How To Fail With Elizabeth Day - Anthony Scaramucci - My Biggest Failure? Working For Donald Trump

Episode Date: October 14, 2026

Scaramucci’s 11-day tenure as the White House Communications Chief under President Donald Trump’s first term ended in a blaze of recrimination. Scaramucci was advised by a PR consultant to disappear for five years. He refused - and reinvented his career. Now, he is the co-host of the US version of The Rest is Politics podcast alongside British journalist Katty Kay. After Harvard Law School, he joined Goldman Sachs and built a career in finance, eventually founding the investment firm SkyBridge Capital. In this revealing conversation we discuss what working on Wall Street in the 80s was like, getting fired from Goldman Sachs, his failed first marriage, not being there for his son’s birth, getting fired from The White House and rebuilding his current marriage. His book, All the Wrong Moves, looks at how three catastrophic decisions and years of ‘sh*tshow politics’ led to Trump. IN THIS EPISODE: 00:00 Introduction montage 03:22 Learning optimism and pronoia 05:02 Self forgiveness after failure 06:40 Growing up and getting to Tufts 11:58 Why he wrote the book 14:03 Fired then rehired at Goldman 25:23 Money mindset and marriage cracks 30:48 Work Taxes Burnout 31:26 Marriage Neglect Regrets 34:07 Conflict Avoidance Trap 34:55 Affair Self Forgiveness 37:46 Fatherhood After Divorce 40:44 Trump Ego Decision 45:00 Firing from The Whitehouse 57:03 Rebuilding and Looking Ahead 💬 QUOTES TO REMEMBER: When bad things happen, take a step back, and get into a channel that is the adult channel. Act in a rational way. I trained my brain to be optimistic. If you’re not careful, wealth can make you very depressed and lonely. Trump's bullying reminded me of my dad… but I was better prepared for it. 🔗 LINKS + MENTIONS: Anthony’s book, All the Wrong Moves, is available to buy now: www.penguin.co.uk/books/476667/all-the-wrong-moves-by-scaramucci-anthony/9781847929235 Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Bernie Sanders - swap.fm/l/pH8V6cBejDnhH47ega6D Andy Burnham - swap.fm/l/IpwatiJ5cM1h0UfcyFiA 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Anthony answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [e-mail] Learn more about your ad choices. Visit podcastchoices.com/adchoices

I was in a pretty abusive, domestic situation as a kid. I had done everything right to get the most coveted job, except I was not interested in the job, and I sucked at the job. When you say 80s on Wall Street, and I got there in the late 80s, early 90s, I'm thinking cocaine and booze. But go ahead. Let me take you through my day on the 31st of July, okay?

I am fired from the White House. I have missed the birth of my son. My wife has filed for divorce on me. I am torched and excoriated by the late-night comedians. This episode of How to Fail is brought to you by Ala Lacto-free. Hello and welcome to How to Fail with me, Elizabeth Day. This is the podcast that believes failure is the shadow twin to success. Before we get into this episode, please do remember to like, follow and subscribe so that you never miss a single episode.

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five oversized 12 by 12 samples for just $10 before committing. And Anesta's design team will help with sizing completely free of charge. Visit anester.com and order five samples for only $10 and you'll get $50 towards any rug of your choice. That's Anesta, E-R-N-E-S-T-A.com. My guest today is a Lamborghini driving financier, author and broadcaster who describes himself as an epic failure. And it's true that Anthony Scaramucci has never hidden his missteps from public view. Quite the opposite, in fact. His 11-day tenure as the White House Communications Chief under President Donald Trump's first term ended in a blaze of recruitment. discrimination. Scaramucci was advised by a PR consultant to disappear for five years. He refused

and reinvented his career. Now he is perhaps best known in this country for being the co-host of the US version of The Rest Is Politics Podcast alongside British journalist Cathy Kay. As a podcaster, Scaramucci has attracted a legion of new fans, many of whom see him not only is the rare Republican voice of reason in an increasingly fractious political landscape, but also as the thinking woman's crumpet. Scaramucci's paternal grandfather emigrated to the United States from Umbria in Italy. He had a working class upbringing in Long Island. His father was a construction worker, his mother, a makeup artist, and he was the first in his family to attend college, earning a BA in economics at Tufts University and later going on to study at Harvard Law School. From there, he joined

Goldman Sachs and built a career in finance, eventually founding the investment firm Skybridge Capital. His new book, All the Wrong Moves, examines how three catastrophic decisions and, as he puts it, years of shit show politics led to Trump. Scaramucci is particularly well placed to tell the story, as he says, I've gotten the living shit beaten out of me about three or four times, and I've been humbled by life. Anthony Scaramucci, welcome to how to fail. I mean, it's a pretty generous introduction. I feel generous when I think of you. Well, thank you.

You've got me through some tough times, most notably the last U.S. election. It's been a tough time. I mean, it's interesting, you know, it's a decade now where Trump has loomed over the political landscape. And weirdly, that four-year interregnum period made him more malicious, more malevolent. And sort of, he was like,

hey, man, I didn't steal enough in the first term. He had four years to figure out how to steal more. So it's been difficult. I mean, we got two plus years ago. You strike me as someone who is innately optimistic about life. Would that be fair? I'm too short to see the glass anything other than half full. I mean, just so everybody knows before this podcast started,

they told me to sit up. So I was trying to sit up. But my legs are dangling like the Shrek from, you know, the first prints in the Shrek movie. They're not dangling. But are you innately optimistic? Were you born like that? No, very much so.

No, I wasn't born like that. I think that's interesting. I come up from a family, a blue-collar pessimist. I find that like the neighborhood I grew up in, everybody, you know, everybody's decided that the universe is against them. And so you have to train yourself to think in the opposite direction. So actually, it's 35 years old now, but I read a book called Learned Optimism when I was in my early 20s. I was written by a psychologist by the name of Martin Seligman. And I remember I was in school and I said, okay, this is the antithesis of the way my family thinks.

I have to force myself to think in this optimistic way. And so I become an optimist through training. I didn't start out as an optimist. How interesting. And do you still have to practice it daily? No, now I don't. Now I don't have to practice. In fact, I talk to younger people about the word pro noia.

Do you know this word? Is it the opposite of paranoia? It is. Okay. P-R-O-N-O-I-A, you have to believe that about the universe. You have to believe that the universe is bending towards you in your life. When you do that, even when really bad things happen to you, you can see the bright side to it. Accepting failure, ladies and gentlemen.

