What the World’s Richest and Most Powerful People Get Wrong (with Stephanie Ruhle)

Stephanie Ruhle https://www.instagram.com/stephruhle/?hl=en has spent her career with a front-row seat to some of the wealthiest and most powerful people in the world. In today’s episode, she talks with Ryan about what they often misunderstand about success, what happens when having everything still isn’t enough, and the cost of staying at the top. Before becoming a journalist, Stephanie Ruhle https://www.instagram.com/stephruhle/?hl=en spent 14 years working in finance. She later joined Bloomberg Television, hosted The 11th Hour, and now hosts Money, Power, Politics with Stephanie Ruhle on MS NOW https://www.ms.now/money-power-politics. Watch Money, Power, Politics with Stephanie Ruhle on MS NOW https://www.ms.now/money-power-politics! Watch Stephanie Ruhle interview Ryan https://www.youtube.com/watch?v=vGXvQqurY-Y at The 92nd Street Y: https://www.youtube.com/watch?v=vGXvQqurY-Y Follow Stephanie Ruhle https://www.instagram.com/stephruhle/?hl=en on Instagram: https://www.instagram.com/stephruhle/?hl=en 🎟️ DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️ AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/ https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. -- Wealthfront’s high-yield cash account: https://www.wealthfront.com/stoic This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at wealthfront.com/promo-terms. The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”). Wealthfront Brokerage does not pay interest. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Instant and same-day withdrawals use the Real-Time Payments (RTP) network or FedNow service. Transfers may be limited by your receiving institution, daily caps, or participating entities. New Cash Account deposits have a 2–4 day hold before transfer. Wealthfront does not charge fees for these services, but receiving institutions may impose an RTP or FedNow Fee. Processing times may vary.. Fees & Eligibility requirements may apply to certain checking features. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:15Ryan Holiday?

  We think it's going to give us power, right? We think it's going to give us autonomy. We think it's going to give us control. This is what money and success in politics are about. Except, this goes all the way back to the Stoics. It rarely ends up that way. Like, you think you're going to have the job. And in fact, the job ends up having you. You think you're going to have the title. The title ends up having you. You think Marcus Aurelius has it made. And in fact, Marcus Aurelius is probably the least free man in Rome. That's the fascinating thing about Epictetus's writings is like, Epictetus is a slave in the court of Nero, but he looks around and he realizes that he has it better than most of these people.

• 1:01Ryan Holiday?

  Certainly has it better than the emperor, who is vain and paranoid and delusional and insecure and a slave to his appetites, a slave to his ego. Like, we think this thing is going to give us control over the world. And in fact, we are handing over control. Money, power, and politics, these are perennial themes in the Stoic writings. We have the Stoics in positions of power. We have them on the outside lamenting and philosophizing about the people in power. Seneca is fascinating because he's both, right? He is consul. He's the advisor to the emperor.

• 1:45Ryan Holiday?

  He is rich. And he's also incredibly critical of fellow Romans who are obsessed with success, who are obsessed with money. You know, at one point, he says, slavery resides under marble and gold. He never really comes out and explains his own experiences, but we get the sense that he's speaking from experience. And certainly, his plays are incisive cultural commentary, although he couldn't come out and say certain things. His plays are cultural commentary on all about this. That's what we're going to talk about in today's episode. Stephanie Ruhl has spent a career around some of the wealthiest and most powerful people in the world. Before she was a journalist and a television host,

• 2:30Ryan Holiday?

  she spent almost 15 years working in finance. And then she joined Bloomberg Television. She hosted the show The 11th Hour, which I've been on a couple of times. And now she hosts Money, Power, and Politics with Stephanie Ruhl on MS Now. She has interviewed everyone. Donald Trump, Joe Biden, Kamala Harris, CEO of JP Morgan Chase, Jamie Dimon, obviously, the New York City mayor and the founder of Bloomberg, Michael Bloomberg. And so I wanted to ask her about that, you know, with this new show, Money, Power, Politics. That's what I wanted to talk about because these are perennial themes in Stoic philosophy. Stephanie and I are talking about what money can and can't solve, how the pursuit of success can become its own form of captivity,

• 3:15Ryan Holiday?

  and why checks and balances are there not just to protect the people, but to protect the leaders from their worst instincts. I love talking with Stephanie. As I said, I've been on the show a couple of times. She interviewed me last year at the 92nd Street. Why? We had an amazing conversation. I'll link to that in today's show notes. You can follow her on Instagram, @stephruhl. And watch the show, Money, Power, Politics with Stephanie Ruhl on MS Now. I think you will like it. Let's just get into it.

• 3:43Ryan Holiday?

  So I thought we'd start with money. My question for you is you've interviewed some of the richest, some of the most successful people in the world, people in charge of enormous companies, people who employ thousands and thousands of people. And I'm sure you've just met them in New York. I'm curious about the idea of like, what problems can money solve? And what problems can't it solve? Like, if you heard the idea, like, if money can solve your problem, you don't have a problem. But we still have problems. And so I'm curious about that.

• 4:13Speaker 01

  Okay, so money cannot buy you happiness, but it can definitely afford you freedom. And what I would say about money and the super important part about it is, when you have it, and I'm not even saying a huge amount, what it does, Ryan, is create this cushion, right? So when you think about industries or people who face the most abuse at work, the most harassment at work, it's the people who have the lowest paying jobs, the most vulnerable communities, who aren't in a position where they can say, I want to take this job and shove it. And so, you know, what I really say especially, and we'll go to the top, top, top people next, but sort of young people. I'm not saying, don't go follow your dreams.

• 4:56Speaker 01

  But I am saying, please do what you can to have a job and work really hard to cover your rent and have some savings so you can pursue your dreams while sort of walking up the stairs or down the stairs and not jumping out of the window, right? So for me, I worked in investment banking for 14 years before I made the transition into TV. And it's funny because when I made the move, you know, there are in the last 10 years, so, so many people, you know, especially women have said like, how did you do it? I want to make the switch and so on and so forth. And then when I say out loud, oh, I took a 90% pay cut. Everybody's like, oh, my God, forget it, forget it, forget it. And sort of the beauty about that is if you save that money,

• 5:39Speaker 01

  and I'm not saying saving is easy, but if you save that money, it gives you the flexibility that you could sort of turn to the right or turn to the left and make better decisions. Now, the most successful people that I've ever worked for or interviewed, and I mean like some of the wealthiest people in the world, they're not people who said, I've made enough money. But they're people who changed the measure and stopped just measuring themselves based on how much money they have. Because if all you do, Ryan, is focus on the climb, well, then think about how exhausted you're going to be. The climb never ends, right? Because you achieve a goal and then you reset and you climb again. You climb again, you climb again. And some of the people that I would say have sort of,

• 6:25Speaker 01

  I don't know, maybe disappointed me the most would be like business idols of mine that I would think would be in, you know, the last quartile of their life, when they should be on like an 80,000 acre ranch in Montana, like surrounded by their family and blah, blah, blah. But instead, they're spending three of every four weeks on their G5, trolling the earth for the next deal.

• 6:50Ryan Holiday?

  Yeah.

• 6:50Speaker 01

  And I can remember, I don't know, maybe this was eight years ago or so, my husband and I walking into a hotel in Miami. And we ran into one of like the biggest guys in private equity. And it was somebody who my husband actually knew as a child, blah, blah, blah. And I remember looking at this guy because Andy and I, that's my husband, looked up to him in so many ways in business. And like, there he was at this hotel, right? In this wrinkled suit, sitting there sweating outside with a woman with a date who looked like she was maybe like 24 years old. And don't get me wrong, I'm sure he was like, look, I have the hottest woman here. This is amazing. And I'm looking at him and I'm like, Jesus Christ, like, what is he even talking to this woman about?

