Scott Galloway on Billionaire Happiness, Money & Self-Worth | Why We Should Drink More & Not WFH

For the first time in our nation's history, a 30-year-old isn't doing as well as his or her parents were at 30. If a man hasn't cohabitated or been married by the time he's 30, there's a 1-in-3 chance he ends up a substance abuser. When a young man doesn't have the guardrails of a romantic relationship, he often channels that energy into video games, porn, and conspiracy theories.

If you want to score above your weight class economically and romantically, get out a big spoon. Get ready to eat [__]. Endure rejection.

Scott, I've wanted to do this one for a long time, so thank you so much for joining me today.

Oh, you're so welcome. It's good to be here.

1. Should We Be Worried About Market Concentration?

When we look at the biggest companies in the world, often considered the Mag 7, what we're seeing is this kind of concentration of value in public markets. I really wanted this to be a free-flowing discussion because I bluntly respect your brain so much. But you see this concentration of value like we've almost never seen before. Does that worry you, and what does that mean for the future value dispersion in public markets, in your mind?

I think it's hugely worrying because you have essentially 34% of the S&P represented by 7 companies, and 50% of the equity value of the world and 70% of the enterprise value, if you include the debt, wrapped up in the US economy, which has 7 companies. If any of those 7 companies sneeze, the whole economy, and potentially the whole global economy, catches a cold.

In addition, it's very hard for small and medium-sized businesses to attract the kind of human and financial capital to be competitors. When you have the most valuable parts of our economy—e-commerce, where one company does between 50% and 70% of all e-commerce, depending on how you categorize e-commerce; social media, which is the most powerful thing to happen in traditional media, or what we refer to as media, where one company has a 75% share of social; and search, at 90% and 89%—and then you have AI, the biggest revolution of the last several decades, where 90% of the processing has run through one company's GPUs and 85% of the queries have gone through one company, I think a concentration of power and shareholder value makes a company or an economy less robust and less diverse.

I think it's bad.

How does this pan out? Do we have $10 trillion companies within the Mag 7, or do we see the traditional cycle of companies—growth, sustenance, and then decline—and this is just another cycle?

It's an interesting question because some people would say that ultimately the market figures it out. Look what's happening with Alphabet. Google is starting to lose share to OpenAI, right? Eventually, a competitor comes along, whether it's BYD and Tesla. But I would argue, what happens between now and then?

I think it is very difficult for companies. A lot of the retail landscape in the US has largely been decimated, especially retail, because Amazon could put forward cheap capital and sell a dollar's worth of products for 90 cents and starve out other e-commerce players. I was one of those companies.

Winning in our economy has become a function of establishing a great product, establishing the perception that you're the market leader such that you can attract cheaper capital, and essentially overwhelming the competition with capital.

At the end of World War II, the German army had better soldiers, a better kill ratio, better tanks, better planes, and better officers. But because we cut off their supply routes, we had 38 gallons of gasoline for every 1 they had. We were able to overwhelm their superior Tiger tanks with our shitty Bradley tanks because we would never get within firing distance and could chase them around until they ran out of gasoline.

The business strategy that has built a lot of the most valuable companies in the world is now just to overwhelm them with gasoline. Netflix can spend $18 billion. Netflix establishes itself as the streaming leader, accesses the public markets, has a fantastic story, and accesses the cheapest capital in media. Time Warner and HBO can't compete with these guys. Disney can't compete because their shareholders have wrapped their lips around the crack pipe of profits and demand a certain level of operating margin, which Netflix shareholders don't demand. Netflix can spend $18 billion on content, and no traditional media player can even come close.

Amazon can make these staggering investments in supply chain that no other retailer can even come close to. When you talk about brand building, I think the greatest ROI in what you would call—I don't know if it's brand building—is communications. If you establish a reputation as the market leader, constantly put out press releases about your innovation and your leadership, and get that sort of Pepsi Generation, Amazonian-like feel, your stock gets bid up. Then you use that cheap capital to start reinvesting or making acquisitions, and you can literally pull away from the pack.

Everything eventually ends. There is no company that will be around forever. All of the biggest companies in 1900, in the Dow, none of them are around. All of these companies will go away. But the question is, that's not the right question. The question is: between now and then, would we have a more robust economy if we broke up Alphabet and YouTube was its own company?

Would there be more jobs, more competition, more shareholder value, and more choice, such that more advertisers wouldn't have to advertise through Meta and could maybe go to a platform that offered more stringent child safety or age-gating? I think competition is a good thing. If you look at these companies when they're broken up, breakups are one of those few things in economic history that almost always work for almost everybody.