Exactly. Yes. I mean, you know, it's fine. Well, it's part of what I really like and admire about you is that you are so open about failures being learning opportunities. Yeah, I mean, well, listen, you have two choices when you fail. You can slink away and hide. You can pretend that it didn't happen. You could lack accountability. You can play the victim. You can blame others. I mean, I can give you the whole list of things that you can do, which is, I think, the greatness of your podcast, because I think what you're trying to tell people, and it's really good in the UK culture for people to feel this way, it's okay to fail. There's no shame in it. Where the shame comes. in is if you're not honest with yourself, because what will end up happening is you'll dig yourself a hole that you can't get out of. You know, imagine if I had failed from the White House and then just slinked away and then was dreaded by that for the rest of my life, you know,

I mean, the coin of failure is tied to forgiveness. And so when you're flipping that coin and you see it land on failure, flip it over, you have to forgive your failures. If you don't do that, that's a mistake in life. Life's too short not to forgive your own failures. That's so profound. You just need to think about it that way, though, you know? Yeah. Remember, you know, if you grow up Christian, I was raised as the Roman Catholic.

They teach you about redemption and forgiveness, but how about forgiving yourself? Yeah. I don't walk around with a millstone of regret on my neck every morning. I don't kick myself in the pants every morning. I say, geez, I made a terrible decision to go work for Donald Trump. Let me kick myself in the pants this morning. You know, you've got to let that. go and you've got to focus on today and tomorrow.

Former classmates and teachers of yours remember you as being slick and popular. One former teacher was quoted in Vanity Fair saying he was always very political. He knew how to get things done with different groups. He was a very smooth character. Do you recognize that? I mean, that's probably the most. I mean, listen, I was a little bit of a renegade and a rogue in high school. So one of my teachers said that I would try to put a gallon of men.

water in a one-court bottle, which I guess he thought I only had one-quarter capacity, but it meant I would try to do too much in my life, which I've certainly tried to do that. I would say, in response to that, because I did read that, I would say I was definitely a character in high school, but I was a wayward character. I was hanging out. I was trying to socialize with women. I bought myself a used Camaro. I was sort of like an Italian Guido out cruising on Long Island, if we're really going to be honest, my role model was like Tony Minero from Saturday Night Live.

How bad is that, right? I mean, I had the gold chains. I had my hair slick back like John Travolta in the movie. I was believing too much of my own BS, you know. And I didn't get straightened out until my senior year in high school. When I look back on that, there was a gross period of immaturity, actually. What straightens you out? You know, my parents actually, you know, my father was like sort of like the strong, silent, working class type.

I mean, he was strict disciplinary. I mean, he used to beat the daylights out of us, but that was customary back in that day. But he was a loving guy and he wanted us to do well. He wanted us to go to college. He didn't have the money for the schools that I went to. And so I had gotten at a Tufts University, which I don't know if it's a well-known school here in the United Kingdom, but it was a, you know, it's probably like a top 25 private school in the U.S. And I had gotten into the state school, which is a good school, but it was up in Bingham, New York.

It was sort of a remote area. Tufts is like right in Boston next to Harvard University. And my guidance counselor went to see my father and my mother and Elizabeth, they were smoking cigarillos just to set the scene for you. And we had this little tiny circular table just right off the hallway kitchen. And my mother was pouring the espresso and it was coming out of this cast iron pot like motor oil. Okay, it's like 8 o'clock at night. They're smoking cigarillos and drinking espresso that is like six times the cavanation of anything you'd find at a Starbucks.

I mean, these people, I don't know how their hearts didn't explode. And Johns and Eddie in Italian spoke to my, it was actually a dialect of a couple. Italian, Southern dialect. They were all from that area. And he told my father, you got to have Anthony go to the private school, have him go to Tufts. My father thought it was spelled like T-O-U-G-H-S. He literally had no clue. But the very next day, he told me he was cashing in his life insurance policy from his union, and he gave me a $10,000 check. Probably two weeks later, he handed me the check. And he said, okay, you're going to go to Tufts. I don't really have the money for. I cashed in my life insurance, got the cash value for it to help you get started.

And I think that scared me straight. I thought that the love to do that and then the sacrifice and then the pressure, I was like, okay, I don't want to let my dad down. I got to make sure I study. So I like literally dropped the Camaro. I bought myself a Nissan Centro, which is like not a flashy car at all. And I went to school and I got very good grades at Tufts and good enough grades to get myself into Harvard Law School.

There could be no higher stakes in so many ways. Yeah, it paid off for my old man. He said, always tease him. He passed away in 2003. I was like, you know, that $10,000 cashier's check from your life insurance paid off for you. I used to tease him. 2023.

So did he see you launch this second half of your career as a podcaster? No. No. No. So I started the podcast in April of 24, but, you know, look, he got to see the ups and downs of my political career, the ups and downs of my. my Wall Street career. And, you know, for my parents, if to remember, the bar was low. I mean, all they wanted us to do was go to college. You know, I mean, the funny part about my mother is

my mother wanted me, be a lawyer. So I went to Harvard Law School, but I never practiced law. And she used to lie to her blue collar friends in the neighborhoods. I was in Rosano's Deli, ordering myself like a, you know, big salami sandwich. And I'm standing there next to Mrs. Kizzenza, who's my mother's best friend. And she's like, how is that, how was that law firm Goldman and Sacks. How was that law firm? I'm like, what? Your mother told me you're working as a lawyer at Goldman and Sacks.

I'm like, she did? She says, yes. I said, this is Kizenz. It's great. And I'm like, I call my mother. I'm like, why are you lying to your friends? I'm embarrassed for you that you're this investment banker. I don't even know what that is.

That's amazing. That's, you know, that was the neighborhood I grew up in. I mean, no one knew anything. They didn't know the difference between Goldman Sachs and you pick the law firm, you know. Before we get on to your failures, tell me why you wanted to write this book. First thing it came to mind for this book, and I had the idea for it a few years ago, but there are so many people. Like, I travel the country.

I do a lot of public speaking. This is even before the podcast. So, you know, from the notoriety of getting fired from the White House, public speeches, corporate speeches, how to build yourself back up. There was a lot of resilient speeches, different things like that. And when I would travel the country, I would. be astonished at the following rhetorical question, how did we get here? What happened to this country where we have this morose tribalism? We have this anger-based populism. What actually

happened to the country? And so this is a reflection on my 38-year Wall Street career. This is some input from my failure as a White House communications director from Donald Trump, but also my observation as a political fundraiser for three decades for the Republican Party. And then it's also a little bit about my upbringing because I did grow up in a blue-collar neighborhood where my parents had bought a house, thank God. They paid $16,000 for it in 1962. And we had a good upbringing. I would never dishonor my dad or my father's work ethic by telling I grew up poor, did not grow up poor.