• 7:34Speaker 01

  But that's because this guy was so focused on the climb and the chits and like showing the world, here's what I've achieved and here's what I have. And if you actually have the understanding to say, I'm going to start viewing success, right? Part of my success as just joy. And if you actually make a list, when you think back on your own life, Ryan, and you say, what are my most joyful times? They're eating dinner at home. They are somebody pulling out a guitar when you're hanging out with friends, right? They're playing board games. And I'm not saying, oh, don't spend money, live a simple life. But it's the people who I've covered, who are super, super successful,

• 8:15Speaker 01

  but were able to press pause and actually count their blessings and say, hold on a minute, like, what gives me joy? Those are the people that I think have figured it out as opposed to others who just continue to be on the climb.

• 8:31Ryan Holiday?

  So there's two things there. I want to touch both of them. I think your career journey is interesting and it is something people miss. Cause people talk about following your dreams. They talk about, you know, taking the big risk. And that can be good, but it's, you're also very vulnerable if it doesn't work out. Like I wrote my first three books while I had a corporate job. You know, when I went to my publisher and I said, you know, I want to write about a, an obscure school of ancient philosophy. Like the reason I was able to take like a pretty significant decrease in the advance on my second book compared to my first is that I had this corporate job. Like I, I didn't, like how I lived was not going to change either way on this thing. And so I think what that comes down to is leverage, right? It's like-

• 9:14Speaker 01

  No, no, the beauty about that is you employed risk management. Okay. Risk management is like the unsexiest idea, but it's the most important. You wanted to pursue a dream and do something that was on the fringe or out of the box. So you did it and the only person who suffered was your sleep. Was you, you know, was you getting a good night's sleep? Because you were writing that book while you had a full-time corporate job. You risk managed it.

• 9:41Ryan Holiday?

  Yes. Yeah, it's like, uh, look, you all know, we all know, we, we live differently if we had a trust fund and it's like, this is a trust fund you give yourself, right? Like this is, this is, this is financial independence you are giving yourself rather than getting from a wealthy, you know, relative. And, and it can take time. And I do think, look, there's some, there's some careers where this is harder to do. Like, you know, like if it's being an actress or being a musician, maybe where, where the career is so focused on like a certain chunk of your, your late teens, early twenties, it's hard to go work in obscurity and then pivot towards that. But most things are not like that. And probably especially the kind of entrepreneurial things where the more experience, the more

• 10:26Ryan Holiday?

  funds you have, the more relationships you have, the more leverage you have to make your thing successful. You're not betraying your dream by putting it off. You're actually putting yourself in a better position to do it.

• 10:37Speaker 01

  Ryan, if I would have left banking when I was 23 and gone to journalism school, which I was thinking about doing, sort of one of the guys who ran fixed income at Credit Suisse where I worked, and I told him I was thinking about going to journalism school. He was like, are you crazy? You're going to have to go to a small market first. And let me be clear, your sensibility, Stephanie, isn't going to work outside New York, New Jersey or Connecticut. You, you don't sell in Tuscaloosa. And he also said, frankly, he said, you're 22 years old. There's not a lot of women in this business. You're really good at it. You can make a lot of money in the next 10 years. And what actually helped me, right? Because I didn't come right to NBC, I went to Bloomberg Television. And in business TV, the whole ballgame is booking guests.

• 11:22Speaker 01

  So because I spent 14 years in banking, when I made that transition to TV, my sweet spot was I knew all these people. It was very easy for me. I spoke their language. I understood the business and I could book really big guests because I knew them. I had that because I stayed in the industry so long. And, and you were just mentioning something that, that comes to mind. Opportunities don't always present themselves, right? So even in your job, let's say you want to get promoted to management, but you don't have any management experience, volunteer outside, right?

• 11:53Ryan Holiday?

  Right.

• 11:53Speaker 01

  Go volunteer for a nonprofit. And when you go to your review at the end of the year and you say, I want to manage a team and they're like, you have no experience managing a team. You can say to them, well, I've been organizing drop offs and pickups for city meals on wheels for the last 10 months and I'm doing it with a team. So for me, I started doing public speaking to get girls to study math and science, to get women to go into finance. So I was sort of building this public speaking stockpile. And that's even how I ended up. I was giving a speech for a nonprofit called the White House Project. And after there was a woman there who was like, wow, you'd be great on television. And, and, and so I was doing it out, you know, outside in the fringe. Now there's one thing, and I, this, I have a question for you.

• 12:36Speaker 01

  When you're pursuing a dream, here's something that people don't often tell you. Your peers will often make fun of you.

• 12:45Ryan Holiday?

  Sure.

• 12:46Speaker 01

  Or they're not even necessarily going to wish you well. And I think it's very, very embarrassing to pursue a dream. Pursuing a dream isn't just like having a, having a job is like, yeah, we all got to do this, we got to pay rent. Pursuing a dream is putting yourself out there and saying, world, this is who I am on the inside. I want to, I'm going to show you my vulnerability and try. And you think that everyone is rooting for you. And, um, there's a lot of people who will root against you or make fun of you. And if you let that get to you, you're a fool. Because when they're making fun of you, it's not you. It's their own shit. It's their own insecurity, right?

• 13:26Speaker 01

  And, and when you start to realize they don't really care about you, it's just, you're the thing to smack talk about for the moment. Once you can push that out of your mind, you can clear the path for yourself much easier.

• 13:39Ryan Holiday?

  Yeah, there's, there's a cringe factor to earnestly putting yourself out there. And then also like whatever it is that you're pursuing, you're going to be bad at it for quite some time, right? So I think there's two things. It's like, one, I'd like to be getting paid by someone else while I'm bad at something, right?

• 13:54Speaker 01

  Yes.

• 13:55Ryan Holiday?

  Like I, I don't want to be bad at it. And like how good I am at that thing is determining what I'm eating that day, right? That's the hard part. It's like trying to support yourself as a musician while you're putting in your hours to become a good musician. That's, that's a tough sell, right?

• 14:11Speaker 01

  Yeah. And especially think about if you have a family.

• 14:14Ryan Holiday?

  Yeah.

• 14:15Speaker 01

  You can quickly fall down a spiral of feeling self-indulgent and awful. If you're taking a risk to pursue a dream, when you're responsible for putting food on the table.

• 14:26Ryan Holiday?

  Yeah. So, so it's like, if you can be getting your hours and then also be getting paid to develop adjacent skills, that, that's kind of the, that's kind of the ideal scenario. And, and yeah, it's, it's not as glamorous. There's not the big gesture of like, you know, I'm quitting my job and going all in on this thing. But I do think it's a much more sustainable path and ultimately a more self-sufficient path, which is, which is what I-

• 14:49Speaker 01

  Yeah. I mean, the only person who suffers is you in that you're sleeping less, you're seeing friends less, you have less disposable income for things that you enjoy. But I would argue you're investing in yourself in the smartest, most responsible way you can.

• 15:04Ryan Holiday?

  Okay. So, so what you were talking about though, with some of the very wealthy, successful people you've seen over the years, it's funny, we think money is freedom and it can purchase freedom, but if actually the source of your kind of lack of freedom is not financially based, no amount of money is going to free you. Like there's this great line from Seneca where he's talking about this Roman general. And he says, you know, Marius commanded armies, but ambition commanded Marius. Right? And he's saying that like, this guy is so powerful and successful, you think, except he's not in his own power. Cause what he actually wants is more and more and more. And so you can see someone who has, you know, a billion dollars. And then for some reason you realize you're both attending the same conference.

