Episode 18: Anthony Scaramucci - Managing Partner of SkyBridge Capital

0:00This week, I had a chance to sit down with none other than Anthony Scaramucci, a dynamic force in finance, politics, and media. Best known as the founder and managing partner of Skybridge Capital, which has managed up to$10 billion in assets, Anthony has built a reputation as a bold thinker, resilient entrepreneur, and an outspoken voice on Wall Street and beyond. From growing up on Long Island to rising through the ranks at Goldman Sachs, launching Skybridge and navigating the stormy waters of public life, including his headline-making 11-day stint as White House Communications Director, Anthony's story is one of reinvention, grit, and relentless drive.

0:37He's authored several books on investing and leadership, and through his SALT conferences, he's created a global platform for dialogue across finance, tech, and policy. In this conversation, we unpack his formative years, his evolving relationship with failure, and how his identity as an outsider has shaped his approach to both business and life. We also dive into the people who have impressed him most, what's next on his horizon, and his best advice for the younger generation. I enjoyed this conversation, and I hope you guys do too. Thank you for joining me, Anthony. I really appreciate it. Thanks for coming on.

1:10It's good to be here. I appreciate it, Amir. All right, fire away. So I want to go back to your upbringing, your childhood. How do you think your childhood and talk me through some experiences in it that you think shaped the person you are today?

1:29Well, I mean, I don't want to glorify it, right? I mean, because as happens, you end up with some modicum of success and then you want to go back and hagiographically look at your childhood and sort of glorify it. I would say to you that I was anxious as a child. If I'm really being brutally honest, there was a financial dilemma always in the house. There was constant financial anxiety. My father was a hard worker, but he was limited by his skillset. He started out as a laborer, They became a crane operator. Then he got older, became a dispatcher. And these were all hourly jobs, all tied to a union.

2:06And so when economic expansion was happening, he had lots of overtime that was better for the family. when we were going through recessions, like what happened in the 1970s. It was very painful for the family. And so, you know, I had a great childhood too, though, meaning, you know, I lived in a great middle-class neighborhood. I went to a great public school. I had really good teachers. I had a great sports program that I benefited from as a kid. And so, you know, I had a nice childhood. I'm not trying to say that I didn't have a nice childhood, but I had financial anxiety. You know, I can remember there'd be fights in our home growing up related to money.

2:45And so that got me to be, I think that turned the screw on me or coiled the spring on me to get out and get to work. And I started working when I was 11, I got a paper route and then I built that paper route into a pretty colossal paper route in the town. I had this idea that I went to my manager. I said, look, I need free papers on Wednesdays. Thursdays was what we call collect. You would knock on the doors of these middle-aged women. He'd ask them for money for the subscriptions of the newspaper, Long Island Newsday. And so I got free papers. I went up and down the apartment buildings in the town I was in dropping off free papers for all these Irish and Italian women.

3:25And then on Thursday, I would knock on the door and say, hey, you know, Mrs. O 'Callaghan, did you like the paper? Would you like to subscribe to it? You know, I guilted them all into it, right? And so I had a a pretty decent paper route. I probably had 40 or$50 a week coming in at the age of 12. And I used to split that with my mom, try to help her out, you know, with the family's budget. And then I ended up as a stock boy at the local key food. If you, if you heard cleanup on aisle seven, that was me. I would go and mop up the dill pickles or, you know, I was, don't eat a rotisserie chicken.

3:59I mean, you want to talk about my childhood? I cooked rotisserie chickens at the local supermarket with the apron and the hat and everything. I had the syringe. I put the mixture into the, you know, basting the chickens. And, you know, I guess a cautionary tale from my childhood, I don't recommend you buy a rotisserie cooked chicken from the local supermarket because you just put too much salt and sugar and chicken broth into those things. They taste great, but I mean, your eyeballs will be bulging out of your head from the dehydration. So that's another lesson for my childhood. But I worked in a motorcycle shop.

4:34I delivered and sold mopeds. I learned how to drive when I was 14. I crashed the car when I was 15. You know, it was a rough and tumble upbringing. My parents were not focused on education. So I'm sort of a big and elementally there. If you looked at my cousins, my brother went to college. He was the only one. There's 16 or 17 of my cousins. Very few went to college. So my upbringing was, I think, good, but it was anxious. I was definitely worried about my parents. I was worried that my parents were going to run out of money. I chose my career not out of love. I do love what I do, Amir, but I chose my career out of financial anxiety.