But, you know, we had a tight budget and things were we had to be disciplined about what we were buying and things like that. So I have that perspective. And then I was able to go to Goldman Sachs and build some measure of wealth. And then I created a couple of successful hedge fund businesses. And so, you know, I reached a financial independence status, if you will. And so that class movement in the United States, I think, has given me a perspective on the country where I can tell you about the divide. I can tell you about the pain that's in the divide. And I can tell you how I think it happened and then what we could potentially do to fix it. Great answer. No notes. Let's get on to your failures. Your first failure is being fired from Goldman and Sacks, as your neighbor put

it, but fired from Goldman Sachs. Yeah. So it's not a law firm, by the way. It's actually a high profile investment bank. I mean, Mrs. Kisenza. I mean, I don't know why. My mother. I mean, my mother. I mean, come on. So you graduated from Harvard Law School. You never went into the law. You went straight into Goldman Sachs. I didn't. And so, I mean, I was one of my failures, actually, which wasn't one of the big three that we're going to mention here, but I failed the bar exam after law school. Like Kim Kardashian. Yeah. Yeah.

Well, like John of Kennedy Jr., too. I made me failed it a few times. But I failed the bar because I was going to Goldman, and this is how arrogant and how smug I was. I had never failed anything. I figured I didn't have to study for it. That test is actually designed for you have to study for it. And so I failed the bar coming out of law school out of Harvard law school, no less. And my mother was super upset about that.

And so I went back and took it and passed it, okay, to appease her. But also, I think it was another big message in my mind, you've got to be a finisher in life. So even though I didn't practice law, I went on to pass the bar. So that was a minor failure. And that was due to smugness and arrogance, frankly. and it was a bad, bad ideas all around. But anyway, we're back and field. But getting fired from Goldman, this is like the best and the worst story.

So I went to Goldman Sachs, Elizabeth, because it was the coolest job at the time. So just hear me out. I'm a 25-year-old, insecure kid from not even the Adder Burroughs of New York. I'm from working-class family on Long Island. I've gotten to Harvard Law School. So I've got to prove to people that I'm, the coolest. So how do you do that? Well, you got to get the coolest job. So what the coolest job was at that time was real estate investment banking because the real estate industry was super

hot and so was investment banking. So if you combine the two of those, that was the hottest job. It was the most coveted job from the Harvard Business School and from the Harvard Law School the year I graduated. So I was hell bent on getting that job. The problem with that was I absolutely sucked at that job. I was ill-suited for it. I had to be trained. I mean, I was able to convince the people to hire me. And I always tell younger people that you got to pick a job in life that you really like, that you're driven by, that you have passion for. Don't pick a job where you're trying to impress your friends or you're trying to grab onto some status or a totem of status, which is a false promise to yourself. So this is an important lesson in failure because

I had done everything right to get the most coveted job, except I was not interested in the job, and I sucked at the job. Okay, so I'm hired and start my work on the 14th of August, 1989, and on February 1st, 1991, you could look at it. It was a Friday night. I remember it like it was yesterday. My boss sat me down in his apartment in Greenwich Village, invited me over for a beer, and I went over to his house, have a beer and he fired me. And they were downsizing because of the Gulf War and they were in the beginning of a recession. And he said something to me, these were immortal words that are burnt into my

brains. I'll share them with you. He goes, you know, you're a great guy, you're a very hard worker, you're a disciplined guy. You absolutely suck at this job. Okay. You're just the wrong job for you. And so I'm firing you. I'm letting you go. And here's your $11,000 severance check. and we're going to give you one week in our career resources, a place to build a resume and make some phone calls and stuff like that, but you're fired. I don't know why, and I don't know how I did this at that moment,

but I said to him, I said, Mike, can I use you as a reference? I said, it's got to be hard for you to fire me. He had fired like 20 people that day. He looked exhausted,

and I think the last person he fired. It was 8 o'clock at night. And I said, I just, you know, you said I had a good work ethic and stuff like that. If I'm in the right job, can I call you for a reference? And he said, okay, absolutely no problem.

And he said as much. And so I went home and I was like, what am I going to do? I'm 27. I went to Harvard Law School. I've been fired from Goldman Sachs after 18 months. What am I going to do? I went to the bank. I got three rolls of quarters.

Why did I do that? Remember, this was before cell phones. And it was 25 cents to make a pay phone call. and I got three rolls of quarters and I was living outside of New York City. I took the train back into the city. It was in Grand Central Station, Elizabeth, and I was pumping quarters into pay phones to call people. I had a stack of resumes that I had printed out and I was going to go look for a job. And I got on the phone with somebody and he said to me, listen, there's a job at Goldman Sachs in the sales and trading area.

they've had a couple of people leave recently, you should try to get that job. So next phone call was to Mike Facitelli, the guy that fired me. I'm still very close friends with them, by the way. And I said, Michael, I said, there's a job on the 20th floor. I said, there's a job on the 29th floor.

I said, I think I'd be good at that job. He said, you know, I think you actually would be good at that job. He went up to see the partner in charge of that area. And then he called me and he said, okay, they're going to interview you tomorrow at XYZ time, and I got rehired into Goldman. Okay, so I got fired on February 1st. On March 26th, I got rehired into Goldman. And then the personnel department called me and they were like, hey, you know, we're going to mark you down as interdepartmental transfer. We're never going to have to tell anybody you got fired.

Can we get the $11,000 check back? I was like, actually, you can't. Actually, I've already spent it. You know, I spent it on some of my school debt. I bought some suits for these interviews. I said, you know, you can't get the money back. I said, no problem. You know, you can tell everybody in the world that I got fired.

I don't care. She was great, by the way. She marked me down as interdepartmental transfer anyway. She just retired from Goldman, actually, 40 years ago. She was in the personnel department. And you didn't burn bridges, which I think is a temptation sometimes if you feel. Oh, yeah. Well, the number one thing you do is you blame everybody else but yourself.

And then in the process of blaming everybody else, you burn all the bridges. That was Mike Vasateli's fault. I got fired, not me. I didn't do anything wrong. See what I mean? Yeah. But I don't know what it was. It was either instinct, I hadn't thought it out as carefully as I have today 30 years after my firing or 35 years after my firing.

But I definitely would implore people that when bad things are happening to you, take a step back, take a deep breath, and get into, to a channel inside your brain, okay, that is the adult channel. Okay, there's almost like, you know, like a psychotherapist who say a witness mind. The witness mind is when you step out of yourself and you're observing yourself as a third party and then start acting in a very rational way. Don't let your emotions run the program for you. What's your darkest characteristic? Well, I'm Italian.

I mean, so, I mean, you know what Italian Alzheimer's is? No. We forget everything but the grudges. I mean, you know, we could be very vindictive and very vengeful, you know. You know what I'm talking about. Come on. You've seen enough Godfather movies. We get super wickedly pissed, right?

