CRAIG

Hello, and welcome to the new series of Desperately Seeking Wisdom with me, Craig Oliver. This is a podcast for anyone who wants to lead a wiser, more fulfilled life, but is tired of all the snake oil and dubious life hacks that are out there. I talk to some well known people and some experts about what life has taught them, and they share the wisdom they've gained, particularly during tougher times. Today's guest is Anthony Scaramucci, a successful businessman and broadcaster before becoming Donald Trump's Director of Comms. He was fired after just 11 days in the job.

ANTHONY

You're on the playing field at the highest level of American politics and global politics, you make a mistake, you're in a free country with a free press, you get excoriated for that, anybody that says it doesn't hurt is lying to you. But I have a thick skin. I got fired. Let's move on.

CRAIG

When I first met him, I expected him to live up to his reputation as the ‘Mooch’, as he's known, the fast talking loud-mouth New Yorker. But I discovered he was a deeply thoughtful man who learned a lot about what really matters when his life came so spectacularly off the rails. So buckle up for some direct New York-talking and some penetrating insights from life and politics. So how are you Anthony?

ANTHONY

I'm pretty good Craig, how are you?

CRAIG

I'm very good. Look, I don't want to make this all about Donald Trump. I want this to be about you and all the things that you've learned. But I think we're probably just gonna have to start there. When Donald Trump came on to the international scene, I think a lot of people looked at him and thought, this guy's narcissistic, you know, he treats disabled people badly, he treats women badly, he says some things that are racist. And they thought, you know, he's not a great guy. I mean, what were you thinking when you went to work for him?

ANTHONY

Why did I say yes? Well, number one, I'm a life-long Republican. I've been a Republican Party fundraiser since 1989. I've worked on a number of different presidential campaigns. And I wanted to be loyal to the party. Number two, I was doing everything that everyone else was doing on that campaign, if they're really being brutally honest with themselves. I was morally equivocating Trump's behaviour. Now why was I doing that? I was doing that because unfortunately, in the United States, you only have two choices for President, you have the Democratic choice and the Republican choice: I was a lifelong Republican. And so despite his behaviour, I was equivocating, morally, and I was saying, let me hold my nose and let me support him anyway. I think I contributed, I was one of the accomplices to the ginning up of the hatred, the racial tension, all the things that Mr. Trump was capable of doing as President. I feel very bad about that and I've apologised for it publicly, I've done that on national television in the United States. And the other thing I tried to do, and thank God, it was successful, I campaigned against him, and I spoke out against him, and I did everything I could to help defeat him in 2020.

CRAIG

I mean, because when I've read about you, and I've looked into you, you're a guy who believes, you know, you're fiscally conservative and very socially liberal. And I just want to understand the psychology of that, I guess when the most powerful person on Earth comes calling, it's quite easy to kind of retrofit your arguments and your ideas, because it's quite flattering, right?

ANTHONY

I’m probably not that socially liberal. Just again, I want to talk very candidly, I'm a Roman Catholic. And so I understand where the Pope's position is on abortion, but that's my religion. Okay, I believe there's a separation of church and state in the United States, okay, so I don't want to impose my religious beliefs on you, Craig, or any other person. So the definition of pro choice is I'm choosing one thing, you're choosing another thing, I hope you respect my choice due to my religion, I do believe in a woman's right to choose. And I do believe in a marriage equality act for people that have different sexual orientation than me, if you really understand the doctrine of libertarianism, that's conservatism to me. The hypocrisy of conservatism today is they want to impose their values on you. That's not individual liberty, that's not standing for individual rights. So I just want to clarify that because I think it's an important clarification, but for me, very simply, I made a mistake. I own the mistake.

CRAIG

Sure.