5:19I figured if I went to work on Wall Street and I was halfway successful, that would solve a lot of my financial problems. Yeah. and I read a couple articles where you talk about Superman and Batman, and I'd love for you to kind of briefly describe those and elaborate on both of those figures. But what I'd also like you to do is talk a little bit about who your heroes were, both as a child and now, and what do you think that says about yourself and the people you look up to?

5:48Okay, you know, I'm going to stay away from saying that my parents are my heroes or my grandparents. I'll talk about mentors. There was a there was a guidance counselor by the name of John Zanetti. He's the one that told my parents to send me to Tufts, not the local state school. There was Saul Gittleman. He's 91 years old. He was the provost at Tufts University. He took me under his wing, helped me get into Harvard Law School. Tough love from him when I was not doing certain things well. He hit me over the head hard, told me to get my shit together. So I always have an admiration for him. I guess, you know, when you talk about literary role models, you know, I would say to people that if you read the Iliad of the Odyssey and you read Marcus Aurelius' Meditations and you read one Shakespearean play, you would be ahead of just about everybody else in terms of understanding how human beings interact with each other and what the elements are and what the triggers are for the social animal that lives on this earth known as a human.

6:52And so I would say that those are intellectual role models. On the investment side, I probably devoured everything that Warren Buffett had ever written. I'd like to say that I followed him, but it was hard to follow him because I always had, you know, if I had held things longer in my portfolio, I would have done better, frankly. I think that's the lesson from Buffett. But, you know, I needed money for a house or I needed money for my kids' tuition or I needed money for different things. I would have just been better just holding on to the assets, probably even borrowing against them. But that's somebody that I look up to and admire.

7:27When you talk about the comic books, the comic books, when I was a kid feeling that anxiety, that was a form of escapism for me. So on Wednesdays, the new comics came out. I got my money on Thursdays. I used to save my money, have to wait till the following week. the new comics of Superman or the Batman came out on a Wednesday at the local stationery store. And I have a big collection of comic books. You know, I've got some golden age, silver age comics, comics from the 1970s when I grew up. And what I tell people, you know, Superman was an interesting, iconic mythological American mythology. It was invented by two young Jews, Jewish men, Jewish boys in Cleveland, Ohio.

8:10It was a direct response to what Adolf Hitler was saying about the Übermensch, the overman, the man that Nietzsche described as being more powerful than others, part of this German iconic culturalism. And obviously the Jews were inferior and the Aryans were superior. And so these two young, brilliant Jewish men, Joel Siegel and Jerry Schuster, they invented superman uh it was an american version of this uber mensch and uh but they they instilled in this character american mythology of course it's a loner uh uh outsider an immigrant right strange visitor from a foreign planet has to be adopted by a virtuous american family of course it's a midwestern family that has classic hometown midwestern values And then it's a journey, a hero's arc story where the young boy with the superpowers is trained by his kids, trained by his school, trained by the mores of his time to be a good person, goes into the city to find his career.

9:17And he stands for truth, justice in the American way. And he's good hearted. He's aspirational. He's who we want to be. Superman is a representation of how we'd like to see ourselves. I always say that Batman is actually who we are. You know, Batman's dark. He's got good things about him and bad things about him. He's always fighting demons in his own mind. Yes, he's fighting crime, but he's able to fight the crime because he thinks like a criminal. You know, and he's got these dark parts of his personality. And so to really understand human beings, we're light and dark. We have the capacity to kill each other.

9:52We have the capacity to love each other and take care of each other. and we have to possess ourselves with the right thoughts and possess ourselves with the right ideas so that we take care of each other. We're at our best when we're serving each other. We're at our worst when we're taking from people without recompense. And so for me, those are sort of iconic models and mental models that I try to think about. I tell people that work here at Skybridge, We have a couple billion dollars under management. They work with me. They don't work for me. This is a collaboration. It's not a, I feel like you get more out of people if they're rowing the boat with you and they feel like they're in it with you as opposed to, you know, this sort of command control structure or this over bossing or over bullying.