You know, first of all, you have to understand those instincts and then you have to hit the override switch. Okay. And so you asked me something about being a pessimist. So I am an optimist today. I mean, I've trained my brain to be optimistic. I didn't start that way. any more than I started without having, you know, that, like, vengeance or anger-based vendetta

and all that sort of stuff. You got to, I'm not saying it doesn't exist, but you have to, like, do something transformational to overcome that and to make your responses at a higher human level. You know, that's lower-level thinking for a human being. Higher-level thinking is the process of forgiveness, forgiveness of others, forgiving yourself. and pushing yourself into a more sublime position as a human being. You're capable of doing it. Wall Street in the late 80s, early 90s.

What was it like? Lots of drugs, lots of drugs. Okay. Did you partake? I actually didn't, by the way. And thank God I didn't because I come from like a family of drug addicts and alcoholics. And so I'm, you know, again, gambling addicts, drug addicts and alcoholics. So I made a decision at a very early age to avoid.

all of that stuff because I wanted to move from where I was. I looked at my family situation and I said, okay, if I do what every single person in this family is doing, I'm going to end up like every single person in this family. So I got to switch it up. I've got to think about it creatively and think about it alternatively. So I actually didn't do it. But when you say 80s on Wall Street, and I got there in the late 80s, early 90s, I'm thinking cocaine and booze.

but go ahead. Sorry. No, I'm fascinating because one of my favorite novels of all time is Tom Wolves, the Bonfire Advantage. Yeah, it's very well written. Sherman McCoy. Yes. Yeah.

Is it accurate? Anti-hero. Well, I would say, like the Godfather, art imitates life and life imitates art. And so, like, the mobsters watched the Godfather, then they became like the mobsters and the Godfather who were observing the mobsters, who weren't in the Godfather, to create the mobsters.

I mean, I just said like a weird syllogism, but you get the point that I'm making. And so after the bonfire, the vanities came out, it became like an anti-hero novel, but people started to adopt the suspenders and the mannerisms of the people inside the book, you know, the social x-rays and the people getting super thin and all the different things started happening. Moreover, when Oliver Stone wrote and produced Wall Street, which was late 80s, I think Bonfire of the Vanity was like 86 or 87, Oliver's movie came out in December of 87, the anti-hero Gordon Gecko, Michael Douglas. I was in Wall Street, too. I had a role in Wall Street, too. I got close to Michael Douglas and Josh Brolin and Shia LaBuff. And Michael told me that Wall Streeters would come up to him in New York City restaurants and say, hey, you know, it's a because of you, I came to Wall Street and Michael would be thinking himself, you know, I was like

the insider trader bad guy that went to jail. Did you not remember that part of the movie? You know what I mean? Lunches for Wimps, famous line from Wall Street. Lunches for Wimps, all of the stuff that he said in that movie. Before we get onto your second failure, you have gone on to be incredibly successful in finance. Is it nice having lots of money? It's very nice to have money. There's no question about it. It's better than not having money, but also with money does come some level of responsibility. So again, I'm from a blue collar neighborhood. So I have family members that are not doing well. Okay, so if I have a family member that's been disabled because of hard labor,

well, I guess what I'm doing is I'm subsidizing their life. I want them to be okay. You know, I've paid for cars, health insurance, college tuition, master's degrees. You know, I've, because these are people that I grew up with. You know, my mentor is a guy named Bob Castro Gnano, and I acknowledge him in the book. And you may remember Ken Langone. I don't know if you would recognize the name, but if you're in New York, Kenny gave $200 million to NYU. It's now called the Langone Medical Center.

And then he gave like $2 billion to the endowment so that if you get into medical school there, you can go for free. So he's one of my elder statesman mentors. He just turned 90 last year. those two guys would say to me, and they would say to you, Elizabeth, hey, man, if you made it from a blue-collar neighborhood and a blue-collar family, help the people. Okay. And remember, the country does better when we put a hand out to reach up to somebody and pull them up. You follow what I'm saying? And so when you say, is it nice to have money? It is very nice to have money. I mean, I have like modest houses, but I do have houses. I don't have one house because I don't want to live in this gigantic house because I think there's a paradox to

wealth and I'm happy to explain that to you if you want my theory on it. But I love cars, because my uncle was, I grew up in a motorcycle shop and so we always had cars around. And so when I was a kid manifesting my life, I'm like, okay, if I ever get rich enough, I'm going to own a rolls. I'm going to own a Lambo. I mean, I'm a little bit of a Nouveau-Rish Italian. What the hell you want for me? I mean, that's what it is, right? But I don't live in these big fancy-pants houses because it's really bad for my kids. I want me. I'm a little bit. I want my kids to be able to cross the street, ring the doorbell next door, and go play with the other kids in a neighborhood. There's a paradox to the wealth. So if you become very wealthy and then

you got to show off your wealth, what are you going to do? You're going to buy a big mansion. Okay, that's great. Now you've got a 15 acre estate. Oh, that's great. Now your kids are sitting alone in the mansion. Oh, wait a minute. I'm super wealthy. Let me go fly around privately. Okay, now the kids don't see an airport. Oh, I go on the Disney cruise. You know, Caddy thinks I'm crazy. She hates Disney. By going to the digital, I'm my kids to socialize with these other kids

on the Disney cruise. You see what I mean? Yeah. If you're not careful, your wealth will make you very depressed and very lonely. It's almost like a, it's almost like a,

it's like a sociological trap. I don't know. Maybe it's God or the universe playing a trick on you. Okay, you wanted to get the wealth, and then the wealth becomes a Faustian bargain with the society

if you're not careful with it. So I try to use my money for charity and help, help people. I do have a couple of nice things. I'm not going to say that I don't because I do and I like nice things and it's convenient to have access to medical care and things like that. But I'm trying to help the people around me with it. No more Nissan cars. Oh, no more Nissan. I'm sorry. Nissan. We had a linguistic. Yeah, I'm sorry. We're separated by the common language.

One of the things I love about getting older is that I'm increasingly aware of how much life there still is to live. When I was younger, I thought you reached a certain age and instantly life would be a bit boring. I pictured sensible shoes and early bedtime and never being surprised by anything. But I believe the opposite can be true. Life just gets more exciting. I've reflected on this in a letter that I've written for myself to read in 20 years' time. Dear Elizabeth, at 67, I hope you're still curious. I hope you're still booking the trip before you've quite worked out how you're going to get there.

I hope there are places you've never been, people you've never met, and things you're slightly too old to be doing, but are doing anyway. I hope you swim in the sea and eat things you can't identify and that you've said yes to adventures simply because they sounded like fun. And I hope you've given yourself the freedom to do those things. Because the future isn't just something to worry about. It's something to look forward to. And that's what I like about thinking ahead financially.