The only person who loses is the CEO who wants to sit on the Iron Throne of all 7 kingdoms, not just Westeros. Eventually, all these companies will go away. But between now and then, I think we need to be more robust about antitrust.

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

You have thoughtful economists and people who have said, for example, that the IPG and Omnicom merger being held up by the FTC is ridiculous overreach. That's Elon Musk trying to get in the way of these companies through some [__] notion that somehow they've formed a cartel to not advertise on X, and he's getting in the way of their merger when these are companies merging to survive.

These companies are not a threat. They're not charging brands too much money or have a monopsony over suppliers. That was ridiculous.

There are eras of overreach, but the number of FTC investigations has dramatically declined since the 1970s and 1980s, and very few mergers or acquisitions are blocked now. I would argue that you have to have thoughtful, well-compensated, smart economists and lawyers who look at this stuff and say, would we be better off if Meta didn't have Instagram? If it was an independent company?

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, and produce more jobs and tax revenue if these were separate companies with their own objectives?

Do you believe in government intervention?

2. Does Scott Believe in Government Intervention?

Yeah. It's why we're not speaking German. The government intervenes all the time.

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

Yeah, but it's a balance. I think one of the strengths of America is that we have a tendency to have more of a Wild West attitude, and I think that to err on the side of too little regulation is probably better than too much regulation.

If you were to try and come up with 3 or 4 reductive reasons why the US has created so much more economic value than Europe, I think if you're intellectually honest, you would say that in the US, companies are allowed to ask for forgiveness, not permission. There's some value to that.

There's also a downside. We have a 60% uptick in teen suicide in the US. I don't put it all at the hands of social media, but it's definitely played a role. Europe is more thoughtful about what privacy regulations are right, and I do think there is an economic advantage to erring on the side of a lighter touch of regulation. But it also comes with some externalities.

Again, that's why we have a government and thoughtful people who can hopefully balance economic growth and innovation, risk, being aggressive, and breaking some [__], while also recognizing that Mark Zuckerberg and Shou Zi Chew are lying to us. It probably doesn't make sense for a 12-year-old to be spending 14 hours a day in the high school cafeteria known as Instagram.

I think it's a balance, and I'm not sure. I wonder if the EU is too regulated and America is not regulated enough. I feel like your question is pregnant with a comment. What do you think?

I believe in minimal government intervention. I believe in Adam Smith's invisible hand. I think I just see European regulation getting in the way of so much innovation every single day as a venture investor and creating labor challenges, innovation challenges, and research and development challenges.

I think I'm stifled by regulation on a daily basis, which makes me negatively inclined. But do you think, at some point, thoughtful regulation is needed? For example, I think that we needed more regulation in crypto in the last administration to create just a level playing field.

I feel like a lot of the more innovative companies in the crypto space just wanted a set of rules they knew would hold, that they could plan against.

I completely agree, and I think clarity is everything. I think it's where most governments fail to provide clear guidance as to what will happen in the future, and that's all people want. I think I just don't have trust in the institutions that make these regulations, which means that I don't want them.

But you are those institutions. You live in a democracy. You get to vote on who and what runs those institutions.

I do, but I don't get to vote in any way in terms of who should be running them. I think we both agree that the quality of politicians is very low.

Yeah. No, look, that's a fair point. But I agree. I just wish there were better-quality politicians. What I think needs upgrading is our public, and no one likes to say this: I think it's our public that are fucking idiots, that don't think critically and don't look at the issues and don't vote for good candidates and don't cut through the noise in their social media.

They are much more inclined to believe something bad about somebody as opposed to doing the hard work of really understanding the issues, voting for good candidates, being supportive, and showing people a little bit more grace.

Do you blame the public for that? I agree with you totally, but when you look at the knowledge inequality both in the US and the UK, I think the majority do not spend the time to do the work, and then are fed massive misinformation, which kind of feeds it in a challenging way. But does one blame the public for the knowledge inequality?

Well, the world is what we make of it. I find that we always have this idolatry of the voter: “Oh, it's never the public's fault.” My sense is the public—I think in the US, a lot of our problems stem from a lack of investment or underinvestment in K–12, and that we aren't producing critical thinkers who understand not only the government, but also how fortunate they are to live in a democracy.

They don't appreciate America. They don't appreciate the rights and the freedoms and our victories that we should celebrate together. They don't understand basic financial literacy, and they aren't encouraged to vote. I get that government is bad, but the question is: Why aren't better people running?

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.” So why is that? Why have we made it so ugly and awful for good people to run? Because the process of getting impact is so difficult, it is so difficult to make the change that you want to make. It's not the money. People are like, “I'll pay them more.” It's never the money.

