The Exchanges

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 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 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 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”