George Blackman

A business that worked. A founder who couldn’t see it.

From the outside, George had built something unambiguously successful. The Scriptwriting Playbook was selling. The Pro community had members renewing. The free email course kept bringing new subscribers in. The newsletter went out every week. The small products in the background kept ticking along. Revenue was real. Customers were getting value. He had every right to feel good about it.

What he couldn’t do was answer the questions that started to matter as the business got more complex. How were people actually finding him. What path were they taking from the email course to the flagship to the community. Whether the right buyers were ending up in the right tier. Whether he had quietly overbuilt and was paying the cost.

“I’ve just kind of lost track of what my business looks like, what my funnels look like, where the holes are. I just couldn’t picture it from a macro.”

This is the version of stuck that doesn’t look like stuck. The business is moving. The product is working. The founder is the only one in the room who can feel the strain underneath.

The fear underneath the success

Two weeks of quiet sales had George convinced his payment processor was broken.

“I was genuinely convinced that Zapier was broken or Lemon Squeezy was down or something. I was like, why is no one buying it?”

His second instinct was darker.

“What if the course gradually just dips in revenue, and what are the things I could be doing, and how do I stop it from dipping?”

When you can’t see why something is working, you can’t protect it. You can’t replicate it. Every good month feels like luck. Every slow week feels like the beginning of the end. That fear lives underneath a lot of education businesses that look fine from the outside.

George didn’t need a pep talk. He needed someone who could look at the whole machine from the outside and tell him what he couldn’t see from the inside.

Replace guessing with real customer insight

Before we touched a single offer, I asked George how often he sat down with his existing customers to understand them. Not support requests. Not community office hours. Structured conversations about why they bought, what almost stopped them, what changed after.

His answer was honest. Almost never.

So I wrote him a customer interview script built specifically around the Scriptwriting Playbook audience. It covered how buyers first found him, what was happening in their lives when they decided to get serious about scripting, what other options they were weighing, what sold them, where they got stuck, and what new problems showed up after they implemented his work.

He ran the calls. Got the transcripts. We analyzed them for patterns. The result wasn’t a single big revelation. It was a vocabulary. The words his buyers actually used. The triggers that brought them in. The specific modules they kept pointing to as turning points.

“Multiple people had mentioned taking Ali’s course, even taking Ed’s course, and either preferring mine or at most refunding the other one but sticking with my thing. Which felt really good, because I think I have a lot of imposter syndrome around this stuff.”

He had been operating under the assumption that he was the budget alternative to the bigger names in the space. His customers told him the opposite. They had tried the bigger names. Some had refunded them. They had kept George’s.

That kind of data doesn’t show up in your analytics dashboard. You have to ask for it. And you have to know which questions to ask.

Map the offer, not just the course

With real signal from customers, we zoomed out and laid every one of George’s offers on the table. The course. The Pro tiers. The free email course. The newsletter. The small products. Every entry point. Every path.

I walked him through what I call the Offer Sketch, a way of looking at a business across nine components: the core offer, tiers, bonuses, order bumps, upsells, surprises, scarcity, urgency, and guarantees. Most education founders have never seen their own business laid out that way. George hadn’t.

The picture that emerged was revealing. A strong core (the course and the Pro community) with very little structure around it. No order bumps. No post-purchase upsells. No structured downsell for buyers who weren’t ready for Pro. No deliberate surprise moments designed into the experience. The product was good. The architecture around it was barely there.

We weren’t trying to overwhelm him with what was missing. We wanted a clear list of opportunities he could either ignore for now or design against. The biggest one stood out immediately. Move from no bumps and upsells at all, to a concrete path for the customers he already had.

Turn the funnel into something you can see

The map gave us a picture. The next job was making it a living document, not a one-time exercise.

We built a simple revenue model in a spreadsheet. Not projections. Just the actual numbers. Units sold at each tier. Average order value. What changed if a small bump went in at checkout. Then we made a visual funnel map. Nothing fancy. A clear diagram showing where people came from, how they entered George’s world, what they saw next, where the community was presented, where the small products sat in relation to the main offer.

By the time we were done, George had a single place he could look to answer a question that used to take him an hour of digging across five tools. How does someone go from stranger to Pro member in my world.

“I feel like now I can picture it from a macro, and that’s really relaxing because that was a major stress for a long time, feeling like I just lost control, lost my grasp on everything.”

Relaxing. Not exciting. Not motivating. Relaxing. That’s what it sounds like when someone finally exhales.

Build ascension paths instead of new products

The reflex when growth slows is to ship something new. We did the opposite. We looked at what George already had and built deliberate paths between the pieces.

A path from the free email course to the Scriptwriting Playbook, so the on-ramp actually led somewhere. A path from Playbook to the Pro community, so buying the course felt like the start of the relationship instead of the end of it. A path from a 6-month Pro membership to the 12-month tier, with a plan for when and how the upgrade conversation happened.

We also took a hard look at what kind of high-touch work George actually wanted to do. After modelling a few options, he realized that live one-off calls to stare at scripts on Zoom drained him. Asynchronous feedback, where he could sit with someone’s draft and respond on his own time, felt sustainable. That insight shaped how any future premium offer would be designed. Around what he could deliver well for years, not what he could grind out for a quarter.

From no bumps to a real roadmap

At the start, George’s checkout was simple. You bought the course. You got the course. That was it.

By the time we finished, he had a prioritized roadmap of bumps and upsells, with a place for each one to live. The retention-graph database as a checkout bump. A polished script template pack. A set of AI prompts to diagnose draft scripts. Editor Q&A recordings. The Pro community as the post-purchase upsell, with the conversation moved to the moment of decision rather than weeks later through repeated emails.

The work wasn’t picking what to build. The work was sequencing what already existed in the right order, at the right moment in the buyer’s journey, at the right price. Boring, mechanical, high-leverage.

“Having not done order bumps at all, and having then spoken about it and done it last week, it just looks so neat.”

Treat partnerships as a channel, not a bonus

George already had meaningful touchpoints with Ali Abdaal’s Part-Time YouTuber Academy, Colin and Samir, and Spotter. His name was being mentioned in the right rooms. What he didn’t have was a system for what happened when their audiences crossed paths with his work.

We designed one. How his course could sit inside someone else’s funnel as an upsell. What a guest session needed to do to bridge naturally back to Scriptwriting Playbook. What a partner-specific landing page should say so a visitor coming in from the Part-Time YouTuber Academy felt immediately seen, rather than dropped into a generic homepage.

If George was already the “script guy” inside other people’s ecosystems, his business needed to be ready to receive and serve those students smoothly. Predictable leads instead of pleasant surprises.

The exhale

There’s a moment near the end of our engagement that I keep coming back to. George was talking to me from a garden cafe somewhere. His laptop was half in a bag. His microphone kept slipping out of place. The whole thing was unpolished and human, the opposite of a marketing testimonial.

In the middle of it, he said this:

“I feel like now I can picture my business, and that’s really relaxing because that was a major stress for a long time, feeling like I just lost control, lost my grasp on everything.”

Really relaxing. That’s what it sounds like when someone finally exhales. Not a revenue number. Not a sales pitch. A founder who can finally see the thing he built, and it looks right.

A few weeks later, almost as an aside, he added:

“It feels like a success to me already. It’s already changed how I think about stuff. Coincidentally or not, sales have just gone back up again.”

That last line is the one I’d underline if this were a book. The work wasn’t to build more. The work was to see what was already there, and design around it on purpose.