From Wall Street to the White House & Back with Anthony Scaramucci & Kara Swisher

0:04Hello, I'm Anthony Scaramucci, and this is Open Book, where I talk with some of the brightest minds out there about everything surrounding the written word, from authors and historians to figures in entertainment, neuroscientists, political activists, and of course, Wall Street. Sorry, I can't resist. Before we get into today's episode, if you haven't already, please hit follow or subscribe wherever you get your podcasts and leave us a review. We all love a review, even the bad ones. I want to hear the parts you're enjoying or how we can do better. You know, I can roll with the punches, so let me know.

0:38Anyways, let's get to it.

0:47My new book, From Wall Street to the White House and Back, The Scaramucci Guide to Unbreakable Resilience, it came out this week. Look at that airbrush picture if you're watching on YouTube. It was very expensive to get the picture to look like that. And so today we're flipping over the mic and taking my place in the interview chair is the brilliant Kara Swisher. We're going to talk about what it's like to get fired from the White House, humiliated in the press, lit up like late night comedians, and then go into crypto and work with Sam Bankman-Fried and still be here to talk about it, although a lot shorter than I was when that started.

1:26In any event, Kara, she's a toughie. Listen in.

1:37Hi, this is Kara Swisher. I've taken over open book from Anthony Scaramucci and not a minute too soon. It's going to be such a much better podcast. It'll probably be bigger audience. Yeah, I'm taking over. That's correct. So we're going to hear to talk about your book. I'd love you to sort of give us and I just last night I interviewed Jen Psaki. So I'm into the political books right now. This isn't a political book. You've written about sort of your life in politics, but the title has that in it from the White House. So talk about what you were trying to do here. Well, I mean, the title of the book is Hold It Up.

2:10It's Wall Street from Wall Street to the White House and back. It's not necessarily a political book, but it's a come up in story. I got my ass kicked in the White House, thrown into Pennsylvania Avenue after 11 days, ridiculed by the press, attacked by Kara Swisher on Twitter. That was probably the most hurtful thing that happened to me. Oh, stop. Suck it up, Anthony. So there I was. How do you rebuild yourself? How do you come out of a hole like that? Right. So I think Jen Psaki's book, which is a great book on the bestseller list, is more political. It's very insightful. Well, it's about how to communicate.

2:46And it's a lot about her mistakes too. We did a live event in Washington. I admire Jen Psaki and she clearly lasted longer in her job than I did. She did. Yeah, so she's incredibly talented. But my book is about a lot of mistakes in decision making. My book is a lot about how you have to own those mistakes if you really want to develop as a human being. My book is about expressing that vulnerability and being comfortable with that. And also, you know, Carrie, you've got these beautiful children that you've been nice enough to show me pictures of over the years. And both of us are blessed with these beautiful children.

3:23and I think if you're a good parent or you're trying to be a good parent, you have to create this open space for your children to see your foibles. I have so many rich friends and you write about this in Burn Book, okay, which is another great book. I have so many rich friends that are trying to gloss over their lives. I've read biographies of billionaires where their life is going up in a 45 degree angle straight into the right. Everything's perfect and their kids are very stressed out by that because that's not how life really works. You know, life is a series of trials and errors and missteps and failure and setbacks and then coming back from them.

3:58And I wanted to write about it openly and in a revelatory way. You know, somebody hopefully would pick up the book and read it and it would make them feel better about whatever they're going through. And the flip side is for my children, I want them to also know, hey, you can have a very successful life, very full life. It doesn't have to be a perfect one. So the thing is, you don't open on the White House, you open on Bitcoin, which is, you know, I called you, I'm like, oh no, look at where you are. You had, you start with a lot of sort of failures, I guess, which, I mean, I know the whole trope in tech is, you know, I just haven't found the way to succeed.

4:32It doesn't mean I failed, but often it is failure that you have. And you talk about a number of them. The White House was obviously the most high profile one, you know, and you have different lessons from each of them, you know, finding joy, et cetera, and some things from your grandmother or grandparents and your family and your upbringing. But let's start about Bitcoin because that was something that you had really went all in on. You were close to Sam Bankman-Fried. Obviously, he's in prison for 25 years now. Bitcoin has gotten back to a number and it looks like they're returning their losses to the investors, largely because they made a couple of really good investments, such as Anthropic and things like that.

