It's certainly possible. The same could happen during private share buybacks that companies sometimes run. I would hope that a company is set up so that manager

It's certainly possible. The same could happen during private share buybacks that companies sometimes run. I would hope that a company is set up so that managers don't have such lens into how many shares an employee still owns. I would take the risk of manager discrimination (which I consider very low) in order to get better liquidity and avoid being illiquid for 8+ years or however long it takes a company to go public.