Open Book with Anthony Scaramucci - May 2026 Q&A: Rebuilding After Trump, 3 Books That Changed My Life, Young Men in Crisis

Episode Date: May 19, 2026

This month's Q&A, we're getting into everything: the three books that changed how I think about money, how I went from Goldman Sachs to sick in bed on day one of my own company, and why I still say my biggest do-over would be working for Donald Trump. No scripts, no filters, just me, your questions, and the truth right off the cuff. Please keep submitting your questions below. 📚 Books mentioned in this episode: The Richest Man in Babylon by George S. Clason One Up on Wall Street by Peter Lynch Buffett: The Making of the American Capitalist by Roger Lowenstein You Are the Message by Roger Ailes The Elements of Style by Strunk & White 11/22/63 by Stephen King Anthony Scaramucci is the founder and managing partner of SkyBridge, a global alternative investment firm, and founder and chairman of SALT, a global thought leadership forum and venture studio. Pre-order my next book, All the Wrong Moves: How Three Catastrophic Decisions Led to the Rise of Trump, out on the 17th of September in the UK and the 22nd of September in the US: ⁠https://www.scaramucci.net/allthewrongmoves Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Madamy Holmes bike for brain health supporting Baycrest returns on May 31st for its fifth anniversary with a new start and finish at the Aga Khan Museum. Join thousands of cyclists as we take over the DVP and Gardner Expressway in support of dementia research and brain health. Riders of all abilities are welcome and both regular bikes and e-bikes can participate. Bring your friends, family, or corporate team, and make an impact. Register today at bikeforbrainhealth.ca. Okay, we're back, everybody. Welcome to Open Book. I am your host, Anthony Scarrett.

This is the May 26 Q&A episode. Very, very happy to get all these great questions. There's great stuff coming in. Of course, we appreciate your support here at Open Book. And if you haven't, please subscribe to the channel. It really helps us out with the algorithm. So press the button. I mean, the button's somewhere around here.

All right, let's get into it. And we'll start with YouTube. From what I can see, you and your wife have an incredible relationship where you help make each other stronger. What is the key to that strong relationship and making it work for a longer period of time? What is the big mistake you see in relationships? Well, I mean, this is a great question.

I would tell you that Deirdre and I love each other. I think number one, I think the secondary thing is if people are doing things that you wish they weren't doing or they are human, you got to forgive them. Okay, I have said things to Deirdre her that I regret. And she has said some things to me that she probably regrets. And our relationship has never been perfect. So I don't want to suggest that to anybody. But where I see our relationship

working is that you have to be like with your children, with your spouse, you have to have like an unconditionality that is going to work. If you don't do that, what ends up happening is you can create space in the relationship where people start to miscommunicate with each other. So I would say that. That's the biggest mistake I see in relationships that, you know, people miscommunicate or they don't say the right thing. And by the way, Deirdre and I were through divorces. We've each been through a divorce. So this is both our second marriages. And if I was being brutally honest about my first marriage, I probably was a little bit conflict avoided. And I probably didn't explain exactly what I needed. And so I've certainly tried to correct that as well. So at least, listen,

relationships are not perfect, Desi May. mine with Deirdre isn't. We try to work on it every day. We love our families and our children, and so that certainly helps as well. We got a new dog, by the way. So I just want everybody to know that I am going down the list, okay, of importance, okay? And the dog is going right up the list. And for all you dog lovers out there, you know exactly what I'm talking about.

So, all right, let's go to Instagram, John Aubrey Davis. How do we rebuild the viability, integrity, institutions after Trump? I'm such a great question. Can't really short shift this answer. There's a lot that has to happen, and it has to be bipartisan. I think we have to really work on this together and probably get people from both camps and sort of end the tribalism. What I fear is that a lot of the things that Trump is doing right now, if the Democrats

take control, they'll do the same things back to the Republicans, and then they'll have this sort of pendulum swinging back and forth, killing each other. But we have to revisit some of our institutions, perhaps end Jerry Man. and Citizens United, but then the other thing I think we need to do, which is also very controversial, but I think very necessary is we've got to put some guardrails up on the Congress and try to curb the spending because the spending is out of control and it's really going to take away from the future of our children if we keep this up. So those are some of the big things. LinkedIn, Aditya and Chapati.

