Business Coaching For Software Professionals

A four month private coaching program to grow your software business.

Attract More Leads • Close More Deals • Increase Your Profits


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If you feel like you need to take your business to the next level but you’re not sure how to go about doing so, I highly recommend Jonathan’s private coaching.

Emily Omier, Full Stack Content


Does your software business feel stuck?

Imagine getting to the next level...

Private coaching will show you the way

My private coaching program is for folks just like you who are looking to increase their profits, attract better clients, and have a bigger impact. If you’re business feels stuck or stalled or inefficient, coaching will show you what’s wrong, what to do about it, and hold you accountable to making progress.


I wish I could turn back the clock and I would have hired Jonathan when I first started my business - it would have saved me years of struggling. I always thought I could do everything on my own - but I hit a wall and realized I needed help to get to next level of my own game.

Geneve Hoffman, 16 Hoops


I would definitely recommend private coaching with Jonathan for people who are open to changing how they work but want to rapidly develop their learning by benefiting from his decades of experience and crystal-clear communication about tricky consulting situations.

Sam Selikoff, EmberMap and MirageJS


Damnit, I wish I had the Stark mojo two months ago!

Chris Ferdinandi


Let’s Refactor Your Business

If you came across a whole bunch of spaghetti code that some novice programmer wrote, what would you do? You’d probably refactor it to be more efficient, more extensible, and easier to maintain.

A good business should have a steady pipeline of leads, a predictable close rate for proposals, multiple revenue streams, and respectable profitability numbers. If you don’t have those things, you’re probably running a “spaghetti business”.

Let me help you refactor your spaghetti business using a proven framework that has been battle tested for more than a decade.

Benefits of Private Coaching

...and a slew of tactics like:


Would I recommend Private Coaching with Jonathan? Hell yeah. He stopped me from making dozens of missteps along the way. Hiring him means protection from the downside and a straighter line to the upside potential of what I’m trying to accomplish. He fundamentally changed the direction of my future for the better.

Kevin Whelan


The Big Picture

TL;DR—You get four months of private and unlimited 24/7 access to me via Slack, phone, or email.

The program includes:

You can contact me any day or time with questions. I reply within 24 hours but usually more like 90 minutes during business hours.

Kickoff Meeting Agenda

Accountability Calls

The Fine Print

Pricing

My private coaching is a four-month program. The investment is $10,000 USD. It’s not uncommon for my coaching students to recoup their entire investment after working together on a single proposal.

You can apply using the button below but before you do, let me first say this...

Coaching is not for everyone. We go deep. You need to be prepared to change habits, routines, and processes that you’ve been addicted to for years.

Change can be scary. It’s hard for everyone. But if you want things to be better, you have to change something. If you think you’re ready, here’s the link to apply:

Apply Now


I would never be where I am now–in this short amount of time–without Jonathan’s assistance. So, the return on investment from that perspective is priceless.

Katherine P


100% Money-Back Guarantee

It’s free to apply and there’s no risk or obligation. If you are accepted into my coaching program, I offer a 100% money-back guarantee. I don’t want your money if we’re not a good fit. If you’re not happy with our kickoff call for any reason, just let me know and I’ll refund your money in full.

But Don’t Take My Word For it...

Here’s what other folks have said:

Amazing talk today, Jonathan! In one fell swoop you have solved a few of my biggest frustrations (niggly scope creep, competing on price, etc.)

Meredith Eisenberg


Jonathan gave me a blueprint of exactly how to lay out a proposal, step by step, follow the numbers. Having this blueprint means now when I create a proposal I just have to follow the plan, check the boxes and I’m done. (Ok it takes a little more effort but that’s how easy Jonathan has made it now).

Casey Stevens, KissAutomation


Jonathan is a wonderful coach. He goes out of his way to help you and will ask and and say the things that – though you might not always want to hear them – are crucial to being successful.

Don Levan, Vanguard CS

Looking For More?