10:45It's one of the reasons why I couldn't really get on with Trump inside the White House. I'm not a student of or a fan of that type of behavior. you've failed many times throughout your career and you're very truthful, transparent, and honest about your failure and coming back from that. I think there was an article that was written a couple of months ago called the immortal Anthony Scaramucci. And I think that's a very good way of describing you, but I'd love for you to take us through your career from a high level, but focus on the role that failure played in your career and how you came back from that.

11:18Because I've noticed in your career, every time you fail, you come back stronger. Well, the first thing I would say is it's a fun title, Immortal, but I think that the first thing we ought to recognize is our mortality. I think that we're at our best, again, when we are real with ourselves. You know, we have a tendency to lie to ourselves. You know, we live in some level of denialism. We don't like to think of ourselves dying. We get up in the morning and say, okay, we're going to keep going, so therefore it sustains us. The other person is going to die. You know, the, you know, the famous thing when you're in the platoon boat, the guy on your left and the guy on your right is going to die.

11:55I mean, one of them is you, you know, but you don't think that. And so, but we are mortal. And I think, I think when we face our mortality, like Marcus Aurelius said, momento more, in this moment I can die. I think it can be therapeutic for people. I think it can, I think it can force a perspective. And so I would say to you that I'm very mortal, but I'm also very aware of my mortality. So I want to go out with a good blast here. I want to help people grow a business, live with some level of purpose, give away some money to charity, but also charity starts at the home, take care of my family members and my extended family members, take care of the people that work here in the organization with me.

12:39I think that's really what it's about. I think you get your highest joy, highest level of psychic happiness when you're integrated with others. This is a social organism. There's a hive to being a human. And when you're working with the hive and making the hive better, more successful, you're better. When you're too cynical or too despairing or too pessimistic, I think you can make things worse. And I also think that your attitude is everything in life. And I got fired from the White House. I got humiliated eight years ago. I got lit up on late night television. Videos play to me. I was told, I think Steve Colbert said I was Tony Soprano on the Potomac, and Bill Maher said I was a Jersey Shore cast member.

13:26And you could, I mean, I'm just scratching the surface of some of the stuff that I had to hear. And you could take that and be saddened by it, and you could be remorseful, and you could dig a hole for yourself and hide in it. Or you can take yourself less seriously and laugh about it. And when I got invited on those shows, I went on. It was a good sport. I didn't pretend that the stuff didn't happen to me and I didn't try to run from it. I went towards it, not away from it. You know? Yeah. And how do you think your relationship with failure has evolved through your career? Because the earliest point in your career in which I think you can describe you failed is when you got almost got fired from Goldman.

14:11Not almost. No, I was fired. No, I get fired. I got fired on February 1st of 1991. I got rehired on March 28th. But on February 1st, it was a Friday night. The senior partner in the real estate department let me go. And they gave me a severance check. And they told me that there was no room for me left at the firm. I had to go find a job. And, you know, I mean, that was a big blow to me. I had gone to Goldman. I was 18 months into the job. I showed up every day, worked hard. Frankly, I sucked at the job, but I was trying. They were going through a real estate recession, and they made a decision to let people go.

14:47I was one of those people. I was ill-fitted for that job. And so the learning lesson for younger people is don't take the job that you think is cool or don't take the job that you're taking to try to impress your friends. Take the job that you think you're going to be good at or that you like. I took the wrong job. It was real estate investment banking. Terrible job for me. So they fired me. And I sucked at the jobs. So no harm, no foul there. I got lucky where Goldman was hiring in another area of the firm. And so I got rehired into Goldman. That was a good experience for me. But again, I would say this to you, that was lucky too.

15:26And I got into a good job that I liked. And so again, there's some things that are going to happen in your life that are circumstantial. There's some things that are going to break in a way that are very lucky for you. There's some things that are breaking away that are not lucky. You know, you're going to take the wrong job at the wrong time. I think you have to flow with it. You know, when I got fired, I made a joke that next day they let me stay in the office for a week to get my stuff together and start to begin a transition. And the Gulf War was going on at the time. And I said, it's too bad I didn't have any Patriot missiles to block the incoming scud that hit me.