• 15:49Ryan Holiday?

  You're like, what are you doing? Like, wasn't the whole point of becoming a billionaire not to have to go to shit like this? And, and you realize it's not.

• 15:57Speaker 01

  More importantly, those people, their status, their public status becomes everything. So their life becomes more and more and more expensive. So even though they could be worth 10x what you're worth and I'm worth, their life costs 15x what ours does.

• 16:14Ryan Holiday?

  Sure.

• 16:15Speaker 01

  Right? It's sort of like the, the, the Wall Street golden handcuffs that, you know, I remember when I first started in banking and you could actually see it, right? Like, so people would start and then they would buy an apartment and then they would buy a house in the Hamptons. And if they buy that house in the Hamptons, that house in the Hamptons has to have a manager. And oh, the guys on your desk that you work for, we're all going to buy in a syndicate, a racehorse. And once we buy that racehorse, we're going to join a hunting club. And once we join that hunting club, we're going to join a country club. And then you take a step back and you're like, hold on a second. I'm a public school guy from Jersey and all I ever wanted to do was not be bridge and tunnel. I just wanted to live in New York City. How did my cost basis fly out the window? And how do I have multiple?

• 16:55Speaker 01

  And so I just think you have to keep pulling it back in and saying, what is success for me? What is joy for me? What makes my life work, not my universe? Cause it's extraordinary when you look at people and to that point, you're like, what are you doing still in the hustle? And it's amazing when you actually look under the hood and the more successful people become, the more beholden they are to needing that paycheck because they felt like they needed their life and their lifestyle to ratchet up and up and up and up.

• 17:25Ryan Holiday?

  Yeah, it's, there's the keeping up with the Joneses element of it for sure with the, the lifestyle creep and now your monthly nut is X. And so, you know, you, you're running faster and faster to stay in the same place. But I think the, the real tragedy is kind of what you're talking about in that hotel or you see these people crisscrossing the globe to do more and more and more. It's not financially based. It, it is though, an inability to ever feel like they have enough and that they're good and that this was all for something.

• 17:55Speaker 01

  Ryan, when I remember looking at this guy, he almost looked like he was an empty shell, right? Just like trolling the universe like a vampire, like needing one more deal and one more deal. But the problem is each deal, right? Feeds you less and less. And you're like, how could this person that has everything still appear to be starving? Cause it's the vampire that needs one more kill. And you're going, for what? Your children's children will want for nothing? Find yourself a big beach house and watch some kids play in the sand.

• 18:33Ryan Holiday?

  It's crazy how timeless it is too, though. Like, it's like you read these ancient works and like they're lamenting people doing that 2,000 years ago. Like, that personality type of like, I've gotta stay in the hunt, I've gotta maintain my relevance, there's one more deal, you know, there's one more luxurious property that I want. Like, that personality has always existed and tragically probably always will exist.

• 19:01Speaker 01

  I think there's a place, we see it even more, though. So, right, so in my career, I've either worked with or covered business or politics.

• 19:09Ryan Holiday?

  Yeah.

• 19:09Speaker 01

  And if you think about the most successful business people or politicians, right, like, they're all in the hunt for money and power. And I think that there are lots of business examples where in the first half of their career, business people are making the most ruthless decisions, maybe, you know, having the sharpest elbows. And maybe when they get to that back half, they're actually taking their foot off the gas and saying, you know, how can I better the world around me? How can I have the best life? I actually think politicians are the reverse. Right? We have politicians who are in office in their 80s, right? If Chuck Grassley wins his next election, by the time he leaves office, he'll be 95 years old.

• 19:51Speaker 01

  And I'm not saying this specifically about Chuck Grassley, but, but what I've witnessed in politicians is, they haven't necessarily made the money where they've got that beach house. So for them, everything is about power. So as soon as they lose that position, and remember, in Congress, it's, it's amazing, the longer you're in office, right? Every time you win, you get, or you get a bigger position, a bigger leadership position, you get to trade offices on the Hill. You get to have a bigger office, a fancier office, a bigger staff. So that power mounting is everything. And they cannot leave office because without that job, who are they to the universe?

• 20:31Speaker 01

  And the sick thing is, then the older they get, the less viable they potentially are for the next chapter, which would be a media career. And so you watch these people in politics where you're going, why does this person want to still be in office? Right? The next most important thing they're doing is figuring out how are we gonna regulate AI? And so we've got people in office, they're gonna regulate the future, right? Every element of the way that we work, the way we live and the way we play, and they're not gonna live to see it. But they desperately need to keep that job because in their mind, without that power, what do they have? And so I take that same sentiment and I compare it to that same private equity guy

• 21:14Speaker 01

  sitting in that hotel and say, neither of those people or those personality types have ever prioritized, what is, what does my peace look like? Where have I actually derived joy personally? And the answer is, I don't think it's going to another committee meeting in Congress, and I don't think it's trolling for another deal.

• 21:36Ryan Holiday?

  Well, the, the tragedy of, of the political people that you talk to, you know, the business people tend to actually like what they do, right? Like, it's glamorous, it's luxurious, it's fun. You know, the weird part about talking to these politicians who hang on is that, like, the complaints are not far from the surface. Like, very rarely do you meet a politician, they're like, I just love it, right? They hate campaigning, they hate raising money, they hate the moral compromises, and then they will debase themselves to continue the thing because they dread, you know, that, that, they dread being the ex-senator from Nebraska.

• 22:13Speaker 01

  Yes, but, but debasing themselves, that's when you see them as the most compromised because they're like, what do I need to do to hang on to this position?

• 22:23Ryan Holiday?

  Yeah. Yeah, it's, it's a, it's a tragedy to not be able to be good with yourself, to be able to know, like, hey, I did it, and if I get to keep doing it, awesome, but at some point, you know, I do have to walk away from it. And here's who I wanna be, or who's, here's who I am without either the money, the title, or, yeah, the committee status or whatever. I think in politics, it's especially hard because, yeah, as you point out, the power compounds, right? Because the, the, the longer you stay in, the more seniority you have when your party is in power. And so you're like, hey, I, I sacrificed the first 30 years to be able to be in this

• 23:07Ryan Holiday?

  position, and now you're telling me to walk away. And yet, again, the timelessness of it, right? Like, if you described, you know, Joe Biden to, you know, a Roman historian 2,000 years ago, they'd be like, oh, yeah, we've seen, we've seen that guy a lot of times. Just like, they waited the whole time for their shot, and then they couldn't accept that they only got one shot, and now it was time to walk away on top. Uh, I'm gonna, I'm gonna roll it all on another go.

• 23:36Speaker 01

  And everyone else can see, it's time to walk away, but when you're that person, and you think about your sacrifice, or you believe your hype, you're not gonna walk away. But what's funny of the examples of politicians, and I, I never think of it until I'm in Washington and I see them, and when I remember, oh my gosh, they're not even home, right? They don't live here, this isn't their home state, this isn't where their grandchildren are, or even potentially their spouse. And I'm like, oh my God, they've been on a business trip for 35 years. And if you think about your own life, right? Like, I do love to travel, but I like to travel with my family, but the older I get, I just wanna stay home more. Right? Like, I want to go, you know, I wanna go to a live sporting event, a live concert,

• 24:20Speaker 01

  but I don't even wanna go to restaurants so much. I don't want the hustle and, but I, I just wanna be home. So it's when I see politicians and I remember, I'm like, oh my gosh, like, because I always see them at airports, and I'm like, they're not even home. Like, there's that person who's been doing this for decades with this little dinky carry-on that they're putting in the overhead, and I'm like, holy cow. For me, like, I stop at nothing. Even if I work a 15-hour day, I just wanna sleep at home and count all the heads in my house to make sure we're all sleeping there. I'm like, that's the opposite of what I want. But they're on these diamond-encrusted gerbil wheels, and they, they, they can't get off, or they've convinced themselves they can't.

