Anthony Scaramucci Unfiltered: Wall Street, President Trump, and Building Confidence

What this episode is about

The discussion highlights Anthony Scaramucci's experiences with leadership, resilience, and personal growth after his abrupt firing from the Trump administration. It explores the interplay between power and ego, the importance of self-acceptance, and the challenges of maintaining confidence amid adversity.

Key takeaways

• Real leadership shines in service; it's about elevating others, not just leading from the front.
• Bone-crushing defeats shape resilience; even the mighty fall and rise stronger through humility.
• Embrace your flaws; true acceptance of personal darkness is the foundation of genuine growth.
• Success stems from flexibility—plans crumble under pressure; adapt or get flattened like a quarterback.
• Intellectual curiosity fuels leadership; ask questions and learn, no matter how powerful your position.

Who speaks in this episode?

• Ryan Hawk (Host) · 21 min speaking
• Anthony Scaramucci (Guest) · 32 min speaking

What is discussed, and when

1. 0:00 – 5:00: Derek Jeter, Paulina Pompiano
2. 5:00 – 10:00: Donald Trump, Vidy Testy
3. 10:00 – 15:00: Donald Trump
4. 35:00 – 40:00: Donald Trump, Skybridge Alternatives
5. 40:00 – 45:00: Skybridge Alternatives, Salt Conference
6. 45:00 – 50:00: Amazon

Notable quotes from "Anthony Scaramucci Unfiltered: Wall Street, President Trump, and Building Confidence"

• 2017. What's going through your mind on that day? People think I got fired for the newspaper article. Trump didn't give a [ __ ] about that. I knew I was Cook when he called me…

  about Donald Trump · at 0:13

• Started, but you look great. Okay. Hey, an uncommon comment on that. I was doing all my prep. I talked to Paulina Pompiano who did a big deep dive on you and she's amazing.…

  about Paulina Pompiano · at 2:39

• One of them. I didn't really understand this until later in life. And Derek Jeter said it better than anybody.

  about Derek Jeter · at 4:02

• Night and you are getting your ass kicked on the field, smashed left and right. And there was a guy named Vidy Testy, that son of a [ __ ] Okay, he played for Sonica High…

  about Vidy Testy · at 5:01

• So, I was at this college event in 2011 and the event you're referring to is called Salt. It stands for Skybridge Alternatives, but now it's got its own brand as a thought…

  about Skybridge Alternatives · at 39:57

• The banker that took this public. And this number may not be perfect, but you could get the number from Grock. If you put $10,000 into Amazon on the IPO, what's it worth today?…

  about Amazon · at 47:40

Who and what is mentioned in this episode?

People

• Donald Trump — Person · Referenced power figure / former employer · 5 mentions · first at 7:53
  Central reference point for Scaramucci’s discussion of power dynamics, loyalty culture (“full MAGA”), and the circumstances of his firing.
• Derek Jeter — Person · Referenced exemplar · 1 mention · first at 4:08
  Used as a leadership model for 'service' and team-first behavior, supporting the episode’s leadership-through-sports framing.
• Alonzo Kahoon — Person · Referenced life coach · 2 mentions
  Identified as Scaramucci’s life coach and contrasted with therapy; used to explain coaching as forward-looking accountability.
• Paulina Pompiano — Person · Referenced researcher/journalist · 1 mention · first at 2:43
  Credited by the host for doing a deep dive on Scaramucci, helping frame the interview preparation and biographical prompts.
• Vidy Testy — Person · Anecdotal sports rival (uncertain identity) · 1 mention · first at 5:06
  Mentioned as the high-school opponent who delivered 'bone crushing defeat,' illustrating resilience and early leadership lessons.

Companies & orgs

• Skybridge Alternatives — Company · Business focus · 2 mentions · first at 39:31
  Mentioned in the context of hosting the SALT Conference and pivoting into digital assets.
• Amazon — Company · Case study · 2 mentions · first at 47:19
  Referenced as an example of a company that successfully built an 'everything store' and executed a long-term strategy.

Places & events

• Salt Conference — Event · Business focus · 1 mention · first at 40:02
  Described as a thought leadership event that started as a survival strategy for Skybridge Alternatives.
  So, I was at this college event in 2011 and the event you're referring to is called Salt. It stands for Skybridge Alternatives, but now it's got its own brand as a thought leadership event. And some kid said to me, Sir, could you.

Full transcript with timestamps

0:00 One of the key things that makes a good leader is service. But then the number one thing, Ryan Hawk, is bone crushing defeat. You got fired by the most powerful person in the world. July 21st, 2017. What's going through your mind on that day? People think I got fired for the newspaper article. Trump didn't give a [ __ ] about that. I knew I was Cook when he called me a deep stater on Friday. You You can't be on the team unless you're full maggot. Can we get personal for a second? I read that your dad abused you guys growing up and it messed your brother up big time, but it turned you into a workaholic. You did a lot of research. I'm impressed. Not only is everything you said true, but it's worse than that. Your wife was going to divorce you. What did you do to fix that? Sometimes we go into the denialism about our own weaknesses. We want to pretend to the world that we're all good when there's some dark features to our

0:54 personalities. And so, you have to accept that. When you think about power, how have you been so good at managing egos and people with immense power? Combine intellectual curiosity with neuroplasticity. I am a comfortable outsider. I'm not an insider. You got to make a decision about being comfortable in your own skin. You can make a lot of mistakes and still be a success, but battle plans go by the wayside with contact with the enemy. Confidence. The first fight is with yourself,

1:32 Anthony. Man, it is awesome to have you here on the Learning Leader Show. Welcome, Hawk. How's my lighting, by the way? You got to be impressed, right? No, I was going to say you lined it up perfectly with the window. You're in London. Are you in London? Is that where you are? No, I'm in the British countryside. I'm going to the Chalk History Festival, but you know, I'm a I'm a vain son of a [ __ ] And I'm just wanted you to acknowledge my lighting before. Are you wearing makeup? Are you wearing makeup? No, no, no makeup. I swear. No, I got good skin. Okay. All right.

