Matt Holmes

Four years in. Still winging it.

Matt had built an education business for self-published authors after COVID wiped out his video production company two months before the twins arrived. He built it in survival mode. He kept building it that way for four years, because survival mode kept working. Real revenue. Real impact. Authors writing in to thank him for the books he had helped them launch.

What he didn’t have was a single sentence he could say out loud about why any of it was working.

“I just feel like I’m winging it a lot of the time. I plan my weeks out in advance, but then it all just falls to crap. I don’t really know what I’m doing.”

Four years. Real revenue. Customers who loved him. And no map. That isn’t a failure of effort. That is what happens when you build something from survival mode and never get the chance to step back and look at it.

The problem wasn’t a lack of information. Matt had been consuming information for years. Podcasts. Courses. Advice from other entrepreneurs whose situations didn’t match his.

“I sort of gaffer taped lots of different pieces of advice together from various different sources.”

That phrase is the entire diagnosis. A smart founder with good instincts, drowning in other people’s frameworks, none of which were designed for his specific business. And the more he consumed, the worse it got.

“I was just getting bombarded with all this stuff. I should do this, do this, do this, do this. And I said, how am I ever gonna sleep? I need to be a vampire, because there’s always so much stuff to do.”

The absence of a plan didn’t just create confusion. It created guilt. When you can’t tell which work matters, everything feels urgent, and you can never feel like you’ve done enough.

Building for the family while missing the family

The reason Matt had started the business was visible in the first conversation we had. He had built it for his family. Now the business that was meant to serve them was the reason he couldn’t sit in the same room with them.

“We build a business for our families, our loved ones, to support them. And if you’re never there because you’re always at the computer, what’s the point?”

He knew the answer. He couldn’t act on it. He grew up watching his own father leave before the kids were awake and come home after they were in bed, and he had built his whole life around not repeating that pattern. The business kept pulling him back to the desk anyway. Up at 3am. Working until the kids stirred. Then trying to be present while his head was still inside an email sequence.

“Last Friday we went out for a walk, Lori and me, for three hours in the forest. And I felt a huge amount of guilt for not being sat here.”

Three hours in a forest with his wife. The whole time, guilty for not working. This isn’t laziness. This is a founder who cares so much about providing for his family that he can’t stop, even when stopping is exactly what his family needs from him.

The guilt fed a deeper pattern in the business. Matt undercharged because he felt grateful anyone was buying. He couldn’t justify raising prices because part of him still felt like he was faking it, and his customers kept reinforcing the ceiling with messages thanking him for keeping things so affordable.

“Everyone said that once they got into the course and the results they’ve had from it, they said well underpriced. You should be charging three, four times what you charge and I’d still buy it.”

The evidence was in his own inbox. He couldn’t move.

An hour that was worth ten years of guessing

In one of our early sessions, I put Matt’s whole business on a single page. Free content to email list to entry-level course to group coaching to one-to-one mentorship. I walked him through the value ladder I use with every founder. The pieces of a complete business were already in his hands. He couldn’t see them from the inside.

“I wouldn’t in 10 years have thought of that myself. It took an hour’s conversation to figure out that some of that could change the whole trajectory of the business.”

That session didn’t add ideas. It reorganised the ones he already had. For the first time he could see the ladder under his feet. He started building an offer calendar. Something each month, planned in advance, instead of reacting week to week.

The first concrete win came from his sales page. The page was the original reason Matt had reached out. He knew the course was good. He could feel the page wasn’t carrying its weight. I did a slippery-slope teardown across the full page, naming the lines that were losing momentum and the transitions that were quietly costing him sales.

“The conversion rate went from about 3 to 3.5%. After working with Craig on the sales page and implementing all those changes, it’s now converting about 6 to 6.5%.”

That win mattered beyond the number. It gave Matt evidence that an outside read could move the needle, and it gave him the trust he was going to need for the bigger, scarier decisions waiting in the queue.

The word I wouldn’t let him say

The longest conversation Matt and I had was about pricing. Not one conversation. A two-year argument stretched across dozens of calls. I challenged him on the original course. On the group coaching. On the new AI tool he was building for authors.

The pivotal moment was a small one. We were talking about a higher price point for the AI tool, and Matt started to say, “But if I’m going that high then I think…”

I stopped him.

“Hold on. I don’t want you to use those words.”

He paused. Tried again. “Okay. If I’m pricing at that level.”

That small correction is the whole engagement in a sentence. “Going that high” frames the price as climbing somewhere you don’t belong. “Pricing at that level” frames it as a deliberate business decision. The words shape the belief underneath, and the belief shapes everything else, from the offer design to the marketing to whether the founder can sleep at night.

Over the next year Matt raised prices across the suite. He added group coaching and a higher-tier mentorship product at price points that would have been unthinkable when we started. He stopped leading with “affordable” as a selling point. And then the audience he had been certain would never pay high-ticket filled the mentorship roster faster than he expected.

The boldest test of all came with the new BookBub course. Instead of recording the curriculum first and hoping it sold, we ran a paid cohort before the curriculum existed. People paid real money to learn the material live, on a price tag set deliberately high, and Matt taught the course into existence with real buyers in the room. The course was validated before a single lesson was recorded.

The simplest advice that was the hardest to take

The other thing I told Matt was easier to say and harder to do. I told him to stop working on Sundays.

No framework. No phased approach. Take one day off per week. His wife Lori had been asking him to do it for years. It took someone outside the family, someone Matt respected as a business authority, saying the same thing for it to land.

“My wife, Lori, has told me to do it a few times but I’ve never done it. It takes someone outside to tell me to do it.”

He took the first No Work Sunday expecting the business to fall apart. It didn’t. No angry customer emails. No missed launches. No revenue drop. The catastrophe he had been bracing for never showed up.

“I was catastrophizing thinking the whole business is going to fall apart if I don’t turn on that computer. And it’s not true.”

The habit held. Sundays stayed his. He started picking the kids up from school. He started going to the gym at midday because he could. He told me he felt lighter, and that for the first time in years he wasn’t being crushed by his own to-do list.

The exhale

By the time we did the engagement interview, the business looked different at every level. The flagship sales page was converting at roughly twice its original rate. The evergreen products had been moved onto open and closed launch windows, and the largest and most structured launch of Matt’s business had run across a ten-day window. The mentorship roster was full of buyers from the same audience he had been certain wouldn’t pay for it. A higher-tier course had been validated in the room with paying customers before the curriculum existed.

The shape of the business had changed. So had the founder running it.

“I’ve been winging it for the past four years. And now I feel like I’ve really got some direction and structure to the business.”

The thing he was most pleased about wasn’t his own number. It was an email he forwarded to me that he had received from one of his students.

“I had an email yesterday from someone who said you’ve changed my life and my family’s life. We’ve gone from a hundred dollars for my bookstore to over 5,000.”

That email is the part that gets me. The work compounds outwards. I help Matt see his business clearly. Matt helps an author build a real one. The author’s family lives a different life than they were living a year ago.

“Over time, I’ll be able to extend that to perhaps a full weekend of no work. And then maybe a four day work week. So we’re getting there. Baby steps.”

Baby steps. From a man who worked seven days a week for years. That isn’t a small thing. That is the whole point.