ANTHONY

This was ego-driven, okay? So in some ways, it's worse than what you're saying, okay, you're almost giving me an out. This was ego-driven. I grew up in a blue-collar family, okay, these were not educated people. My mother had the map as she wanted to take me to Hartford, Connecticut on Labour Day weekend, and I said, no Ma, it's Harvard Law School. Why the hell would they call it Hartford if it's not in Hartford? Okay, so that's a joke in my family, she's 85 years old today, we still joke with her about it. So I will tell you that I was sheltered, blue-collar, naive person, lot of eye-opening things happened to me, I went to go work for Goldman Sachs. I built a successful hedge fund. I did a lot of different things. And so I got the chance to work on the campaign, thought the guy was going to lose - he wins. I never, I don't think I've ever told this story before, but I'll share it with you. ‘Do you want to come work with me?’ No, I don't. ‘Why don't you?’ Well, I have a great business, and I have a television show. Mr. President-Elect, I appreciate the opportunity. I don't want to go work for you. And then he named me to the executive transition team without telling me. So literally, I'm sitting on the couch on Fox and Friends - the morning show - he named me the White House Executive Transition Committee Chair, whatever it was, they were a 16-person committee, and the Fox and Friends guy turns to me, ‘so how do you feel about being put on the committee?’ I was like, why, what, excuse me? Well, the President-Elect just announced this. And so to make a long story short, I called him, I said, Mr. President, what are you doing? I told you I didn't want to work for you. Oh, ha, ha, ha, I'm the President-Elect. I'm your President now, you're going to do what I say, I need your help, blah, blah. Okay. And then something very egotistically damaging happened, let me explain that quickly. Never explained it before. Now, I had my ego invested in it, correct? And so that is a very big, damaging mistake. The ancient greeks’ [ancient greek] my pride and my ego will be my enemy, it will lead to my downfall. So that's what I did. He called me, and I went to go work for him. My wife said, don't do it, you're crazy. She filed for divorce on me. You just met her before the podcast started, thank God, we were able to reconcile. It was brutal. I went to go work for him. I did the White House press conference. And I went to work on getting Priebus and Bannon fired. And by the way, I got my ass fired too, but they were also out of that White House in the same week.

CRAIG

So just painting the picture for a lot of people who maybe don't know it in as much detail as: you famously became Director of Communications and you lasted as you said in that job, 11 days, and you were fired after a New Yorker reporter printed a conversation you'd had with him. Tell us about what you said in there, and what happened subsequently.

ANTHONY

But I think there needs to be more context, the reporter’s family, he's an Italian - American from the area I grew up in. His father Frank was very close to my dad, they worked in the same construction industry together for 50 years. So the families were like this, and I had a relationship with the reporter. And so I said a regrettable remark about Steve Bannon, it's probably not appropriate for your podcast, if you want me to share it, I will-

CRAIG

It’s also anatomically impossible I think.

ANTHONY

Yeah. But anyway, I said that about Bannon. And it was a joke. It was a flippant remark that I would have said to a school friend, somebody at a pub, having a beer, and I thought of this man like that, because we had a multiple decade relationship. And our parents went back 50 years. But I technically did not say this was off the record. And so he recorded me. And then he ran with a recordation to CNN to play it on the national airways. And so when that happened, and this is the truth, you can believe it or not, but knowing Trump's personality, you probably do believe it, he laughed. He thought it was really funny. He called me to tell me how funny he thought it was, okay? Why I got fired - the paper reported I got fired for the remark I made about Steve Bannon. Maybe that was part of it, but I got fired because Mr. Trump did not like the attention I was getting. Anybody that rises and gets spotlight in the Trump administration got shot at killed and - Pompeo had a great line once, he said Mooch, if he tells you, what are you President Pompeo, or he says to you, hey, you're getting as famous as I am, it's time to like book a trip to Antarctica and try to do a diplomatic envoy with the penguins. So when I was on the air, a couple of days after I got fired, which was my fault, I own the mistake, I'm totally accountable for the firing. I don't blame Mr. Trump. I blame myself, I made a mistake with the reporter. I got fired. Let's move on. In life, you can't be a baby or have a pity party for yourself.

CRAIG

So I wrote down something that you said about it afterwards, was saying that in that moment, my entire life became a car sliding down an icy hill sideways. I could turn the steering wheel as much as I wanted, but the car was still going to go where it wanted to go. Can you describe that moment of sense of being out of control and realising that everything was blowing up around you?

ANTHONY

Yes, I can tell you that it was completely out of control. I can tell you that I, you know, I was getting hit from all sides, okay, so if your viewers or listeners are ever having a bad day, they should call me, I'll make them feel better. July 31 2017, you know, I mean, it's super bad day, now not a health thing, thank God, but it was blasting, blasting to my reputation. They threw me out the front door, shot me into Pennsylvania Avenue, rolled me in margarita salt, I got lambasted on every cable news network, I got destroyed by every late night comedian, I got lit up and impersonated on Saturday Night Live. And I would say that every political pundit in America wrote something nasty about me.

CRAIG

And I think that's something that people who are in politics know is, in that moment, when something bad happens to somebody in politics, it's almost as if they're not a human being. So I was looking at some of the press coverage around it. I mean, one of them I thought was quite funny, which was Adios Moochacho playing on your nickname the Mooch, but it hurts, right? And it's painful. And they're not necessarily seeing you as a human being that's got things going on in his life and that kind of thing.

ANTHONY

Anybody that says it doesn't hurt is lying to you, okay, it hurts Barack Obama, David Cameron, it hurts Boris Johnson, But I have a thick skin. And those political figures also have a thick skin, so I can take the punch. You have to be a big boy or big girl about these things. If I'm playing American football, and I put the helmet on and I'm trying to catch a pass from Tom Brady, and I get hit over the secondary and get a concussion, I can't then wake up and say, oh, woe is me, I got a concussion. I can't do that. You're on the playing field, at the highest level of American politics and global politics, you make a mistake, you're in a free country with a free press, you get excoriated for that, you own the mistake. So in other words, yes, it's hurtful. You know, my grandmother once said, what other people think about you is none of your business. Okay, and so I try to live by that.

