I kind of have a secret about this: if you’re an accredited investor, you could 100% take short positions on these shares by borrowing shares from employees and seeking them in one of the random secondary markets that’s out there.

It’s just no one does because the asymmetric downside of going naked short on companies with low market caps (“uh oh, Uber just bought this company for 10x my strike price because xyz stupid reason”)

If you want to get really complicated you can write puts, but good luck pricing them and finding enough liquidity.