The Exchanges, every show

Q and I see things that maybe other people don't see, and I just notice things, and I am able to talk about them, and it makes everyone laugh because it's something that they all notice, but they're not exactly sure that they're sensitive enough to really, uh, comment on it. What allows you, do you think, to come up with these interesting observations? Is it being sensitive? What is it?

A It's mostly IP theft. I get most of my ideas from other people, and I'll pause when I see something really interesting or that kind of moves me. And I'll repeat it a bunch of times and try and apply it such that I remember it. I, I've just found this thing, I forget who even said it, but it really moved me, and it was that, ah, everything does not demand your judgment. You don't have, you are entitled to not have opinions on things. And it, I just paused and I thought about it over and over and over, and I've used that, I've used that line a bunch of times because I was falling into this trap of Dunning-Kruger. I thought, okay, because I have some insight around a couple of things that everyone demands to deserve and wants my opinion on everything. And I w I do all these hot takes on the podcast and videos and, you know, it's like the Epstein files come out and I'm like, all right, how do I wrap my hands around that? And I'm like, you know what? Maybe the world isn't dying to hear from me about the Epstein files. Uh, maybe the world isn't dying to hear about my views on Iran, although I have a lot of views on Iran. It's like, okay, it's okay to occasionally sit back and just shut the up. Anyways, my point is, if I see something that I find really insightful and interesting, I stop, I read it a bunch of times, I try and apply it, and I try to cement it into my gray manner. So I …

AI assessment note: “It's mostly IP theft. I get most of my ideas from other people”

Q So you're picking companies that have kissed the ring, is what you're talking about?

A These are the enablers. These are the people who've said, okay, kiss his ass. I mean, there's some historical precedents here. In the early thirties, Germany, the captains of the manufacturing industry turned a blind eye to Hitler and the rise of fascism because he said, if you don't come out against me, they were very worried about him. I will crush the trade unions and you will make a shit ton of money. There's an apt analogy here. And that is I get text messages from these guys saying, I hate myself. I don't want to go to the white house. I'm like, well, I hate you too. Cause you're not willing to speak up. And the very values and principles, rule of law, capitalism, competition, free markets that built these amazing companies and made these guys billionaires is under attack right now. And they don't want to speak up because they think they're going to make money. We'll be careful what you ask for, but these are the enablers and your free gift with purchase, spend less money, send a message to the people who, you know, tell them to put away the knee pads and speak your mind. They probably have to do it collectively because he goes after people who go first, but this is a, Great way to send a message to the president, to the markets, and to these individuals that this, what, what is happening here is un-American, and you are desecrating the values that made you so goddamn ric…

AI assessment note: “These are the enablers. These are the people who've said, okay, kiss his ass.”

Q But, but in, like, free market economies, where we see situations like that, do you believe in active government intervention?

A Yeah, but it's a balance, right? I don't, I think one of the strengths of America is we have a tendency to have more of a wild west attitude, and I think that is probably, to err on the side of too little regulation is probably better than too much regulation. That could loosely be defined, or if you were to try and come up with three or four reductive reasons why the U.S. has created so much more economic value than Europe, I think if you're intellectually honest, you would say that in the U.S. companies are allowed to ask for forgiveness, not permission. And there's, there's some value to that. There's also a downside, and that is, we have a 60% uptick in teen suicide in the US, and I don't put it all at the hands of social or the feet of social media, but it's definitely played a role, and Europe is more thoughtful about You know, what privacy regulations are, right? And I do think there is, uh, economic advantage to erring on the, a lighter touch of regulation, but it also comes with some externalities. But again, that's why we have a government and thoughtful people who can hopefully balance economic growth and innovation and risk and being aggressive and breaking some shit with also recognizing that, okay, Mark Zuckerberg and Sheryl Sandberg are lying to this, to us, that probably it doesn't make sense for a twelve-year-old to be spending 14 hours, you know, a day, uh, in…

AI assessment note: “Yeah, but it's a balance, right?”

Q Why though, if you don't need more money?

A Because I, you know, it's hard to get out, it's hard, it's hard to get off the hamster wheel of identifying your self-esteem and your worth with money, and also I would love a bunch more money to give away, and you know, in a capitalist society it's really sad, but the more money you have, the more power you have, the more virtue you have, Look at, we're willing to forgive a guy who disowns his children on podcasts and is being sued by two women concurrently for sole custody of their child and cuts off food stamps to kids and benefits to veterans because he's the richest man in the world. I mean, in a capitalist society, every signal is telling you there's never enough. So I think it's sort of a natural or an understandable instinct.

