How failure helps you succeed

Summary

Lost Boys Podcast Episode Summary

Title: How Failure Helps You Succeed
Hosts: Anthony Scaramucci and Professor Scott Galloway
Release Date: July 3, 2025
Website: www.lostboys.men

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Introduction

In the episode titled "How Failure Helps You Succeed," hosts Anthony Scaramucci and Professor Scott Galloway delve into the personal struggles and failures that have shaped their paths to success. Unlike typical discussions laden with statistics or expert opinions, this episode is a candid exploration of their own experiences growing up, facing adversity, and learning resilience. The conversation aims to provide a relatable playbook for young men navigating similar challenges in America today.

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Personal Stories of Failure

Anthony’s Journey

Anthony opens up about his tumultuous upbringing and the lack of a strong male role model in his life. Reflecting on his father's struggles, Anthony shares:

“At 12 years old, I remember this like it was yesterday because my mother still lives in the house I grew up with... He came home violent because he is completely out of control of his financial circumstances...”
[07:18]

This early exposure to financial instability and domestic violence instilled a deep sense of anxiety in Anthony, fueling his drive to achieve economic security. He recounts various jobs he held to support his family during his youth:

“Got myself a paper route, worked in a motorcycle shop, worked as a stock boy in the grocery store, worked on a stone dock when I was in law school during the summer.”
[12:04]

Despite these challenges, Anthony emphasizes the importance of perseverance through failures, sharing pivotal moments that tested his resilience.

Scott’s Struggles

Professor Scott Galloway mirrors Anthony’s sentiments by sharing his lowest moments, particularly his experience during his mother's battle with cancer:

“When I look back... that was one of them where I felt very, you know, I wasn't living up to my obligation as a man. It was humiliating.”
[04:56]

Scott speaks candidly about the emotional turmoil and feelings of emasculation he faced while trying to care for his ailing mother with limited financial resources. This period was a catalyst for his later achievements, highlighting how personal failure can drive one toward success.

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Lessons Learned from Failure

Both hosts agree that failure is an integral part of the journey to success. Scott succinctly encapsulates his philosophy:

“My success can be distilled to one word: failure. And that is my willingness to endure failure.”
[09:03]

He recounts his entrepreneurial ventures, having started nine companies with two successes, underscoring the significance of persistence:

“One out of seven companies succeed so I started nine and guess what? I've had two wins.”
[09:10]

Anthony adds to this by sharing his own setbacks, including his tenure at Goldman Sachs:

“I got fired from Goldman Sachs... I never fit in there. Nice people, smart people. But I didn't fit in.”
[11:48]

These admissions highlight that failure is not only inevitable but also a powerful motivator for personal and professional growth.

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Resilience and Overcoming Challenges

The conversation delves into the concept of resilience, emphasizing the necessity of enduring and learning from failure. Anthony reflects on the emotional impact of his failures:

“I felt like there was a ghost following me and my mom around saying, you're not worthy. You're just not worthy. You fucked up your mom up.”
[06:30]

Scott echoes the importance of mental and economic stability as foundations for resilience:

“You fix your own oxygen mask before trying to affix someone else's.”
[15:04]

This metaphor underscores the need for individuals to first stabilize their own lives before they can effectively support others.

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Strategies to Support Young Men

Moving beyond personal narratives, Anthony and Scott discuss actionable steps to aid young men facing similar struggles:

1. Modernizing Masculinity: Scott suggests redefining masculinity to include emotional strength and community involvement:

   “A more modern, aspirational vision of masculinity... the ultimate expression of masculinity, is to plant the trees, the shade of which you'll never sit under.”
   [16:04]

2. Building Resilience through Failure: Encouraging young men to embrace failure as a stepping stone to success is a recurring theme. Both hosts advocate for a cultural shift that normalizes setbacks as part of the growth process.

3. Creating Support Systems: Anthony highlights the impact of mentorship and positive role models in fostering resilience:

   “If you're doing well, you got to pull them with you.”
   [16:04]

   He emphasizes the role of peers and mentors in providing guidance and encouragement.

4. Access to Mental Health Resources: Addressing mental health openly and ensuring that young men have access to resources is crucial. Both hosts stress the importance of creating environments where seeking help is normalized and supported.