16:02And people laughed. It made them feel better because I wasn't trying to make them feel bad about my firing. You know, I was trying to roll with it. and what I would say to you in life is that that's it. That's the secret, you know, expect that, you know, look here, how old are you even, why am I asking? I'm 15. 15. Okay. So if I took out a sheet of paper, the day you were born, so you were born in the year 2010? 2009, August 18th. 2009. All right. So I took, I took a sheet of paper out. Let's say you could read the first day you were born. I said, okay, here's the piece of paper. Here are your parents.

16:37You didn't pick them. You didn't pick your location of your birth. You didn't pick your skin color. You didn't pick your nationality or your religious background. And so here's your life. And by the way, guaranteed, you're going to have some disappointment in your life. You're going to have a girl break up with you or a setback. You're going to have a setback in a business, setback in academics. You're going to have a great thing happen, a bad thing happen. Unfortunately, you're going to experience death. That's part of the human condition. So either be people that you love that die it'll be you yourself that die uh and so i guess the point i'm making is everybody comes in with that checklist everybody comes in with that punch card amir nobody escapes that yes you could be worth a hundred billion dollars you're still dealing with that bill gates said something maybe 25 or 30 years ago now i always think about it I said, I'm the richest person in the world.

17:33At that time, frankly, he was. His mother was dying of breast cancer. He couldn't save her. It's just unfortunately, there's a start and an end date. Thus far, God's batted 1 ,000, and we're all destined to die. And so we're going to live this trial and tribulation on earth. Accept it. Embrace it. People that can embrace it can ride through failures more easily than people that have these very high, unfair, very high and unfair expectations about life. You've constantly described yourself as an outsider. And my question to you is, how do you think your role as an outsider has changed both how you approach challenges and also move on from setbacks throughout your career?

18:24oh you know i'm an outsider in the filing respect you know i i didn't uh i didn't grow up in new york city i didn't grow up as a member of the establishment i didn't grow up in a rich family there's no legacies at any of the schools that i went to that i could say that i was a part of uh i didn't see the inside of a country club until i was in my early 30s i don't hit a golf ball or swing a tennis racket. And so I'm not really part of the artifice of what would be the establishment. I'm not saying that I'm Jay Gatsby or anything like that because there's nothing nefarious about it. I'm just not a insider.

19:01There are comfortable insiders and there are comfortable outsiders and there are uncomfortable insiders and there are uncomfortable outsiders. So Donald Trump to me is an uncomfortable outsider. He grew up wealthy, but he grew up in the outer boroughs. And so he never really got into the flow of the hoi polloi in Manhattan. And it always bothered him. There were several country clubs he couldn't get into, always bothered him. There are country clubs, frankly, a mirror that I couldn't get into. They'd probably want me to landscape the country club before they'd let me in as a member. But I'm comfortable with it.

19:34I don't care. It doesn't bother me. I'm comfortable in my own skin. You can reject my thought process. You can reject my analytical views. you may dislike or like my personality, but not want me to work in your organization. I'm cool with all that. I went and built my own organization. So I'd always have a job and I wouldn't have to worry about that, or I wouldn't have to worry about refining my personality to suit some type of corporation. And so I guess what I would say to you is if you're a comfortable outsider, you can take comfort in your outsider-ness. And what I mean by that is I don't care.

20:10You know, You can let me into the situation or keep me out of the situation. It doesn't bother me one way or another. I don't have a chip on my shoulder. And I think that can make you pretty resilient because what's important to me is what my family thinks of me. What's important to me is what my wife thinks of me and my children. And I don't really give a shit what you think of me. And I don't care what your listeners think of me. I'm going to tell them what I think. If they like me, that's great. If they want to have a relationship with me, I'm open to it. If they reject me and my thought process, that's okay, because I have in my heart where I want to go for myself.

20:45And so I think if you are comfortable in the way that I'm describing, you can take exogenous risk. You can flip your fund of funds into crypto because you see something that you want to exploit for yourself and your clients, and you're not thinking about the downside failure of that. You're thinking about the upside, and you're thinking about the benefit. I'm not measuring myself day to day by what other people think of me, and I'm not flexing myself in an effort to impress anybody. I think those things do make you very resilient if you have that embedded in your philosophy.

