The angel checks I regret writing

Of the fourteen checks I've written as an angel, three are dead or dying, and every one of them shares the same root cause: I invested in a pitch instead of a person I'd actually watched operate under pressure.

The pattern is subtle. A founder can be genuinely brilliant in a room and still fold the first time a launch goes sideways. I didn't have a way to tell the difference until I started asking every founder to walk me through their worst week, not their best pitch.

None of this is a hard rule — plenty of great founders are great presenters too. But if I only get one signal before wiring money, I now weight 'how they talk about their worst week' over 'how they talk about their vision' by a wide margin.