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Conclusion

Anthony Scaramucci and Professor Scott Galloway conclude the episode by reiterating the power of resilience and the transformative role of failure in achieving success. They call for a cultural movement that redefines masculinity, fosters community support, and empowers young men to navigate their struggles with strength and perseverance. By sharing their personal journeys, they aim to inspire and equip the next generation of men to overcome adversity and thrive.

For more insights and resources on supporting young men, visit www.lostboys.men.

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Notable Quotes with Timestamps:

• Anthony on Financial Struggles:
  “At 12 years old, I remember this like it was yesterday…”
  [07:18]

• Scott on Resilience Through Failure:
  “My success can be distilled to one word: failure.”
  [09:03]

• Anthony on Emotional Impact of Failure:
  “I felt like there was a ghost following me…”
  [06:30]

• Scott on Redefining Masculinity:
  “The ultimate expression of masculinity, is to plant the trees…”
  [16:04]

---

This episode of "Lost Boys" offers a profound and heartfelt examination of how personal failures can lead to significant personal growth and success. By sharing their vulnerabilities, Anthony and Scott provide valuable lessons and hope for young men striving to find their footing in today’s challenging landscape.

Transcript

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If you went on a road trip and you didn't stop for a Big Mac or drop a crispy fry between the car seats or use your McDonald's bag as a placemat, then that wasn't a road trip. It was just a really long drive at participating McDonald's. Welcome to this bonus episode of our podcast, Lost Boys, where my friend Professor Scott Galloway and I talk about how a generation of young men is falling behind and what we can do about it. In this bonus episode, we're not talking to any experts or quoting any statistics, but when we were talking, we both wound up discussing our own experiences growing up, the challenges we faced, our lowest moments and our failures, and most important, what we learned from those failures. Here's my conversation with my friend Scott Galloway. I think one of the things that's joined you and me in a number of different ways. I always remark to people how people bring your name up. I say, well, for whatever reason, I feel very close to Scott because we sort of, sort of grew up similarly on different coats. And we have these trials and tribulations, this sort of odyssey to get to where we are. And we have a lot of empathy in that thing. You know, I feel like you've seen the whole spectrum, Scott, in terms of the income strata. You've seen your mother struggle and now you sit here with a couple of houses and some financial independence. And so you're able to look through everybody in a way that sometimes when I'M talking to my rich friends again. I'm just being brutally honest. I feel like, wow, they're so sheltered, they don't see it. And if I'm talking to my poor friends again, being brutally honest, I'm like, wow, you don't realize that the rich people have problems too. You know, I'm in the Big Brother program. My big brother, my little brother is 43 today. And I'll just tell you this quick story. So I met him at 13. I helped him get through school. I paid for his Catholic education. He's an African American kid, fatherless, mother raised him, a couple of siblings. And my brother had a drug addiction issue. And I can remember the look on his face. He must have been 16 when I said, I can't meet with you. I'm taking my brother to drug rehab. And he was like, wait, what? White people living in like an upper middle class area, they have these problems too, you know, I think people fail to understand. And this is one of your great gifts, by the way. And again, this is not inflation, praise or whatever Richard said, but this is truly one of your great gifts. You see the whole continuum and you recognize, yeah, it may be easier or more convenient to be wealthy, but people are in a struggle no matter where they are on the income strata. And so I guess when you speak about this, what's the reaction you get? Like when you give a TED Talk on this, what's the reaction you get?

[B]

People are, for the most part generally very supportive, especially lately, because this afterburner effect of mothers weighing in is really, really positive. And it's gotten more and more positive. And people are exceptionally, I find exceptionally supportive. You asked me a question earlier that I was caught off guard and I didn't answer. So I'm going to answer it and then I want to turn it back to you. You asked me what was my lowest moment. And first off, I know you grew up in financially strained circumstances. I affectionately say I was upper lower middle class. My mother lived and died as secretary. Our household income was never above 40,000 for most of my childhood. It was probably somewhere between 10 and 15 grand. I got Pell Grants. And when people meet me, they don't assume I had a single mother and was got here on Pell Grants. They just don't. They look at me, they're like, oh, there's this white dude who probably went to Eaton or whatever.