It is impossible to do what you want to do when in a position of power. I literally just interviewed a prime minister the other day, and I said, “What do you know now that you wish you'd known?” And she said, “Even when you're in the top seat, there's very little you can actually do.”

3. Why Young People Have a Right to Be Angry?

Yeah, look, that's fair. What we have in the US, though, is interesting. I think that's largely true, but I think a lot of people would argue that a democracy is about having these gears that never move too fast, such that you have to be more thoughtful, even at the cost of bureaucracy. I thought it was interesting you said that young people had a right to be angry, or deserved to be angry.

Do you stand by that when you think about that today, or, in your words, that the world is what you make of it?

Well, yeah, but young people, to a certain extent, inherit a world that is set up for them by people before them. In the US—and I'm not as familiar with this data in the UK, maybe you are—for the first time in our nation's history, a 30-year-old isn't doing as well as his or her parents were at 30.

Every year in the US, we spend $12 on seniors for every $1 we spend on kids. The average 70-year-old in the US is 72% wealthier than they were 40 years ago. The average person under the age of 40 is 24% less wealthy.

What seniors in the US have figured out is a way to vote themselves more money. You could argue, “Well, if young people don't vote, that's going to continue.” But children aren't allowed to vote. Every year, young people transfer $1.3 trillion in the form of Social Security payments to the wealthiest generation in the history of the planet: seniors.

When you see the cost of education and the cost of housing skyrocketing, when you see massive prosperity and then it's rubbed in your face every day—210 times a day, you're reminded that you're not on a Gulfstream or partying in St. Barts—it makes you feel bad about yourself. Meanwhile, you just see unbelievable economic growth and prosperity, but it doesn't appear that young people are sharing in it to the same extent.

Forty years ago, 60% of 30-year-olds had at least 1 child. Now it's 27%. It's because they've decided they don't want kids, or maybe they just can't afford them.

When institutions like mine at NYU take pleasure in creating artificial scarcity so we don't let in as many kids as we could, such that we can drive up the cost of tuition faster than inflation and pay ourselves more for less accountability, and then we let people who own homes implement zoning and NIMBY policies that make it very difficult for young people to afford a home, I think young people have a genuine, legitimate claim that the economy is not working for them.

The incumbents, specifically people my age, have weaponized government to transfer money from them to us.

What do you think is the core way that they have weaponized government to work for you, and what would you say is the best way to reverse that?

4. Why the Tax Code Is Rigged Against the Young

The tax code. It's the boring shit that moves the needle. I make most of my money buying and selling stocks and companies, and we've decided that people who can do that should pay a lower tax rate. The people who can do that are old and rich.

Old, wealthy people make their money from buying and selling assets. Young people make their money from salary and working. Why am I paying 22%, and the top income earner on earned income is paying 37%?

The second-biggest tax deduction is mortgage interest. Old people own homes; young people rent. Why is the biggest cost for old people tax-deductible, but the biggest cost for young people is not? Even the 2 biggest tax deductions are just a transfer of wealth from the young to the old.

So I think it starts with tax policy. Essentially, Social Security tax: I make a lot of money, and I pay $9,000 every year in Social Security because it taps out at 6% up until $160,000. An analyst working for me who makes $160,000 also pays $9,000.

If you look at the tax code in the US—and I apologize for deferring to the US, but I just know more about it—the tax code has gone from 400 pages to 4,000. Those incremental 3,600 pages are basically full of loopholes for corporations and the wealthy to get wealthier and wealthier.

Some solutions: I think you should eliminate the capital gains tax. I think we should have 1 tax code, and it's AMT. It's non-negotiable. Call it 30%: you make over $100,000 a year, you pay 30%; you make over $1 million a year, you pay 50%.

That sounds like a lot, but Daniel Kahneman's research has shown that above $1 million, you don't get any incremental happiness. Whereas if you have universal child care or Medicare and you can take a household's average income from $30,000 to $40,000, it's a huge leap in happiness.

So an alternative minimum tax for corporations and the wealthy, a tax holiday for people under the age of 30, more vocational programming that helps create more on-ramps for young men that have been sequestered from them in an information age, mandatory national service so young people can find friends, mentors, and mates, and more tax credits for third places so people can find places to meet each other instead of swiping.

I think there are a lot of things we could do to reverse this really awful trend of obesity, anxiety, and depression among young adults.

5. Tax Changes That Would Make Young People Rich Again

There are so many elements in every statement you make that I want to unpack. You talked about children and people delaying the decision to have children, and then merging that with the anger. I have so many female friends who are 35 to 40, who are partners at law firms and partners at venture firms, with great, high-paid jobs. They've crushed it, 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?