AI assessment note: “it's hard to get off the hamster wheel of identifying your self-esteem”

Q I do, but I do feel that people treat me differently now than I, they used to. People don't argue with me as much. People stop talking when I talk. Uh, when it comes to kind of family decisions, my voice matters much more than anyone else's. Why? Because I'll pay for it.

A Yeah, there's, and, but even the fact that you're self-aware enough to know that, you know, I'm on constant editorial calls, and the majority of my team is 24, 25, and someone will disagree with me or say something rude, and I'm like, man, I'm gonna self-fire that motherfucker. I get angry because I have such a big ego, and then what I realize with just a few minutes of reflection is, it's really important you keep those people around you, because you can start to believe your own press, and start to believe that, and that's also one of the wonderful things about kids. Your kids are not impressed by your professional success at all. At all. As a matter of fact, they're not, they're totally unimpressed with you. Like, dad is lame. I'm literally the uncoolest person in the world in their eyes. Uh, but I definitely agree with you. Once you have money, people laugh at your jokes, people find you interesting, people want to know you, and it can lead to bad places. I have found as I got, as I've gotten older, I don't make as much of an effort with people. I went to this thing at the Tate last night, one of these fancy galas, and I'm so used to everyone wanting to know me and starting conversations with me, and I was sitting with these artists, and I thought, I need to be less arrogant. I need to be More friendly, and not expect everyone just to be, like, asking me questions and wanti…

AI assessment note: “Once you have money, people laugh at your jokes, people find you interesting”

Q How do you know when to settle with compromise versus look for perfection?

A Oh, I don't know. I, I think everyone's different, but for me it was, but for me it was willing to throw up the deck of cards that was my life and let them land anywhere because I didn't want to lose this person. I had no desire to have kids, and this person made it clear to me that, okay, if you don't want kids, I get it, but we're, I need to move on because I want to have kids, and so I was willing to reconfigure my life because the idea of not having that person in my life was really upsetting to me. So that, you know, that either happens or it doesn't. The hard part is, as you get older, you become more set in your ways. But I, I would imagine what happens to the majority of us will happen to you, and that is you'll meet someone and you'll decide that the sacrifices are worth maintaining that person in your life. I think that's general. I don't think any guy ever decides. I mean, this is terrible. I think most men who are successful Like the optionality of not being committed or married or having kids, and then I think what happens a lot is your partner's not up for that, and, and, and basically says, okay, it's decision time, and you make that decision, and then hopefully you, you look back and think that was a good idea, that was the right decision.

AI assessment note: “you'll decide that the sacrifices are worth maintaining that person in your life”

Q So you don't agree with cut out people from your life who are negative energies, who are negative forces?

A Oh, sure. You don't, don't be, I mean, I shed friends all the time. I shed relationships. You know, I used to be focused on business. You're, you're, it sounds like you're in, uh, you're in finance. It gets pretty brutal sometimes, and I've been, in my opinion, sort of, Not abused, but treated poorly by business partners, venture capitalists, and I get, I struggle with anger, and I thought, oh, I'm gonna serve this guy a cold lunch someday. And it lives rent-free in my head. And one of my mentors, Hamid Mogendam, said to me, um, he said the best, he's like, you really want to get at this guy? He was a VC, one of the most powerful VCs in the world, washed me out of my stake in my company, kicked me off the board. He's like, you really want to get back at him? I'm like, yeah, what are we gonna do? And he's like, lead a fucking amazing life. That is the best revenge. And so, if I don't, if I have a bad business partnership, something I'm proud of, I have never sued or been sued by anybody. If I have a bad relationship with someone or I feel like I've been wrong, I just don't work with them again. There are some friends in my life that slowly but surely I just do a slow fade from, I don't, I've never been tolerated an abusive relationship romantically, but generally with your important relationships, I think a healthy way to approach it is just say, I'm going to put away the scorec…

AI assessment note: “I shed friends all the time. I shed relationships.”

Q You've done an extraordinary job scaling the distribution of your, your ideas, um, your worldview. Um, uh, what, what has worked best for you on that front? And what, what can our audience take from that as they try to extend, uh, the reach and, and influence that they have?