[A]

Refined guy, refined.

[B]

And. But that's just. And it's, you know, stereotypes can work always. Right. My lowest moment, if I had to Identify. When I was in graduate school, my mom had been diagnosed with cancer for the second time. She went into the hospital to get a mastectomy. They discharged her early. We were underinsured. She was at home, she'd started her chemo. She called me at graduate school, I was at Berkeley and said, I need you to come home. I am not doing well. And I flew home. And my mom's not dramatic. I flew home. And I'm telling you, Anthony, I walked into the most frightening situation for a 25 year old man. And there's just certain things I can't do for my mom. And my mom was so incredibly ill that she just couldn't move and was throwing up. I mean, it was just, it was a dark, ugly situation that I did not know how to handle. And so I started calling around to try and find a nurse. And nurses were 35 bucks an hour. And I had $400 in my checking account. And I thought, okay, I can afford a nurse for 12 hours. And I remember feeling so emasculated, right? You're a dude. You're the only person important in your life who's just loved you. Irrationally, you can't be the man, right? That was awful. And quite frankly, it was very motivating because I, like a lot of men, got my act together later in life. And I thought, you know, you can't decide to be economically secure, but you can decide to do everything within your power. And that's when I decided, look, I need to get my act together because I do not want. And it also struck me about the American healthcare system, about how rough things can be. I don't think people really understand, and I know you do, what it's like to be economically strained. And maybe you're an empathetic, good person, but if you didn't grow up, if you grew up with money, you'll just never understand. I felt like there was a ghost following me and my mom around saying, you're not worthy. You're just not worthy. You fucked up your mom up. You're not worthy. So that, that for me, when I look back on like, like terrifying moments, that was one of them where I felt very, you know, I wasn't living up to my obligation as a man. It was humiliating.

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[B]

All right, your term.

[A]

Lowest moment I'm going to tell you but it's one follow up question though. The resilience factor in your personality though, so never so low where you were like suicide ideation or anything like that, right?

[B]

No, my look, my success can be distilled to one word failure and that is my willingness to endure failure. Yeah, one out of seven companies succeed so I started nine and guess what? I've had two wins. But you know what? That's all you need. Yeah, I can't tell you how much rejection I ran for. Sophomore, junior, senior class president, lost all three times. Based on that decided to run for student body president where I went on to get this lose. But I was never afraid to keep trying. I know you've had some hits. Christ, you're in crypto forgotten.

[A]

I'm going to give you the big three for me. I'm going to give you the big three. My dad got his hours cut. I was 12 years old. I remember this like it was yesterday because my mother still lives in the house I grew up with. He came home and I'm just going to be brutally honest on this podcast Violent and I today I feel bad for him. At 12 I was scared for my mother and myself and my siblings. He came home violent because he is completely out of control of his financial circumstance. Meaning his foreman cut his hours back. He was an hourly worker, and that meant there was going to be less money in the house, you know, and, you know, he could have, I guess, got a job at night to stock shelves. But that job of operating that crane was a tiresome job, Scott. So I remember that anxiety like it was yesterday, and I think it still fuels me today. So 12 plus 49 is 61, I guess, right? That's where I am right now. 49 years of that anxiety. Got myself a paper route, worked in a motorcycle shop, worked as a stock boy in the grocery store, worked on a stone dock when I was in law school during the summer. And just because of that anxiety. But the three big failures for me were I failed differential calculus in high school. I got a failing grade in differential calculus. And I was like, okay, that's it. I'm not going to be able to get into college. And lo and behold, I went to see my guidance counselor, and he said, okay, you can take a summer course. And thank God they did this, Scott. They erased the failing grade and they replaced it with the grade that I got in the summer course. But I remember I was completely anxious about that. I got fired from Goldman Sachs. I think I told you the story once at lunch. I got hired at Goldman Sachs on August 14, 1989. Fired February 1, 1991. I was only there for 18 months. And, you know, they were having a. They were having a slowdown and they were cutting people in the department, and I wasn't up to measure, I guess, and they fired me. And I had no money, Scott. I was married, my wife was pregnant, and I had school debt, and I had anxiety through the roof. I eventually got rehired into Goldman, so it didn't look like I got fired, but I got fired. I actually got to keep the $11,000 severance check, which is a whole other fun story. But anyway. And I never fit in there. I never fit in at Goldman. I'm just be brutally honest with you. Nice people, smart people. But I didn't fit in. I had to go start my own business. And then, of course, I've had the White House firing. I've had my up and downs in the crypto space. But you want to talk about low moments like you, which is why I have such identification with you. When you're getting your butt kicked at age 25, you got to know where to go, man. There's no Uncle Galloway or Uncle Scaramucci. Hey.

