Seeing the pitch from the other side taught me more about building than building did

Switching seats

I joined Airtree's Explorer cohort in early 2026, a cohort of about 25 operators learning to angel invest: deal sourcing, due diligence, adding value beyond the cheque.

Most of my career has been on the other side. Building, pitching, convincing someone to believe in the thing I was making. VenueSafe went to me&u, Fingertip to Linktree, and there was a Forbes 30 Under 30 in there too. None of it prepared me for what happened when I stopped pitching and started listening to other founders pitch me.

The gap between the pitch and the work

Inside a startup you remember the chaos. A migration that almost killed a launch. An 11pm argument about the pricing page. Pivots nobody outside ever saw.

Evaluate someone else's startup and none of that is there. You get a deck, some metrics, and a tidy story about getting from nothing to something. Sorting the signal from the narrative is harder than it sounds. You only feel the size of the gap once you're the one doing it.

They pitch product, you watch the founder

Founders spend the pitch on product: features, roadmap, architecture, what makes them different. I did the same for years. I thought that was the thing being evaluated.

It mostly isn't. I kept catching myself watching the person instead. Can they survive eighteen months of things going wrong? Recruit, make hard calls fast, hold their nerve or change their mind at the right time? The product will change. The founder is the constant. Which meant a lot of the time I'd spent polishing features in my own pitches was time I could have spent showing judgement.

Which parts were skill, which were timing

From zero to one you remember making the best call you could with bad information, again and again, until something stuck. From the inside, product-market fit felt like barely keeping up with demand. Watching it from the outside, it reads as a clean line up and to the right.

So you start asking which parts of your own story were skill and which were timing. The honest answer is more timing than I'd like to admit.

Turns out it taught me nothing about investing

Turns out the useful thing wasn't the investing. It was hearing how a founder's story lands on someone who wasn't there for the chaos. Once you've heard that, you tell your own more plainly, and the calls you make while building get a little sharper.

Switch seats, even for a bit. The view changes what you notice when you sit back down.