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

Transcript

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Speaker 24 Welcome to First Time Founders. I'm Ed Elson.
My next guest rose to fame in 2017 as Donald Trump's White House Communications Director, a role he famously left after just 11 days.

Speaker 24 His blunt, unfiltered style made him a household name. But long before Washington, he was making waves on Wall Wall Street.

Speaker 24 And in 2005, he founded Skybridge Capital, a New York-based alternative investment firm with several billion dollars in assets under management.

Speaker 24 Four years later, he launched the SALT Conference, now a global stage for leaders in business, finance, and politics that hosts thousands of attendees every year.

Speaker 24 And today, he's an outspoken voice at the intersection of media, markets, and policy. Here is my conversation with Anthony Scaramucci, founder and managing partner of Skybridge Capital.

Speaker 24 Anthony Scaramucci, thank you for joining me on First Time Founders.

Speaker 25 Hey, that means I'm very flattered to be on it. Thank you.
I like the name. I need swag.

Speaker 25 Okay, I need swag. Okay, first time founders, I want to wear a shirt, a hat.

Speaker 24 Well, you're wearing your Batman shirt, and that's pretty swaggy, I'd say.

Speaker 25 Well, okay, so you see, I'm going to date myself the 60th anniversary of Adam West as Batman, January 12th, 1966.

Speaker 25 So I'm I'm preparing myself for the 60th anniversary because I'm still a small child.

Speaker 24 But I also know that you're a big Superman fan.

Speaker 25 That's your ultimate superhero, right? Yeah, I don't know if you can see behind me, though. See, I had that made.
That's Superman fighting Muhammad Ali.

Speaker 25 Actually, and if you look closely, I'll take a picture of my wife and I are sitting next to Batman and Sonny Bono. I had us drawn into the picture.
See?

Speaker 25 You got to stay young, Elson. Okay.

Speaker 24 First time I met with Anthony in person, we went to Skybridge, which is what we're going to talk about.

Speaker 25 But

Speaker 24 in the front of the Skybridge lobby, there is a giant Superman statue. This guy loves Superman more than anyone else.

Speaker 25 It's pretty incredible. Think about the story.
Think about the mythological lore of Superman. He grows up in a small town.
He's obviously adopted.

Speaker 25 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.

Speaker 25 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.

Speaker 25 We're dark, we're, we're disjointed, you know, we're, we got, we got lightness and darkness,

Speaker 24 and we're not endowed with supernatural powers.

Speaker 25 Exactly. Superman is all about the light.
Batman, a little bit dark like us, you know?

Speaker 24 Well, I'm really glad to have you on. I wanted to have you on this program.
We've talked with you before. We've talked with you on property markets.
You've talked with Scott on Lost Boys.

Speaker 24 You have a lot of political experience. I think many people know you

Speaker 24 for your time in the White House. But, you know, the way I think about you, and the reason I wanted to have you on this program is you are kind of the ultimate entrepreneur.

Speaker 24 You are the ultimate self-starter. I mean, grew up Long Island, blue-collar background, worked your way onto Wall Street.
You were a scrappy guy on Wall Street, made your connections.

Speaker 24 You're, I mean, one of the greatest networkers networkers I know. That's something I've learned about you.

Speaker 24 Started your own investment firm, then started another investment firm, started a global conference, which has become extremely popular. That's the SALT Conference.

Speaker 24 You are, you might be a public figure and you might have a background in politics, but you are really an entrepreneur. And so I wanted to have you on this

Speaker 24 program to hear about your entrepreneurial background, what drives you, what led to Skybridge, what led to the SALT Conference. And I guess where we should start is probably just your background

Speaker 24 growing up in Long Island.

Speaker 24 Tell us a little bit about your upbringing and your childhood.

Speaker 25 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.

Speaker 25 And that's a hard thing for people when they really think about about it. Because

Speaker 25 I can remember when I started Skybridge,

Speaker 25 it was 2005. My daughter was nine 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.

Speaker 25 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.

Speaker 25 I remember looking at her laughing. I said, yeah, but I'm going to turn it into something.

Speaker 25 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.

Speaker 25 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.

Speaker 25 My dad got home early from work because he was a construction worker. Lunch pail went into the refrigerator at 10 p.m.

Speaker 25 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 a.m.

Speaker 25 And he came home at around 3, 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.

Speaker 25 I guess he had gotten his hours cut back.

Speaker 25 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.

Speaker 25 I would never even want to try to even dishonor my dad's work effort to suggest we grow up poor, but we had financial anxiety. So there I was, 11 years old.

Speaker 25 I said, okay, I'm going to go get myself a paper route. And so I got my work papers.
I went to Long Island Newsday.

Speaker 25 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.

Speaker 25 Fusco, listen, I have a great idea. I want you to give me 30 papers on Wednesday.
And I went into the local apartment buildings. These were all blue-collar Irish and Italian ladies, Ed.

Speaker 25 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.

Speaker 25 And then the next day I showed up and I rang the bell and I said, Mrs. Elson, you know, would you be willing to subscribe? I'm trying to build my account base.
I'm trying to build my network.

Speaker 25 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.

Speaker 25 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.

Speaker 25 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 News Day? Sure.

Speaker 25 Could I have had a rejection rate of 30, 40 percent? 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.

Speaker 25 And it got me into the mode of thinking like that. So then I went to work at the local supermarket.
I worked in my uncle's motorcycle shop.

Speaker 25 And by the time I was in high school, I had three jobs I was working because I needed the money at. I needed the money for potentially going to school and I needed the money to help my parents.

Speaker 25 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.

Speaker 25 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.

Speaker 25 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.

Speaker 25 And when things are going right, you don't get too cocky. And so that, that's really my origin story.

Speaker 25 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.

Speaker 25 And he played things straight. That was the other thing.

Speaker 25 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 ticket.

Speaker 25 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,

Speaker 25 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.

Speaker 25 But what I do need is for people to think that we're we're ethical and the people think that we have high integrity. And so you've got to fuse those things together.

Speaker 25 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

Speaker 25 fiascos happening.

Speaker 25 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.

Speaker 25 I went into business with Sam Bankman Freed, who's spending 25 years in jail.

Speaker 25 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.

Speaker 25 And, you know, your colleague and partner, Scott Galloway, and I always talk about this. If you have integrity, you will always have opportunity.

Speaker 24 I think one of the interesting things about you describing your childhood there. is clearly you have the hustle in you, you're working hard, but it also sounds like you have

Speaker 24 a talent in you. It sounds like you were a pretty

Speaker 24 remarkable salesman from quite a young age. You're going around door to door, you're charming people, you're setting up these accounts.
It sounds like you had sort of a knack for this.