A People consistently come up to me and say, I just think the amount of content you push out is remarkable. You must work eight hours a week. I'm fundamentally a lazy person. I work 30 to 40 hours a week. I'm really outstanding at doing nothing. Um, what I'm pretty good at. So my core competence is storytelling. My, my superpower though, attracting and retaining talented people. I have 14 people at Prop Two Media. If you want to scale your content, you got to focus on what part of this content am I really good at, and hopefully you have the resources to hire talented people to kind of build it out. That's the most obvious thing, and some people don't have those resources, I'm blessed, but if you find people who are good, you want to hold on to them, give them a vested interest and ownership in your success. From a qualitative standpoint, and then I'll talk about channels, I'm in a very blessed position, and that is, I have people who love me unconditionally, and I have economic security, which gives me license to say pretty much whatever the fuck I want.

AI assessment note: “attracting and retaining talented people. I have 14 people at Prop Two Media.”

Q error when you're talking about trillion dollar companies paying a billion dollar fine. So, you know, Lena Khan has come in with a different perspective on how to approach this and has been demonized for it. Um, although I saw this morning, even Bill Gurley was, was praising her for how she's approaching, um, some of the, the, the gaming of the pharmaceutical world. Um, what, what's, what's the answer?

A Well, I mean, ok, so on a macro level, I think you empower Lena Kahn and, and Jonathan Cantor, and we need new laws that, or not new laws, but maybe apply the Brandeisian test, where it's more on market channel power, and we need to start breaking in companies, and there's evidence that that's already happening, because quite frankly, the worms turn. Consumers see, you know, they hear stories about several houses on the block where their daughters are self-cutting, and they think, well, why is Instagram even allowed? For a fourteen-year-old girl. I mean, it's impossible to opt out. I'm, I'm fairly sophisticated with technology, and I've tried to figure out parental control. Shouldn't it be the other way around? Shouldn't it be really difficult to figure out a way for Instagram to be on my fourteen-year-old's phone? And so I think consumers are just fed up, and so the consumer support has stiffened the backbone of regulators and legislators and lawmakers, despite the fact they've had 40 hearings on child safety and social media and pass zero laws. It does feel as if we're on the precipice. The decision to break up or the decision that Google has found guilty of monopoly maintenance. I think people are getting a little bit sick of thinking that Apple is, um, totally, I don't know, in no way complicit with this when it would be pretty easy for them to age gate all of their devices…

AI assessment note: “on a macro level, I think you empower Lena Kahn and, and Jonathan Cantor”

Q Do you remember how much money, uh, when you felt that tipping point where you did feel financially secure? Not like bulletproof where nothing ever will happen, but do you remember the inflection point where you're like, okay, this feels different than I've felt on the, on the climb?

A I still don't, I still haven't hit that point. I'm still very anxious about money. You know, I had, and I like to be very open about Money, because I think that not talking about money is basically a decorum that is promoted by the incumbents and the wealthy, such that you don't understand how much money wealthy people have to keep poor and middle class people under the illusion that, oh, you, you should be paying 45% taxes while I'm paying 17. And I think, I think it's important to be very, I think it's helpful to be transparent. And I talk about how much money I've lost, um, all my investments, how much money I've gained, my tax rates, et cetera. But the, the, you know, I'm, I'm still, I'm not obsessed with money. I think about it all the time. I'm trying to get a lot more. I'm, I'm giving it away. I, five, five years ago, I decided I was going to give away every dollar I made in current income. Um, because I want to start catching up to the non-philanthropic Scott for the first 45 years of his life, but I'm still trying to make a shit ton of money. I still feel financially very insecure. I still worry about a recession becoming a depression, and I'm the guy who lost it again. I've lost it all a couple times, and so I don't feel I'm at that point where I don't have financial anxiety. I do sleep with one eye open. The big, you know, I sold my first company for Twenty-eight mil…

AI assessment note: “I still don't, I still haven't hit that point. I'm still very anxious”

Q 17, so I've never really had adulthood without bluntly running my business, so I didn't really know who I am. It's why I never go on holiday, because you're forced to reflect on life, and I don't really want to reflect on life without work, because I, I don't know who I am. Did you know who you were? Did you learn who you were from tough times, good times?

A It's an interesting question. I think you're being hard on yourself. I think you've decided that you're, first off, it sounds like you're very blessed that you knew what you wanted to do at a young age. At 17, I thought, you know, when I was very young, I thought I was going to be an athlete. At 17, I thought I was going to be a pediatrician. At 22, I thought I was going to be an investment banker. And then by 24, I was living with my mother and had no idea what I was going to do. So you're sort of blessed that you had that kind of focus and drive at such an early age. That's a gift. And I don't think there's anything wrong with Kind of, uh, similar to you once I got going and got some professional traction, I, my entire self-worth and identification was through my professional success or lack thereof. That's how I identify who I am. That's where I get my confidence. And then when I finally got to economic security, I thought, all right, what was economic security for you? Yeah, I had a number two and I just, I wrote a book on financial security for me. It was like, I wanted to assume that four percent of my number would give me Passive income that would be way more than I needed to live well. Uh, my number was one hundred and fifty million, uh, because I thought, uh, it would be hard for me to spend half a million dollars a month, although I figured out how. And four percent o…

AI assessment note: “my entire self-worth and identification was through my professional success or lack thereof.”

