How Anthony Scaramucci Became The Mooch | First Time Founders with Ed Elson

Hey, that means I'm very flattered to be on it. Thank you. I like the... I need swag. Okay, I need swag. Okay, first time founders. I want to wear a shirt, a hat.

Well, okay. So, you see, I'm going to date myself. The 60th anniversary of Adam West as Batman, January 12th, 1966. So, I'm preparing myself for the 60th anniversary because I'm still a small child.

Yeah. I don't know if you can see behind me, though. See, I had that made. That's a Superman fighting Muhammad Ali, actually. And if you look closely, I'll take a picture. My wife and I are sitting next to Batman and Sonny Bono. I had us drawn into the picture. See, you got to stay young, Elson. Okay.

Think about the story. Think about the mythological lore of Superman. He grows up in a small town. He's obviously adopted. So there's some little bit of loneliness and need for achievement and he's now got to make his way in the big city. So this is aspirational American dream and of course he's trying to do the right thing. Remember Ed, Superman is who we want to be. But Batman, Batman is who we are. We're dark. We're disjointed. You know, we got lightness and darkness in us.

Exactly. Superman is all about the light. Batman a little bit dark like us, you know.

Well, first of all, you're being very generous and I appreciate that and I'm a huge fan of yours and you are also an entrepreneur. So, you know, you have to go from zero to one. And that's a hard thing for people when they really think about it because I can remember when I started SkyBridge at it was 2005. My daughter was 9 years old and I was printing out this PowerPoint. It was a very antiquated PowerPoint presentation. And she says, 'Dad, aren't you at Lehman Brothers?' I said, 'Yeah.' She goes, 'Well, all my friends here in this neighborhood work at Lehman Brothers. What the hell are you doing? Why are you... This is just a piece of paper, this SkyBridge thing.' I remember looking at her laughing. I said, 'Yeah, but I'm going to turn it into something.' So, so you've got to go from zero to one. You get that. Scott Galloway gets that. And with that, there's a journey. There's an adrenaline rush. There's desperation. There's moments of despair. And there's a lot of anxiety that goes into that because you don't know if you can make it or not. And so, my journey actually started at 11. And what happened to me was I was home from school. My dad got home early from work because he was a construction worker. Lunch pail went into the refrigerator at 10:00 p.m. He woke up at actually 3:45 a.m. Got himself ready by 4:15. He was out the door. He was on the job site by 5:00 a.m. and he came home at around 3:00, 3:30. So I was home from school. My dad was getting home roughly at the same time and there was a lot of commotion and screaming and anxiety in the house. I guess he had gotten his hours cut back and you know he was an hourly worker and he was subjected to the whims of the economy and his foreman and so on and so forth. Very hard worker and you know we lived in the middle class. I would never even want to try to even dishonor my dad's work effort to suggest we grew up poor but we had financial anxiety. So there I was 11 years old. I said, 'Okay, I go get myself a paper route.' So, I got my work papers. I went to Long Island Newsday. Mr. Fusco, may his soul rest in peace, he gave me 15 houses. And after school, I would ride around on my 10-speed bicycle and I would deliver the papers and I would collect. And then I said to Mr. Fusco, 'Listen, I have a great idea. I want you to give me 30 papers on Wednesday.' When I went into the local apartment buildings were all blue-collar Irish and Italian ladies and I dropped the newspaper off at every door and I rang the doorbell and I said, 'Oh, Mrs. Sheridan, how are you? Mrs. Elson, how are you? I mean, this is a free paper from Long Island Newsday.' And then the next day I showed up and I rang the bell and I said, 'Mrs., you know, would you be willing to subscribe? I'm trying to build my account base. I'm trying to build my network.' And I built the biggest paper route in that town. I was making like $60 a week. I was giving 45 of it to my parents. Again, this is like 1975, 1976. And so I got the hustle in me very, very early. And then when you have the hustle in you, and this is a first time founders podcast, so people should listen up. When you get the hustle going, you build your self-confidence, you know. Yes. Did some women say, 'No, I'm sorry, Anthony. I don't want to subscribe to Long Island Newsday.' Sure. Could I have had a rejection rate of 30, 40%? Yes. But I was converting accounts and I was building a little bit of a large S for myself and I was hustling those papers and it got me into the mode of thinking like that. So then I went to work at the local supermarket. I worked at my uncle's motorcycle shop. And by the time I was in high school, I had three jobs I was working because I needed the money for potentially going to school and I needed the money to help my parents and I got that mindset. So the first thing I would say to people, you have to believe you can do something and then you have to put a foot forward with imperfection. You know, if you're waiting for your business plan to be perfect, if you're waiting for the idea to be scintillating, the website to look pristine, you're waiting too long. You got to get your ass going. You got to get up and go. And then you have to adapt yourself when things are going wrong. And when things are going right, you don't get too cocky, you know. And so that's really my origin story. And you know, I owe a lot to my mom and dad, but really my dad's work ethic. He was a hardworking. He was a tough guy. He's hard on us in the house, but he was a very hard worker and he played things straight. That was the other thing. You know, my dad, if my dad had a parking ticket on Main Street in the town I grew up in, he would walk to the post office to get a money order to pay the parking. He wouldn't even wait to go home to write a check. That was my old man. That's how he thought about things. And so I always tell the people at SkyBridge that my dad gave me my last name clean, Ed. Paid his taxes, paid his bills, worked super hard. So we're never going to do anything wrong at SkyBridge. We can't do anything to dishonor that. You know, I don't need the money, okay? But what I do need is for people to think that we're ethical and people think that we have high integrity. And so you've got to fuse those things together. You got to fuse the work ethic, the ambition, the willingness to go on that arc, that journey which has all that trepidation and adrenaline and you know fiascos happening. But then at the same time you got to make sure you maintain your integrity in all circumstances because I've had some really bad things happen to me. I went into business with Sam Bankman-Fried who's spending 25 years in jail. If I didn't do everything right, block and tackle and watch my P's and Q's during that business transaction, I could have been embroiled in something. And you know, your colleague and partner Scott Galloway and I always talk about this. If you have integrity, you will always have opportunity.

