[TTPrograms]

To you and the other comment - as much as I dislike Taleb's rhetoric, this is precisely the sort of bet he has made a lot of money on. People round rare event probability down to zero, and if you bet against them enough with sufficiently extreme odds you'll eventually (and in expectation) hit a home run.

I would be more than happy to make this bet with anyone willing to take the other side - as in literally, find a modern middle-man system and I'm game.

You may want to be aware that you have provided me a nontrivial arbitrage opportunity, as the odds on predictit are closer to 7:93 : https://www.predictit.org/markets/detail/6611

[runawaybottle]

But would Taleb specifically make a one time bet on one particular Black swan? Isn’t the idea the same as venture capitalism, where this idea only works if you do it with all possible black swans?

You’d have to be crazy to take this one specific bet, you can only realistically take all possible improbable bets.

[TTPrograms]

Choosing to engage in these sorts of bets systematically exclusively and not individually only makes sense if you're not maximizing expected return. You also don't know if I engage in these sorts of bets systematically.