2:05 Those are that those are stem cell moisturizers. Hawk, you're a young man. When you know, you're going to teach me about leadership. I'm going to teach you about vanity. Okay. I I'm gonna I'm gonna teach you my tricks. Okay. Afterwards, you're gonna have these. Send me where you go. Okay. I I need I want to look like you. All right. Okay. You could use a little sod replacement on the top there as I'm noticing. And I got I got that trick down, too. All right. But this is your podcast. I I just wanted you to acknowledge my You just sent me an email after with all of your advice on things I need to do to look like. I just wanted you to acknowledge my lighting before the show started. Okay. Well, the show's already started, but you look great. Okay. Hey, an uncommon comment on that. I was doing all my prep. Um, I talked to Paulina Pompiano who did a big deep dive on you and she's amazing. She's been on the

2:48 show. So is her husband Anthony. Um, you you played quarterback. I'm a former quarterback, high school, college, a little bit after college. And I've drawn so much from that time. I'm curious about you, though. What have you drawn in your life as a leader doing a variety of things from your time as a quarterback leading a team? So, I got hurt, by the way. You know, I I hurt my left knee. I tore my ACL and that knocked me out of my senior year, but I was captain of the team. Uh I'm a I'm a little short guy, but I had a good throwing arm. And this is going to sound a little bit braggy, but I'll just say it. I was I was someone that could read the defense. And so I there was a kid on the team that had a much better arm than me, but he wasn't as anticipatory. So I could get to the line of scrimmage and you could see the eyes in the people you know what they're blitzing or what their formation was. We did a lot of audles at

3:41 the line of scrimmage. So, I think I learned a couple of things. Flexibility, fluidity, and decision making. You can't just say, "Okay, here's the GL game plan, right?" Because that's what Mike Tyson says, right? You have the plan until you get punched in the face or all battle plans go by the wayside with contact with the enemy. So, fluidity was one of them. I didn't really understand this until later in life. And uh and Derek Jeter said it better than anybody. So I'm going to paraphrase from him and and quote it back to you. But but one of the key things that makes a good leader is service. And so if you're on the team, it's not about me, right? It's about you. How am I going to make you better? How am I going to make you feel good about your role? How am I going to get you to think that I'm here to help you? And so Jeter understood that better than anybody. I think he was the real glue that got them to all those

4:36 championships. Never cared about his percentages, never cared about his hit totals, averages, didn't care. He was like, "How am I going to get there? How am I going to get the team there?" And so, you learn that in sports. But then the number one thing Ryan Hawk is bone crushing defeat. You know, you've got your little cheerleader girlfriend out there and she's waving the pompoms and you're going to take her out on Saturday night and you are getting your ass kicked on the field, smashed left and right. And there was a guy named Vidy Testy, that son of a [ __ ] Okay, he he played for Sonica High School. He went on to University of Miami. Ended up playing for the Jets, Cleveland Browns.

5:17 He was a monster in high school. He was a year older than me. and his team, Sana High School, ran over us. I mean, literally, I have tire tracks on my back from politics and business. But my first tire tracks came from Tessaverie, that son of a [ __ ] And and I had to get my ass kicked. Here I was, this little 5'9 squirty Doug Fluty like quarterback, and this 6'4 good-looking giant with a howitzer was, you know, destroying us. And I just remember feeling so puny in front of my high school girlfriend. So, how you got to get over that, right?

5:52 That's that's called resilience, right? Such a good such a good question. But that's that's that that's how I would unpack that for you. I Well, I love it. I think there's so much to learn, especially from the adversity and preparation it takes and you understanding a defense like some of that so much plays as you're out in your life building a business or getting tapped. I am curious about your story, though. Let me let me tell you something, Mark, because you know this, okay? because you have an aura about you of confidence and charisma. You know, people listening, confidence, the first fight is with yourself. That's the first fight in life. Am I good enough? Am I worthy? Uh can I get to the game? Uh can I believe in myself enough so that I'm standing next to someone else who believes in themselves that I'm can compete? Because if you go into the game mentally thinking that you're not there,

6:44 you're not going to be there. Henry Ford had one of the best lines in civilization. You want to hear the line? He was a son of a [ __ ] but he had a great line. You want to hear the line? If you think you can or you can't, you are right. Right. Yeah. Okay. You've heard it before. And you know exactly what I'm talking. You got to get in the mindset. Okay. You're going to fire me from the White House. No problem. I'm gonna I'm I'm a crash dummy. I'm mayhem from the All State commercial. I'll fly through the window and I'm going to get up and dust myself off and I'm going to keep going because that's my mindset.

7:17 You're not going to take that away from me. Whatever you think of me actually is none of my business. I'm going to do me and I think that's a big thing in sports. It's a big thing in business. It's a big thing in life. You mentioned the White House. So, I'm curious about, no offense, but I had not heard of you prior to your job there, right? So I believe it started. No, no offense taken July 21st, 2017. What's going through your mind on that day? Well, you know, look, I had worked with Trump during the uh, you know, the 14 months with Donald Trump on the campaign. I worked with him on the executive transition team. Uh, I had a good relationship with him. Jared Kushner once said that uh, Trump likes talking to you because you remind him of his dad. you made your money on your own. You don't give a [ __ ] You're not trying to kiss his ass like these other people. And you tell him right to his

8:12 face what you think. Unfortunately, I brought that with me into the White House. That was not the right attitude in the White House. He he was a little bit more brittle in the White House. And so, you needed to be a lot more obquous and I didn't I didn't I didn't have that. Why Why would that be any different? I think uh I think the job um ah the personal look you you get in that job Barack Obama once said about that job it magnifies your personality and so I think in his personality was uh I'm right my instincts are better than everybody else is you better couch out to me and we're going with my instincts come hell or high water and don't talk back to me or don't contradict me in the campaign It was way more loosey- goosey. He was more entrepreneurial. It was like, "Okay, I'm taking a flyer on the presidency. Nobody thinks I can win." He didn't think he could win. And so, it was a little bit more loosey goosey. It

9:09 was a little more interactive. But when he got to the White House, it was like, "Okay, I got to the White House. You didn't get to the White House. Don't tell me what you think. I know what's best." You see what I mean? See, people think I got fired for the newspaper article. Trump didn't give a [ __ ] about that. Trump Trump laughs about stuff like that. I got fired because I was in a little bit of a tangle with him on a couple of different issues. And then he finally said to me, "I knew I was Cook when he called me a deep stater on Friday." He said, "You know, I didn't realize you were a deep stater." And I'm like, "Well, first of all, I'm not a deep stater. I've only been to Washington once prior to this. I think it was on like a school field trip, okay? I'm a I'm a kid from Long Island.