Check out these long-form testimonials from past students:

Testimonial from Kevin Whelan

When I was considering signing up for Jonathan’s Private Coaching Program, I had to decide whether to “go for it” myself and take a risk on my new positioning, or work with him to help reduce some of those risks. Ultimately, it was a value decision. If I didn’t feel like I could get full value for my investment, I wouldn’t have been able to do it.

After working with Jonathan for about 10 months or so, I had a number of “firsts”. These are important milestones for me and I don’t think I would have accomplished any of them if not for specialization. Also, I would not have jumped with two feet into specialization if not for Jonathan, so I owe a lot of this to his guidance.

The following are all firsts for me:

  1. Specialization in an industry vertical (marketing for coworking spaces)
  2. Email list 175+ people (never had a growing email list before as a generalist)
  3. Wrote over 100 articles
  4. Guest on two podcasts
  5. Speaker at an upcoming industry conference
  6. Presented at an industry seminar that people paid to attend
  7. Sold my first info product (mini course)
  8. Started regularly producing webinars
  9. Started and successfully grew my first membership program (to ~20 people)
  10. Sold my first single strategy call (usually only sold longterm engagements)
  11. Started generating incoming leads/inquiries/clients in a market vertical (as opposed to from anywhere)

Getting access to Jonathan’s experience and insights in a highly personalized way was the most helpful. It’s sometimes hard to apply what I “know” to my unique situation, and he helped me in more ways than I expected when it came to the tactics and strategies involved in my transformation to specialization. My website copy got a lot stronger, my positioning became specific and strong, and I made progress on all the goals I had on my wishlist (info products, podcast guest, email list, etc.)

Would I recommend Private Coaching with Jonathan? Hell yeah. Making a transformation of this kind can take many times longer when you go it on your own. He stopped me from making dozens of missteps along the way. Hiring him means protection from the downside and a straighter line to the upside potential of what I’m trying to accomplish. It is great having a sounding board from someone you like AND respect. He fundamentally changed the direction of my future for the better. Thank JS!


Testimonial from Thomas Tuts

There were a few obstacles that almost prevented me from joining Jonathan's private coaching. The first one was that I wasn't sure if my business was in the right place to start with this kind of coaching. The initial introductory call we had quickly made me realize that it was, and that this would be a good fit. The second one, in all honesty, was the investment - I skipped a couple of rungs in the product ladder and went from reading his books straight to private coaching.

I want to be clear here: the investment was most definitely worth it (and has already paid for itself more than 5 times over), and I wouldn't bat an eye at paying the same amount again for more coaching.

As the coaching progressed, I grew more confident both in my business itself as well as my business skills. While I've always had the technical chops, my business skills were a little lackluster. As a direct result, I've started specializing in a niche that a truly understand and love, so I'm excited to see where this road will take me :)

I wouldn't really call it a feature, but it was really cool to see how engaged Jonathan was during the coaching, and how interested he was in my niche (even though it was completely new territory for him). Seeing JS getting all excited for the business opportunities we uncovered confirmed even more that we were on to something great! Other benefits? Accountability (big one for me), general 'brain picking/sparring', his response speed and eagerness to dive deep and help.

Nobody's taken the plunge yet (shame on them), but I've recommended Jonthan's coaching to at least two other freelancers. The 'why' is simple: our time together has really changed my career, and it's headed in a direction that I could only dream of before our coaching. I had a wonderful time during our coaching sessions. Even 'shooting the shit' was really fun and educational in some cases - it was cool to see that it wasn't all 'business'.

I want to call Jonathan a private business coach ninja, but as a karateka he might be offended by that notion :-) Jonathan's private coaching has truly transformed my business - I'm now working in a niche that I truly love and care about. Thanks to our time together, I was able to 5x my investment in less than a year, and I'm on track to have my best financial year yet after our coaching. A+, would be coached again!


