The compounding return on staying put

I've been in the Shopify ecosystem since 2018 and in ecommerce since 2009. Four companies built or bought inside one platform's orbit, one of them sold, one of them dead, two of them acquired and passed on.

The thing that's compounded over those years isn't what I expected when I started. I assumed the return on staying in one market was domain expertise — knowing the customer, the product patterns, what works. That's real and it's the smaller half.

The larger half is that things get shown to you.

What that actually looks like#

I bought OrderBump because the people who owned it knew who I was. It wasn't listed anywhere. There was no broker, no process, no auction. They wanted to sell to someone they'd heard of, and I was someone they'd heard of, and the price was fair rather than maximal because the transaction was also a relationship.

That's not a technique. There's no version of that I could have engineered in a year. It's a byproduct of having been visibly operating in the same small market for long enough that a meaningful number of people have an opinion about me.

The same mechanism showed up in the Vigilance round — I raised from operators in this ecosystem, and the reason I could raise from them at all is that they'd watched me run something else. And it showed up in reverse when Vigilance died: how I handled that is now part of what those same people know about me, which is most of why I wrote about it publicly rather than quietly.

Why people leave anyway#

Every couple of years there's a reason to go somewhere else. A hotter category, a bigger market, a platform with more momentum. The argument is always that the opportunity is larger over there, and it's frequently correct about the opportunity.

What it misses is that you arrive with none of this. You're a competent stranger. Nobody brings you deals, nobody vouches for you, and every conversation starts at zero. That cost is invisible in the decision because it's not a line item — it's the absence of things that would have happened.

I've watched people make that move and be right about the market and still do worse, because they traded an accumulated position for a better-looking one.

The part that isn't flattering#

Staying put has a real cost and I want to name it rather than write a post about how patience wins.

You get narrow. Almost everything I know is about ecommerce, DTC brands, and Shopify. When I look at anything outside that, my judgment isn't worth much, and I've had to learn to say so — it's the main reason I pulled back from angel investing outside this space. My opinions were being taken more seriously than they deserved.

You inherit the ecosystem's ceiling. However well I execute, I'm bounded by what happens to this platform and this industry. That's a bet I've made four times over and it's concentrated in a way that would look reckless in any other portfolio.

Your reputation is also your constraint. People know what you do, which means they show you things that fit what you do. The deals that get brought to me are ecommerce deals. There's an entire class of opportunity I never see because nobody thinks of me for it, and I have no way to measure what that's cost.

What I'd actually tell someone#

The compounding is real, it takes about five years to show up, and it shows up as deal flow rather than as skill. If you're two years into a market and considering leaving because it feels like you've learned it — you've learned it and you haven't earned it yet, and those are different clocks.

But pick the market on purpose. Staying put is only compounding if the ground under you is growing. Otherwise it's just a long commitment to a shrinking room, and the same reputation that brings you deals will keep bringing you deals in a category that stopped mattering.