9:46 I'm just looking out for your interest." And don't don't tell me that. Don't tell me that. And then Monday, I got fired. But that's fine. Listen, I mean I mean you're asking me about the 21st of July. I really thought I was going to go in there and help him. There was some friction going on in terms of the cultural merger of the MAGA team with the RNC. And so the RNC was more establishment, the MAGA team was more aligned with Trump. And I had good relationships with both sides. I was hoping to see if I could fuse those. Uh, but what Trump figured out, again, rightly or wrongly, I just want to be objective and observant, is they weren't going to fuse. So, he blew up the RNC.

10:27 You know, Trump Trump has done something politically masterful. Again, you can like Donald Trump or dislike him. I'll just tell you what he did. He decapitated the Republican National Committee. He decapitated what was formerly known as the Republicans of George Bush and John McCain. And he did an M&A transaction, hostile takeover. he inserted his team into that team and uh it's now full MAGA. You know, you you can't be on the team unless you're full MAGA. And of course, the quote Donald Trump himself, well, what is full MAGA?

11:00 Whatever I say it is, right? So, it's a it's a it's a party of personality now, less about any levels of guiding principles, but the best thing they've got going for them are the Democrats because they're in complete disagree. They're lurching further and further to the left. The country is not that far to the left. And so the the Republicans under the Democratic mismanagement, they have an opportunity here to control the card table for probably a decade, maybe a decade and a half. If Democrats are going to go hard left in a national election, like they just got this kid uh who won the Democratic primary in New York City. Uh he's a hard left progressive devout socialist. I'm just going by what he says, not me. Uh you know, the country doesn't want that. and and that's been a failed situation in Oakland, a failed situation in San Francisco, failed situation in Chicago, and it will fail here in New York. And

11:55 so, you know, it is what it is, you know. Well, it feels to me, it seems like we're somewhat aligned. Uh Elon Musk, in fact, when he was kind of going through that little breakup stage with President Trump, um he put out a poll and was like, "Do we need a third party that's somewhere in the middle?" And I know that's kind of where I live, uh that's somewhere in the middle. and and and it was like 82% of the respondents to that and there's millions and millions of respondents to this is Elon Musk, right? And they they said yes absolutely we we feel like we don't have a home. We're somewhere in between. H what what do you think about that?

12:31 Uh you know it's it's a I'll give you bad news and Elon Musk is right and we do need a third party and if anybody could pull off a third party it's him actually. He'd have to make a decision to go in that direction. It would cost $50 billion. He'd have to put up 10, find five other guys to put up 10. And then you'd have to build a coalitional party that that is radical moderates, radical centrists that want to reform the government and not do what's happening. Now, this is a a little bit longer of a conversation, so forgive me. But uh what happened in 1992 is a gentleman by the name of Ross Perau ran as a reform party candidate, won 19.9% of the vote. So 33 years ago, the Republicans and the Democrats got the [ __ ] scared out of them. And so they collapsed on third parties. They tightened their duopoly. They put up a lot of procedures to block third parties from entering races. U they've squashed

13:32 them. Now that was a good thing for them to keep their power bases but it was a very very bad thing for the country because they allowed each other to jerrymander districts. They allowed each other to uh stay in this permanent perpetuation of power. So you know Chuck Grassley's like I think he's like six or 700 years old. I you know he's still in the Congress. I mean I don't know. I mean I don't know. He he'll he he'll be running uh from Iowa from a Ouija board long after he's in the crypt, you know? I mean, they don't leave and they don't have to leave because of what these guys did in terms of the way they set up the system. And so this causes candidate and public servant apathy for the people. So like, I don't have to serve the people.

14:19 I can do whatever the hell I want and I'm I'm going to curry favor with the lobbyists. I'm going to feather my bed and I don't have to worry about the people. And so in the undercurrent of that, you've had this spectre of populism. The people have said, "Hey man, this sucks. You guys are taking care of the fat cast. You're taking care of the rich. What about me in the lower middle class? What about my rising living standard? Uh I was once uh in an economically aspirational family as a blueco collar person and now these families are economically desperational.

14:49 [ __ ] you guys." And so that's that's what's happened. And so, you know, Musk is right. Can he break that duopoly? That's the question. Can you break the duopoly? And the answer is you probably could, but you need $50 billion dollars and you need some very cunning people. You need you need candidates that understand reality television and understand that this is an entertainment festival, understand that this is a popularity contest as much as it is a hiring decision. Right? the kid, the 33-y old kid that won in New York, he's a charismatic kid. Uh the policies are misguided, but the social media was A+.

15:32 You know, the little clips and the this and the that and he energized a group of people. And Andrew, my friend Andrew Cuomo was running a campaign that was more uh politically consultant driven, was more advertising and mailer driven. Uh and we're in a digital world now, you know, and this is why uh this why Bitcoin is going to do well. Now, the old folks don't see it, but Bitcoin's going to do well because the younger people, like you, Ryan, are living in a digital world, and so they will accept things like digital currencies and digital stores of value. Yeah. Well, we could go really That's a mouth That's a mouthful. I appreciate it. I appreciate it. How's my lighting, Hawk? Forget about how's the lighting? You look amazing. Okay. Uh, can we get Can we get personal for a second? Anything you want, man. We can talk about anything.

16:19 So, so I love I love your show and it's a I'm flattered to be on. Thank you. There. So, there was a a time where based on like your devotion to your work, at least from what I read, you can correct it if it's wrong. Your wife was going to divorce you and was like, Anthony, like peace out, dude. I'm not doing this anymore. But then at her insistence, again, correct me if this wrong, she's like, you need to work with somebody. Get a life coach or somebody like that to help you. Um, is that true? Like, can you take me inside that story and how you worked through that problem because you guys are still, from what I've read, happily married to this day.

