Another Winter and Another Rebirth

Anthony Scaramucci


Hedge Fund



Episode: 292
January 16, 2023

Episode Description:

Anthony Scaramucci is the Founder and Managing Partner of Skybridge Capital and the SALT conference, and for a brief period in 2017, the White House Communications Director. Anthony and I were scheduled to record a conversation the Friday morning he was named to the White House. That clearly didn’t happen, but we circled back a few months after his return to Skybridge, and that conversation is replayed in the feed. Since then, he invested some of Skybridge’s assets in crypto and last August sold a piece of Skybridge to the now infamous Sam Bankman-Fried.

Our conversation this time around covers Anthony’s deals in the asset management space, his thematic investment in crypto, and unfortunate relationship with SBF. Along the way, we discuss entrepreneurship, risk-taking, maintaining conviction in a downturn, changing your mind, and resilience – an attribute he demonstrates time and time again.

Show Notes
5:02 Deal making
7:58 Price and fairness
10:59 Cryptocurrency and thematic conviction
19:39 Position sizing and opportunity cost
22:12 Getting to know SBF and FTX
36:40 A changing risk/reward environment
40:07 Steel-manning crypto’s future
47:52 Surviving downturns as a crypto investor
50:57 Life beyond Skybridge and crypto
54:02 Closing questions

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