[B]

Hello.

[A]

Can I help you. You know, like when I was having career issues, I couldn't call my dad, my dad, I mean, and no offense to him, but he couldn't supply me with a white collar strategy for my white collar job. And so this is the reason why I'm sitting here with you today. And I'm saying, okay, listen, there's a group of people out there that need this help. You know, the educational system's fractured. You got there, I got there. We're the product of good mentoring, good education, self will and resilience and like you said, failure. And being able to fail more times frankly than other people are willing to fail because you'll eventually get to the success. But I'm just wondering if their kids. I'd love to, one night I'll introduce you to my 43 year old little brother. He's got three beautiful kids, he's on a security detail at Hudson Yards. And he would say to you what I'm saying, and Richard's saying, and what you're saying, you showed me the way. I looked up and said, hey, this guy's working his ass off. I'm going to go work my ass off. Yeah, I don't have a good role model. My father left my mom. I don't even know who he is. But this guy's working his ass off. And it's what you do, Scott, more than what you say when you're around those people. Do you understand what I'm saying 100%. And I'm just wondering, at this stage in your, my life, is there something that we could do? Take our creativity, our minds, take the culture, dent the culture, you know, how do we dent the culture to get it back to, it's okay to be a young male, it's okay to provide advocacy for yourself and feel advocated for. And oh, by the way, if you feel like shit or you're lonely or you're experiencing suicide ideation, which has got to be the worst possible thing on this planet, frankly. How do you, you know, can you, can you get help? Can somebody lift you up and pull you back into the game, make you feel loved, wanted, needed and purposeful?

[B]

Yeah, I like that. I think of it as concentric circles. At the very beginning, you got to take care of yourself. You got to be strong, you got to be economically viable, you got to be mentally fit. You fix your own oxygen mass before trying to affix someone else's. You gotta, you gotta get your own shit together. Once you're together, you can take care of your Family. I mean, you gave me a ride home. Our driver is your cousin.

[A]

Yeah.

[B]

I mean, I got the sense that you're literally Scaramucci, Inc. And you employ 80% of this big 80% of Manhasset or whatever it is you live.

[A]

I mean, I got him out of clamming. He's making four times his salary with healthcare benefits. And Skypridge is paying for ivf. Okay. To help him create a family. Or he could be on a boat. Right. You know my point? But, you know, when you grow up like I did, you got people around you. If you're doing well, you got to pull them with you. I'm just wondering if there's a national movement that we could do that's similar to what you just said.

[B]

Well, I think it comes back to trying to come up with a more modern, aspirational vision of masculinity, and it's, you take care of yourself, you get strong, you get fit, you get economically viable, you take care of your family. Then if you're really strong, you start taking care of your community and your neighbors, and then you start getting involved in the lives of maybe of a kid that's not yours. And then the ultimate ball or move, the ultimate expression of masculinity, is to plant the trees, the shade of which you'll never sit under.

[A]

Thanks for joining us for this episode of Lost Boys. If you'd like more information, go to our website, www.lostboys.men. be sure to, like, follow and subscribe to Lost Boys wherever you get your podcasts. And please share it with someone who cares about this or should care about this. And let's spread the word. Lost Boys is a production of Salt Media and the Casablanca Strategy Group. Barbara Fedita and Keith Summa are executive producers. Tanya Salotti is our researcher. Holly Duncan Quinn and Stanley Goldberg our editors. Special thanks to Christina Kasese, Mary Jan Rebos, and Drew Burrows.