Speaker 24 Do you think that that is something that you recognized in yourself? Did you feel confident in your abilities?

Speaker 25 I mean, you probably don't want me to go full on existential, but I do believe that we're coming into the world with an operating system.

Speaker 25 You know, there's some of us that are musical and some of us can sing beautifully and some of us are great mathematical minds or some of us can see things differently from a physical perspective.

Speaker 25 And I think I came in with some emotional intelligence, thank God. I think I got raised pretty well.

Speaker 25 I mean, not with, you know, if you find me the family that's perfectly functional, I'll find you the family that's aligned.

Speaker 25 You know, our family motto was let's keep the word fun and the word dysfunctional. So I'm not trying to say it was pristine or anything like that, but but we got raised, right?

Speaker 25 We got raised with a good set of values and things like that.

Speaker 25 But I do think you come in, you know, my brother's very mathematically inclined. I'm not.
I'm more historically informed.

Speaker 25 You know, I can read things and assimilate information pretty quickly, but I'm not probably the best family member in math.

Speaker 25 You know, so you have to pick and choose what you are and then also be self-aware. You know, so I, you know, I, and again, if you're self-aware, then you have the self-confidence to delegate.
So if

Speaker 25 you and I are working together, I can figure out what your skill set is relative to mine. And then here's all the work relative to your skill set.

Speaker 24 Which is, by the way, one of our biggest recommendations on

Speaker 24 all of our podcasts is if you want to be successful, you need to identify what your talent is. And then you need to invest heavily into that.
But that first step is actually quite difficult.

Speaker 24 When you're 11 and you're selling these papers and it's working, do you have a moment where you're like, I'm pretty good at this, I should keep doing this?

Speaker 25 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,

Speaker 25 you know, Mrs. Sheridan said yes, Mrs.
Smith said no, but let me keep digging here.

Speaker 25 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

Speaker 25 I think the thing I'm getting at, you have to start.

Speaker 25 Like, I think what happens to us, we get anxiety about starting,

Speaker 25 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?

Speaker 25 You know, I always, I always call, I call it the cocktail party test.

Speaker 25 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.

Speaker 25 Can you be comfortable with that? You know, I worked at Goldman. I spent seven years there.
It was in a phenomenal place, had a great career there. I left Goldman to start my own business.

Speaker 25 So I went from making big money in my 30s to no money to start my own business. And

Speaker 25 I remember that anxiety. And then when it started to work,

Speaker 25 I'm going to tell you this 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.

Speaker 25 I'm going to go start my own business. And I remember one of my buddies coming into my office and saying, Okay, I'm going to leave Goldman.
I'll go start my own business.

Speaker 25 And I said to him, Okay, can I show you my summer house? Do you mind? I'd 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.

Speaker 25 Let me show you my summer house. And I opened the door to a closet, and it was a server farm.
And there were $700,000. That was a lot of money back in the late 90s.

Speaker 25 There was $700,000 $700,000 of servers, network switches in the closet. And I looked at them, I said, this is my summer house in the Hamptons.

Speaker 25 Because I had to put all of my money into this tech to run the trading desk.

Speaker 25 I said, so if you're willing to put your summer house in the closet here in the office at 900 3rd 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.

Speaker 25 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 hard work in the house because you're going to be putting the money back into your business.

Speaker 25 Yes, exactly.

Speaker 25 So to me, it's a methodology, it's a way of thinking,

Speaker 25 and you have to not care it. You have to not care.

Speaker 25 And 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.

Speaker 25 This is a this is you put this on YouTube, right?

Speaker 25 All right, let me show you something.

Speaker 25 This is

Speaker 25 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?

Speaker 25 And so the New York Post in 2022 said Scaramucci's a loser. He bought Bitcoin.
Bitcoin's going to zero. And they had this caricature.

Speaker 25 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.

Speaker 25 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.

Speaker 25 Yes. 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. Yes.
Right. But here, here you go.
What do you think? It's beautiful.

Speaker 25 I think the hair hair looks great on this.

Speaker 24 I think the hair looks great.

Speaker 25 But it's a five or a six head, actually. It's not really a forehead.
That's the problem.

Speaker 25 What I'm making, you got to stay in things.

Speaker 25 And you got to, you got to, and by the way, that doesn't mean you stay in things if they're not working.

Speaker 25 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.

Speaker 25 You may have to shut down a product line. You may have to say, oh, that's not going in the right right direction.
I got to go this way, right?

Speaker 25 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.

Speaker 25 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

Speaker 25 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.

Speaker 25 I innovated, I moved, I shifted the business from hedge fund management, funder funds into crypto and private equity. It's moved as our society has moved and we've made these adaptations.

Speaker 24 Yeah, you seem to have a belief in yourself. And I think that is why you've been able to go up and down the roller coaster so many times.

Speaker 24 You've had extremely high highs and you had extremely low lows, which I think is what it means to be an entrepreneur and a founder. And as you say, that is what you're signing up for.

Speaker 24 That's the thing that a lot of people seem to not really understand.

Speaker 24 I think they see the glitz and the glamour of being a success, but you got to realize you're basically signing up for going through the trenches.

Speaker 24 And that requires a level of resolve and a level of self-confidence and belief in yourself to not be so discouraged when you're down. I want to figure out how

Speaker 24 the mooch got there. So

Speaker 24 you graduate from high school, you go to Tufts, where I believe you actually studied classics, right?

Speaker 25 I was an economics major and a classics minor.

Speaker 24 You know, I had that in common. And then you go on to law school.
Why did you, and by the way, you, you, you, you get into Harvard Law.

Speaker 24 Tell us about that transition, going to Harvard Law School, why you wanted to be a lawyer and how that experience played out.

Speaker 25 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.

Speaker 25 And I had a terrific guidance counselor, again, may his soul recipes, John Zanetti, Italian-American, is my guidance counselor.

Speaker 25 And he came to my parents' house and he was smoking cigarellos like my parents.

Speaker 25 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.

Speaker 25 And the espresso is coming out like motor oil. I don't know how these people hearts didn't blow up.
Okay. They're smoking cigarellos and they're drinking motor oil espresso at the table.

Speaker 25 And Zanetti tells my parents in Italian.

Speaker 25 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.

Speaker 25 I mean, he had no idea what it was, right? That's better, I think. He's sitting there smoking cigarettes, and they're talking in Italian.
And Zanetti says, you got to send a kid to the private school.

Speaker 25 And my dad was like, hey, man, I don't have the money. You know, I mean, the private school is $24,000.
I mean, these are 70 or 80,000 now, but I'm talking about in the 80s, right?

Speaker 25 And so Zanetti said, now that 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, blah, blah, Pell Grant.

