of support to the package. (timestamp: 40m 19s)

At what point is good enough, good enough? I sometimes have ideas that I think “no I can make tweak this better”, and I feel I know I’m wasting time. But I’m worried the client will see the issues I can. (timestamp: 43m 15s)

A referral by the right person will always be great, but what’s the best type of social proof/testimonial you feel would be best to gather? A video or written or a particular platform or something else? (timestamp: 49m 37s)

Hi Jonathan, can you speak a little about managing the transition from full time employee to consultant without any kind of financial safety net? I’m currently working full time while I build an initial client base. I have a couple of projects that are looking likely to kick off early next year. I’m aware that my time is a limited resource and I feel like I have some careful planning to do around managing executing contracts, managing the day job and moving towards consulting full time. (timestamp: 53m 15s)

I’ve been working with a client on a 3-month fixed monthly advisory engagement. We set out some goals before we started, and they feel that they’ve hit those goals and are happy with the results so far. Now I’m wondering whether I should offer a contract renewal at a lower price point (they paid for 3 months up front, which is coming to an end). They’ve been using my time less than I anticipated, and they don’t have much timezone overlap. How should I think about this next phase? (timestamp: 59m 15s)

Currently I’m getting work from designers that are struggling with development/code on web projects. The issue I’m running into that I’m usually brought into the project after it’s already under way and so I’m operating on a second hand budget/dealing (from the designer). In cases like this do you continue to interface with the client through the designer or would it be better to suggest that the end client reach out directly so you have more control over the project discussion (timestamp: 61m 33s)

I’m interested in re-launching my group coaching program. My gut feeling is that it will work best if there’s a clear focus so the participants feel each others questions are meaningful to them. I help companies make their Elm codebases more maintainable. I also help clients with my open source libraries that I maintain. Should I stick to one of those for the group coaching to avoid diluting it? (timestamp: 65m 35s)

Could I get a single page website teardown? This is fresh off the presses and exported to pdf from ulysses....but the timing was right! It may still be very drafty... (timestamp: 72m 23s)

Your Christmas-lights-email got me thinking about „need” vs. „want”. I thought I have to sell a „must-have”, not a „nice-to-have” But maybe I should I position my Brand Storyboarding as a luxury item? You don’t need it, but it catapults you to clarity like a Porsche? Would it make a difference? (timestamp: 1m 47s)

Would you recommend negotiating a consulting price list with a client at the very beginning of the consulting journey? Or the 3 tier pricing is set in stone once the proposal is sent to the client? Would it make sense to add a success reward to the consulting price in case the predetermined results are achieved? And last, on what principle would you even set a starting price (first tier) for Consulting services? (timestamp: 7m 23s)

Hi Jonathan! I’m currently employed full time and committed to making the switch to consulting. I’ve been thinking hard about verticals and I’m making good progress. I have a few ideas so far and would love to hear your thoughts on these and whether they’re potentially too narrow? 1) Fullstack web and mobile applications for health tech start ups. 2) Statically generated, headless websites for healthcare practicioners. 3) Headless commerce solutions for retailers in the health space. (timestamp: 14m 59s)

How would you price the service of validating a Saas product? (timestamp: 27m 10s)

Could you elaborate on your [content] strategy - who is getting notifications about Youtube lives through which channels? How is the content of the group coaching different from your Youtube lives? Do you tell your email list about the Youtube lives? If it is a list building strategy, you don’t have to, but OTOH they should be rewarded for being on the list, no? (timestamp: 31m 8s)

In “Learn your Lines” your answer to the 50/50 payment terms question revolves around not knowing when a software project is “done”. How would you answer that for a non-software project with a similarly flexible deadline? (timestamp: 36m 7s)

Jonathan, how do you break up your day between manager time and maker time when it comes to your professional obligations? (timestamp: 43m 17s)

Hi Jonathan, my +1 is a equine assisted coach (with horses) helping c-suite executive with a plateau in their leadership a coach/therapist in some cultures is kind of “tabou”. how would you approach inviting the right people for a monthly webinar ? (timestamp: 49m 40s)

I’ve already asked a question this week so feel free to skip this if there are others waiting... I’m aware this is a big question, but once I’ve settled on a vertical and positioning statement what are the concrete next steps to landing client 0? I’m right at the start of this journey and don’t yet have a public website, email list, linkedin network. I’m very confident in my ability to deliver, and my ability close once in conversation, but the marketing is ALL new to me. (timestamp: 54m 36s)

A potential client approaches you with a contract to work with them for a set amount of time (say 3 months or longer) without specific project requirements besides day to day feature work and improvements to an existing project (essentially you’re coming in to replace an employe). How would you approach this in the context of value pricing? The period is not necessarily fixed. (timestamp: 57m 11s)

I heard you talk about the importance of positioning many times, do you have a specific process to find ideal clients? (timestamp: 59m 50s)

what about if it’s not project with a fixed scope but it is ongoing service? - Example: I have a lead that needs product analytics for better product decisions. In the beginning, there is some work with strategy and setting up everything. Then they need someone to monitor and advise them on how to make a weekly/biweekly experiments to move the needle. Because product metrics is a living thing and they need an ongoing service. (timestamp: 61m 24s)

This was my first group coaching and it’s been immensely helpful! Quick bonus question if you have time: What about “Automated testing strategy for health tech start-ups?” I’d love this work and it lines up well with my techniacal expertise. I’m terrified that it’s so specific that finding the clients would be a massive challenge. “I help health tech start ups ship more reliable products with less bugs” (timestamp: 66m 15s)

Can you talk about your mindset? How do you pick yourself up when things go sideways and you feel like throwing in the towel and getting a “job” again? (timestamp: 72m 3s)

My target audience is Google Ads marketeers. I have an email list with over 2k subscribers that signed up for my lead magnet (Google sheet with links to free scripts). I send infrequent emails to my email list with either more free scripts, or tips and tricks to help Google Ads experts be more productive. I want to start the daily emails. Do you recommend creating a separate list where my current subscribers can sign up for the daily’s, or simply start sending the daily newsletter to the list? (timestamp: 1m 28s)

How to approach the specific customer you want to work with. They do not know you and your expertise, but you know you could impact one or more their business and experience metrics? (timestamp: 5m 53s)

I’ve tested the product of one company, and the fitness program truly works, but the web app experience is far from expectations. It’s unfriendly, and buggy and I see why people would not renew the subscription. My impact could mean to double or even triple potential client’s revenue based on a current business model (yearly subscription) and few number assumptions. What are the steps to getting this type of client? (timestamp: 12m 30s)

I’ve recently made the move to become more specialized in my domain and am about to launch a new version of my website with refocused positioning, new offers and various lead magnets. Given that inbound marketing takes time to generate leads, what are the most effective outreach strategies that you would recommend in the meantime? I’ve heard you mention on a podcast that asking for feedback is a good prompt but I’m curious to hear of others. Thanks! (timestamp: 12m 41s)

My question is related to the most recent tough love site teardown. Is there a way to test your messaging without a landing page? Putting together a landing page takes time and it seems like it’d be better to know you have a solid message before investing too much time in making another page. Related to testing your message is there a risk of changing this messaging too often and appearing scattered? (timestamp: 18m 37s)

Can you speak about a solo technical consultant using an administrative assisant for various tasks? Who should get one and who should not? (timestamp: 27m 24s)

How does a solo consultant handle vacation? (timestamp: 32m 37s)

I’ve been livestreaming every weekday this month. How can I best re-use the content that I have created? Any other suggestions around the topic of livestreaming? (timestamp: 37m 0s)

I want to do webinars (Brand Storyboard Café free mini- sessions) for lead generation. Should there be more info on this landing page? E.g. example drawings? How to spread the word? How to place the signup on my site without distracting from the main CTA? How to integrate it into a marketing flow? (timestamp: 43m 29s)

Is anybody doing webinars regularly? How do you get people to sign up? I could do these every week, or once a month. What is best? And how would it play together with e.g. Youtube lives where I would do basically the same, only that people can watch without signing up? (timestamp: 52m 36s)

What are your top 5 recommended readings to help us diagnose the types of value conversations that can be had? For example, I recall once you told me this sounds like they have a busted waterline and just need someone to fix it. I’d love to learn how to diagnose the situation more quickly so I can direct focus on better questions. I’ve read all of your books; all of Alan Weiss; Let’s Get Real, Implementing Value Pricing (Baker), and Positioning for Professionals (Williams). (timestamp: 60m 29s)

I have a client that is going through an ownership transition, and currently without a CMO. My agency is being tapped for on-demand strategic guidance and creation direction, however the client has shot down my offer of a retainer multiple times (they are paying on a per project basis). How do you feel about offering myself as a fractional-CMO type of role arrangement? How would you pitch a fractional-CMO role different from an agency retainer? - Thanks JS! (timestamp: 68m 24s)

I think you mention somewhere that you average $2,000 an hour and that your business is in the 7 figures. Can you give us a breakdown of your revenue stream and how your strategy could apply to someone doing technical consulting? (timestamp: 2m 17s)

I’ve discussed an audit of a company’s user onboarding flow with their head of product and they’re keen. What are some other types of services you’ve seen bundled with an audit to give them 3 options (good, better, best) in my proposal? (timestamp: 12m 35s)

I understand that value pricing can help you to avoid scope creep, but it’s not always suitable for all projects. After proposing a set price for a keynote & virtual workshop for a client, I realized that I’m getting in my own way of making the project profitable because of my quality standards/perfectionist tendencies. What are your tips for setting & holding yourself to quality standards that are realistic, don’t go too far beyond customer expectations and are tied to results? (timestamp: 18m 50s)

If the goal is to tackle more strategic, high-impact projects, what sort of opportunities and drawbacks do you see in partnering with other people (independents, agencies, etc) in the sales cycle (defining joint offers, selling together, sharing value) and on projects themselves? (timestamp: 29m 23s)

Do you have any references/tools for evaluating a market potential? As I am dealing more and more with just local businesses, I feel like it would be good to have a grasp on what the financial landscape looks like here. - Seems some are well off, others not so much - I’d love to know the “median” kind of thing. Unsure how to discover that, if even possible. Cheers. (timestamp: 39m 29s)

I usually do pre-paid gigs, paid at the beginning of the month. My most recent client wanted net 30. We negotiated net 7. Just sent them my first invoice and their AP guy replied saying they’d pay it on the 15th. I replied and told him CEO and I negotiated net 7and the invoice was due on the 8th. He replied telling me they pay vendors on the 15th and 30th. I haven’t replied to him or looped in their CEO yet. Thoughts on how to best handle this? (timestamp: 44m 40s)

I’ve had a couple wins recently in moving away from hourly billing. A couple of projects have been 100% up front and others I fellback to a 50% deposit, however I’ve realized this creates other problems. I realize falling back to 50% deposit was an attempt to mitigate risk on their part. What’s some language that I can use to help when asking for 100% upfront? I’ve considered offering refunds/guarantees to mitigate the risk for them but I don’t want to lead with that. (timestamp: 49m 47s)

How to do a value based pricing for a solo-entrepreneur at the very beginning stage of the product, where validation is needed. The outcome of performed experiment can confirm or reject the hypothesis, or it may even turn out that the product can pivot with new data, which means that the work will be extend from the initial deal. (timestamp: 58m 1s)

Do you have any tips for how to improve with meeting facilitation? (timestamp: 1m 47s)

I have been a back-end /devops web-dev for quite a while, working mostly on either large ongoing projects, or as support for teams of developers. This means I have gotten sunk into trading time for money as this is the most common paradigm for this kind of work and its difficult to assign value when my role is so removed from the actual work being done. My question is, what steps can I take to start interfacing with clients firsthand, when my skillset has little to do with their perceived needs? (timestamp: 3m 32s)

When you’re in a sales call with a customer who is looking to create a new product, should you try and value price the whole project or just the first phase of an engagement? i.e. if I decided that a sensible first step would be to build a prototype, should I value price that? Or is this where a productized service makes more sense? And then following on from that, once you’ve delivered a prototype, should I value price the subsequent phase? (i.e. an MVP) (timestamp: 9m 18s)

Looking for ways to do get more eyes on my social media content. Would it be a good idea trying to start a video series of “Show”-Storyboarding sessions with interesting people? So they get to talk about their newest product for half an hour, and I get to show off my storyboarding skills. Most likely they already have figured their messaging out, and it wouldn’t be so much consulting from my side, but more a sketched exploration. (timestamp: 19m 5s)

Can you go over the benefits of daily emails? Both, benefits to you and benefits to suscribers. (timestamp: 22m 41s)

I have a client engagment with a unlimited access advisory retainer, who was my previous employer. The issue is, they are only using me about 1 hour a week. I have offered to review data, help to arrange organize experiments, help in strategy, but hardly any engineer has taken me up. I’m still treated like I was when I was an employee, in terms of authority. What can I do to deliver more value? I’m concerned that they will end the contract because of lack of need (atleast how they see it). (timestamp: 38m 40s)

What are the reasons why leads would ghost you after an introductory call? How can you avoid this? Also, how do you get a reply from busy decision makers? (timestamp: 40m 10s)

Update Copy for a Lead Referral Page: my largest source of leads is an “Experts” page on a software’s website. There is a list of 10 consultant links, which will open a sales page. I am struggling to come up with the right length, structure and detail to present on my page. The page will have a CTA linking to my site. (timestamp: 45m 45s)

I’ve been working on my 1-liner formula: I am DISCIPLINE who helps TARGET MARKET w/ EXPENSIVE PROBLEM unlike my competitors UNIQUE DIFFERENCE. I’m stuck on the EXPENSIVE PROBLEM part. How to make it clear that this problem you have is expensive so that I can solve for that. Is there a talk, webinar, podcast where you go into some detail about that? (timestamp: 51m 23s)

I’m told that I should have a “signature” offer. It’s a fixed-price, fixed-scope, productized or packaged service that’s unique and sold at a premium flat rate. Signature offers are often sold as standalones. But do you recommend a three-option proposal preceded by a “why” conversation still? Or is it necessary since it’s well-positioned, practically presold, and can often be purchased in a single step (like via a “buy now” button)? I’m thinking of an audit-roadmapping bundle using my IP. (timestamp: 55m 14s)

I am planning to start a “gold” level engagment with a client. Basically, I am supposed to give them all I got. Any tips on how to manage this type of engagment? (timestamp: 59m 2s)

How to price an idea for groundbreaking concept for a global brand (high class hotel chain)? They haven’t asked for it - it is my initiative, I would reach out and pitch the concept. (timestamp: 68m 47s)

Do you see a benefit in setting standardized pricing for creative services, kind of like when you productize something. My video productions rarely go above $800. My web design projects teeter around $1500. (I’m certain I charge too little). Rather than come up with value based proposals for individuals, just have a range of preset options for people. (Easy pricing?) (timestamp: 82m 20s)

How you think about pricing roadmapping sessions for an MVP build. The deliverable is a set of requirements and wireframes. I find that clients don’t have a good handle on the value of their MVP. Their “billion dollar idea” hinges on it succeeding, but it might fail. Seems like knowing the value of a working MVP would determine the price of a roadmapping session. If that IS how you think about pricing the roadmap, how do you determine an MVP’s value to come up with a good value-based roadmap price? Or if you think about pricing the roadmap in some other way, can you share how you think about it? (timestamp: 86m 32s)

Hi JS. I’ve recently invested in developing my first white paper resource (ie. a lead magnet) that targets my primary buyer (ie. CMO of an eComm brand using Shopify). What are some tips on getting the most mileage from this type of resource as it relates to a LFPS? (timestamp: 1m 40s)

I have heard you suggest to write the project value into the proposal, to anchor high against the project price. However I don’t think this is in your proposal template. Do you recommend always doing this? (timestamp: 9m 1s)

I find it easier to have a value conversation when my clients have a problem, versus when they’ve identified a new opportunity. This maybe because I can diagnose the level of pain with an existing problem, whereas a new opportunity is completely unknown. I assume your approach to both situations is the same (Why conversation). But can you offer any tips on how I can frame this situation differently? (timestamp: 14m 28s)

You recently answered my question about value pricing. One comment you made was “you can price on size of company, type of watch the buyer wears etc.” Can you explain how? Is it as easy as saying “bigger company, higher value”? (timestamp: 21m 19s)

How can we develop relationships that lead to knowing about upcoming projects, before large outsourcing firms get involved? What ways have you found yourself eligible to be on a company’s vendor list? (timestamp: 27m 18s)

Is there a ideal set of questions (or outcome goals) to have in mind during the market research interview rounds? (timestamp: 33m 48s)

What’s the best way to find ’dumb money jobs’ as you adviced last time, that would still relate to the field and skills that I’d be willing to build my business around? ( design in my case). Last time you proposed to do Fiverr&Co,, but that also requires pretty demanding resourcses in terms of marketing and time there a ideal way I could for example reach out and propose myself to agencies? (timestamp: 41m 53s)

Trying to just answer the “WHO DO I SERVE” question. Where I am at is: My business is mainly creative services (videography, photog, and web design), but I also handle some digital marketing tasks for clients (email, social media, etc) There’s no one vertical I do this for, nor do I have a desire for this. I much prefer to work with local people and meet with people even though it might be a little less efficient than being a virtual content creator for businesses. My clients are in either contracting, restaurants, and service professioanls. The one commonality between my favorite clients are they understand the internet just enough to know its value in it but no where enough to understand “how to use it for their advantage”. They’re happy to pay someone (me) to be mostly hands off, with some input to the creative. Honestly, this all kind of works for me. I get a healthy amount of new leads each month with zero advertising or cold calling people. The reason I’m trying to figure this “WHO” question, really only is to make it easier for ME to create content for MY business. I’m all over the place right now. (timestamp: 50m 7s)

What are your thoughts on using your content to help educate the buyer on the value of your services? I’m a vertically positioned management consultant (ad agencies), and I have a platform speciality. I deal with software implementation so the “costs of implementation failure”, or “the value of an erp system”; or education about metrics and benchmarks (“Gross Profit per employee should be $150k”) so that they may have a clearer valuation prepared. (timestamp: 1m 21s)

If the value of my services are upstream and I can’t define a financial ROI for my services, you recommend pricing feelings instead (eg. customer satisfaction). In this scenario, how do you determine project value with the Why questions? (timestamp: 8m 31s)

It seems like to build authority, capturing and managing ideas is essential. How do you get good at capturing ideas as you have them, and nurturing them to become part of your toolkit, your content, your reference material, and your products? What kinds of workflows and techniques have helped you? And how do you manage your Big Ideas? Do you keep them in a specific place so you can refine and re-use them over time? (timestamp: 17m 59s)

It seems to me that self-worth is a huge barrier in raising prices. Do you agree and if so, how would you coach someone to realise their limitations are self-imposed? (timestamp: 27m 15s)