16:56 So, that was close to not continuing. What did you do to fix that? So, so not only is everything you said true, but it's worse than that. Um, and so, yeah. So, so I would say to you that uh I owe my wife, Dearra, a debt of gratitude for actually really loving me because I was off the rails on a few things. It wasn't just the political ambition. Uh you know, I had made some mistakes in our marriage. And so she's like, "Hey, I'm not having this. Loves me. Filed for divorce. You know, we're a little bit of a hotheaded Italian group of people." It was sort of like a shot across the bow.

17:35 And she's like, "Hey, I'm not having this. So, if you love me, get your [ __ ] together. Otherwise, we're going to be divorced and we're going to live apart." And so, she was right. I was wrong. And I think the lesson to that is you have to take accountability in your life when you're wrong. Now, I do love her very much. And thank God she loves me, right? Because if you love each other, you can stay married. You know, there's a there's a great cliche. Are you married, Hawk? Yes. Yes. Okay. So, there's a great cliche. Tell your wife this. You can be right or you can be married. You have to make a decision. Okay? Meaning, you know, no, you can, you know, meaning you can be right. You can be right like in righteous, you know, husband's wrong and you're right and then you're divorced or you could be right or you can be married, you know, meaning meaning you have to I'm sorry. Go ahead.

18:23 The one the one thing that the one phrase I don't like, Anthony, let me see what you think is happy wife, happy life. I'm okay with happy spouse, happy house because like we're equals in this thing and so like I don't think you just it's good insight. You know what I'm saying? Like that's the one thing I don't get that when people say so so I think at times I'm right and my wife is wrong and at times she's right and I'm wrong. So I don't know if that's exactly my point is you might be right let it go. You know what I mean? In other words like you love her you know your people there's going to be some friction. It's not you're not going to have perfect harmony. There's no such thing except in a fairy tale. Yeah. But, you know, we were both on our second marriage. Um, love each other. Uh, I was over my skis.

19:08 I mean, she hated Trump. She probably hates Trump as m almost as much as Melania hates him, which is like a very high standard of like hatred, right? I mean, that's like Eastern European hate. You know what I'm talking about? I mean, that's like, you know, Joe Stalin type of [ __ ] right? I mean, they are they are still married, I think. Yeah. but she [ __ ] hates him and she doesn't live with him and you know he part of the reason why he's so miserable is that he's in the white you know you want to hear you want to want to laugh you know Trump once called me and he told me that you know you can't get any internet porn in the white house because they got all the sites blocked down you know no way that call happened living alone by himself yeah you know anyway we can move on to another topic but I mean that's the funny part of Trump which I do you know you have to understand like I don't

19:50 like the policies I don't like the bicass ity of the personality, but there are some fun things about him and it's the reason why 80 million people voted for him, right? He is the most famous comedian in the world. I mean, you have to just accept that he is, right? He has a he has a dryness and a delivery that goes over in a way that people find humorous. But back on back on the target, Dear and I heading for a divorce did a per walk in the Nassau County family court together. Uh, at the end of that session, I drove back to the home that we were living in, which I was now living a part of, and I said, "Hey, you know, I still love you. I think you still love me. Should we try to work this out?" She then said to me, "Yeah, but you're [ __ ] up and you need to go see somebody." And Tony Robbins is a good friend of mine. And Tony recommended a life coach who worked with him for 30 years. And Tony said

20:51 something to me. He said, "Listen, you come down and see me. Uh you and your wife should come down and see me and uh let's see if we can help you." And so we did that. We went to like date with Destiny. We had some private sessions with Tony. I then went to the life coach. And one of the things about it is accountability, Ryan. Right. You talk about leadership, your books, your podcast. Are you or are you not accountable? Like sometimes we go into deni denialism about our own weaknesses. we go into denialism about who we really are. The we want to pretend to the world that we're all good when there's some dark features to our personalities. You know, this is why Robert Green's books have done so well. You know, the 48 laws of power and I've interviewed Robert on my podcast and I love Robert. But but I had to go through a reckoning with myself. I had to become less conflict avoidant. I had to become more honest. I had to

21:45 become more direct in terms of what my feelings were. Um and we turned our marriage around. Now was it perfect in the beginning after the fight started the first 6 8 12 months? No. Uh but is it a way better marriage and a stronger marriage today 8 years later? Do we love each other? Yes. And I think we have a tendency in our society to be very disposable with each other. You know, she could have divorced me and been totally justified in divorcing me in 2017 and called it quits, but that would have been bad for her in my opinion. It was certainly going to be bad for me. It would have been bad for our two beautiful children. And I think the message, again, this ties back to leadership. Stay in things. You know, you don't don't make everything in your life disposable, particularly the things that matter. And if you're working on yourself, uh, one thing I have found with my adult children, because I've obviously had a

22:41 failed marriage, my first marriage was a failure. Uh, but I've got three beautiful adult children. I think they give you the benefit of the doubt if you're working on yourself. I think your employees give you the benefit of the doubt. You know, talking about athletics, if you're the guy in the gym working out, training your body to improve your performance, are your fellow players going to like you more or like you less if you're doing that, right? So, so work on yourself. You know, this is what makes your podcast so good because you're bringing on people that talk about real things and put things in perspective with a level of authenticity, right? And genuine curiosity. What are you currently doing to still work on yourself? Well, you mentioned my life coach. I have a life coach. Oh, still.