I think economic security is really important. I was raised by a single immigrant mother who lived and died as a secretary, and the biggest source of stress in our life, quite frankly, Harry, was that we just didn't have enough money.

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. I literally felt like there was this ghost following me and my mom around, saying, “You're not worthy.”

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, that's an ugly place to be. So I don't fault those women for wanting to excel academically, 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. The guy who 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. The increase in mating opportunities for men who get more successful is exponential. The increase in mating opportunities for women as they become more financially viable is just flat.

75% of women say economic viability is hugely important in a mate. It's only 25% of men. We have this weird externality where, as women become more successful, it doesn't mean they become more attractive to the opposite sex. But what we also have is that, as women become more economically successful, their pool of viable mates goes down because women mate socioeconomically horizontally and up, and men horizontally and down.

If you will, the metaphor—I’m a fan of this podcast called Modern Wisdom from Chris Williamson—he calls it the high-heels effect. The majority of women will not date a man shorter than them. Dating apps show that the majority of women will not date a guy shorter than them. Economically, women are getting taller every year and men are getting shorter.

When you hear people all the time say, “I know all these wonderful, attractive, high-character women and they can't find a man,” they can find a man. They just can't find a man they want to mate with because men aren't doing well. As a result, there's a mismatch in attraction, and the pool of viable mates—horizontal and up—for women who are doing well is shrinking.

A woman who's a partner in a law firm isn't interested in dating a guy who's a high school dropout, is a mechanic, and maybe making $60,000 a year while she's making $600,000 a year. Whereas, if a guy's making $600,000 a year and a woman in PR is making $60,000 a year and she's attractive, those are considered viable mates.

6. The Tinder Effect: Why Men Are Angry

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

A common thread through history is that the greatest innovation in history is not the iPhone, the semiconductor, or vaccines. It's the American middle class. You had this huge body of educated, progressive populace that was productive, created so much tax revenue, and created so many rights, and it became just this anomaly. Typically, the way societies work is that a small number of men get all the mating opportunities. That is how it's been—the natural order of things is that a very successful man has multiple partners and can basically engage in polygamy.

At the end of World War II, we brought home 7 million men from overseas. They were in uniform and had demonstrated heroism. We put a ton of money in their pockets through VA loans and the National Highway Act. Our manufacturing base was unbelievable. There were a ton of middle-class people, and basically, we created a ton of very attractive men that women were attracted to. We had the kind of middle-class, two-car home, and the economy was so productive and so successful they thought, “Let's bring women and nonwhites into this prosperity.” They created a huge tax base and an educated populace.

What we have now, I think, is that we're reverting to the way the majority of history has worked, and that is a small number of men who can demonstrate wealth or signal wealth online—whether it's through a Rolex or through slipstreaming into the information-age economy—can have a date every night. If there's 50 men on Tinder and 50 women on Tinder, 46 of the women will show all of their attention exclusively to just 4 men, leaving 46 men to fight over 4 women.

The scariest statistic I saw, which I think you referenced, is that, in order to get 1 coffee, a man of average attractiveness on a dating app has to swipe right or try to connect with 200 women. Then, if he's fortunate enough to get 5 coffees, which took 1,000 swipes, 4 of those 5 coffees will reconsider and ghost him, either not showing up or canceling. What this creates is a lot of resentment among men of average attractiveness. Then they become much more prone to misogynistic content and much more prone to nationalistic content.

This is a story as old as time. If you talk about young men who've been radicalized throughout history, generally they have a lack of romantic and economic opportunities. What I see is a group of men whom women find undateable, not economically or emotionally viable.

When a woman doesn't have a romantic relationship, she tends to channel that additional energy into much more productive things: her friend network and her professional life. When a young man doesn't have the guardrails of a romantic relationship, he often channels that energy into video games, porn, and conspiracy theories.

Back to your point about women feeling like they screwed up, what the data shows is distinct from the trope of the woman who's lonely and ends up with cats, who's a partner at a law firm and is miserable. The majority of the data shows that men actually benefit more from relationships than women. Widows are happier after their husband dies, and widowers are less happy. Men actually get more from a relationship than women.

The absence of relationships, the absence of young people hooking up and mating and committing to each other, actually has more of a downside impact on men. If a man hasn't cohabitated or been married by the time he's 30, there's a 1-in-3 chance he ends up a substance abuser. Men really need guardrails.

I think young men—I think there's a lot of data that shows that, while they're physically stronger, they're actually emotionally and mentally weaker than women. Without the guardrails of a romantic relationship, strong male involvement, a strong culture, and a good job, they're much more prone to substance abuse. They're much more prone to risky, aggressive activities, including gambling. They're much more prone to low-risk aggression and to finding their friends through Reddit or Discord, jobs, or trying to make money through crypto or stock trading.

