[lbotos]

If a company is private then you cannot sell/purchase shares on public markets.

So, execs can go fundraise, which is selling shares to new investors. But what shares are they gonna sell? Newly minted ones, or shares someone already own?

The execs get to decide. In theory, there is no reason that "regular" vested employees couldn't also sell shares if execs designed it that way, beyond some complexity in management overhead (think figuring out information for 1000 people vs 10) as well as "turnover risk" where employees can cash out and leave.

Now you are saying, well, seems like employees are gonna leave now without cashing out, and you are right. That's why it's dumb. Poor decision making by execs. I'm sure there are a lot of people at datarobot that didn't even know this, and are just learning this now.

(Unless execs want both to make a lot of money and re-form the company, if that's the case, well then, great decision making by the execs)