CRAIG

You say that, on one level, I completely agree with you, that's the game, you know what you're in. I think on another level, though, if we played it differently, and we're actually a bit more understanding about people who make mistakes and took into, you know, context and the fact that you'd known someone, and then you're new to the job, and I get all the stuff, it’s tough, you know, there's you, make a mistake, and you're out. But I do also think, you know, having been through years of politics, I look back and think, couldn't we all be a bit more human to each other? And wouldn't it be a better place if we were?

ANTHONY

Yes, but let's be realistic, because one of the worst words in the English language is ought, the second worst word is should. And so I'm a cursor, I use vulgarity, but you know, I tell my five kids, the two worst words, don't ever use them in front of me is ought and should because the world ought to be that way, we should act that way - but we don't act that way. And let's deal with the world the way it is not the way we want it to be or the way it should be. Now we can each do our part to make the world a little better. And I'm trying certainly do that. But I do accept that that's how people are, that is human nature. There is schadenfreude in our society, and people get pleasure from other people's pain. They rubberneck car accidents, and they do things like that. I get it. I was the car accident of that moment in time. And that moment in time passed. Now there's things you can do with it. Okay, so, you know, I like to joke to people when I'm on the public speaking tour, you know, I have a million Twitter followers more than Donald Trump, everybody laughs, you know. And I and I know how to own my mistake. But it's also made me a reasonably high-profile person. And I'll say this to you, Craig, about the universe - I'm an entrepreneur, I probably shouldn't have been in politics. But that mistake and that colossal firing, and that publicity, gave me a platform to speak out against Mr. Trump. He is a scourge to the ideals of America. He's a threat to the American capitalist system and the American democracy. And it gave me the opportunity to speak out against him and articulate why. So it was a very bad thing for me, but there's been a lot of silver linings to that. And that's a big lesson for your listeners, that you can have a bad thing happen to you but you can also turn that lemon into lemonade.

CRAIG

It's so interesting. This comes up time and again that people have been through a traumatic experience or something that's incredibly difficult, but they almost feel it was worth it because of the things that they learned. Another thing that you said you'd learned when I was reading about you was, when pride and ego are present your decisions will always be emotionally charged and muddled. And you've already spoken a little bit about that that your ego was involved. Do you try now not to have the ego so central? And what does that mean? And how does that work?

ANTHONY

I would like to think and, you know, I would like to think it has made me a better husband, hopefully a better father, hopefully a better runner of my company, you know I'm the managing partner and founder of my company, I like to think that. I have been humbled by markets, I've been humbled by life. I think that I try to reflect a little more before I react to something because of what happened to me. I'd like to think it's made me a better person. It's five years later.

CRAIG

And just before we started recording, we saw your wife and she was trying to help you find the microphone. And it was lovely to see you with her and interacting with her. Because actually, when you were getting fired, it sounds like your marriage was totally on the rocks, and you were heading for divorce. Tell us a little bit about that. And how you brought that back together?

ANTHONY

Well, first of all, we love each other, but she's a tough cookie. She didn't want me to go work for him. There was also, because you're experienced as a political person, but that contributed to the demise of my marriage. We ended up filing for divorce, Deidre filed for a divorce on me.

CRAIG

Whatm because there was just so much pressure because of that on it?

ANTHONY

Yeah, I think I - listen,I think we love each other. You saw her this morning. It's five years after the quote unquote, divorce proceedings, we reconciled. And I think we built a much stronger, healthier, more transparent, authentic marriage, which I'm grateful for. I think that's another lesson for your viewers and listeners - don't make your relationships disposable. If you love each other, you know, you go through ups and downs and relationships. And we were obviously, at a real low five years ago, we could have disposed of our relationship and gone in separate directions. I don't think that would have been necessarily great for either of us or for the children that we have together.

CRAIG

Were you about to have another baby at the time, or was it just born?

ANTHONY

No, she gave birth. Well, that was another big issue, right. So I was at the White House. She was due on I think August 10th, and the baby came early. I think some of that was stress-related, frankly. And I was with the President of the United States in West Virginia. On the 24th of July, James Scaramucci was born July 24. And unfortunately, there was a ground stop. You know, when the Air Force One lands, there's a 60 mile radius around that plane where there's no flights over the plane for security reasons. And so there was no way for me to get back to New York. That did contribute to the pain that was going on in my marriage, I missed my son's birth. Now-

CRAIG

Did she feel you were choosing the presidency and the job over her?