Speaker 25 And so my father was like, all right, if you think that's the right thing to do, we're we're going to do that.

Speaker 25 And so my father, in April of 1982, Ed, he handed me a check. And I was a senior in high school.
I accepted the, you know, the admissions at Tusk. And he handed me a check for $10,000.

Speaker 25 And I looked at it and I said, Pop, where is this from? He said, well, I cashed in my union life insurance

Speaker 25 because it 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.

Speaker 25 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.

Speaker 25 I did very well there. You know,

Speaker 25 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.

Speaker 25 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.

Speaker 25 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.

Speaker 25 I just looked at that and said, well, my dad's making $32,000 a year. We're doing okay.

Speaker 25 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.

Speaker 25 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.

Speaker 25 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.

Speaker 25 She's an old school Italian. She basically tells me she's going to kill myself.
I mean, you know, you know what they're like, these dramatic Italians, right? I'm going to kill myself.

Speaker 25 You're going to kill yourself?

Speaker 25 I just don't like being in law school. Okay.
But this is the best part of it, Ed, okay? So I finished law school, but I get a job at Goldman Sachs. My mother feels bad for me.
This is terrible.

Speaker 25 She says to me, you're not working as a lawyer? This is terrible. This is terrible.
So I'm in Rosano's Deli on Long Island.

Speaker 25 I'm getting myself like an Italian, like hoagie or Italian, you know, submarine sandwich, right? And Mrs. Kazenza's behind me, and she looks at me.

Speaker 25 She says, how are you doing at that law firm, Goldman and Sachs? I said, well, excuse me? She said, yeah, the law firm. Your mother tells me you're working at a law firm.

Speaker 25 And I look at her, I'm like, yeah, I'm doing great, Mrs. Kazenza.
Mrs. C, I'm doing great.
I call my mother. I'm like, maha, I'm not working at a law firm.
I told her you were working at a law firm.

Speaker 25 I'm embarrassed for you. This is my parents.
This is how my parents were. Okay.

Speaker 25 So, 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.

Speaker 25 Of course, I got the experience Harvard, which was a real culture shock for me, you know, because I didn't go to a boarding school. I didn't have any legacies there.

Speaker 25 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.

Speaker 25 great to me and great for me for that.

Speaker 24 So when you go to, then you go to Goldman and you're working on Goldman, you're working on Wall Street,

Speaker 24 presumably making a lot of money at that point, you describe

Speaker 24 this cocktail party dynamic

Speaker 24 where you got to go in there no matter how you're feeling and you got to go make friends with people.

Speaker 24 And you describe your blue collar background and you're going into this white collar world and then you're on Wall Street and you're rubbing elbows with these masters of the universe.

Speaker 24 How do you approach that? How do you walk into a meeting?

Speaker 25 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 with Goldman. The guy said to me, dude, I can't bring you down.

Speaker 25 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.

Speaker 25 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.

Speaker 25 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.

Speaker 24 I think these are the things that people don't really talk about.

Speaker 24 It's like, yeah, you can be smart and you can have a hard work either and all these things, but it's like something like clothes in these environments can be,

Speaker 24 it changes the whole game.

Speaker 25 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.

Speaker 25 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?

Speaker 25 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.

Speaker 25 He doesn't like the fact that you won't invite him to that Upper East Side salon dinner. So that pisses him off.

Speaker 25 So he goes and builds golf courses or he goes and runs for president to shove himself up your ass. Okay.
Because that's sin. Okay.

Speaker 25 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 Paloi.

Speaker 25 None of my parents, there's no legacy.

Speaker 25 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.

Speaker 25 I think it helps you.

Speaker 25 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.

Speaker 25 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.

Speaker 25 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.

Speaker 25 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,

Speaker 25 you're a young guy, you're 30, but in 10 minutes, you're going to be 50. If you you stay at Goldman Sachs, you don't fit in.
You're going to have to like shave the points off your personality.

Speaker 25 You're going to have to put yourself in this corporate box that you're not comfortable with. So go leave, start your own business, because someday you're going to be 50.

Speaker 25 And guess what you're going to want to do when you're 50? You're going to want to work. Okay, you're going to want to work.
And if you have your own business, guess what?

Speaker 25 People can't fire you, you know, if the business is successful. And I took his words to heart and I wrote down, I'm going to to start the business the minute I pay off my school loans.

Speaker 25 And so I paid off my school loans in May of 1996, about seven years after I graduated from law school. So I had loans from Tufts.
I had loans from Harvard.

Speaker 25 And in December of 1996, at the end of Goldman's fiscal year, I left to start my first company. And I took a big hit in pay.

Speaker 25 I moved into a small house, by the way. I didn't, you know, I wasn't trying to play the game of social status.
That's another big thing. You don't need it.

Speaker 25 You know, if you're an entrepreneur, what you need is the journey. You don't need to prove to somebody that you have more money than them.
You don't need to be driving a fancier car than them.

Speaker 25 What you need to be doing is putting your money into your business, your time, and your energy. See if you can make that business work.

Speaker 25 We'll be right back.

Speaker 18 SVB clients can help benefit from this combined commitment to tailored solutions, incredible service, and deep expertise from a top 20 bank with a national footprint.

Speaker 20 So, if you're serious about being a part of the innovation economy, there's really only one bank for you: Silicon Valley Bank. Yes, SVB.

Speaker 6 we have been a client of SVP at Property Media and my company before, L2, for better part of a decade.

Speaker 24 We're back with first-time founders. So you leave, you start Oscar Capital Management.

Speaker 24 You sell Oscar Capital Management in 2001, and then you go and you start another one, you start Skybridge. Tell us a little bit about those few years.

Speaker 25 So I left, I left in 96. I had a partner by the name of Andy Bozard, a phenomenal guy.
He's now also retired.

Speaker 25 And we started the business. It was sort of a registered investment advisor, and then we had a small hedge fund attached to it.
We won an advisor contract with Fidelity back in the year 2000.

Speaker 25 And so we were starting to get referrals from Fidelity for our registered investment advisor. It was really growing our assets.
And Newberger Berman wanted that.

Speaker 25 It was almost like buying an FCC license. So they came to me and said, listen, we want to get into that advisor referral program.
We'd like to own your business.

Speaker 25 We met with the New Burger-Berman management team and we did the deal. This is sort of

Speaker 25 a little bit of lore here. We had the meeting with Newburgh-Berman on the 5th of September, 2001, and we did the deal.
We shook hands on the deal. And then, of course, 9-11 happened.

Speaker 25 And so those guys said to me, okay, we got to come back to you. And I said, okay, this deal's not happening.
And we were in total tragedy mode in New York.