What’s the best practices you’ve seen implemented by people successfully pursuing the psychographics specialization in terms of nailing it down properly and keeping ’scanning’ for prospects? And is it a sensible move for someone in a situation of needing to earn in the short-term, or better staying with a easier specialization and then rethinking it psychogs when financial pressures loosen up? (timestamp: 35m 8s)

When I see a job description which might seem like a perfect role for me, how do I convince them that it’s best to outsource it to me on a contractual basis, rather than keep it in-house. Especially when the company says things like they want someone who will want to grow with the team and with the business? (timestamp: 47m 31s)

How can I overcome the sometimes endless litany of technologies that appear as a requirement for a role? On the one hand, I don’t want to be the cook, the bottle washer, and the waitress. But at the same time I need to show enough depth about their problem. If I start taking tech tools I’m experienced with off my list, will I not lose on potential opportunities, looking for something that doesn’t exist? (timestamp: 53m 38s)

Technical setup question: How do you syndicate your daily posts to both and your mailing list? I’d like to reduce the barrier of publishing to my mailing list, and also would like to give subscribers a way to link to useful posts, so I’m curious about your setup there. (timestamp: 58m 44s)

I’ve been working to build my design advisory homepage using your Perfect Sales Page framework. I’ll not be able to join the call, but I’d love a review of where I’m at with it. Yet to be added, client case studies and more testimonies. Each product offer would have a sale page in the future. (timestamp: 62m 35s)

I am trying to create a short video course to teach my audience of Google Ads experts how to use Javascript to automate parts of their work. I have never created a video course before. Do you have any recommendations on the most effective way for me to learn how to create and distribute such a video course? (timestamp: 1m 8s)

I run a digital service agency, focused on building custom web solutions for eCommerce d2c brands and now in the midst of a shift to value based pricing. What advice do you have for structuring ongoing website maintenance plans for clients that originated on an hourly billing model? How do you feel about offering tier’s of maintenance plans (1. On Demand 2. Prepaid blocks 3. Monthly Retainer)? - Thanks for your help! (timestamp: 6m 30s)

I’m tired of doing the type of tech consulting I used to do, but at the same time I don’t want to feel like I’m starting from the bottom with offering a different service. How do you suggest going about repackaging myself to solve different problems a software organization might have? (timestamp: 10m 51s)

How can I enlist the services of someone who would act as my account executive who can help build relationships with software development and operations teams? (timestamp: 23m 53s)

Is there a scalable service that you found can be done for more than one software organization at a time as a client? In other words, I want to move away from the dilemma of one big tech client sucking up all my oxygen in terms of time and mental energy. (timestamp: 25m 39s)

Please describe your process for time management: personal, family, personal development, client delivery, as well as learning new things to make you more effective at your business. (timestamp: 35m 53s)

A client reacted positively to our presentation and said he was going to push his organization to accept our most expensive option. But when I sent the 24-hour deadline reminder he replied: “I am definitely not going to be able to have an answer on this before then so we will take our chances. I will have a much better sense of things at the end of next week.” I haven’t heard back yet. Do I risk coming across as desperate if I offer to give the presentation to his colleagues? (timestamp: 40m 47s)

If you’re giving a live free webinar and want to make an offer towards the end, what main points would you want to hit, so that people are primed to enroll at the end? (timestamp: 51m 14s)

We have a “have a meeting with us” in our page for prospecting, but we have many customers that just want to talk with us because we are relatively known. But they dont have the money for our services. Its a good idea to have a digital form with “screening” questions, to only incentivate qualified prospect? even showing some price ranges, so they think before asking for a meeting? (timestamp: 54m 8s)

You sell private coaching to professionals wanting to level-up for $10k/4mo. Your demo proposal for BigCo sells coaching to a big company for up to $12k/mo (4x+ more expensive). We’re planning to sell coaching to our clients who spend 10M+ a year overall. Did your Bigco spend more/less than this? We’re trying to find a sweet spot for pricing (not just cover our costs, and trying to be happy even if the client just goes for one round whether that’s 1,2,3 or 4 months). (timestamp: 58m 47s)

I’m experimenting with your suggestion to use the following pricing options to write proposals: 1) I’ll create a plan and find someone to do the work. 2) I’ll create a plan, find someone to do the work and oversee things. 3) I’ll do it for you. In option 3, I’ll still be outsourcing to juniors and managing the process. Which means options 2 and 3 feel very similar. Can you help me reframe this to see the differences between options 2 and 3? (timestamp: 1m 42s)

Can you explain the difference between using roadmapping as a loss leader versus delivering roadmapping as a valuable standalone productized service? (timestamp: 6m 53s)

I now understand the difference between specialising (me) and niching (them). If you choose to focus on a specialism, is there a way to tie your content marketing to business value? Or is focusing your content marketing on your specialism more of a “hit and hope” strategy? (timestamp: 12m 36s)

I help Elm devs succeed by advising them on design techniques, craftsmanship practices, and support on tricky problems. I’d like to re-launch my group coaching program. My group coaching was valuable to clients in the past, but I dropped it because the logistics were cumbersome. I like the idea of crowdcast as a platform because it gives an easy way to submit questions in advance so there’s no fuss over rescheduling. Can that that format can be effective for highly technical topics? (timestamp: 18m 39s)

Is there a tension between offering group coaching to individual developers, and other services to teams (advisory retainers, training). Am I splitting myself between two groups to serve, or can this be in alignment? Individual devs tend to focus on more tactical questions. I focus on a lot of the same techniques and habits with both. Maybe it’s a question of framing the individual services to be of strategic value? (timestamp: 24m 40s)

I am trying to grow my email list, The audience is Pay Per Click experts. What strategies have worked the best for you to grow your email list or would you suggest? (timestamp: 26m 33s)

I send mini articles to my mailing list subscribers. Some articles are potentially interesting to other people. But for now I am not publishing these articles on social media, because it seems to me that this content “belongs” to my mailing list subscribers. On the other hand, mailing list subscribers were already the first to read my articles. And it’s not scary if others read it a month later. How do you solve this dilemma? (timestamp: 30m 20s)

Your newsletter emails do not contain “Share to Facebook, linkedin, Twitter” buttons like Seth Godin does in the newsletter. In theory, such buttons allow the subscriber to spontaneously, in one motion, share your letter and expand the audience of your mailing list. Is there any reason why you shouldn’t do this? (timestamp: 36m 5s)

It’s easier for me to meet clients for 2-5 sessions than for a multi-month project. Either I solve problems effectively, or I don’t find long-term projects. Can you recommend books or articles that have been most helpful to you for organizing your 4 month coaching program? Or maybe some kind of online course? You seem to have mentioned that some Seth Godin course was helpful to you in organizing this group format ... (timestamp: 37m 48s)

How do you feel about including one illustration every day, if appropriate? This means, for example, engravings, the plot of which well emphasizes the idea of the letter. Given the high frequency of emails and the weight of emails, is this overkill or a good idea? (timestamp: 42m 1s)

LFPS tear down request: -I help the ad agency owners transform the way they work so that they can scale their operations for growth without bleeding expenses. We are different from our competitors because I only work with Workamajig. It’s the best tool out there and I won’t work with less. (timestamp: 43m 32s)

Would you recommend advertising your services or products at the bottom of every daily email? The argument is for availability, that is, for a potential buyer there is no barrier between his desire to buy something from you and the need to look for a link. The argument against it is that it looks like an intrusive selling, and that customers don’t notice the ad that is repeated every day. (timestamp: 51m 26s)

Is it possible to find a long-term project that fits the ideal of value pricing AND does not have the end client dictating deadlines? (timestamp: 53m 26s)

Does it help to create a video sales letter to prime a potential client like CTOs for the sales conversation? (timestamp: 58m 39s)

How did you choose the (minimum) duration for your private coaching product? I noticed you’ve tried at least three different durations (3, 4 and 6 months?) Which duration has worked best and why? (timestamp: 60m 48s)

We got a lead that can only afford 1/5th of our minimum engagement price. So we cannot work with them. But they do know people who we might want to work with in the future. How do you turn away a lead like this softly so that they will still want to recommend you to people who can actually afford you? (timestamp: 64m 31s)

You make a free 30 minutes introductory call with a potential client. There are no grounds for a value pricing project - a maximum of one or two sessions. The client specifies how much it costs. Do you call $ XXX per hour or per session and specify if this amount is within his / her ability? The client confidently says “Yes, of course” and asks for a link to book a session. And then the client disappears. How to think about it? (timestamp: 67m 32s)

The first call with a customer usually lasts 40-60 minutes. It is very difficult during this time: a) to exhaust his verbal flow, b) to go through 3 questions “Why?”, c) to evaluate the value of solving his problem, d) to evaluate the amount of my fee, e) to test the client’s willingness to pay the maximum and minimum price. Does this skill come with experience or should you divide such a conversation into 2-3 calls? (timestamp: 0m 57s)

For various reasons, I’ve not done great at building personal relationships at work (professional, yes, but personal, VERY limited). This is mostly because I didn’t want people to think I’m trading on these personal relationships to get ahead - especially since I’m a woman and a minority. I preferred to let my work speak for itself. Given that so many consulting opportunities are not obvious, and they often depend on personal friendships, what are my options to approach potential clients? (timestamp: 8m 40s)

I help IT entrepreneurs make critical business decisions faster. I offer two extremes — a free checklist/mailing list and expensive customized 1:1 individual/group sessions. I plan to offer a Group Coaching format for young entrepreneurs similar to yours (biweekly video, Slack, etc.). If you were me, how would you launch such a format? Specifically, which main mistakes you would avoid, and what would be your main focus? (timestamp: 15m 42s)

On your advice, I launched a daily newsletter. I am pleased with the first results by the number of subscribers and like the process itself (I regularly write long articles). However, I am worried that creating 1 letter (250-350 words) takes 2-3 hours every day. How long does it take you to create 1 email on average and how much has it decreased in the first year or two? (timestamp: 22m 12s)

You have been practicing the format of a 3-4 month individual coaching program for a long time. Many students have gone through it. Could you share if your program has a common pattern of what and how you are trying to achieve with your client? What 3 typical mistakes would you warn us against when launching such a program? What should be the main focus here? (timestamp: 29m 28s)

The client needs your advice in preparation for an important deal. You offer a fixed $X with 100% prepayment for 5 sessions of 1.5-2.5 hours during the month. The client says he has difficulties with the cash flow. He calculates that you offered $X for approximately 10 hours, which is equivalent to $X/10 per hour and offers to pay for each session separately. You so wanted to move away from hourly to value payment, but the client drags you back there. What would you do? (timestamp: 36m 16s)

We’re going to start doing a slide deck before we deliver our written proposal. Do you have a go-to guide or SOP for presentations? Also, would you include pricing in a presentation or reserve that for the proposal only? (timestamp: 38m 35s)

I am educating my audience of PPC experts on the use of scripts (javascript) to automate parts of their work. A big chunk of my audience wants to learn the basics of javascript in the Google Ads context (Google Ads javascript API). Currently I am sharing my knowledge through my blog and offline training. How would you decide on “the next format”? Should it be a book, video course, online workshop (webinar), or something different? How to choose? [sorry, won’t make it to live event] (timestamp: 44m 20s)

Which positioning statement seems more clear & useful to you? A. “I help B2B SaaS companies land more demos & trials” vs. B. “I build B2B SaaS sites that turn traffic into raving subscribers.” (timestamp: 46m 45s)

Some subscribers to my mailing list have informed me that the emails fall into the Advertising or Spam folder. I also see that some subscribers have not opened any emails. Perhaps for the same reason. Of course, you can ask subscribers to put my address on a white sheet, but as far as I understand, this is done differently in different e-mail systems of the ISPs, it’s not always obvious and it’s not the fact that people will figure it out. Do you solve this problem somehow? (timestamp: 49m 6s→)

In the first weeks of open mailing it was about 45%, and a month later with the growth of subscribers it fell to 20-30%. The quality of content has not changed, grateful feedback comes regularly. Is this a normal trend or should something be done in your experience? How have your indicators changed over the years? (if, of course, it was important for you). (timestamp: 52m 18s)

Is this a good LFPS: I help hyphenated American professionals to make the leap to entrepreneurship by focusing on 5 essentials. Unlike my competitors, I built a high six figure career and a high six figure business for more than 10 years before I became a career and business coach. (timestamp: 55m 50s)

I am afraid to promise within the coaching program 24/7 the client’s access to me, even with reservations (I answer the call within 90 minutes, the email within 24 hours, etc.). Therefore, I have a desire to either not promise such access, or put a very high price on the coaching program. What is the dynamics of customer calls to you as part of your coaching program? You have not been overloaded? (timestamp: 59m 47s)

How to overcome the fear of approaching certain decision-makers because of their title, even though I’ve had senior titles as well. (timestamp: 63m 51s)

Is it too much to have two niches, one for my tech consulting business, and a slightly different one for career/business coaching? (timestamp: 68m 26s)

I had a client ask to delay our scheduled discovery call 40 minutes before the meeting. They would like to schedule for the next day. This sounds like it should be a red flag for a difficult client. Would you recommend taking the call or not? How would you respond? (timestamp: 69m 54s)

Which positioning statements sounds stronger: a) As a Business Therapist, I help IT entrepreneurs navigate in non-standard situations faster. Unlike others, I provide an interdisciplinary view. b) I help IT entrepreneurs make critical business decisions faster. * - non-standard means shareholder conflict, entering a new market, founder burn-out, etc. ** - interdisciplinary means that I combine various modalities (business consulting, psychotherapy, Theory of Constraints etc.) (timestamp: 72m 45s)

Sequencing the Why: do you always use the Why in your first call, or do you qualify, then conduct a second call for the Why? What if you can’t get the Why answers you need during the call? Just set up another call and try again to dig deeper? (timestamp: 1m 40s)

What are your thoughts on scheduling follow-ups? There seem to be 2 projects within a big software project: the project itself, and the project of getting the project started. I’m usually VERY lenient about follow-up convos (they seem really salesy), but I’m losing deals left and right because prospects are either (1) overwhelmed by the options and want someone to guide them, and (2) my competitors are scheduling follow-ups and building more rapport with them. (timestamp: 7m 33s)

Do you have any best practices for getting in touch with the real decision-maker? Recently had a “why” convo with a CTO -- I was a really good fit for the project, but they didn’t want to put me in touch with the CEO (who would ultimately make the decision). Of course, he bailed on our follow-up call and they picked another provider (probably the one that got a hold of the CEO lol). (timestamp: 20m 1s)

How do I apply value based pricing to a project with hourly costs? Value based pricing has worked well for consulting, but I now want to apply it to a software implementation project. I have a new client, trust is high, and they’re great about accepting the costs presented if they understand the pros and cons of each option. They’re re-launching one of their SaaS platforms, and they need to take payments. So the value of doing the project is high. The existing platform is a mess, and there’s a lot of remediation to be done to take payments and apply subscriptions in a secure manner. And they understand that’s necessary. There are multiple payment solution options, depending on how fast they want to deliver vs what features they offer to customers. The client most values being able to weigh the cost of implementation vs the business value and they (now) value higher quality delivery. I don’t want to present a “$x per month for a team of 3 (my staff are paid hourly) and we’ll do whatever you want for as long as it takes” proposal, it’s how the previous vendor lost the work – the client couldn’t see what the cost of a project was before committing to it, and it could take months to deliver. Do you think there is a value proposition to differentiate the options - beyond just “this is cheaper to implement/this is cheaper to run/this has more features”? Is there a way to price/present the options to cover the risk of budget-overrun given the ‘unknowns’ of the inherited system, but only if needed? (timestamp: 28m 39s)

One of the products on our ladder will be to offer Hotels new websites. It’s a competitive space as many of the booking engine providers offer websites for free - but the sites are what you would expect. My thinking is we offer 2 options: $$ option - Monthly Subscription - Using our custom WP Template - $1000 a month min 24-month contract. (We have a team member that would be doing this work, not me). $$$ option - Custom site What do you think of a website subscription model? (timestamp: 41m 50s)

On your sales pages you have sentences like “The price is $xxx, which distinguishes those who are serious about their business, and is easily recouped through the reduction of manual labor and increased profits.” I don’t often see phrases like this justifying a price point. Why do you do this? What is the difference compared to just stating the price? Is it working for you? (timestamp: 47m 24s)

What if the client wants to hire you before you have the “value”? I had the “why” with the stakeholders but didn’t fully drill into the business case to arrive at their perceived value. I followed up recommending any of: a) diagnostic (review their system), b) a “process observation” (diagnostic), or c) an additional, free discovery call to continue the “why”, inviting the owners to join. I received this respons: I must be honest, this seems like a pretty straightforward proposition…are you willing to provide immediate training to help us address what I consider to be remedial needs? If so, I think we can quickly move forward based on the “wish list” Michael shared with you. After that, once we have the basics shored up, we would be open to a discussion on larger, structural elements. (timestamp: 50m 15s)

Most of our services, are codesigned with the clients team. But we believe there are some products that are a standard pack (ecommerce, mail automation, on boarding) that will probably will work better with no intervention from the client’s team (specially because they are part or the problem) how can we build the offer without looking that we are avoiding their team (which we are). More specifically, the question is, how do we design and price a product without our interaction, without lowering our prices? Being a productized service, the customer can think it will be cheaper, but we think we are packing our knowledge and reputation. (timestamp: 55m 50s)

Do you ask old or existing clients to recommend your services to someone they might know? Do you send letters to your old clients to “raise them from the dead”. e.g.: “I liked working with you on project X. I’m curious, is there anything I can do to help your business grow?”. (timestamp: 2m 11s)

During the value conversation, how do you ask questions about the expected monetary value of future business improvement without being perceived as if you gather too sensitive information? Did any prospect get nervous/suspicious that you will charge a higher price if you know more info about his/her potential gain? Because at that stage you are still a rather stranger to them. Plus nobody asked them such value questions before. Maybe they never asked those questions to themselves. (timestamp: 5m 17s)

Could you please elaborate more about your mailing daily practice: How far in the future you have emails scheduled? How do you find inspiration when you feel stuck? How do you manage to avoid overwhelming people’s minds inbox? Do you have some heuristics for daily mail: maximum number of words, bad ideas, home-run lessons, etc.? (timestamp: 11m 15s)

You once said that you simplified your email list logistics and now have a basic Orientation course (VBT, FPS, 7 emails with articles) followed by fresh daily letters sent to your entire list simultaneously. Don’t you feel some regret that new people miss your great old daily posts? Yes, I noticed that you also publish them (via automation?) on your website, but does this content have any other usage apart from the email option “View on the web”. (timestamp: 17m 4s)

I’m wondering why you don’t maintain a minimum activity on Facebook, Instagram, Twitter, or Telegram? Why not use them at least as a promotion tool for growing your mailing list? May be your potential clients don’t use these channels? Or given your existing client base plus podcast, plus guest podcast activity is more than enough for your business now in terms of lead gen? (timestamp: 25m 7s)

What’s your position about when to send your daily broadcasts to ensure they are indeed being read by subscribers? E.g. not sending email on Sat/Sun? Or sending emails early in the morning? Does scheduling consistency matter for building your predictability and hence trust? (timestamp: 26m 26s)

