Your career compounds like interest but only if you keep investing in learning

The day after high school

I walked into Expense Check and started building software the day after I finished high school. No plan, I just wanted to be somewhere that expected output from day one. Every role since got picked the same way: whichever one I'd learn the most in, the fastest.

VenueSafe, in six months

VenueSafe went from idea to acquired by me&u in six months. It was COVID contact tracing, so it was urgent, and urgency strips out everything that slows a team down. No planning cycles, no alignment meetings, no architecture debates. We built, shipped, watched, fixed, every day. You don't learn to move that fast from a project manager's deadline. You learn it when real people need a real thing and the clock isn't negotiable.

me&u, at 15 million users

After me&u acquired VenueSafe I scaled mobile ordering across their platform: 15 million users across multiple countries, plus the US expansion out of Austin. Every assumption I had got stress-tested. A query that's fine with a thousand users falls over at a million. Turns out elegance isn't clever code. It's boring systems that don't wake you up at 2am.

Fingertip

Then I co-founded Fingertip with Olly Hoffman, alongside Gabby and Hezi Leibovich: websites, bookings, and payments for small businesses across more than 100 countries. VenueSafe and me&u were the prerequisites. Without the urgency we'd have over-planned it. Without the scale instinct we'd have built something that broke the moment it grew. Fingertip needed both, plus a way of thinking in platforms instead of products. A product solves one problem well. A platform sets up the conditions for a lot of problems to get solved, which sounds abstract right up until you're making architecture calls that constrain the next three years.

Then Linktree bought it

When Linktree acquired Fingertip, people treated the acquisition as the goal. It wasn't. It was a byproduct of the skills, the team, and the product all reaching a point where they were worth more at a bigger scale. Now I'm Co-Head of LinkApps at Linktree, building for 70 million creators. The urgency from VenueSafe means I don't waste cycles. The scale instinct from me&u means I build things that hold up. The platform thinking from Fingertip means I see how one feature connects to the rest of the ecosystem.

Under all of it is clarity

One skill carried across all of it: clarity. Knowing the user problem, the first useful version, and what to ignore for now. The environments changed completely. That never did, and zero to one always came back to it.

The compounding part

Every role where you coast is a year of zero returns. Every role where you're a little overwhelmed is a year of high-interest deposits. Returns from urgency stack on returns from scale, which stack on returns from platform ambition. You can't buy it or shortcut it, you earn it by showing up to hard environments for years.

So pick the role that scares you slightly more than it excites you. That's where the rate is highest.