5:16Talk a little bit about why you started with Bitcoin rather than the White House. Well, I started Bitcoin. It was the first thing that was the most topical that happened. Boom. That's a 2022 episode. The White House was a 2017 episode already seven years ago. But I started with that because I made the mistake of liking Sam I made the mistake of trusting Sam. And we did a tremendous amount of due diligence. And I guess I'm alarmed by the fact that we weren't able to pick up. And by the way, it wasn't just us, Cara, as you know, there were 25 other venture capitalists, sovereign wealth funds that made the same mistake alongside of us.

5:57But I started there because it was very topical and I got bloodied in the press. I think Bloomberg, there was a journalist at Bloomberg that wrote my financial obituary. My fund was down 39%. Sam bought 30 % of my company. He was going to jail. This must be the end of Anthony Scaramucci. And that's fine. People are entitled to their opinion. And I'm a big supporter of the free press and people can write what they want. You had a New York Post thing. Explain that story of what you did there. The New York Post had you in a boat. Yeah. Look, I got it here. Look, these, because you got characters in my office.

6:31Okay. These are all characters, right? So the New York Post had a picture of me sinking in a Bitcoin boat. Of course, the captain of my office made a bobblehead of me. There's the SS Looch. And I'm going down in the Bitcoin boat. Bitcoin was at$17 ,000 at the time, down from$69 ,000. And the New York Post basically said, he's going down. And then Bloomberg jumped on that and said, yeah, this guy's really going down this time. He's the dummy of dummies. And he's made a big bet on Bitcoin that's wrong. But again, it may be right or wrong. It's more right today than wrong. Our fund from those negative articles has rallied over 200%.

7:11We had phenomenal performance last year. We have great performance thus far this year. I'm touching wood because maybe tomorrow will bring negative onslaught of market activity. I don't know. But I think that the messaging in my book is, you're a high profile person, bad things happen. You're going to get written about. You have to be able to be strong enough to deal with that. And we've stayed in our position. Now, since you mentioned Sam, I just want to bring up, yes, you're correct. Sam is going to get his - Well, he got his day in court. Now he's got his days in prison. He's going to get his, the money's coming back to the people that were in the fund.

7:47Sure. The great irony for Sam is he was a brilliant guy, but he was too smart for his own good. He did illegal things. He did commit fraud and he was found guilty of committing fraud. He's now trying to appeal it. I read Bill Colhane's article, I guess Bill went to go visit him in prison. I read that article last night and my reaction to the article was, Sam, own up to the mistake that you move client assets into your personal account. That's a no-no on Wall Street. You can't do that. I write about it in the book. If you're an ethical person with high integrity, which you happen to be, and I like to think of myself as somebody like that, there's always opportunity.

8:23I have got killed at the White House, but I was a good guy to a lot of people on Wall Street. They came to my aid to help me rebuild my business. I misstepped with Sam. I thought he was the Mark Zuckerberg of crypto. He was the Bernie Madoff of crypto. But a lot of people came to my aid and helped me with my business. And I think that's another big point in the book. Build good relationships. Be good to people. Bad things can happen. Good people will come to your aid. So what, you know, one of the things you start off the book of talking about, you know, mistakes, you also made a Goldman and not wearing the wrong suit, a polyester suit, when you first went there.

8:59Talk a little bit about how your early stuff, if made you sort of come up with these, I guess they're bromides or lessons that you're trying to pass along. Well, you know, listen, when you grow up the way we grew up, and I read your life story, you know, we're all growing up with different levels of trauma. But at the same time, we're trying to seek higher aspiration in America, right? We're both trying to live the American dream in our own way. And so for me, when I joined Goldman, I didn't know the way. What do I mean by that? I didn't have the right suits. I didn't have the right shirts. I didn't go to the right boarding school.

