About ten months ago I sat down with Ryan Clogg, whose online education business has since crossed $100M in total sales, and I went into that conversation mostly just curious about how someone actually thinks at that level of scale. Not looking for tactics, more trying to understand the shape of how his mind works around building and systems and leverage.
I pulled the transcript back up recently because a few things he said have been sitting with me longer than expected, and going back through it now, with a bit more of my own scar tissue from building, some of it lands completely differently than it did the first time I heard it.
The part of your business that's winning is probably hiding something
The first thing that's stuck with me is how he described the years they spent pouring everything into acquisition while retention sat almost completely unmanaged, because nobody owned it and nobody was tracking what actually happened to a client after they signed. It didn't matter for a long time because the front end kept printing money, until one month it didn't, and that's when he actually looked at the back end seriously for what sounded like the first time in years.
What got me was the math he walked through, where fulfilling on an existing client can run something like 80% margin since you've already paid to acquire them, versus 40% on something brand new, which means they'd been quietly ignoring the more profitable half of the business simply because the less profitable half was the one making noise.
I keep coming back to that idea that whatever part of your business is currently winning is probably the part nobody's checking for rot, because the attention naturally goes to where things are breaking, not where things are working.
The work and the payoff are never in the same room
The second thing was more of a feeling than a framework, the way he talked about pulling up Stripe charts and seeing entire stretches where they were just building and building with nothing to show for it that month, and then a quieter period that looked like nothing was happening right before the biggest numbers of the year showed up.
The work and the payoff were never sitting in the same month, sometimes not even the same quarter, and there's something in that I'm still trying to actually internalise rather than just nod along to, because everything in me wants the effort and the result to line up on a timeline I can see.
Confidence is built in private, before it's declared in public
The third one is the part of the conversation I think about the most, honestly, because it wasn't about business at all in the way he told it. He talked about a stretch where the business wasn't doing well and neither was he, and he'd genuinely lost the ability to trust that he'd follow through on things he said he'd do.
What rebuilt that wasn't a bigger goal or some grand reinvention, it was getting almost embarrassingly small, waking up at 5am and proving to himself he could do that one thing, going to the gym every day and proving that too, just stacking small kept promises until there was enough evidence built up that he was someone who actually did what he said.
Only once that foundation existed did the bigger, more public commitments start to mean anything, because before that a big declared goal was just another way to disappoint himself in front of more people.
Bonus: the real opportunity is in what everyone stopped noticing
This one came from a question I asked almost as a throwaway, about what he'd build if he had three months to shake up an industry. His answer wasn't about a clever feature or a sharp angle, it was about finding the thing an entire industry has quietly accepted as normal even though it's genuinely broken, and building the standard that eventually replaces it without anyone really noticing it happened.
He used the example of how certain platforms became default infrastructure for an entire industry, the way every restaurant ends up on the same reservation system or every studio ends up on the same booking software, where nobody questions it anymore because it just became how things are done.
The opportunity isn't really in solving the problem everyone's actively complaining about. It's in solving the one people stopped noticing because they assumed it was just part of how the business works.
Where I'm actually at with this
None of this is groundbreaking if you've been building for a while, and I'm not pretending I've fully figured out how to apply any of it yet. But going back through this conversation made me actually sit and ask myself which part of what I'm building right now is winning loudly enough that I'm not checking it for problems, what I've put work into recently that hasn't paid off yet where I'm genuinely still trusting the process instead of just hoping, and whether there's some small promise to myself I've been quietly breaking that's costing more than I realise.
That's usually where the real work is hiding, in the question you haven't actually asked yourself yet.
If your business is running into this kind of chaos, hit reply. I take on a limited number of new builds each month.
P.S. The full conversation with Ryan is on the channel if you want the unfiltered version, including the parts that didn't make it into this issue. [Watch it here]