Hopefully I said that right. And if I didn't, I apologize. Young men could be the swing vote in the upcoming U.S. elections and how can potential parties do what they need to make them aspirational again? Well, I think that's the big thing. There's a reason why Donald Trump, Joe Rogan has been critical of Trump, it's a reason why Trump doesn't go after him because he knows that he is an independent thinker, Rogan, and he controls a lot of those male swing voters that you're referencing.

So I would just say we've got to spend more time with those people and we've got to come up with better policies to make them feel included. When you feel left out of something, you get angry. When you get angry, you vote on extremes. It could be right-wing populism or left-wing populism, and I sort of think that those things are not providing the solutions that we need to go forward. But young men will be drawn to that unless we come up with these types of solutions.

They need jobs and they need livelihoods and they need to get out more. Let's face it, right? With these statistics on young men, Scott Galloway and I did this, a special series podcast called Lost Boys. We won the Webby for it this year. And it's an eight-part series. I would encourage you to look at it because it does explain a lot of the things that we need to be doing. Okay. X. Open Outcry Trade. Looking back on your early days in finance, which three books actually changed how you thought or worked? Such a great question. Okay, so again, the richest man in Babylon by George Clayson, one up on Wall Street by Peter Lynch.

and the last one when I read it was about 31 really did change me was the making of the American capitalist and this was 31 years ago so this was Warren Buffett at the age of 64 which is a couple years older than me and just think about how much life he had after 64 at age 95 now that book is written by roger low and see you read those three books you'll be ahead of everybody most everybody in finance Okay, YouTube, RJ Sanfran, what is your framework for spending versus investing versus philanthropy? And how do you view passing down money to your children? These are great questions.

So listen, I don't spend that much money. In fact, my financial advisor was like, man, you're not, you don't spend a lot of money. And why don't I spend a lot of money? Because I think the spending of money, you've got to be very, very careful. It's not that I'm cheap, I'm definitely a generous tipper. If you're in the restaurant, you know you're getting a great tip for me. or you're made in the hotel. I'm going to give you a great tip.

But I don't think it's necessary. And I don't, I think it's too ostentatious. Remember, I have a lot of blue collar family members. I don't want to be that, you know, person that looks like a big wheel to his family members. Just not for me. So I'm probably low-key on spending. With my kids, I'm all about their educations and their housing. And so I've made sure that all their education,

are paid for and I've made sure that they're, they've got some good places to live and they're comfortable. But I also want them working. And so there's a delicate balance there. And then with the philanthropy, my wife and I pick a few good charities. If I'm doing it, I want to be on the board. If on the board, I will make a big investment in the charity

and also ask my friends to do the same thing. So that's helpful. These are really good questions. You are such a concise and effective speaker. This is from Instagram, J. Deke. Any advice to develop this skill? Read Roger Ailes' book, you are the message. Okay, I don't even know if that's even print anymore.

You'll find it, but read it. And then when you're done reading it, Jay, read it again. That's my recommendation. It'll make you crisper. It'll make you tighter. You should also read Strunken Writes book elements of style about writing because your verbal voice and your written voice should be more or less identical. I think you'll find that in the books that I write, that it sounds like me.

So those are a couple of good piece of advice there. Instagram Elizabeth Moff. What should an 18-year-old focus on to be successful like you? You're a big inspiration. Well, that's very kind of you, Elizabeth. But here's the thing, okay, you're 18. You got something that you really love, something you're super passionate about. Learn as much as you can about that and start idealizing in your mind that job.

Okay, so whatever it might be, get going on it. One of my kids is into film. He's locked in. One of my kids is into songwriting and song singing. She's locked in. My other kid's a venture capitalist. They're all locked in. You've got to find something, Elizabeth.

