Matt Holmes

Four years in. Still winging it.

Just two months before his twins arrived, Matt had built an education business for self-published authors after COVID wiped out his video production company. He built it strong, but it was built in survival mode. He kept going that way for four years, because survival mode kept working.

What he didn’t have was a way to articulate why 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.”

After four years, his customers loved him, but he couldn’t see from the inside what worked, why it worked, and when it might stop working. That’s what happens when you build something from survival mode and never get the chance to step back and gain perspective.

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.”

Matt’s a smart guy 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 perspective and a plan didn’t just create confusion. It created guilt. When you can’t tell what matters, everything feels urgent, and you never feel like you’ve done enough.

Building for the family while missing the family

The whole reason Matt started this business was to serve his family. On top of being a provider, he wants to be there for his young family as it grows. The plan was to have enough time to enjoy them while the business fed the lifestyle, but that hasn’t happened. This business built to serve the family became the reason he stayed so busy.

“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, but the path forward wasn’t clear. He knew he didn’t want to repeat patterns of leaving before the kids were awake and coming home after they were in bed, but the draw to keep coming back to the desk was stronger than he expected. 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, for three hours in the forest. And I felt a huge amount of guilt for not being at my desk.”

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 “fix” was staring him in the face. Now, he just needed to move.

An hour that was worth ten years of guessing

The first concrete win came from his sales page. He knew his course was good, but he could feel the page wasn’t carrying its weight. After I did a full breakdown of the page, naming the lines that were losing momentum and the transitions that were quietly costing him sales, the result was dramatic.

“The conversion rate went from about 3 to 3.5%. After implementing all your 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 on the horizon.

In one of our early sessions, I put Matt’s whole business on a single page. From the free content to email list to entry-level course to group coaching to one-to-one mentorship. I walked him through my Offer Map that I use with every client. The pieces of a complete business were already in his hands. He just 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 just give him more ideas. We reorganized 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 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 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.”

“Going that high” framed his pricing as climbing somewhere it didn’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 you 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’ve been unthinkable when we started. He stopped leading with “affordable” as a selling point. And then the audience he’d 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.

I asked him if he truly thought the business was going to suffer if he stepped away for one day out of the week. After a nervous laugh, he admitted something I already knew.

He took the first “no work Sunday” expecting something to happen. It didn’t. No angry customer emails. No missed launches. No revenue drop. The catastrophe he’d 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. Matt’s Sundays stayed his. He started picking the kids up from school and 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 result

After a few months passed, Matt’s business looked different at every level.

• The flagship sales page was converting at roughly twice its original rate.
• The evergreen products moved to open and closed launches, creating huge spikes in revenue that weren’t there before.
• His mentorship roster continued to sell out from buyers he’d 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 man 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’d 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. Our work together compounds far beyond our coaching calls. As I help Matt see his business clearly, he gets to help his clients build their businesses, sell their books, and enrich their lives.