Anthony Scaramucci – Another Winter and Another Rebirth (Capital Allocators, EP.292)

Episode Summary

Executive Summary: Anthony Scaramucci discusses entrepreneurship, dealmaking, and resilience through the lens of SkyBridge’s history: buying Citibank’s alternatives business, attempted sales that fell apart, and the fallout from partnering with Sam Bankman-Fried. He makes the case that crypto/blockchain is a long-duration thematic bet akin to early internet investing, argues that setbacks should not deter risk-taking, and emphasizes integrity, relationships, and leaving money on the table for partners.

Main Topics: Entrepreneurship and dealmaking through relationships (Priority: 5/5): Scaramucci says successful deals come from reputation, honesty, and long-standing relationships rather than aggressive hunting. He frames entrepreneurship as a constant cycle of taking risks, failing, and continuing forward. SkyBridge’s transaction history and valuation philosophy (Priority: 5/5): He recounts buying Citibank’s alternatives business via an LBO-like structure, then multiple attempted sales of SkyBridge. His pricing philosophy centers on fairness and preserving partner relationships rather than maximizing every dollar. Bitcoin and blockchain as a thematic investment (Priority: 5/5): Scaramucci explains why SkyBridge entered crypto: he sees blockchain as an early-stage, transformative infrastructure similar to the internet in 1998. He argues the thesis is about long-term adoption, not short-term price action. How SkyBridge sized and structured its crypto exposure (Priority: 4/5): He describes a meaningful but not existential portfolio allocation to crypto, plus related products like an ETF and coin fund. He argues sizing should matter if right over 3-5 years but not threaten the firm if wrong. The Sam Bankman-Fried / FTX relationship and collapse (Priority: 5/5): Scaramucci walks through how SkyBridge met, partnered with, and sold 30% of the firm to SBF, then discovered the fraud. He stresses the importance of describing events as they occurred rather than rewriting history after the fact. Resilience after setbacks in business and politics (Priority: 4/5): He reflects on surviving 2008, being fired from the White House, and the FTX damage. His central message is that failure, humiliation, and volatility should be absorbed, learned from, and moved past. Personal values, mentors, and ongoing projects (Priority: 3/5): Scaramucci highlights mentors such as Ken Langone, Dick Grasso, and Vinny Viola, along with hobbies like reading, his new book and podcast on resilience, and reality TV as outlets outside work.

Key Arguments: Dealmaking works best when it is rooted in integrity and relationships; if people trust you, opportunities come to you rather than through forced pursuit. Fair pricing in deals should leave something on the table for partners, because long-term relationships matter more than extracting the last dollar. Bitcoin/blockchain should be viewed as an emerging infrastructure layer, not just a speculative asset; early volatility does not negate eventual utility. Crypto’s long-term case is stronger after the washout of fraud, leverage, and speculative excess. SkyBridge’s crypto exposure was sized to be meaningful if correct over 3-5 years but survivable if wrong, reflecting a disciplined risk framework. SBF appeared credible at first because of his pedigree, public reputation, and the apparent diligence materials; the fraud was not obvious until the collapse unfolded. Setbacks do not justify abandoning a sector or strategy; investors who swore off tech after 2000 or funds after Madoff missed major recoveries and innovations. Entrepreneurial life requires resilience, humor, and a willingness to keep engaging even after public humiliation or failure.

Data Points: SkyBridge stake sold to SBF: 30% - Scaramucci says FTX bought 30% of SkyBridge. Purchase price from SBF: $45 million - He states FTX paid $45 million for the 30% stake. Implied valuation multiple: 5x revenues - He says the transaction with SBF was priced around five times revenues. Initial crypto allocation: 10% to 15% of portfolio - SkyBridge sized crypto as a meaningful portfolio position. Bitcoin entry price: $16,000 to $17,000 - He says SkyBridge first bought Bitcoin in this range by year-end 2020. Bitcoin target user threshold: 100 million users - He cites this as one checklist item tied to Metcalfe’s law and network effects. Conference attendance: 2,000 people - He references the September 2021 SALT conference at the Javits Center. Crypto event attendance: 2,500 person event - He describes Crypto Bahamas as a large SkyBridge/FTX-linked event. White House communications director tenure: 11 days - He notes he was ejected from the White House 11 days after the job started. Long-term capital management balance sheet: $4 billion - Used as a historical comparison for leveraged failure in financial markets. Long-term capital management notional exposure: $1.25 trillion - He cites this derivative exposure figure as part of the analogy to crypto excess. Backtest on crypto products: Poor performance in 2022 - He says SkyBridge’s ETF, unit investment trust, and coin fund did poorly in 2022. First SALT New York conference under partnership: 2022 - He says the SBF deal was announced at SALT New York in 2022.

Pivotal Quotes: "Leave money on the table for your partners." — Anthony Scaramucci: He attributes this advice to Lee Kuan Yew and uses it to explain his pricing philosophy. "Train the brain to take pain." — Anthony Scaramucci: He says this is the core idea of his forthcoming book on resilience. "If you think I'm going down after the nuclear bomb goes off, then you've missized me." — Anthony Scaramucci: He uses this to describe his own resilience and SkyBridge’s ability to survive setbacks.

Implications: The episode frames crypto as a long-term infrastructure bet, not a short-term trade, while warning that fraud and leverage can distort new sectors. It also reinforces that reputation, humility, and resilience are central to surviving in asset management and entrepreneurship.