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Podcast Summary: The Learning Leader Show With Ryan Hawk - Episode 643: Anthony Scaramucci
Overview In the 643rd episode of *The Learning Leader Show*, host Ryan Hawk converses with Anthony Scaramucci, the former White House Director of Communications under President Donald Trump. The discussion covers a wide range of topics, including leadership, personal growth, resilience, and the dynamics of power in society.
Episode Highlights
Anthony Scaramucci's Background
- Served as White House Director of Communications for 10 days in July 2017.
- Founder and managing partner of SkyBridge Capital.
- Involved with the SALT conference, which fosters connections among diverse leaders.
Key Themes Discussed
- Leadership Through Service
- Authentic leadership is about making others successful, not seeking personal glory.
- Example: Derek Jeter's team-first mentality highlights the importance of serving others.
- Flexibility and Decision-Making
- Football experience taught Scaramucci the importance of adapting plans quickly under pressure.
- Emphasizes that one must be prepared to change strategies when necessary.
- Resilience Through Adversity
- Early life challenges build resilience for future challenges.
- Scaramucci reflects on personal setbacks as essential learning experiences.
- The Confidence Battle
- Self-belief is foundational to personal and professional success.
- Quotes Henry Ford: "If you think you can or you can't, you're right."
- Accountability in Relationships
- Accountability played a critical role in Scaramucci's marriage recovery.
- Importance of taking ownership of one's mistakes and working towards improvement.
- Life Coaching vs. Therapy
- Scaramucci prefers life coaching for its focus on progress rather than past issues.
- Life coaching encourages individuals to explore actionable steps for self-improvement.
- Forgiveness as Liberation
- Forgiveness helps in letting go of burdens and moving forward.
- Scaramucci emphasizes the necessity of forgiving oneself to avoid regret.
- The Comfortable Outsider
- Being a "comfortable outsider" provides a unique perspective and relatability.
- Scaramucci views himself as an outsider in elite circles, which helps in navigating them authentically.
- Intellectual Curiosity and Neuroplasticity
- Encourages blending curiosity with the ability to adapt, enabling effective navigation across various social and professional contexts.
- Pivot for Survival
- Discussed adapting business strategies, including a pivot to Bitcoin during a crisis.
- Importance of innovation and reinvention in maintaining relevance and success.
Personal Insights
- Scaramucci shares his personal journey of overcoming marital challenges and self-improvement through life coaching.
- Encourages listeners to work on themselves continuously and avoid a victim mentality in the face of adversity.
Closing Thoughts
- Scaramucci emphasizes the importance of personal accountability, resilience, and the willingness to adapt.
- The discussion serves as a reminder to embrace life's challenges and foster growth through service, forgiveness, and continuous learning.
Key Quotes
- "If you're on the team, it's not about me, right? It's about you."
- "The first fight is with yourself."
- "Forget about the past. What the hell are we going to do today?"
Conclusion This episode is a rich conversation that provides insight into the mindset of a leader who has experienced both the peaks and valleys of power. Scaramucci's reflections on leadership, accountability, resilience, and personal growth offer valuable lessons for anyone looking to improve their leadership skills and navigate challenges with confidence and charisma.
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Transcript
Automatic transcript. May contain errors.0:00This episode is brought to you by Insight Global. Insight Global is a staffing and professional services company dedicated to being the light to the world around them. If you want to learn more about the CEO, Burt Bean, and Chief Revenue Officer, Sam Kaufman, check out episode 424. We had a fantastic conversation talking about my partnership with the great people at Insight Global. If you need to hire one person, hire a team of people, or transform your business through talent or technical services, Insight Global's team of 30 ,000 people around the world have the hustle and grit to deliver. Hiring can be tough, but hiring the right person can be magic.
0:45Visit insightglobal.com slash learning leader today to learn more. That's insightglobal.com slash learning leader.
0:57Welcome to the Learning Leader Show. I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now, on to tonight's featured leader, the Mooch, Anthony Scaramucci, served as the White House Director of Communications for President Trump from July 21st to July 31st, 2017. Yes, 10 days. He was at Harvard Law School with President Obama and First Lady Michelle Obama. He's the founder and managing partner of Skybridge Capital, and he's the founder and chairman of the SALT Conference. He's done a lot.