ANTHONY

I would say we were already fighting prior to that. So I would say she already had drawn that conclusion months before. Okay, so we could bring that up, that was definitely on the lis pendens of mistakes that I was making. But we already had that one litigated. This was a mistake, I should have been there for the birth, timing being what it was, you know, my buddies in the military say, hey, man, you were deployed, you were working for the President, you're a public servant - I missed my son's birth, I was in Afghanistan. Okay, got that, but it's still very painful. And so that contributed to the demise of my marriage. I didn't fully destruct, thank God, we reconciled. But here's what I would say to you - I was a round peg in a square hole. Classic entrepreneur, not a politician. Love my family, should have been with my family. Made the mistake, have to own that mistake. But here's the thing I would say, there was no way I was getting back from West Virginia, there was no way even if I chartered a plane, I couldn't get to the plane in time for the birth because I had to go two hours away from Air Force One. And then two and a half hours back up to New York. There was no way to make it at that moment. So you know, it happened. But it's not the end of the world, the kid’s very healthy, and he's an awesome kid, and it's not the end of the world. You know, it is what it is. Yeah.

CRAIG

And then what's done is done, but I guess what I think is really interesting about it is the fact that you were able to repair and rebuild the relationship and I'm guessing that required you to eat a lot of humble pie.

ANTHONY

Of course, but I mean, here's the thing. You can be right or you can be married. You ever heard that expression before? You can be right or you can be married. And so you have to make a decision in your life, she had to bend a little, I had to bend a little, there's a process of forgiveness on both sides, okay, there's a process of healing. And then there's a process of openness and transparency so that you can have a lot of trust with each other. Right? That's it. If you want to rebuild your marriage, and you love each other, and you're committed to each other, then you try to rebuild your marriage. I just think we have a tendency in our society now to be very disposable. We cancel people immediately, they can't go on the air anymore, they said something stupid. We do things to each other that I think are damaging. And I would recommend that we not do. And, you know, I've lived that. And so we repaired our marriage. I went back and rebuilt my company. I took great, great risk, frankly, because you're a communications guy, you know, this: I didn't have to speak against Donald Trump in 2020. I could have just gone dark. There were many people that left the administration, they hated his guts. They thought he was an evil, malevolent figure. But they were like, hey, that's gonna cost me to go do that. I'm not gonna - I got death threats, people taking pictures of my front door, they're gonna come through the house and kill my children. I got people lighting me up on television. I've got people in a restaurant, who are like white supremacist Trump lovers yelling at me. But I was willing to do that, because I knew it was right, and I love my country. And so I wasn't going to sit there and allow somebody like Donald Trump to tear to pieces the United States. And also, as predicted, he didn't concede the election, as predicted, he said there would be fraud, as predicted, he didn't help in the transition between - a peaceful transition of power, which is a time-honoured tradition that goes back to George Washington. I mean, this guy's a low-life, okay. And so if you say, OK well he's a low life, a lot of people knew he was a low life before you went to go work for him - why did you go work for him? And again, I made that equivocation that I regret, but so did Pompeo who said mean things about him, do did Kellyanne Conway, so did Steven Mnuchin, so did - you pick the person, there wasn't a person on Trump's team, unless their last name was Trump, that was positive on Trump.

CRAIG

So I think that that's really laudable of you, because it is a big thing to take on, what was then a sitting president is now somebody who's still disputing, but I think actually, and I hope it doesn't sound patronising, what I think is more laudable is hearing how you went away and started examining yourself and asking yourself some serious and deep questions and, and learn some lessons from that. So with that in mind, I just want to take you back a bit because I read some of your books and you talk quite a lot about your childhood. You came from what in Britain we'd call a working class, Italian-American background. Just tell us a little bit about that background?

ANTHONY

Well, I would imagine it's not cookie-cutter, but it's not overly original. You know, my parents are from immigrants. My grandfather on my dad's side was a coal miner. My mother probably lived a better life from a financial perspective than my dad. Okay, so my dad was in a northeastern Pennsylvania town, coal mining town, dad was a coal miner. They had no hot water in the house until he was about eight or nine years old. And they were bathing with a propane - they were heating the water with a propane torch, if you will, pouring it into a bathtub. That's how he was cleaning up himself, until he was eight years old. A lot of strife. You live a hard life, you get hardened, okay. You know, there's alcoholism, there's spousal abuse, there's physical violence in families. And maybe there’s that in rich families, I'm not saying there isn't. But I can tell you that when you're living day to day, paycheck to paycheck, in some debt, lots of pressure on you as a person, and a lot of things outside your control. I mean, one of the most impressionable moments of my life, I was 11 years old, it was 1975, my dad came home, he was slamming the door, slamming the cabinets, I think some glasses actually broke the kitchen. And he was upset that his hours got cut back. He was an hourly worker. He needed that money by hour, but we were in a recession. And so his foreman cut back his hours. And he was taking it out on his wife and his kids. Now should he have done that? Obviously, he shouldn't have done that. And God only knows the anxiety he was feeling at that moment. But it was an impressionable moment for me, I said, okay, these people have no money. I'm gonna go out and get a job. I was 11 years old, I went and got a newspaper route. And then I worked as a stock boy in the local supermarket, and I was hustling for money. 1975, I was making $45 a week, pretty decent money. I was giving 25 of that to my mom to help with the budget, and I was pocketing $20. Why was I doing that? I wasn't spending it. But I was pocketing in case, God forbid, they needed it, okay, so I was building it up, you know, 50 weeks went by, I had $1,000, okay, and so I was there because I gotta make sure that these people are okay. And so there was a tremendous amount of anxiety in the house. And there was stress, you know, my older brother became a, you know, he's faced drug addiction throughout his adult life of cycling through drugs for 40 years, I became the workaholic…