23:29 Yeah. Yeah. I speak to him once a week. Uh sometimes I ask him to speak to my kids or maybe even an employee or um you know, is that like therapy or are there are there like I'm I'm fascinated by like how a coach works with a person like what do you does is it does it does he or she give you prompts? Like what how does it go? Such a great question. And so again, I've had therapy. I feel that therapy is a regression. Life coaching is a progression. Okay? So if Tony Robbins were here or Alonzo Cahoun, who's my life coach, uh, and I'm happy to mention his name in case people want to use him, uh, easy to find. Um, first name Alonzo, last name Kahune, C A H O O N. I just say that Scaramucci sent you. Okay. He'll he'll let out a laugh cuz I've referred to him a lot of clients. But a life coach is forget about the past. What the hell are you going to do? You're not going to what are you going to do? We're going to

24:25 we're going to relitigate the past all day and discuss what went right and wrong. Who gives a [ __ ] What are we doing today to make yourself a better person, a better dad, a better athlete, a better leader, a better friend? What are we doing today? And how are we setting up tomorrow so that tomorrow is a better day than today? And uh how are we going to live with a cup overflowing with optimism about the world? Uh there's a lot of reasons to be pessimistic. That's life. You know, you're the human condition. The ancient Greeks said it better than anybody. If you walked into one of those outdoor theaters, there was a placard of a face that was smiling. And then right next to it, there was a face of great sadness, comedy, and tragedy. And what would the ancient Greeks say? That's your life.

25:13 You're going to get a package of tribulations in your life. Some of them are joyous and some of them are tragic. And by the way, it's going to be tragic. Okay? You're going to end. You're going to re meet your own demise. You're going to have to say goodbye to people you love. And so, you have to accept that. And and by the way, you could be a billionaire, a multi-billionaire. It doesn't matter. You know, one of the most heart- rendering things, and I always tell people this, about 30 years ago, Bill Gates's mom died of breast cancer, and I think he was on Charlie Rose or one of those interviewers, and he said, "Look, at that time in my life was the richest person in the world. You don't think I would have given my money away to save my mom's life to extend the years of her life, but it was an impossibility, right? God has batted a thousand on planet Earth. I mean, we had one guy came back. He rose from the dead

26:02 three days later and he he was here for 40 days and he then he's gone. You know, my point my point being you're going to die. Okay? So, what are you going to do? Face the music in your life. Enjoy your life. Embrace your life. You know, you know, the pessimists look at it and say, "Oh, well, it's worthless anyway. Why would I even bother?" The optimists are like, "Hey, I'm here. I'm breathing. I'm going to have a good meal, a good cup of coffee. There's some fun people around that I can love and hang out with, and there's some businesses I can build while I'm here. Why not enjoy myself while I'm here to the best of my capability? And whatever tragedy besets me, let me handle it with some level of dignity.

26:43 Let me handle it with some level of kindness towards others. Right? I think I think that's the messaging of life coaching versus, you know, my dad hit me when I was eight and so now I'm [ __ ] up and, you know, I don't know. I I I I don't I don't think I'm not a huge fan of the therapy. I'm not saying you shouldn't do it if you need it, but I'm a better fan of the life coaching because I think it's more progressive. I read that your dad abused you guys growing up and it messed your brother up big time, but it turned you into a workaholic. What What impact like h how has that played out now that you look back on those years? I know you look you're looking forward, but that is a part of your life and a part of your history. How how did that impact I I'm I'm impressed that you did your homework, you know. So, I did a podcast with my brother in 2016, which I always refer to people to about addiction. And

27:35 so, my brother became a cocaine addict. Uh 40 years cycling in and out of cocaine, maybe seven or eight rehabs. Uh he's 63 today, doing well, very smart guy. Uh lovely guy, you know, sensitive guy. Uh but a real guy, you know, someone I love very much. Um, he became a cocaine addict. I became a different type of aholic. I became a workaholic. And so, yeah, my dad was rough on us. U So, what do you do? You can either hold that anger for the rest of your life or you can forgive and you can choose to forgive him. Who the hell knows what happened to my dad when he was a kid, you know? Who the hell knows? I can't I can't tell you. But for me uh and this is the same thing for you or anybody listening. Okay, the best among us. Okay, this is something my grandmother would have said. She would have said it in Italian, but I'll say it to you in English. The best among us choose not to judge human frailty so

28:33 harshly. Okay. So, whatever was going on with my dad, maybe depression, a lot of anger in human life is represented uh it it there's underlying depression that gets represented in anger. When I see somebody blowing off or super angry and charged all the time, they're probably manifesting some level of not feeling well about themselves. Uh I mean, look, everybody can have a temperamental blowoff. I'm not saying that, but I'm saying a consistent level of anger is usually a sign that there's uh there's an underlying depression issue and maybe that was my dad. What am I going to do? I have to choose to forgive him, which I have. Uh but I would also say this about human frailty, that means ourselves. So, if I'm working in the White House and get my ass fired, which I'm fully accountable for. I never blamed the president or John Kelly or anybody for getting fired. I think I'm fired because I wasn't serving the

29:33 president the way he wanted me to. He fired me. So, I can wake up in the morning, Ryan, and say, "Oh, I did something stupid in the White House. Let me kick myself in the pants today, uh, and have this regret." Or I can take that millstone of regret and leave it behind me. Take it off of my neck and leave it behind me. And I would say say to people, uh, human frailty and not judging it is not just you judging others, but also yourself. the [ __ ] that you're doing that you don't like, the [ __ ] you're doing that you regret. Why don't we forget that? Why don't we move forward? Why don't we forgive that? And I think that's a very big message, very big resonating message that helps people again that helps their careers, it helps their relationships, it helps their their business life. And but yeah, no, my dad was very rough on us. He was rough on my mom. uh they were in a traditional Catholic marriage so no one

30:30 was going anywhere. Uh and uh that's that's where we are, you know. I mean, but listen, I talk about it for a reason because somebody could hear it and they could recognize it. There's a signal that I'm trying to send to somebody and I appreciate you bringing it up on your podcast because maybe someone's listening and they hear the signal and say, "Okay, look, that guy got through it. I can get through it." And I think I think it's important. And by the way, that that podcast my brother and I did, 500,000 people have listened to it. I was in an airport once and I was passing my luggage through the, you know, the TSA and a guy taps me on the back and he says, "Mooch." I said, "Yeah." He goes, "Oh, you don't know me? I'm blah blah." He goes, "You know, I'm seven years clean and uh I go to meetings every week. You know, I'm in AA to keep myself off of alcohol. And sometimes when I can't get to a meeting,

