The Black Swan: The Impact of the Highly Improbable · chapter 1 · id the-black-swan-c1-06-taleb-co-founded-empirica-capi

“Taleb co-founded Empirica Capital in 1999, a hedge fund that used a 'bleed' strategy of buying out-of-the-money options. The fund gained 60% in 2000 during the dot-com crash but subsequently lost money in 2001-2003 before closing in 2004-2005.”

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Wikipedia: Empirica Capitalsource alive
Empirica Capital LLC was a hedge fund founded in 1999 by Nassim Nicholas Taleb in partnership with Mark Spitznagel. Empirica Kurtosis LLC made a 56.86% return in 2000, followed by -8.39% in 2001, -13.81% in 2002, and -3.92% in 2003.
Institutional Investor: Nassim Taleb and Universa Versus the Worldsource alive
Taleb shut down Empirica LLC in 2005, telling people he wanted to become a 'writer and a scholar.' Investor experience was mixed, with early adopters benefiting from crisis gains but facing ongoing bleed that eroded enthusiasm.
Tavakoli Structured Finance: Taleb's Stranded Swansource alive
Empirica outperformed buy-and-hold equity strategies during crashes like 2000 but underperformed in prolonged bull markets such as 2003-2004, highlighting the trade-offs of its convex payoff profile.

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