Q So you don't agree with cut out people from your life who are negative energies, who are negative forces?

A Oh, sure. You don't, don't be, I mean, I shed friends all the time. I shed relationships. You know, I used to be focused on business. You're, you're, it sounds like you're in, uh, you're in finance. It gets pretty brutal sometimes, and I've been, in my opinion, sort of, Not abused, but treated poorly by business partners, venture capitalists, and I get, I struggle with anger, and I thought, oh, I'm gonna serve this guy a cold lunch someday. And it lives rent-free in my head. And one of my mentors, Hamid Mogendam, said to me, um, he said the best, he's like, you really want to get at this guy? He was a VC, one of the most powerful VCs in the world, washed me out of my stake in my company, kicked me off the board. He's like, you really want to get back at him? I'm like, yeah, what are we gonna do? And he's like, lead a fucking amazing life. That is the best revenge. And so, if I don't, if I have a bad business partnership, something I'm proud of, I have never sued or been sued by anybody. If I have a bad relationship with someone or I feel like I've been wrong, I just don't work with them again. There are some friends in my life that slowly but surely I just do a slow fade from, I don't, I've never been tolerated an abusive relationship romantically, but generally with your important relationships, I think a healthy way to approach it is just say, I'm going to put away the scorec…

AI assessment note: “I shed friends all the time. I shed relationships.”

Q great, high, well-paid jobs. They've crushed, and they're angry, Scott. They're told, hey, I've been told for a decade that work is the most important thing, career, career, career. And actually, I'm sitting here now where my eggs are not what they used to be, my fertility is not what it used to be, and I feel like I was misadvised by the system. What would you say to them?

A I think economic security is really important. And I mean, so I was raised by a single immigrant mother who lived and died of secretary. And the biggest source of stress in our life, quite frankly, Harry, was we just didn't have enough money. And it was very, in a capitalist society in America, when you don't have a lot of money, even as a kid, I remember registering these little things. It's like a ghost is following you around telling you you're not worthy. Like, I literally felt like there was this ghost following me and my mom around saying you're not worthy. And, and I think poor people get those messages every day. And I think if you're a poor woman or a woman who doesn't have a lot of economic prospects, I think that's an ugly place to be. So I don't fault those women for wanting to excel academically and engage in the fruits of a capitalist society and develop economic security. I'm not sure I would advise them to have done anything different. The hard part is if you're going to have an honest conversation about mating, you have to have an honest conversation, and it's the following. The guy that takes that route and becomes a baller at a law firm becomes sexy, right? You make more money, you're more attractive as a man. You make more money as a woman, you're just a woman making more money. And so the, the, the sort of increase in mating opportunities for men who get mo…

AI assessment note: “I'm not sure I would advise them to have done anything different.”

Q How do you know when to settle with compromise versus look for perfection?

A Oh, I don't know. I, I think everyone's different, but for me it was, but for me it was willing to throw up the deck of cards that was my life and let them land anywhere because I didn't want to lose this person. I had no desire to have kids, and this person made it clear to me that, okay, if you don't want kids, I get it, but we're, I need to move on because I want to have kids, and so I was willing to reconfigure my life because the idea of not having that person in my life was really upsetting to me. So that, you know, that either happens or it doesn't. The hard part is, as you get older, you become more set in your ways. But I, I would imagine what happens to the majority of us will happen to you, and that is you'll meet someone and you'll decide that the sacrifices are worth maintaining that person in your life. I think that's general. I don't think any guy ever decides. I mean, this is terrible. I think most men who are successful Like the optionality of not being committed or married or having kids, and then I think what happens a lot is your partner's not up for that, and, and, and basically says, okay, it's decision time, and you make that decision, and then hopefully you, you look back and think that was a good idea, that was the right decision.

AI assessment note: “you'll decide that the sacrifices are worth maintaining that person in your life”

Q What were you most afraid to ask for?