• 24:59Ryan Holiday?

  Yeah, no, I saw John Cornyn getting off a Southwest flight at the Austin Airport a couple of weeks ago, and you just go, okay, you know?

• 25:06Speaker 01

  Exactly.

• 25:07Ryan Holiday?

  I hope it was worth it, bud.

• 25:10Speaker 01

  That's exactly it. It's exactly it.

• 25:14Ryan Holiday?

  And then the irony, though, this is, this is how we move the goalposts financially and career-wise. You'd think you'd go, okay, now he is really empowered. And now it's a, he starts out idealistic, you know, the machine gets a hold of you, but now that you're a lame duck. But no, because, as you said, there's either the media contracts on one side, or, you know, if I get too far outside the party, now they're not gonna take my calls as a lobbyist where I'm actually gonna cash in.

• 25:43Speaker 01

  And Ryan, I would argue, the latter is more than ever. Because we have never seen, in modern history, in American history, we have never seen a president enrich himself or his inner circle like we're currently seeing. So, so the universe around the president, you know, and all the business dealings, all of that, right? Our federal government has now invested in over 30 companies, right? $277 billion. And whether it's the president and his family, cabinet members and their family, or the universe that they're around, wealthy people are, right now, are wealthier than we have ever imagined. So if you are one of these Republican lawmakers who are leaving office, even if Trump campaigned

• 26:27Speaker 01

  against you, even if you're on the outside, you're now saying, I don't necessarily wanna get too far on the outside, because if you can't beat 'em, join 'em. At the very least, I want to make some money. And right now, there's more money to be made, and it's more unapologetic and blatant more than ever.

• 26:46Ryan Holiday?

  Yeah, and this is the, the timeless, sort of perennial human thing. Even if you were satisfied yesterday, if you suddenly see what other people are getting, it makes it hard for you to go, hey, I've got a nice house in the nicest part of town, I've got former senator, former congressman, former CEO, whatever, former general, you know, retired general, whatever the title is, I've got all of it. That was the dream since I was a little boy or a little girl, but now I hear so-and-so's flying private, or now I hear so-and-so is doing X, Y, or Z. You go, oh, actually, this was never enough, now I need that.

• 27:23Speaker 01

  Ryan, take that to the investment community. Take that to the CEO community who has always, you know, they have been increasingly, you know, public speakers, talking about the state of the world, or the economy, or labor, all these different issues. But now, we are now in a situation where just yesterday Treasury Secretary Scott Besen said, "The key to growth is going to be less regulation on corporate America," right? Like, that is, I mean, that is like, the sweet nectar of the gods for CEOs who say, "Hold on a second, I'm not going to face regulation." And, and those who always said, "Wait a minute, having three separate but equal branches of government, making sure we had an independent Federal Reserve, were part of the framework of American

• 28:08Speaker 01

  exceptionalism, they're one of the main reasons foreign investors from around the world invest their money here, and suddenly, all of that is out of whack. And when I talk to my sources on the street, and I lay it out, and I ask them about it, they're all kind of sheepish and quiet right now, because they're in the, if you can't beat them, join them. Look at the stock market performance, right? It has been extraordinary. And it's amazing, because I wonder, like, well, what, just today, okay, nine months ago, the CEO of Exxon, after we originally detained and arrested Maduro, the CEO of Exxon said, "Yeah, yeah, yeah, but we're not going back into Venezuela. It's uninvestable. We've tried to do it over the last 50 years. We've all gotten burned."

• 28:52Speaker 01

  Fast forward to today, right, the president basically announces, three days ago, that we're going to have a state-owned oil company with what we're doing with Venezuela. And all the big oil executives were invited to the White House today, except the Exxon CEO.

• 29:07Ryan Holiday?

  Right.

• 29:07Speaker 01

  So you've got to wonder, that person stood up, told the truth about their business, or the way of the world. And I wonder, are they happy they did that? Or today, is their board saying, "You should have kept your fat mouth shut. You shouldn't have told the truth about an industry that you lead, because now, maybe we've left money on the table." That's the situation that we're in right now. And I think we haven't begun to realize what the consequences of that will be. But we live in a universe of short-termism, and we're, you know, we're high on our own supply. How can, with all of this money on the table, people can't resist.

• 29:44Ryan Holiday?

  Yeah, and, and those CEOs probably agree, but they tell themselves, "Hey, my obligation is not to the truth. My obligation is not to my country. My obligation is not to right and wrong. My obligation is to shareholder value." That the, the way we can rationalize doing what we know isn't right, is, uh, well, it's, it's an incredibly powerful thing.

• 30:09Speaker 01

  Those are the same CEOs that know it's not right, that for the last year and a half, have crawled to the White House, hat in hand, they've either, they may have paid a lobby, a newly-formed lobbyist that's close to Howard Lutnick to get a meeting with Howard Lutnick, and then get a meeting with the president, and say, "Dear Mr. President, what can you do to give my company an exemption from these tariffs?" Knowing that none of this is the way business is supposed to operate, which is the reason the president loves the tariffs, because it is one place where he can truly hold a wand and be a kingmaker. But they rationalize it by saying, "Listen, my obligation is to make sure my employees have jobs. My obligation is to make sure my customers are buying my products. And my obligation is to my

• 30:53Speaker 01

  shareholders. And if I do those three things, then I'm fulfilling my fiduciary responsibility, and I'm getting my job done. And then when I go home from my job, I have to take all my clothes off before I get out of the garage, and take two showers, because I know how gross this is."

• 31:08Ryan Holiday?

  Yes. The irony is, and this is like, why it's, it tends to be a bad bargain over time, is you think, "Hey, this is what I'm doing to get access, to protect my business," right? This is the same reason people pay protection money to the rackets, or to mobsters, is, is you think it's buying you security, but what it's actually doing is compromising you, and now that person owns you, right? So, you, you think it's, it's like this short-term hack to success, but actually, it creates this kind of long-term dependence, either specifically on the person you've compromised yourself to, or because you just, you know, took a whack to the, the security of the system itself. And, and so it's this collective action problem, where we've

• 31:51Ryan Holiday?

  all taken for granted, the rule of law, general honesty, you know, a, a system that doesn't play favorites. And, and I'm not sure that survives this.

• 32:04Speaker 01

  I 100% agree, but I think the people who we're talking about are either so scared and panicked, that they're going to lose their business, or lose their position. They're like, "I've got to do it." Or they're so arrogant, they believe they're the ones, they believe they're the only one in the history of Trump's universe, that are not going to get screwed. Look at the murderers row, that, that take position, take vision, and then he turns on them, and they're like, "I can't believe this happened." And it's like, "You thought you were going to be the one woman to change that guy who was a jerk? Uh-uh, honey. He's always going to be a jerk."

• 32:37Ryan Holiday?

