Anthony Scaramucci, this is so nice. This is a pleasure. I mean, I'm getting interviewed here, right? Is that right?
I know. You're actually getting interviewed. We're going to go. This is this, you know, the couch session for you. I actually think the first time you and I had a substantive conversation was when you interviewed me on my book on confidence.
And I remember thinking two things. One, that it was kind of interesting that I didn't ever expect you to be interested in that subject. So, I was intrigued that you would want to talk about that when I was thinking of you as talking about politics and business. But also that you'd actually read the goddamn book. I was impressed.
I gave The Confidence Code actually to my daughter. I thought it was a very good book about self-awareness as a woman. And also, you know, there's a balance, right? You're trying like if you were going to level a frame on a wall, there's a bubble. You're trying to get in there where you're confident, but you're not arrogant and you don't come across preachy or super serious or something like that.
We wrestled a lot with that actually when we were doing the research on confidence about whether basically it meant you had to be a jerk.
And that a lot of people obviously don't want to be and I think particularly a lot of women don't want to come across as the sort of Gordon Gekko type jerk. I mean, how real can we be? Because we could, let's be real, I think women have a much harder time than men with this topic because of socialization. And you can look at studies, Caddie. Young girls are doing great until they get to a certain age and then they're told that they have to behave a certain way. And young boys are told that they don't have to behave in that same way. And there's a, if you forgive me, there's a little bit of people pleasing that goes into that part of the culture. And there's a little bit of, you know, reticence. You have to hold yourself back in certain settings. And so I think it does impair people's ability to be who they really are, what they're capable of, you know, and it creates some anxiety, too, by the way, which I thought you just did a great job of explaining all that in your book.
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We came across this great quote when we were doing the book, which was if life was one long grade school, women would be the undisputed rulers of the world. And it's exactly what you hit on that women, girls do super well in the meritocracy environment of academia where you put your head down, you dot every i, you cross every t and you get an A grade, right? And we do very well in that environment. Then we get into the world of work and somehow the rules change on us and then we don't play so well and all of the jockeying that takes place and the politics of the work environment and the self-promotion that you have to do some of to get ahead I think we find comes less naturally to us.
Do you believe in masculine and feminine energy?
I thought you were going to say do I believe in star signs because I thought that's where we were going to go. I don't think I've 100% convinced you of that. That's a whole other podcast, a whole other topic. We can make that an agony maybe someday. But do you believe in masculine and feminine energy?
Yeah, I think I increasingly do. And I used to think when I was young that it was all, you know, BS. Not really BS, but I didn't want to believe that there was a difference. I think that was the thing. I didn't want to think there was any difference.
Yes. You see, I didn't know what to believe, but I think as I've gotten older and life has been humbling in so many different ways, but it's also been revealing in other ways. I think there is masculine and feminine energy. And it's not against the women's liberation movement to suggest that. I think you just have to accept that biologically, hormonally, we're set up a little bit differently. We're obviously should be treated equally and respected and so forth. But I think it's very important in the workplace to have men and women in the workplace. Because I think the perspectives particularly if the people have a mutuality of respect, you're getting a perspective that I think is necessary for both sides of the equation.
Okay, let's dive into your career. And by the way, this is probably very self-serving, but I think it makes our podcast work well because there's two types of energies going on at the same time.
I think it's not just energy. I think it's also experiences and lived experiences that everybody brings and you bring from your own experience. Okay, I want to dive into your career. You graduated from Harvard Law School, failed the bar exam twice, got hired by Goldman Sachs.
The only thing I have in common with John F. Kennedy Jr. But go ahead, keep going.
You're at Goldman Sachs after 18 months of the job. On February the 1st, 1991, you were fired from Goldman Sachs.
You could look it up. It's a Friday night. Yep.
You've said that that experience is seared into your memory. Now, what I want to do, Anthony, in this is you are very good today at making things sound easy. The trials that you've been through in retrospect. You've found a way to accommodate them and you almost seem to brush them off, but I want to go back to what it was like at that time because I think that's what's most useful for the audience.
