Whether you can sell something to cover the taxes just doesn't seem relevant to the IRS!
Whether you can sell something to cover the taxes just doesn't seem relevant to the IRS!
The changes aren't usually zero -> something, but that's a footnote to the general principle.
I'm not a financial specialist, but googling[0] suggests that you can, say, use restricted stock as collateral for loans, at least under some circumstances, so the situation is slightly more subtle than having (currently) worthless pieces of paper that you have to pay tax on; not that I'm saying that the IRS is necessarily right.
Surely brokering such sales (to accredited investors) is a profitable opportunity, so someone should be doing that. Charging a few % sounds like a reasonable fee for brokering rather illiquid securities. Not just in silicon valley which mints huge quantities of fresh private equity.
At least large VCs should see it as an opportunity to increase holdings at a discount as employees inevitably rotate in the company.