A Yeah, I've always had that. I've always had a certain level of imposter syndrome, so I didn't think I was gonna get into college, and I didn't, and then I got in, and I felt like I fooled them, and then I got into Morgan Stanley, and I felt like I'd fooled them. I've, so I've always been, but I've always done it, but I've always felt like imposter, if you don't feel imposter syndrome, you're either arrogant or not reaching, Far enough. So I, I'm consistently kind of embarrassed to ask for stuff, but I never got in the way. I don't, I got past that pretty early. I, one of the best things that happened for me was I ran for sophomore, junior, and senior class president in high school and lost all three times. And based on my track record, I decided to run for student body president where I lost. I asked seven women to prom. All seven said no. And I think that has built a level, it didn't traumatize me, it built a level of calluses and scar tissue where I'm sort of, you know, I'm just not afraid of rejection. I think that's, if I could teach my kids any skill would be one, to communicate, but two, to be able to endure rejection, to be able to mourn and move on.

AI assessment note: “I'm consistently kind of embarrassed to ask for stuff, but I never got in the way.”

Q If you start a cycle of breakups, where does it end?

A Well, you have thoughtful economists and people who said, for example, IPG and Omnicom, their merger was held up by the FTC. I think that's ridiculous overreach. And that's Elon Musk trying to get in the way of these companies through some bullshit notion that somehow they've formed a cartel to not advertise on X and is getting in the way of their merger when these are companies merging to survive. These companies are not a threat. They're not a competitor. They're not charging brands too much money or, or have a monopsony or suppliers. This is, that was ridiculous. So there, there are, Eras of overreach, but the number of FTC investigations has dramatically declined since the seventies and the eighties. And very few mergers or acquisitions are blocked now, and I would argue, so I, I don't, you have to have thoughtful, you know, well-compensated, smart economists and, um, lawyers who look at this stuff and say, would we be better off if, you know, Amazon didn't have Instagram, um, if it was an independent company, if these two weren't cooperating and coordinating. The largest search engine in the world is Google. The second largest is YouTube. Should they be cooperating and coordinating, or would the ecosystem be healthier, more profitable, more jobs, more tax revenue, if these two were separate companies with their own, uh, objectives?

AI assessment note: “you have to have thoughtful, you know, well-compensated, smart economists and, um, lawyers”

Q Did you, you know, you're, you're, you're incredibly successful, you're incredibly influential, but when you're at Davos, you're around, like, literally the people controlling the world of the most famous, powerful people on earth. Was there anything that you learned?

A I don't think I was able to discern differences or draw anything, conclusions around these type of people. The things I walked away from Davos with is that the last time I was there in 99, it was about e-commerce, and the U.S. brand was capitalism consumption and Bill Clinton. Now it's about AI. Everyone was talking about AI, and it's about the American brand is chaos, coercion, and I don't know, compliance. I, I just, I find the US brand has fallen so far so fast. I came away from Davos unsettled about how unsettled the world is right now, but I don't think I Jew any. I personally, and people hate this, the billionaires I know, I know about a dozen. Are actually really good people. The Bernie Sanders, Elizabeth Warren, like, you can't be a billionaire unless you're a bad person. Well, okay, Elizabeth Warren, you're worth twenty million. Does that mean you're only a fifties as bad, but you're 20 times worse than a millionaire? I don't buy the rich people are bad. I have generally found The distinct of the Epstein files, which I understand gives people the impression that once men get to this point, they feel like they're no subject to the rules. I think that's a really interesting discussion. I personally have found that billionaires are generally very high character people because the key to being really successful is to create allies along the way such that you're put in a ro…

AI assessment note: “The things I walked away from Davos with is that the last time I was”

Q You've, uh, you've talked a lot about marriage and this is our next question, but you said, uh, you talk about how important it is both financially and emotionally to marry the right person. So if we were gonna do, um, the, uh, the inversion of that, what would you say is the best and easiest way to marry the wrong person?

A Really thoughtful question. Um, when I was a young man and I was trying to find romantic or sexual partners, I was constantly trying to figure out what person do I need to be that will get them to like me. I was trying to constantly figure it out. Do I need to act indifferent? Like I don't care. I, uh, I was just, it wasn't me establishing a relationship with this person or on a date with this person. It was my representative. Who tried to figure out what I thought this person would want from me, or specifically how I could convince this person to have sex with me. And what you realize is the person you want to end up with is the person where you get to be you and they like you despite the real you. Like, and the best relationships I've ever had are people that I, like, I can be me around, and they just really like me for me. Like, I, I look back on sources of confidence. My first serious relationship with a woman named Melanie Kagan, and I was crazy about her, and she was crazy about me, and I think that confidence of someone who actually knows you, And you can be honest with and call and who sees your insecurities and, you know, and still really is into you. I just think I, if I could wish anything on a young person, it would be the opportunity to be who you are around somebody and find out that people, there are people out there who will love you for that. I just think that …

AI assessment note: “It was my representative. Who tried to figure out what I thought this person would want”

Q What age did you, uh, start traveling with your kids? I've got a, a two-year-old and a, and a, and a three-month-old, and I'm looking forward to traveling.