9:35I didn't come from the right upbringing. You look like this MOOC from, you know. I look like John Travolta in Saturday Night Fever coming into the, I mean, I had a partner at Goldman Sachs tell me, wow, you actually know what the TED spread is and you're 23 years old, but you are dressed like a Brooklyn undertaker. Okay. Right. And you're fully flammable in the goddamn interview. And he embarrassed me. I called my mother and you have an Italian mother. My mother was like, what is he talking about? You look fantastic. I'm like, no, I actually didn't look fantastic. And so I went and got myself a credit card and borrowed money to buy some natural fiber clothing.

10:10Yeah. This guy was very honest with me. He's like, hey, man, you are not coming down to Goldman Sachs dress like this. And, you know, I rewatched Saturday Night Fever the other night. OK. Oh, you did. I did. I had to rewatch it because I wanted to see what was going on. And it was like Italians yelling at each other at the kitchen table. Yeah. Windows driving around in the car, half drunk and stood on. And I was like, holy shit. I mean, I did grow up like that. Yeah. And now I'm here. That's a pretty big odyssey. That's a pretty big journey. Absolutely. You are Saturday Night Fever. You are. Except you're a bad dancer, I'm guessing.

10:46Are you a good dancer? No. I mean, is John Travolta a good dancer? There was a big overbite in the dancing of John Travolta. Okay. All right. I think he did okay. My wife happens to be a good dancer and was at a time a professional dancer. Yeah. As told me flat out, you suck at dancing. Okay. The only time that you're any good at dancing is when you're half drunk. That's the only time you can actually follow the beat. Yeah. And for some reason, you think John Travolta is a good dancer, but he's like got an overbite, the guy. All right. So you suck as a dancer. He sucked as a dancer. Oh, man. Tough audience.

11:18But at least I'm self-aware enough to know that I suck as a dancer. But when you were doing that, and you also said you made mistakes of trading and things like that, a lot of your story is about failing and then getting up again, right? A lot of it, it seemed like a lot of lessons centered around that. Here's the message. If I wrote down at age 15, I am going to start my own business someday and I'm going to make it on Wall Street and I'm going to be worth XYZ amount of money. I would have thought that would have been an easier way. I mean, I didn't do, I've got buddies of mine. They've spent 37 years at Goldman Sachs.

11:55They've become very rich and they've got great lives. But I did it in a totally different way. Right. I've had the opportunity to do things in life that I am very appreciative of. But it also came with because of the risk taking, it came with a lot of failure. And so the question is, how do you handle that? And I think I tried to write that in the book. How do you stay resilient in the face of stuff not going your way? Yeah. So tell me tell me some of the things that you want. And I want to get to the White House because it does have a through line, this book, like in terms of getting up and getting up and getting up, because, you know, any one of these, The Bitcoin thing, the White House, certainly, where you became a joke.

12:34You know what I mean? And the Bitcoin thing, a lot of people, you're right, were taken by that. But at the same time, the focus was on you and your mistakes. Well, listen, I mean, let's talk about Bitcoin first, then we'll go to the White House. Right. When you are getting slammed in the press and you are on Wall Street, people leave. They redeem. Mm-hmm. Okay. The flip side is - Meaning people take their money out of your fund. But if you stayed, you actually did incredibly well in our fund. But you know the press and I know the press. If it bleeds, it leads. Nobody has written the Skybridge recovery story.

13:17Right. I walked into a meet. I was out at the Milken events. This is the Milken conference, speaking of someone who recovered from - Yeah. Well, somebody said to me, I thought you were insolvent. You're still at Skybridge? I said, yeah, excuse me? Well, I thought you were insolvent. Didn't they write a story about you that you were going out of business? And I laughed. I said, well, they wrote that story, but they didn't write the recovery story. You see? And so the point is, you can't be upset about that. You don't take that personally. You keep moving. The ridicule stuff is more interesting, right?