You're a good-looking guy. You care about the way you look, you care about your career, and you signal a lot of very positive things that take a lot of work and energy. I worry a lot of men are not making those efforts because they think, “Why make those efforts? Why go through that when I just have porn?”

7. Remote Work & The Case for Alcohol

I worry a lot about young men and the lack of opportunities for creating a middle class through what I would hope are economically and emotionally viable men. I think remote work is a disaster for young people. I think they need to meet each other and learn how to read the room.

I think a close second is the anti-alcohol movement. I think the risks to a 25-year-old liver from alcohol are dwarfed by social isolation. When I was your age, I was drinking a lot, and it helped me find friends. It helped me find potential romantic partners. As I got older and got more serious about my career, I wound down my substance use because, like you, I said, “All right, shit just got real.”

For me, it was that my mom got sick. I didn't have enough money. It was very humiliating for me. So I thought I needed to get really, really serious about my career, and that involved a lot of things in my control, including dramatically reducing my consumption of alcohol and THC.

6% of teenagers are clinically addicted to alcohol or drugs. 24% are addicted to social media. So I jokingly say, put down your phone, go out, drink more, and make a series of bad decisions that might pay off.

When I ask people to reverse-engineer their closest friendships and their learnings around dating and romantic opportunities, did alcohol play a role in that? Almost everyone says yes. Then you say, “Was it a positive or a negative?” They're thoughtful and they slow down. Most of them say it was a positive.

I worry that this anti-alcohol movement, and people staying at home with Netflix because it's gotten so expensive to go out, means that people aren't bumping into one another. If someone had said to me, “Here on a dating app is a list of the attributes and a picture of who I ultimately ended up mating with,” I would have never chosen them.

But it was being in their presence, getting to know them at work, hanging out with them in a friend group or a sports league, and having an opportunity for me to demonstrate excellence. If you talk to people who've been married longer than 30 years, 80% of them say one was much more interested in the other at the beginning. It was always the man who was more interested in the woman.

Women have a much finer filter for mating because there's so much more downside to sex than there is for a man. But where do young men have an opportunity to demonstrate excellence? They're all on the dating apps, and all of a sudden it's about height and perceived resources.

You've seen this trend on TikTok where they say, “All right, describe your minimum height and your minimum income.” Six feet, six figures. That's 2.6% of the population of people who aren't married, aren't obese, and are under the age of 50.

Whereas, when you talk to married couples, they're like, “Yeah, I wasn't interested, but he was so good at what he did at work that I fell in love with him. I was at temple with him and I saw how kind he was to his parents, and I fell in love with him.”

We were in guitar class together, and I liked his hands. Where does a young man demonstrate excellence these days? Social media. Then it comes down to hiding money and basically trying to be someone that you're not.

8. The Loneliness Epidemic in Men

Exactly. Most of my feed is Scorpios or some fucking Mykonos club where the Rolex is on, and it's like, with my filter that gives me a six-pack, here I am on my jet. By the way, anyone who takes a picture of a jet does not own that jet, you know? So, I worry that we're creating unreasonable expectations for young people around what it means to be successful. Also, did you always know who you were?

I know this sounds like a weird one, but I've done what I've been doing since I was 17. So, I've never really had adulthood without, bluntly, running my business. I don'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 don't know who I am. Did you know who you were? Did you learn who you were from tough times, good times?

It's an interesting question. I think you're being hard on yourself. First off, it sounds like you're very blessed and that you knew what you wanted to do at a young age. 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.

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.

I don't think there's anything wrong with it. Similar to you, once I got going and got some professional traction, 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.

Then, when I finally got to economic security, I thought, “All right.”

What was economic security for you?

Yeah. I had a number, too. I wrote a book on financial security. For me, it was that I wanted to assume that 4% of my number would give me passive income that would be way more than I needed to live well. My number was $150 million because I thought it would be hard for me to spend $500,000 a month, although I figured out how, and 4% of $150 million is $6 million—$500,000 a month.

I got there about 10 years ago, and I started thinking about it. I'm very open about money because I think when rich people don't talk about money, it's an accidental or purposeful means of keeping lower-middle-income people down. If you want to be great at tennis, you should talk a lot about tennis. Young people need to speak to each other about money, their fears, and their anxieties. It's helpful.

I was very stressed out about money when I was your age. I didn't have a lot of it. So, I think it's really productive, educational, and cathartic to talk about money.

