Results: We surveyed 200+ startup founders to find out how much money they have

I think there's a great opportunity for investors to sell "put" options* to startup founders.

*In exchange for "premium" (payment could be made in shares at a future date), person gets the right (but not the obligation) to sell their stock at a fixed price over a specified period of time.

If the value goes up, you lose the premium but keep all your other shares. If the value goes down, exercise the option and sell at the agreed-upon price.

CAUTIONS: (1) clear this with your attorney and tax accountant; (2) if the writer of this option goes bankrupt and your shares plummet in value, you're probably out of luck.

The big ones are all in stock and that has some issues:

There will be tax event when they cash out. You'd be surprised how many people take short term capital gains instead of long term. The reason for that is usually uncertainty about the stock. If it costs you $100K to exercise your options you are going to be reluctant to do that until you can sell. And then you have to wait a year for the long term capital gains tax rate and what if the stock crashes?

tl;dr: $50M in stock is probably around $25M in cash.

One of the most interesting things about this, to me at least, is while the median was on the lower end, the upper echelon of respondents were high enough to significantly skew the mean upwards significantly.

How does Riley accrue 560k in credit card debt?