Jan 16, 2023 · 1h 7m · capital-allocators
Anthony Scaramucci – Another Winter and Another Rebirth (Capital Allocators, EP.292)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Ted Seides interviews SkyBridge Capital founder Anthony Scaramucci on navigating the fallout from the FTX collapse, maintaining institutional conviction in blockchain during crypto winter, and cultivating resilience and intellectual humility through public adversity.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Ted holds 14.3% of the talking time here. How this is scored →
Ted as informed peer 3.7 Guest teaching 3.9 Guest disagreement 1.5 Ted pushing back 1.2
speaking balance: gold is Ted, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:03:20 Rejecting Travis Kalanick's Uber pitch
Anthony humorously and emphatically acts out his initial disbelief at the Uber business model, dismissing the concept of putting his daughter into an unverified stranger's car.
Hardest push from Ted ▶ 42:19 Demanding what would change the crypto thesisTed directly presses Anthony on falsifiability, asking what concrete developments would force him to admit his long-term blockchain conviction was mistaken.
Biggest teaching moment ▶ 47:20 Dissecting Buffett's skepticism of AmazonAnthony draws upon firsthand historical memory of the 2000 Sun Valley conference to explain how even elite investors like Warren Buffett miss generational tech platforms when judging them on immediate legacy metrics.
Ted holds their own ▶ 48:35 Referencing Ted's bet with Warren BuffettAnthony brings up Ted's famous ten-year investment wager against Warren Buffett, demonstrating Ted's personal history and the structural beta asymmetry involved in that bet.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Ted as informed peer | Guest teaching | Guest disagreement | Ted pushing back | Why |
|---|---|---|---|---|---|---|
| Dealmaking Philosophy and the Citibank Acquisition | 4 | 3 | 1 | 1 | Ted opens the interview by asking Anthony about his dealmaking history, specifically acquiring the Citibank business and the attempted sale before his White House stint. Anthony answers warmly and candidly, emphasizing compliance, humility, and the Citibank earn-out structure. | |
| Fair Pricing and Wisdom from Li Ka-shing | 4 | 4 | 1 | 1 | Ted probes into Anthony's philosophy on pricing transactions. Anthony shares a formative story about meeting tycoon Li Ka-shing in Hong Kong and learning to always leave money on the table for partners. | |
| Embracing Blockchain: From Ex-Im Bank to Bitcoin | 4 | 5 | 2 | 1 | Ted asks how Anthony transitioned into thematic crypto investing given his absence from the space in 2018. Anthony outlines his multi-step checklist, citing Metcalfe's Law, IRS property right designations, and analogies to the early dial-up internet era. | |
| Portfolio Sizing and Crypto Product Development | 4 | 3 | 1 | 1 | Ted inquires about portfolio sizing, risk management, and opportunity cost around digital assets. Anthony explains allocating 10 to 15 percent and why he prefers being roughly right over avoiding the frontier entirely. | |
| The Rise and Fall of Sam Bankman-Fried and FTX | 4 | 5 | 2 | 1 | Ted prompts Anthony to detail his timeline and interactions with Sam Bankman-Fried and FTX. Anthony delivers an extensive, vulnerable chronology from their initial conference sponsorship to flying to the Bahamas as the multi-billion-dollar hole became apparent. | |
| Sponsor Message: Ridgeline Investment Management Tech | 3 | 3 | 1 | 1 | Following an ad read, Ted asks how the risk-reward profile of digital assets has shifted. Anthony argues the asset class is actually less risky post-washout, comparing crypto blowups to Long-Term Capital Management and 2008. | |
| Testing the Thesis: Bezos, Buffett, and Long-Term Value | 5 | 6 | 2 | 3 | Ted challenges Anthony on what concrete evidence would make him change his thesis. Anthony details institutional capitulation criteria and contrasts Jeff Bezos's 2000 Sun Valley speech with Warren Buffett's skepticism, referencing Ted's famous bet with Buffett. | |
| Navigating SkyBridge's Future and Bankruptcy Buyback | 4 | 3 | 2 | 1 | Ted asks how SkyBridge navigates the present downturn and plans its operational future. Anthony passionately describes buying back the 30 percent equity stake from the FTX bankruptcy estate and compares his resilience to a cockroach surviving a blast. | |
