Thats different than being an uber early employee and knowing your private equity is worth a ton. I also wouldn’t exercise random startup shares unless they were real cheap and I wanted to roll the dice. The uber example is clearer. I’d always rather be a paper millionaire than not a millionaire at all. At least you have the choice to exercise some if you leave, or all if you can afford the loans. Also uber is a bad example since people DID sell their private shares as there was enough of a marketplace for it.