So that's, you know, that's probably a hindsight thing. It's certainly not what was happening at the moment was extreme anxiety for me. You have to remember I was shooting so wildly in the dark and I think this is important for young people to recognize. You may see somebody at 60 confident but at 20 they probably didn't know what the hell they were doing, you know. And I've told people these stories. I'll share a couple of them. I had no idea what a lawyer did. I thought a Wall Street lawyer worked on Wall Street. I actually went down to Wall Street, Caddie, to get my first job as a paralegal because I thought that's where the Wall Street lawyers were. I didn't realize they were all over the city and that was just a characterization of them. I wore polyester because I went to discount men's wear places. I didn't know any better. My parents had no money. So when I had to go for a job interview, I was wearing polyester. I mean, I've gone from polyester to Brioni over the course of my career, but I started in poly. And I'm just going to tell you, I didn't even know better. Okay? And so the guy that hired me when he fired me at Goldman Sachs, he told me I was an experiment. And I said, 'What do you mean I was an experiment?' He goes, 'Well, you didn't fit in. You don't fit in. The only thing about you that fits in here is that you went to Harvard. Everything else about you doesn't fit in. You don't dress the part. You don't act the part. You don't talk the part. And you certainly don't have relationship transferability.' Meaning a lot of the people that got hired into the firm had fathers that worked on Wall Street or fathers were doctors. Fathers, you know, I had never seen the inside of a country club, Caddie, when I started at Goldman.
When you talk about that now, you wear it almost as a badge of honor that you didn't fit in and you didn't let that stop you. What did it feel like in the moment not to forget?
Well, it's interesting because I don't see it as a badge of honor as much as I see it as an objective observation of what happened. And I think I like talking about it because there are people out there that are in the middle class or you guys would say in England, working class. I want them to know that it's doable. I want them to know that they can find their way. There'll be in that rite of passage, there'll be wild amounts of self-consciousness and wild amounts of stupidity and failure, but they can find their way. And so, yeah, I talk about it not necessarily as a badge of honor, but almost as like, hey, man, this is how it went down. You know, Caddie, let me step back for a second. I could tell a very different story. I could say, hey, you know what? I had a really high IQ. I went to Tufts, Harvard, graded well in both places, went to Goldman, you know, the personnel director told me when I got fired, I never had to mention I got fired. They were so generous to me, they told me they could, they were going to mark me down as an interdepartmental transfer. So, I got fired on February 1st. I got rehired on March 28th, you know, 60 days later. And Tony Infante, who's now retired, was a lovely person, and she ran personnel. She said, 'Anthony, we're just going to mark you down as an interdepartmental transfer.' So, I could have hidden, I could have told you the following story. Ready? Blue collar, Tufts, Harvard, seven years at Goldman, Oscar Capital Management, entrepreneur of the year in the financial services category, 2011, Ernst & Young, and I could have given you all of these laurels. And then what happens is you become another caricature on Wall Street. And I've read more than one billionaire memoir and they're very self-congratulatory. And look at me, Caddie. They're up and to the right and everything went well and they kept climbing the ladder and it worked out. Yeah. And they're great and everything they did was perfect. And by the way, that really sucks for their children because you have beautiful children, many of which I've met. I have five children. If you don't expose your vulnerabilities and your humanness to your children and you've had the level of career success that I've had, and again, I don't have the career success of some of the mega billionaires on Wall Street, but I've had meaningful career success as an entrepreneur. It would cast a shadow over my children, right? So, it's almost worth being vulnerable and being expressive of the humanity of the whole thing gives the children more space. Caddie, I think it's easy for you and I to be vulnerable. And I talk a lot about the mistakes I've made and what it was like going through it because I do think that's the most helpful thing that we can give the people that are coming up behind us. But what did it feel like in the time? Because it can be so defining to have that kind of a career knock. How did it feel in the time? And how did you in that moment kind of get up the next morning and not hide?