21:24And you were talking about flipping your fund to funds into crypto. And at this point in your career, many people would be complacent, but you keep trying new things. You've kept innovating and kept being creative. So my question to you is what makes you confident to try new things in venture into new spaces, even at this point in your career? You know, I'm a young guy. I mean, I'm 61 years young. I love the planet. Love my family. Love my employees and partners, people that work with me. And so I want to be productive. You know, I want to be useful and productive. A couple of years back, I had the opportunity to work out with Arnold Schwarzenegger at Gold's Gym.

22:05He's 78, 79 years old. He's hitting the gym and he's writing books. And one of the titles of his book is to be useful. So I want to be useful. You know, I'm here. I'm not going to go to the beach. I mean, I can spend two days on the beach, then I'm getting bored. And what am I going to do? I can write books, which I'm interested in doing. I can talk on podcasts. But what I really like doing is I like coming up with new ideas and I like helping people. And so why not do that? If that's something I really like to do. There's a friend of mine. He should probably interview him at some point. His name is David Rubenstein.

22:39He's the founder of Carlisle. I went to visit him many years ago. He has a beautiful house on the bluff in Nantucket. It's overlooking the Atlantic Ocean. It's absolutely breathtaking. You go to the front door, there's a sign on the house that says, rather be working. There's David Rubenstein letting you know, yeah, he's got money, and yeah, he has pleasurable and nice things, but it's not that big of a deal to him. What's a bigger deal to him is that he's working. He just bought the, he's probably 73 or 74 years old. He just bought the Baltimore Orioles. He grew up as a, in section, you know, eight housing and public housing, a poor guy that became extremely rich.

23:17And he's now trying to bring a championship to the city of Baltimore, a place that he grew up in. That's my kind of guy. That's the kind of person I'd like to be. If the good Lord blesses me with a long life, hopefully I'll be doing this for the next 20 to 30 years. And on the topic of David, I'm a big fan of his interviews. Who are the most impressive people you've ever met or people that have just fascinated?

23:48Well, I mean, you know, you can, yeah, I'm, I'm, I'm, I'm writing down the list. I mean, I'll give you the top three. I think that you would be remiss in not saying that Donald Trump is not impressive. I don't have a good relationship with him, but he is a prodigious political figure. He is the most important political figure of the first 25 years of the 21st century. He's cast a shadow over half of that period of time. And so for me, I would say that he's impressive. I don't like him. I don't like where he wants to take the country. but I mean, you know, I work closely with him and you have to be impressed with his political instincts and his insights.

24:28He's way smarter than people want to give him credit for. Elon Musk, another controversial figure, is just very ironic because if you and I did this interview in 2016 when the Model S came out, Elon, 71 % of our fellow Americans knew who he was and 70 % of those people had a favorable opinion of him. They saw him as this echo-friendly, Tony Stark-like technologist that was doing good things for mankind. Because he went into politics, 91 % of our fellow Americans know who he is, and only 33 % of them like him now. But it would be remiss of me to tell you that he's not singularly the most impressive person that I've met in terms of his work ethic, the way his brain works.

25:12He's a moneymaker. If he goes back to making money, he'll go on and probably be our first trillionaire. David Rubenstein is a person I have an enormous amount of respect for. I'm going to tell you something. My father-in-law, and again, I want to leave out my parents who I've obviously have an enormous amount of respect for, but my father-in-law, who's now deceased, he was a parking attendant. You couldn't have found a nicer person. You couldn't have found a better family person. You couldn't have found a kinder, more forgiving person who didn't judge human frailty so harshly. And he was a parking attendant.

25:48So it doesn't just have to be a rich person or a successful politician. It could be somebody in your backyard that you look at and you're like, wow, I got a lot of admiration for that person. And that person's a role model for me. My, my father-in-law in many ways was a role model for me. If you had to distill down the way you live life in. to a couple of tenants, what would it be? What kind of central tenants guide the way you live? Well, again, don't judge human beings so harshly. Don't judge human frailty with great harshness. Be forgiving. Be forgiving of yourself when you make a mistake. Be forgiving of others.