But when I got to my number, I was still very ambitious. I got all of my self-worth through money. My friends, my mating opportunities, all the incredible experiences, and my power came through money. So, I just naturally assumed that the more money I had, the more of those things I was going to have.

Then I had a couple of fairly close friends pass away unexpectedly. That happens when you're young. When you hit 50, you'll lose a couple of friends randomly. Strange genetic time bombs just go off, and you'll have a friend die of 6-month leukemia or some rare nerve disease. It does inspire some pause—or it did in me.

I thought to myself, I was in the midst of raising a private equity fund because I thought, you know what, deep down I want to be a billionaire. “Scott Galloway, billionaire” had a really nice ring to it. I thought I needed to get to a billion. I raised some money, or I got some money commitments.

Then I had some losses in my personal life. I thought, why on earth do I need to be a billionaire? I can do anything I want.

A huge unlock for me was financially deciding—and I do this every year—I look at my number. I know pretty much how much I'm worth. Goldman gives me a number every year. Anything above my number, I either spend it or give it away.

I love to spend money. I'm really good at it. I'm an indulgent person. I do crazy, fun things. Then anything that's left, I give away because I think hoarding wealth is a virus. I think it can train you to do the wrong things and focus on the wrong things.

Then I thought, okay, I need a new purpose. My purpose used to be to establish economic security so I could take care of my mom, have fun, be interesting, be important, find a mate, and take care of my kids. I thought, I need a new purpose in my life.

I really spent a lot of time thinking, what is my purpose? I tried to establish a new purpose other than just being really rich and a baller, which had been my purpose up until the age of, call it, 45 to 48.

But what you're going through, it sounds to me like you've been very successful. You professionally identify yourself, and when you get to your number, what I think is really helpful is to say, “Okay, money is the ink in my pen. It can write new chapters. It can make certain chapters burn brighter, but it's not my story.”

Really think about what is my story? No one's going to remember you in 3 generations, but in 1, what would you like them to say about you, right? What would you like, other than “he was really successful,” which it sounds like you are, what are the 2nd and 3rd things you would like them to say about you? I think it's a very healthy process to go through. I went through it, and it's given me—

What would you like the next generation to say about you if I were to turn that on you?

Well, I want to be known as a generous patriot and dad. I think about what are the 3 things you want on your tombstone. My purpose now is: I want to raise patriotic, loving men.

You know, I have 2 kids, 2 boys. Do you have kids?

No, I don't.

Once you have kids, everything kind of changes. That, for me, has given me purpose. It's given me a sense of, okay, that's why I'm here. I'm here to produce 2 men who are generous, loving, kind, patriotic young men.

9. The Truth About Kids and Career

That has given me a sense of purpose, and it's a nice grounding for me. I'm good at it. I don't think I'm great at it, but I know I'm good at it. It gives me a sense of comfort, such that I'm just not constantly thinking about how I get more AUM and go buy a company or something like that.

What would you say to me, who's scared about having kids while maintaining top performance at work? My brother has a child. It's knackering. They cry at night. You have to give them time, emotion, and love. I can just be ruthlessly selfish right now. To what extent do kids impact performance?

How old are you?

29.

I see you, kid. So, look, at the age of 29, with a little bit of money, living in a city, and being a good-looking guy, you're going to have a series of empty, meaningless experiences. But as far as empty, meaningless experiences go, they're going to be pretty good. So, I'm not sure you need to be in a hurry to get married.

What I would say to you, though, is that for most men, kids are motivating professionally because you realize it's no longer just about you and you need to think longer term. You need to be thoughtful. You need to maybe pull in your horns a little bit. If you hit it big, diversify a little bit. You start finding reward in different things.

Reward in raising kids with a competent partner is really rewarding. I wasn't in love with my kid when it came screaming out of my girlfriend. I thought the whole thing was gross and weird, and all I felt was fear that I wasn't making enough money. It wasn't like angels singing and bright lights everywhere.

But you fall in love with your kids, and then it gives you a sense of purpose. It was very motivating for me. I was making just enough money to go to St. Barts and date and give the perception of wealth and success. I wasn't motivated to do more than that because I didn't have kids.

Once I had kids, I'm like, “Okay, it's no longer about me. I've got to make a lot more money.” I found it very motivating.

Also, there's something comforting. I don't know if you're going through this, but when I was single and making good money, basically Thursday and Friday were about lining up fabulous experiences with fabulous people on Saturday and Sunday. It was like I was a monster or a dragon that could never be sad.

I wanted more money, more experiences, more incredible events, hotter women, more sex, more events, hotter women, more interesting events. More money was never enough. It was like, “I want more. I want fucking more.”