I always say this to people, you got to use your sense of humor. You got to find the comedy in life. You know what I mean? It was brutal, Caddie. But let me tell you about because we're talking about confidence, okay? Real confident people, tell you the truth. Real confident people when they get canned or they get their ass kicked, they're like, 'Yeah, I got my ass kicked.' They don't code it over. They don't go like this like the scarecrow in the Wizard of Oz and blame other people. They're accountable for their actions. And real confident people, Caddie, they don't play the victim. They don't sit there and say, 'Oh, woe is me. Life is coming at me in the wrong way.' You know, when I got fired, the Gulf War had started. And that's the reason I got fired. We were going into a recession. They cut a third of the people. And I sucked at the job, by the way. And so, I was part of the lower third. And they fired me. And I said to the guy that fired me, I wish I had some Patriot missile systems to protect me from these Scuds that were coming into my little cubicle. And the guy laughed. The point is I didn't, I'm not, and the other thing is I don't want to be that guy where I have the woe is me tag on me, right? So all I said to the guy was I know you're going through a bad day too firing me. Could you do me a favor please and be a reference for me because I'm actually a good person, that I'm a hard worker. I just wasn't good at this job. There's going to be another job that I'm good at. Could you at least give me a reference on my character and my personality? But it was brutal, Caddie. And I had no money. And so I took a loan. The day I got fired, I was so nervous. Okay. I was 27 years old. I had no money. And I took a loan out from a Goldman Sachs investment banker. I paid him off, but I went to a guy that was in the division and I said, 'You know, I'm not sure if I'm going to be able to pay my school debt and my rent and stuff like that until I get on my feet. Would you lend me $5,000?' And he was so generous. He said, 'You know, I have a Dreyfus money market account. I'm getting 3%. I'm not going to charge you a loan rate. I'll charge whatever's in my Dreyfus money market account. I'm going to give you five grand. Pay me back that plus the 3% interest.' And it took me a year and I paid him back. But if you really want to know, I was panicked and I was up at night and I went to the bank. I got fired on a Friday. I went to the bank on a Saturday and I got four rolls of quarters. $40 worth of quarters. You say, 'Well, why would I do that?' Well, I was going back into Grand Central Station and there were no, I didn't have a cell phone. I couldn't afford a cell phone in 1991. I was using those quarters at payphones in the train station. I was putting quarters in and calling, 'Hello, Caddie. Hey, how are you? I lost my job at Goldman. I'm looking for a job. Do you know anybody that is in this place or that place or there's a job available here or a job available there?' And then finally someone called me and said, 'Hey, there's a job at Goldman on the 29th floor and it's a sales position in the investment research area. You would probably be really good at that.' And then I called my old boss. I said, 'Remember I said I need help?' And he said, 'Oh, you'd actually be good at that job.' And then I took a 40% pay cut, Caddie, to take that job. But it allowed me to stay at Goldman and it got me in an area that made me, you know, that I was really good at that job actually.
Did being at Goldman as a status symbol matter to you?
