Podcast Summary: The Prof G Pod – First Time Founders with Ed Elson: How Anthony Scaramucci Became The Mooch

Date: October 5, 2025
Host: Ed Elson
Guest: Anthony Scaramucci, Founder and Managing Partner, SkyBridge Capital

Overview

In this episode of First Time Founders, Ed Elson sits down with Anthony Scaramucci—a legendary Wall Street entrepreneur, political firebrand, and media personality notorious for his 11-day stint as the White House Communications Director during the Trump administration. The conversation dives deep into Scaramucci’s blue-collar childhood, his climb through Harvard Law and Wall Street, the founding (and selling) of his investment businesses, the birth of the SALT Conference, his rise and fall in politics, and the core philosophies that have shaped his resilient career. Aspiring founders will find potent, unvarnished advice throughout: focus on hustle, integrity, adaptability, and learning from failures without being defined by them.

Key Topics & Insights

1. Scaramucci’s Superhero Obsession and Childhood Roots

Time: 02:05–05:15

• Superman & Identity: The episode opens with Scaramucci’s love of Superman—a symbol of the aspirational American dream and morality.
  • “Superman is who we want to be. But Batman, Batman is who we are... we got lightness and darkness.” — Anthony Scaramucci (03:30)
• Long Island Upbringing: Grew up in a hard-working, blue-collar Italian American family. Financial anxiety and his father's work ethic shaped his drive.
• First Hustle at Age 11:
  • Paper route that grew from 15 to the largest in his town: “I got the hustle in me very, very early…” (07:04)
  • Gave most of his earnings to his parents, supporting both the family and his own goals.
• Self-Confidence Through Hustle:
  • Key lesson: “You have to believe you can do something, and then you have to put a foot forward with imperfection. If you’re waiting for your business plan to be perfect... you’re waiting too long. You gotta get your ass going.” (09:57)
  • Cites the importance of building confidence and adapting through setbacks.

2. Nature, Nurture, and Developing Talent

Time: 11:17–13:33

• Scaramucci attributes his sales skills to both an “operating system” (emotional intelligence) and being raised right.
• Importance of self-awareness: “If you're self-aware, then you have the self-confidence to delegate.” (12:23)
• Early wins foster confidence; persistence is essential: “Every time I get a no, there’s gotta be a yes around the corner.” (13:37)
• The “cocktail party test”—Can you be the struggling entrepreneur among high-status peers and still carry yourself with pride?

3. From Goldman Sachs to Entrepreneurship

Time: 19:38–29:19

• Education and Class Mobility:
  • Went to Tufts (Economics major, Classics minor), then Harvard Law.
  • Shares a poignant story about his father cashing out his life insurance to pay tuition, a moment that underscored responsibility and gratitude. (21:24)
• Transition to Wall Street:
  • Joined Goldman Sachs, left to start his own firm after paying off loans.
  • Learned to adapt from being a fish out of water: dress, mannerisms, and operating as a “comfortable outsider.” (25:31)
  • “Are you a comfortable or uncomfortable outsider? If you’re a comfortable outsider, you can be comfortable with yourself and acknowledge your shortcomings in certain situations. I think it helps you.” (26:30)
• Mario Gabelli’s advice: Start your business before you turn 50—not just for status but for autonomy.

4. Building and Selling Businesses: The SkyBridge & SALT Stories

Time: 30:38–36:08

• Oscar Capital→Sale to Neuberger Berman:
  • Timing around 9/11 and strategic use of stock options in dealmaking.
• Founding SkyBridge (2005):
  • Seed money from Lehman Brothers, Merrill Lynch, Michael Dell ($25M) and self; started as a hedge fund seeding outfit.
• Seizing Opportunity During Crisis (2008):
  • Acquired Citibank’s fund of funds amid the financial crisis, with funding from Australian investors.
  • Created the SALT Conference as an “accidental” but now globally significant business move to drive engagement during tough times.

5. Philosophy of Networking & Relationship Building

Time: 36:08–39:29

• Authenticity is the key, not transactional relationships:
  • “I want to have nonlinear relationships with people, meaning I don’t want to be a transactionalist.” (36:54)
• Leveraging favors: “If you want to make a friend, ask a person for a favor.” (37:28)
• Vulnerability, openness, and resilience against rejection are essential to building social capital.