Do you automate 3 proposal reminders (before acceptance) or just set reminders for yourself to send them out? Sometimes I forget and my clients can sometimes be busy too so I feel like I need to have some process here whether it’s automatic or not. (timestamp: 31m 0s)

could you demonstrate how you use Trello for client tracking/CRM tasks? (timestamp: 35m 31s)

How strict are you with proposal expiry dates? Or does this completely depend on the project? Any minimum ‘cool-down period’ if someone misses the expiration date before you consider talking about the project again? Or just depends? (timestamp: 42m 30s)

If you didn’t have your podcast and you were starting your list - or when this was true for you - how do you get initial traction on your list without constantly spamming LinkedIn, FB, and Twitter? (timestamp: 48m 18s)

If you feel like you’ve outgrown a client, do you still try to assess whether they still want to work with your new prices before letting them go? Have a client that needs work done that actually helps them convert customers (and they know this) but I have a strong feeling that they are still the champagne taste & beer budget type. (timestamp: 56m 14s)

How do you deal with a client you have outgrown that is not really that pleasant to work with (e.g. low budget, not too respective of your time/start date boundaries). Can you really refer this type of client to anyone you want to keep a good relationship with? Or do you just say “good luck, bye”? Currently I’m basically ghosting them / not replying, not sure if that’s the best way to deal with this. (timestamp: 64m 37s)

We are a business design consultancy as IDEO. We usually do high cost consulting (from 15 thousand dollars upwards). We have a show on the web about business and technology that has quite a few viewers, and many of them want to have a “little piece” of us, and can’t afford us. How can we design low-cost products like courses without devaluing our high-cost products? (timestamp: 66m 49s)

I am inspired by your product ladder with your productized consulting services. I am considering to offer similar services. What do you like the most about these type of productized services? What do you dislike about them? Would I be better off with offering an online course instead? (I love travelling and my freedom to organize my working days on the go. A lot of your products seem to require tight schedules in your calendar) (timestamp: 74m 53s)

I have 2 new clients and 3-4 current clients I am moving to Retainers with weekly meetings. I’m trying to price this with options for unlimited support email, the periodic call, and finally an option for direct 24/7 cell phone access for CEO. They are all currently paying $200-$250 hour. Trying to determine a good starting point for a quarterly retainer, understanding there is a premium for access. (timestamp: 87m 52s)

How do you handle situations in which you set a time to follow-up with a prospect via phone, and they cancel at the last second, without suggesting a new time? (timestamp: 104m 56s)

How do you know when to call it quits on a marketing campaign? (timestamp: 105m 56s)

If you have time ... would love to get your spontaneous reaction to my website ... I enjoyed the “tear down” last time (timestamp: 109m 57s)

My previous projects have all been in the $3000 to $8000 range. With that pricing, just sending over a proposal always seemed enough. However, I’m about to send over my first $30k+ proposal, and I’m wondering if a proposal is enough. Are there other documents you recommend I have the client sign as well? Right now, I’m using your TPS proposal template. The project is developing a web application, if that matters. (timestamp: 1m 37s)

In previous group coaching sessions, you’ve said it’s important to determine some metric that can be tracked while we work on the project. I feel like I’m having a hard time wrapping my head around this concept, though. I know this will always depend on the client and should be determined with them, but could you come up with some examples of things you could track? Like for a web app, or a website redesign, or rewriting a website’s copy. (timestamp: 9m 40s)

How do you respond when prospects get angry at you for asking “why” questions? (timestamp: 20m 11s)

We are a business design consultancy (ideo style), which helps companies to implement digital transformation, through rapid prototyping. Many of our services are quite custom. However, we would like to have some productized services, easy to implement and of a small cost (about 1k - 5k). We couldn’t have an idea of what to do. Our expertise is in agility, business viability analysis, service design, user story, user experience, metrics and rapid prototyping. (timestamp: 28m 58s)

What are some simple scripts to use when clients start asking for work that’s in a level of engagement deeper than what they paid for? (timestamp: 38m 46s)

If you have time on the call, would love to know why you chose Moon Clerk. What are some things to consider when choosing a payment system like this. I looked into using it but there’s no way to have tax automatically added based on geographical location which I need to charge legally. (timestamp: 48m 12s)

I attended your positioning statement workshop a while back and loved it. I was wondering if you could give specific examples of how you take the statement and apply it to other marketing assets? I think I’ve perfected my statement, and am now rewriting my sales page. I can’t directly see a positioning statement in your perfect sales page example, or your Linkedin profile... In short, I’m interested to know how the positioning statement fits into the overall messaging strategy. Thanks! (timestamp: 1m 47s)

We want to make an introductory program to our digital transformation methodology called “pandemic digital transformation bootcamp”. 3 sessions with a slack group where we will adress: 1. agility 2. leadership and teamwork 3. prototyping and rapid development. It would be free of charge, so that later they would want to buy strategy and coaching. Target audience is CEOs, COOs with whom we have good networks, is it a good idea? would you do some tweak? how do we transform them into customers? (timestamp: 17m 32s)

We are a business design consulting firm (similar to IDEO), but there are only two of us. What happens when we have 3 big clients that will occupy the next 3 months? How do we sell to prepare the future without accepting new clients in parallel? (timestamp: 28m 33s)

I’d like a teardown on this draft of our new landing page. The target audience is dev leads for Laravel product teams. (timestamp: 38m 8s)

... if we have time :) ... We’ve built a landing page that sells custom project work. How would you go about offering related productized services. These services are usually initial phases of every custom project we would do anyway and are bundled in the project. Phases like: 1. Assess readiness, 2. Discovery, followed by PoC and further development. - Can all that be on the same page? How would you connect it? Do you have examples? (timestamp: 60m 20s)

Any ideas on finding ’watering holes’ where CMOs or CTOs hang out? Reddit and FB seem better suited at targeting a B2C crowd (who may or may not have real money to spend), - There are some Linkedin groups that seem to target these ’C-suite’ players in their titles, but they mostly seem to be spam fests, accepting anyone who requests to join, with no real community engagement. - I’m guessing that in ’normal’ times, live conferences are the answer. But are they congregating anywhere online? (timestamp: 1m 26s)

What are some pointers on writing less abstractly? (timestamp: 10m 14s)

Would it be uncouth of me to offer free strategy sessions (no sales slant) to Black startup founders during this time as a way to support with action? (timestamp: 17m 44s)

What do you use to keep track of long-term goals or chart out how to reach those goals? We have long-term goals like publishing a short book, speaking at conferences, and other ways to raise our profiles. Have you found a system or bit of software that helps to keep you accountable? (timestamp: 20m 54s)

Can I get a site teardown for the site I’m working on? Trying to get the right balance of being clear on who I’m trying to help vs what I can help them with. (timestamp: 31m 17s)

I took the advice from the last session about our innovation design firm. I have a new proposal of a web page, and we designed 4 products for CEOs and COOs. Caould you check if its clear enough? (ennglish its not my native language, and the original page is in spanish, I translated it for the session. (timestamp: 46m 12s)

This is my draft/sketch for our Machine Learning Experts Landing page. Can you please do a tear-down? My concerns is that so much text makes it sound like TV Shop commercials. (timestamp: 62m 10s)

How do you approach offering a new productized service as a “beta”? Context: I’ve been having difficulty getting folks to buy my conversion audit (fixed @ $5000 for everyone). Lots of people ghosting me after being “all about it” on the phone previously. I’m suspicious that there’s a trust problem somewhere and I want to get more specific testimonials. But, the audit requires a huge time commitment from people, and I think giving it away for free will be a harder sell than charging (because they’re not invested & they see it as “cheap/not worth it”). (timestamp: 1m 7s)

Positioning statement for review: ‘I’m a sales copy, case study, and white paper writer for SaaS companies struggling to build credibility with large enterprise clients.’ Is ‘SaaS’ too broad of a niche for marketing consulting services? If so, should I narrow my focus to something like healthcare or EdTech? Right now I’m in the trenches writing B2B tech copy and content (on Upwork, lol) but would like to eventually do more big-picture strategic communication/branding consulting. Looking to focus and learn one market well. Any other market suggestions would be highly welcomed as well. Please and thank you :-) (timestamp: 8m 57s)

Do you have any do’s/don’ts for pursuing leads who are also friends? I’m concerned about under-pricing myself with them, or possibly putting the friendship at risk if the working relationship goes awry. (timestamp: 18m 2s)

Positioning statement for review: “We are a technological laboratory that helps managers of highly competitive companies to optimize their operations, improve their sales and innovate in products and services. Using rapid development methodologies and technology, we implement functional prototypes in weeks instead of months, we transfer tools and speed up your teams so that the organization can continue on its own.” Giving our service is something as a “magical promise” (solving a problem and prototyping in weeks), how to make leads to try us out? Finally, We are very good on the detecting problems but those problems are not necessarily the one the client has detected as a problem. I know from your writings that we have to focus on what customer pain is, but what if we resolve the problem he is fixed on... the real problem still exist? (timestamp: 21m 32s)

I’d love a mini-teardown of the landing page work in progress I shared. Is the target audience too broad? Do the pains resonate? Should we just use the FixMyF**kingProject site? :D (timestamp: 47m 0s)

Finally posted and setup my monthly office hours session... can I get a review/feedback of the post and landing page? Goal is to get people into a funnel for the mailing list and security coaching community. Thanks! (timestamp: 55m 2s)

What changes would you make to the “Beta Service Invite Email Template” from TPS for cold outreach messages on Linkedin to get beta testers? Trying to figure out how to balance the curiosity-inspired “you look interesting” kind of messages with asking something of them. Pretty sure I have serious aversion to coming off as salesy. Every variation of what I type out feels forced Variations: “I’m launching a new Customer Data Review service and looking for beta testers. If you’re interested could we have a quick call?” “I’m looking for people to beta test a new “Customer Data Review” service I’ve put together. If that sounds like something you’d be interested in please let me know and I’ll send over times for a quick call.” And then some tweaked version of the full template from TPS but not sure if that’s too long. (timestamp: 63m 32s)

We have a client that has a retainer where they can opt for maintenance (just updates and security) or sprints, which includes development work. They’ve snuck in little requests for fixes while only in “maintenance mode.” We don’t want to send them little invoices for $1k or $5k. We’ve thoughts about resolving this by getting them to pay for the development in advance, paying for a year of maintenance in advance in exchange for little fixes be thrown in. (timestamp: 71m 15s)

How do you handle the first conversation you have with prospects after COLD outreach? (usually only 15 mins) (timestamp: 1m 14s)

Do you have any suggestions for client exit interview questions or questions to ask after completing a project for a case study? (timestamp: 6m 0s)

Felt much more confident after using your 5-page proposal template with a new prospective client. I have a 14-day expiration on it. It’s been a week with no response. How would you handle the one week check-in on this? (timestamp: 18m 1s)

How to find out from your existing / past clients what was your ‘competitive alternative’. - ‘what would your clients do if they didn’t hire you”. I am wondering how to find that out from clients directly? How to frame that conversation and get the answer I am looking for (and not something like “we would’ve hired another consultant / company”) Is this something you would recommend being part fo the questions for Client Testimonial (vs. 5-question from The Brain Audit) (timestamp: 32m 27s)

Copy from the slack channel re PS - One direction that addressed my ‘product’ side: “We help growing tech startups with creating strategic products/features and grow customer base!” - that seems a bit unconvincing, and if we focus on the ‘pain’: “We help startups in growth stage with implementing strategic product / ideas that are getting delayed/postponed” (timestamp: 2m 2s)

What are your reccomendations on building an effective (cold) email outreach campaign for new strategy work? (timestamp: 23m 11s)

I’m trying to build out a sales page according to “The Perfect Sales Page template” article. It’s still a draft (I haven’t completed the actual offerings) and the “unique” section but would love feedback so far. (timestamp: 38m 48s)

You mentioned a podcast as a midrange authority builder. Do you think a weekly newsletter would be a comparable channel? Or is one preferable? Thanks. (timestamp: 53m 33s)

I’m fairly new with my business idea, being a Notion Consultant. And don’t know where to start. - Is it realistic to work on a LFPS now? The current one is and doesn’t give me a rollodex-spark: I’m a Notion consultant, helping digital product providers building their digital workspace and save admin time. Unlike my competitors I offer my services for the German speaking market. - If it’s too early for a LFPS; what makes more sense to focus on? (timestamp: 55m 54s)

Jonathan, I’m having trouble getting to the next phase. Not sure if it’s an execution thing or a focus thing. My vCISO advisory has been successful, but I want to take it to the next level for scaling. My Getting Into Infosec podcast has been VERY successful but needs continuous attention. I know everything that needs to be done, but having trouble prioritizing content creation, with delivery of work, and etc. (timestamp: 61m 26s)

If time for a second question. I’ve been following the LinkedIn making connections approach. Getting a lot more conversations going, even a couple of phone calls. Learning A LOT about the real estate agent industry (and mortgage brokers), but I’m struggling to see obvious opportunities where I can help them consistently, “Oh would this bring you value”. They essentially all just need more inbound leads. (timestamp: 67m 53s)

How do you deal with the “value dichotomy”? Meaning, the activities at the start of a project are much more valuable than the actual deliverables themselves, but you can’t price “discovery/strategy” nearly as high as the implementation work? (timestamp: 1m 50s)

I’m focusing on developing my positioning statement this month, would love your feedback on it, thanks so much Jonathan! “As a physical design advisor, I help technical product founders navigate the ins and outs of commercializing lasting products to build durable brands and businesses.” (timestamp: 15m 37s)

I just got an email from a client I haven’t worked with in about four years. Since then, our business has changed a lot. We charge $5k minimum for initial work, which is always a report. We charge much more for implementation if/when we do it at all. What’s the most tactful way to adjust a client’s expectations? Do you have a script for this? (timestamp: 30m 1s)

I’m considering a Slack-only, one-on-one design advisory program for physical product founders—to create a lower barrier of entry. Up to this point weekly live calls that include Slack access but they are a harder sell due to price point. I see this as a way to begin the conversation, then upsell to more live reviews and audits. Any words of caution or suggestions from your experience of running Slack-based coaching programs? (timestamp: 36m 2s)

What do you do to keep yourself consistently focused (over a period of years) on tasks that are mind-numbing to you, but ultimately very important for your business (for me: prospecting on LinkedIn & cold emailing). (timestamp: 42m 10s)

In your last mail you talk about change. How to support clients and help them not to be afraid of change and to encourage them to see the value and give a chance to the “scary” or “radical” solutions you might propose? For eg. in the COVID19 situation in many industries - for eg. the travel & hospitality or events industry a paradigm shift is required (at least until a vaccine is established). (timestamp: 46m 19s)

Also working on my positioning statement after watching the crash course and another one or two previous live streams. In A for B style: “I do spreadsheet automation for property managers” in “I help x with y” style: “I help property managers to improve client relationships” or “I help property managers to close more clients” (timestamp: 56m 55s)

As you prob. do you think the current COVID-19 pandemic will inhibit people from VBP? I get a feeling that decision-makers that are being blasted with demands for layoffs are hardly going to sign a $300K check right now. (timestamp: 1m 37s)

I have been working to move from design services to design advisory as a subscription or retainer, with the majority of this year being advisory. However new client may still come to me to do a task, which then I sell them on the task being a subset of an advisory package with a multi month commitment. Can you speak a bit about advisory retainer best practices and what’s worked and what to watch out for? Also, difference between advice or access as a subscription vs advisory retainer? (timestamp: 10m 13s)

Being a trusted source of advice for many of us in this group, what are your thoughts on running and managing a business during these turbulent times? What are you hearing from your clients? Have you given thought to how this changes value-pricing in the future and/or do you see a greater need for productized services vs. customized? (timestamp: 34m 47s)

What, if anything, would you do differently in regards to outreach in times like this? (timestamp: 47m 2s)

What specific parts of your system outlined in TPS you would focus on, over others, in times like this? (timestamp: 54m 15s)

How do you switch frames from the initial “why” conversation where you’re trying to “un-sell” yourself, to the practitioner who does see a problem? i.e. “I don’t think there’s a problem here, prove it to me” to “Okay, I know there is a problem, let’s fix it”. (timestamp: 1m 20s)

Let’s pretend you were still doing mobile consulting. Would you walk us through how you’d land a new VBP project, if you only had 2 months, and couldn’t use your current platform? (timestamp: 5m 20s)

As a software engineer working as a full time employee for a large company trying to put together a business case to be an independent solo-prenuer to convince a skeptical, risk-averse spouse, how large of a revenue stream could be anticipated and within what timeframe? This question is open to everyone. Direct message me or post in the general chat, whichever you feel most comfortable. (timestamp: 20m 52s)

Can you please review the pain, dream, and fix portions of our UX Sales Page that you mercilessly critiqued during the last session? You liked the rest of the documents, so this doesn’t need to be a full review. (timestamp: 26m 15s)

how do you deal with prospects that respond to “why” questions with long-winded responses..totally torpedoing/confusing the conversation? (timestamp: 46m 28s)

Can you take a quick look at my new site? Is the messaging clear? Is the niche too broad? Any major concerns that jump out at you? (timestamp: 2m 43s)

Can you review our sales page copy mercilessly provide feedback? (timestamp: 27m 47s)

Do you have any advice on how this LFPS could be improved: I’m a Product Designer who helps fitness software companies deliver personalised experiences in compliance with privacy regulations. Unlike my competitors, I use compliance to build trust instead of degrading the experience by overwhelming prospects and customers with legal content. (timestamp: 55m 24s)

What are some marketing/reputation-boosting things I could ask clients for in exchange for pro bono work? I’m trying to build connections in a relatively new niche, and I’ve found a prospect in that industry with no budget but a small enough project that I could deliver with little hassle. I was thinking of asking for a written testimonial, a video testimonial, and doing an in-depth before/after case study. Thoughts? (timestamp: 1m 25s)

How do you deal with situations in which exclusive economic buyers are very time-poor, and cant concede the time you need to have a proper why convo? (timestamp: 6m 59s)

Do you think roadmapping/discovery sessions are a good stop gap to sell more projects until you build up an authority? Roadmapping/discovery sessions are kind of a drawn out version of your why conversation and the proposal, but with the added benefit of being able to build more of a rapport. The why conversation seems to imply that you are already someone a potential client knows enough about to answer “why me?” relatively easily (an authority). (timestamp: 22m 25s)

We currently provide web consulting services to several public policy nonprofits (think tanks), but those clients have referred us to many other types of nonprofit groups. I fear that think tanks alone are too narrow a niche, but nonprofits seems much too broad. How would I go about determining if think tanks are a good niche? (timestamp: 40m 10s)

Could you recommend a “template” of questions the client should answer, to help them give you meaningful/useful testimonial? (timestamp: 51m 51s)

