By the time I started Ovela, I'd spent a decade leading products across five markets. I'd made hard calls, owned real outcomes, hired and coached teams. I assumed founding would feel like an extension of that, just with more title and more equity. Some of it was. The part that actually surprised me had nothing to do with product skill at all.
The thing ten years of PM work doesn't prepare you for
As a product leader, even a senior one, there's almost always a structure above you (a founder, a board, an exec team) that exists partly to absorb the worst-case outcome of a wrong call. You make the decision, you own the consequence, but the company itself doesn't live or die on your judgment alone. Founding Ovela removed that structure entirely. The first time I chose to start with one specialty instead of broad coverage, there was no one upstream whose job it was to have caught it if I was wrong. That's not a bigger version of a product decision. It's a different kind of decision-making altogether.
Every product decision I made for a decade had a floor under it. Founding is the first time I noticed the floor was there, because this was the first time it wasn't.
What actually changed in how I think
- Slower on fewer things, faster on everything else. The handful of decisions with no real way to reverse them (which specialty, which accreditation partners, what we'd compete on) got far more deliberation than I'd have given similar calls as an employee. Everything reversible got decided faster, because there was no committee to route it through.
- Comfort with incomplete information became a daily requirement, not an occasional stretch. As a PM, "let's gather more data" was usually available as an option. As a founder in month one, it often wasn't. The data didn't exist yet, because the product didn't either.
- I had to become my own skeptic. Every job before this one gave me someone else (a boss, a board, a peer) whose job included pushing back on my own certainty. Founding meant deliberately building that function inside my own head, on purpose, because nobody was coming to do it for me.
The decision to start Ovela with one specialty and a concierge model, not a broad self-serve launch, is the clearest example: it's the kind of narrow, trust-first bet that a decade of leading other people's product portfolios had trained me to argue for, and founding is what made the cost of being wrong about it fully, personally mine.
What I'd tell a strong product leader thinking about founding
Your judgment is probably ready. What's worth testing honestly, before you jump, is whether you actually want the floor gone, whether you want every call, including the ones you get wrong, to land on you with nothing structural underneath to catch it. Ten years of making good product decisions made me confident in my judgment. Nothing but actually founding something taught me what it feels like to trust that judgment without a net.