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The Learning Leader Show With Ryan Hawk

643: Anthony Scaramucci - Getting Fired by President Trump, Working With a Life Coach, Playing Quarterback, Building Confidence + Charisma, Telling The Truth, & Finding Your Superpower

The Learning Leader Show With Ryan Hawk

Ryan Hawk

Careers, Management, Business

4.81.3K Ratings

🗓️ 6 July 2025

⏱️ 55 minutes

🧾️ Download transcript

Summary

Go to www.LearningLeader.com for all show notes

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Go to www.InsightGlobal.com/LearningLeader

Anthony Scaramucci served as the White House Director of Communications for President Donald Trump from July 21 to July 31, 2017. He was at Harvard Law School with President Barack Obama and First Lady Michelle Obama. He’s the founder and managing partner of SkyBridge Capital. And he’s the founder and Chairman of the SALT conference. 

  • Leadership through service: True leadership isn't about personal glory but about making others better and helping them succeed in their roles. Derek Jeter exemplified this by never caring about personal statistics, only team success. "If you're on the team, it's not about me, right? It's about you. How am I gonna make you better? Or how am I gonna make you feel good about your role? How am I gonna get you to think that I'm here to help you?"

  • Flexibility and decision-making under pressure: Football taught Scaramucci the importance of reading situations quickly and making audibles at the line of scrimmage - skills that translate directly to business and life leadership. "You can't just say, okay, here's the game plan, right? Because that's what Mike Tyson says, right? You have the plan until you get punched in the face, or all battle plans go by the wayside with contact with the enemy."

  • Resilience through adversity: Getting "your ass kicked" early in life builds the resilience needed for future challenges in business and politics. Early defeats teach you how to bounce back from failure. "That's called resilience, right? You gotta get over that... That's how you gotta get your ass kicked. Here I was... and I just remember feeling so puny... So how you gotta get over that."

  • The confidence battle starts within: The first fight in life is with yourself - believing you're good enough and worthy to compete. Henry Ford's principle applies: "If you think you can or you can't, you are right." "The first fight is with yourself. Am I good enough? Am I worthy? Can I get to the game? Can I believe in myself enough so that I'm standing next to someone else who believes in themselves that I compete?"

  • Accountability in relationships: When Scaramucci's marriage was in crisis, taking full accountability for his mistakes rather than deflecting blame was crucial to rebuilding the relationship. "I owe my wife Deirdre, a debt of gratitude for actually really loving me because I was off the rails on a few things... she's like, Hey, I'm not having this, so if you love me, get your shit together."

  • Life coaching vs. therapy approach: Life coaching focuses on progression and future action ("What are we doing today to be better?") rather than regression into past issues. "I feel that therapy is a regression. Life coaching is a progression... forget about the past. What the hell are you gonna do? What are we doing today to make yourself a better person?"

  • Forgiveness as liberation: Choosing to forgive both others and yourself removes the "millstone of regret" that weighs you down and prevents forward progress. "I can take that millstone of regret and leave it behind me, take it off of my neck and leave it behind me... human frailty and not judging it is not just you judging others, but also yourself."

  • The comfortable outsider advantage: Being comfortable with your outsider status while still being able to operate in elite circles provides authentic confidence and relatability across all social levels. "I am a comfortable outsider. I'm not an insider... but I'm comfortable with it. You know, like guys like Trump or Rudy, they're uncomfortable. Outsiders... But I'm a comfortable outsider. I don't need to do that."

  • Intellectual curiosity + neuroplasticity: Combining genuine curiosity about others with the ability to adapt and change allows you to move successfully between different social and professional circles. "Find your superpower... I think your superpower is very similar to my superpower... intellectual curiosity. And so if you can blend intellectual curiosity with neuroplasticity, meaning you can adopt and change... then you can move in various circles."

Pivot for survival: Successful businesses and careers require constant reinvention. SkyBridge's conference business and pivot to Bitcoin were survival strategies that became major successes. "We were going outta business... This was an accidental survivor strategy. This was a pivot that we were making in order to stay in business. This was not some mastermind plan."

Transcript

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0:00.0

This episode is brought to you by Insight Global.

0:03.9

Insight Global is a staffing and professional services company dedicated to being the light to the world around them.

0:11.1

If you want to learn more about the CEO, Bert Bean and Chief Revenue Officer Sam Kaufman,

0:17.1

check out episode 424.

0:19.1

We had a fantastic conversation talking about my partnership with

0:24.8

the great people at Insight Global. If you need to hire one person, hire a team of people,

0:29.2

or transform your business through talent or technical services, Insight Global's team of 30,000

0:36.1

people around the world have the hustle and grit to deliver.

0:40.9

Hiring can be tough, but hiring the right person can be magic.

0:45.8

Visit Insightglobal.com slash learning leader today to learn more.

0:50.3

That's Insightglobal.com slash learning leader.

0:57.4

Welcome to the Learning Leader show. I am your host, Ryan Hawk. Thank you so much for being here.

1:05.4

Go to LearningLeader.com. For show notes of this and all podcast episodes, go to learningleader.com.

1:13.8

Now, on to the night's featured leader the mooch.

1:17.0

Anthony Scaramucci served as the White House director of communications for President

1:23.0

Trump from July 21st to July 31st, 2017.

1:28.1

Yes, 10 days.

1:29.1

He was at Harvard Law School with President Obama and First Lady Michelle Obama.

1:34.2

He's the founder and managing partner of Skybridge Capital,

1:37.2

and he's the founder and chairman of the Salt Conference.

1:40.9

He's done a lot.

1:41.4

During our conversation, we discussed what he learned from getting

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