It isn't really about the numbers. It's about giving your future self options. Vanguard's managed personal pension can help you start planning for that future with their experts managing your pension for you. So, Elizabeth, wherever you are in 2046, I hope you've packed a bag. And I hope you've left some room for the unexpected. Search Vanguard managed personal pension to find out more. When investing your capital is at risk, tax rules apply.

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Your second failure is your first marriage. Yeah. And my ex-wife would probably be mad at me for talking about it so publicly, but I did all the wrong things in my marriage, actually. And, you know, like this book is called All the Wrong Moose. If I was going to write a book about my shortcomings or my failures, it would have been a phone book. My first wife and I got married at 24. That was me, and she was 25 respect really. We met in college.

and we had a very good relationship in the beginning, but some of the problems that I had as a kid I brought into my marriage. And so what were those problems? Well, my dad was a very strict disciplinarian. I mean, he used to beat the daylights out of us. And he was a temperamental guy. And so you can replicate that, right? Psychologically, you can downward shift into that and you can become that, okay, which often does happen in situations where there's alcohol and there's other things going on in a family, or you can try not to do that, right? And so, but what you've got to be very careful of is you create this antipodal effect where you go to the other extreme.

Okay, so here are the self-narration. Okay, ready? Yes. I was in a pretty abusive, domestic situation as a kid. So therefore I am not going to be abusive and therefore I'm going to be a conflict avoider. And so therefore you and I are in a relationship and you're doing things that I don't like. I'm not going to tell you about them because I fear conflicts so much that I'm not going to be able to express to you what the things are that are going on that are wrong in the relationship for me. Yes.

Does that make sense? It makes so much sense. Okay. Okay. And so then what happens is you have this crazy job. So you mentioned the money, but you have to remember, the money for me came with ridiculous amounts of work and it came with W2 income. So what does that mean? Let's say if I made a million dollars, I live in the city and state of New York.

I'm getting taxed 52% of it. I get to keep 48% of the money. And so you have to work off of the 48% of the money in each year in succession. And so I was working around the clock when I started my own business, which is it's better if you can be successful in your own business. And I say, you'll make more money. But think about all the problems that you have in your business. And so now was I neglectful to my marriage in that process?

I 100% was. And it cost intimacy. It costs relatability. And then the conflict avoiding, which was a terrible part of my personality. And I would recommend to people, if you're in a problem situation in your marriage or things are not going right, you have to face the music with yourself first to figure out what it is, right? It's never 100 zero. I mean, people can pretend, you know, we got divorced.

She was 100% wrong and I was 100% right and it was 100% percent. We can pretend that, but it's never that. You know, there's culpability on both sides. And so I didn't face those demons in my personality, and I didn't face, how can I say this? You know, you have your nature. You're born a certain way. You're born a certain way. I'm born a certain way.

Then you have your nurture, and that's affecting your personality. It's affecting the operating system of how you think. and I was so concerned about conflict and the way I was treated as a kid that I was never going to do that to anybody. But then that puts you too far away from the base standard of what is appropriate to say. You know, Elizabeth, we have a relationship. Here's things that are going right in it. Here's the things are going wrong in it for me. And by the way, you may have some things like that too.

We love each other. Let's try to figure it out. I didn't do that. And so that is a big epic fail on my part. And I don't have anybody to blame other than myself. Our marriage ended up fizzling probably a decade before it actually ended. We were both Roman Catholic, so we didn't get a divorce right away because something about the church. We try to stay married, even though your marriage isn't working.

Someone will have to explain that one to me in a different life, but then the Catholic, you know, the sacrament of marriage. But we were better off apart than we were together, but the way we ended it is something I really regret because I didn't have the fortitude to handle it as directly as I am right now. But by the way, I will also say this. My second marriage almost ended in divorce as a result of my White House career. We'll get to that one. But I think the learning, the self-learning and the self-edification of what wrong in my first marriage help me resolve whatever things that were going wrong on my second marriage.

You're married once? Twice. Twice. You're married right now? Yes. Okay. Going back to the conflict avoidance, which is something I hugely relate to. Yeah.

And it definitely had a part to play in the failure of my first marriage, although it wasn't the entire part. But part of the reason I was conflict avoidance because I was scared. I was scared that if I stated something that I was making me unhappy, that it would elicit a degree of anger, whether that fear was logical or rational or not or whether it was inherited. How old were you when you got married the first time?

32. But we met when I was 29. And I don't think, partly because of the conflict avoidance, I became a people pleaser and I don't think I'd done the work on myself that I thought I had. And I was just trying to keep people happy.

And then I lost myself entirely. It's difficult as a conflict avoidant people pleaser to end a relationship, particularly a marriage. How did you end yours? foolishly, you know, very badly. You know, I ended up having an affair and the affair got exposed. And then there was probably some parental alienation, which I was upset about at the time,

but I understand it better now from my ex-wife's perspective. That's my fault. I have to own that. You know, that was not the right way to end a marriage. You know, I should have ended it differently. But I'm a human being. And by the way, a lot of that marriage. end that way. So then that's where the process has to begin, where you have to actually forgive yourself.

That is a pain point for me because you also have at younger stages of your life, or at least I'll speak for myself, I had a hard time with the self-awareness. Like the bad stuff that lurks in my personality that you've asked me to express, I was less willing to express that, right? I wanted to express only goody-two shoes and only a good guy, got my temper in check, not a, you know, I'm a conflict of order people-pleaser, but I'm a good guy. I want to show you my good side, none of my bad side. You see what I mean? I do. And that is immaturity, and that's also a lack of self-awareness. Okay, so the reason why we're relating to each other, and you express as in your writing, but you could not write about these characters of you yourself didn't have really

good self-awareness. Okay. And so you've developed that and you probably didn't have that at 29 when you got married or when you met the person, you got married at 32. You probably didn't have it. But you were willing to make yourself have it. And I think that's the message to your viewers and listeners. You have to force yourself out of the comfort box of whatever your insecurities are

that will keep you in your little comfort box. You're going to break out of that. Yes. You have to force yourself to feel the self- self-consciousness, the anxiety, you have to like all of a sudden have the awakening. Wait a minute. I just did something really stupid or really flawed. And I did something that I always tell myself I would never do.

I've acted in an immoral way when I'm trying to project pristine morality in the situation. Do you see what I'm saying? So well put. It's very hard to do. You have to do it. You have to do it because if you don't do it, then you're not going to grow to be the person that you really could be. And I think you also have to take the risk that you will be loved with all of your imperfections.