A Uh, the three-month-old is actually easier to travel than the two-year-old. Zero to three is awful. It gets better. You're, you're no use. Your job is to be supportive of your wife and make money. That's it. You add no value. You'll pretend to like it. You'll come on podcasts and say, oh, I love it. She did the cutest. It's awful. And keep them away from a large body of water. That's your entire job right now. And then at about age three, they become less awful. And then about from like four to 14 is the golden decade. Oh, do everything. I mean, again, these are incredible stories of privilege. But even if you don't have money, take your kid. The best week I've had in probably the last three years, I did a college tour with my son. We planned it out together using AI. Should we go to Indiana? Should we go to Wash U? Should we go to Michigan State? What if we go to If we go to Michigan, can we see a football game? If we go to UNC, can we see a basketball game? I mean, we did nine schools in nine days, and it was just, it was just amazing. And, but, uh, take time with your partner, take them somewhere cool and amazing. Spend, there's a ton of research on this. People overestimate the amount of happiness they'll get from things, and they underestimate the amount of happiness they'll get from experiences. And some, drive a Hyundai and take your husband to Africa.

AI assessment note: “from like four to 14 is the golden decade. Oh, do everything.”

Q 17, so I've never really had adulthood without bluntly running my business, so I didn't really know who I am. It's why I never go on holiday, because you're forced to reflect on life, and I don't really want to reflect on life without work, because I, I don't know who I am. Did you know who you were? Did you learn who you were from tough times, good times?

A It's an interesting question. I think you're being hard on yourself. I think you've decided that you're, first off, it sounds like you're very blessed that you knew what you wanted to do at a young age. At 17, I thought, you know, when I was very young, I thought I was going to be an athlete. At 17, I thought I was going to be a pediatrician. At 22, I thought I was going to be an investment banker. And then by 24, I was living with my mother and had no idea what I was going to do. So you're sort of blessed that you had that kind of focus and drive at such an early age. That's a gift. And I don't think there's anything wrong with Kind of, uh, similar to you once I got going and got some professional traction, I, my entire self-worth and identification was through my professional success or lack thereof. That's how I identify who I am. That's where I get my confidence. And then when I finally got to economic security, I thought, all right, what was economic security for you? Yeah, I had a number two and I just, I wrote a book on financial security for me. It was like, I wanted to assume that four percent of my number would give me Passive income that would be way more than I needed to live well. Uh, my number was one hundred and fifty million, uh, because I thought, uh, it would be hard for me to spend half a million dollars a month, although I figured out how. And four percent o…

AI assessment note: “my entire self-worth and identification was through my professional success or lack thereof.”

Q I saw that you spoke recently about the kind of radicalization or antagonism within young men when it comes to the amount of swipes correlated to the amount of coffees on Tinder and dating apps. Can you talk to me about how you think about kind of male rejection through dating apps and how that leads to antagonism tension against more things than just dating?

A A common thread through history is that the greatest innovation in history is not the iPhone or the semiconductor or vaccines. It's the American middle class. And you had this huge body of educated, progressive, um, the populace who was productive and created so much tax revenue and so many rights, and it became just this, this anomaly. Because typically the way societies work is that a small number of men get all the mating opportunities. That has how, that's been the natural order of things, is that a very successful man has multiple, can basically engage in polygamy. And at the end of World War II, we brought home seven million men from overseas. They were in uniform. They had demonstrated heroism. We put a ton of money in their pockets to VH loans, National Construction, Highway Construction Act. Our manufacturing base was unbelievable, and there were a ton of middle class, and basically we created a ton of very attractive men that women were attracted to, and we had the kind of middle class, two-car, you know, home. And the homes were so productive and so successful, they thought, let's Bring women and non-whites into this prosperity. And they created a huge tax base, educated populace. And what we have now is I think we're reverting to the way the majority of history is, and that is a small number of men who can demonstrate wealth or signal wealth online, whether it's thr…

AI assessment note: “46 of the women will show all of their attention exclusively to just four men”

Q Do you agree never go to bed angry?