Speaker 25 And then on the 23rd of September, the CEO of the company called me and said, hey, we want to do the deal. Stock market's down 8%.

Speaker 25 The numbers that we promised you on the deal, we'd like to bring them down 8%.

Speaker 25 And so my partner and I caucused. And then our investment banker came up with a great idea.
He said, yeah, accept the deal, but get stock options in Newburger.

Speaker 25 So meaning if the markets rallied back, we would pick up the...

Speaker 25 you know, the economics in the stock. And so we took the deal with the stock options.
We moved over to Newburger on December 1st. And

Speaker 25 it was great. I enjoyed that.
Two years later, Newburgh got bought by Lehman.

Speaker 25 I got an opportunity to work at Lehman for a little while. I really got on with Dick Fold, the CEO there.
And I went to Dick and said, listen, I'm an entrepreneur.

Speaker 25 You have an awesome firm, but I would really like to start my own company. And Dick said to me, okay, if you can stay with me until the end of 2004, I'll put some money up and help you get started.

Speaker 25 And so my company in March of 2005 was started with money from Dick Fold, the CEO of Lehman, Merrill Lynch, my old investment banker that helped me sell the business. They each gave me $10 million.

Speaker 25 The computer entrepreneur Michael Dell, who's a friend of mine, gave me $25 million. And I put my own money in there, and we rolled it all together.

Speaker 25 I went out and raised some money, and we launched our fund with about $300 million.

Speaker 25 And that was our first fund, but it was a hedge fund seeding business. That's not the business we're in today.
Some of those worked, some of those didn't. We had the financial crisis.

Speaker 25 And during the financial crisis, we made a decision to buy Citibank's Fund to Funds business and their asset advisory.

Speaker 25 And

Speaker 25 I had to find money for that. So I got the money from all places.
I got the money from Australia. I went down to Australia.
I met with Challenger Financial.

Speaker 25 And I don't know if you know who James Packer is, but he's a very large, influential entrepreneur down there.

Speaker 25 His father was a big entrepreneur, multi-billionaire family.

Speaker 25 He owned Challenger financially, became a personal friend, and he bought 10% of Skybridge, which gave me the equity, Ed, to buy the Citibank business because they were forced to sell their business because of the tarp money that was coming into them from the federal government.

Speaker 25 So there I was in that business. And contemporaneous to that, because we were having a hard time raising assets during the crisis, I started a conference business, which ultimately became salt.

Speaker 25 So, all these things are accidental.

Speaker 25 I would love to sit there and tell you I had these brilliant visions and these brilliant strategies. I didn't.

Speaker 25 It was one foot in front of the other as we were trying to find our way to do things that we thought were creative and commercial to make the business a success.

Speaker 25 So, now we sit here today, very nice, you know, stable business, thousands of clients, some of it in crypto, some of it in hedge funds, some of it in private equity.

Speaker 25 And we've got this wonderful conference business that's been with us now for 16 years.

Speaker 25 And, you know, it's a fun business. And I like, you know, look, I get to do my podcasts.
I get to write books. I get to give some public speeches.
And I don't get censored.

Speaker 25 You know, there's no one looking at the first-time founders with Ed Elson and looking at the transcript and then calling you and say, oh, I got to take that out of the transcript.

Speaker 25 Okay, I'm the censor. You see what I mean? And that's one of the benefits of being a founder.

Speaker 24 One thing that stands out to me when you're starting Skybridge and

Speaker 24 raising the money, it's your relationships with people.

Speaker 24 I mean,

Speaker 24 a lot of getting started is about going to people, having established relationships with people. They have trust in you.

Speaker 25 They like you.

Speaker 24 And they're willing to say, yeah, we'll back you on this. And that sounds like that's really what got you there.
So I'd be interested to hear about your early relationship building.

Speaker 24 How do you view relationships with people? How much has it played into your success as an entrepreneur?

Speaker 25 I think for me,

Speaker 25 I think authenticity,

Speaker 25 I think if you think about the success of podcasters, like what makes a Galloway or an Elson or what makes a Joe Rogan, it's authenticity.

Speaker 25 Ultimately, people are tuning in to hear the raw version of the person. They want to hear that intimate conversation.
And so a podcast is

Speaker 25 like a radio show, well, there's, you know, a corporation may be tied to it and it's getting beamed out to millions of people, but a podcast, it feels dialed in and it feels very intimate.

Speaker 25 And the reason I'm using that as an example, I think you have to be that way with your customers. You have to be that way with your clients and your friends.

Speaker 25 And so for me, I've always had in my head that I want to have non-linear relationships with people, meaning I don't want to be a transactionalist.

Speaker 25 So if you called me and asked me for a favor, God bless, happy to do it. Okay, the flip side is

Speaker 25 I'm not looking for something. To build the relationship, you've got to think in a non-linear way.
And you've got to be out there.

Speaker 25 You've got to be a guy where somebody's willing to call you to ask you for a favor. You know, Ben Franklin had a great line.

Speaker 25 He said that if you want to make a friend, ask a person for a favor. It's sort of counterintuitive.
But what happens in human life, we have this reciprocity system.

Speaker 25 And what we know from influence around the world, that doesn't matter what the culture is, it doesn't matter what the language is, we do have this reciprocity embedded in us as social organisms.

Speaker 25 So if you call me and you ask me for a favor and I do it for you, well, you feel good about it and so do I. And all of a sudden, now we're engendering a relationship with each other.

Speaker 25 So you have to think about that from a sales perspective. I would call people and ask them for a favor, you know?

Speaker 25 And by the way, but I would also be open on the buy side to accept those solicitations from others asking me for favors. Do you see what I mean?

Speaker 25 It sounds very basic, but it's hard to do because if you're self-conscious, like, oh, shit, I'm not going to call Ed today and ask him for a favor.

Speaker 25 He may say no to me and then I'll be embarrassed, right? But you can't be embarrassed. You got to assume that you're going to get a lot of no's in life,

Speaker 25 but you got to work through that that in your own brain. You got to say, okay, the person said, no, I'm not going to take it that personally.

Speaker 25 It could be a reason why they're saying no that isn't really directly related to me.

Speaker 24 I also think it's an expression of vulnerability, which goes back to what you say about intimacy, authenticity. You're saying, look,

Speaker 24 I kind of need your help, but I would really appreciate your help, which is a vulnerable thing to do. At this time, you know, you're building your business.

Speaker 24 You're also starting to get into

Speaker 24 TV. You're doing TV appearances.
You're writing books. You're building this conference.
You're doing a lot of stuff at once. And I mean, by the way, writing books is its own entrepreneurial activity.

Speaker 24 It's a whole other business in and of itself. How are you juggling all of this at the same time? And I think it still applies today.
You've got one of the top podcasts, Reclus Politics US.