CRAIG

You write a lot about that, and, you know, like, and explaining the toughness of the background, and maybe that they just didn't, they were doing the best they could, but they didn't necessarily have the emotional tools.

ANTHONY

I think that's the message, right?

CRAIG

Exactly. And I think that what’s also interesting is you talk a lot about the gratitude you have that when it came to supporting you, your dad cashed in his pension, but you also talk about the fact that, you know, he beat you quite a lot. And also your brother would beat you because, you know, he was bigger than you. That's gonna have an impact, isn't it?

ANTHONY

Well, yeah, because we were, you know, hit, my brother was getting beat. And so what he was doing, he was replicating that and beating me. And it was a cycle and circle of this dysfunction and too much violence for young kids. Okay, when you are 8, 9 10 years old, you shouldn't be getting pelted and belted and it's not, it's not good for your health, not good for your self-esteem. It's not good for anything. Okay, having said all that, why do I write about? I don't write about it for people to have any pity for me or write about it for somebody to feel sorry, I'm writing about it because it is a rite of passage. And I believe that if you want to have a good positive legacy in life, I'm writing about it because someone else is dealing with it. Okay, I work on the Safe at Home Foundation with Joe Torre, I don't know if you would recognise that name because you're a Brit, but Joe Torre is a Hall of Fame baseball manager, Italian-American from the area I grew up in, was verbally and physically abused by his dad, and so was his mom. And so he created a play on words for American baseball - Safe at Home Foundation. Why do I work on that with him? Because I want kids that may be going through the same thing, or even adults that experience that trauma, let's talk about it. And by the way, if you talk about it, and you heal yourself, you won't replicate it.

CRAIG

I do see that. And I think you draw a line there in what you were saying between your brother's addiction issues, and then your workaholism. And do you feel that you've finally dealt with that and that you feel like you're on safe ground? Or is it something you need to keep working at?

ANTHONY

I think it's a work in progress. Like I said, I'd like to think I'm a better person than I was five years ago. I knew that I had to try to teach myself. There's a lot of books behind me. And I read these books, they're not up there for ornamentation, okay, I am an autodidact. I read and I'm trying to improve myself. And this is a message to the blue-collar people that are listening or the aspirational people who maybe transcended the blue-collar life or living probably financially better, you know, I paid for my niece's tuitions. I paid for cousins. One of my cousins was a clammer, he dislocated his hip, he has no insurance, he has no health insurance, he has no service, he's not old enough to get Social Security. He's on my dime. And I'm not saying that to have you pat me on the back or anything like that. I'm saying that because when you grow up like me, and you make the money that I've made, you're not, I'm not going to live in a barb-wired McMansion by myself, I'm going to help these people who I grew up with, to the best of my capability, live a higher quality of life. And also, let me tell you something, there's a threshold of money that people need. Okay. And when you get to that threshold of money, a lot of anxiety leaves the system. My father never got there. And I think it created a lot of trauma and anxiety for him. He started out with no hot water in the house. You know, I remember as vividly as you and I talking right now, I remember March of 1972, vividly, okay, this 50 years ago, my grandmother and my mother were celebrating the arrival of a washer and dryer that was being installed in the basement of the house that I grew up in, and my grandmother and mother thought that this was, I don't know, it was like, the second, it was like a coming of Christ. They thought it was the greatest thing ever, because they didn't have to go to the local laundromat to do the laundry anymore.

CRAIG

You're incredibly vivid in terms of describing things and you said your mother used guilt the way that Bruce Lee used nunchucks, which are those sort of like star things that you throw at people?

