Is it possible to short startups? Because I would love an opportunity to short Tim Feris, even if only by proxy.
people short unshortable assets in finance all the time by getting the bank or a marketmaker to take the other side in an "over-the-counter" (OTC) agreement.
You just make up the rules and there's a signed document.
i.e. "bets backed up with legal documents".
And... I, for one, would probably take the other side of the bet against Tim Ferris in the short term.
The nice thing about shorting a stock in the open market is that it's easy to peg it to a fall in price.
For a privately held company it's much harder.