| Ventures Beyond Finance: Politics, TV, and Writing | 3 | 3 | 1 | 1 | Ted checks in on Anthony's outside ventures, including media, writing, and reality television. Anthony humorously recounts filming Special Forces in Jordan and explains his philosophy on training the brain for pain. | |
| Reading Passions and the Dangers of Overconfidence | 3 | 4 | 2 | 1 | In closing questions, Ted asks about hobbies and investment pet peeves. Anthony highlights his book podcast and strongly criticizes overconfidence, recalling a startup pitch where a partner ridiculously promised 100 percent certainty. | |
| Mentors, Early-Stage Bets, and Passing on Uber | 3 | 4 | 2 | 1 | Ted asks about mentors and tempting investment ideas. Anthony names Langone, Grasso, and Viola, before humorously admitting his weakness for backing young founders and missing out on Travis Kalanick's early Uber pitch. | |
| Resilience Through 2008 and White House Dismissal | 3 | 4 | 1 | 1 | Ted concludes by asking for the most challenging career moment. Anthony contrasts the financial panic of 2008 with the personal and reputational trauma of his 11-day White House tenure, reflecting on learning through adversity. |
Statements from this episode (11)
Scaramucci: I plan to hold onto SkyBridge Capital forever
“So I decided that I'm gonna just ride this thing into the sunset, Ted, ok? I'm just gonna hold onto this thing forever.”
Scaramucci: I have zero Form U4 or ADV violations and no personal trading account
“35 years in the business now, knock on wood, no U four violations, no ADV part one or part two. Issues. Don't have a personal trading account.”
SkyBridge's FTX deal was priced at five times revenues
“I think in the transaction that we consummated with Sam, I think it was at five times revenues. That seemed to be where the market was at the time. I didn't ask for six times revenues. I didn't ask for five and a half times revenues. Seems like that seemed to …”
Scaramucci: SkyBridge bought its first Bitcoin around $16,000 to $17,000
“I think we bought our first Bitcoins in the 16 to 17,000 zone, which ironically is where it is right now.”
Scaramucci: SkyBridge allocated 10% to 15% of its portfolio to crypto
“Or you can do what we did, which is a 10 to 15% position in the portfolio, which is sizable in a portfolio like ours.”
Sam Bankman-Fried paid $45M for 30% of SkyBridge with an 85% option
“He bought 30% of the company. It's in the paper now, so it's okay to talk about it. He paid forty-five million for 30% of the company. It was an understanding that he had a right over three years to buy 85% of the company at some point.”
Binance's CZ did not expect his FTT sale to completely collapse FTX
“And again, this is my personal opinion. I don't think CZ thought he was going to collapse FTX. I think he thought he was brushing Sam back. I think he was sending him a message that what you're doing is unsportsmanlike conduct, and the result of which I'm goin…”
Scaramucci bets firm and personal assets that crypto pays off by 2028
“If I stay invested and my long-term thesis is correct, my clients are going to be unbelievably well-rewarded, and this is probably a really good time to buy. I'm willing to bet, obviously, the firm and my personal assets that five years from now, we're going t…”
Scaramucci is negotiating to buy back FTX's 30% stake in SkyBridge
“I'm in the process of negotiating with the bankruptcy people the repurchase of the 30% stake that Sam bought in the company”
Scaramucci: Trump Is the Wrong Messenger to Lead the Republican Party
“I felt he was obviously the wrong messenger for the movement of the Republican Party. You've got smarter, younger, more effective people, more confident, less insecure people to take the mantle of leadership in the Republican Party.”
Scaramucci passed on Uber at a $50M to $100M valuation
“Although I did miss Uber. Travis came to see me, And I think Uber had a 50 or a hundred million dollar valuation at the time, and I was like, wait, wait, what? This is an unknown black car. It's going to pick up my daughter. It's going to drive her around New …”