1:41During our conversation, we discussed what he learned from getting fired by President Trump after working for him for just 10 days. Then, why his wife filed for divorce and how he was able to do the work to reconcile and turn a bad situation into a good marriage. Then we talked about the importance of finding your superpower. And he shared what he feels mine is as well as his and how they're the same thing. And then I think you'll just enjoy his willingness to say exactly what's on his mind at all times. I don't necessarily think this will be for everyone, but I think some will absolutely love it.
2:29Ladies and gentlemen, please enjoy my conversation with the Mooch, Anthony Scaramucci.
2:39Anthony, 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? 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 bitch and i'm just wanted you to acknowledge my lighting before we started are you wearing makeup no no no makeup i swear no i got good skin okay those are 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 going to i'm going to teach you my tricks okay afterwards you're gonna send me where you go okay i need i want to look like you all right okay you can 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 just wanted you to acknowledge can you just send 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.
3:50I talked to Paulina Pompliano, who did a big, deep dive on you, and she's amazing. She's been on the show. So is her husband, Anthony. 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? I got hurt, by the way. 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 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 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 and the people you know you know what were their blitzing or what their formation was.
4:43We did a lot of audibles at 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 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 Derek Jeter said it better than anybody. So I'm going to paraphrase from him and quote it back to you. But one of the key things that makes a good leader is service.
5:20And 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 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.
5:56You know, you've got your little cheerleader girlfriend out there and she's waving the pom poms 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 Vinny Testaverde, that son of a bitch. Okay. He played for Sawanica High School. He went on to University of Miami, ended up playing for the Jets, Cleveland Browns. He was a monster in high school. He was a year older than me. And his team, Sawanica 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 Testaverde, that son of a bitch.
6:35And I had to get my ass kicked. Here I was, this little 5 '9", squirty, Doug Flutie-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, hey, you got to get over that, right? That's called resilience, right? Such a good question. But that's how I would unpack that for you. 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.
7:15I am curious about your story. Let me tell you something, 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? Can I get to the game? Can I believe in myself enough so that I'm standing next to someone else who believes in themselves that I can compete? Because if you go into the game mentally thinking that you're not there, you're not going to be there. Henry Ford had one of the best lines in civilization. You want to hear the line?
7:52He was a son of a bitch, 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. You've heard it before and you know exactly until you got to get in the mindset. OK, you're going to fire me from the White House. No problem. I'm a crash dummy. I'm mayhem from the Allstate commercial. I'll fly through the window and I'm going to get up and dust myself off. I'm going to keep going because that's my mindset. 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.
8:29It'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 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, you know, 14 months with Donald Trump on the campaign. I work with him on the executive transition team. I had a good relationship with him. Jared Kushner once said that Trump likes talking to you because you remind him of his dad. You made your money on your own.
9:09You don't give a shit. You're not trying to kiss his ass like these other people. And you tell him right to his 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 was a little bit more brittle in the White House. And so you needed to be a lot more obsequious. And I didn't have that gene. Why would that be any different? I think the job, the personality, look, you get in that job. Barack Obama once said about that job, it magnifies your personality. And so I think in his personality was, I'm right. My instincts are better than everybody else's.
9:47You better kowtow 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 he 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 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 shit about that trump trump laughs about stuff like that.
10:24I 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. I'm just looking out for your interest. And don't, don't, don't tell me that. Don't tell me that. And then Monday I get fired. That's fine. Listen, I mean, you're asking me about the 21st of July.
10:55I 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. 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. Trump has done something politically masterful. Again, you can like Donald Trump or dislike him. I'll just tell you what he did.
11:32He 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 it's now full MAGA. You can't be on the team unless you're full MAGA. And of course, to quote Donald Trump himself, well, what is full MAGA? Whatever I say it is. So 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.
12:12The country's not that far of the left. And so 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 who won the Democratic primary in New York City. He's a hard left, progressive, devout socialist. I'm just going by what he says, not me. The country doesn't want that. 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.
