[throwaway2016a]

My problem has always been that startup pay is often below market and when you are already making below market, shelling out $20k to exercise is prohibitive. In my case that would mean spending more money than I put on the down payment of my house or pay for a year of my kid's daycare.

With that said, if you can afford it it is a great way to lesson the tax blow in the event of an exit.

[Clubber]

From what I understand, a banking or trading institution will execute the transaction, leaving you with the net for a moderate fee.

[throwaway2016a]

I'd be curious to know about this. Do you or someone have more information?

Every company I've been at it involves writing a check to the company unless the company is public. I don't know why a bank would take on the risk on a private company.