Even at 18. Find something that you really, really love. Lock yourself in. And really good things will happen to you. Okay, LinkedIn. Libby Collette. How does your faith impact your approach to business and parenting? I mean, again, he's a great question.

So I'm a practicing Catholic. I know that there's a lot of secularists out there, and particularly in Europe, there's a lot of atheists and all that other stuff. But I have a tremendous amount of faith in God. I go to church. I go to confession. I believe in the Holy Spirit. And also, obviously, I believe in the resurrection. So if you believe in those things, believe it or not, you have a tremendous amount of faith that things are going to happen and unfold in a way that will be okay.

You'll be able to deal with it. If you find that faith in life, you'll be able to deal with it. I mean, the number one thing as a Catholic, you know that this is temporary. And I'll just remind people what happens to Catholics on Ash Wednesday, it's 40 days before Easter. And you've got to take a piece of ash and put it on your forehead. And the priest remind you that you started out as dust and you're going back to dust. Okay, that's very humbling.

And so I think your faith or my faith at least makes me humble. and I do think that helps me in business empowering to get my ego out of things and just try to do the right thing. Okay, Instagram, London, Amy, 2.0. What amount of downtime do you have weekly? How much vacation do you take? Jesus is a really good question.

And I don't want to give you fake news, but if my wife was here, she would say, he has no downtime and he works through his vacations. That's what she would say. But I actually think I do have a little bit of downtime. I try to take a Sunday off. I probably am working on a Saturday, believe it or not,

because I've got a lot of things going on on my business and got to make sure operationally it's okay. Sam Walton worked every Saturday. So I probably work on Saturdays. I would say I'm good for three weeks of vacation, but unfortunately you'll find me doing a podcast while I'm on vacation or something like that. So, you know, it's harder for me to unplug, frankly.

But remember, I like, what I do. So I don't really feel like I'm working, right? So there's a, there's a little bit of a insight there. Do something where you don't really feel like you're working. What is your favorite what if in history? This is from Daniel Della Bovi. Well, you know, watch the man in the high castle, four seasons. It was originally on Amazon. It's now on Netflix. So you can find it on Amazon or Netflix. This is sort of this alternative spectrum of history. There's the 112263 by Stephen King. You can also get that on like a Hulu or even Netflix,

but you could read that book, which I read years ago. That was another great book on alternative history. Okay. YouTube slow passenger. I like that. I want to be a slow passenger at times. Okay, I sometimes feel a bit insecure about myself,

doubting myself, feeling pressure of what is expected as a young man heading into my 20s. Especially seeing stuff on Instagram. How do I get into a mindset of being comfortable outside? or not caring what other people think at me. So this is the biggest thing. First of all, shut the Instagram off. Give yourself a break. I'm not saying to shut it off completely,

but just say, okay, look, I'm going to use it for an hour. If you're going to use it for two hours, if you use it for eight hours, too much. Read a book. Watch something. Watch a YouTube lecture. Do something different. That would be my recommendation to you.

But I would just say doubting yourself and feeling pressure is normal. So take a deep breath on that. But manifest, you've got to get yourself into a mindset. A lot of books about positive actualization and thinking big. And if you do that, over time, things will start to manifest in a way that you want. You can create your life. But you've got to dig in and you've got to believe.

And the first person, you've got to believe in yourself. And when you start doing that, you start projecting that confidence, it becomes habitual. But it is totally normal to feel the way you. you feel. So don't be too worked up about it. What is my fitness routine? This is from Derek Potslaw from Instagram. So I have a trainer. I try to get in the gym four times a week. I've got a little bit of a gut on me right now, which I'm not in love with. So I don't have a perfect training and eating schedule. I'm not like one of these perfect guys that you see on Instagram where they got zero body fat and everything works out beautifully. It's not me. I am 62 though. So I'm in okay shape for a