13:46When Bill Maher, who's actually become a friend, and I saw you on his show recently. Bill Maher, I think he called me Tony Soprano on the Potomac. I think he called me a Jersey Shore cast member. I think those were the easier comments. Jack Oliver, I mean, I don't know. It was like a 28-minute, it was in a food processor for 28 minutes. And so, yeah, when you are getting ridiculed and getting your ass handed to you like that, you could do two things. You could do what these professional crisis management people tell you to do, crawl into the corner, don't talk to anybody for six months, go into like a Bermuda Triangle, or you can hit it head on.

14:23And I made the decision to go on Kimmel, Steve Colbert, Bill Maher, and talk about the situation because you want to add dimension, Kara. When bad things are going on, you want to add dimension. You don't want to have somebody else control your narrative completely. And by the way, a lot of things that happened were true. I never said to anybody, oh, I got fired from the White House. It was somebody else's fault. Let me be the scarecrow and the Wizard of Oz. I said, no, I effed up at the White House. I made certain decisions strategically that were wrong. I got fired. I never brained President Trump or Chief of Staff Kelly for my firing.

15:00I owned my firing. But the flip side is I'm not going to let that episode of my life define my entire life. You know, I don't wake up in the morning and say, wow, I made mistakes at the White House. Let me wear this millstone of regret for the rest of my life. Let me kick myself in the pants this morning. Made mistakes at the White House. Well, you have that. You have an appendix in your book. Fire, don't worry. It happens the best of us, meaning me. and you're dumped, yikes, sorry about that, you're going to be fine, publicly shamed, boy, you've come to the right place, made to feel stupid, keep your chin up and read Lesson 23, punched in the face, promote it.

15:33Promote it as the last one, but that's like a lot of like getting beat up kind of metaphor. I mean, not metaphors, actually getting beaten up. You're also in a world of tremendous social media exposure. And we have young kids. And so we also know that these young kids have pressure on them. They can get cyber bullied. They can feel exposed and self-conscious. And so the lessons in this book are relax, don't feel exposed or self-conscious. Just enjoy your life. Care a little less about what other people think. Well, that's obviously what you've done. I want to get to the way in a second, but one of the people you quote a lot is Marcus Aurelius's meditations, which seems to carry through the book, I was surprised.

16:13I actually love Marcus Aurelius. Talk a little bit about that. You give book recommendations. Why were you surprised? I don't know, Anthony. I wasn't thinking of you and Marcus Aurelius. I just wasn't. I don't mean to think you're stupid, but it was not the, he's a little different than you are. Here's the thing. When you grow up like Tony Manero in Saturday Night Live, if you have a high IQ and end up at Harvard Law School, you're still thought of as Tony Manero. Yeah. Yeah. Right? But I read meditations once a year in January. My birthday's in January and I read it once a year because I think the emperor's advice is about as sound as any advice from the ancient world.

16:53Moreover, we do know that the monks did change a lot of the text of the ancient world. And so some of this is actually Christian thought in the eight or nine hundreds that are in the books like Marcus Aurelius or even Homer's books, or even some of the texts that we think is from 3 ,000 years ago, these monks, they changed it and they altered some of it. But this is about controlling your mindset. This is about recognizing that you are experiencing death every day. The five-year-old version of Kara Swisher is long gone. You may have a memory of that person, but that person's not here anymore, nor is the five-year-old version of me.

17:32And his point is that you're changing every day in memento more, Latin for in this hour, this moment I can die, a result of which take yourself a little bit less seriously, or the immortal words of Mel Brooks, relax, none of us are getting out of your life, right? So these are stoic concepts. These are concepts that if you bring them with you in your life, you can accept life more easily. You know, the Italians, my cousins that live in Italy, they really hurt my feelings. One day they told me I was an Italian. I grew up and I identified as an Italian. And they say, you're not Italian. I said, what do you mean I'm not Italian?

18:09You're American. I said, what do you mean? Well, you work like a nut. Okay. We had our empire. The Italians know they're going to die. They drink an extra bottle of wine. They take a nap in the afternoon. They slice an extra piece of cheese. Okay. But the Americans, we think we're going to live forever. We're walking around in our empire. We're in the museum of our empire. We know we're going to die. And the minute that you switch your mindset and you take in that information, you're happier. You know, I got fired from the White House. I flew to Italy. I had a flat - That's a good place to go.