A Uh, yeah, I, I, what I have a practice with my partner is that I get in bed no matter what time it is, I stay up late, and I, you know, um, you know, I, um, it sounds very hallmark, I spoon her, so yeah, we don't go to bed angry, we, and my partner is so vocal and willing to tell me everything that's, that, that's not ideal, that we don't, it's almost impossible. Things, things very rarely go unsaid, so yeah, I don't, I, I would just say try to be more Um, motive, and tell people what you're thinking, and if you're upset, and be generous, and listen to them, and everyone has their own dynamic. I don't know. I, the, the Northern Europeans just walk around morose all the time, and it seems to work for them. I, I think it, a lot of it is just Um, situational, but I think more than I'll go back to one of the things. I think it's just so important to articulate how fortunate you are and we built together. And I send my partner pictures of my kids when they were younger and I constantly highlight, wow, isn't it great that we can do this? And she will say to me, you know, I'm really happy right now. And that makes me feel really good. Cause I see it as a reflection on my competence as a man that she's really happy. But all of this is situational, you know, it's, it's the biggest decision you'll make. It's not where you work or where you live. Your biggest decision you make is who you …

AI assessment note: “so yeah, we don't go to bed angry, we, and my partner is so vocal”

Q now the fall of 20 24, I think, uh, legally we're not allowed to have a pod, a business podcast without talking about AI. So, um, a couple of AI questions. Uh, one from Shelley who emailed us, um, asking us to ask you, aside from upskilling, up, upskilling with AI, what should white collar workers be doing to change their approach to both their jobs and the job market?

A I use AI a lot, and what I've said is AI is not gonna take your job. Someone who understands AI is gonna take your job. So I've used AI for every component of my job, and I find it can't replace anything. When I first started playing with AI, I thought, oh, I just got a seven-figure book deal for, to write a book called The Algebra of Masculinity. I'm gonna have, I wanna write the first chapter and the last chapter, and I want the middle 10 chapters written by AI with really thoughtful prompts. And it is what it is. It comes back very anodyne. It comes back like a GPU wrote it. It's just not gonna work, but I can type in, give me 10, uh, rites of passage from boyhood to manhood across different cultures, and seven of them I knew, but three of them I didn't, and then I'll go do a deep dive on the three, or, uh, it can't produce a board deck for me to present to a board of a company I'm running, but after I do the deck, I can feed it into AI and say, pretend you're a tier one VC who is a bit of a, you know, is a bit of a hard ass and, and is very focused on shareholder value through technical, technical innovation. What are likely the questions I'm going to get from this person? And you upload. So I think of it, the way, the way I use AI is as a thought partner. What I would say is, it's just start using it and your, your own mind will start figuring out ways you can incorporate …

AI assessment note: “What I would say is, it's just start using it”

Q What were you most afraid to ask for?

A Yeah, I've always had that. I've always had a certain level of imposter syndrome, so I didn't think I was gonna get into college, and I didn't, and then I got in, and I felt like I fooled them, and then I got into Morgan Stanley, and I felt like I'd fooled them. I've, so I've always been, but I've always done it, but I've always felt like imposter, if you don't feel imposter syndrome, you're either arrogant or not reaching, Far enough. So I, I'm consistently kind of embarrassed to ask for stuff, but I never got in the way. I don't, I got past that pretty early. I, one of the best things that happened for me was I ran for sophomore, junior, and senior class president in high school and lost all three times. And based on my track record, I decided to run for student body president where I lost. I asked seven women to prom. All seven said no. And I think that has built a level, it didn't traumatize me, it built a level of calluses and scar tissue where I'm sort of, you know, I'm just not afraid of rejection. I think that's, if I could teach my kids any skill would be one, to communicate, but two, to be able to endure rejection, to be able to mourn and move on.

AI assessment note: “I'm consistently kind of embarrassed to ask for stuff, but I never got in the way.”

Q Does one blame the public for the knowledge inequality?

A Well, you know, the world is what we make of it. I find that we always have this idolatry of the voter that, oh, it's never the public's fault, and my sense is the public, um, I think in the U.S., a lot of our problems stem from, uh, what is a lack of investment or underinvestment in K through 12, and that we aren't producing critical thinkers who understand Not only the government, don't understand how fortunate they are to live in a democracy, don't appreciate America, don't appreciate the rights and the freedoms and our victories that we should celebrate together, don't, um, understand basic financial literacy, aren't encouraged to vote. I, I, I, I get that government is bad and, you know, but the question is why aren't better people running? And the answer is, whenever I talk to really good people that would like to run, they're like, are you fucking crazy? I would never put myself through that. And so, why is that? Why have we made it so ugly and awful for good people to run?

AI assessment note: “we always have this idolatry of the voter that, oh, it's never the public's fault”

Q If you start a cycle of breakups, where does it end?

