These shares weren’t ever worth $7.4m at FMV.

what was the 409a?

Did you really just ask for a 409a in a public forum? You do realize those are closely guarded secrets?

Did you miss the key words of LOAN and 15% APR?

You should be able to get a non-recourse loan, i.e. where you never owe more than the stock is worth. That said, Reddit was one of the more secondary-unfriendly firms, if memory serves correctly, if you didn’t have Board or senior management connections.

it's a non-recourse loan though, so if Reddit didn't IPO and you can't pay, you don't owe money you don't have.