I’m quite pushy in getting prospects to get on the phone with me. It feels unethical to me because I know that I start all my projects with a fixed-fee discovery period (it’s the same for everyone), and I only want to get them on the phone so I can control how emotional objections are handled, (not because its the right thing for the prospect). Do you ever take on engagements without having a call first? (timestamp: 53m 31s)

How would you recommend to weave in paid roadmapping with your approach? Do you get them a price up-front, with the roadmap being the cheapest option? I find that roadmapping is often the most valuable part of the engagement. (timestamp: 57m 49s)

I have a sales interview tomorrow with a very qualified prospect (first point of contact), and I know that they have received a proposal for $175K for the project already from an established agency that specializes in the same niche as I (CRO for SAAS). How can I possibly compete with this agency on any metric other than price? I believe if I propose a price anywhere close to $175k, they’ll just think “ah well might as well go with the agency to hedge our bets, then”) (timestamp: 1m 15s)

Sticky predicament: in my sales interview tomorrow, the guy who referred me will also be present. He’s a freelance developer that has a strong relationship with the prospect. It seems strange to price out the entire solution (discovery->design->development) with the prospect, when I know the developer is stuck in the hourly trap. I get the impression that he will confuse the process since he will want to bill the same client hourly for the development. Any advice? (timestamp: 12m 50s)

In a previous coaching call, I asked you about “website as a productized service”, and you gave the example of someone you hired to build a “website in a day”. Here’s my pilot test project for $5,000 “website in a day“: Does this meet the bar you’d expect for the pricepoint? Do you have any suggestions before I go live with this offering? (timestamp: 19m 11s)

Using your Dentists audience as an example, when dealing with 1 person/smaller businesses, how would a software designer help this kind of audience vs helping software companies that build products for this audience?\ I don’t see why these kinds of businesses would pay for software solutions to be designed and built when solutions likely exist and if they don’t exist, surely wouldn’t pay the kinds of prices required. (timestamp: 32m 7s)

I’m having deeper why conversation and having people tell me their problems and things that will happen if they don’t fix it. It all sounds pretty serious, except when it comes to “is this a problem worth solving? or “how much is this problem worth solving?” - not getting a numerical answer, their answer is flipping it back on me. This has happened the last few meetings. Am I positioning/phrasing something incorrectly or is my market target still off? (timestamp: 1m 39s)

My why meetings are going further but when it comes to the money - it’s “too expensive.” At the same time these are all multi-million dollar biz owners who agree they have these problems. At the end they start talking about doing a commission/percentage scenario or I do this for them, and they’ll include my production services in all their marketing/welcome packages, basically everything except actual payment. Maybe it’s something but I would rather get paid. What are you thoughts on this? (timestamp: 18m 29s)

Does anyone know where CTO’s and Startup exec hangout online? Any resources are welcome. Thanks! (timestamp: 22m 38s)

I’ve had ~50 or so value conversations, though I’m finding that prospects get emotional and guarded when I start probing and asking about specific revenue numbers (if I don’t probe for the value in their own words, they often don’t have a realistic anchor, so my $xxx,xxx price seems insane). Common objections are “why is this relevant?” or “that’s for me to worry about”. How do you manage objections like these? (timestamp: 30m 7s)

Can you give me your thoughts on my sales funnel draft? This all stems from the Slack convo we had about low carb docs using Patreon. I pivoted just slightly from targeting “low carb docs” to targeting “low carb podcasters”, since “podcasters” seems to be a larger potential market. (timestamp: 44m 14s)

I get the impression that access to highly exclusive economic buyers boosts your likelyhood of closing 6 figure deals moreso than understanding the principles of effective VBP. So, someone who sucks at VBP is much more likely to land a windfall deal than someone who understands VBP but doesn’t have access to experienced buyers. Is positioning & access the real golden ticket? What are your thoughts on this? (timestamp: 61m 41s)

Working on launching my group coaching class... need to get people enticed so I’m thinking about a $99/mo lifetime discount for early signers. What do you think? Regular cost will be between $250-500/mo. Target is CTO’s and technical founders in growing startups. Also, I keep going back and forth between “class” and “community”. Thoughts? (timestamp: 67m 4s)

Last time, I asked you about developing & testing a point of view like “Hourly Billing is Nuts” - in this case it was “Referrals Don’t Work”. Can you give some practical examples of how to deploy this point of view, how to use it effectively in marketing? (timestamp: 71m 42s)

How do you have the why conversation with smaller businesses (less money available), if at all? Sounds like it’s more appropriate for larger businesses. (timestamp: 76m 17s)

I’ve been trying to figure out a Distinct Point of View, along the lines of your “Hourly Billing is Nuts”. My target market is independent management consultants, who see referrals as sacrosanct in lead generation. I’m considering “Referrals Are Not Enough” as a somewhat contrary PoV. Do you have any suggestions on this question? (timestamp: 1m 49s)

On the topic of contrarian catchphrases, if I want to specialize in accounting and business consulting for small law firms, how are these phrases: “Law school didn’t teach you how to run a law firm.” or “Law school didn’t prepare you to run a law firm.” (timestamp: 17m 43s)

What is your position on working with recruiters? Should they be considered a last resort for getting projects, or is there a way to work with them that supports your business long term? (timestamp: 24m 58s)

Getting more comfortable with brain dumps and asking why questions but having trouble going deeper with the ‘whys’ and demonstrating higher value. I’ll ask why me and always get - because john said you’re good, you have the most reviews, your work looks amazing. I’ll go into “i’m probably the most expensive option” and so far have continued to talk myself out of every sale telling people they can hire less experienced photographers for what they’re trying to do. (timestamp: 31m 59s)

How do you create that luxury perception for a service where it’s so good people just want it no matter what the cost is?

I remember in an earlier session you talked about being stuck in your income/class bracket and clients probably having same problems as you. What are some practical steps I could take to appeal to a higher income bracket? And maybe any recommendations for stuff I could watch/read to learn more about this mindset. (timestamp: 47m 9s)

Do you have any tips on getting testimonials from current clients? Would the approach be any different than at the end of a project, or different from approaching past clients for testimonials? (timestamp: 60m 42s)

I think one of the reasons I’m talking every person out of working with me is because I’m looking for a project but they’re looking for a productized service. If that’s the case, what are ways to immediately identify this, and how would you approach a productized service convo on the phone? (timestamp: 63m 10s)


After the brain dump and why conversation, how does it look/sound when you transition the conversation into talking about your price? (still getting the hang of this, i know it’s to qualify fit/answer objections). Do you present 3 pricing tiers on the spot? Do people get shook when they see the numbers? After presenting price would you ever change it? Seems at this stage I either have to walk away with a check or nothing. (will be our 3rd meeting, 5hrs later.) (timestamp: 1m 44s)

For the first time in my life I am having valuable/completely different convos with potential clients. In my mind even though i’ve specialized and am focusing on an outcome, i’m still getting hung up on pricing. In my digital/creative field I practically have no costs and am creating intangible assets. How do I get over this and just break through saying numbers like $50k? I know it’s all in my head but I’m coming from a place where the most I ever charged was $5k and still doing $500 gigs. (timestamp: 13m 30s)

My why convos/me asking questions about their biz have been turning into 2hr long unpaid discovery sessions. It’s been helping me understand where they’re coming from/where they want to be, but am I going off track here? Where do you draw the line when it comes to access to your head and letting people know they will need to hire you for a consultation? (timestamp: 29m 0s)

Met with someone who owns a successful investment management firm and wants to build authority on the web for their industry. They purchased a $3.5k youtube/sales funnel ecourse roadmap. They are too busy to do it themselves and want me to execute everything for them from the roadmap. I asked why me and they want one person they can trust that will get the job done. Pretty much I am building their money-making vehicle, but it’s not my roadmap. How would you approach/price a project like this? (timestamp: 36m 38s)

I’m working on creating an ideal customer avatar - aka buyer persona - aka a bunch of other terms. There are a ton of resources on this that suggest going into so much detail that you list what they had for breakfast. It’s too much. What is the 80/20 or MVP of an ideal customer avatar? (Note: next question is somewhat related) (timestamp: 49m 23s)

Can content marketing work for generalists? Is there a requirement to be a specialist to make content marketing work? This is related to the previous question :) (timestamp: 53m 54s)

I have a bunch of email addresses of prospective clients (not bought- found via a directory they are members of). Any ideas on how can I use these in a non-spammy way, e.g. create look-alike audience in FB, etc? (timestamp: 64m 2s)

Last session was my attempt at specializing to architectural real estate photog. You talked about writing daily. I’ve been having trouble coming up with valuable ideas to write about for my niche audience of realtors. So far what i’ve written only helps photographers. I did some pain point research but I don’t think my skill set would even solve those problems. Could you talk about your writing process & finding ways of applying your skillset to help a vertical? (timestamp: 1m 53s)

Finding more and more that real estate photog on its own is incredibly commoditized like $200 shoots for a $1mil house. There are a select few people doing $20k+ shoots for designers/developers, trying to get in front of that exclusive crowd without an intro has been tough. Should I bite the bullet and accept these smaller shoots as a way in the door? How would you go upon this? In the past, in order to charge more and make a living, I’d tack on extra production services, web design, etc. But that would defeat the whole purpose of specializing. (timestamp: 11m 50s)

I’m a vertically-specialized web designer, my market are small management consulting firms. I’m considering offering some kind of content marketing as an add-on service (interview them to create blog posts, podcasts or something like this). Any advice on offering this? (timestamp: 28m 56s)

Can you talk more about your writing process? (timestamp: 45m 44s)

Current client buckets: 1. companies looking to improve efficiency. 2. early stage startups. Project Categories: - streamlining payroll. - build custom work management tools(simplifying complex internal processes). - leveraging automation tools. Horizontal Positioning First Pass: We help companies improve efficiency by building work management tools. How can I improve positioning based on past project types? (timestamp: 1m 26s)

Good ways to open conversations with people and ask them to share pain points in business? (timestamp: 17m 21s)

Your 25yo again starting over from scratch with everything you know from today. All you have is your skill set + niche page + $500 ad budget. What are the top 3 things you need to be doing on the daily to create a prosperous business. (timestamp: 22m 19s)

My target market is consulting firms. For new business, they are very referral focused, it’s all about the network and word of mouth. “Sales” is often even a taboo word. Given all of this, what is your advice on selling marketing (strategy creation and implementation) and websites to this market? (timestamp: 32m 17s)

If there’s time could you do a site tear down: might remember me as the ‘digital solutions guy’ this is my attempt at niching down, feedback really appreciated, thank you! (timestamp: 49m 26s)

Will you help me identify what niche to pursue? Let’s play like I’ve never attempted to pick a niche before... (Since I’ve been trying to position myself for so long, unsuccessfully, maybe I should start again at the beginning?) (timestamp: 1m 15s)

I’ve identified a watering hole for each of the 2 niches I was targeting in the past: 1. Men’s Professional Doubles Players: Very active on Instagram, and 2. Docs Treating Patients using a Low Carb lifestyle: Very active on Twitter. Both groups post lots of opinions and observations. But I don’t see many questions or posts that seem to be soliciting help. For those types of situations, what’s a good strategy to use to start helping them? (timestamp: 14m 47s)

I’m new to the world of LFPS/value pricing. I finally finished making my lead magnet and niche sales page. My 3 offers are all high ticket done-for-you in person web/production services. Would offering something like this your first time scare people away? Or would it make more sense to initially invest the time into creating educational digital content that sold for a few dollars just to get some credibility/momentum for myself? (timestamp: 22m 19s)

How do you assess & move forward with conflicting data? This week I interviewed five people. I was getting a split response so I almost scrapped my entire offer idea but decided to move forward anyway, solely on the fact that I’ve made a few substantial sales with this offer in the past. Could that have been a streak of luck or do I need to really find a solution that everyone can agree on? Just would hate to dump my energy into something that was a waste of time. (timestamp: 38m 10s)

What do you think about NDA? Is it a huge red flag? (timestamp: 49m 53s)

How to deal with people prejudice because of my name? I think I get dismissed a lot because of it. (timestamp: 52m 53s)

Hi Jonathan, most of my income is 20% big projects, 80% smaller $200-$500 fixed scope gigs. This month I’ve talked every single person out of working with me and it felt like the right thing to do. Except now it’s really starting to add up and idk how much longer I can keep this up for. So how does someone in their early stages of transitioning to value pricing do this without hurting their income? (timestamp: 55m 21s)

Does pigeonholing apply also to companies? I run a software house with 10 people. We do web apps and also mobile apps. What would LFPS look like? (timestamp: 1m 35s)

I have upcoming large project. On the initial call, the client is trying to understand how expensive is my work. I said that I don’t bill hourly, only fixed price projects, etc (from your best practices). And then the client ask: ok, what if the project will need you as a part-time developer, how much will it be, or how much do you want for a one-month full-time project? What can I answer here? I told them my desired numbers, but I think it scared them as hell. (timestamp: 25m 48s)

How does one get someone like Seth Godin to appear on their podcast? :) More context: is this possible for a fairly new podcast with a small audience? (timestamp: 38m 1s)

Would you consider “entrepreneur” as too vague/broad as a targeted audience? I’ve been struggling with this question for months. We do our best and most valuable work (with varying deliverables that are specific to a measurable result) with people who have started their own businesses and are in a position to grow in a significant way. By targeting owners we get access to a decision-maker, passion, vision, etc. (timestamp: 46m 14s)

How did you start building your audience / email list? Much of the advice on the internet assumes you have a decent social following or web traffic. Was that required? Or, can you build it and they will come? (timestamp: 56m 16s)

About that “super clear mission” I’m trying to figure out my Mission or “Point of View”. I want to help experts to create a successful business around their expertise so they can compete with larger companies. Why? Because I found this incredibly difficult to do myself, and so I want to help people like me. Any tips about turning this into a simple super clear mission/POV like yours? (timestamp: 62m 55s)

Jonathan, can you talk a bit about websites? I.e. what you think are the most important elements to have on there, what’s not important, etc? (For context: coming from the perspective of a B2B service provider like a marketing consultant, etc.) (timestamp: 1m 33s)

Thoughts on niching down to a particular service, rather than a particular product? For instance, instead of “I make X,” it’s “I ONLY do the Y part of the process for creating X.” How do you convince customers that specialization like this has real value, even though you’re selling an incomplete version of the product they’re looking for? (timestamp: 18m 32s)

I’m interested in using surveys to research my audience, their needs, and to market myself as a thought leader. Do you have any suggestions related to using surveys to get the maximum return for effort & investment? (timestamp: 29m 37s)

Motivation, and working with smaller or larger clients? One of my driving motivations in business is “to help the little guys to even the playing field so they can compete with the bigger guys”. However, it’s the larger companies who have large budgets and they also get more value from my services due to scale. Do you have any advice on resolving this conflict between motivation and working with folks who have more ability to pay? (timestamp: 39m 4s)

How do you charge by value to people who ’know your rate’. A coder creates a website for a pizza parlour. The pizza parlour owner doesn’t know the market rate for that skill and they pay. Same coder goes to an engineering company that has a much better idea of how much a coder is ’worth’ in the market (rate-wise) and has a pretty good idea how long such a task would take. In other words, they’ve already calculated: our budget = hours * rate. The second is clearly a tougher sell, any tips? (timestamp: 1m 18s)

(From your TBOA episode “do you DO or do you KNOW”) I’m getting pretty good at the Why conversation, can always uncover a deeper pain than their self-diagnosis. Trouble is, even though they appreciate that, ultimately they still want someone to just “do” that work - they don’t want an advisor. Occasionally I’ll just do it, but how does one transition from one who does to one who knows? Doesn’t seem to matter if I’m talking to a decision-maker or not. Guessing it’s a marketing problem? (timestamp: 11m 6s)

So I did a job where I reckoned a task would take me half a day. Because of technical issues it took five days. Some of the issues were mine but most were hardware or wiring issues (the client did the wiring). Can I ask them to pay more and if so, how? (As an aside I could have saved myself the wiring problem by saying “I’ll do the wiring” as an Option 3. I will do that next time). (timestamp: 23m 29s)

I always thought “even the possibility to reach us and our knowledge is worth something”. I found your article “HOW MY RETAINERS WORK” and i think: we have the same opinion. 1) If a client doesn’t accept a retainer agreement. What is the consequence for his service?/How do you handle this request? > Do you write a proposal? > How fast do you make it? Don’t you even make it? 2) Just to get a feeling, i don’t want to be indiscreet - how much would you say is worth a retainer? (timestamp: 31m 30s)

  1. Question. As a second service we offer to host the website on our servers. Compared to a normal hosting service, we are expensive. But the client get’s a lot of extras from working with us. Comparing to the time, we are investing in support, it is not a very worthwhile branch. Do you have ideas how i can transform the “agency hosting service” to a package and a price, which is more worthwhile? (timestamp: 40m 23s)

Any thoughts on transitioning from a “DO” to “KNOW” role with an existing client, without leaving them in the lurch with tasks? Thoughts or advice for someone who “KNOWS,” but very much enjoys “DOING,” but is also up against a hard wall with capacity? (timestamp: 48m 2s)

Back to the “already know your rate” type of customers – an agency, for instance... Thoughts on asserting your expertise (even as a DOER) by tying your cost to a static (large) percentage of the agency’s profit, rather than your typical cost of work? (timestamp: 52m 35s)

How do I find topics to create content? How do I make sure my content isn’t useless? Someone’s advice was to spend 3x creation time on promoting. If I spend 1-2 hours on a video creation. Then I need to spend 3-6 hours promoting a piece of content? Do you agree with this 3x rule? What’s your take? Finally, what would a high level weekly plan for creation + promoting content look like? (preferably with recommended time per activity) (timestamp: 1m 22s)

I’m starting to work with a lead that looks almost certainly looks to become a whale client (high revenue, high % of working hours). I do have protected space in my calendar for working on my business, and I am not letting the extra revenue bloat my budget. Is there anything else I should be considering, either to maximize the benefit of a whale client, or maybe not even take them on. (timestamp: 12m 9s)

Coaching: should I offer a free initial call? How should I structure my offering? [Question was too long for Crowdcast - see it on Slack] (timestamp: 20m 10s)

Building on a recent TBoA episode, lay out a comprehensive plan that takes someone from expert to authority. (timestamp: 34m 30s)

Is the largest part of your audience growth through content/broadcasting and I shouldn’t be overly concerned about “growing the list”? (timestamp: 57m 45s)

Most of my work is coaching (on-site and remote) with some training. Great balance now of work, content creation, and pipeline. Add 2-3 more clients and I will be out of balance. What do I say to people I’ve been courting who say yes, but then I’m too busy? How do you manage the pipeline when you are near max capacity? (timestamp: 1m 29s)

I’m setting up a 7 email course and then moving them onto a list where I email 3-5 times per week. I like to go 80/20 on this. Can you tell me a bit more about the mechanics of your email list setup? After you deliver your 6 lessons, do you then move them off that sequence and onto your daily email list automatically, or do you offer a new opt-in? If they’re in the Bootcamp Lessons sequence, do you isolate them so they don’t get your daily emails? Any other tips? (timestamp: 7m 10s)