Yeah, I think you do. I think you have a moment, as I was trying to say, where you start to build self-confidence. You're like, okay, you know, Mrs. Sheridan said yes. Mrs. Smith said no. But let me keep digging here. You know, there's a... every time I get a no, there's got to be a yes around the corner. And you start to develop some level of self-confidence. But I think the thing I'm getting at, you have to start. Like I think what happens to us, we get anxiety about starting and we also have to relax the shame gene in our personality. So we have to say to ourselves, okay, it may not work and then can I live with myself? You know, I always call it the cocktail party test. You know, can you walk into the cocktail party and be the rugged startup person when the other person's working at Goldman Sachs and their career is moving gradually but diagonally positive and yours is going like a cardiac EKG? Can you be comfortable with that? You know, I worked at Goldman. I spent seven years there. Was in a phenomenal place. Had a great career there. I left Goldman to start my own business. So, I went from making big money in my 30s to no money to start my own business. And I remember that anxiety and then when it started to work, I'm going to tell you the story because you'll get a kick out of it. A couple of my friends from Goldman was like, 'Wow, your business is doing great. You're making your own way. I'm going to go start my own business.' And I remember one of my buddies coming into my office and say, 'Okay, I'm going to leave Goldman start.' And I said to him, 'Okay, can I show you my summer house? Do you mind? I would like to show you my summer house.' And the guy looked at me. He said, 'What do you mean?' I said, 'Well, come down the hallway. Let me show you my summer house.' And I opened the door to a closet and it was a server farm. And there was $700,000. That was a lot of money back in the late 90s. Okay? There was $700,000 of servers, network switches in the closet. And I looked at them. I said, 'This is my summer house in the Hamptons.' Okay. Because I had to put all of my money into this tech to run the trading desk. I said, 'So, if you're willing to put your summer house in the closet here in the office at 900 Third Avenue, which was this nondescript commercial office building I started my company in. If you're willing to do that, then you should do it.' And but you're not going to be at that cocktail party with your pinky up in the air in the Hamptons or showing off your artwork in the house because you're going to be putting the money back into your business.

So, so, so, so, so to me, it's a methodology. It's a way of thinking and you have to not care. You have to not care if it's not going well. You know, I've had at least as I'm a public figure, as you pointed out, I've had at least three, possibly four financial obituaries. Three or four. This is... You put this on YouTube, right?