Speaker 24 You're again, you're doing speaking engagements. You're doing a lot of stuff.

Speaker 25 How do you do it all?

Speaker 25 This is very counterintuitive but if you want power if you want to gain power and increase your power you have to give it away i'm going to say it again because it's very important for people to listen you want be powerful you want to do a lot of things give your power away so John Darcy runs the conference business.

Speaker 25 He's the CEO of it. He's in charge of our business development.
He has the decision-making authority to book the location, get the sponsors, bring in the delegates.

Speaker 25 Brett Messing, my law school classmate, is the chief investment officer. He's empowered to put the portfolio together.
My compliance person, Marie Noble, is empowered to interface with the SEC.

Speaker 25 Again, not that I'm not talking to them regularly, not that I'm not helping them in different ways, but you've got to put yourself as a founder in the position of servant leader.

Speaker 25 What is a servant leader? I'm serving the people that are working. Ready, Ed? Not for me.

Speaker 25 They're working with me. Watch your pronouns.
It's not my company. It's our company.
It's not me. It's us.
You see what I'm saying?

Speaker 25 And so I have dedicated my life to delegation. I've dedicated my life to empowerment.
and autonomy for the people that are working with me. But on the flip side, I'll take the responsibility.

Speaker 25 So I'll go to somebody like John Darcy. I'll say, okay, look, you got the ball.
If something goes wrong, call me. We can blame it on me, no problem.
Okay, I want to encourage you to be the risk taker.

Speaker 25 You know, we had a situation, it was a really big amateur mistake by us. We didn't understand the holiday schedule in Singapore, and we booked the hotel to do a conference in Singapore.

Speaker 25 It turned out it was on like the Festival of Lights for 45% of the population and they were going to have most of the restaurants and most of the stuff was going to be closed.

Speaker 25 It would be like it would be like you and me say, okay, we're going to do a salt conference. We're going to do it on Christmas Day though.
Let's see if we can make it happen, right?

Speaker 25 I mean, it was really

Speaker 25 asinine. It was really amateur hour.

Speaker 25 And

Speaker 25 my team came to me and they're like, I don't know, man, we screwed up. We didn't check the holiday schedule.
And sort of, you know, the hotel should have told us probably, but we booked this.

Speaker 25 And I said, all right, well, how much is it going to cost us to get out of it? Well, it's going to cost us about $650,000. I gulped.

Speaker 25 I said, all right, let's see if we can negotiate it at least down to $500,000. I think we ended up paying $600,000 to get out of the contract.
But I didn't blame them.

Speaker 25 I didn't do this like the scarecrow and the wizard of Oz and start blaming everybody. I said, okay, I'm accountable.
Put you guys in charge. You made a mistake.
Not a big deal. Let's rock and roll.

Speaker 25 Let's go forward.

Speaker 24 And how does that lead to success and to attaining power? I agree with you. It's the outstanding thing to do.

Speaker 25 Because it empowers people. It makes them think, this guy has my back.
I did make a mistake. He knows I made a mistake.
I know I made a mistake. But he's not pillaring me for it.
If anything,

Speaker 25 he's trying to boost me up to make me more accountable. You want to, you know, to be an entrepreneur, you have to train train entrepreneurs.
Okay.

Speaker 25 You have to be in an entrepreneurial mindset with the people that are working with you. Oh, you want to run something someday? Okay, run it now.
Take this piece of our business. You run it.

Speaker 25 Report to me. Oh, you need me to make a call for you to secure a sponsor? No problem.
Oh, you need to get a speaker. You need Scott Galloway to come and give a keynote.
I know Scott.

Speaker 25 Let me give him a call. Oh, you're trying to make that investment in XAI.
I know two of the board members. Let's see if we can get the board to find us some stock for our private equity fund.

Speaker 25 You follow what I'm saying? But now I'm in a seat of service. And what you don't want to be is a bottleneck.

Speaker 25 What you don't want to be is everyone's got to come to you to make every decision in the company. Then you can't do all the things that I'm doing.

Speaker 25 Reagan had a plaque on his desk in the Oval Office, and I showed it to you when you came to my office. There's a little tiny plaque.

Speaker 25 It says you can get anywhere you want in life as long as you don't care who gets the credit. And the point is you got to empower people.
If you empower people, you become more powerful.

Speaker 25 And I think that's something is a very big lesson for me that I've learned over the years of managing a company.

Speaker 24 And I'm sure it also helps with just retainment, employee retainment. I mean, you win people's trust.

Speaker 25 Remember, you want people to feel a purpose. And when you give them that kind of responsibility where they're doing the decision, guess what? They feel quite purposeful.

Speaker 25 Purposeful people tend not to to leave companies.

Speaker 24 How do you think about this when it comes to hiring talent? I mean, you have a lot of young, smart people, analysts working at Skybridge.

Speaker 25 How do you pitch the company?

Speaker 24 How do you bring people onto your team?

Speaker 25 Well, I have a big summer program. So I sort of stole that idea from Goldman and some of the big investment banks.
I always have 20 people in the summer program.

Speaker 25 We bring them in from great schools, or we may have a personal connection to them somehow.

Speaker 25 And so we get a lot of our talent actually from our summer program. I like training people from day one.
We don't really have a lot of lateral hires into a place like Skybridge.

Speaker 25 It's sort of, I can't give it a British football comparison, but I can give it an American baseball one. We have like a minor league system, and we're trying to grow the talent from in.

Speaker 24 We're not really trying to pick off youth academy in football terms.

Speaker 25 Yeah, exactly. We're not trying to pick off free agents, you know.

Speaker 25 And so that's one way we do it. I think the second thing that we do, which I think is super important,

Speaker 25 is

Speaker 25 want to hear ideas. I want to hear pitches.
So I've had people come to me and say, here's my idea.

Speaker 25 And if we not like them and we know them, we may seed them with some money, may put them on the desk somewhere and see if they can, you know, figure out a way to grow a business inside of our business.

Speaker 25 That's an idea that we do. I have an open door policy, meaning if you called me and said, hey, I've got XYZ,

Speaker 25 he's interested in working at Skybridge, I will invariably see the person because my attitude is that's where the opportunities are.

Speaker 25 I can't tell you the number of times I didn't want to take a meeting, but I took the meeting and it turned out it was a great idea for Skybridge.

Speaker 25 It was a great idea or, or it was a great idea for somebody else. And I was able to pass it off to one of my friends.
You know, so I take, my wife gets mad at me, my assistant gets mad at me.

Speaker 25 I take way more meetings than I probably should. But I also have this attitude where I like paying things forward.

Speaker 25 You know, so I went to the London School of Economics where where I spent a semester in college and I spoke, I don't know, it was last spring, maybe it was April or May.