6. Delegation, Empowerment, & Leading Teams

Time: 39:29–45:14

• Give Away Power to Gain Power:
  • “If you want power, if you want to gain power and increase your power, you have to give it away.” (39:30)
  • Delegates significant autonomy to trusted team members.
  • Takes accountability for mistakes; encourages others by serving them (“servant leadership”).
• Hiring Strategy:
  • Trains generations of talent with a robust summer internship program, prefers to promote from within.
  • “Pay it forward” ethos; meets more people than necessary because opportunity can be anywhere.

7. The Highs and Lows: White House & Public Scrutiny

Time: 49:34–63:00

• Saw politics as a strategic way to network when golf and tennis weren’t options.
• Became a Republican by family tradition, entered the political fundraising pool.
• Story of being drawn into Trump’s orbit and the White House:
  • “I put my pride and I put my ego into my decision making… I’ve got to aggrandize my ego and my pride and all this silly stuff. And so I go to work for him. My wife said… you’re antithetical to him, you don’t think the same way... you’re going to have a hard time.” (52:08)
• Fired after 11 days; learned hard lessons about pride, ego, and public perception.
• Did not let one setback define him: returned to media, rebuilt his narrative, and found humor in public bashing (e.g., “SS Mooch” bobblehead, 16:12).

8. Frameworks for Resilience and Advice to Founders

Time: 63:00–68:06

• Don’t dwell on regret:
  • “When shit goes down and you don’t like it… forgive yourself, okay? Don’t carry the millstone of regret.” (57:16)
• Take pride and ego out of decisions; focus on fundamentals, like personal financial security.
• Don’t play the victim; accept outcomes and move forward:
  • “The world is based on is and was, not should and ought.” (63:24)
  • Ancient Greek masks: Expect both comedy (joy) and tragedy as part of the package.
• On handling criticism and public negativity:
  • “Get up. The number one thing is no self-pity.” (63:24)
  • “Grow a set of balls and shut the fuck up… Learn not to give a shit.” — Donald Trump’s advice, as shared by Scaramucci (60:00)
• Single Greatest Advice:
  • Read for three hours a day (“you’ll be more interesting, you’ll be smarter, and you’ll be ahead of the game because most people are not doing that”). (66:17)

Notable Quotes & Memorable Moments

• “Superman is who we want to be, but Batman is who we are.” — Anthony Scaramucci (03:30)
• "If you have integrity, you will always have opportunity." — Anthony Scaramucci (10:58)
• "Every time I get a no, there's gotta be a yes around the corner." — Anthony Scaramucci (13:33)
• “If you want power, you have to give it away.” — Anthony Scaramucci (39:29)
• “Mario Gabelli told me: in 10 minutes, you’ll be 50. If you want autonomy...start your business now.” — Anthony Scaramucci (27:06)
• “When shit goes down and you don’t like it…forgive yourself, okay? Don’t carry the millstone of regret.” — Anthony Scaramucci (57:17)
• “The world is based on is and was, not should and ought.” — Anthony Scaramucci (63:24)
• “Read for three hours a day.” — Anthony Scaramucci (66:17)
• On handling criticism:
  • “Shit written about me every day. Do you think I give a shit? Learn not to give a shit.” — Donald Trump, as told by Scaramucci (60:00)

Timestamps for Key Segments

• 02:05 – The myth of Superman and personal branding
• 05:17 – Scaramucci’s childhood hustle and financial anxieties
• 13:33 – Building self-confidence from early wins and losses
• 19:57 – Harvard Law origins and navigating elite spaces
• 25:31 – From Goldman Sachs to founding the first business
• 30:56 – The Oscar Capital story, sale, and founding SkyBridge
• 36:08 – Relationship building philosophy, non-linear connections
• 39:29 – On delegation and “servant leadership”
• 49:58 – Entering politics: maneuvering, motives, and the White House
• 52:08 – The cautionary tale of pride, ego, and Trump
• 57:16 – Lessons from failure: regret, adaptation, moving forward
• 63:24 – Resilience, accepting both comedy and tragedy
• 66:17 – Top advice: read for three hours daily

Conclusion

This episode is a masterclass in entrepreneurial resilience, grounded optimism, and straight-talk on navigating business, politics, and public failure. Scaramucci’s journey typifies relentless adaptation, building authentic networks, empowering teams, and above all, maintaining integrity. For first-time founders—and any ambitious listener—the lessons here are clear: Start before you’re ready, accept and adapt through struggle, invest in relationships, lead with service, and never stop learning.