62-year-old, but I'd like to get my VO-2 max up. I think it's called, and I'd like to get my hang. Peter Attia says you've got to hang from your chin at bar for two minutes. I've got it up to a minute and 15 seconds, so I'm working on that. I would just say, get in the gym. If you just start and build the micro-habits, it'll lead to some good success in the gym. LinkedIn, Kate Doak, recently talked about economic aspiration of your mom and Nona in the early 70s regarding laundry appliances. That's true. And the economic desperation, any people are feeling today, how can America become aspirational again? Well, listen, you know, we got to pay people more. I think that's really what it's about. I think we've got, you know, if you look at the economic rent and the society,

If it goes 50-50 to labor, meaning 50 to capital, 50 to labor, guess why people are very happy. And maybe there'll be a guy that's heading for a trillion dollars. They'll be worth only $900 billion. But there's a lot of workers that are feeding their kids and owning homes and feeling good about themselves and feeling good that their kids can do better than they do. And I think that our differentiation in terms of have and a have-nots is widening. And last time it happened to this significance was like in the 1900s, and Teddy Roosevelt put a stop to it. He was actually the father of progressivism. And I'm just saying that we have to have to do that.

We've got to get our stuff in order and we have to push more equality. And pay people more is basically what we should be doing. And if we do that, it'll filter down. Henry Ford, I mean, he was an SOB in many ways, but he understood that you had to pay people enough money to afford. the car that they were producing. And it made all the difference in their world in terms of their seeking and their family seeking their aspiration. Okay.

So Instagram. Plot E0. What is your favorite band and the best live show you've ever seen? So my favorite band bar, Nunn, is Led Zeppelin. I actually saw Ron Wood in a restaurant last night, a little bit of name dropping. So I am a Rolling Stones fan. And I want overset a load of the guy. He was actually very friendly.

But I am a Led Zeppelin fan. I want that played at my funeral. And I would also say my best live show is Billy Joel used to come to my uncle's motorcycle shop when I was a kid. My uncle had a really good relationship with him. He used to give us tickets to Nassau Calcium when I was a kid. I think that's probably the best live show. And of course, I went back to see Billy at Madison Square Garden. So he's probably my favorite live show.

Paul McCartney as well, I would say he was up there. What's your favorite film and why? This is from Samantha J. Ben. If you could have an actor play the mooch in a movie, who would it be? George Clooney. Probably have to dye his hair a little bit. Of course, I would want George Clooney. But Brad Pitt.

I mean, who wouldn't, right? I mean, come on. Just kidding. It would probably end up being Remy Malick. But in any event, those are the people. I would say, and by the way, I was in a movie with Josh Brolin years ago, 15 years ago, I was in Wall Street, too. he became a friend and I really like Josh as well.

My favorite film, everybody says to Godfather, but I'm partial to Braveheart. Watch that movie. It's an entrepreneur's movies. A lot of renegade status going on in Braveheart. 1995, 30 plus years ago, stole my favorite movie. All right, we're going to keep moving here. We're keeping it real.

Instagram, Kohlstein. What are your right-leaning political values versus your left-leaning political values? values. Okay. Really good question. So left-leaning, I'm for social inclusion. So gay marriage, a woman's right to choose. I'm for this sort of libertarian value that I don't care what other people are doing in their lives as long as I'm not hurting anybody. Why do we have to hurt each other? Or why do we have to impose our lives or even the way we think about the country culturally on somebody else? Not a big fan of the culture war. Either way, the left beating up on the right

or the right beating up on the left. That's my opinion there. But on the right side, I'm actually for pro-business. I'm for propitious and decent regulation for businesses that can expand growth. I am for climate regulation that will hopefully help us roll back some of of things that are going on with the environment. Even if you're a climate change, the clientist, if you don't believe in it, which I do believe in it, but let's say you don't believe in it, that you're smoking, coking up the air, the incidents of children's related asthma is through the roof, non-smoking lung cancers through the roof. So we have to figure out a way to cure these things.