Because so often when we're projecting that idea of perfection, as you say, we're hiding or suppressing our shadow sides. And actually real love, real belonging is acceptance of those aspects. You had three kids together and you were married for over 20 years. So in many respects, it's such a successful relationship even though it ended. How are you as a father? I mean, you would have to ask my kids. I think the divorce was very bruising and very traumatizing to my kids. And I think if my kids were sitting on this couch,

hopefully they would be sitting up properly. But if they were sitting on this couch, they would say to you that I hurt them very badly through the divorce process and through my actions. If I had been more of a straight-up person a less of a conflict avoider, there probably would have been less pain in that divorce. I would also say to people that if they're listening and they're going through something like this, because one of my friends recently went through a divorce and I said, listen, there's no such

thing with children as quality time. There's only quantity time. You've got to spend as much time as humanly possible with your children. And the other thing I would say to you is that if you're trying and you have good intention, even if you've made mistakes as a father, which I have certainly made my share of mistakes, you'll win back your children, you know, because they'll come to you for guidance and they'll come to. And also, as they get older, you become more human to them, right? You know, they idolize you when they're young Elizabeth. They demonize you as they get to a certain age, and then they humanize you. Like, holy shit, my father's like me. You know, he's just an older version of me and he's going through this life and he's made his mistakes and, you know, I can't

really demonize him because he's, you know, he's human. Am I a good father? I'd like to think my kids think I'm a good father. I would say that I'm a flawed father. I think they would definitely say, man, this guy's a really good provider. He's helped us out. He's paid for our educations. He's got us going in career tracks that we all love. He's made sure that our housing and all this different stuff has been secured for us. And I would say something about my children, which I would say, I would I adore about them. The mandate from them and from their mother, by the way, the mandate from me and their mother was do something you really like.

I got enough money to help you out, so just do whatever you like. I've got one kid that went to Stanford Business School. He's in Venture Capital. My daughter is a singer. She was in concert with Andrea Buccelli last week, which I'm very proud of her. I was in Italy and she has a great relationship with Veronica and Andrea. And she's been, she played Christine for Andrew Lloyd-Weber and Faye. She did a tour for them in 2003.

She's been at the Tokyo Opera. She's got a great singing voice, and she wants to be a singer. And so, God bless. And my 27-year-old adult child is a young aspiring film director. His short film won the Dublin Film Festival last year and the Tokyo Film Festival. So they're doing things differently than me, but they're doing things that they like, and I admire that in them. Your third failure is your firing from the White House. Yeah, that was a big one.

Different kind of marriage. Tell us this story. Well, I mean, I think the biggest failure, the biggest, biggest failure of my life, it was the decision to go work for Donald Trump. And so there were so many things flawed about that decision. There were so many superficial things that I did upon hindsight and reflection to make that decision, but bar none. Now, would I know Elizabeth Day if I had not going to work for Donald Trump? Probably not.

That's the biggest success story. There you go. You see that girl? Right. So here I am. So the whole thing was worth it, you know. Now that I'm working for him in that environment and one of my mentors told me not to do it. He told me that you and Trump are completely different people.

It's one thing to work for him and volunteer for him on the campaign. You're a lifelong Republican and blah, but you should step away from him. Jab Bush, who I was very close to, who I'd work for before he left the race. And then I ended up joining Trump's campaign, don't do it. told me, do not do it. And so I didn't do that. And so this is a story of ego and this is a story of pride more than it's a story of anything else. And so if you go up in a blue collar neighborhood like me, you go to Tufts and Harvard, you work at Goldman, you build two successful hedge funds, you now have the opportunity to go work for the American president. Okay. And in your mind,

because you're so self-centered, you think you're going to help everybody by doing that, particularly the people that you grew up with. And so my wife really despised him. This is your second wife, my second wife. My second wife. Yep, she despised him. She knew stuff about him from her friends in the New York social community. And she was like, you can't go work for him.

You know, I mean, she really despises him. I mean, I always tease and say that she hates him. as much as Melania hates him because that's like that. Actually, I think I found one person to hates Trump more than Melania. That's like Mark Millie. General Millie hates Trump more than Melania, other than that, you know. So now Deirdre and I got in a bone of contention related to that, which we can talk about because it's part of the story, but I ignored all that.

So I was going to put our round peg in a square hole. I'm going to go work for the President of the United States because he's the President of the United States, and I'm going to go do that because it's ego-based, significance-based, all the stupid things that you would expect yourself not to do. And, you know, I read the Iliad, I read the Odyssey. I watched Matt Damon tie himself to the mass this summer as the sirens were screaming and, you know, seducing the sailors off the boat into the Carbdis, into the whirlpool. And they said, my God, there it is. It's right there from 3,000 years ago. Homer telling us about ourselves. Homer telling us about how we can be tempted by certain things. And if we don't manage our

pride and we don't manage our ego, it can force us into our own odyssey, right? It can force us into our own displacement. Despite reading it, Elizabeth, and despite thinking I was a know-it-all, I had to live it. I couldn't just read it and learn from it. I have to actually go and live it. So I went to go work for Donald Trump. I spent 11 faithful days in that administration. And I write about it in the book, the real reason why I got fired. I got a very nice note from somebody I sent that book to as a former cabinet member. And he wrote me a very nice note about like how honest the book was about what was going on at the time in the Trump administration. And there was a group of people inside the administration that were trying to contain the worst aspects of

the president's nefarious nature, which you don't have people like that in Trump, too. But when I got there, there was like a whole commotion going on. And I was like, okay, how am I going to help this situation? How am I going to fix it? I don't think I've ever told anybody this story. Can I tell you a quick story? Definitely when you prefaced it like that. Yeah, I've never told anybody's story.

So my first day on the job, Sean Spicer quits. I'm like, okay, that's great because now we don't have to fire him. Like my nickname for him was Liar Spice. Like all the spice girls have a nickname. His was like liar spice, right? So we had to get rid of him. And then Sarah became the press secretary. That was my idea with Trump.

And then Trump asked me to do the first press conference. So, of course, I did that. But I'm in the lobby of the West Wing. And H.R. McMaster is the National Security Advisor. And we have a lot of friends in common. And I had traveled to Afghanistan and Iraq on troop support missions with some of his other colleagues who were generals. And so now he brings me into his office. We have this long conversation, and he's getting me up to speed on some national security.

I had gotten my clearance, and so he's reading me into different things. And he says to me, listen, we're going to have a welcome to the West Wing party for you at my house. Okay, we're going to go to Fort Meade. It's overlooking the Jefferson Memorial. We're going to have this, like, awesome party for you, and I'm going to invite all the people from the West Wing. I said, okay, Gary, I said, what do you want to do that? He says August 1st. I said August 1st, it is.

I got my ass fired on July 31st, okay? So now McMaster, that callous bastard, he says to me, holy shit, you got fire. What am I going to do with the hot dogs in the keg of beer? I said, HR, we're going to have a farewell. Yes. We're going to have a farewell party. Okay. And I showed up at his house on August 1st, and Gary Cohen and Mnuchin, all my buds from the administration, showed up and we cooked hot dogs and drank beer overlooking the Jefferson Memorial.