Speaker 25 I was at the London School of Economics, you know, off the strand there. And I spoke for an hour and then I probably was there for two additional hours.

Speaker 25 And you say, well, what the hell was I doing in the two additional hours? I was talking to the people. that lined up to speak to me after the event.
So what the hell are you doing that?

Speaker 25 You could have had a bodyman or something like that that get you out of there. But that's what I had to do at.

Speaker 25 I had to go to events like that with my electronic typewriter written resume. And I had to wait for the guy to get done speaking.

Speaker 25 And hopefully I could get my resume to him and say, hey, blah, blah, blah. Could I come see you? Could I meet you at Goldman? Could I do this? Could I do that? Could I buy you a cup of coffee?

Speaker 25 Could I drive you to the airport? How about that one? Can I drive you to the airport? I had a little Honda Civic.

Speaker 25 can i drive you to the airport instead of you taking a cab i mean i had all the tricks you know but i had to do that to get to where i am so when i'm there now i want to pay it forward so i'll hang out with the people you know i've invited some of these people to go see us at the uh indigo arena at 02 or i i said okay come next time you're in new york or do a zoom call with my sales team

Speaker 25 I just think it's important because then, you know, what happens is positive, positive karma. And people say, hey, the guy's approachable.
He's willing to,

Speaker 25 he's willing to be open.

Speaker 25 And by the way, I needed people to be open with me yet.

Speaker 25 And I always tell these young kids, if I do them a big favor, like, oh, what can I do for you? Nothing. But 10 or 15 years from now, pay it forward.

Speaker 25 We'll be right back.

Speaker 18 SVB clients can help benefit from this combined commitment to tailored solutions, solutions, incredible service, and deep expertise from a top 20 bank with a national footprint.

Speaker 20 So, if you're serious about being a part in the innovation economy, there's really only one bank for you: Silicon Valley Bank. Yes, SVB.

Speaker 6 we have been a client of SVP at Property Media and my company before, L2, for better part of a decade.

Speaker 24 We're back with first-time founders.

Speaker 25 So

Speaker 24 you're building a business and then

Speaker 24 you, of course, go into the White House. You have your 11 days,

Speaker 25 your

Speaker 24 unceremonious firing.

Speaker 24 The reason I bring this up,

Speaker 24 you've been through some of the greatest ups and the greatest downs ever.

Speaker 25 I'm glad you brought it up. I think it's an important part of my life story.
I don't shirk from or run away from that.

Speaker 25 I think it's important for people to understand is I'm not a

Speaker 25 politician.

Speaker 25 I'm a business person.

Speaker 25 I was having a very hard time breaking into the high net worth circles in New York or, frankly, the country.

Speaker 25 Can't play golf. I don't know how to.
I can't hit a tennis ball. I don't know how to.

Speaker 25 Never learned it as a kid. And so how was I going to meet these people? And it dawned on me that I could meet them through politics.

Speaker 25 And so I wrote my first check to Rudy Giuliani when I was, I guess, 28 or 29 years old. He was running for mayor.
He won, which was very helpful to me.

Speaker 25 And the fact he was Italian American was also helpful. He started introducing me to a whole waterfront of people.
He introduced me to George Pataki, who became the governor of New York.

Speaker 25 And then I met George W. Bush.
And then I had a series of things where I became a pretty well-known Republican fundraiser. How did I become a Republican?

Speaker 25 My dad's union, which which is sort of bizarre, most of these unions in America are controlled by the Democrats. But my dad's union here on Long Island was controlled by the Republican Party.

Speaker 25 And so when I registered for the draft and I signed up for the to register to vote, I asked my dad, am I a Democrat or Republican? No, no, you're a Republican.

Speaker 25 So I became a Republican, you know, and it'd be like, yeah, you're either a Man City or Manchester United. I'm a Republican.
I mean, stay loyal to your team, right?

Speaker 25 And so I was working for Republican candidates

Speaker 25 and successfully and unsuccessfully. And I was with Jeb Bush in 2016, and Trump called me.
I knew Trump from the city. I'd worked with Trump on a couple of charities.

Speaker 25 I'd gone a few Yankee games with Trump. I had a good relationship with him and his wife, for that matter.
I wasn't friends.

Speaker 25 You can't say that you're friends with somebody like Donald Trump because you're not. You just don't understand the relationship if you think that or

Speaker 25 you're overly name-dropping.

Speaker 25 And so he called me and said he wanted me to work for him on the campaign. I see you on TV.
You're good on TV. I want you part of my campaign.
I said, well, I'm with Jeb Bush. I can't, too loyal.

Speaker 25 I can't leave him. He said, well, if I knock Jeb Bush out of the race, I want you to come work for me.
And so I did.

Speaker 25 And that was a mistake. I didn't see Trump for who he actually is.
Again, again, I don't want to make the podcast political because it's very entrepreneurial, but I'm a balls and strikes person.

Speaker 25 Lifelong Republican. He's going to be the nominee.
I'm going to go work for him. And then he wins, Ed.
He wins. And then he puts me on the transition team.
And then I get intoxicated with the winning.

Speaker 25 And then I do something that is a real cautionary tale for everybody listening in. I put my pride and I put my ego into my decision making.
And so now I grew up in this blue-collar family.

Speaker 25 I'm with the Tufts in Harvard. I built two successful businesses.
I can go work in the White House for the American president. And my wife is like, please don't do that.

Speaker 25 I mean, she hates Trump like almost as much as Melania hates him. So that's like way, way up here, you know? And she's like, please don't do that.

Speaker 25 And I say, no, I got to do that because I got to fit this into my self-narrative. I've got to aggrandize my ego and my pride and all this silly stuff.
And so I go to work for him.

Speaker 25 My wife said something that turned out to be completely true. What did she say? She said, if you go work for him, it's different when you're in the campaign and you're a volunteer.

Speaker 25 If you go work for him, you're antithetical to him. You don't think the same way.
You don't carry the same cultural ideas about how to manage something.

Speaker 25 And he's really, he's the opposite of giving power away. You know, he wants all the credit for himself.
You're going to have a hard time.

Speaker 25 11 days in, we were fighting about different things.

Speaker 25 And I got fired. I knew I was getting fired on the Friday before.
I got fired on a Monday, but I knew I was getting fired on that Friday because I was fighting with him about something.

Speaker 25 And I was like, all right, this is not going to end well. I thought I was going to get fired over the weekend, but I guess they dropped the anvil on me on the Monday.
And I took it. It is what it is.

Speaker 25 I got excoriated in the press. I got beat up by late-night comedians.
I got ripped by a woman named Kara Swisher. I don't know if you ever heard about her or if you ever ran into her.