My weekly email list (content delivery similar to your daily email) is opt-in. How do I grow it? (timestamp: 19m 16s)

I’m interested in knowing how to publish a book? You once asked about it on your newsletter and at that time I didn’t even consider it. I’d like something similar to your social networking process sheet (an overview of how to make it happen) (timestamp: 28m 2s)

Survey/Original Research: have you ever surveyed your prospective clients to conduct original research, to establish yourself as a thought leader, etc? Any thoughts on this? (timestamp: 48m 31s)

Hey Jonathan, I’m having trouble doing outreach to specific companies that I’ve identified as leads but that I don’t have any relationship with. It’s hard to find emails for these companies - sometimes their contact form or email gets a response, but it feels like shouting into the void. How would you reach out to a specific company you’d like to work with? (timestamp: 1m 5s)

What advice do you have for me in getting onto popular podcasts in my target niche as a guest? I have seen some horribly written form emails sent by some “podcast guest placement services”, and I want to make sure that I distinguish myself from these. (timestamp: 14m 38s)

I’m looking for your advice on growing my email list from scratch. Some channels or strategies I’m looking at : - Hosting my own podcast - Guesting on other podcasts - Free 7 day email course - Having an automated webinar (possibly driving traffic from by Facebook ads) Do you have any suggestions on growing my email list using these or other methods? (timestamp: 21m 50s)

“We need you guarantee a date on which you and your team will deliver a perfect bug-free issue-free product.” How do you manage the delicate balance between agile development and the reality that accounts need to know an exact date when you will deliver because they are planning PR, building a marketing launch around Product Hunt, trade shows, internal timelines, fund raising, investor commitments, etc. around your delivery date? I’m dealing with an account that has a whole product launch machine behind the product we are building, we’ve slipped delivery date by 3 weeks for a number of reasons, including scope creep. How do I deal with setting delivery date expectations up front? (timestamp: 33m 54s)

One big question that’s been nagging recently is how do you know how much cushion is enough without specking out deliverables? Have you ever had a scenario where you gave a value based price and then got into the project and realized you far underestimated the effort it would take to get them the desired results? (timestamp: 48m 18s)

Another question if we have time... In the scenario where multiple people are bidding on something. Do hourly billed agencies typically have lower “quotes” than yours? Does your positioning as delivering value typically win over the client from the hourly billing agency? (timestamp: 57m 43s)

My primary area of expertise is branding, but it’s challenging to hone in on pains since “branding” can include many touch-points that connect a customer to a business. The most narrow I’ve gotten is “I help small businesses attract and retain new customers.” which still feels general, but allows me to provide solutions in all areas (print, product, digital, etc.). What are your thoughts on how “branding” is defined and the associated pain points? (timestamp: 1m 30s)

My local market has lots of high revenue small businesses which are good opportunities but they are very hard to get in front of. There are not many local industry specific conferences/publications etc. Do you have any suggestions for directly targeting local industry in this type of situation? Is it a mistake to focus on local. If so, do you have suggestions for taking first the first steps in getting remote clients? For context, I do full stack custom rails development of backend systems (timestamp: 22m 25s)

Promoting a brand new podcast: I’m launching a podcast called “Marketing for Consultants” in the next month or so. The audience is independent consultants who need help marketing their niche consulting business. Do you have any recommendations on how to launch the podcast to maximize impact/listeners in my target audience? I have no problem investing money if I’m spending it properly. Jonathan, I know you’re a big fan of 80:20, particularly when it comes to your podcasts: what’s the 80:20 here? (timestamp: 36m 31s)

Can you talk about the productized coaching ladder, and also the nitty gritty about how you manage clients and appointments. It seems like having the differentiated services and lots of people you coach, the logistics get challenging. (timestamp: 50m 40s)

Productized service on its own domain name/website: I’ve got a great domain for my productized service - a “does what it says on the tin” domain. Any thoughts on having the service on a standalone site, away from the primary business brand website? (timestamp: 57m 41s)

Can you explain a bit about value-pricing for Research and Development? Thank you. (timestamp: 61m 15s)

Meeting with some company leaders to have the why conversation. When we get to the “why me” part, how do I do that? I have strong credentials, but they are all from P-12 and higher education. Do I just trust that my ability to help them identify a problem that they aren’t actually fully aware of, and to offer some possibilities based on their unique situation, that will give them the answer to “why me”? I am not into selling myself, but they have a real need and I know I can help them. (timestamp: 1m 16s)

How do i keep track of linking to my own content between blog posts, email news letters, website, etc? (timestamp: 11m 2s)

We build large scale projects that typically last 6-8 months. I’m relatively new to services business and our ability to estimate delivery dates sucks and we seem to always be off. Right now 3 weeks late for delivering on a project. Death by 1,000 papercuts along the way seems to be the recurring problem. (1) How do I better estimate delivery dates? (2) How do I set expectations with these clients up front and part of the sales process? (3) Our practice is to demo weekly, but client gets frustrated that what we show is not yet perfect. They say “Why are you taking our time to show us stuff that doesn’t work perfectly yet?”. How do I deal with that when it’s a best practice? Damn, I think I need to get back to building products! Help! (timestamp: 20m 46s)

When things slow down on my end I tend to reach out to agencies for work? They always ask for the hourly rate! Is it possible to sell value pricing to an agency or is it a lost cause? (timestamp: 50m 1s)

I want to productize a service and offer a course (or series of courses) with three options (no touch, low touch, high touch). I already have a buyer. I know how to write curriculum and teach, but how will I manage it? What do I need to think about? What technologies should I use? (timestamp: 1m 37s)

Project/client management - how do I keep track of everything? Following up on scheduling, check-ins between phases, updating materials, making sure my clients feel special... Ugh! How does a non-programmer automate workflows? (timestamp: 20m 7s→)

I’m looking at offering “Website as a productized service” for consultants. I’m trying to figure out how to price and scope this offering - I was looking at starting out with a single $9,000 offer. Can you give me feedback on pricing & defining the scope of the website/engagement so that it’s profitable and high-value for my clients? Any other tips on doing this as a productized service greatly appreciated. (timestamp: 25m 12s)

I have a fixed price project (100% upfront). It should be finished in 2-3 months (plus 3 months guarantee). But when the project is close to finishing, the client is gone (priorities are temporarily changed in the business) so the work is stopped. And now, after 7 months, the client returns back and want to finish the project. It breaks the schedule and I am not sure I want to continue with the old price. Is there a good way to resolve the situation better? How to prevent it in the future? (timestamp: 32m 55s)

Currently looking into think tanks as a niche. They provide financials as a non profit. Is this an area I should look into? Not really sure how to look over a financial doc (timestamp: 39m 30s)

Understanding that the goal is value pricing, but I have a large potential client that wants a blended hourly rate. How are others calculating this blended rate? What are others in this group charging per hour in the US market when an hourly rate quote is required? We build large multi-month SaaS application engagements that typically include multiple interfaces including a company facing admin, customer facing web interface plus native iOS and Android customer facing apps. (timestamp: 53m 13s)

My current position: I help physicians educate their patients about Low Carb without using valuable clinic time to do it. Should I narrow down to a specific type of physician? Can you give me a quick refresher on a plan to engage my target via Twitter? When I update my Twitter bio to reflect the new position, should I also update my website? My LinkedIn profile? (timestamp: 39m 50s)

We currently offer our clients website support plans. (Which are basically retainer access to us, with some value-added services.) In the context of that type of offering, What are your thoughts on billing monthly (without a contract) vs. billing monthly (with an annual contract) vs. billing up-front for the entire annual contract? (timestamp: 1m 35s)

Hi Jon, can you design a productized coaching service over a period of time and set availability hours? Or will that make the client divide the amount per the hours set and defy the whole purpose? (timestamp: 20m 5s)

Following the website support plans question... One specific scenario from our company. We finished a website. And 2-4 weeks after launch, the client starts doing things like Online-Marketing. Some of those random calls or emails come in: - We have now a linkedin page. Can you add the link to the footer? - Can you please implement a facebook conversion pixel on the website? - How can i change the image on my homepage? - More random questions... So it’s support, but no bugfixes. How should we deal with that? (timestamp: 32m 17s)

We work with entrepreneurs and start-ups but there is often little budget for brand development when a business is launching. We know name / identity / positioning / brand artifacts are critical to long-term success but there doesn’t seem to be a realistic budget for these services. Any suggestions on how to structure a conversation for finding a mutually- beneficial solution? How do you feel about equity as a consideration? (timestamp: 39m 57s)

Most of my business had been client work and I am now venturing out into products/passive income this year. What do you feel has been the best way to get started with creating passive income in your business? Courses? Trainings? Funnels? (timestamp: 1m 33s)

What are some of the benefits to using your own name vs a studio name? I work with other people on my custom projects so it feels disingenuous to have my actual name be my company’s name, but it’s way more recognizable than starting a new “studio” name. (timestamp: 22m 2s)

I know you’ve talked about conferences a bit before, but I seem to recall it being primarily about being a speaker. If I’m attending a conference that is primarily peers speaking (though they in theory could influence later hiring type decisions), what things should I make sure I do? What things should I make sure I don’t do? (timestamp: 31m 2s)

What are you thoughts on medium/high-touch services paid on a subscription model? - Context: we do custom websites as project-based fees, and are exploring moving to a value-priced subscription model. (Along the lines of a IT firm doing fully managed services.) (timestamp: 45m 7s)

I’m considering moving from contracting/consulting to enterprise training. My company has been working with the tech that companies are now starting to move to (in my geographical area) - React, Redux, Typescript. I think this will be higher leverage work than before. Plus I think it’s got a good value prop despite making me a (hopefully) a lot of money. What strategies do you recommend to make that move? What issues do you see happening? Do I need to start with other products? (timestamp: 58m 24s)

I have an agency who wants me to consult on ecommerce/shopify projects. But right now exactly how many projects they would isn’t defined. Should I charge a flat rate per project to consult? Or a monthly fee because I am available? I am also a little unsure how what price makes sense. (timestamp: 1m 19s)

I currently do custom rails apps, using agile, so minimal upfront planning/documentation. Looking at moving to more head than hands work, what would the deliverables look like for non-implementation project, ie what do you think would be in the table of contents for the roadmapping/discovery report? (timestamp: 14m 39s)

How can I use podcasting to reach my target market? (timestamp: 31m 50s)

Should I present my productized services in a build-your-own way, sort of like Chipotle? (timestamp: 43m 22s)

I need to renegotiate a referral agreement. An agency owner I know gets leads through his website that he can’t service, so he sends them to me. If I close a deal, he gets a kickback of 25% for 3 months which is just too high. Initially he was more involved in the sales process, but now he sends everyone the same copy-paste email intro and leaves me to sell. I much prefer being left to sell and am happy paying for the lead, but the $ needs to drop. Any advice? Have closed 8 of 22 leads so far. Extra info - most projects have an initial discovery component which is less $ than the project itself, and can often be 3 or more months between discovery and project, so I’m usually only paying a referral on the discovery component anyway. I’d be happy to create an arrangement that is a % of the discovery only, and remove the 3 month timeframe, but open to better ideas if you have them! (timestamp: 1m 56s)

After you have a value conversation with the client, do you like to talk about pricing/budget on phone with them so you can answer their objections? Or do you prefer sending pricing via email? (timestamp: 13m 54s)

Recently I have become much better at ascertaining the value of the project to clients, but their budgets are consistently disproportionate to the results they want to achieve. For example, the client wanted to increase their sales by 500k with a new website, but only budgeted 8k for the project. (timestamp: 22m 14s)

I had a client who wanted to increase their conversion rates by $45,000 a month ( we were going to redesign a sales page ), and I quoted a value based price and the client didn’t take it well and told me there were other designers who would only charge 3-5k for this same thing and that it was basically highway robbery. I have been feeling like I will always be anchored to industry rates even though I have really great value based conversations. (timestamp: 48m 38s)

Another thing the client said was “I’m not there yet so there is no way I would pay this.” It seems like clients base their budgets on their current sales, not the future goals they want to achieve. (timestamp: 66m 8s)

How do I deal with small requests like fixing minor CSS bugs? (timestamp: 1m 9s)

Just started publishing daily. When I have that habit steady enough, what do you recommend doing next? Thinking about focusing on making a free email course, productizing some services, or revamping generalist website to be more along my target specialization. (timestamp: 25m 26s)

I’m getting crushed by scope creep on a huge project. It’s for a starup where i’m building MVP for cash + equity. They’ve closed a seed round and have a fixed budget. Now we’re five months into the project and we’re discovering many new features/functionality that we’ve learned to better meet product market fit. All of these make perfect sense to me and should absolutely be built. But, it’s going to cost them another $150k beyond the $125k they’ve already committed to. They have $90k to spend, no more. (timestamp: 36m 34s)

Really having trouble with the advisory retainer concept. I know I’m not “selling an outcome” with this model but its hard to not want to just dive in. Realizing I’m very weak on communicating what they should do vs me just doing it. Do you have any suggestions here? (timestamp: 55m 12s)


What do you do when you can’t get a decent understanding of what a prospect’s “ideal outcome” on a first call with them? I just had a weird initial consult with a very large non-profit who showed up with 12 people on the call (only expecting one), and I simply couldn’t get simple answers from them as everyone kept jumping in with their thoughts and confused things. Got out of hand real fast. (timestamp: 1m 20s)

I am a filmmaker who works fast and feel that many of the times I lose money due to being fast at my craft. When asking the client the why questions and they do not give you an amount that they hope to make off of the video you produce, how can you create a quote if you do not base it on your old hour rates? (timestamp: 9m 28s)

What if I ask a client how much they are willing to invest, but say they only want to invest $5,000? Is that what you charge or do you create a proposal with three different prices with $5000 being the top tier? (timestamp: 31m 24s)

Is it better to position yourself as a video consultant rather than a retention consultant? Does it matter? (timestamp: 41m 15s)

I’ve heard you rave recently about your VA on podcasts and am trying to think about what I could use one for. Can you brain dump some of the stuff you have yours do? Context: rails software developer doing/ paid discovery + currently lots of implementation (timestamp: 51m 49s)

You’ve talked a bit in the past about some of your strategy around conferences, but how do you decide whether or not to speak at one if given the opportunity? (timestamp: 1m 10s)

I provided an ideal target options on how I could help with an expensive problem (big traffic drop, poor conversions). Instead they asked for just consulting, to which I initially said yes. But it’s become clear any worthwhile solution requires a fair amount of hands on analysis and roadmapping. I could just fall back to a day rate, break it down into smaller productized service options, or walk away. What would you do? (timestamp: 19m 26s)

For advisory retainers, doesn’t it just boil down to hours? (example, an hour call a week plus email access with x turnaround time on responses) (timestamp: 37m 52s)

I’m trying to get myself onto stages and in front of people to help build my reputation/authority but haven’t done much in the way of speeches since school. Do you have any resources you would recommend for helping with both talk creation and presentation? (timestamp: 1m 18s)

I’ve made the decision to stop taking on new implementation projects so I can focus on building out a niche and my own products. Some of the clients will easily transition to working with my friend, but he only takes on high-value projects. As for the rest, I want to see them succeed and I don’t want to burn any bridges, but I just can’t continue to do hands-on dev work for them. Any recommendations on how to gracefully end the dev relationship with the remaining clients? (timestamp: 21m 13s)

Ideally I’d be prospecting to those making $1m+/year BUT feel like I’m maybe not “good enough” or experienced enough to be an attractive option. Any suggestions? (timestamp: 32m 29s)

I have a potential client who I proposed a ’Preliminary Strategy” session online prior to the Brand Strategy because she’s creating a new lifestyle category and has tons of ideas. I wanted to narrow down her ideas on a phone call or webinar to pinpoint her desired state, so going into the strategy session, we would have a clear direction. I’ll also be collaborating with a financial strategist during this session (timestamp: 51m 32s)

Is there ever such thing as additional scope on a value-based project? If the client pivots their whole business model mid-project which requires significant changes/revisions, do you just keep working under the original price? (timestamp: 1m 53s)

I’m working on a product ladder and debating how to price the various rungs. Is there a strategy or is it pretty subjective? Trial and error or is there some research I can do to dial it in? (timestamp: 19m 17s)

I’m hearing the advice of setting up a product ladder but am struggling with coming up with options. My Mercedes offer is typically a custom backend system ($30-$100k), and I offer an audit/strategy report ($5-$10k). My “sawdust” would be frameworks etc which I dont see my clients wanting. Am I thinking inside the box too much on this? Do you have general suggestions on products categories to kickoff brainstorming? (timestamp: 36m 20s)

When do you know to go all in on specializing? Does it ever make sense to just have two businesses? (timestamp: 47m 34s)

Follow up to my first question if you have time: if you work down from the top of the product ladder, how do you effectively generate leads for that next rung down? (timestamp: 55m 6s)

I have been developing a software application for a company for the last 18 months. When I took over the project was dead. Now it has gone nuclear, getting traction in the org. This is a big win for me and the team I’m working with. They want to expand it to other depts and are asking me to lead the effort (more assumed that I will), their desire is to hire me, my desire is to go from hourly to value, ugh, I feel like I might have to move on (timestamp: 60m 26s)

Is it ever okay to work on an hourly basis? (timestamp: 1m 49s)

I sent a cold email to a potential client, in the email I listed the things I can help with, here is the response I got “I’m not sure how to use your service. I would love if you could tell me something you could do for us, like a project/optimization you see us needing? If that’s possible. “ it seems that they need me to look into their business for free, what’s the proper way to get back to them? (timestamp: 14m 46s)

If I only have one url to direct people to, lke a “work with me” type page, what should I make sure is on it? Only the fixed price things? Only custom engagement process? Both? (timestamp: 25m 36s)

When does it makes sense to look for a business partner? Or is it better to keep going solo? (timestamp: 41m 53s)

When offering a bug-free guarantee, how do you handle or explain bugs that come from vendors/OS/browsers and not from our code? (timestamp: 1m 51s)

Do you have any advice on metrics to look for with a start up for evaluating value? Is there anything unique about a startup that would cause you to change your approach to pricing/proposal/etc? (timestamp: 17m 20s)

Does using different language like “promise” instead of “guarantee” make it less effective in your opinion? To us in Canada the word “guarantee” sounds a little Walmart. It seems to us that a guarantee is somewhat implied in the value pricing... (timestamp: 27m 38s)

Do you have any advice on what to do if your conference talk proposals get rejected fairly often? I’m not really sure what to do next, other than perhaps write a different talk to pitch next time, since there’s not much feedback. I live in area with very few meetups and such where I can trial/tune the talks much. (timestamp: 40m 35s)

if there’s time left, can you tear down my landing page? (timestamp: 61m 43s)