  Yes, yes, yes. It's fascinating, you know, I was just reading this interview with Daniel Ellsberg, for this book that I'm writing. And, and one of the, the interviewer points out, like, that, that hundreds, if not thousands of people knew, at some level, one of the lies about Vietnam, right? He's not the only one, for instance, that knows the Pentagon Papers. He's not the only one that knows about what happens in the Gulf of Tonkin. He's, he's not the only one that knows about the covert raids. Like, lots of people that knew, different things. But he's basically the only one that says, "Hey, actually, my duty is not to the president, or even to, like, my employer. My duty is to the truth generally," right? And-

• 33:20Speaker 01

  The only one.

• 33:22Ryan Holiday?

  The basically the only one. I mean, McNamara, there's this famous quote from McNamara, who, there's, there's actually a quote in the Pentagon Papers, where it says, like, it talks about this meeting where, you know, McNamara is saying, "He thinks this thing will work." And then the damning line in the Pentagon Papers is, "McNamara would never be so optimistic about the war again, except in public." So he knows privately that it's, it's, it's over, but he continues to make these public statements. And, and there's this McNamara thing, where McNamara goes, like, "This idea that, that you have a higher duty is, is rubbish." He says, "Your duty is to the president, not to the truth generally." So, so my point is, we make all these excuses, right? We make all these

• 34:06Ryan Holiday?

  rationalizations, and we expect somebody else ultimately to stand up, or speak out, or we hope other people are living honestly-

• 34:14Speaker 01

  Here's where I take issue with that, right? If you want to go truly live a private life, right, and, and, and, and get no credit, and not be on a public stage, then you're, you're more than welcome to mind your business.

• 34:28Ryan Holiday?

  Yeah.

• 34:29Speaker 01

  But if you chose to be in public office, if you chose to be a public facing CEO, it kills me that, like, what they say in private, I, I mean, I remember in Trump's first term, when, when anonymous sources used to call us all the time, right? This would be specifically around Ivanka Trump, when, when Trump was doing, I don't know, like, when we were maybe at the height of Stormy Daniels. I don't remember what it was, but I would get all of these calls from sort of anonymous sources, from sort of like Ivanka allies, that would say, like, "I just want you to know, that behind closed doors, they, she really thinks this, or they really do that, or the support she gives to the LGBT community, or the environment."

• 35:12Speaker 01

  And to that, I just say, "No, if you're choosing a public-facing role, where you want public credit and public accolades, I don't think you get to have, right, private views that oppose what you're saying and doing publicly, as it impacts policy, politics, businesses across this country." To that, I say, "No, I, I don't think you deserve that, Grace."

• 35:38Ryan Holiday?

  Yeah, it's like, "You're so powerful, except you can't say what you think." What, what kind of power is that, you know? If you don't have the job, the job has you, is ultimately what it comes down to.

• 35:49Speaker 01

  Yes. Listen, it's one of the reasons, you could love Bernie Sanders, or hate Bernie Sanders. But Bernie Sanders has never deviated, right, from, listen, it's probably one of the reasons, if you actually look legislatively, and I don't say this in a mean way, Bernie Sanders hasn't gotten a lot done. And I'm not saying it in a bad way. And it's because he stays absolutely true to his values and his ethos, and what, what he wants to do. Now, an outsider could say, "Well, because he doesn't play ball, or because he doesn't compromise, he hasn't gotten much done." But at the same time, he could say, "This is who I am. This is what I believe, and this is what I represent." And that level of authenticity is what has made him

• 36:33Speaker 01

  continue to be a super, super, superstar well into his 70s.

• 36:38Ryan Holiday?

  Yeah, it's like, look, in some moments of time, you need, you need people who can play ball. You need people who are a little bit more pragmatic, maybe people who can say one thing in public and do another in private. But in times of corruption or dishonesty, or in moments like now, chance, almost certainly, we need you to play less ball and be more principled, right? Like, we need-

• 37:01Speaker 01

  There should be a baseline, right? And that baseline in the current, right now, in this moment in time, has been completely blurred. Like, I get in life, in business or in politics, you should play ball, right? You shouldn't completely abandon your values, but you should play ball because compromise is the answer, right? It's how we solve things in our private lives and our public. But, but right now, we're watching Congress, at least Republicans in Congress, completely just walk away from even, even their, their basic job functions. Because the president is saying, if you don't side with me, you know, I have a $400 million war chest of campaign dollars that can go to one of you, so you, boys and girls, better behave.

• 37:44Speaker 01

  And it's becoming increasingly difficult for all of these Republicans to side with him because he's presiding over a war that makes no sense that we're boxed into, an economy that's problematic for millions of Americans, healthcare that millions of people are losing and even more are going to lose after the midterms. It's actually why Mike Johnson wants to recess sooner than they're supposed to because they don't want to debate on the floor and have to talk about these policies because they're so wildly unpopular. Just today, the president, I'm blown away, put a post on social media that basically said, anybody who doesn't want to have an AI center where they live just wants to live somewhere junky and be poor.

• 38:27Speaker 01

  And I'm paraphrasing it, but that was the, the spirit of what he said. And I'm like, how is he going to help Republicans win? It's something like 71% of Americans are saying, I don't want a data center in my backyard. In your state, Greg Abbott, right? Like, he's dealing with this, more people are saying, I don't want this. So how's he gonna thread the needle, trying to answer to constituents who have no political affiliations, but they're saying, I don't want this here? And a president who is very, very clearly sided with the, the tech oligarchs, one could say, and largely unregulating an industry that's going to impact every element of our lives, while you're having massive growing dissent among the American voters?

• 39:14Ryan Holiday?

  Well, and that goes to the compromise we're talking about, which is you tell yourself, hey, I'm aligning myself with this person. I'm not challenging this person because he's popular, because it's good for my political prospects. But those tend to be a bad bargain in the long run, right? Because you're actually, there's a reason we have an adversarial system, right? There's a reason that each branch is supposed to jealously guard its prerogatives. It's, it's good for the politicians too, right? Like, you're throwing it out of balance by not doing your job. And, and then ultimately, it screws you up.

• 39:47Speaker 01

  But don't you think checks and balances are what make us better and smarter and more successful, right? When you actually have to, to, to, to make your pitch, right? When you have to make your pitch to voters, when you have to make your pitch to the rest of your caucus, when you have to convince people on the other side of the aisle, you learn to make a better argument. You learn to create better policy that serves more people. If you can just steamroll the universe and get what you want, that's when you really risk hurting more people.

• 40:19Ryan Holiday?

  Well, look, to go to, to politics and power specifically, you would think that in the midst of the most difficult moment in American history, the Civil War, you'd think that the president would want a cabinet totally on board and behind him 100%, right? Except, no, that's the opposite. Lincoln picks a cabinet of rivals, and, and they have these knockdown, dragout debates. They're plotting against each other. But, but what he actually understands is that the cabinet is representative of the country, all the different threads of the body politic, right? And the different interests. And so he wants their opinions in those meetings. He wants to have to convince them and figure out the compromises that they can all live with,

• 41:03Ryan Holiday?

  that, that actually this, this sort of lack of unity is what allows him to unify the country because it's a proxy for the larger problem that he's trying to solve. And so, yeah, like, again-

• 41:14Speaker 01

  But Ryan, what you're leaving out is that Abraham Lincoln chose a really hard job.

• 41:22Ryan Holiday?

  Yes.

• 41:22Speaker 01

  Okay? He chose to make it hard. Fast forward, you're the CEO of a publicly traded company, right? You know that you're not just answering to shareholders, you're answering to your board, your highly critical, difficult board that you need to win over and sell. And then you look to the left and you say, wait a minute. What did Elon Musk do? He padded his board. He has super voting shares of everything, and he has absolute ultimate control and has a huge amount of influence over our government.