All right. Let me show you something. This is because we got clowns in my office. Okay. And so, for people listening, this is a bobblehead of me sinking in a dinghy called the SS Mooch. You see it? And so the New York Post in 2022 said Scaramucci is a loser. He bought Bitcoin. Bitcoin's going to zero. And they had this caricature. I looked like Tyrion Lannister, like a little tiny guy sinking in the Bitcoin boat. And the comedians at SkyBridge, they made a bobblehead for me. Okay. Now, you could be upset about that or you could own it. I took a picture of it. I blew it up. I framed it. Put it in my office because my attitude is if I'm going down, I want to go down gloriously. But if I'm not going down, I want to remind people that they may have bet the wrong horse thinking that I am going down. Right. But here you go. What do you think?

Not bad. Right. I think the hair looks great on this.

But it's a five or a six head. Actually, it's not really a forehead. That's the problem. What I'm making, you got to stay in things. And you got to... and by the way that doesn't mean you stay in things if they're not working. You know the beauty of what I'm saying is you stay in things but when someone says never give up. That's right. You never give up on a business or the business but you may have to shut down a fund. You may have to shut down a product line. You may have to say oh that's not going in the right direction. I got to go this way. Right? You know Amazon starts with the retail operation and they figure out wait a minute we've got the technology. We can go into web services. It turns out the web services is as valuable if not more so than the retail operation and then it makes it easier for them to develop a streaming business. You see there's an adaptation. Said differently. SkyBridge Capital is not the firm that I started. If you looked at that PowerPoint that I was showing my nine-year-old daughter that's now 29, it's not the firm that I started. I innovated. I moved. I shifted the business from hedge fund management, fund of funds into crypto and private equity. It's moved as our society has moved and we've made these adaptations.

I was an economics major and a classics minor.

This is really not a great answer. So, I'm going to tell you the real answer. So, I had no clue what I was doing. My parents wanted me to go to college. I had very high test scores and I had a terrific guidance counselor. Again, may his soul rest in peace. John Zenetti, Italian American. He's my guidance counselor. And he came to my parents' house and he was smoking cigarellos like my parents. And they, Ed, you got to see the scene. I had a little tiny house, a little tiny kitchen. My mother's making espresso out of this cast iron pot that my grandparents brought from Italy in the 1920s and the espresso is coming out like motor oil. I don't know how these people's hearts didn't blow up. Okay, they're smoking cigarellos and they're drinking motor oil espresso at the table and Zenetti tells my parents in Italian. I had gotten into Binghamton which was our state school and then there's a private college called Tufts that I got into. My father thought that Tufts was spelled T-O-U-G-H-S. He had no clue. I mean, he had no idea what it was, right?