12:51And so, you know, it is what it is, you know. Well, it feels to me, it seems like we're somewhat aligned. Elon Musk, in fact, when he was kind of going through that little breakup stage with President Trump, 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, that's somewhere in the middle. 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 said, yes, absolutely. We feel like we don't have a home. We're somewhere in between. What do you think about that?
13:26You know, I'll give you bad news. And Elon Musk is right. And we do need a third party. And if anybody can 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 is radical moderates, radical centrists that want to reform the government and not do what's happening now. This is a little bit longer of a conversation, so forgive me. But what happened in 1992 is a gentleman by the name of Ross Perot ran as a Reform Party candidate, won 19.9 percent of the vote.
14:08So 33 years ago, the Republicans and the Democrats got the shit 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. They've squashed 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 gerrymander districts. They allowed each other to stay in this permanent perpetuation of power. So, you know, Chuck Grassley's like, I think he's like six or 700 years old. You know, he's still in Congress.
14:48I mean, I don't know. I mean, I don't know. He'll be running 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 I'm like, I don't have to serve the people. I can do whatever the hell I want. And 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 specter of populism.
15:23The people have said, hey, man, this sucks. You guys are taking care of the fat cash. You're taking care of the rich. What about me in the lower or middle class? What about my rising living standard? I was once in an economically aspirational family as a blue-collar person, and now these families are economically desperational. Fuck you guys. And so 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, and you need some very cunning people. 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?
16:14The kid, the 33-year-old kid that won in New York, he's a charismatic kid. The policies are misguided, but the social media was A+. You know, the little clips and this and that, and he energized a group of people. and Andrew, my friend Andrew Cuomo was running a campaign that was more politically consultant driven, was more advertising and mailer driven. And we're in a digital world now, you know, and this is why, uh, that's why Bitcoin is going to do well. Now the old folks don't see it, but Bitcoin is 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 that's a mouth that's a mouthful i appreciate it i appreciate my lighting hawk forget about it look great how's the lighting you look amazing okay uh can we get can we get personal for a second anything you want me we can talk so so i love i love your show and it's a i'm flattered to be on thank you there so there is a time where based on like your devotion to your work it at least from what i read you can correct it if it's wrong.
17:23Your wife was going to divorce you and was like, Anthony, peace out, dude. I'm not doing this anymore. But then at her insistence, again, correct me if this is wrong. She's like, you need to work with somebody, get a life coach or somebody like that to help you. Is that true? 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. So that was close to not continuing. What did you do to fix that? So not only is everything you said true, but it's worse than that. And so, yeah. So I would say to you that I owe my wife, Deirdre, a debt of gratitude for actually really loving me because I was off the rails on a few things.
18:06It wasn't just the political ambition. 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 hot-headed italian group of people it was sort of like a shot across the bow and she's like hey i'm not having this so if you love me get your shit 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.
18:46You know, there's a, there's a great cliche. Are you married Hawk? 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, you can, you know, meaning you can be right. You can be right. Like in righteous, you know, your husband's wrong and you're right. And then you have divorced or you can be right, or you can be married. Meaning you have to, I'm sorry, go ahead. 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 vote it's good insight you know 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 yeah 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 not going to have perfect harmony there's no such thing except in a fairy tale yeah you know we were both on our second marriage um love each other uh i was over my skis i mean she hated trump she probably hates trump as much 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 shit right i mean they are they are still married i think yeah but she fucking hates him and she doesn't live with him and you know he said he more 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 well 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 like the policies i don't like the bellicosity 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.
21:00But back on the target, Deirdre and I heading for a divorce, did a perp walk in the Nassau County Family Court together. 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 fucked 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 something to me 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 day 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 podcasts are you or are you not accountable like sometimes we go into the 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 Greene's books have done so well, you know, the 48 Laws of Power.
22:21And I've interviewed Robert on my podcast, and I love Robert. 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 become more direct in terms of what my feelings were. And we turned our marriage around. Now, was it perfect in the beginning after the fight started, the first six, eight, 12 months? No. But is it a way better marriage, a stronger marriage today, eight 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.
23:05But 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, don't make everything in your life disposable, particularly the things that matter. And if you're working on yourself, one thing I have found with my adult children, because I've obviously had a failed marriage. My first marriage was a failure, but I've got three beautiful adult children. I think they give you the benefit of the doubt if you're working on yourself.