No. This is again so crazy. I mean, I went to law school because in 1985 I read an article that they were paying lawyers $65,000 a year, first year lawyers. My dad, my pops was making 32,000 a year. So I was like, 'Okay, that's more money than I could ever need. I'm going to go to law school.' I'd like to tell you, it was super analytical and strategic. It wasn't. When I took the job at Goldman, the lawyers were getting at that time, the prices were going up. The lawyers were getting $82,000 a year, up from the 65, but the Goldman Sachs starting salary for an associate investment banker was $110,000. So it was just about the money. It was. And you know what? If that makes me shallow to people and if that makes me superficial, so be it. I didn't have any money, Caddie. And I was like, okay, how am I going to pay off these loans? And plus, my parents, even at that time in my life, were relying on some level of supplemental income from me and I'm going for the money. So, if Lehman Brothers had paid more than Goldman, I probably would have gone to Lehman, you know. I wasn't, I mean, I don't know. I want, Caddie, you don't run your own business on Wall Street if you're status conscious. Okay? Because when you go to the cocktail party, you're running your own business, you know? I mean, I remember one of my buddies when I left Goldman, he was like, 'Well, how the hell are you going to go to these, what are you going to tell these people at these cocktail parties? You're working at what?' See, that's a statused person. I wasn't like that. I didn't give a... So then you start SkyBridge, your own firm. No, I started something called Oscar Capital Management. And so I left in '96. I had a partner. His name was Andrew Bozart. He's a terrific guy. If you took the B off of the first syllable of his name, Bozart, and the SC of my name, it was the worst name in financial services history. We called it Oscar Capital Management. It was so stupid. But anyway, we did very well. We had very good chemistry and we built a very nice business and right after 9/11 we sold the business to Neuberger Berman for a lot of money. It was a 9-figure sale and it was a differentiator in my life. It changed my entire life. And then I went to work at Neuberger. Neuberger got bought by Lehman and then in 2005 I left Lehman to start SkyBridge. And in 2008, the financial crash hits and SkyBridge almost went under. And you've spoken about what that moment of crisis was like because you didn't then have to be just your own job that you were worried about. You were managing clients and you were trying to keep your business afloat. How afraid were you and what did that fear feel like?
A lot of sleepless nights. I was convinced we were going out of business. I actually had two guys came to me and said to me, we were in this building but we were upstairs. I had a little tiny conference room and they were ex-Goldman partners and they both looked at me and said you should declare bankruptcy or fold up the business or close it down. And I said why is that? Well, your assets just went from 400 million to 200 million because of the crisis and the redemptions and you don't even have enough money to pay the staff. And I looked at them, I said, 'Yeah, we're not doing that.' And so I took no pay for that year, me personally. I had to trim up the staff, unfortunately. And then I had to figure out what to do. And so one of the first things I did was all the big banks were leaving the conference business, Caddie. And so I said, 'Okay, they're all leaving the conference business. Let's start a conference business because if I'm right, the conference business is going to return. If I'm wrong, it'll be like the farewell party on the Titanic. It'll be our last party.'
How did you keep your ego out of that failure? How did you, because I always have this, I've had plenty of failures in my career. And some of them have been quite public. And one of the things I learned is that you're not everybody else's headline. And there is a temptation to think when something goes wrong that it's all about you and everybody's talking about you. And actually, most people are way too busy with their own lives and their own problems to be thinking about your problem. But how did you manage that? How did you stop this being about you?
You are a dear friend and very generous to me, but I didn't manage it well. I wrote about it in my first book, Goodbye Gordon Gekko. I called it Davos envy. Okay. I was at the World Economic Forum at the invitation of Michael Dell and I was sitting in a room. I was 43 at the time. I think Mark Zuckerberg was 23. So we were separated by 20 years and $20 billion. And I remember talking about ego. I felt this small standing next to him. And I remember going back to that dodgy three-star hotel room which you've experienced in Davos and I've experienced and I remember sitting there in the hotel room and saying to myself, 'Oh wow, I'm not making it. I'm failing. I'm failing here.' And I remember getting a piece of paper out and I was writing down what was going wrong in the business. And then I said, 'Okay, let me flip the page and let me write down what could go right in the business.' And there's a term called pronoia. Have you heard of this term?
Okay. So if you look up the word pronoia, it is the opposite of paranoia. Okay. So pronoia means that the universe is bending towards you and that the people around you are helping you to succeed and that you find favor and faith in the universe. And I tell my kids and I'm going to tell your viewers and listeners, you want to be a pronoiac. You don't want to be a paranoid. That's a waste of time. Okay. And you've heard me joke around saying I'm too short to see the glass anything other than half full. When I look at the glass, it looks full. And so I made a decision.
Did you teach yourself that? Did you teach yourself to be a pronoiac? And how did you do it?