31:20 I have the conversation that you and your brother had on that podcast. I have it downloaded on my phone. And if I can't get to a meeting, I will put my earbuds in and I will listen to you guys describing your upbringing and you guys describing directionally what happened to each of you because there's compassion there. You know, there's a there's a you know, you know, you want to relate to other people. Express your vulnerability. show them that side of you, you know, and they're like, "All right, this guy's a real dude. He's not He's not He's not trying to be better than me. I'm not trying to be better than anybody, Ryan. I'm not better than anybody. I'm not worse than anybody, though, either, you know, and that's another big message for people, you know." Yeah, I appreciate you sharing that. And um I think you also just taking ownership over the situation cuz cuz I know there are some who would

32:09 choose to use that and have a victim mentality um and then go act out in a bad way and and cause harm to others. Ed Ed Latimore was on this podcast and he grew up in a really tough situation. Mom's a drug addict selling drugs and and he said if I go out and commit a crime the judge and jury don't care about my upbringing. They're sending me to jail, right? I got to take ownership over what I do. Like I like that. One of the things about you um Anthony is that you uh are a very powerful person and you've been surrounded by power a big chunk of your life. You've got fired by the most powerful person in the world.

32:46 Um he hired you as well to work with him and there are many others around that orbit. And so I'm fascinated by power and how it works and power dynamics and how you work well and kind of bob and weave amongst powerful people and continue to rise up which you're doing as we speak. When you think about power like what how have you been so good at managing egos and people with immense power in the world? Well, I mean I don't know if I'm really that good. I mean I got my ass fired by Trump, right? I mean, I'm I'm I'm probably I mean, again, this is probably going to come across bragging or something like that. I'm not trying to brag. I'm just trying to say this what I would say to people. Find your superpower. Okay?

33:32 Yours, you're a great interviewer. You've got great insight. You understand leadership. You're fascinated by it. I think your superpower is very similar to my superpower. And I'll tell you what that is. Intellectual curiosity. And so if you can blend intellectual curiosity with neuroplasticity, uh, meaning you can adopt and change, okay, then you can move in various circles. You know, I'd like to think that the clamors on Long Island, I can relate to them as well as any person that I would meet at the World Economic Forum because I grew up with them and they're me. Uh, the flip side is the people that I'm meeting at the World Economic Forum, guess what? you're the clammers, you know, better or no worse.

34:16 You know, there was a kid, it was a very smug kid I was in law school with. And he was, you know, some kind of intellectual [ __ ] spewing from his mouth. And I just looked at him. I said, "Let me tell you something, okay? There are kids in my neighborhood that are putting in sheetrock right now that are [ __ ] smarter than you." Okay? I just want to let you know that the problem is that those kids' fathers put in sheetrock. And guess what they're doing? They're putting in sheetrock, but they had super high IQs. They did really well in school and high school, but because of their financial limitations in the family, uh, and the way they thought about things, hey, you're you're joining my sheetrock business. Okay? And, and so, call yourself out. And so, I guess the point I'm making to you, combine intellectual curiosity with neuroplasticity. You can go from a polyester suit, which is what I was

35:06 wearing at my first Goldman interview. I was fully flammable Ryan Hawk for my first interview at Goldman Sachs. If if a match went off, the whole thing would have caught on fire. I had a polyester shirt on, okay? I looked like a young Italian undertaker from Brooklyn. And the guy said to me, "Look, you're a smart kid, but you're the worst dressed person that we've like ever met here at the Harvard Law School. So, I can't invite you down to Goldman Sachs dressed like this." And I looked at him. I was like beat red. I was so embarrassed. He said, "You got to go to Brooks Brothers, buy yourself some natural fiber clothing." Okay? And I remember calling my mother and my mother's like, "He doesn't know what he's talking about.

35:42 You look great. I did not look great, Ryan." Okay? I did not look great, but I didn't know any better. And so, you can either have shame about that, or you can create that adoption. And you can say, "Okay, I got to get with the program. I got to find what I need to do to get into these channels." But I'll leave you with one last thought. Okay? I am a comfortable outsider. I'm not an insider. Even though I may be inside the room at the White House or inside a salon at the World Economic Forum, I'm a kid from Long Island that grew up in a bluecollar neighborhood that went to a public high school, K through 12 public schools, uh, and has some reasonable brain capacity and built a couple of businesses, but I'm not I'm not an insider, but I'm comfortable with it.

36:33 You know, like guys like Trump or Rudy, they're uncomfortable outsiders. You see what I mean? And they get they get they get nerved up. They're like, "Fuck, you know, you won't let me into your golf club. I'm going to build 18 golf clubs. You're not going to let me into your salon dinner on the Upper East Side. I'm going to become the president of United States to shove myself up your ass." You see what I mean? But I'm a comfortable outsider. I don't need to do that. You know, there are golf clubs on Long Island. They would let me in possibly to landscape the greens. That's possibly what they would let me in for. They're not going to let me in to be a member and I could either be upset about that or I could laugh about that. You got to make a decision about being comfortable in your own skin in life. Yeah, I sense that from you. Did you go to law school with Barack Obama? So he was behind me.

37:17 Uh so uh I did I was I actually Michelle Obama was a couple years ahead of me. Sort of weird. So she was cla I was class of 89. Michelle was class of 87. So, she was a 3L when I was a 1L. And by the time I was a 3L, Barack Obama, who's a few years older than me, was a 1L. Uh, and so I didn't really know them. I mean, I I I'm not going to BS people. You know, all the faculty when he was president said they taught him, which is mathematically impossible. And every single person in the school said that they knew them. Also, again, mathematically impossible. But I gave Obama some money in ' 07 and I walked over to him at a fundraiser and I said, "Uh, Senator," I mean, he was senator at the time. I said, "Senator, I got a big check in my my my breast pocket here.