23:39I 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 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. And genuine curiosity. What are you currently doing to still work on yourself? Well, you mentioned my life coach. I have a life coach.
24:16Oh, you're still? Yeah. Yeah. I speak to him once a week. Sometimes I ask him to speak to my kids or maybe even an employee or, you know. Is that like therapy? I'm fascinated by like how a coach works with a person. Like what do you, does he or she give you prompts? How does it go? Such a great question. 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 Cajun who's my life coach and I'm happy to mention his name in case people want to use him easy to find first name Alonzo last name Cajun C-A-H-O-O-N I just say that Scaramucci sent you okay he'll let out a laugh because 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?
25:07What are you going to do? We're going to relitigate the past all day and discuss what went right and wrong. Who gives a shit? 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 how are we going to live with a cup overflowing with optimism about the world? there's a lot of reasons to be pessimistic that's life you know you're the human condition the ancient greek 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 greek say that's your life you're going to get a package of tribulations in your life some of them are joyous and some of them are tragic.
26:02And by the way, it's going to be tragic. Okay. You're going to end, you're going to meet your own demise. You're going to have to say goodbye to people you love. And so you have to accept that. 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, his 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 three days later and he was here for 40 days and he and he's gone you know my point my point being you're gonna die okay so what are you gonna to do.
26:55Face the music in your life. Enjoy your life. Embrace your life. 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. Let me handle it with some level of kindness towards others.
27:29I think that's the messaging of life coaching versus my dad hit me when I was eight and so now I'm fucked up. I don't know. 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 impact, 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.
28:05How did that impact? I'm impressed that you did your homework. You know, I did a podcast with my brother in 2016, which I always refer to people to about addiction. And so my brother became a cocaine addict, 40 years cycling in at a cocaine, maybe seven or eight rehabs. He's 63 today, doing well, very smart guy, lovely guy, sensitive guy, but a real guy, someone I love very much. He became a cocaine addict. I became a different type of a holic. I became a work holic. And so, yeah, my dad was rough on us. 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.
28:49Who the hell knows what happened to my dad when he was a kid? You know, who the hell knows? I can't tell you. But for me, 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 harshly. Okay, so whatever was going on with my dad, maybe depression, a lot of anger in human life is represented. 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.
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29:38I mean, look, everybody can have a temperamental blow off. I'm not saying that, but I'm saying a consistent level of anger is usually a sign that 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. 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 brained the president or John Kelly or anybody for getting fired. I got fired because I wasn't serving the president the way he wanted me to. He fired me.
30:13So 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 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, is I would say to people, human frailty and not judging it is not just you judging others, but also yourself. The shit that you're doing that you don't like, the shit 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.
30:52Again, that helps their careers. It helps their relationships. It helps their business life. But yeah, my dad was very rough on us. He was rough on my mom. They were in a traditional Catholic marriage, so no one was going anywhere. And that's where we are. 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 it's important.
31:30And by the way, that podcast my brother and I did, 500 ,000 people have listened to it. I was in an airport once when I was passing my luggage through 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. him, he goes, you know, I'm seven years clean. And 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, 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.
32:16You know, there's a, 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 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 I think you also just taking ownership over the situation, because I know there are some who would choose to use that and have a victim mentality and then go act out in a bad way and cause harm to others.
32:50Ed Latimore was on this podcast and he grew up in a really tough situation. Mom's a drug addict selling drugs. 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. And I'm like, I like that. One of the things about you, Anthony, is that you are a very powerful person and you've been surrounded by power a big chunk of your life. You got fired by the most powerful person in the world. 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 kind of bob and weave amongst powerful people and continue to rise up, which you're doing as we speak.
33:38When you think about power, how have you been so good at managing egos and people with immense power in the world? 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 probably hesitating because I really want to be thoughtful about this. I guess what I would say to you is, 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, it's what I would say to people, find your superpower. Okay. You're a great interviewer. You've got great insight. You understand leadership. You're fascinated by it.
34:22I 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, meaning you can adopt and change, okay, then you can move in various circles. 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. The flip side is the people that are meeting at the World Economic Forum, guess why? You're the clamors. You know, better or no worse. You know, there was a kid who was a very smug kid I was in law school with.