18:40Yeah. I had a bottle of red wine and I had a delicious pizza somewhere in Rome. And I looked out at the people and I said, this is not so bad. You know, we live in life. Yeah. So let's talk. We've only have a little bit of time, but talk about that. Like you said, it's seven years ago, like seven or more, right? More than that. No, it's seven years. It'll be seven years, July. Yeah. So it goes with you. It's never going to leave you, right? This is never going to leave you. Although now, given where Trump is, you look like the good guy, I guess. I'm neither the good or the bad guy. I'm just one of the guys.

19:14I think that when I got fired, it was a big deal. Then 80 other people got fired. And now there are 40 people that work for him, including the vice president. that has said, you got to keep this guy as far away from the White House as possible. So I think a lot of the things that I have said are truthful. You see, the reason why you get in trouble is you're a truth teller, okay? And if you didn't ask me this question, but I'm going to answer it. Who's the most important fictional literary figure in the history of the world? My answer is Cassandra. And who was Cassandra? Cassandra was Priam's daughter.

19:51She lived in Troy. She was blessed by Athena with the gift of premonition, but she was also cursed by Athena that no one would believe her. And she told Priam that there would be death and destruction in Troy if you accepted Helen. Paris is bringing Helen here. They're going to launch a thousand ships. They're going to destroy this city. And Homer was trying to teach us something with the metaphor of Cassandra that truth tellers are not listened to. They are brushed off. People get pissed off. You tell the truth about somebody, Elon Musk mad at you because you told them the truth. Or Jack Nicholson and A Few Good Men, you can't handle the truth.

20:33So Homer from the ancient world through Cassandra is saying, hey, we're not good with the truth because we have to live in some level of denialism about our lives. And so I would prefer to be Cassandra. And the reason why you and I get along is that you like telling the truth. I like telling the truth and people don't like hearing the truth. And so they'll disfigure you or malign you. They'll disfigure me or malign me, but so on. You know, we have to get used to the truth. The truth will make us better as a society. Right. So when you're thinking about that, one of the things you have a lot of, what was the truth you learned from that?

21:10What's the truth you tell yourself? And then we've got to go in a few minutes, but I'd love to know you have so many different lessons. Be fearless, have a healthy mindset, be secure, find your style. My favorite is be tough, nice, actually, which of course I would like that. You got to be nice to people, but you also got to tell them the truth. You got to be tough on them as employees if you want them to do better, but you got to be nice to them. You can't be an arrogant asshole. You and I have met so many rich, arrogant assholes. I'm just not going to be that person ever under any certain instances.

21:40But you asked me about the White House, what I learned is that that is an executive role and you need somebody in that job that has very good executive management skills, meaning they can delegate, they can create a process. There are 19 cabinet and subcabinet divisions. You can't have somebody in that job that's going to cross everybody and immobilize the executive branch, the 5 ,000 people that are employed by the executive branch of the government. And what I also learned, I think is really important is that the problems that we're facing are ginormous. They're ginormous problems. There are problems of terrorism, mismanagement of the economy.

22:20There's problems associated with the way lobbying gets done in this country, right? We got planes falling out of the sky, food that's making us fat because we've allowed people to over-lobby the Congress and they get laws passed that are favorable to big food, which leads to better preservation on the shelf, but fatter people and less healthy people. We're pushing things through big pharma in a drug way where we're going to test the shit and we're giving it to people. We're making them feel bad if they take it or they don't take it. And look at what happened with Boeing. Boeing is, I don't know.

22:54I mean, these people, these whistleblowers died, Cara. You have to tell me how they died. I'm not exactly sure. Let's not start conspiracy. We don't know. I'm not starting conspiracy there, but this is obvious. You're starting in Seattle. You moved the corporate office to Chicago. It's not close enough to Washington because you're feeding out of the Pentagon trowel. So you moved to Virginia. How about making the products instead of sitting there with the corporate welfare? And so that's what I learned in Washington. It's not a swamp, Kara. It's a gold-plated hot tub. It's a gold-plated hot tub.