ANTHONY

You have Jewish or Italian listeners, I mean, these people, it's literally a duopoly on guilt. I mean, they can give guilt in ways that you cannot possibly imagine. You know, I told my mother, I wanted to drop out of law school, because she didn't even know the difference between Harvard or Harford, and I hated law school. And I got home for Thanksgiving and told my mother I was going to drop out, and her go-to line, ‘I'm going to kill myself’. You gonna kill yourself? I'm going to drop out of - ‘I'm going to kill myself’. Okay Ma, forget it, I'm going to stay in law school. Do you know my mother lied about Goldman Sachs? I probably shouldn't be admitting this on a podcast, but she was telling her friends in the town that Goldman Sachs was a law firm. I was at the deli, an Italian-American deli, and one of my mother's friends came over to me, so how's the law firm you're working at? I said, excuse me? She said yeah, the law firm Goldman Sachs. Your mother's very proud of you. You're working at a law firm. I'm like, you know, Mrs. Giambelli… Yeah, um, yeah, great. It's great. I went home I said, mom, why are you telling this woman I went, that Goldman Sachs is a law firm? ‘Well, I'm embarrassed that you're not a lawyer.’ That's Italian men. That's the height of dysfunctionality, okay?

CRAIG

And you obviously love your parents, and still, they’re still alive and you're in touch with them.

ANTHONY

I forgive my dad, by the way, I… you have to, you want to heal yourself, It's a lot about forgiveness. The Buddhist are right about that okay.

CRAIG

And interestingly, that forgiveness is more about you than them really isn't it? It's about relieving yourself.

ANTHONY

You have to recognise that there are trials and tribulations in life, you have to recognise that some of the things that are happening to you, they're not personal, they could be because of the person that's infecting them on you, you see what I mean. And so you have to learn to forgive. If you're not learning to forgive, then you're trapped in that trauma bond. And then that anger, that repression of that anger comes out in different ways. It makes you less of a happy person. And so to me, I have forgiven my dad for all of the trauma that we experienced as kids, I forgive my parents, I love my parents. I also except, God only knows Craig what they were living with in the 1930s when they were born, or the 1940s, during the war in the aftermath of the Depression, coming from immigrant families that were uneducated, and God only knows. And my dad gave me a $10,000 check in April of 1982. And I said, Pop, I said, what is this? He said, oh, you know, I cashed in my life insurance. I said, what do you mean? Well, yeah, I don't know, it was like $100,000 life insurance policy that the union was paying through the union, they were deducting it from his wages. And he said, I don't really have a lot of money to give you for your tuition, but you're going to Tufts, it's a pretty expensive place. You know, and I was a pretty good decision-maker, and back then I made a decision not to go to the State College, I wanted to go to the private school, even though it was more expensive, so I thought the education would be better. And I just remember when I took that check, I was like, oh my God, my dad is giving me his life insurance policy. And I better not screw this up. Okay, so I was a wayward teenager, okay, I mean, I'm Italian, I was driving around in a Camaro, I had gold chains on, you know, watched Saturday Night Fever 25 times, I was, you know, doing things that you probably shouldn't be doing in high school. And when he gave me that check, it was like an epiphany was like a wake up call. I was like, okay, I'm not going to disappoint him or my mom. This is too important. When I get to Tufts, I'm going to torque up the intellectualism, I'm going to torque up the studying. And you know, I crushed Tufts, I mean, I graduated top of the class.

CRAIG

And I can see that, that just put booster rockets on you and that kind of thing. But you also say, you know, when you talk about the family, and all the understandings of where they came from, and they were trying and all the things they did for you, you also write, ‘the price I paid was steep, with hours stolen from my family, I thought things were important, but they weren't’. And I just wonder if all of this basically led you along a path that was actually the wrong conclusion that you just had to keep running. You had to keep trying to keep pushing.

ANTHONY

I had so much financial anxiety as a kid and so much [unintelligible] anxiety, when I got started in my business, that it was all work all the time. Because I was like, okay, I'm not going to fail. I will outwork everybody around me. I will be all work all the time. And then when I paid off my school debt, I said, okay, now I'm gonna go start my own business where I can control my own destiny, all work all the time, all work all the time. If I'm being fair, that impaired my first marriage, it ended in divorce. She's a nice person and a very good mom. I would never say anything bad about her. We just got married very young. We got married at 24 and 25, respectively. But we have nice adult kids today, okay, but I contributed to the failure of that marriage through my workaholism if I'm being brutally honest. That's what it was. And so I've really tried to learn from that. And I've tried to reshape my time pie chart, if you will, and make sure that I'm detaching myself from the impulses of workaholism to do other things.

CRAIG

So you and I have got a lot in common, we were Directors of Communications in politics, okay, but we, you know, we also love reading and, you know, we also recognise that F. Scott Fitzgerald is one of the great writers. And the one thing that we agree he’s a great writer, but we also agree that when he said, ‘there are no second acts in American lives’, that that's actually not true, actually, people have a new life and reset themselves again, time and again. And you said that the test of a first-rate emotional intelligence is the ability to forgive yourself while keeping a sense of humour about yourself. So what you're saying is like that you can have a second act, you can but you have to a) forgive yourself, b) willing to learn lessons. And then also have a kind of sense of humour about it, say, hey, that happened and move on.