So what are you going to do? Are you going to be a baby? Okay. I got my ass fired. We're not canceling the party. We just turned it into a farewell from the White House party. And you write in the book, it's so fascinating because you write about mistakes that you made. If you'd wanted to hold onto your job, you would have lied to the president, essentially.

One of the quote-unquote mistakes was that you were too honest with him or that you embarrassed him in front of other people because you were telling him the truth. Yeah, well, it had to do with the Russian sanctions bill. For some reason, he's jacked up about Vladimir Putin. So the House and the Senate had passed a sanctions bill related to election interference. This was July of 2017, and the president did not want to sign the bill. We had a conversation about it, and unfortunately, there were other people there. This was my mistake, actually. When I got fired, this is the other thing.

I never blamed anybody else about my firing. I got fired. I did, you serve at the leisure of the President of the United States. If you're not doing the job that he wants you to do, he has the right to fire you. Don't be a baby about it. And so I'm fully accountable for my firing. But I said something to him that got him pissed off, which I said that they can veto the bill. And he didn't really, he's like, I'm the president I say, they can't veto the bill.

Well, first of all, that's eighth grade social studies. Okay. But second of all, that's how it works. I said, they're going to embarrass you. They're going to go to Schumer, get the 17 votes they need to overturn the bill. and he told Jared, I embarrassed them. He told Jared, I embarrassed them in front of other people. I told him something that I should have told him in private.

He doesn't like, you know, he did this to other people. Like, you can't tell the president, you can't tell somebody like Trump the difference between a Shia and a Sunni. Number one, he doesn't know the difference, but he doesn't want other people to know that he doesn't know the difference. It doesn't want you, like he'll think he's got to put on his bully game to intimidate you. Okay, like, oh, you think you're a big shot that you know something that I don't know?

You follow what I'm saying? So he'll always go to intimidation and dress down somebody. Jared, you mentioned there as Jared Kushner, his son-in-law. I mean, I don't want to dishonor the reputation of your father, but you were talking to me about growing up in a conflict-ridden household. Were there aspects of Trump that reminded you that?

I'm at peace of what my dad did and everything. We can talk about. It's not a really dishonor. Who the hell knows what happened to him when he was a kid? Yeah. But Trump's bullying, did that take you back? So funny you say that. And, you know, he had elements of that type of style and that type of personality.

But I was better prepared for that. I think I had done a lot of work on myself. Like, I just got done talking about my marriage and the failure of my marriage. I was way less of a conflict devoider at age 53 than I was at 23. I remember I got fired nine years ago. I'm 62 now. I was 53. So I was more ready for Trump.

What took me off my game with him is the relationship I had with him during the campaign versus how it was in the White House. So again, people can be mad at me for working for him. Some of the Yorker said, well, he was always an asshole. And so you should have known he was an asshole. All that stuff aside, I had a pretty good rapport with him. God going to tell you that I was his friend because if you think you're Donald Trump's friend, you really have no self-awareness because he's a transactional person. you're not his friend. The minute he thinks he doesn't need you,

he'll run you over with the car. You know, he's like a Tony Soprano that way. So with me and him, we had a very good rapport. And one of his family members said to me that I reminded him of his dad, Fred Trump, in the sense that I made my own money. And I really, you're allowed to curse on this podcast?

Yes. Okay. So I basically say, I didn't give a shit, right? So he always said to his family members, I call Anthony because he gives it to me straight. He'd get on the phone. That's a stupid idea. But why is that a stupid idea?

And I would tell him. So now I'm in the White House and I was acting in that same way. He did not want that. He's the president of the United States and he wanted everybody cowtowing to him and everybody deeply subservient to him. You know, there was a really, really funny story. If you ever invite Paul Ryan on your podcast, I was with Christine Lagarde. I think she's the EC. We're in Davos.

I told this story. I said, I said, Paul, he's the former Speaker of the House. I said, Paul, I'm going to tell Christine Legarde this story, and you tell her if it's true or not. And he says, okay, go ahead. I said, well, we're at lunch with President Trump. And this happened on Tuesday. Elizabeth, I know because I was only there for one Tuesday, so I know it was a Tuesday. We're having lunch together.

And Trump is in an argument with Ryan, and he starts pushing his chest saying, you work for me. You work for me. And Paul Ryan looks at him and I don't work for you. I'm in a totally separate article of the Constitution. I mean, like, Trump didn't even understand the checks and balances in the Constitution, right? And Paul's like, yeah, well, that totally happened. So you have to understand it's now that Friday, and I'm telling him that, and he didn't want to hear it. And then he said, I embarrassed him.

And then I was told if I make it to Monday, I didn't get fired for the interview. To really understand Trump. This is an interview you gave to the New York. Yeah, yeah, yeah. It was really some funny shit in that. I said that Steve Bannon was committing auto fallacious in his office, although I said a little bit more graphically than that, but it was really fucking funny, right? No one gives a shit. Just quickly, do you still bear a grudge against that journalist? Because he's a fellow Italian.

So a grudge, I don't bear a grudge. And I never mention his name for a number of different reasons, but I don't bear a grudge. Like, I have no feelings for him one way or another. It's sort of for apathy towards him. But I thought he was a really bad guy. Okay, so it's okay to forgive him and move on and to forgive myself for having that conversation with him. But another thing for your viewers and listeners, if you've got bad people around you, jettison those people. Okay, you don't, they don't deserve your time.

They don't deserve your energy. They don't deserve your positivity. If they're bad people around, jettison those people. Build boundaries. It's totally acceptable to you. You don't have to be a people pleaser, as you were talking about. you build the people around you, the portfolio people that are going to lift you. And I tell my kids you're the weighted average of the five people that you hang out with the most.

So cut it out. So I don't talk about him. I never mention his name, but I have no grudge against him. I'm sort of apathetic to him. And so that's a good sign because, you know, a 20-year-old version of me, you know, from 40 years ago or even a 30-year-old version of me probably would have. It would have probably been more vindictive. You were saying you didn't get fired because of that interview. You got fired.

Look, if you know Trump's personality, he thought that shit was really funny. Okay, it didn't get fired for that. I got fired because I said something to him in front of a group of people that he didn't know, and he thought I was trying to embarrass him. And he fired me. That's fine. I mean, you know, General Kelly actually is the one of the fired me because Trump talking about conflict avoidant. Trump hates conflict.