Having kids, for me—and I didn't want kids—I was forced to have kids because my partner basically said, “I'm out of here unless we're having kids.” But now I do have moments where my boys barge into the room and we're watching some show or football, and they throw their legs over mine naturally, sort of instinctively, and the dogs roll in.

That's like the only time in my life I've ever thought, okay, this is it. This is enough. I can't imagine nicer kids.

What I would tell you, and I think there's research here, is that if you have economic security and you can find a competent partner, having kids is incredibly rewarding—it's the most rewarding thing I've ever done by a long shot. And I didn't want kids.

Also professionally, I found it very motivating. So, the notion that somehow it's going to slow you down—no, I think my guess is, and I don't know you, but my guess is that's bullshit, to excuse the fact that you're still in an arrested adolescent stage, having a lot of fun. Have at it.

But what’s challenging there is, how do you know when you’ve found the right person? No one is ever going to tick all of the boxes. How do you know when to settle with compromise versus look for perfection?

Oh, I don’t know. I think everyone’s different, but for me, it was being 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: “Okay, if you don’t want kids, I get it, but I need to move on because I want to have kids.” So I was willing to reconfigure my life because the idea of not having that person in my life was really upsetting to me.

That either happens or it doesn’t. The hard part is, as you get older, you become more set in your ways. But I would imagine what happens to the majority of us will happen to you, and that is you’ll meet someone and decide that the sacrifices are worth maintaining that person in your life.

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. Then I think what happens a lot is your partner’s not up for that and basically says, “Okay, it’s decision time.” You make that decision, and hopefully you look back and think, “That was a good idea. That was the right decision.”

10. Are Billionaires Happy?

How many of your extremely successful billionaire friends have great family lives? I asked my mother on a walk the other day. She said to me, “What gets worse with money?” And I said, “The only thing I can think of is family.”

I don’t know. Actually, the majority of really wealthy people I know—I think there’s a bit of a cartoon that wealthy people are clawed over, in the sort of Bernie Sanders sense. I don’t know how much you know about American politics.

Sure.

There’s Bernie Sanders and Elizabeth Warren, that all billionaires crawled over people to get there. I have generally found the wealthiest people I know—I probably know maybe a dozen billionaires—are generally really good people.

The key to being a billionaire is establishing allies along the way. People put them in a room of opportunity even when they’re not in that room because they’re really high-character, good people. So I think the cartoon of Mr. Burns starting the nuclear power plant and being a weirdo and mean—I don’t find that’s true.

I find that the majority of really wealthy people I know, generally speaking, especially ones who are self-made, are high-character people. Now, they’re aggressive and can be brash or whatever, but generally, I find they’re high-character people and also pretty good family men. Sometimes they’ve been married more than once, but generally speaking, they’re good family people.

I don’t know if it’s proximity bias. I got lucky with some of the people I know, but I have found that the unhappy billionaire who has a shitty relationship with his kids and has been married 5 times—I find that’s mostly a cartoon. There’s so much anxiety injected into relationships when you don’t have enough money. Those are the people that have really dysfunctional families.

11. Becoming a Better Son, Father, Partner

My experience has been that, actually, wealthy people are generally both high-character and generally speaking have pretty good partnerships and pretty healthy families.

Have you ever felt as a father like you didn’t meet the grade? There was a period where you didn’t perform like you should have and you let them down as a father?

Oh, I feel that almost every day. The 2 people who make me more insecure than anyone in my life are my boys. Every day I wonder, “Do my boys like me?”

Then what you recognize in a moment of clarity as a dad is that they’re not necessarily supposed to like you. You’re not supposed to be their friend. You’re supposed to be their dad.

I handle situations incorrectly. I overparent. I underparent. I know I’m a good dad, but I aspire to be a great dad, and I still don’t think I’m there yet. It is something I have not figured out. I’m hugely insecure around my fathering. It’s something I struggle with.

I have a kid who’s applying to college. He’s taking the ACT. I don’t know how to thread the needle between telling him it’s go time—success is about knowing when to turn on the jets, and this is that time—and at the same time not putting too much pressure on a 17-year-old who is already studying all these subjects, trying to make the football team, get his IB scores up, get home on time.

I struggle. The position I find most rewarding, but also the people I’m most insecure around in a weird way, are my sons. So I think I just decided that’s part of it. Maybe there are some dads who just think, “Oh, yeah, I’m a great dad. No doubt about it.” But I struggle with what it means to be a good dad and how to manage it.

Did you have a good relationship with your father?

This is very interesting cheap therapy. No, I mean, my dad was fairly absent. My dad left us.

