April 2, 2025
One of my favorite uses of AI
Folks have been asking me a lot lately if I am using AI in my business.
The answer?
YASSSSSSS!!!
I use AI every day in various ways.
One of my favorite usage modes is to have it take a huge amount of data - often the transcript of a Zoom call - and boil it down into useful chunks, takeaways, key insights, action items, and so on.
The beauty of this mode is that I know for sure how good a job it did.
I can tell if it was making stuff up because I was on the call.
(And it pretty much never makes stuff up in this scenario.)
Here’s an example prompt I used to process the transcript of a Ditcherville LIVE Q&A session:
I have the transcript of a Zoom call where I did a bunch of live Q&A. Please go through the transcript, summarize each question briefly, and draft an answer for the question based on my response to it in the transcript. Please go through the entire transcript (in chunks if need be) without stopping to ask if I want you to continue. I’m going to want the final output in markdown format.
Here’s what it gave me:
CHATGPT_RESPONSE_BEGINS_HERE
Question:
I’m planning to offer a monthly subscription for ongoing transformation work. How do I keep it part-time without reverting to hourly billing?
Answer:
Frame your engagement around deliverables, not hours. You have two viable models:
- Fractional Executive / Advisory Retainer – No hands-on work. You’re responsible for providing expert input to a limited number of stakeholders (often just one). Scope is constrained by what you agree to advise on.
- Hands-On Subscription ("All You Can Eat") – Client gives you a backlog, you negotiate which items you’ll tackle in the next 1–2 week sprint. You don’t promise hours—you promise outcomes. If you’re fast, you win. If you overcommit, that’s on you.
Avoid "huge pieces of work." Break everything into smaller, phased wins. If needed, create a high-level transformation map early on (e.g., city block metaphor) without committing to massive deliverables.
Question:
Should I sell only one product per email? What if I email weekly instead of daily?
Answer:
If you’re emailing weekly, your options are limited. You can:
- Always promote the same flagship offer — Use your website or the email’s FAQ to point readers to cheaper or alternative options.
- Use dynamic logic (e.g., Liquid tags in ConvertKit or Drip) — Show each subscriber the next item in your product ladder.
- Mix up how you present the pitch — Vary placement (top, middle, PS), angle (story, benefit, FAQ), or CTA format to prevent ad-blindness.
For maximum flexibility, send daily.
Question:
I have one confirmed beta client and want to get a few testimonials before charging. Should I continue pitching or put up a sales page with a price?
Answer:
Prioritize getting 2–3 quick testimonials first. It’s more important to learn than to earn at this stage. Pitch it manually, gather insights, and optimize based on real-world reactions. A few weeks of delay in monetizing is worth the improved clarity and confidence you’ll gain.
Question:
If I keep tweaking my offer, won’t I look scattered?
Answer:
Probably not. If you don’t have a high public profile yet, no one’s paying close enough attention to notice. The key is the magnitude of the change:
- Tweak = Normal
- Whiplash pivots = Confusing
If you’re transparent—especially on social media—you can frame it as experimentation, not chaos. Think “working in public,” not flailing. Highlight consistent themes like values, worldview, and skills to maintain coherence.
Question:
My client helps founders emotionally, but the surface-level benefit is business growth. Which should I lead with?
Answer:
Test both. Whichever gets more traction wins.
Incorporate Don Miller’s three layers from StoryBrand: - External (functional) – e.g., “grow your business” - Internal (emotional) – e.g., “feel confident” - Philosophical (values-driven) – e.g., “founders deserve support”
You can press all three buttons throughout your messaging. Start with the hook that converts best and support it with the others.
Question:
There’s so much in Ditcherville—courses, podcast, newsletters. What should I do first?
Answer:
I’m working on a guided “start here” experience based on actual onboarding interviews. I want to create decision trees or learning paths based on your situation—not just tagging content by topic. In the meantime, if you’re unsure where to begin, the Pricing Seminar videos are a great foundational start.
Question:
I got great feedback on a project. How do I turn that into a testimonial?
Answer:
You’re in the perfect position. Just follow up with something like:
“You said X in the review—would it be okay if I turned that into a testimonial? I can send you a few questions to make it easier.”
If they delay, follow up politely on a predictable schedule (e.g., every 3 weeks), and casually stay top-of-mind by sending them useful articles or links relevant to their business.
Google: “Building the perfect testimonial” Jonathan Stark for sample templates.
Question:
I want to offer strategic consulting to an industry in turmoil (e.g., video games). How do I validate the opportunity?
Answer:
Narrow down the buyer: don’t target “video games.” Target whom in which kind of company. E.g., "CMO of indie game studios with one Steam hit.”
Look for: - 2K–10K potential buyers - Willingness to take a call (if you can’t get 6 on the phone, move on) - Evidence they spend real money on your area of expertise
Strategic engagements usually fit companies with 50–300 employees. Big enough to have budget; small enough you can reach a decision-maker.
Question:
I spent six months building authority in a niche that didn’t work out. What should I do next?
Answer:
First, avoid spending six months again. You can validate a market way faster using direct outreach, interviews, or small experiments. Don’t try to build authority first—authority follows results, not the other way around.
Next time: 1. Start with conversations, not content. 2. Validate the problem, not just the market. 3. Prioritize speed—test, learn, iterate.
You’ll get better at it each time. Develop the muscle of noticing expensive problems in the wild.
Question:
A client owes me a large overdue payment and is going quiet. Should I continue?
Answer:
Find out what’s going on. Could be an admin issue, could be dissatisfaction. Ask your main contact:
“Hey, I noticed my last invoice is overdue—just wanted to check if something slipped through the cracks?”
If they ghost you, it’s a huge red flag. Pause work until they resolve it. Never chase money and deliver work at the same time.
(And yes, this is why I always say: get paid 100% up front.)
Question:
I want to write regularly, but I haven’t nailed my positioning yet. Should I wait?
Answer:
No—start writing. You won’t get clarity until you start. Write, publish, watch what resonates, iterate. That’s how positioning evolves.
Think of it this way: - Me-centric writing = “Here’s what I’m good at” - You-centric writing = “Here’s your expensive problem”
Either is valid. But you must write. Don’t wait for perfect clarity—it’ll never come.
CHATGPT_RESPONSE_ENDS_HERE
I went though all of these summaries and they’re accurate.
They don’t sound like me but it did a great job summarizing my answers.
Very very useful!
Yours,
—J