• 41:56Ryan Holiday?

  Yeah.

• 41:57Speaker 01

  And, and you're one of those other CEOs, obviously a much smaller one, and you're like, damn, I've made this too hard for myself. I don't want to get shot in the theater, Mrs. Lincoln. I want to go the Elon Musk route.

• 42:09Ryan Holiday?

  But the funny thing is, like, what they're missing, right? Is, yes, it's, the hard is a feature. And yes, Elon Musk is incredibly wealthy and has been incredibly successful. Also, though, that system has been profoundly bad for him by any other measure, right? It's broken his brain. It's responsible, I, I won't dance around this, for the deaths of potentially millions of people, right? Like, the, the richest man in the world stole medicine and money from the poorest people in the world. And the, the consequences for that will play out over the next several years, and they will be heinous and vile. And it hasn't been, it hasn't been good for him. I would argue that Elon Musk would have been better served. By the way, he had an unlimited amount of money before. He has unlimited money now.

• 42:53Ryan Holiday?

  It hasn't actually improved his life in any way. I think Elon Musk would be closer to accomplishing the things he wants to accomplish if he was served as a board is supposed to serve him and as, if checks and regulation and, and, you know, the way the financial markets are, are supposed to be there, I think that would all be better, you know? And like, we, we only have to look at history, for an example. Like, I'm sure nobody felt super empowered to tell Napoleon that invading Russia was a bad idea, you know? Hitler got rid of the people that told him invading Russia would be a bad idea. Vladimir Putin got rid of the people. If, if Ukraine is supposedly part of Russia, then invading Russia in winter is a bad idea, right?

• 43:37Ryan Holiday?

  Like, these checks and balances can be onerous and obnoxious and unpleasant, but they save you from destroying yourself. They're not supposed to be fun day to day, and they may cost you something in the short term, but ultimately, they're there to prevent catastrophic failure. I think this goes back to Vietnam, which we were just talking about.

• 43:57Speaker 01

  As long as we have a free press, and despite efforts to repress it, we do, I do not believe the history books will lie. Earlier this year, I don't know, maybe we were five weeks into the war with Iran, I was at a conference in LA with, without a doubt, the biggest investors, at least the biggest US investors, but probably the biggest investors on the planet. And I got back on the plane just, just almost despondent, right? They talked about our extraordinary military might, what we did in Venezuela. And then they talked about what we were about to do in Cuba. And they all basically leapfrogged right over Iran

• 44:41Speaker 01

  like it hadn't happened, like it was this quick blip. Oh, it just happened, I mean, that's over. You know, I just talked to Howard Lutnick. He said, we're finished. I talked to Scott Bess, and he said, we've moved on. Trump's not interested in it anymore. And two days ago, yesterday, we marked six months in this war in Iran. We are now boxed in. We are spending, we now hit 40 trillion in terms of our deficit, okay? We're spending billions of dollars. We've lost 18 American lives. The Strait of Hormuz is closed. It's impacted gas prices, fertilizer prices, food prices. And I sat there, leaving this conference with the smartest minds in finance, with everybody being like, Iran? What, Ron? And I'm going, the history bu-

• 45:25Speaker 01

  and I'm like, gosh, is this what German industrialists were- is this how they talked when they were at cocktail parties and conferences a few decades ago? And I wonder, is that what we are going to say? And I, I do- Have faith in the history books, just like I have faith in journalism, that the president has absolutely put the fear of God in a lot of people, and there has been a chilling effect. But Ryan, just look at the way this war is being accurately covered every day. The fact that we are seeing people at the Pentagon, people in the military, talking to the media, that's not usually the leaky branch of government. Remember when Pete Hegseth kicked the Pentagon press corps right out?

• 46:10Speaker 01

  They basically had to sign a piece of paper that said, "The only thing we are going to report is the press release that you hand us every day, and then we're going to walk to a microphone and read it." And when the press corps said, "We are not going to do that", they didn't stop fighting, they didn't stop telling the truth. And I think something that's really important is understanding that the truth is not biased. Lots of people just don't want to hear the truth, because oftentimes, the truth doesn't tell a story that people want to hear. And I think that's a really important thing, that we need to keep communicating, understanding, and holding ourselves back from getting in petty fights,

• 46:53Speaker 01

  or insults, or mocking people, or allowing people to say, "You're just biased." I think we have to press pause and say, "Hold on." Every time someone says this, they say, "What does biased mean?"

• 47:05Ryan Holiday?

  Right.

• 47:06Speaker 01

  Okay? Because you could say, "You're biased in that you want America to survive. You want the country, you want our kids to be better and stronger than we are." And the truth isn't biased? It's just something that a lot of people don't want to hear.

• 47:19Ryan Holiday?

  Yeah, and look, speaking of Vietnam, like, the reason that the press corps is-

• 47:24Speaker 01

  Speaking of Vietnam.

• 47:25Ryan Holiday?

  No, is so adversarial to the government in war, is we realize, because they did give the government such a bit of latitude, and they assumed it was acting in good faith, or worse, that they assumed it was competent, right? And we walked into this horrendous war, that we, that by the way, we desperately wanted to get out of, but couldn't, right? Which should sound familiar, like, it's not just that we start things in error. Some errors are very hard to extract yourself from. And so the reason that the press is supposed to be hostile, and by the way, the people should be suspicious and somewhat cynical, and there's supposed to be a preponderance of evidence,

• 48:09Ryan Holiday?

  and then, by the way, military action has to have consent of Congress, the representatives of the people, is to prevent us from making that error again. And we're in the middle of doing it. You could say, "We've already done it", and it's going to be a generation or so to undo it. But yeah, like, you think that you want people to tell you what you want to hear, and you think you want them to back you up, but actually, what they're going to do is save you from yourself if you allow, if you say that their higher obligation is to the truth, to the country, you know, to peace, to principle, whatever it is. You don't want them pledged to you personally.

• 48:52Ryan Holiday?

  You want them pledged to the principle.

• 48:55Speaker 01

  But Ryan, we more than just started this war in error. We started it dishonestly, and we've yet to explain to the American people or the men and women that are serving our country. Our administration has yet to honestly explain why we did this, right? If you remember, right after we launched these attacks on Iran, the president in the beginning wasn't doing many sort of sit-down, long-form interviews, but what he was doing was taking phone calls, right? I spoke to the president, lots and lots and lots of people would call the president on his cellphone, and he would talk. And that was his way to just sort of shoot information out of a cannon that wasn't true.

• 49:40Speaker 01

  And he was basically on message, saying the same thing over and over. We had no choice. Two, I remember it, "Two weeks from now, Iran was going to have a nuclear weapon, it was going to be complete, and they were going to use it," right? And when you would say, "Mr. President, you said that a year ago, you wiped out their nuclear efforts, and how could that possibly be?" But he wasn't going to pause, he was just gonna- and there was no evidence backing up that they had nuclear power. But he was just gonna flood the zone, flood the zone, flood the zone. The problem is, less and less people are believing it, and you have to go back to his original promises, right? When you brought up Elon Musk, Elon Musk potentially holding back money and holding back medicine that cost thousands and thousands of lives,

• 50:22Speaker 01

  the reason they put Doge in place, right? Was because we needed to have checks and balance, we needed to clean things up. Well, it turns out, the opposite has happened. And now we've entered a situation where we're spending billions and billions of dollars. And think about all of those Trump voters, who, when we got rid of USAID, right? I can remember even talking to my own mom, and she was like, "Stephanie, I know this is bad, and I know, but you know what? There's kids in West Virginia that are suffering, and I've got to care about the kids in West Virginia before I care about the kids in West Africa." Well, how do you think those voters feel right now? Who say, "We didn't care about the kids in West Africa, and now we're not caring about the kids in West Virginia",

• 51:05Speaker 01

  where they can't, where their families can't afford to put three meals a day, and they can't afford to put gas in the car? So even the political argument that the president was making, there's not a continued through line.