He's sitting there smoking cigarellos and they're talking in Italian and Zenetti says, 'You got to send the kid to the private school.' And my dad was like, 'Hey man, I don't have the money.' You know, I mean, the private school's 24,000. I mean, these are 70 or 80,000 now, but I'm talking about in the 80s, right? And so, Zenetti said, 'No, he'll figure it out. He's an industrious kid. He'll get a job. He'll get some work study. He'll get a loan from the school, you know, blah blah Pell Grant.' And so my father was like, 'All right, if you think that's the right thing to do, we're going to do that.' And so my father in April of 1982 and he handed me a check and I was a senior in high school, I accepted the admissions at Tufts and he handed me a check for $10,000. When I looked at it, I said, 'Pop, where is this from?' He said, 'Well, I cashed in my union life insurance.' Because he took the cash value of his life insurance, Ed, and he gave it to me in a check. He said, 'I don't have a lot of money for you to go to school, but this will get you started.' And that was an explosion for me. That was like an epiphany for me. I was like, 'Oh my god, my dad is cashing his life insurance. I got to make sure I don't disappoint these people.' So, I went to Tufts. I did very well there. You know, not bragging, just tell you the fact I graduated Summa Cum Laude. I was Phi Beta Kappa and I was trying to figure out what to do. And I read a newspaper article. I think it was in Time magazine actually. It said that Wall Street lawyers were making $65,000 a year. Okay? And this is like 1985. And I'm like, 'Wow, that's like double what my dad makes.' And so that's why I went to law school. I would love to tell you it was some kind of intellectual odyssey and all this stuff. I just looked at that and said, 'Well, my dad's making 32,000 a year. We're doing okay. I can come out of law school and be double what he's making. I mean, that's more money than I even want or need.' This was the superficiality of my decision-making back then. And it's important for the first time founders podcast because now I got to adapt and pivot because if you want to be a first-time founder, guess what? You got to adapt and pivot. So, I go to law school. I hate every minute of it. I'm coming home for Thanksgiving. I tell my mom I want to drop out of law school and maybe apply to business school or do something different. She's an old school Italian. She basically tells me she's going to kill herself. I mean, you know what they're like, these dramatic Italians, right? I'm going to kill myself. You're going to kill yourself? I just don't like being in law school. Okay, but this is the best part of it, Ed. Okay, so I finish law school, but I get a job at Goldman Sachs. My mother feels bad for me. This is terrible. She says to me, 'You're now working as a lawyer. This is terrible. This is terrible.' So, I'm in Rosano's deli on Long Island. I'm getting myself an Italian sub, like Italian submarine sandwich, right? And Mrs. Kazenza is behind me and she looks at me. She says, 'How you doing at that law firm Goldman and Sachs?' I said, 'Well, excuse me.' She had the law firm. Your mother tells me you're working at a law firm. And I look at her. I'm like, 'Yeah, I'm doing great, Mrs. Kazenza. Mrs. C. I'm doing great.' And I call my mother. I'm like, 'Ma, I'm not working at a law firm.' I told her you were working at a law firm. I'm embarrassed for you. This is my parent. This is how my parents were. Okay. So, you know, to me, I went to law school for these very superficial reasons, but I'm very happy I did it because that was a phenomenal education. Of course, I got to experience Harvard, which was a real culture shock for me because I didn't go to a boarding school. I didn't have any legacies there. You know, I showed up in my Levi's jeans and a motorcycle leather jacket. And I had to get myself adjusted from a blue-collar world into a white-collar world. And Harvard was great, great to me and great for me for that.

Well, first of all, I didn't have the right clothing. I didn't have the right style of dress. You know, I remember my first interview at Goldman. The guy said to me, 'Dude, I can't bring you down. You look like an undertaker from Brooklyn. You're like in 100% poly. Okay. You're going to... you're like fully flammable for the job interview. You're a very smart guy, but you got to go buy natural fiber clothing.'

And I remember being humiliated by that. And I went and got a credit card and I bought the clothing. So I was always awkward in the beginning.

I think it's very important to tell people the truth. Okay. I was awkward. I was making mistakes.

But also your background. A lot of people from my background weren't on Wall Street. And so, you know, there were some, but not many. And I was a little bit of a fish out of water. I wasn't really in the club, if you would call it that. This is another thing I would say about first-time founders. Are you a comfortable or uncomfortable outsider? So, if you're an uncomfortable outsider, that's somebody like Trump. He's an uncomfortable outsider. He doesn't like the fact that he can't get into your golf club. He doesn't like the fact that you won't invite him to that East Upper East Side salon dinner. So that pisses him off. So he goes and builds golf courses or he goes and runs for president to shove himself up your ass. Okay? Because that's him. Okay? But that's an uncomfortable outsider. I'm a comfortable outsider. I grew up on Long Island. I didn't grow up in the Hoi Polloi. None of my parents. There's no legacy. So I'm a comfortable outsider. Why that's important is if you're a comfortable outsider, you can be comfortable with yourself and you could acknowledge your shortcomings in certain situations. I think it helps you, you know. And so for me, I looked around in the room. I said, 'Okay, I don't fit in with these guys. I'm making good money for them. I'm not going to get into their golf courses. I'm not going to be invited to their supper clubs. So what I'm going to do is I'm going to go start my own business.' There was an Italian American money manager. His name is Mario Gabelli. He's 85 today. He's one of my dear friends and mentors. When I was 30 years old, so this is like 31 years ago. I had breakfast with him. He turned to me. He said, 'Anthony, you're a young guy. You're 30. But in 10 minutes, you're going to be 50. If you stay at Goldman Sachs, you don't fit in. You're going to have to like shave the points off your personality.'