35:04And he was, you know, some kind of intellectual bullshit 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 fucking 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, in high school, but because of their financial limitations in the family and the way they thought about things, hey, you're joining my sheetrock business.
35:38Okay. And so cool 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 wearing at my first Goldman interview. I was fully flammable Ryan Hawk for my first interview at Goldman Sachs. If a match went off, the whole thing would have caught on fire. I had a polyester shirt on. 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 ever met here at the Harvard Law School. So I can't invite you down to Goldman Sachs dressed like this.
36:14And I looked at him. I was like a beet red. I was so embarrassed. He said, you got to go to Brooks Brothers, buy yourself some natural fiber clothing. Okay. I remember calling my mother. My mother's like, he doesn't know what he's talking about. 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 the one last thought. Okay. I'm a comfortable outsider.
36:49I'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 blue collar neighborhood that went to a public high school, K through 12 public schools, and has some reasonable brain capacity and built a couple of businesses. But I'm not an insider, but I'm comfortable with it. 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 the 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.
37:46They're not going to let me in to be a member. And I can 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. I did. I was, I actually, Michelle Obama was a couple of years ahead of me. Sort of weird. So she was class, 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. And so I didn't really know them. I mean, I'm not going to BS people.
38:24All the faculty when he was president said they taught him, which was 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, senator. I mean, he was senator at the time. I said, Senator, I got a big check in my breast pocket here. 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?
38:58Well, he looked at me and 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 ripped the check up. Of course, I had another check in my wallet. I doubled the amount of the check and I handed it to him. And, you know, but he was very nice to me. I went to a couple of Christmas parties at the White House during his term there. And I like him. I think he did some things that he feels bad about today.
39:30I 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. but you know, listen, it is what it is. I think he generally did a good job. Remember we were in the midst of a real bad crisis, the global financial crisis, and he was a thoughtful guy, smart guy. And I think he, I think he was a pretty good president. Changing gears a little bit. One of the things that you did, I believe this is 2008 that I like is you started hosting events, specifically an event, I believe the sky bridge alternatives, assault conference where you gathered kind of people together.
40:09And I love this idea of bringing curious, thoughtful people together and creating collisions so that we could have conversations and learn through those things. Can you walk me through this idea that you had in 2008 to host this event and how it became like 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 fault leadership event. And some kid said to me, sir, could you explain to me your strategy and your visionary genius to create SALT?
40:50And 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%. 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 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.
41:27I went to the Encore Hotel, which is attached to the Wynn, and we were getting rooms for $99 in 2009. That's how bad the situation was. And so this was an accidental survivor strategy. This was a pivot that we were making in order to stay in business. This was not some mastermind plan, Ryan. Moreover, during COVID, 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 business. We pivoted into digital assets. You got over a billion dollars of Bitcoin-related assets on our balance sheet right now, almost nine figures of digital assets on our corporate balance sheet.
42:17I'm talking about the balance sheet of the portfolio, over a billion dollars in Bitcoin-related assets. that didn't exist five years ago for Skybridge. So why do we do that? Again, for survival. 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. Say, you know, we cut down these trees. We're dropping off four pound books stained with yellow dye. 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.
42:55Wolfgang Puck, who's a brilliant restaurateur, 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. Restaurants 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. I can eat 30 Twinkies at age 15, 30 Twinkies. Trust me, because I did it. Eat 30 Twinkies, not gain an ounce, and go out and play football. No problem. I can't eat 30 Twinkies today at age 16.
43:37Well, 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 adapt, 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 that was my kind. That's awesome. That's those positive externalities are good karma and they're good for your overall relationship building?
44:17Well, I just think it's a great idea to bring 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 life, in my experience, in my business, it feels like so many good things have happened from bringing people together and from relationships. That's how all this stuff really happens. And there's another event I recently saw you giving going to talk about the sun valley conference i was it maybe 1999 jeff bezos was speaking yeah and i remember i feel like you were like god i gotta invest in that guy but then you changed your mind because warren buffett spoke after him and was that like a teaching moment to trust your gut i'm curious about what happened you did a lot of research man you did a lot of research i'm impressed talk okay thank you yeah no you did a lot of real life telling i tried to tell the story that.
