[disgruntledphd2]

The real cost is the tax he would have had to pay up to this point, and I have no idea what that would be.

More generally, Gitlab has done really, really well since then, which definitely wasn't a given at that time.

[SkyPuncher]

These are options, what taxes?

[disgruntledphd2]

My understanding is that upon the exercise of options, one can become eligible for AMT (in the US). There's a similar issue with where I live (Ireland).