A Well, you have thoughtful economists and people who said, for example, IPG and Omnicom, their merger was held up by the FTC. I think that's ridiculous overreach. And that's Elon Musk trying to get in the way of these companies through some bullshit notion that somehow they've formed a cartel to not advertise on X and is getting in the way of their merger when these are companies merging to survive. These companies are not a threat. They're not a competitor. They're not charging brands too much money or, or have a monopsony or suppliers. This is, that was ridiculous. So there, there are, Eras of overreach, but the number of FTC investigations has dramatically declined since the seventies and the eighties. And very few mergers or acquisitions are blocked now, and I would argue, so I, I don't, you have to have thoughtful, you know, well-compensated, smart economists and, um, lawyers who look at this stuff and say, would we be better off if, you know, Amazon didn't have Instagram, um, if it was an independent company, if these two weren't cooperating and coordinating. The largest search engine in the world is Google. The second largest is YouTube. Should they be cooperating and coordinating, or would the ecosystem be healthier, more profitable, more jobs, more tax revenue, if these two were separate companies with their own, uh, objectives?

AI assessment note: “you have to have thoughtful, you know, well-compensated, smart economists”

Q Do you agree never go to bed angry?

A Uh, yeah, I, I, what I have a practice with my partner is that I get in bed no matter what time it is, I stay up late, and I, you know, um, you know, I, um, it sounds very hallmark, I spoon her, so yeah, we don't go to bed angry, we, and my partner is so vocal and willing to tell me everything that's, that, that's not ideal, that we don't, it's almost impossible. Things, things very rarely go unsaid, so yeah, I don't, I, I would just say try to be more Um, motive, and tell people what you're thinking, and if you're upset, and be generous, and listen to them, and everyone has their own dynamic. I don't know. I, the, the Northern Europeans just walk around morose all the time, and it seems to work for them. I, I think it, a lot of it is just Um, situational, but I think more than I'll go back to one of the things. I think it's just so important to articulate how fortunate you are and we built together. And I send my partner pictures of my kids when they were younger and I constantly highlight, wow, isn't it great that we can do this? And she will say to me, you know, I'm really happy right now. And that makes me feel really good. Cause I see it as a reflection on my competence as a man that she's really happy. But all of this is situational, you know, it's, it's the biggest decision you'll make. It's not where you work or where you live. Your biggest decision you make is who you …

AI assessment note: “so yeah, we don't go to bed angry”

Q today is like, um, you know, Vanguard, State Street, and BlackRock own, you know, let's call it, 80% of the S&P and 40% of the broad market, but then people will say, but they're passive. They're passive investors. What do you think about that? Do you think they actually change governance on most of our companies in the, in the U.S. because they own them, or are they truly passive?

A It's a really interesting question. So concentration of ownership is just a bad, is this bad to begin with? Although I would argue that those industries, I mean, it's an interesting question. So there's two sides to it. I love low cost index funds. I, you want to have some fun. Everybody believes they're smarter than your average bear. I'm not immune. I stock big, but what I would tell young people is 70% of any of your savings when 99% of your savings is going to come from money you can't touch, whether it's equity or things that automatically go into a savings account. Uh, low cost index funds. The, I work with the brightest people in finance. I've advised the most prestigious VCs, private equity funds, and my sum net conclusion is no one has any idea. And the VCs that outperform are the ones that get better deal flow. But if you took the entire alternative, the entire alternative investments industry, any logo on CNBC, anyone that advertises, any hedge fund, anywhere, it's essentially a grift. And what they, If you look at their performance, they've exactly underperformed the S&P by the amount of their fees.

AI assessment note: “I love low cost index funds. I, you want to have some fun.”

Q Does one blame the public for the knowledge inequality?

A Well, you know, the world is what we make of it. I find that we always have this idolatry of the voter that, oh, it's never the public's fault, and my sense is the public, um, I think in the U.S., a lot of our problems stem from, uh, what is a lack of investment or underinvestment in K through 12, and that we aren't producing critical thinkers who understand Not only the government, don't understand how fortunate they are to live in a democracy, don't appreciate America, don't appreciate the rights and the freedoms and our victories that we should celebrate together, don't, um, understand basic financial literacy, aren't encouraged to vote. I, I, I, I get that government is bad and, you know, but the question is why aren't better people running? And the answer is, whenever I talk to really good people that would like to run, they're like, are you fucking crazy? I would never put myself through that. And so, why is that? Why have we made it so ugly and awful for good people to run?

AI assessment note: “why aren't better people running? And the answer is, whenever I talk to really good”