ANTHONY

You see so I do think that that trauma that I experienced in that firing, I think made me a better person, I think is another big lesson for your listeners, take the millstone of regret off of your neck, and put it beside you. I don't wake up in the morning, Craig and say, wow, I said something really stupid in the White House and kick myself in the pants, and live my day with my shoulder slung in regret. I made a mistake, I own the mistake, I have now forgiven myself for that mistake. I'm doing the best that I possibly can, for myself and my family. I took exogenous risk to go from the neighbourhood I grew up in to where I am today. It would be impossible to get every one of those decisions right, okay, including the decision to go work in the White House. I'm moving forward, I'm starting today, it's a beautiful summer day. Let's see what we can do today to enjoy life. It's not easy to do. Trust me, I was down on myself after I got fired from the White House. But I wrote in the book, you want to pick yourself up, you want to be a study in resilience. I also wrote something in that book, I don't know if you read this part where I was walking with my son on the promenade and the kid put his arm around me, he's like, hey, Pop, you are right? And I was like, this kid's parenting me, Craig, right? And I looked at him, I said, it's not a disaster, I don't have cancer. I said, let me tell you something, watch what I do with this. Okay? Because I want you to learn that if something bad happens to you, you have to be resilient, you get no pity party for yourself. And you get up, no victimisation, you get up and go. You know.

CRAIG

So I did read that. And it was very moving. Um, you and I could spend ages boring everybody to death about politics. And I've tried to sort of move away from that, we’d probably love the conversation but others might be a bit bored by it. But I did want to touch a little bit upon politics, because I think it's relevant to what you're saying. It feels like with Brexit in the UK and Trump in the US that when that happened, and a lot of other things around the world that it was almost as if in politics, we'd stopped being able to honestly disagree with each other. And increasingly, as the years have passed, it feels like increasingly governments struggle to do difficult things, because they're in such a noisy environment that their motivation is always going to be questioned, that there's going to be shouting and screaming. And it's extraordinarily difficult. Just reflect a bit on there about that politics and whether or not we can actually turn that around and make it any better.

ANTHONY

Yeah. Well, listen, I mean, that is the most powerful question. And so I can't speak about the UK because I don't know it as well, but I can speak about the United States. My observation is that we've lost our civic unity. And we’ve become very tribal, we've been splintered by the social media, we've been splintered by the fragmentation of the media. And I would say something that would probably get me upset with everybody, but we need a call to national service again, we need - and I'm not saying it has to be a military draft, but we should have a one or two year, you're going to serve the country. It's like the Israelis do or other nations do. And it'll force people from that, the code is to meet the New Yorkers to meet the Floridians, to meet the Californians and all of a sudden, let's reconnect and recognise how much we have in common as opposed to bashing each other. The other thing that's going on right now is the politicians are using a culture war in the United States against each other. Okay, so we got this bully named Ron DeSantis, he's the governor of Florida. He's putting out a Don't Say Gay law, the Disney people have gays that work at Walt Disney Corporation, and so now he's gonna punish them, using the power of his government to take their tax breaks away from them that were established 50 years ago to build Disney World. And so that's part of a culture war. He's doing that so that he can own the libs and he can get a cavalcade of people united around him. It's a jackass thing to do. And it's frankly un-American, but that's where we are right now, with some of these jackasses that are in leadership.

CRAIG

And I agree, and I think a lot of the culture war stuff is actually invented and deliberately designed to stoke people up and wind people up.

ANTHONY

Of course, and by the way, I am not gay. But you know what, I didn't choose my sexual orientation. And so therefore, somebody that is gay, as a libertarian, they should be able to live their life any way that they want to live it. These conservatives are [italian], that means crazy in Italian, like a chicken running no head. And here's what it does Craig, it takes the middle of the country, and what I mean by the middle of the country, I mean moderates, they become very apathetic and they drop out of politics.

CRAIG

AndI think you're seeing a lot of people who are in or around the centre, centre-right centre-left field, who's representing me now? And I was reading the other day, actually, about Churchill in World War II, is that we look at his rhetoric and think it’s some of the greatest rhetoric ever, you know, up there with Martin Luther King and some of the greatest orators ever, but actually, in World War II, apparently a lot of people listened to the speeches, and felt that he was drunk. And he was slurring his words and didn't like it. And it made me think, how would Churchill be in an era of social media? How would that go down? And it's, it's almost like this thing that has been injected into the system that's dividing us, making it very, very difficult and creating a dynamic where people are nervous to do anything.