I am about to complete an hourly based project. It, shockingly, went about 15% over the estimate. The client is happy with the results, but not that the cost was higher than estimated. I’m writing a case study for the project and was wondering if you have any recommendations on presenting a case study where everything isnt a win? (timestamp: 1m 9s)

I’m getting ready to launch a new productized service, any general advice on how to price it? I’ve primarily done the work in the past as an FTE, so I’m a bit uncertain on pricing. (timestamp: 15m 20s)

I’ve built a team around me where we can execute on 3-4 big projects at a time. These projects typically last 3-6 months as they are fairly big. My issue is that I’m still very much in the center of it all. I don’t have revenues to support the hiring of talent to replace me yet. How do I bridge growth? (timestamp: 34m 24s)

Via email: I asked my client how would you measure the success of this project (after the work has been done), and they replied with the fact that they were happy with the “outcome”. Meaning the work was done, but couldn’t measure success in a dollar value. The work I provided was Brand Identity. In speaking with the founder and their staff, they all felt excited with the new look and feel of the brand. What am I missing here? (timestamp: 1m 12s)

Via email: Could a corollary to “If you’re worried about bugs, you’re not charging enough” be “If you are on thin margins you should invest more in quality assurance so there will be less bugs”? The issue here is pricing of QA services. Rich clients don’t fear bugs so don’t need QA, and poor clients fear bugs but can’t afford QA. Bummer... So how do you value price QA or other risk-control services? (timestamp: 14m 9s)

Via email: I am a 20 year old designer that is currently studying design at university. I have had paying clients but nothing over £2000 yet. My question is, how do I show the value I bring to them without having the “professional” experience? (timestamp: 46m 10s)

When a prospect asks, “how do you price your services?” I “try” to do 10% of estimated annual hard dollar ROI outcome as long as its head and shoulders above time and materials cost now. I’ve tried to “mix in” perceived value for unmeasurable stuff as part of that value calculation based on gut, but can’t tell a prospect that. So how would you handle that question? (timestamp: 23m 52s)

Can you do a teardown of my site (timestamp: 51m 42s)

I’m building an audience with my side hustle, with the long term goal of turning that into my core business. I don’t have a clear idea of what products I can create and sell to that audience yet, I’m just focused on delivering value for now. Do you think not having a plan about a product ladder during these early stages is ok? (my feeling is that the products will reveal themselves as I have more conversations with my audience). Or does that sound naive? (timestamp: 1m 32s)

When you write daily emails, come up with products or podcasts episodes etc., do you have one person in mind who you “speak to”? i.e. a person who is your ideal target audience? Or are you more generic i.e. speaking to an imaginary person who ticks certain boxes? (timestamp: 7m 51s)

I’m interested in potentially getting royalties from my clients’ skincare or cosmetic products. My clients are in the beauty industry, and I’m curious about the pros and cons for both parties, and how and when I would approach the convo. I want a passive income and if I’m invested that would show that I’m committed for the long haul, right? But I also don’t want to screw myself over or give off a money-hungry, selfish vibe. A previous lead wanted a similar arrangement with me, shark-tank style, but it turned out that they just didn’t have any money 🤦🏼‍♀️ so we never ended up working together anyway. Thoughts? (timestamp: 17m 0s)

Can you please teardown my website: (timestamp: 24m 12s)

How do you deal with the fear that comes from various marketing and sales activities (e.g., niching down, public speaking, launching something new, presenting premium prices)? (timestamp: 1m 33s)

What are your thoughts for offering referral commission for other consultants/agencies referring leads? (timestamp: 28m 33s)

When you value price a project to a specific problem/solution and find out problem is more extensive than you thought, how do you handle seeking scope change vs saying, “Okay I can eat into this profit, learn, and move on” ? (timestamp: 30m 27s)

Any advice on how to qualify leads? I had a lead recently, he seemed that he had a budget for the work though after exchanging emails I found out that he is looking for cheap service, I’d like to avoid such leads in the future, is it possible? If so, how? (timestamp: 35m 48s)

Any advice to stay motivated, positive, and focused? (timestamp: 40m 3s)

I can’t stay on the call, and feel free to answer anything else first but otherwise you can rip into my newly separated niched sites. FoxPro specific and Rails specific (timestamp: 48m 23s)

When building a proposal, I find it hard to figure out what should go in each option. I always ensure Option 1 solves their core problem, but struggle with where the “home run” should land. I’ve been treating option 3 as the “home run”, but that starts to feel a bit like options 1 and 2 are the dodgy non-options. (timestamp: 1m 24s)

I became self-employed about 2 years ago. Since then work has been a “Roller Coaster“! Some months projects are coming-in and life is good. Other months it’s completely dry. Based on your experience how can I have sustainable business? (timestamp: 9m 1s)

Is it important to to figure out “why am I doing this?” being self-employed I guess. I heard recently that I need to find my “why?”. When I think of my “why” it always comes down to this: pay the bills, provide for family, live a comfortable life – one day hopefully – and never work for anybody else ever again, am I getting this “why” thing wrong? (timestamp: 18m 6s)

I’ve got a 30 minute call with my ideal customer next week (CEO of funded startup). My idea : “I help startups with Devops”. This is a ‘I want to find out what your problems’ kind of call. I’m worried the conversation will dry up. What are some good questions to keep him talking? (timestamp: 26m 0s)

The question I plan to ask my target demographic for our conversation is “When it comes to growing your business, what is the single biggest challenge, frustration, or problem that you’ve been struggling with?” In your experience, would a question like this sounds an alarm in a business owner’s mind? In other word, how should I rephrase this question to make it more tactful? (timestamp: 31m 8s)

I’m just starting out, and don’t have any business connections, how can I present myself to my target demo as credible and not trying to sell them anything, in order to get them on the phone for a conversation? I’m working a full time job, so all my social media accounts are all about my work experience as an interpreter, so there would be a disconnect between what I’m doing now and what I want to be, which is a marketing consultant. (timestamp: 40m 11s)

If I need to put in some work prior to reaching out, what are the things I should put together to show them that I’m credible, and not just a random spam in their email accounts? (timestamp: 43m 30s)

Client wants to start project tomorrow that was set to start on the 9th. How would you respond to this? The reason for urgency is a bug they want fixed right away. The project is a 2-month optimization project to get their web app stable for projected growth in January. I had not anticiapted having to fix urgent bugs from day 0. How would you manage expectations here? (timestamp: 45m 27s)

just bc you have a few minutes - you said don’t work on portfolio/case studies? (we’re updating that stuff now) why not? can you elaborate? (timestamp: 56m 55s)

At the moment I’m an eCommerce development consultant. I’d like to transition into an eCommerce growth consultant so besides development work I’d like to offer services that covers digital marketing & conversion rate optimizations. I can do it though as of now I don’t have track record of it. Is it possible? If, so are we talking months or years? What would be the best way to approach this? (timestamp: 1m 28s)

I’ve a prospect (B&M) that needs help with digital marketing and Shopify store management. At the moment the store is doing pretty bad 0% conversion and traffic is pretty low, on the other had they are making $250K-$1M/year. I need help pricing this? (timestamp: 21m 11s)

I started off as a consultant with fixed pricing (sort of value), and have been pushed to go back towards a hourly rate as the client is trying to do some of the work themselves and are looking more for short interventions and are hesitant when I try to point out what the outcome is and how I can help (when they believe they’ve done 70% of the work). How do you suggest I handle these conversations? (timestamp: 28m 49s)

I started working with a well funded but frantic startup with a real deadline (conference) and need last minute help. I don’t want to gouge them or encourage the frantic behavior because they will be interesting/profitable future projects, but had no idea how to price small but not trivial work. How would you go about it? (timestamp: 40m 10s)

Do you believe that the path to thought leadership must always pass through the phase of expertise first? (timestamp: 2m 1s)

How much time I should be spending on growing my business per week or month? I find myself always prioritizing client work which I think on the long-term is hurting my growth rate. I’m not sure how to balance! Please advice, thanks. (timestamp: 6m 17s)

What do you think of paying for Ads to generate leads? From your own experience what generated most leads for you this year? (timestamp: 11m 57s)

What do you think about this LFPS? “I am a DevOps expert, who helps startup CEOs achieve their business goals by shipping better code faster. Unlike my competitors, I understand the needs of both business and tech.” (timestamp: 20m 4s)

I’m doing a Keynote at the local Devops Days next month “DevOps: Why the Startup CEO should care and how to convince them with numbers”. What would be a good lead magnet to have ready? (again, this jumped in my lap before I’ve done the prep for it..) (timestamp: 27m 52s)

When you’re new to pitching fixed-price expensive-problem: what makes sense as an initial project/product to a prospect who has approached you? I plan to have a product ladder ranging from the low-price-low-touch book/course, up to the very expensive done-for-you service. This prospect has approached me before I’ve thought it all through. (timestamp: 35m 3s)


In a recent proposal, I mentioned time to deliver since I know there is urgency to the project. But they used it against me: If it only takes X days, why does it cost $XXX? Did I make a mistake mentioning time? How can you communicate the added value of a quick turnaround without it backfiring? (timestamp: 1m 28s)

I’ve started a productised service creating digital annual reports, and aiming to sell to the renewable energy sector (basically, annual reports published as microsites, I have sold two in other verticals). I know a bit about the R.E. vertical, can speak about benefits over features etc, but can def learn more. Would like to get a landing page up - any thoughts on what this first landing page should aim to achieve at the start? Eg: lead capture, sales, something else? Happy to play the long game (timestamp: 8m 24s)

I get all my clients through referrals, which is good but I feel like a hostage. At any time those referrals could dry up and there is nothing I can do. I started putting effort into my website and social media. I paid a copywriter for website content and blog articles so it reads professional. I also did few Facebook (and Instagram) Ads to promote my blog articles, Facebook page, and website. I spent around $400-500 and I got 0 leads out of those campaigns. How can I create my own sales funnel? (timestamp: 20m 19s)

I am having trouble connecting the dots between my skills and solving expensive problems. I have recently started instigating conversations with a market segment that I want to serve, in order to understand their problems. I am trying to be genuinely curious. But when they mention problems unrelated to my area of expertise, the conversation languishes. I already have clients who are getting value from what I deliver, so I know there’s appetite. Is this just a case of persevering? (timestamp: 34m 33s)

Can you give a good example of what a weekly habit of “optimizing for conversations” might look like? I’m particularly interested in using LinkedIn like you described on the BOA episode. (timestamp: 1m 6s)

As a solo consultant with a steady stream of referrals, I’ve always neglected building a site. Next month I’m bringing on a friend to join me, so I’m thinking more about the sales funnel and attracting leads. I hope this isn’t too broad, but what good resources can you point me at for building a site focused on attracting leads? Or is this the wrong thing to focus on for lead generation? (timestamp: 31m 22s)

Had a good why conversation, all boxes checked, sent them a proposal (told them I was the expensive option ahead of time), response “price point for this is higher than I anticipated”, “At a price point of $90k, I would expect more of a fully developed system”, my take, they are thinking cost+ pricing, not the value they are getting. Any suggestions on where to go? I don’t want to push, am fine with moving on (timestamp: 47m 36s)

I was referred by a client in the coworking industry (my niche) to their industry association. Apparently the association needs help with their marketing but don’t really have a budget. They want to grow the number of members and have several hundred already who pay a small annual fee. They also have a conference. I think the idea might be to get exposure to their network of coworking space owner/operators. I usually don’t work for exposure, but this feels different. Thoughts on this situation? (timestamp: 1m 32s)

If I’m just getting started with a new consulting business, and I’ve thought of a problem I think is worth solving, what should I be doing as a next step? (timestamp: 19m 12s)

What should I do if a prospect balks at my pricing? (timestamp: 35m 13s)

I’m feeling a bit stuck. As a contract developer, I’m essentially a fulltime employee. That means all my work time is committed to that employer, leaving very little time to work “on” my new business. have any ideas or thoughts on a good transition plan for someone like me, to be able to free up some time to get the flywheel moving? How have other students been able to do this? (timestamp: 1m 36s)

Can you tear down my landing page at (BTW, I don’t have the registration button wired up yet.) (timestamp: 10m 29s)

I have an awesome client, currently an hourly arrangement. A few months ago they had a super busy month coming up, and I suggested a higher-priced, fixed cost retainer which they accepted for that month. It worked great, and they went back to hourly after that thinking it would quiet down again, but it hasn’t really. I’d like to bring the retainer up again, and I think they’d be open to discussing, but they are quite price sensitive so not sure how to bring it up. Extra background: I started out doing creative work for them (brand design, brochures, signage etc) but am now more of a brand manager for them. I’ve become their first stop for advice on how to start/run/do most marketing projects, and am now about 50% project management and 50% creative work. I’ve created systems and dashboards for them to manage our work together and they’re always open about how happy they are, so each passing month gets smoother (ie, I’m making their lives a lot easier). (timestamp: 32m 27s)

Can you do a teardown of my homepage targeted at messaging / websites for professional service firms? I’m trying to balance how much to pigeon-hole my homepage. I’m considering niching it down to target only B2B CPA firms. I’m planning to run linked in messaging campaigns for specific consulting offerings geared just towards CPAs. Right now those are their own Landing pages , not my homepage. (timestamp: 46m 31s)

I help prof. service firms w/ customer experience/messaging strategy. Most of my clients don’t have a dedicated marketing function so we’re starting from scratch. I’ve found that clients want access to me to guide their strategy and activities, but quickly ask me to oversee or source a team that is also producing deliverables. Do you have tips on how to delineate and set boundaries between ’advisory retainers’, ’coaching services’ & ’done-for-you’ service lines? (timestamp: 2m 18s)

I am wanting to move away from doing implementation work and more towards strategy consulting. What would be the best way to get started and how can I convert existing clients to do this? (timestamp: 11m 26s)

You suggested that I continue to reach out to Tennis Directors, to get connected. I can do that for some, via LinkedIn. For the ones that aren’t on LinkedIn (but that I have an email address for), what’s a good template to use, to connect with them? What’s the correct approach and CTA to use? (timestamp: 18m 4s)

Would it be too niche to specialize in helping multi-location coworking spaces with their marketing (as a consultant/advisor)? And have an intro tier for coworking spaces aspiring towards multi-location? (timestamp: 25m 25s)

I have a long standing client on a retainer, where the work load has gradually declined. At this point they’re paying me every month but they never call. It’s not a huge amount of money for me. Should I just keep quiet and see if they notice that they’re not using me? Should I suggest they stop paying me? Should I proactively reach out and try to increase the level of engagement? [I have a conflict so am not on the call, sorry] (timestamp: 30m 25s)

I’m interested in offering 3 pricing tiers on a proposal. In the past I’ve always offered a single, flat rate, but I’m wondering about the best approach to differentiate the offerings. I usually think in terms of features or amount of work to be done, but I’ve also heard about removing risk to the client as you move up the tiers. Just curious about some examples you could give on how this could be presented. (timestamp: 36m 37s)

I haven’t done any strictly advice based consulting before, usually I do discovery/implementation, but was asked during a networking event if I would come in to advise a company . We got cut off and he left before we could flesh out details but I plan to follow up. Do you have any advice on pricing this? (timestamp: 47m 38s)

  1. Should I consider increasing the scope of work that Videobites delivers? 2. Is only creating “training” videos hindering the opportunity? 3. Or will diversifying my service reduce my expertise and value? (timestamp: 61m 13s)

Sales conversation transcript teardown (timestamp: 78m 7s)

I have a lead who wants to hire me to help advise them on a fairly large capital purchase (somewhere in the $200K-$500K region). I’m an expert on both the technology and the vendor they’re probably going to select. They want advice from an unbiased expert to make sure they purchase the right equipment and services for their plans. How would you approach pricing something like this? (timestamp: 2m 2s)

What can I do on my website since I don’t have any good testimonials yet for social proof? (timestamp: 14m 56s)

Can you review my LinkedIn tagline? (timestamp: 31m 15s)

Do you have any recommendations for long term support of a custom software solution for clients. Specifically, on-going small (low value) tweaks, small tweaks with high value and planning/pricing version x+1. (timestamp: 42m 19s)

I’ve got a client that I had a roadmapping session with, followed by a $75K proposal. This is a company looking to increase monthly revenue by $100K by doing online marketing (they currently only sell offline). They said the price was high but they were still interested and would get back to me last week. I followed up with them on Monday but still haven’t gotten a reply. How can I try to salvage the deal at this point? (timestamp: 48m 34s)

Can you provide any suggestions on implementing and pricing GDPR compliance for clients (news sites, blogs, recruitment agency). Not sure if there is anything I can learn and do as a web developer or if I should be referrring them to a lawyer/GDPR consultant. From what I’m seeing online, it looks like lots of sites are going halfway and are not really fully compliant. (timestamp: 62m 43s)

In light of the list of potential offerings you posted in Slack, what should I do next? (timestamp: 3m 23s)

Had a “no-show” call with a referral yesterday. Is there a good system to weed out the tire kickers that I ought to implement? (timestamp: 31m 4s)

I am doing a lot of specialty consultant work for my clients but I am trying to figure out how to move away from actually executing the work. How do you delegate this? (timestamp: 36m 35s)

In my specialization direction “sales funnels for thought leaders with digital products” i’m finding its still not specialized enough from convos with bigger names (there are a lot of funnel guys out there) so I think I either need to 1) further specialize skill wise e.g. top of funnel, brand building or 2) further specialize industry-wise, e.g. behavioral science, etc., do you have thoughts there? (timestamp: 42m 25s)

I mainly build internal tools to help automation of business processes. The easiest place for me to look at for the value I provide is savings in labor hours vs doing the process manually, ie 10 hours saved by 10 engineers a week times 50 dollars an hour is $5,000 a week saved. Are there other general areas you would consider when looking at internal tools for estimating the value of an engagement? (timestamp: 49m 29s)

I started my consulting business a year ago, but intentionally delayed building a website to prevent myself getting distracted before landing some paying clients. Now that I’ve proven the concept, I did a website build to create a presence that provides social proof, authority, and makes it easy/enticing for clients to start a conversation with me. Can I get a teardown of the website, with a focus on the value prop/concincingness/calls to action? (timestamp: 56m 5s)

As you know, I’m bouncing back and forth with my vertical specialization idea. I see it’s potential, have made some progress, but I’m concerned that it’s just an opportunity and not something I am necessarily passionate about. Wrapping my identity around it exclusively feels awkward. You mentioned needing to feel some degree of passion, and I wonder if I’m just facing “the resistance” or to what degree it matters that I’m not ultra-passionate about the industry. (timestamp: 1m 41s)

I’m a marketing “consultant” with a whale client problem. Basically an employee as my retainer is for full time hours. I would like to become a real consultant so that I don’t have to trade all my time for money. I recently read TFR and like the idea of productizing a service. I’m introverted and not keen on creating a personal brand, doing speaking gigs, podcasting, etc. Is it unrealistic to think I can position myself as an authority without doing these types of marketing activities? (timestamp: 22m 33s)