And, you know, I mean, he's a total conflict avoider. he's a keyboard warrior. He'll call Gavin bad names like Governor Newsom on, you know, Twitter, but he does not go after Gavin face-to-face. He'll be super nice to him face-to-face. I want to come back to Trump in a minute, which is not a sentence I've ever said before, but I do. I want to talk about your second marriage to Deirdre and how she filed for divorce, literally, during this time. Yeah.

You miss the birth of your son because you were at some Boy Scouts convention in West Virginia, weren't you? I write about all that. Yes. Again, this is a very big message to your viewers and listeners, okay? Don't make your relationships in your life disposable. Like, if you really love somebody and you talk about the unconditionally of loving somebody, like you have to accept every part of the person's personality, the good, bad, and the ugly. We were having issues in our marriage.

Most of them were related to me and my ambition. Some of them were related to priorities related to me. And she's a very strong person. And she's like, hey, man, if this isn't what you want, let's get a divorce. Okay. And so she sent a message. She's got an Italian streak in her personality. She's, we can't go to like remediation or like marriage.

She's got to fire in the divorce decree right away. Okay, she serves me with divorce papers. And then I stupidly still go forward. She actually served me on July 7th. And I go to the White House on July 21st. So there's a lot of miscalculations in there. but now she's pregnant with James and he's due on August 8th but maybe the stress of the whole thing she's giving birth to him on the 24th of July which is a Monday and I am in West Virginia at the

Boy Scouts event with Donald Trump and he's given this big speech and I'm there and he's like me if you remember the speech it was like a disaster he was talking about all this kind of weird sexual innuendo and all the stupid shit and and me and Kellyanne Kahn were looking at each other go, how are we going to cover the, I mean, it's like a disaster. And then Deirdre gives a birth to James. I'm not there. Okay. Now, you have adversaries in politics that are on the opposing team, like labor and Tories, but then you have the internal strife of the people that want your job or they want to annihilate you due to jealousies and all this other stuff, right? You're a fiction writer, so you know that the truth is stranger than fiction, right? So there's a group of

people inside the White House hate my guts, like Wrights Prebis and those guys, they want to get the information to the tabloids that I've missed the birth of my son. Okay, but that's what happens in Washington, right? You've got to know that, right? So I'm now trying to figure this out with Deirdre, missed the birth of my son, complete disaster. I say the White House firing as a big failure, but I want to include the whole thing, including missing the birth of my son. And so now I've got to figure that out. I still love Deirdre. I'd like to stay married. I'm pretty sure she still loves me. And we have two beautiful young kids. Let's see if we can work it out. But I'm working at the White House. And so I've got all of these things going at the same time. Then I get abruptly fired.

Okay. So this is to your viewers and listeners. Guys, if you're ever having a bad day and it's not cancer, let me take you through my day on the 31st of July. Okay. I am fired from the White House. I have missed the birth of my son. My wife has filed for divorce on me. I am torched and excoriated by the late-night comedians. I mean, I'm, I mean, we've got animation going on. I'm Tony Soprano on the Potomac. I'm a Jersey short cast member.

I mean, they were saying shit about me. Some of it was actually really funny. Okay, I think Bill Hater on Saturday Live called me human cocaine. I was, I mean, some of the shit was funny. And I'm going through the whole thing. I'm getting lit up by the cable news pundits. And now I'm out of my ass and I've got to go back and try to figure out if I can fix my marriage, rebuild my business, and then I've got to face the music with the press in terms of who I am as a person. Because I tell something about politics, when they go after you and they create that ad hominem attack, they create a two-dimensional caricature of you.

Okay. Because if they want to discredit you, then they got to get in people's minds who you are in a very, very different. negative way, right? And so then you have the responsibility, if you choose to take it, to blow yourself back up. You got to create three dimensions again. But this is where you are, right? So that was my day on the 31st of July 2017. So I went and repaired my marriage. We're nine years later. We're still married. I think we're stronger than ever as a result of what we went through. I went and prepared my business, and then I made a decision, and even though I love Howard Bragman, he gave me bad advice, I always teased them about it, by the way.

I faced the music with the late-night comedians, the cable news, and all the different people. And then I went and, you know, built a pretty good speaking portfolio in the United States talking about these issues. And then Katty Kay came to me and said, hey, do you want to do this podcast? So that's a nine-year odyssey. to me meeting Elizabeth Day. Finally, finally. Is that real enough for you?

That's so real. It can't be realer than that, right? No, it's everything I would ever want a guest to say. Thank you. You've seen Trump up close. You have this hugely successful podcast. You've written what is destined to be another bestseller. I'm not going to word.

Let's hope. And how scared are you about this particular inflection point in our global history in terms of what Trump could do next? I'm scared. I'm not going to say that I'm not scared, but I maybe I'm also very optimistic. I feel like Trump has exposed something so gnarly about aspects of the American body politic that there's enough smart people in the room, men and women, looking around saying, okay, well, we can't have this. We can't have a morally object, morally corrupt president running the largest economy with the most powerful military. So we're going to have to figure out a way to reform this. And so I believe that.

And I believe that reform is coming. I don't like what the Democratic Party is doing. Like I would tell you, and I've said this openly on the podcast, that the best thing that Trump has going for them are the Democrats. I mean, they feel the two poor candidates against them. when they fielded a benign, mediocre candidate against them, that benign mediocre candidate beat them and beat him as a sitting president. So I'm worried about them because they're in disarray and they fight with each other. You know, Caddy Kay has a great line, which I'll share with you.

She says that Democrats fall in love and Republicans fall in line. You know, so if Ted Cruz's supporter votes for him in the primary and he loses Donald Trump, they vote for Donald Trump. Bernie Sanders' voters didn't vote for Hillary Clinton. You couldn't get the party consolidated around Kamala Harris. They either didn't show up in the polls, okay, or they tappily voted for her. And that's just not enough support. You got to get the whole party.

You got to get the coalition together the way Barack Obama did. You see what I mean? And they're fighting with each other. The alt-left in that party is fighting with the centrists in the party. But I hope they win, even though I'm a lifelong Republican, I hope they will. win because we need tremendous systemic reform. Anthony Scaramucci, I could speak to you for days on end. I've loved this so, so much.

It's a pleasure for me to speak to you as well. You know, I'm a huge fan of yours. You're a brilliant writer. Thank you. And you are also, you have the lantern on, Elizabeth. You're searching. You know, the podcast is great because you're really searching for people. And also you want people to be able to express their.

their fragility and their weaknesses in a way that in many ways strengthens them and makes them a better person. And it's very relatable. Well, thank you for seeing that and thank you for being not only an epic failure, but an epic guest. Thank you so much for coming on How to Fail. I hope you got as much out of this episode of How to Fail as I did. Brought to you by Arla Lacto-free, all the taste easier to digest. Please do follow How to Fail to get new episodes as they love. on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts,

please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.