Speaker 25 And then, ironically, the poor lady, she had to sit with me side by side on a panel in San Francisco, which, of course, we ended up building a great friendship after that, right?

Speaker 25 I mean, you know, it's just the irony of life, right?

Speaker 25 And, you know, it hurt my business, hurt my reputation.

Speaker 25 But what did I do? I went into it, Ed. I didn't go away from it.
You know, I went on Jimmy Kimmel. I went on Bill Maher.
I went on Stephen Colbert. I didn't walk away from it.

Speaker 25 And I wasn't going to let it. in its one incident define me.
Sure, it'll end up in my obituary. That's fine.

Speaker 25 But I think it was very important for me to get my voice back out there so that I could three-dimensionalize who I am as opposed to just being a caricature the way your political adversaries want to frame you.

Speaker 25 I mean, remember, negative campaigning is prolific for one reason, Ed Elson. It works.

Speaker 25 Okay. And so you want to frame people with a caricature so that you can demean their arguments, right?

Speaker 25 One of the things you learn in trial advocacy at Harvard, if you're wrong on the facts, which you can be oftentimes, if you're wrong on the facts, do the ad hominem attack, attack the person.

Speaker 25 Okay, and that's what they do in politics. So I was getting lit up and attacked, but I took it.
And then eventually, you know, I didn't break from Trump right away after I was fired.

Speaker 25 I thought that would be, you know, I thought I'd be a weenie if I did that. And so I waited two years later when he was really, I thought, off the rails.
I said, look, I can't be a part of this.

Speaker 25 I can't support this type of behavior. And then the fight started with me and him.
And then the fight got, you know, it actually got fun for me.

Speaker 25 You know, I mean, he was like tweeting at me and I started hitting him super hard. And then he stopped tweeting at me.

Speaker 25 I think he figured out he was like, I was getting like 100,000 Twitter followers every time him and I were fighting. He's like, it's not worth it.

Speaker 24 You mentioned that you view it as a mistake to join the campaign and that you let your pride and your ego get in the way of

Speaker 24 clear thinking, I guess. But I just, I kind of want to push back on on that for a moment because at the same time,

Speaker 24 I get it in the sense that you're going after greatness and you're going off, as you say, the self-narrative, which you could say is, oh, I'm letting my ego get the better of me.

Speaker 24 But at the same time, that ego is a positive and powerful force that can drive you to go on and achieve great things. And you've, you know, established yourself in the Republican Party.

Speaker 24 You went for, you were supporting Jeb Bush. Bush and then through no fault of your own, Jeb Bush gets kicked out and then Trump's the guy.

Speaker 24 And then the next president of the United States, potentially the next president says, do you want to come be on my team? To which for me, if I'm you, even knowing what happened after,

Speaker 25 I'm saying yes. Here's the biggest lesson for first-time founders.

Speaker 25 When shit goes down and you don't like it and you've made a bad decision or you think you may have made a bad decision, forgive yourself. Okay, don't carry the millstone of regret around.

Speaker 25 You know, I've made so many bad decisions in business and missed an investment. I could have, I could have bought into Uber at a really early valuation.
I didn't understand the business.

Speaker 25 You know, I don't kick myself in the pants. I don't wake up in the morning and say, you know, I got fired from the White House eight years ago.

Speaker 25 Let me kick myself in the pants this morning and regret the things that went on in that decision making. You can't do that.

Speaker 25 And so I don't regret it, but I want to explain it to people so that there's a cautionary tale in there for themselves.

Speaker 25 And I think the lesson is get your pride and get your ego out of your decision making. If you're an investor, hiring somebody, taking a job, get your pride and ego out of the decision-making.

Speaker 25 You know, I made a decision to live in a way smaller house

Speaker 25 than I could afford. Why did I do that? I didn't want to have the financial insecurity if things went wrong in my business.

Speaker 25 I took my pride down. I said, this is comfortable.
It's bigger than the house I grew up in. You follow what I'm saying?

Speaker 25 And I'm trying to give you some philosophical tenets to think about as an entrepreneur, which will increase the likelihood of you doing well

Speaker 25 as an entrepreneur.

Speaker 24 The ups and downs, I mean, you've picked yourself up so many times.

Speaker 24 And one thing that you mentioned there that I so agree with and I think is so important is that

Speaker 24 you said you need to not care, or at least you need to not care too much.

Speaker 24 And there's this quote from Trump way back in the day that I would like to read to you that I think

Speaker 24 with all of his vices, I think this explains a lot of his success. And I'd like to get your reaction.

Speaker 24 So someone asked him, this is long before he was president, someone asked him, I'd like to know how you handle your stress.

Speaker 24 Trump responds, I try and tell myself it doesn't matter. Nothing matters.

Speaker 24 If you tell yourself it doesn't matter, like you do shows, you do this, you do that, and then you have earthquakes in India where people get killed. Honestly, it doesn't matter.

Speaker 24 Not the most eloquent individual, but I think he's hitting on something quite interesting there, which is through those ups and through those downs, you do need to take a step back and say, you know what?

Speaker 25 It doesn't matter. I don't often tell this story, but I'll share it with you.
So it's 2012. I'm working on the Romney campaign.
Trump and I have done two fundraisers together for Mitt Romney.

Speaker 25 And so I've been, you know, if you go to Trump's triplex apartment at Trump Tower, it looks like Louis XIV smoked crystal meth and then decorated the place, right?

Speaker 25 It's like a, you can't even believe this place. But we bought together a table for a charity, and it was tied to, I guess, lupus.
And it was downtown at Chipriani's. And I got to the table late.

Speaker 25 I had half the table. He had half the table.
And when I got there, I was very discouraged. And Trump looked over and and said, What the hell is the matter with you?

Speaker 25 And I said, Oh, this XYZ reporter just wrote terrible shit about me. I had a bad performance in my fund, and he's lighting me up.
And the fucking guy calls me a poppin' J.

Speaker 25 I don't even know what that fucking means. Okay.
I have to look it up even. It's a fucking terrible thing to be called.

Speaker 25 And Trump looks at me. And he said, what are you, a big baby? What did you just get your cherry popped? Are you a big baby? He said, and he's looking at me.

Speaker 25 He says, hey, listen to to me, grow a set of balls and shut the fuck up. It's literally how he's talking to me.
I have shit written about me every day. Do you think I give a shit?

Speaker 25 Learn not to give a shit. And it's literally what he says to me at the table while we're getting ready for the charity.

Speaker 25 And I walked out of there and I said, he's right. Listen, he's popular for a reason.