And by the way, we have the technology to do it. So I don't know if that's right or left-leaning, but it's people-leaning. You know, I'd like to see myself as not really right or left-leaning, but more what's right or wrong for people. And that's why I get in trouble with everybody. Okay, YouTube, Markerboy Double Zero, can you describe your interest in astrology? When I say the word astrology, you say what? I say operating system.

So listen, I believe in it. So people think I'm crazy, but I believe that we're born with an operating system, and I believe the ancient world understood this better than anybody else. They understood that we were influenced. We're made of stardust and that there's a celestial connection. If you're the same composition as the Earth in terms of your water weight and your matter weight, roughly 70% water, 30% matter, roughly the same as the Earth. Well, the moon affects the water on Earth. It's not affecting the water in your body.

Of course it is. Ancients understood that also 28-day cycle. Half of the planet is set to that. They saw that not as a coincidence, but a celestial connection. So I would just ask people to be open-minded about it. But that's what I think. Operating system. Personality.

Know your personality. Help you with yourself awareness. Okay. Instagram. Susan M. Brown. If you had one do-over, what would it be? Wow. You know, probably, yes, weird because I would tell you it probably wouldn't have worked for Donald Trump.

That would have been my do-over. Then again, they ended up working for him. I got my ass kicked. I think it made me a better person. and maybe you wouldn't be listening in my podcast if you didn't know who I was. So I don't know, there's good and bad about things, but that really did suck. That would probably be the do-over that I would want. But again, you can't do do-overs, as we all know. You got to accept your life. You're going to forgive yourself for your mistakes and get up in the morning, do 15 push-ups and

10 squats and bite the ass off a bear, right? What are we going to do? So no do-overs, Susan M. Brown, but that would probably be the one I would want. Instagram, Vince Hoffman, how do you take the first sleep from employment to entrepreneurship. Vince, that is a really good question. Let me tell you something. That is the scary question because you have to be a nut. You know, you have to jump off a cliff and try to build the airplane while you're descending to earth.

That's what entrepreneurship is. I got really sick the weekend I left Goldman Sachs. Making good money. I went from seven figure pay at Goldman Sachs in the mid-90s, which was, I mean, great pay to no pay. And I got myself sick. I was so stressed out, I ended up getting like, my immune system went down. I had a fever and a sore throat the first day I started my first company. Believe it or not, I had pain, intention, and anxiety, even though I had a little bit of money set aside when I started my second company, which is Skybridge, the one that we're running today.

So, no, it sucks. You got to have, you got to feel the fear, and then you got to do it anyway. that's basically the message there. These are great questions, by the way. Instagram Adam, W1982. That's the year of my high school graduation, Adam. 44 years ago, wow. What are the three top inspirational quotes from political or historical figures?

Such a great question. So I'm going to give you three off the top of my head. From Ben Franklin, if you want a friend, ask a person for a favor. about that. It's counterintuitive, but it's a very good way to think. And you'll also be able to engender and build relationships. Second big one for me is from Mel Brooks, relax. None of us are getting out of here alive. I think that's probably the one that makes me laugh the most and also puts things in perspective. And I would say the last one is from Warren Buffett. And this is really about the stock market, but it's also about your analytical thinking and delay

gratification. The market is a voting machine in the short run, but it's a weighing machine over long periods of time. So think about that. You know, people can get crazy in the market. They sell something that's worth a lot of money. They get manic depressive. But over time, the market really does find value. And I think you will also find value if you think of it that way. So be long term and you're investing. All right, guys, but um-bump. That is a wrap on the Q&A episode for Open Book. Listen, we're reading all of your comments. And I love hearing what's on your mind. So keep sending the questions. Make sure you subscribe to see the latest episodes and to submit your questions.

And listen, I'm sure I missed the question out there, but we'll be back next month with another round of answers. Until done, let's keep the conversation going. I'll see you next time. This is one of my favorite things to do every month. So shoot me your questions and I will give you my answers right off the cuff right here on Open Book. Thank you again.