38:08 Uh, you and I went to law school together. We didn't really know each other." I said, "I'm about to hand you a big check. Can I lie to my friends and tell them that you and I knew each other really well in law school?" Well, he looked at me and, you know, he had he had probably the best smile in American politics since Jack Kennedy. He smiled. He said, "You know what?" He says, "Anthony," he said, "If you double the amount of the check, we could take it back to Hawaii." Meaning, like we were in high school together. It was really funny. So, I I ripped the check up. Of course, I had another check in my wallet. I I doubled the amount of the check and I handed it to him. And uh you know, but he was very nice to me. Uh I went to a couple of uh Christmas parties at the White House uh during his term there. Uh and I like him, you know. I think uh I think he did some things that he feels bad about today. I mean, I think he I

38:54 think he needed to let Joe Biden run in 16. I don't think they understood the threat of the populism in the country or what Donald Trump was going to do to their party. Uh but, you know, listen, it is what it is. I think he generally did a good job. Remember, we were in a midst of a real bad crisis, the global financial crisis. Uh and he was a thoughtful guy, smart guy, and I think he I think he was a pretty good president. Um, one of the changing gears a little bit, one of the things that you've did, I believe this is 2008 that I like, um, is you started hosting events, uh, specifically an event, I believe the Skybridge Alternatives Assault Conference where you gathered kind of people together and I love this idea of bringing curious, thoughtful people together and creating collisions so that we could have conversations and learn through those things. Um, can you can you walk me through this idea that you had in

39:49 2008 to host this event and how it became like this this big time thing to bring people together? So, I was at this college event in 2011 and the event you're referring to is called Salt. It stands for Skybridge Alternatives, but now it's got its own brand as a thought leadership event. And some kid said to me, "Sir, could you explain to me your strategy and your visionary genius to create salt?" And I looked at the kid and I said, "Okay, we were going out of business." Okay, I just want to make it very clear to everybody. We were getting our ass kicked. Our fund was down 22%.

40:28 Redemptions were piling up. I thought for sure we were going out of business. And so I'm like, "What the hell am I going to do? I'm probably going to be a third party marketer for hedge funds." And so what should I do? let me start a conference because if I start a conference I might be able to uh bring people together, convene them and then raise money from them. And at that time it was during TARP all the big companies had canceled their conferences in Vegas. I went to the Encore Hotel which is attached to the win and we were getting rooms for $99 in 2009. That's how bad the situation was. And so this was an accidental survivor strategy. Uh this was a pivot that we were making in order to stay in business. This was not some mastermind plan. Ryan, moreover, during COVID, uh I'm sitting there, my portfolio is languishing. I've got to make a decision. What am I going to do? Well, we're going to pivot the whole goddamn

41:35 business. We pivoted into digital assets. We got over a billion dollars of Bitcoin related assets on our balance sheet right now. Uh, you know, almost nine figures of digital assets on our corporate balance sheet, but I'm talking about the balance sheet of the portfolio over a billion dollars in Bitcoin related assets. Uh, did that that didn't exist 5 years ago for Skybridge. So, why do we do that? Again, for survival. You you can't sit in a typewriter business and say, you know, the typewriters have sold successfully for 100 years. Let's stay in the typewriter business. You can't sit in the yellow pages and say, "Hey, you know, we cut down these trees.

42:15 We're we're dropping off four pound books stained with yellow dye. Uh, and that's been our business for 95 years. Let's stay in that business." You can't do that. You got to move and you got to recreate yourself. You know, uh, Wolf Gang Puck, who's a brilliant restaurant tour, he's got a restaurant that's been in existence for 40 years in Beverly Hills called Spago. You know what he does to the restaurant? Blows it up every 10 years. The restaurant's being shut for renovations. Blows it up. It doesn't look like it did in 1977. And the menu doesn't look like that. And you have to do that with your life. You have to do that with your business.

42:55 You know this this I could eat 30 Twinkies at age 15. 30 Twinkies. Trust me because I did it. Eat 30 Twinkies, not gain an ounce, okay? And go out and play football. No problem. I can't eat 30 Twinkies today at age 60. Well, first of all, I don't know what the hell I was doing eating those Twinkies. But you have to look at your world the way it is and you have to accept the world the way it is and adopt adapt and operate in that world. And so that that conference business was accidental. It's turned into a phenomenal business for us. And it also fed Skybridge lots of customers and it also helped a lot of my friends in the industry. You know, I've had people come to me and say, "Mooch, I went to your conference and I raised money from somebody at my that's awesome. That's those positive externalities are good karma and they're good for your overall relationship building. Well, I just think it's a great idea to bring

43:53 people together, too. I mean, like good things tend to happen if you thoughtfully bring people together, whether that's dinners, big conferences, event, anything. In my in my life, in my experience, in my business, it feels like so many good things have happened from bringing people together um and from relationships. That's how that's how all this stuff really happens. And there's another event I I I recently saw you given a talk about um the Sun Valley Conference. I was it maybe 1999, Jeff Bezos was speaking and I remember I feel like you were like, "God, I got to invest in that guy." But then you you changed your mind because Warren Buffett spoke after him and and was that like a teaching moment for your to trust your gut? I'm I'm curious about what happened. Talk you did a lot of research, man. You did a lot of research. I'm impressed. talk. Okay.

44:41 Thank you. Yeah. I know you did a lot of re tell try to tell the story that look I missed a lot of the tech boom be by by the way Warren Buffett is the man. I I I attribute his teachings and writings to making my family financially independent. So uh but like Warren Buffett I've got a lot of things wrong in my life. You know I had the Uber guys in my office. You want to hear another? I had the Uber guys in my office and they're like, "Okay, it's a $500 million valuation. We want you to put in $500,000." I'm like, "Okay, so give me the pitch."

45:15 Well, we're going to have an unknown guy in an unknown black car driving your 16-year-old daughter around Manhattan and we're going to charge your American Express card. I That's what we're doing? Yeah. Okay. Get the [ __ ] out of my office. I'm not going to put my daughter in an unknown car with an unknown guy. Okay. And I totally didn't understand. I totally missed it. Okay. probably be retired if I gave him that money, right? You know, the the the point I'm making is you can make a lot of mistakes and still be a success. But, you know, learn from the mistakes. Be more open-minded.

45:47 Bezos gave is my age, by the way. You know, he's born in January of 64, like me, and we're only separated by a few days in terms of the timing of our births, but we're also separated by about $250 billion, me and him. Okay? But he did something that was absolutely brilliant and he did something that was very well executed. So he gave a speech that day about books. He basically said, "Look, I'm not a book seller. I mean, I am a book seller, but I'm not going to be just a book seller. I'm moving these books around because they're roughly the same size. They're roughly the same weight. I'm trying to reverse engineer and dot plot where the warehouses should be. I'm going to build an everything store. And by the way, if you invest in this thing, it may take 10 or 15 years.