• 51:17Ryan Holiday?

  Well, it's also just stupid. I mean, we were buying corn from Iowa and giving it to people in, you know, this country or that country, so it actually was taking care of both.

• 51:26Speaker 01

  Yes. We now have a Farm Aid bill on the table because of all those farmers who have not been able to sell their crops to USAID, to other organizations, so we can send that food abroad.

• 51:37Ryan Holiday?

  It's madness. But I do think, you know, you can see that the problems of big, powerful electric leaders or heads of state, how their information, the quality of their information diet degrades, even though they have access to the best intelligence, they're not getting the truth from the people around them. Like Biden's obviously an example of this, Trump's an example of this. But I'd be curious, because we started this talking about sort of tech people and Wall Street people, do you find that just the more powerful, successful, rich someone gets, the more they live in a bubble? I think there's an argument that part of the radicalization of tech specifically is rooted in that them deciding that the media was hostile to them,

• 52:21Ryan Holiday?

  and deciding to kind of create their own media bubble. So they all talk to each other on group chats, they all read the same blogs and listen to the same weird podcasts, and they spend ironically way too much time on social media. Like, you talk to them, and you hear them say things, and you're just like, "Are people around you afraid to say that you sound like a moron, or that you sound like a villain when you say that?" I just found that there's something about the bubble of those people as they become more and more powerful, that has warped who they are and what they stand for.

• 52:57Speaker 01

  Yes, I would say two things. That's why they said, "We have to wipe out the media that exists and create our own." Because of all the things that they could control, they could not control the power of the pen, right? And they couldn't control a person who made one thirtieth of what they made, right? Who they consider, you know, it's funny, like, think back to COVID, for example. You know, my kids go to fancy private schools in New York City, and we have seen an insane amount of principals from public schools, but headmasters from private schools retire, walk out of the job since COVID. Why? Because titans of industry during COVID, because I'm a guy who made a ton of money on Wall Street,

• 53:42Speaker 01

  I'm going to tell you how you should run this school. I'm going to tell you what your COVID approach should be. Because I made all this money, I know best. And that same mindset has been the mindset to say, "I'm now going to create and control a media sphere that I like." Now, that being said, are there bad journalists out there? Sure. Do people make mistakes? Sure. Are there people that are highly motivated? Absolutely, nobody's perfect, but tons of people, especially in the business universe, felt like they were so threatened by that power of the pen, so they had to do everything they could to wipe it out. But I would say, among the people that I sort of admire the most

• 54:26Speaker 01

  are always the most well-read, right? Like, look at David Rubenstein from Carlyle.

• 54:31Ryan Holiday?

  Yeah.

• 54:31Speaker 01

  I remember years ago, David Rubenstein talking about a huge risk was people who were illiterate. Not illiterate, people who chose not to read, who chose not to advance themselves. And when I think about people who are the most thoughtful, or who are the most impressive, they're people who read the most. And I don't just mean read their own tweets. I mean, people who are saying, "I want to get better and smarter."

• 54:59Ryan Holiday?

  Yeah, it's like, there's something about these people, they went from reading these big biographies, and history, and psychology, and now they just read, you know, like, the latest thing from the Free Press, or these like, same seven Substacks. And it's not to say that there's anything wrong with that, but they're just missing the way that, as they have become more powerful and important, there's become a whole media industry around giving them the information that those people want, confirming that worldview. And they all, it's, they all think they're contrarian, independent thinkers, and then they're reading like, the same five sources, and then quoting it back to each other. And because of the halo effect of how powerful and important they are,

• 55:43Ryan Holiday?

  a lot of other people who want stuff from them are saying, like, "You're a genius."

• 55:48Speaker 01

  Correct, but yes, and they've become more powerful and more successful. But I would argue, the people's approval, who they seek the most, they're not only still not getting, they're infuriating. Like, it's funny, you know, when I talk to people, and you know, they talk about Mum Donnie, like, he is this boogeyman who's coming for them and wants to destroy their universe. And they talk sort of about, you know, DSA. And I'm kind of like, "Guys, it's not Mum Donnie who created this. It's basically the fact that you've taken such a big piece of the pie, right? That you're gorging yourselves on the pie,

• 56:31Speaker 01

  that the rest of the universe is saying, you know what? Power isn't necessarily, or isn't only, the power of money." And we're actually seeing this shift. And I think it's the biggest shift we've seen in our lifetime, just this like, uh-uh. People saying, "No, it's power to the people, and I don't want to see this be the case." And listen, you can look right now at political fundraising, right? There is more money in politics, right? Just in these midterms, it was just reported today. There's a billion dollars of dark money, right? And it could, just extraordinary. But we're actually starting to see diminishing returns in that dark money as more and more people, despite Citizens United, despite a recent decision by the Supreme Court to say,

• 57:16Speaker 01

  let's just put more corporate dollars into politics. More and more Americans are saying, this doesn't work for me. And I find it interesting to watch people start to say, no, I'm more energized than ever to vote against this structure. And so it's funny, it's like, I don't think it's democratic socialists that are coming for capitalism. I think it's many of those who sit on top of capitalist mountain. They're the ones who are destroying it and they don't necessarily realize it.

• 57:46Ryan Holiday?

  Yeah, it's like that Simpsons meme where Superintendent Chalmers is like, could I be wrong? No, no, it's the children who are wrong, right?

• 57:53Speaker 01

  Yes, yes.

• 57:54Ryan Holiday?

  You just can't conceive that maybe you used to create things that were incredibly popular with people. And now everything you do and say is incredibly unpopular. What could have shifted? And it's like, no, no, no, I'm the same. Everyone else has changed. It's like-

• 58:11Speaker 01

  But Ryan, like, I say this as somebody who deeply believes in free markets, who deeply supports, you know, good capitalism, all of it. And I'm like, guys, I, I'm into capitalism. What you're currently practicing, which is like the ultimate in crony capitalism, that's what's taking it, like, that's what's causing the unrest, right?

• 58:33Ryan Holiday?

  Really?

• 58:33Speaker 01

  Not somebody, not someone you've never heard of from an outer borough who said, by the way, defund the police. And I'm convinced that defund the police was started, that even that slogan was started by the far right. And I'm like, no, no, no, no, no. It's coming from inside the house, guys.

• 58:47Ryan Holiday?

  Sure. No, and look, and we've seen moments like this before. You know, this is the progressive era coming out of the, out of the Gilded Age. And then this was, was, was the, the way that FDR rides into office because-

• 58:59Speaker 01

  But Ryan, don't you think that the Gilded Age we're experiencing right now? When people don't have empathy, when they don't see, when they don't understand how people live. Doris Kearns Goodwin, I remember interviewing her soon after Trump's first term. And I remember she had interviewed or she, she had written about sort of every living president and her concern for Donald Trump is one thing. She didn't see him exhibit was empathy. And she said, everyone else, maybe not when they were campaigning, but after they won, they traveled the country, right? They went to small towns, they went to big cities, and they truly understood the plight of the American people. And that's when they sort of said, how am I going to serve this country? And she said, I don't see that in him.