45:08Look, I missed a lot of the tech boom. By the way, Warren Buffett is the man. I attribute his teachings and writings to making my family financially independent. But like Warren Buffett, I've got a lot of things wrong in my life. 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. 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 car that's what we're doing yeah okay get the fuck 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 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.
46:09Bezos gave, he's my age, by the way, you know, he's born in January of 64, like me, 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 bookseller. I mean, I am a bookseller, but I'm not going to be just a bookseller. I'm moving these books around because they're roughly the same size, roughly the same weight. I'm trying to reverse engineer and dot plot where the warehouses should be.
46:49I'm going to build an everything store. And by the way, if you invest in this thing, maybe take 10 or 15 years, I can make any money with me. I'm thinking about this over 10 or 15 years. And then when I hit the spigot, 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 one-to-one to people. This was a B2C move that was absolutely brilliant. And Buffett said something after he was done speaking, I was like, okay, Buffett's always right.
47:28Let me rip this up. I 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 in this. Oh, by the way, can you believe that this guy's valuation, his market capitalization for Amazon is bigger than Sears Roebook, the storied Sears Roebook with all of its bricks and mortar retail everywhere? and I was like yeah of course and I don't have the exact numbers but I want to say and Frank Quattrone 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 Grok if you put$10 ,000 into Amazon on the IPO what's it worth today?
48:12I 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 percent one period of time where you lost 90 and very few people held it bezos did but very few people held it from day one to today but he's a genius and he's a great executor and you have to acknowledge i made a mistake i missed it it was right there it was right on the t for me and i could hit it over the fence but i missed it and so we 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 I don't want to miss Bitcoin.
48:53You know, Bitcoin is me sitting there in that meeting in 1999. Yep. I know we got to run, man. You're doing podcasts and most recently, this one called Lost Boys with our mutual friend, Scott Galloway, who's been on three or four times and will be on again soon to promote this next book. what's that like been with scott and your banter you guys have both these great personalities you're not afraid to speak your mind and i i gotta imagine that's gotta be fun for you guys so
49:26i 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. He's not an us versus them guy. He's a inclusive guy. And he's also honest, you know, and what I love about him, and 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 Ed Elson, they do a brilliant job on that podcast. He's also friends with Kara Swisher on the Pivot podcast. I know Kara. And so a couple of mutual friends put us together.
50:07And 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 him, why don't you and I do a limited series? you 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 Rees we'll interview sociologists we'll interview people that are studying this problem we'll interview people that think we're full of shit that don't agree that there is a problem and we'll put it out there into the public domain so that we can raise awareness because like that podcast I did with my brother related to addiction disorders, let's talk about these things.
51:03Let's remove the stigma of what these things are and what they 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 TikToker 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. 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.
51:50You'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 yes love it man and I know you got to run to Bloomberg. I appreciate you doing this, dude. I would love to do a round two in the future if you're game.
52:27You're the man. You did a lot of research. I'd like to have you come on Open Book. I want to read your books and have you come on, and we'll have a spirited conversation. Let's do it, man. My fucking lighting was awesome. I'll try to look as good as you. You got to hook me in with your people. Just letting people know that are listening to this on audio, you're missing this lighting moment for me. I think the lighting is fucking fantastic in here, no? You look good. You're ready for TV. So enjoy the TV hit you're about to do. And I meant it, man. I'd love to continue our dialogue and let's keep this thing going.
52:59All right. God bless you, man. Thank you, man.
53:05It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note. Ryan at learningleader.com. Let me know what you learned from this great conversation with Anthony Scaramucci. A few takeaways from my notes. Confidence and charisma. The first fight is with yourself. You have to believe that you can do the big thing. Henry Ford said, if you think you can or you think you can't, you're right. And I get this sense that Anthony has developed this charisma and confidence about himself to be brutally honest and just say what's true. and doing this kind of endears him to others and it makes you want to work with him.
