The risk was not having these things sorted out at the start. It’s pretty standard to have vesting schedules, even for founders. For exactly this kind of situation. Most Series A investors will stipulate such a requirement, and if there was already a vesting schedule it all resets as part of the investment.
Similarly it’s less common, but still not uncommon, to have provisions for leavers. Either some kind of prenegotiated basis to determine how you calculate fair value and buy back the share. Or I have seen something that was more like a reverse vesting in that the ownership expires X years after you leave.
The benefit of sorting all this stuff upfront isn’t just to avoid negotiating at the worst time when emotions are high. The game theory aspect of it requires you to balance not getting screwed with what seems fair if you’re the one that leaves.
Similarly it’s less common, but still not uncommon, to have provisions for leavers. Either some kind of prenegotiated basis to determine how you calculate fair value and buy back the share. Or I have seen something that was more like a reverse vesting in that the ownership expires X years after you leave.
The benefit of sorting all this stuff upfront isn’t just to avoid negotiating at the worst time when emotions are high. The game theory aspect of it requires you to balance not getting screwed with what seems fair if you’re the one that leaves.