Podcast Summary: Making It with Jon Davids

Episode 210 – Anthony Scaramucci Schools Me on Crypto, Investing, and More
Date: September 9, 2025

Episode Overview

In this insightful episode, Jon Davids sits down with Anthony Scaramucci: entrepreneur, hedge fund founder (SkyBridge Capital), and well-known political figure. They unpack topics ranging from the boom of practitioner-led podcasts and the evolution of business, to hard-hitting lessons in crypto investing and resilience after public setbacks. Scaramucci brings candid, often humorous reflections on personal reinvention, the misunderstood value of Bitcoin, and why holding onto great assets pays off.

Key Discussion Points & Insights

1. Reinventing Careers & the Podcasting Boom

(01:00–07:05)

• Anthony’s Multifaceted Career:
  Scaramucci reflects on being labeled everything from a “White House guy” to “the bitcoin guy.” He clarifies his political role as brief and primarily a business networker, not a classic politician.

  • “I can’t really say I was a White House guy, right? I was only there for like 11 days and then I got my ass fired.” (01:15 – Anthony Scaramucci)

• Rise of Practitioner Podcasts:
  Jon and Anthony discuss why podcasts hosted by practitioners are outpacing traditional media. Scaramucci describes the “parasocial” intimacy of podcasting:

  • “When I’ve got an earpiece right up against my eardrum, it makes people feel like they’re in tight with the host… it’s you, me, and the person listening.” (03:22 – Anthony)
  • He credits platforms like Goalhanger for cross-promoting new shows and building audiences quickly.

• Podcast Success Factors:

  • Anthony lauds Rogan for being a “phenomenal listener,” drawing a contrast with hosts who dominate conversations, a recipe for “a podcast going nowhere.” (06:13)

2. Bitcoin & Crypto: Myths, Mindsets, and the Future

(08:09–22:18)

• Personal Bitcoin Journey:
  Scaramucci admits he was skeptical for eight years before investing in 2020.

  • “I was a total naysayer… It took me literally eight years to get my arms around bitcoin.” (08:18 – Anthony)

• Value is Consensus:
  He debunks the notion that only tangible or historically “trusted” assets have value, comparing Bitcoin to the Mona Lisa and baseball cards:

  • “If you don’t accept bitcoin as money… or Mona Lisa is valuable, well, bad news, they’re all valuable.” (13:09 – Anthony)
  • Even money itself is “just a certificate or a piece of paper… your bank account is a database.”

• Institutional Legitimacy:
  He highlights how major financial players have pivoted:

  • “Jamie Dimon… said that Bitcoin is a Ponzi scheme… but now he’s loaning money on it.” (15:03 – Anthony)
  • “Larry Fink hated Bitcoin, did the homework, now loves bitcoin. Ray Dalio… Paul Tudor Jones… Michael Saylor… smarter than me.” (16:25)

• Asset Tokenization:
  The discussion moves to the tokenization of real-world assets (e.g., real estate like Trump Tower), predicting that stocks, bonds, and assets will all move to blockchain rails for faster, cheaper transactions.

  • “$7 trillion per year in the global economy [is spent] on transaction verification… the blockchain… could take that to zero.” (19:00 – Anthony)

• Crypto & Crime Misconceptions:
  Scaramucci addresses the argument that crypto is primarily for criminals, citing transparency and traceability on the blockchain:

  • “If you’re going to do it over the blockchain, you’re Stupid… You’d be better doing it off of [cash].” (21:24 – Anthony, referencing Michael Morell)

• Advisory to Investors:
  He urges those skeptical of crypto to at least learn about it before dismissing it:

  • “I would take 12 hours of my life, learn about bitcoin and at least hear the bull story behind bitcoin.” (16:53 – Anthony)

3. SkyBridge Capital, Asset Holding, and Regrets

(22:52–26:56)

• Evolution of SkyBridge:
  SkyBridge is now “three and a half billion, maybe 55, 60% of it in crypto… We have private equity exposure now, late stage PE, conference business.” (22:52 – Anthony)

• Conferences Still Matter:
  Despite digital communication, in-person events are “hotter than ever.”

• Lessons on Holding Assets:

  • “If anybody can only remember one thing… Hold great assets, don’t be a seller.” (24:07 – Anthony)
  • He recounts regret from selling Apple, Microsoft, Google, and others too early:
    • “I may have made 3x on those and patted myself on the back, John, and left 20x on the table in an effort to exit things too early.” (24:27)
  • The biggest regret among successful investors? “I sold Amazon too early. I sold Meta too early.” (25:28 – Jon)

• Resilience, Mindset, and Getting Up
  (27:03–29:28)

4. Public Setbacks & Resilience

(27:03–29:28)

• Dealing with Public Humiliation:
  Scaramucci reflects on being “kicked in the ass once every five or so years pretty hard,” from the White House exit to the FTX collapse.

  • “If you’ve gotten your ass fired somewhere… chances are you got fired privately… At least I hope that’s not the case [as with me].” (27:30 – Anthony)

• Anthony’s 3 Lessons for Hard Times:

  1. “Who cares?”
     • Life is short and worrying is futile:
       • “Relax. None of us are getting out of here alive.” (28:00)
  2. “Nobody gives a shit about you.”
     • Ignore what others think and stop self-pity:
       • “Get out of the pity party business and get yourself up and go forward.” (28:19)
  3. Mistakes are Universal
     • “Tell me the person that hasn’t made a mistake… and I will identify the liar in the room.” (28:38)
     • “I own it. Be accountable… But don’t be a baby. Don’t have a pity party.” (29:15)

Notable Quotes & Memorable Moments

• “You’re very good at this because you let your guests talk… That’s really where intimacy is.” (03:13 – Anthony complementing Jon)
• “Jamie Dimon… now he’s loaning money on [Bitcoin].” (15:03 – Anthony)
• “Larry Fink hated Bitcoin, did the homework, now loves Bitcoin.” (16:20 – Anthony)
• “I haven’t sold a stick of Bitcoin over five years… Hold great assets.” (24:17 – Anthony)
• “If you want greater evidence that Bitcoin is worth something… the most sophisticated banker… is lending money on Bitcoin.” (15:50)
• “Relax. None of us are getting out of here alive.” (28:00 – Anthony)
• “Tell me the person that hasn’t made a mistake… and I will identify the liar in the room.” (28:38 – Anthony)
• “I don’t wake up in the morning and say, ‘Wow, I did something stupid in the White House eight years ago, let me kick myself in the pants today.’” (29:07 – Anthony)

Key Timestamps

• 01:00 – Introduction & Anthony’s career definitions
• 03:12 – Practitioner podcasts vs. mainstream media
• 08:09 – Anthony’s Bitcoin skepticism and conversion
• 11:43 – Fiat money vs. Bitcoin: the trust/value debate
• 15:03 – Major Wall Street figures shifting to Bitcoin
• 17:51 – Tokenization of real assets & the blockchain economy
• 20:16 – Crypto and crime debate addressed
• 22:52 – SkyBridge Capital’s evolution
• 24:07 – Holding great assets: The lesson from missed gains
• 27:27 – Lessons learned from public failures and moving forward

Tone & Takeaways

The tone is frank, occasionally self-deprecating, but always practical and direct. Scaramucci mixes war stories with hindsight wisdom, encouraging listeners to focus on the long lead—not short blunders—in both investing and life.

Bottom Line

Anthony Scaramucci delivers actionable investing wisdom and hard-won personal insight. If you want to understand the new wave of digital assets, the future of blockchain, or how to recover from being knocked down in business, this episode is a goldmine of real talk and forward-looking optimism.