That's why it makes sense if you're at the seed round and the FMV is still peanuts.
Post-A round makes it much harder.
Post-A round makes it much harder.
You have employees who own shares but need a nontrivial amount of cash to cover taxes. You have investors who may be interested in acquiring more shares (or the company may want to buy them itself). You have a notion of a current valuation of the shares. Broker a sale at a price that's beneficial to both parties.
What is the company's incentive to block such a transaction?
I'd love to see this become standard.
The 10 year exercise window likely makes this unnecessary, but if not he says they will arrange for some form of liquidity.
If there's a good path to the employee owning their shares (or some fraction thereof) outright, that is more desirable in some ways than an outstanding option agreement with a ticking clock.