Don’t EVER work for a company that will take your shares if you quit. It’s a psychological trap and you are the prey. Any startup owner that strips your stake if you leave deserves to become the personal target of an obsessive and vindictive IRS auditor.
Generally I think the trade is that you can keep the stock if you quit but you don’t have stock. You have options that expire if you quit, so if you want the stock you must pay a lot of money to exercise the options, and you then pay tax based on gaining a high value of stock (potentially more tax than you could afford) even though its real is quite undetermined.
In other words, the company takes your shares if you quit.
The solution is to put the option strike deadline at 10 years in the future which is iirc what YC recommends. It's possible for these terms to be employee-friendly.
Most of the time it’s not vindictive founders. It’s that the options cost money to buy. And if the company is successful one might have to pay taxes on the stock options too.
