While researching for new reasons why Taleb is nuts, I came across this story about his former right-tailed man, Mark Spitznagel.

This guy has managed to get 15 investors to ante a minimum of $50 million on a bet that they’ll clean up when the S&P falls 40%. So until then (whenever that is), he is expected to lose money every day in anticipation of that Black Swan event.

This may be the best job ever. He sits in his Santa Monica office doing his downward-dog while being wrong 95% of the time. Can you imagine any other job where you strike out 95% of the time in the realization that you will hit an 800 ft homerun just 5% of the time?

Speaking of home runs… To illustrate, let’s say that I sign a 5-year, $50 million contract to manage the Boston Red Sox and under no circumstances can I get fired. Over each of the first 4 seasons, I win only 8 games (5%) per season while losing 154 per season. My team goes 32-616 under my leadership.

Would Red Sox Nation accept this scenario if they knew that in the fifth year their team would go 162-0 and win the World Series? What if it took 10 years or 15 or 100 years? Is it worth it?

(Note: I might lead the team to a championship but I wont be able to leave my house. Boston fans are tough. So how’d this guy pull that off?)