ANTHONY

You know, I think it's well said, I don't really have a lot to add, other than I'm in complete agreement with that observation. Well, I don't want to be overly Churchillian, right, but keep going. You can't underestimate the power of perseverance. You can't underestimate the power of resilience.

CRAIG

Okay, this has been a great conversation. I've really enjoyed talking to you, Anthony, the one question that we always ask people, at the end of the podcast is, you know, you've said lots of lessons, lots of things that you've learned and gained from all your experiences. If there was one piece of wisdom that you want to share with people and say, Look, this is it. This is the big one. What would you say it would be?

ANTHONY

I would tell people, hey, it's life, if you're expecting it to go perfectly, I don't know what planet you're on, okay, this thing is going to be rough okay, you are living in the human condition. And what did the ancient Greeks say, there's a smiling face, and there's a sad face, comedy, and tragedy. And the ancient Greeks say both parts of those things are going to be in your life. And so you're better off trying to just enjoy them and getting through them as opposed to lamenting and playing the victim. So that's a big lesson. Second thing, Churchill said, which, you know, he had his issues, trust me, he's not, a very flawed human being, but there was something he said that I often repeat to myself is the best among us choose not to judge human frailty so harshly. Like all human beings, we come with this complexity, this frailty, this background story, our self-narrative, and so therefore, we need to have compassion for each other. You're a politician, okay, I’ve been in politics, we demonise our adversaries, okay. I sometimes laugh at the two dimensional caricature that was presented of me, I was Tony Soprano on the Potomac. I was a Jersey Shore cast member, they were really doing a lot of Italian stereotyping. They were trying to two dimensionalize me, they wanted to leave out that I went to Harvard Law School, I was the, you know, well positioned somewhat influential financial services executive, they wanted to leave all of that out. That's fine. But I don't want to do that. I want to inflate people back to the three dimensions of what they actually are, okay, and have compassion and have empathy. And I think that's the biggest lesson I can leave people with.

CRAIG

And I think listening to you, you're saying, you know, accept the condition that we're in, and that doesn't mean giving up. It just means you stop unnecessarily fighting things that just are.

ANTHONY

Okay, you know, what, if you're lucky, your parents are going to die before you do, okay? The great tragedy of life I think is, God forbid, one of my children died before me. I pray everyday that that doesn't happen. My point is though, I didn't make up these rules, okay, and we have a mystery to life. And so we have to accept and embrace that mystery. We can choose faith if we want to or we can not choose faith. It doesn't matter but you have to accept that there are rules that we didn't make up, we didn't create. But we're gonna have to live with those rules, whether we like it or not. There'll be tragedy and comedy in your life, and you have to embrace both.

CRAIG

So you've accepted a lot. And I think that that's great. But I think also what it seems to me listening to you over this last hour is that you've also been prepared to question a lot of assumptions that you had about yourself and about life and you've been willing to openly and honestly engage with that and say, look, I got that wrong. Or maybe I was choosing the wrong path.

ANTHONY

No question. But again, the path to getting something right is the admission that you got something wrong. You know, me and my buddies are double down entrenched in Donald Trump nonsense, but secretly hate Trump, but they can't get out of their own way. Be honest, I think if, let me tell you something okay, there's a lot of people listening right now to your podcast, very famous podcast, so most people may not like me, I don't know. But here's the thing. I'm leaving it on the field, I'm telling you exactly what I think nakedly and down deep, every person, they have a respect for that. And I have a respect for that, when I'm talking to somebody that I know is not spinning me and they're offering me a real, authentic behaviour, I'm drawn to that. Even though I don't like the person, I'm like, okay, hey, at least the person is being honest with me. Do you see what I'm saying? And go do that, I think you'll have a much more enjoyable life if you do that.

CRAIG

Listen, I think that's a great place to leave it Anthony, my suspicion is I think a lot of people listening to this will have really appreciated it and will like you. So thank you very much.

Wow, the words to insights ratio in that conversation was incredible. Anthony is a controversial guy. But he left me feeling he'd really learned from his mistakes. And I admire his desire to share that. Next week's guest is another fast talker. The BBC is Chief International Correspondent, Lyse Doucet.

Lyse Doucet

I remember when we managed after great, great effort and argument getting into what was called the besieged areas where no food, no water could get in, and no people could get out, and to go inside there and you'd come out and you would collapse in tears. When you live in war, war lives in you.

CRAIG

Lyse is all about empathy and that shines through our conversation, where she talks about her nomadic lifestyle, and a decision not to have a family. She's one of the most likeable and thoughtful people I know. If you enjoyed this episode, please like and follow, or even write a review for Apple or Spotify. Desperately Seeking Wisdom is produced by Sarah Parker for Creators Inc. Goodbye for now.