I’m struggling with how to connect with additional people in my target market. They have very expensive problems that I am interested in, but I’m not able to find associations/conferences that are in common to them, to allow me to easily get in front of them. Any suggestions on channels to tackle for starting specialization. (timestamp: 34m 3s)

Can you please do a webpage teardown (timestamp: 41m 13s)

Due to your latest podcast I decided to finally publish this page. Not perfect, but could use your insights. (timestamp: 55m 50s)

I’m considering broadening my positioning from focusing on coworking spaces to specializing in helping subscription/membership/recurring revenue businesses with marketing and retention. My approach would be to focus on optimizing the 5 stages of the member/customer lifecycle (my own idea). Then still targeting coworking (and others) with industry and problem-specific landing pages/blog content/conference talks. Am I making a poor choice, is this too general? (timestamp: 1m 30s)

This might just be a “yes” question but, in slack someone mentioned a $450k project (going for “hell yes” value I think) and my question is, would you still ask for that as upfront? Would you ask that expecting they would come back with x payments over y months? (timestamp: 10m 34s)

I sell consulting services today and will be selling products later on. My marketing strategy is focused on content marketing. I am building out my website and I wanted to know what are some key tactics for your homepage layout? (timestamp: 21m 24s)

I currently do fixed prices for projects but have struggled to genuinely value price. I’m working with telephone companies and I’m usually talking to (e.g.) Director of Operations about a network upgrade (to put it in IT terms). My clients motivation to make changes usually comes from problems with current equipment or End-of-life situations. They need to do these projects to maintain their current status quo - but I find it hard to really assess value. Advice? (timestamp: 33m 38s)

I currently price by sprint and want to switch to value based. I do interact with the “CTO” role typically. I am meeting with a client to start discussing v2.0 of their system and plan to approach this value based. I plan to direct the conversation towards objectives/measuring success/value as opposed getting a list of todos and present a 3 option proposal etc. Is this the course of action you would recommend for transitioning? Is there any additional advice or strategy you would recommend? (timestamp: 43m 43s)

You’ve been a FileMaker developer before. I am, still. My primary skill, and source of new clients, relies heavily on my identity with that market. What “productized” services should I first focus on as I seek to rely less on selling solutions? (timestamp: 51m 11s)

I’m a bit stuck - my “generalized” consulting practice is approaching multiple 6-figures with only a handful of clients, and my foray into specialization in coworking spaces is proving to be a big demand on time and mental bandwidth. My hunch is that I’m not solving an expensive enough problem and the road to profitability on that front is long. Should I focus on my more lucrative consulting and reconsider my vertical specialization? Or keep pushing on my daily emails until something clicks? (timestamp: 2m 11s)

I have never tracked my time. I can see how this is maybe unnecessary for value priced or strategy projects, but I’m very much focused on implementation currently and am thinking it might be a good idea to start! What are your thoughts and have you any tips on successfully doing this? I’m concerned I’ll spend too much time remembering to track the time rather than doing the work. Cheers, Ant (timestamp: 21m 36s)

My client paid for a project 6 months ago and never got around to doing the pre-requisite work. He is done now, can be very pushy and everything is urgent for him. I pushed back on him because I did not want to him to control my time even though the specific task was small. What’s the best approach for handling client expectations like this? I am having trouble organizing my time better with multiple clients. (timestamp: 27m 23s)

How would you structure content marketing if your product is technical but the purchaser is probably nontechnical? Example: I’m looking to provide backups for SaaS apps as a productized service. I could write about how I would back up a MySQL database, or how I would help you design a disaster recovery plan (understandable by nontechnical folks). Some people have said devs will refer you to their boss, others have said “that never happens.” (timestamp: 42m 4s)

I’m starting to write daily to see if this is something that works for me. My thoughts are pretty random right now and what I’m writing seems to be all over the map. I have identified my target audience, so that helps, but still, it feels like I have very little continuity. Any tips on finding a voice? (timestamp: 56m 7s)

I decided to position myself to help salesforce powered businesses be more efficient. Clients have signed up for custom software development that integrates into their salesforce so that all the data is in one place. With a positioning focus around technology, should content and articles be more technical focused or business focused? (timestamp: 1m 37s)

I’m struggling to keep up with a daily email writing habit. Mostly because it’s taking be over an hour to write something. Should I try to simplify my emails or do you have a mindset I should take into account when writing them? (timestamp: 15m 39s)

How would you recommend making the most of a speaking opportunity to my ideal audience but on a topic that is not my area of expertise / the service that I sell? (timestamp: 24m 10s)

For our new “info product sales funnels for influencers” page I’m building a quiz as the call to action that will generate a report based on user inputs related to marketing/product dev sophistication, revenue/list size and their personality. Am I getting too complex with this? Would you recommend just starting with something simple like classic sales copy + “schedule a call” or “view pricing” (for productized service) ? (timestamp: 33m 0s)

I am still on the fence about the proposal/roadmap document. What’s your latest thoughts about it: single page vs. 50 page? Does it depend on how much they paid you for it? (timestamp: 41m 2s)

I am wondering if you could provide me with direction as a photographer. I tried to set up my website in a different way from other photographers, but think it’s potentially over the top. I have a couple ideas on what to offer as an intro email series as I want to do email over blog. Website is (timestamp: 50m 46s)

Can you talk a little about creating and implementing an introductory email series as a call to action on a home page? No specific questions, as I’m just starting, but anything that might help make it more effective and avoid common pitfalls. (timestamp: 3m 32s)

Would you recommend selling a productize service and roadmapping side by side, or should they be standalone to avoid confusing the situation? (and maybe create another personal consultant style website where I do offer strategy?) (timestamp: 15m 26s)

How do I migrate from one specialization to another? I want to continue accepting customers in the old focus, but start driving customers to the new one. (timestamp: 23m 33s)

I’m a software developer and I’ve fired my biggest client then realized that I only have about 2 months of runway and I don’t have a lot of past clients to reach out to. What would be your next steps to secure revenue with the right clients quickly? (timestamp: 32m 42s)

I’ve been doing daily emails for a little over a week now and have had good success so far. People are clicking, opening, and replying to my emails. Remind me, why do you send live daily emails instead of creating an evergreen workflow that every subscriber goes through? And would you recommend having them onboard with a series of 10 or so emails to get them “indoctrinated” into my way of thinking? (timestamp: 50m 33s)

Curious on ideas to make website maintenance worth my while. I know it’s not high-value, but wondering different ways to propose it so it’s not billed as hourly. My clients are used to this method, but curious of what I can do for future clients. (timestamp: 53m 7s)

How to find what are the pressing problems of your target customer and which you can solve with your skills (timestamp: 57m 13s)

You have mentioned recently how the first financial engagement with a client will always be the most profitable and then it’s “downhill from there”. Can you speak more about this? In a recent situation with me, my profits with one client have gone up because they’ve developed more trust (so there’s less resistance to payment) and also because I’ve practiced the work it is quicker for me to deliver and therefore I have higher profit margins.

I have been freelancing for 3 years. Things are moving in the right direction but business is still maturing. I know I should focus on one thing at a time, but I am considering starting another business at the same time. The plan would be to spend a few hours a week on it. What is your advice on growing a second business whilst focusing primarily on a main business?

Feedback On: Delivering simple, accessible, data-to-people solutions to leverage your PI System Here is the bottom line: Your data is stuck in PI, it requires expertise to access and share, which is causing you to miss a huge opportunity. Subject matter experts, the people making key decisions, need to use and visualize your PI Data. This must be as simple as possible, not requiring training, or special tools. It should be as easy as opening a browser or mobile device and seeing the answers.

I’m considering sending daily emails to my small but growing email list in my niche market, but I don’t know where to begin, and I am also somewhat concerned about whether I will have the discipline to keep it up over the long term. You have given lots of great advice on the subject already, but wondering if you could get specific on first steps and your mindset when you started doing it.

From our discovery calls, the common thread so far is “I have to do it all, I’m not a marketing expert so i need confidence to know what to do next” We want to do a catch-all online sales process audit with recommendations as our initial productized service but $1799 seems VERY low for the value. Are we shooting ourselves in the foot? Is there a better approach?

I have settled on a horizontal focus (i.e., software training videos for SaaS owners) but I’m not getting a lot of leads. What should I do next? (timestamp: 2m 23s)

If you could promote one thing (a remote service, digital product, etc.) to a niche audience, what would it be? All of your podcasts, content, etc. would promote this one thing for all of your income (ideally recurring revenue, low ongoing stress). (timestamp: 22m 41s)

Do you have any tips for finding where a target market is talking online? (timestamp: 38m 3s)

When your proposal is rejected but you’re close to 100% sure they should take it, what’s a polite way of saying “Your loss, I’m here when you need me”? I don’t want to try and ’convince’ these guys that they need me, but I want to suggest the alternative is doing things the hard way (I know the alternative they’re considering, and it’s totally the hard way). (timestamp: 1m 52s)

Questions I have are: 1. Do you have a Project propsal template? (not the retainer one) 2. What are your typical steps after the proposal is accepted? Do you create a spec and give to the client for approval or How do you define the scope details? 3. How do you handle support/maintenance? If you give a 6m/1yr support/maintenance as part of the proposal, what after that time frame? (timestamp: 7m 7s)

I’ve recently landed my first coaching client. I wasn’t really considering coaching before, but I love it. I’m billing a fixed price for 2 hours coaching per month with unlimited email contact, with discounts for 3 months payment. What advice do you have for a budding coach, particularly around building a pipeline of prospects? (I’m going to be a litle late joining, so don’t choose this as the first question!) (timestamp: 21m 45s)

Is it so bad to have a horizontal positioning? My main gig is digital strategy consulting for $5mil+ companies who prefer to have a hybrid internal/external team vs. a full-service agency. It’s a unique service model for reasons not mentioned. I know it’s harder to market myself, but I only need 3 clients to break 6 figures (I have that already) and 10 clients to break multiple 6-figures sustainably. Is it simply “the fear” making me hesitant to jump into a vertical with 2 feet instead of 1? (timestamp: 31m 9s)

How do I persuade leads to see the value of fixed-price offers when they are too used to hiring via staff augmentation? Like the habit to estimate a hourly rate based on the proposal and deciding on that and not the value they get. (timestamp: 38m 43s)

When trying to get work from past clients or more work from existing clients or new (super busy) prospects, we often get pressured to just send a proposal. That ends up needing to be revised or gets rejected because we couldn’t/didnt do enough discovery/educating them for the value - do you have any tips for how to manage/insist on having enough discovery in that process to get to the desired outcome in these type of situations to get it right the first time and maximize chance of acceptance? (timestamp: 42m 29s)

I’ve been doing some web dev work for an agency who just went bankrupt. Yes, I lost some money but there is a chance to work with their client directly. It seems like a chance to move the project toward a fixed price approach. But I have no idea what that client’s budget was/is. Any recommendations on how I can get some insight on the $ that’s on the table? (timestamp: 51m 7s)

I’ve found a problem I can help solve. My ideal client has a “hero” office staffer with lots of processes that go through him or her. (I have tools to analyze and visualize this stuff quickly and easily in a way that empowers them and clarifies the picture.) How can I turn that into a vertical? (timestamp: 1m 5s)

Is it too vague or confusing to say you’re a “Marketing and growth consultant for X industry?”. The Growth part allowing me to branch into strategies for client retention, experience, etc. (timestamp: 22m 34s)

i have a 2 part question - 1. How would you go about targeting thought leaders (like yourself) for direct sales outreach? linkedin, open doors by trying to be helpful, etc? 2. How would you suggest I go about trying to generate inbound type leads? e.g. how would you personally go about looking for an improved online sales related solution (timestamp: 44m 31s)

As a designer I produce a lot of annual reports which I enjoy and would like to do more of. Can it be worth focusing on a (sometimes commoditised) service seeing as I would be looking to specialise in it - ie, could that eventually move me away from being commoditised? (timestamp: 2m 22s)

Follow-up question - I currently do most annual reports for the insurance industry which really doesn’t interest me. I’d love to work with the renewable energy sector instead, but I have no contacts there. Should I bother trying to crack a completely new market? My process would be similar, and I could probably address the advantages and outcomes more to that sector than to insurance. (timestamp: 6m 14s)

I’m about to start a 6-month DevOps contract with the Scottish Government. I plan to use this experience to explore whether it’s possible to sell online training courses to them once I’ve left; any thoughts or suggestions about how I can use this 6 months to maximise my credibility and opportunity afterwards? (timestamp: 13m 56s)

Also, thinking about my LFPS, I currently have this “I am a DevOps & Python expert, who helps large companies ship better code faster. Unlike my competitors, I have decades of experience that you can learn from.” I’m thinking about changing the end part to “Unlike my competitors, I have extensive hands-on experience with large companies like the BBC and the Scottish Government. Thoughts? I’m trying to get over that doing things at scale is different to just knowing the syntax for the tools. (timestamp: 18m 26s)

When signing an NDA and maintaining privacy in general, where is the line between sharing what could be considered “competitive intelligence” and what is my own “intellectual property”? (timestamp: 32m 20s)

I’ve taken a first pass (with much anxiety) at a positioning statement and was wondering if you had any feedback? Is the vertical or service offering too broad or unclear? > We create content assets to help personal brands in performance related fields improve their sales velocity. Unlike competitors, we guarantee a specific result by taking inventory of the entire sales funnel, and then use the findings to focus on one point in the sales funnel at a time. (timestamp: 38m 58s)

What are your top tips for discovering a niche’s expensive problems? We’re currently researching online (reading blogs, following influencers and competitors) and reaching out to potential clients to try and book research calls. Got other practical tips? (timestamp: 56m 50s)

I’m going to be proceeding forward with doing some CFP submissions this month. Any suggestions for getting the best chances for being accepted? Is it strictly a numbers game? I’m looking to apply to general business as well as tech conferences, or any really that could look like it would work. (timestamp: 63m 4s)

Based on your advice and recommendations, I’m building a website that is 100% focused on my target market’s industry. My plan is to build an audience first with nothing to sell, then determine products and services for them later. Would you advise for or against creating a free community (using something like or Slack) if I plan to later create some kind of paid membership later? Would it cannablize the paid group or help it? Thanks! (timestamp: 2m 1s)

I’m putting together some online training for the DevOps stuff I do; the online course provider has just added a Pay-What-You-Want option. I’m going to give this a go, but do you have any advice or experience to offer on this pricing options? (timestamp: 9m 18s)

If we have the time: How is the credit union outreach going? (timestamp: 16m 31s)

I have a couple of clients in a similar demographic who have a similar bundle of “basic needs” (keep the server running, administer email accounts...). In both cases grabbing that contract work through a job posting has turned into more interesting opportunities. I figure there are more of these out there. How might I go about marketing such a “basic needs met” package as a productized service? (timestamp: 28m 27s)

You’ve done conf. talks, have books, do podcasts, have magazine articles (read yours in .net mag). Have you found that any one in particular was more beneficial to you than others for landing new business? (timestamp: 40m 0s)

I’m sitting on the fence of working my niche (elite sports clubs/ski teams) and looking for a “job”. Thinking about moving the niche to ski resorts. I have a 3-5 year goal to have 6 SaaS subscription products and a job might enable me to have the 4+ hours a week to work on these products. When I’m hunting for work or doing work, I have not time for my product development. I’m in a position right now where a good client is a paying client. . . (timestamp: 51m 5s)

5 minute answer please- i see recently alot of agencies and lead services for agencies totuting linkedin- my question- im an agency owner and im never on linkedin- so my question is this- if you are to use linkedin as a prospecting tool - its seems like the only people you can reach on linkedin are companies that are also using linkedin to prospect- is this true assessment? (timestamp: 63m 10s)

I’ve had a couple of interesting online and offline conversations this week about collaborating with other independent folk. What are your thoughts about whether this is a good way to amplify the mutual opportunities? Any warnings about what not to do? (timestamp: 66m 47s)

I’ve been reading Badass Your Brand and just had this epiphany. . . I can build most MVP web applications in about 6 weeks. So, why don’t I start with an offer like 25KApps. Here’s my prototype: Thoughts? Once again I find myself being the professional horizontal finder while never finding the vertical. (timestamp: 2m 57s)

I’m taking your advice and focusing on the coworking industry. I currently get a few sparse leads from my small niche website. However, what I want to do is marketing advisory and consulting, and not done-for-you work, and I do this successfully already as a generalist. The problem is they can’t afford those services. Do I change my offer? Sell group coaching? Create info products instead? Or only focus on multi-location spaces? (timestamp: 23m 27s)

I currently have one consulting client in my target market. How do you do content marketing without feeling like you’re giving away their intel? They are onboard with me specializing in their industry but I fear the idea of leveraging the experience gained with them and giving it away to potential competitors, making them upset. (timestamp: 32m 8s)

My SaaS business has acquired about 100 subscribers organically, but I have a strong sense that I need to start doing direct sales. Sales is not one of my strengths. Could you talk through the right approach? Example scenario: We sell training videos and want to get Heroku’s team of frontend engineers signed up. (timestamp: 40m 19s)

I don’t have experience dealing with larger firms; my experience in my own business has been with smaller clients. Can you compare and contrast the experience of selling to clients with larger budgets with selling to smaller clients? (timestamp: 46m 10s)

I read and appreciated your emails about your LinkedIn outreach to credit unions. Have you got any “Wish I knew that before I started” or additional points to share now in retrospect? Thanks! (timestamp: 52m 59s)

I’d like to ask for your feedback on the following LFPS attempt: “I help infosec companies to protect high-speed datacenter-to-datacenter Ethernet networks”. Now with the ’unlike my competitors’ part I am struggling to fit the following options/benefits: a) help to go through a complex certification process b) eliminate vendor-lock by releasing full source code and design materials c) using hardware accelerated cryptography to deliver a higher-margin products. (timestamp: 57m 48s)

We have 1200 email subscribers, and I’ve been bad about forming a community with them. One of my goals this year is to email them more regularly and frequently. I’m having difficulty getting folks to engage - to write me back, tell me their frustrations, etc. What are some techniques or strategies to help me engage with my audience so I can understand how best to serve them? (timestamp: 67m 4s)

I want to try out a new productized service and I have a client in mind who could beta test it. It’s similar to your slack room, where me and my business partner would make ourselves available to help out an engineering team with UI development questions they have. How should we go about piloting this, and discovering the price? (timestamp: 72m 52s)

How do you deal with value pricing customers in a relatively close knit industry when you know there is differential value for different customers? What if the customers talk to one another? Do you have thoughts on this? (timestamp: 2m 2s)

What way do your credit union customers go in your funnel for getting on your most expensive retainer? Do you know them personally before? Have you worked with them before? (timestamp: 6m 58s)

You recently talked with Kevin in Slack about your writing process, and I appreciated the discussion. In the early days, did you ever struggle with what Philip Morgan calls The Fear? I imagine your “sun” could have been any of dozens of topics - how did you commit to one central area of expertise, and resist the temptation to change direction before you had an audience? (timestamp: 15m 13s)

