Two founders pitched me in 2019. University friends. Co-founders since the dorm room. The deck listed them side by side with identical titles. The equity split was 50/50. The handshake had happened on a kitchen table in their twenties and had never been revisited.

I wrote the check and persuaded three other angels to join me in the round.

By the time the Series A approached in 2022, one of those founders was running the company. The other had taken a job at a venture firm eight months in, kept his board seat, attended quarterly, and contributed roughly the amount of effort you would expect from someone whose day job was looking at other people’s startups. He still owned 35% of the business, by which point that 35% was worth real money.

The Series A lead was clear. The cap table needed to be cleaned up. The active co-founder spent seven weeks on a conversation that should have happened in month six. The friendship ended in a law firm conference room in Boston. The deal closed at a lower valuation than it should have because the recap took time, and during that time a competitor announced their own Series A and the lead investor used it to renegotiate down.

I have watched this script play out in at least five companies in my portfolio. Different sectors. Different founders. Identical structure.

Vest with cliffs.

Build performance triggers into co-founder equity.

Have the awkward twelve-month conversation about who is doing what, on paper, in a document both of you sign.

The conversation in month twelve costs a difficult dinner. The conversation in year three costs the company.