Testimonial from Emily Omier

I am a tightwad and I’ve built my business on a shoestring. Before working with Jonathan I think the biggest investment I’d made in my business was $60 a month for LinkedIn Premium. But I also had outgrown my previous coach and knew I needed someone to help me move up the value ladder into more strategic products.

That is exactly what Jonathan has helped me do (in addition to encouraging me to spend some $ on other areas of my business, like my website, so I don’t look like a tightwad to clients).

I also really enjoy being part of the Slack group. Even though my business is somewhat different from the others in the group, it’s great seeing how other people are solving their business problems (and getting their advice on everything from tools to mindset).

Anyway, if you feel like you need to take your business to the next level but you’re not sure how to go about doing so, I highly recommend Jonathan’s coaching.


Testimonial from Brandon Savage

Q: What was one obstacle that would have prevented you from enrolling in private coaching?

Pride. I generally feel like I have the skills I need, but Jonathan proved to me that there was plenty to learn and that I don’t lose out on anything simply for using his skills. I am very happy that I went into coaching.

Q: What did you find as a result of enrolling in private coaching?

I found out the right way to build and test a product for market. Jonathan was patient as I bounced from idea to idea, from audience to audience, and helped ground me through methodical approaches that drove me to audiences that would pay the bills and make me money.

Q: What specific feature did you like most about private coaching?

I liked the fact that every week I had a specific set of tasks to accomplish, and that Jonathan was always available to answer questions. In fact sometimes Jonathan would ask to be updated about something mid-week, which helped motivate me to complete the homework.

Q: What would be three other benefits of private coaching?

I enjoyed the specific nature of the coaching, where everything recommended was actionable. I really appreciated Jonathan’s promptness. And his attention to how I felt and what I needed to feel motivated was important.

Q: Would you recommend private coaching? If so, why?

I would recommend private coaching to anyone who wants to jumpstart their business. Even though in the end I determined the product we worked on was not workable for me, the skills I learned are invaluable. I can apply them again and again to other products, and build out those products for my business.


Testimonial from Sam Selikoff

All sorts of things could have prevented me from applying to Jonathan’s private coaching program... not having some extra cash, not having ongoing consulting work, not being near the beginning of some new potential consulting leads/projects. Fortunately for us, I decided to apply.

As a result, we ended up with:

I especially liked the ability to call on Jonathan whenever a new wrinkle developed with our larger consulting clients. It gave me the ability to navigate tougher situations where normally I feel it would have been easy for me and my business partner to be taken advantage of, not stand our ground, or end up in a contract that wasn’t serving our business needs.

Our bi-weekly accountability calls helped curb some of my indecision. It took a while but the regularity honed my focus. I had to justify to Jonathan every week why we were working on what we were working on. Often I would have TODOs and spend the week working on other things. Eventually I had to come to terms with this, to justify why we were spending time on other things, or be honest about what our true priorities were. We are in a really good spot + focus right now.

I would definitely recommend private coaching with JS for people who are open to changing how they work but want to rapidly develop their learning by benefiting from his decades of experience and crystal-clear communication about tricky consulting situations.

Jonathan is a great “board member” to have in your life. I genuinely looked forward to our conversations every time!


Testimonial from David Trejo

I did not think I was a good fit to be coached by Jonathan because I was not consulting for myself, and had a full time job. I did however plan to go back out on my own again, and wanted to be well-prepared for that (rather than jumping and praying).

Working with Jonathan has made me see the world in a whole new way: I can see value flowing around, and oozing through the cracks in the sidewalk. What does this really mean? I have a much improved understanding of whether a client’s problem is worth solving, and I also understand my own value 200 times better. It is refreshing and life-changing to be able to look at the world and clearly see how I can be a part of it, business-wise. It feels great to have removed the cloud of business uncertainty that surrounds any feature I might try to code up, or any company I might consider working with.

I knew that Jonathan understood the importance of positioning (LFPS) and value based fees. This is why I chose to work with him. I also knew the basics of the two, but applying them to your own business is another thing. He has helped me untangle the finer points of value based fees, using real clients of mine as an example. We have also taken a first pass at positioning, which has been feeling good, despite the challenge.