• 59:44Speaker 01

  Look at how we're living right now. And I said this earlier, wealthy Americans are wealthier than we have ever seen. They currently don't go to the same schools as anybody else. They don't go to the same airports. They don't go to the same hospitals. I recently had someone help me with someone sick in my family with a hospital. And I wrote them a letter after and I said, hey, thank you for getting me help with that doctor. Really helped my, help us so much. And they wrote back, that's, that's great to know. I've never been there. And I said, you sit on the board of this hospital? And they said, oh, I, we use private concierge medicine. And I remember just like, just saying, holy cow, right? You've got highways that if you don't like the lane you're in on this highway, well, you can pay an extra toll, you can pay an extra toll that you can speed ahead.

• 1:00:27Speaker 01

  So now we're in a situation where this sliver of people aren't even experiencing what, what the majority of the Americans are. And in fact, they have disdain for it. And this is where I see this real crack in the system.

• 1:00:42Ryan Holiday?

  Yeah, you cease to live in reality. And this is, it's like TSA was a, a check and balance. You didn't understand it, but it's like flying-

• 1:00:49Speaker 01

  The DMV.

• 1:00:50Ryan Holiday?

  Yeah, flying at the airport like a regular person was part of the, the thing that kept you normal. Having to do some of the things that other people do kept us all on the same planet. And, and so, yeah, you think by, by getting everything you want that you are, you know, going to be better served. But in fact, you're losing some, some really important things than you need. And so if you can have power and success and influence and not lose your mind, it's a really, that's a really rare thing to do. And it, I think it's worth pointing out that we don't hate all the same people the same way. Like, like, um, my son just had to go to the hospital a couple of months ago. And, and so we spent three nights in, in Dell Children's Hospital,

• 1:01:34Ryan Holiday?

  which was a, a not fun experience. But I did send Michael Dell a text after. I'm like, you should be incredibly proud of what you've done. And I think it's worth pointing out that there are, there are some billionaires who are using their power and influence to do things that people don't hate. But you have to stay rooted in reality. And to go to your point about empathy, to know what people want and need.

• 1:01:57Speaker 01

  I mean, Ryan, look at New York City, right? Like, New York is experiencing this, like, the wealthiest New Yorkers would say, like, they're coming for us or there's this big divide here. And I would argue, one of the reasons New York is the best, I think, one of the best cities in the world is because of arts and culture. And our arts and culture thrive because of philanthropy. And so I don't believe the answer is wealthy, bad, wealthy, good. The answer is, how do we understand one another? How do we collectively say, right? Trump wants to say, the government should run like a business. And I understand when people originally have that sentiment. But if you look back through the arc of history, right? When the Dow was first created, none of those companies still exist, right?

• 1:02:41Speaker 01

  Our country has existed for 250 years. We should not operate like a business, right? What our government should do is create a framework to ensure that people are physically safe, socially free, you know, have the, the framework that they can be financially secure. That is different from running a business. Now, should we operate in an efficient way? Should there be checks and balances? Absolutely, and we have those things. But the behemoth of a federal government is not going to move fast and break things, and break things. Sorry, Mark Zuckerberg, that's going to cost lives.

• 1:03:16Ryan Holiday?

  Yeah, no, no, you're totally right. It's like, look, the, the, actually, the purpose of government is to solve collective action problems, right? And, and you could argue that the, the point of business is to exploit collective action problems, right? So there's a, there, it's not that they're mortal enemies of each other, but, but the, the, the government gets tasked with the difficult, unpleasant, difficult to resolve, you know, sort of perennial problems of human society. So by nature, it's going to be unwieldy and inefficient. It's going to be a little lowercase c conservative. It's going to be bureaucratic. These are all features and not bugs of the system.

• 1:03:55Speaker 01

  Okay, Ryan, the, the private business, right? FedEx and UPS could say, I don't want to go to rural America. I'm not going to get a return on my investment. You know, every house is four miles away and they don't even get packages. FedEx and UPS can say, I'm not going to serve that community.

• 1:04:12Ryan Holiday?

  Right.

• 1:04:12Speaker 01

  But the US Postal Service can't, right? Those are two different things. So a public school has to say, if your child is five years old and vaccinated and you live in this school district, our doors are open and regardless of your kid's needs, we will educate that child, right? That is going to mean, it is going to be difficult, expensive, less efficient, slower, possibly less performing than a streamlined, supercharged, top-notch private school that can say, oh, we're going to knock out the whole bottom third because they don't fit our profile. So those are two different things that can coexist in the world, but they shouldn't necessarily, but they shouldn't be the same. They serve a different purpose.

• 1:04:56Ryan Holiday?

  Well, I, I will say, and then I'm, I want to let you go because I want to be respectful of your time. But speaking of money, to go back to where we started, you gave me some wonderful advice about three years ago.

• 1:05:05Speaker 01

  When we met.

• 1:05:06Ryan Holiday?

  Yes, I was looking at a school for my kids. They have some, some, some learning layers. This was one specifically designed for them. And, and I was telling you, you know, it's quite expensive. And, and you said, um, yeah, but that's exactly what money is for. If not for that, what is it for? And that made it a, a, a very easy decision. Actually, you said, do you want to sit in traffic during the morning and the evening and hate it? Or do you want your kid to sit in a school all day that they hate? And, and both those things were incredibly important and, and eye opening to me. And it ultimately brings us, I think, back to this idea of like, money is not bad. It's just what do you use it for?

• 1:05:48Speaker 01

  Money is a tool.

• 1:05:49Ryan Holiday?

  Yes.

• 1:05:50Speaker 01

  And, you know, it, it can be a hammer that you beat yourself with, or it can be one that you use. And I know that I worked really hard in my life and I continue to. And I'm super blessed to have worked in two industries that do pay really well. And I have had the ability to say, what are the best schools that'll serve my kids the most? Because again, it doesn't buy you happiness, but I would argue it buys you that freedom to say, fine, I'll sit in two hours of traffic. Because the thought of that kid hating school for eight hours a day is when we lose those kids. And I'm so glad you were able to get the best education for your kid. And my hope and a lot of work that I do is try to figure out, how do we get this for more kids in this country?

• 1:06:34Speaker 01

  Because everybody deserves it.

• 1:06:36Ryan Holiday?

  Yeah, and I was thinking about it the other day. It's sort of, what is your definition of rich? Like, obviously, being able to afford the tuition is, is, is a nice, you know, sort of perk. But I also go like, you know, rich is having the freedom to pick them up from school when I want or to, you know, to, to be able to do drop off when I want. Or when my son was, was, was sick, like, it was one, not having to worry about, you know, do I have health insurance or not? But also to be like, hey, you're not going to hear from me for the next three days while I go deal with this.

• 1:07:03Speaker 01

  Ryan, rich is your kids not coming home from school devastated.

• 1:07:09Ryan Holiday?

  Yeah.

• 1:07:09Speaker 01

  Or losing all their confidence.

• 1:07:11Ryan Holiday?

  Yeah.

• 1:07:12Speaker 01

  And their self-worth. Rich is to be able to leave work at five o'clock so you can sit across from your kid at dinner and understand what they're going through. Because I would argue, true wealth is watching your kids thrive. And, um, having the means to help them when they need it is, for me, worth everything.

• 1:07:33Ryan Holiday?

  Ah, that's the perfect place to stop. Thank you so much. This was amazing. Can't wait to see you again.

• 1:07:38Speaker 01

  Thank you for having me.