I currently work with a small team of devs to deliver projects. Projects typically last 2-9 months. I’m acting as the salesperson, project manager and product manager for all projects. I’m getting to the point where I can’t handle the client facing stuff all on my own. How do you think about team structure as you grow the business to handle more projects at once? How would you structure the team? (timestamp: 30m 59s)

When someone goes silent for months like that, do you ping them? or do you just sit and wait? Do they feel like they’ve been ripped off after they remember they have you? (timestamp: 39m 7s)

Do you have suggestions for how to determine the value of (specifically) design work to clients so as not to be taking mildly educated guesses, or is that just the reality of this approach to pricing? (timestamp: 47m 13s)

I’m really having a challenge converting existing clients from hourly billing to value-based billing. I know you cover this in some of your content, but any tips? (timestamp: 1m 34s)

Any tips for when running projects where your team is also outsourced / sub-contracted onto a project? Do you move them over to value-based billing? (timestamp: 8m 29s)

I struggle with how to word an invitation to chat about a businessperson’s problems/felt needs. Can you give me some context about why this would be an appealing request for someone, what they might get out of it? (timestamp: 15m 24s)

Earlier this year, a real estate broker hired me to write software to consolidate his various tools into a more streamlined workflow. His two goals at the beginning were to serve more clients and to attract new employees. But later, he talked more about spinning off the IP into a new tech company, finding investors, etc. Eventually the budget ran out, and the tool was never used. He wants to meet again to talk about “finishing the software”. How would you approach revisiting a project like this? (timestamp: 23m 18s)

I currently advise on and/or manage digital strategy for clients in a variety of industries. My best client is in the coworking industry, and I have considered going into that niche to specialize. My concern is I will limit my earning potential or I will need to work with a high number of clients, even though the one client I have pays well. I feel like they are an exception to the rule generally. Am I looking at this the wrong way? (timestamp: 27m 41s)

we are considering offering paid discovery / marketing plans for clients that come into our funnel- we design websites and manage marketing - is there a framework that we can follow on how to offer paid marketing plans/ strategy sessions -what to offer in them & how to do this correctly so we can move our client into our marketing plans- breenan dunn offers something like this, but are there others that have a good framework for this & what are your thoughts on having clients pay for these (timestamp: 38m 27s)

How do you deal with the scenario where you are selling to mid-managers and they need to sell to their senior managers? I can help uncover value with the mid-manager, but they often fail to convey this upward to their managers. The obvious answer is to try get in front of senior manager, but this is not always possible. Are there some hacks to help the mid managers sell the value-based price upwards on your behalf? (timestamp: 46m 3s→)

How do you say “no” to prospects? My filtering process is not working yet and most times I am in a meeting with a new prospect I quickly realize it’s not going to work with them. Like there’s no way to implement a value pricing in their project (for various reasons). However they don’t see any issues and usually are keep asking for making an estimate for their project. Would you recommend saying “no” right there in a meeting? Or maybe start talking about paid road-mapping session? (timestamp: 51m 31s)

I started moving to tech training around building APIs, mainly in a specific tech. Now I was thinking of moving to advisory consulting in this field but with a different audience. Our previous exchange made it clear to me that the audiences (tech managers and biz people) are too different and have different needs, fears, etc. When focusing on building apis for business people, it is still horizontal? Should I add a vertical too? (timestamp: 1m 41s)

We’re having difficulty pinpointing our ideal client. We’ve done a lot of implementation work this year and want to avoid that next year. We’re considered experts in our programming language/framework, so we’re trying to find products/services we could work on for our audience - thinks like trainings, building teams styleguides or libraries, Slack mentoring rooms, etc. What should we do to identify this? Email our list? Experiment with a product idea for someone we know? What’s the next step? (timestamp: 13m 8s)

Do you have any tips on making the decision between two audiences less hard? Personally, I love training and also advisory consulting but have a hard time deciding between them. The only clear thing is that I don’t want to code for someone else :-) (timestamp: 18m 12s)

We’ve helped a lot of companies this year but they seem to take our work/their product and move in a bad direction. We’ve tried hard to have conversations to get them to ask the right questions, but “business needs” pressure them to move quickly, and we see them just plow ahead into the unknown. Are these bad clients? Should we just break up with them? How do we get them to follow our strategic advice? (timestamp: 23m 28s)

Hi Im new to the group- we are a 15yr old webdesign and marketing management agency “generalists” and have seen the light in regards to specializing and niching we are currently looking at a few niches now so my first question is this- is there a step by step framework that exists that we can follow to effectively evaluate and research a niche? (timestamp: 31m 30s)

Investor have awesome expertise in target market but zero experience managing a development of a complex hardware product. External dev team (startup) is failing to deliver. Partly because they don’t prioritize this funded project for themselves and use invested money to cover their own struggling business needs. Investor has already started to micro-manage everything (it doesn’t help though). Are there any options to help this project to succeed (preferably with value pricing approach)? (timestamp: 40m 3s)

If you sign a client on a strategy advisory retainer (marketing in my case), but they don’t already have a formal strategy, is the best approach to advise them on building pieces sequentially or should I create a detailed roadmap/strategy up front? (timestamp: 51m 33s)

I’m looking at religious organizations for my niche as I’ve built church conference level fund accounting systems. I’ve also coached soccer and ski racing for 15 years (in a previous life)--membership organizations. What would be a “niche” in the scope of large churches or upper level organizational units in non-profit/religious I’m also thinking along the lines of membership organizations? Am I being silly trying to link religious/non-profit with membership organizations? (timestamp: 57m 9s)

Advice on moving from implementation work to advisory consutling would be great. (timestamp: 63m 51s)

What do you think of this LFPS? “I’m a Python expert, who helps large companies with an old Python codebase get the best ROI from their dev team. Unlike my competitors, I (<)still working on this bit…)” (timestamp: 1m 54s)

How would you approach a situation with an “ex-startup” that positions itself not being able to afford a consulting services from an ex-employee? (Yes, “we’re broke” discount request). A little twist: they owe me mid-five figures and agreed that I don’t release all the source materials to them until that amount is fully paid. I think about releasing everything anyway to get to the point where they are technically not dependent on me anymore. (timestamp: 14m 16s)

The first part of my LFPS is “I help information-security companies to ship a state-regulatory approved carrier-Ethernet encryption appliances”. What would you suggest for a second part of LFPS when companies are only developing these sort of products internally (those who think they can spend years without any output and others don’t even try). (timestamp: 19m 22s)

I have three tiers of consulting services: 1- reactive advisory 2- proactive advisory + access to freelancer Rolodex (implementers) 3 - done for you digital strategy management (virtual CMO kind of role). My home page copy speaks to the highest tier almost exclusively. Would you advise softening it to include something like “I advise on or entirely manage your digital strategy for you” or was I right to lead with and focus on my highest tier of service? (timestamp: 30m 44s)

Assuming you’ve already narrowed down to a niche market and validated it, what marketing strategies would you suggest when switching from doing mostly subcontract work to getting clients directly? (timestamp: 35m 21s)

How do you enter a new vertical where you have no case studies to show you are an expert and don’t understand the problems and pain points that exist? What is the best way to approach / cold email contacts in that market and ask them to have a conversation to explore the opportunity? I’m completely cold going in to this market but have a huge amount of passion and interest. (timestamp: 41m 23s)

Is there such thing as a “big fat check” that will drive you away from your LFPS area for a year or two? (timestamp: 47m 9s)

I’m trying to decide whether to hire an in-house sales rep / marketing manager to find more leads vs. a 3rd party marketing company who only manages online ads and lead magnets. What factors should I consider when making this choice? (timestamp: 53m 40s)

“Most of my clients have been entrepreneurs who are starting off. They have an idea and I help them succeed with getting there. This is an incredibly challenging audience to target however. Nobody on LinkedIn says “Aspiring entrepreneur”. They have a full-time job typically or occasionally another business (in which case they are CEO). How would you go about positioning yourself when your audience is hard to reach? Or would you position yourself for another audience?” (timestamp: 2m 31s)

“Typically we work with clients who are experts in their domain. Because they’re experts, they can answer all of our “Why” questions. But we end up building software with a list of features for the client that they themselves have more or less defined. Often the software doesn’t solve their problem, so we deliver software that is not valuable, and then the client pivots and tries something else. How do we properly get to the underlying “why”, so we can discover the business goal?” (timestamp: 8m 21s)

“I find it unexpectedly challenging to tune in to clients’ yearly calendar (busy/less busy seasons; when various decisions are made by whom). Do you have ideas on when and how to get this information?” (timestamp: 50m 39s)

“If someone emails us about a low-risk/productized service (e.g. a training), should we have a “why” conversation to see if it’s a good fit, or find out what the goal is?” (timestamp: 52m 26s)

“You mentioned you think of training as a productized service. Do you think training is a good way to get away from time-based consulting? We run a SaaS company but use consulting to bootstrap our business. Could trainings be a better way to fill out our service offerings & fund our company?” (timestamp: 56m 14s)

“I’m still having to rely on hourly freelance gigs to earn money until I make the transition to value pricing. Is it even worth mentioning value pricing in the context of responding to calls for freelancers who always ask your hourly rate? (Sorry I can’t attend the session today - I have a call with someone looking for a freelancer lol)” (timestamp: 58m 58s)

“I work with sensor data, e.g. like from wind farms, to bring value to the business. This usually involves creating management or executive web-based dashboards that are easy to access, understand, and in real-time (updated in seconds). I work with a specialized database, that my customers already have. It is usually difficult for those outside of operations to easily digest this data. I feel this is very general, any suggestions in how to boil this down to an expensive problem, easy to convey?” (timestamp: 61m 21s)

“I sell a highly commoditized service: Outsourced web development for web designers and agencies. My question is what would be the one marketing task that I can focus my attention on to generate leads. Would you recommend linkedin propecting, blogging, or something else? I have a fulltime employee doing the actual work. I’ve never marketed my services until recently when I started a blog and publishing content on freelancing, outsourcing, etc...” (timestamp: 69m 0s)

“Would you be willing to share your tool box list for all the tools you use in your business...crowdcast... hosting. Email. Payments. Etc? You have many landing pages and microsites as well and they all seem to gel together. Extremely valuable to hear the tools of the trade.” (timestamp: 80m 3s)

“You’ve talked about how to move up the altitude of involvement and sell strategy. You’ve also mentioned a strategy engagement (like a roadmap) might be 5% of overall project (say, 5k). Given that implementation is very expensive (and thus brings in a lot of revenue), if we start successfully selling strategy only, how will we make as much revenue as when we were doing implementation?” (timestamp: 0m 52s)

“With value based pricing, I need to determine what the overall value is for the client. Is it realistic to get value based pricing for implementation work? Example: Let’s say that I’m able to figure out that the product’s value is worth around $5 million in revenue for the client. What is a reasonable percentage to figure for how much I should charge? 5%? 10%? 5% would be $250k. Where as the hourly priced implementation might only be $50k worth of development if outsourced. Thoughts?” (timestamp: 7m 29s)

“I realize this positioning statement needs work, but can you tell me what areas you would seek to improve? “I’m a virtual CMO who helps time-strapped CEOs win back their time by managing their company’s digital marketing for them. Unlike my competitors, I work for a fixed monthly fee and guarantee my work.“” (timestamp: 12m 43s)

“We are considered experts in our chosen technology, and it’s how we get lots of consulting leads. Is it possible to value price horizontal specialization? We’ve tried thinking about things like training, mentoring and coaching but haven’t cracked the value pricing nut for these yet.” (timestamp: 34m 40s)

“In a why conversation, one way to discover the value for a client is to find out how much would an employee cost/take to do the project instead. Are there any other techniques (other comparisons one can ask the client to make) to estimate the price of the project that the client would consider acceptable?” (timestamp: 40m 14s)

“Right now I’m spending most of my time on implementation tasks (coding) for clients, because it’s helping me build up a cash reserve. It’s good to be busy, but I want to free up some time and mental energy to think about the future. Would it help to try delegating to junior developers, or will that just create new problems and more work? Do you have any more general advice on how to start freeing up time without cutting off too much short-term revenue?” (timestamp: 45m 45s)

“When a project is finished, it doesn’t generate revenue (and profit for the client) immediately, but over time... When estimating the value of the project for the client, do you take a look how much profit they would make in a year (let’s say 1 mil) or in 2 years (let’s say that would be 2 mil) or in 3 years (3 mil) as that’s a 2x or 3x difference to how much you could price the project?” (timestamp: 50m 8s)

“I have developed a layer on top of an open source platform (Drupal) that significantly reduces the time it takes to build a website and offers other enhancements for content management tasks. Since the time taken to produce sites is dramatically reduce, hourly billing makes no sense. Are there key factors to consider when working out value-based billing for production services based on open source technology? (I.e. where there is not full control of the IP.)” (timestamp: 51m 48s)

“I find it challenging to think clearly about dollar amounts at the scale that businesses larger than mine operate at. I’ve had a number of 5-figure projects over the years, but it’s hard for me to internalize the fact that a business could justify spending half a million dollars on something. I’ve talked to potential clients who couldn’t afford a few thousand for software development. How can I develop better intuition about the amounts of money that larger businesses are operating with?” (timestamp: 55m 57s)

“Hi! What would you do if you were working remotely from a country with lower salaries for a client in US and they’d expect a rate that’s standard to that country (and much lower than US rates)? Hope the question makes sense. Thanks” (timestamp: 2m 41s)

“Should a prospect initially balk when I tell them my rate?” (timestamp: 9m 26s)

“If you’re doing outreach and have several (or many) conversations going across email, Slack, LinkedIn, etc. How do you manage them without getting overwhelmed?” (timestamp: 15m 0s)

“I’ve done quite a bit of thinking on the best vertical for me to hone in on ... this feels like a difficult decision. Can you revisit the industry vertical / horizontal specialty and what questions to ask yourself when focusing on a niche area?” (timestamp: 20m 39s)

“Do you ask the client how much profit they make on each customer? This could come up in an attempt to explain how much value your work is going to be for the client. For example you can expect 10% increase in customers with your work, therefore you will make XYZ profit after paying for your work.” (timestamp: 35m 4s)

“Value based pricing in public sector (working for municipalities, governments ...) Can it work? Any tips?” (timestamp: 49m 17s)

“In reference to the $12k weekend project, would you say that it will only take you a weekend? Can a short time frame undercut perceived value?” (timestamp: 51m 33s)

“what’s your email signature? how do you convert your initial outreach into clients?” (timestamp: 55m 40s)

“Verticals: if you want to focus on multiple verticals, is it best to have separate marketing/websites for each? I would assume so, since that’s how you operate it ( = software devs, = mobile / credit unions)” (timestamp: 59m 14s)

“How do you determine if a client is a good fit?” (timestamp: 60m 54s)

“What is a compelling communication strategy to over come existing perceptions of what I ‘should’ cost and get conceptual buy-in from not only my client contact but also their VP and CEO BEFORE providing a proposal? I want them to accept my higher rates and not feel like they need to consider another consultant.” (timestamp: 63m 48s)

“Is the outreach campaign you have been reporting your entire marketing strategy? Or are you advertising?” (timestamp: 68m 0s)

I’m setting up a productized service for SEO / internet marketing companies where I’ll “health check / tune-up” their new clients’ websites (as part of their on boarding process). I have a flat rate price. What do you suggest on offering bulk discounts? For example - a 5 pack of tune ups at 25% off each? (timestamp: 3m 5s)

I noticed you exclusively offer productized services on your website ( Four questions: 1) Is that how you value price? 2) Don’t you feel like you leave money on the table in some cases? 3) Do you find these easiest to sell? 4) Do you ever do custom engagements? Thanks! (timestamp: 6m 17s)

I’ve been offering Roadmapping Services with our software consultancy and our deliverables have always been tied to the implementation of tools so we never needed to put together a report. Now, I’ve recently incorporated the services into our web development business and I’m curious what type of format/info you provide. If you have a sample or a template you wouldn’t mind sharing - even better! (timestamp: 13m 5s)

Many of my family, friends, and colleagues are not people who make decisions to purchase services such as I might offer. Will this limit the effectiveness of my “magic wand” interview with them? (timestamp: 21m 38s)

I’m struggling with managing my time. I have a couple of ongoing hourly customers and with dead-lines etc.. I’m seeing the reality that at the rate I’m going, moving off of hourly feels like it is going to take a very long time. Any suggestions or tips on how to overcome this? (timestamp: 29m 51s)

Do you find that there is really a minimum company size, whether it be head count or yearly revenue, necessary to offer our services, otherwise, it’s not worth the time and energy? (timestamp: 36m 18s)

Is it possible to do retainers for implementation work without falling into the hourly trap again? Or should implementation work typically be value-based? (timestamp: 42m 14s)

I do digital strategy consulting and advisory. One target market is $5-50mil+ companies looking for the equivilant of a digital marketing manager/advisor, and my other target market is small businesses who tend to DIY more of their marketing, and need guidance on where to focus, what to do, and how/where to find freelancers to help when needed. Do you think it’s confusing to both groups if I target two very different markets like this? (timestamp: 47m 44s)

I’d given up on moving a couple of my clients off hourly, but Tricia reports success. “I moved off hourly billing almost overnight with customers I have done business with for the previous 10 to 15 years. It’s the best thing I’ve ever done.” Do you have ideas on switching existing clients to value pricing? (timestamp: 56m 58s)

How do you respond to the ’But what happens when you’re hit by a bus’ objection? Particularly when selling a large project with some amount of support required down the road. (timestamp: 64m 53s)

What do you think is one or some of the best ways to get street credit for any given industry? (timestamp: 68m 16s)

I want to get completely away from project work and get into consulting (just like you). I’ve never had a consulting / advisory gig before but am very confident I would do well at it. What’s something I could do daily to reach that goal? (timestamp: 4m 50s)

I’ve identified a potential target market that I want to provide consulting services to. They are essentially my competitors. What’s the best way to show my strengths while giving them confidence I won’t steal their business? (I’m a WordPress developer). (timestamp: 12m 38s)

I’m having a tough time deciding on a target market. What things did you consider when deciding on credit unions for your market for mobile consulting? Any tips on choosing a market, other than just choosing something, reaching out to that group, and testing the waters? (I’m a Rails Dev / AWS engineer) (timestamp: 19m 47s)

Follow up Q: I get a ton of referrals from internet marketing / SEO companies. Is it feasible to find other internet marketing agencies who have a WP dev service who might build sites just to get the SEO business? If I can help them build better sites, they might be able to retain SEO clients longer. (timestamp: 33m 7s)

Should I pick a vertical based on who I have connections to, or based on ideas I have about solutions I could provide to various industries? (timestamp: 46m 56s)

I have an idea on how to turn my services into a product, but I don’t want to spend too much time working on it without knowing that other would buy it, I’m thinking of starting small, but struggling on a good approach, kind of open ended question (timestamp: 55m 11s)