It has only been a few months, and his advice has almost paid for itself. And this was with me restarting consulting from scratch, in a new vertical. It feels pretty great to see the decision paying off.

I would unequivocally recommend Jonathan’s coaching program because 1) the advice is amazing 2) the program is not over yet, and it has already almost paid for itself.

If you want to keep working at your job the rest of your life, I don’t recommend you work with Jonathan — he will make you want to quit your job, because you will finally be able to see and understand the value of your work. He should have a warning label on his head. His advice will shake your world.


Testimonial from Geneve Hoffman

Before joining Jonathan’s coaching program, I was nervous about sharing my business ideas with anyone - I’ve always done everything on my own - been my own compass. I didn’t think I needed the help either - I have always been the top of my game and I wondered what someone else could teach me. But I had a new idea in new territory (was a photographer, wanted to build a business helping photographers) - and I knew I needed help.

Plus - to be honest, I didn’t really know what a business coach was - I always just thought “you open up a business and then you do it - case closed.” And some of my friends had hired consultants who talked too much about themselves or were overpowering.

I took the plunge after hearing Jonathan speak on Art of Value podcast - I listened to 30+ podcasts on there and the conversational yet confident way he talked about value pricing struck a nerve with me - I hired him (or rather, he let me hire him - haha - he normally works with software developers) after a quick email exchange.

I can’t believe how much I got done in the time that we started the coaching sessions. I realized after working with Jonathan for a few weeks that my biggest obstacle to growth - was myself. I needed to have someone else to be accountable to - someone who could listen to all my ideas, give me unexpected and invaluable feedback, and keep me accountable and on task. I wouldn’t have my new business plan on track without his guidance and resources.

What I liked most was just the way he thinks - the written report, the extra services and chat room are all great - but it’s the weekly coaching calls - just the way he is able to digest what I am saying, quickly fine tune it, and give me insight toward the solution that I found most enlightening. The biggest result I got out of all this was he pushed me into territory I would have never reached on my own - and I consider myself pretty savvy - but he always had me thinking critical angles I hadn’t considered. I always look forward to my sessions with Jonathan - he’s a very down to earth guy, and has a conversational, inviting way of speaking that always keeps us on task but still enjoyable - he’ll even throw in a few Star Wars parables just to keep it real (those are no extra charge, I believe).

There were other benefits as well...

  1. Coaching kept me on track and moving forward;
  2. Jonathan pushed me out of my comfort zone - it’s like I left the small, comfortable pond of my photography world and am having these amazing eye-opening experiences in the wider business world that I would never have had if I had just hired another photographer consultant;
  3. It was so helpful having someone trustworthy, objective and even outside my industry who now knows my brand and my course exceptionally well inside and out - it’s just not the same as talking to a trusted colleague or friend - it’s very empowering to have someone completely outside my sphere that I pay to think for me - he’s part of my new “think tank” - and when you have a new and exciting idea - you need people around you who aren’t going to tell you what you want to hear. Jonathan does this in a thoughtful way. And - bonus round, on day one he totally got my random Silence of the Lambs joke. :)

I would highly recommend Jonathan’s coaching program to anyone - Jonathan has a very real, human way of taking all your ideas and thoughts and experiments and very step by step transforming it all into a vibrant business plan that you will be proud of.

I wish I could turn back the clock and I would have hired Jonathan when I first started my business - it would have saved me years of struggling. I always thought I could do everything on my own - but I hit a wall and realized I needed help to get to next level of my own game.


Testimonial from Katherine P

Jonathan has an uncanny ability to cut through concepts, see through roadblocks and find the gold in any situation. This creates the space to focus on what is really important without wasting time, effort or brain-space on what isn’t.