53:50It's kind of cool. And then how he handled his wife filing for divorce. She said he was a complete mess. He took accountability for it. He worked on himself. He met with Tony Robbins. He hired a life coach and he continues to work with his life coach to this day. He said therapy is regression. It's all backwards. Coaching sessions for him are about progression. They're about movement, moving forward, being an optimist. I liked his viewpoint there. And then find your superpower. He mentioned that ours is the same, which is intellectual curiosity plus neuroplasticity, meaning you're willing to have an open mind, to change your mind, to ask questions, to listen, to be a learning leader.
54:38dare I say. Once again, I want to say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of The Learning Leader Show with Anthony Scaramucci. I think the mooch will help you become a more effective leader because you continue to do that and you also go to Spotify and Apple Podcasts and you subscribe to the show and you rate it hopefully five stars and you write a thoughtful review by doing all of that you continue to give me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so, so much.
55:15Talk to you soon. Can't wait.
From the publisher
Go to www.LearningLeader.com for all show notes
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Anthony Scaramucci served as the White House Director of Communications for President Donald Trump from July 21 to July 31, 2017. He was at Harvard Law School with President Barack Obama and First Lady Michelle Obama. He's the founder and managing partner of SkyBridge Capital. And he's the founder and Chairman of the SALT conference.
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Leadership through service: True leadership isn't about personal glory but about making others better and helping them succeed in their roles. Derek Jeter exemplified this by never caring about personal statistics, only team success. "If you're on the team, it's not about me, right? It's about you. How am I gonna make you better? Or how am I gonna make you feel good about your role? How am I gonna get you to think that I'm here to help you?"
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Flexibility and decision-making under pressure: Football taught Scaramucci the importance of reading situations quickly and making audibles at the line of scrimmage - skills that translate directly to business and life leadership. "You can't just say, okay, here's the 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."
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Resilience through adversity: Getting "your ass kicked" early in life builds the resilience needed for future challenges in business and politics. Early defeats teach you how to bounce back from failure. "That's called resilience, right? You gotta get over that... That's how you gotta get your ass kicked. Here I was... and I just remember feeling so puny... So how you gotta get over that."
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The confidence battle starts within: The first fight in life is with yourself - believing you're good enough and worthy to compete. Henry Ford's principle applies: "If you think you can or you can't, you are right." "The first fight is with yourself. Am I good enough? Am I worthy? Can I get to the game? Can I believe in myself enough so that I'm standing next to someone else who believes in themselves that I compete?"
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Accountability in relationships: When Scaramucci's marriage was in crisis, taking full accountability for his mistakes rather than deflecting blame was crucial to rebuilding the relationship. "I owe my wife Deirdre, a debt of gratitude for actually really loving me because I was off the rails on a few things... she's like, Hey, I'm not having this, so if you love me, get your shit together."
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Life coaching vs. therapy approach: Life coaching focuses on progression and future action ("What are we doing today to be better?") rather than regression into past issues. "I feel that therapy is a regression. Life coaching is a progression... forget about the past. What the hell are you gonna do? What are we doing today to make yourself a better person?"
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Forgiveness as liberation: Choosing to forgive both others and yourself removes the "millstone of regret" that weighs you down and prevents forward progress. "I can take that millstone of regret and leave it behind me, take it off of my neck and leave it behind me... human frailty and not judging it is not just you judging others, but also yourself."
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The comfortable outsider advantage: Being comfortable with your outsider status while still being able to operate in elite circles provides authentic confidence and relatability across all social levels. "I am a comfortable outsider. I'm not an insider... but I'm comfortable with it. You know, like guys like Trump or Rudy, they're uncomfortable. Outsiders... But I'm a comfortable outsider. I don't need to do that."
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Intellectual curiosity + neuroplasticity: Combining genuine curiosity about others with the ability to adapt and change allows you to move successfully between different social and professional circles. "Find your superpower... I think your superpower is very similar to my superpower... intellectual curiosity. And so if you can blend intellectual curiosity with neuroplasticity, meaning you can adopt and change... then you can move in various circles."
Pivot for survival: Successful businesses and careers require constant reinvention. SkyBridge's conference business and pivot to Bitcoin were survival strategies that became major successes. "We were going outta business... This was an accidental survivor strategy. This was a pivot that we were making in order to stay in business. This was not some mastermind plan."