Speaker 25 I don't want to be president, okay, because I just think the way he's handling himself is not appropriate for that job. But he's popular for a reason because he's smart, he's intuitive,

Speaker 25 he does identify kernels of truth in things, whether it's immigration or

Speaker 25 the lack of manufacturing prowess for the United States. I can take you through the things that he does that are smart.

Speaker 25 I just don't, and I'm not, I'm not in love with the way he handles himself because I think it's not a great reflection on the country.

Speaker 25 You know, and also, also, we've built over 80 years this architecture around the world that we represent something to the rest of the world. And I'd like to maintain that.

Speaker 25 I'd like to maintain that beacon of hope, that candle of optimism. And I just don't think he's handling himself right.
But, but there were kernels of wisdom in what you just quoted.

Speaker 25 And there I was at this lupus fundraiser where Trump was telling me,

Speaker 25 get over yourself. Okay.
It's not that big of a deal that people are writing negative stuff about you.

Speaker 24 Exactly. And it seems like you have done a good job throughout your career.

Speaker 25 I haven't done a perfect job. And again, here's the thing.
You know, your grandmother may have told you, Ed, what other people think of you is none of your business.

Speaker 25 And you got to try to live by that. But if you're being brutally honest, there are days where you're impacted by what other people think of you.
And you have to work on that every day.

Speaker 25 You got to say, okay, forget that. Let me shut those notifications off or, okay, wow, that was a real nasty article about me.
Who cares? Let's move on.

Speaker 24 How do you do that, just practically speaking? Say, I mean, you're a public person. You've had people write things about you.
You've had failures and busy.

Speaker 24 I mean, you mentioned buying into FTX and then that blows up and then that's a problem. I mean, you've had these moments where, you know, things can get to you.

Speaker 24 And again, why I think you have incredible insight is the amount of times that you've come back. And with so much energy and with so much agility,

Speaker 25 what do you do? I think the number one thing, and it's a simplistic thing to say to you, but the number one thing is get up.

Speaker 25 The number one thing is no self-pity. Okay, the number one thing is manage your expectations to zero.
Okay, you're young enough to be one of my kids.

Speaker 25 So if you were one of my kids, I would tell you, curse all you want, but there are two words you can't use in my presence. I will flip out.
You want to hear the two words?

Speaker 25 Should

Speaker 25 and ought. I don't want to hear those words.
I should have gotten into that college. I ought to get a 36 on my ACT or whatever it is.
Should and ought are normative words.

Speaker 25 And ultimately, when you get down to it, they express some level of victimization. Okay, I should not have been fired from the White House.
Well, you know what? I was fired from the White House.

Speaker 25 The world is based on is

Speaker 25 and was,

Speaker 25 not should and ought. And so if you want to train yourself to get over things, deal with it.

Speaker 25 Don't be, you know, and also recognize there's a requisite package of things that you're coming into life with. You're going to have trials and tribulations.

Speaker 25 If I took you to an ancient Greek theater and it was 2200 BC, there would be two masks on the wall. One is a happy mask expressing comedy.
One is a sad mask expressing tragedy.

Speaker 25 And what the ancient Greeks would have told you, Ed, is that you're going to get both of those things in your life.

Speaker 25 It'll be moments where of levity, where you're laughing, and there's moments where people are dying around you that you're going to be saying goodbye to people that you love.

Speaker 25 And that is unfortunately the human condition. Both sides of that story are with you.
And every person, rich or poor, is going to unfortunately have to deal with that.

Speaker 25 And so get your mindset on the fact that that's going to be part of your life no matter what. And if you're an entrepreneur, You're going to have ups and downs.

Speaker 25 And they're going to be higher oscillations than someone that takes a corporate job or somebody that works in a law firm. But you know what? That's the choices that you took.
So don't be a baby.

Speaker 25 If I put a helmet on you right now, I said, you're going into the NFL, you're going to be a wide receiver, guess what's going to happen? You're going to get a concussion. It's like 100% guaranteed.

Speaker 25 Are you going to be a bitch and whine about the concussion? Okay, I went into American politics at the highest level and I got my ass kicked. What did you think was going to happen?

Speaker 25 You weren't going to get your ass kicked. You're going to play the victim? Don't play the victim.

Speaker 25 You with me? And I think that's the mindset. I think that's the way you got to think about these things.

Speaker 24 For any young people who are building their business, building their brand, what would be your number one piece of advice to those people?

Speaker 25 I mean, it's a simplistic piece of advice, but you should really listen to this and take it to heart. Read for three hours a day.

Speaker 25 Okay. Get yourself an audible app, get yourself a Kindle, put it on your phone.

Speaker 25 If you're walking to work, put your earbuds in and listen to a book and find things that interest you and read for three hours a day. Now, Buffett, Warren Buffett, reads for six hours a day.

Speaker 25 So you're not going to do that. I know that.
But you should read for three hours a day because if you read for three hours a day, you're going to learn stuff.

Speaker 25 You're going to learn stuff about management, stress management, history, health.

Speaker 25 You know, the reason why I do a podcast called Open Book, where I interview authors, authors, because I find authors have to work hard to develop a book.

Speaker 25 You know, before InflationEd, I used to say for $10

Speaker 25 and 10 hours of reading, you can get 10 years of an author's experience. It's $35 now, but you get the point that I'm making.
And so I've got books here that I read, you know, and

Speaker 25 I learn from these books. It could be a history book.
It could be a business book. It could be a health.
management book. It could be a book about quantum physics.
But let me tell you something.

Speaker 25 If you're reading three hours a day

Speaker 25 and you say how that's impossible, it isn't, because you can probably work out at least an hour, put the earbud in while you're working out.

Speaker 25 Okay, you're commuting, you're probably commuting to your job, you're flying on a plane once in a while, put the earbud in or bring a Kindle or

Speaker 25 bring your iPad and download the book.

Speaker 25 And if you do that, you're going to be a lot more interesting to people and you're going to be a lot smarter and you're going to be ahead of the game because most people are not doing that.

Speaker 25 Love that advice.

Speaker 24 Anthony Scaramucci is the founder and managing partner of Skybridge Capital.

Speaker 24 Anthony, love having you on the podcast. So much wisdom.
We really appreciate it.

Speaker 25 I appreciate you having me on. We got to do a home on a way.
You got to come on my podcast. All right, brother? I would love to.
All right, man. Good to see you.
Thank you, Anthony.

Speaker 24 This episode was produced by Claire Miller and Alison Weiss and engineered by Benjamin Spencer. Our associate producer is Dan Shallan.

Speaker 24 Thank you for listening to First Time Founders from the Vox Media Podcast Network. We'll see you next month with another founder story.

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Speaker 19 So, if you're serious about playing a part in the innovation economy, there's really only one bank for you: Silicon Valley Bank.

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