Other benefits were:

  1. Accountability–even though I am a self-motivated person and unafraid to tackle anything, it was incredibly helpful to be able to touch in regularly with Jonathan to discuss challenges faced and progress made.
  2. Advice from an expert–To speak with someone who has been where you are (whatever level that is) and can offer specific, actionable advice for the unique challenges that you face in your business.
  3. An objective viewpoint of you and the services you provide. Regardless of how much you know (or think you know) about any field, the benefit of having a coach creates a new perspective in the way you view yourself and your business – it’s wonderfully freeing and humbling.

If you are truly committed to the success of your business, I would recommend that you work with Jonathan. If not, don’t waste your time or money.

When I look back on the coaching engagement, I am incredibly happy with the experience and what I was able to accomplish as a result of Jonathan’s advice. I would never be where I am now–in this short amount of time–without his assistance. So, the return on investment from that perspective is priceless.


Still have questions?

Q: How do I know if I’m a good fit for coaching?

People who will get the most out of coaching are folks who have been plateaued and aren’t sure what to do about it. If your intellectual curiosity and talent cause you to wander from task to task prior to completion, and you require more urgency in creating results, you will probably benefit from the accountability that comes with this program.

Q: What do I have to do to qualify?

This program is for people who have clients and income but feel like they’re on a hamster wheel. Making a living but not getting ahead. Unsure of what to do to get to the next level.

NOTE: If you are desperate for work because of cash flow issues, my private coaching program probably wouldn’t be a good investment.

Q: May I speak with a couple references about their time with you?

Sure. Here’s a link to my testimonials page with contact info:

jonathanstark.com/testimonials

Down at the very bottom are links to long form testimonials from past students.

Q: What is the average student’s ROI after completing coaching with you?

The bottom line ROI depends greatly on the student.

At the high end, I’ve had students land deals in the mid six-figures for six months of work and folks landing five-figure per month advisory retainers.

At the low end, I’ve had people not commit to the work and get little direct financial ROI. But even those folks are happy with the educational aspect and sense of control they gain over their business.

Q: How long are the accountability calls?

They’re usually around an hour.

Q: Do we have to use Slack for the accountability calls?

No. We can use a different voice channel if you have a strong preference.

Q: Can we use video for the accountability calls?

I prefer not to use video for accountability calls because I take a lot of notes during the session. I find that video tends to slow things down and can be distracting.

Q: What happens after I pay?

Once you complete your purchase, you’ll be presented with a calendar link to schedule a kickoff call. On our kickoff call, we will agree to a game plan, share private contact info, set your first assignment, and pick a regular time for our accountability calls.

Q: I still have questions!

Just shoot me an email and ask: jstark@jonathanstark.com

Who wrote this page, anyway?

Hi! I’m Jonathan Stark and I was a software consultant for the better part of fifteen years. I’ve given sold out talks on three continents, I am the author of five books, and I have helped brands like Staples, Time, T-Mobile, and others with their software strategy, tactics, and training. (You can check out my press page for more info.)

Jonathan Stark

In my first year as a solo consultant, I doubled my income by ditching hourly billing for value pricing. I have over a decade of real-world experience successfully applying value-based theories to my own consulting work and that of 100+ business owners I have counseled. These days I routinely command an effective hourly rate of $2000+ per hour.

The unconscious acceptance of hourly billing as the best and only option for selling services is a collective hallucination that literally keeps me up at night. In fact, I consider it my mission in life to rid the earth of hourly billing. Care to join me? You’ll be glad you did. 🙂

Now is the time

I think it was Thomas Jefferson who said, “If you want something you’ve never had, you must be willing to do something you’ve never done.”

Don’t waste another year moving one inch in every direction.

Apply Now

Don’t worry, there’s no risk or obligation and it’s free to apply.


Act Now. Seriously.

Availability is limited. I usually only take on a handfull of new private coaching students per year. If you are considering private coaching, apply now to start the process.


I’m actually winning projects at 10x the hourly rate I used to make. In the past quarter, I banked six months salary. Honestly, the feeling of knowing you have 6mo in the bank is freedom beyond anything I have ever experienced.

Marcus Blankenship