46:33 I'm not gonna make any money with me. I'm thinking about this over 10 or 15 years and then when I hit the spot, we're going to make a lot of money, but we're not going to make a lot of money right now. I have to build the infrastructure of this. Okay? And he was building real estate. He just wasn't building retail real estate. He was building warehousing so that he could retail deliver onetoone to people. This was a B TOC move that was absolutely brilliant. And Buffett said something after he was done speaking. I was like, "Okay, Buffett's always right. Let me rip this up." I ripped ripped up all my notes. He said, "Oh, lovely guy, really smart. I don't really understand technology or the internet. I'm not investing this." Oh, by the way, can you believe that this guy's valuation, his market capitalization for Amazon is bigger than Sears Robbook, the story Sears Robbook with all of its bricks and mortar retail everywhere. And

47:27 I was like, but yeah, of course. And I don't have the exact numbers, but uh I want to say, and Frank Quatron told me this, he was the banker that took this public. And this number may not be perfect, but you could get the number from Grock. If you put $10,000 into Amazon on the IPO, what's it worth today? I think it's like 20 million or something like that. Now, you would have had to gone through eight periods of time where you lost 50%. One period of time you lost 90 and very few people held it. Bezos did, but very few people held it from day one to today.

48:05 But he's a genius and he's a great executor and you have to acknow I made a mistake. I missed it. It was right there. It was right on the tea for me and I could hit it over the fence but I missed it and so it can miss it. So how am I not trying to miss things in the future? Bitcoin to me is that Bitcoin to me is that and uh I don't want to miss Bitcoin. You know, Bitcoin is me sitting there in that meeting in 1999. Yep. I know we got to run, man, but you're you're you're doing podcasts and most recently this this one called Lost Boys with our mutual friend Scott Galloway, who's been on three or four times and and will be on again soon to promote his next book. What's that like been w with Scott and your banter? You guys have both these great personalities. you're not afraid to speak your mind and and I I got to imagine that's got to be fun for you guys.

49:02 I adore him. I think he is one of our leading thinkers. I think he can turn a phrase about as well as anybody. I mean, I would love to see him in public office, frankly, because he's he's a healing sort of a guy. He's a visionary. Uh he's not an us versus them guy. He's a inclusive guy. Uh, and he's also honest, you know, and so what I love about him and I I met him through one of his books. Actually, I interviewed him for one of his books. He invited me then on his podcast, I think, with Edson. They do a brilliant job on that podcast.

49:37 He's also friends with Cara Swisser on the Pivot podcast. I know Cara. And so, a couple of mutual friends put us together. And then I went to him, had dinner with him, and we started talking about this epidemic of male self-esteem. If you're 14 to 34 and you're a white male in the United States, you have a 30% higher likelihood to commit suicide than other demographic groups. Whoa, that's a big number, by the way. And so we started talking about that and then I suggested to them, why don't you and I do a limited series? You know, we don't have to make it a permanent podcast, but let's just do it like a documentary, like a podcast documentary. We'll interview Richard Ree. We'll interview sociologists. We'll interview people that are studying this problem. We'll interview people that think we're full of [ __ ] that don't agree that there is a problem. And we'll put it out there into the public domain so that we can

50:31 raise awareness because like that podcast I did with my brother related to addiction disorders, let's talk about these things. Let's remove the stigma of what these things are and what they rep represent in our culture because if there's someone listening to you and me that doesn't feel good about themselves or they're in pain. And there was a woman recently, I think she was a famous Tik Tocker or YouTuber, she just took her own life. Her husband put out a press release and said that she was dealing with extraordinary personal pain and she ended her life. And so, you know, let's get those people help.

51:11 And the way to get those people help, let's let them not feel shame about the way they're feeling. It's like the message is, you know, it's okay to express what you're feeling. And you're not going to get judged, okay, by the real people that really care and love you. You're not going to get judged. If anything, they're going to embrace you and they're going to help you start to feel better about yourself. Because there are just like there's a treatment for your heart, Ryan. And just like there's a treatment if you have a bad knee, there are treatments for issues related to your brain. And we need to end the stigma associated with that. And I can't think of a better guy to do a podcast with than him in terms of discussing that reality with people.

51:57 Yes. Love it, man. And uh I know you got to run to Bloomberg. Um I appreciate you doing this, dude. I would love to do a round two in the future if you're anytime. You're you're the man. You did you did a lot of research. I'd like to have you come on open book for my uh I want to read your books and have you come on and we'll have a spirited conversation. Let's do it, man. Let's My [ __ ] lighting was awesome. I'll try to I'll try to look as good as you. You got to get hook me up. Just letting people know that are listening to this on audio. You're missing this lighting moment for me. I think the lighting is [ __ ] fantastic in here. No, you look good. You're ready for TV. So enjoy the TV run TV hit you're about to do. And I meant it, man. I'd love to continue our dialogue and let's let's let's keep this thing going. All right. God bless you, man. Awesome.

Questions about this episode

Who speaks in "Anthony Scaramucci Unfiltered: Wall Street, President Trump, and Building Confidence"?

Ryan Hawk (Host), Anthony Scaramucci (Guest).

What is "Anthony Scaramucci Unfiltered: Wall Street, President Trump, and Building Confidence" about?

The discussion highlights Anthony Scaramucci's experiences with leadership, resilience, and personal growth after his abrupt firing from the Trump administration. It explores the interplay between power and ego, the importance of self-acceptance, and the challenges of maintaining confidence amid adversity.

What is mentioned in this Ryan Hawk episode?

8 people, works and ideas are mentioned, including Donald Trump, Skybridge Alternatives, Amazon, Derek Jeter, Salt Conference, Alonzo Kahoon. Each one on this page links to its own page with every episode that mentions it.

How long is "Anthony Scaramucci Unfiltered: Wall Street, President Trump, and Building Confidence"?

The episode runs 53 min; the transcript is about 10,396 words in 68 timestamped sections.

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