My dad was handsome, with a strong jawline and a Scottish accent, which meant in ’70s Southern California he could not only think with his dick, he could listen to it. He’s been married and divorced 4 times, and as far as we know, he’s on his 5th wife, which is a woman I basically pay to be his kind of home health aide.

He basically started his 3rd marriage while he was still married to my mom, left, and moved to Ohio. It was a different age. It was the ’70s. Kids were sort of like furniture. We didn’t revolve our lives around kids back then, so I saw him on holidays and summers. He wasn’t very involved in my life.

Where I have forgiven my dad—and I’ll put the question back to you about your relationship with your father—was a big unlock for me. I think we have an evolutionary obligation to just be a better dad than our dad was to us.

My dad was physically abused by his alcoholic father. When I recognized how his father treated him, I realized he was actually very good to me. That means he checked a box.

The biggest unlock—I used to resent my father and have trouble sometimes being nice to him—was recognizing: try and imagine what kind of son you want to be. Imagine what kind of friend you want to be. Imagine what kind of boss you want to be. Imagine what kind of romantic partner you want to be, and live up to that standard, as opposed to doing what I did all the time.

I managed my relationships like transactions, where if I wasn’t getting as much back for my emotional dollar, I no longer continued to patronize that establishment. There’s a problem with that because you’ll always inflate your contribution to the relationship and minimize theirs.

I found it much easier to say, “What kind of son do I want to be? I want to be a generous, loving son who’s really good to my dad.” The moment I just said, “That’s my benchmark,” rather than trying to measure, “Am I a better son than he was a dad to me? Could he have been better? Am I angry?” I found that to be such an incredible unlock.

So you’re willing to still be giving, even if it’s not necessarily deserved?

Yeah, because I feel like that’s the whole fucking point. That’s the shooting match. You want to die—ideally, I was a better son than my dad was to me. I was a wonderful husband. I was so wonderful to my kids. I got a lot of joy back from them. But on a balanced scorecard, I’m still in the net positive.

I think that’s the whole point: to leave—

You don’t agree with cutting people out of your life who are negative energies, who are negative forces?

Oh, sure. Don’t be—I shed friends all the time. I shed relationships.

What I used to be focused on was business. You’re—it sounds like you’re in finance. It gets pretty brutal sometimes. I’ve been, in my opinion, not abused but treated poorly by business partners and venture capitalists, and I struggle with anger.

I thought, “I’m going to serve this guy a cold lunch someday,” and it rents space in my head. One of my mentors, Hamid Moghadam, said to me, “You really want to get at this guy?” He was one of the most powerful VCs in the world. He washed me out of my stake in my company and kicked me off the board.

He said, “You really want to get back at him?”

I said, “Yeah. What are we going to do?”

He said, “Lead a fucking amazing life. That is the best revenge.”

If I have a bad business partnership, something I’m proud of is that I have never sued or been sued by anybody. If I have a bad relationship with someone or feel like I’ve been wronged, 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’ve never tolerated an abusive relationship romantically. But generally, with your important relationships, I think a healthy way to approach it is to say, “I’m going to put away the scorecard, and I’m going to focus on this aspiration of the kind of person I want to be in this relationship,” and hold yourself to that.

Can I ask, how did your relationship with your father change how you are as a father? Are your parents still together?

No.

Do you have a good relationship with your mother?

Amazing.

Do you feel that some of that is because, when your mom and dad broke up, you held—

What I did was, I saw—I sanctified my mom. My mom took care of me and died early, so in my mind she was this saint. My dad was that guy off banging a stewardess from Continental Airlines who didn’t show up for my soccer games and abandoned me.

That's how I saw it. The reality is, it wasn't that black and white. My mom, to a certain extent, unwittingly maybe turned me against my father a little bit unfairly. As I've gotten older, I've realized that nothing is black and white and that people aren't perfect.

But you are in a situation now where you just have to decide where you would get the most reward in terms of your relationship with your father. An amazing relationship with your mother goes a long way. I had an amazing relationship with my mother. I'm convinced that when someone tells you you're wonderful and loves you every day—and I trust and hope your mom did this for you—you begin to believe it. That's what my mom gave me.

In terms of the takeaway from my dad and what I've decided to do, I just try to spend a lot of time with my kids. I don't believe in quality time. I think that's a concept invented by wealthy people with no time who don't want to spend that much time with their kids and pretend they're good dads. I find the most important time with your kids—and you have some time to figure this out—is what I call garbage time.

The really amazing moments with your kids happen unpredictably. You're driving them to school, and they're not looking at you, and they're like, “Dad, I like this girl.” And you're like, “Okay.” You don't say anything because those moments don't come very often. You just let them talk, and you don't look at them for fear you're going to intimidate them, and you have one of those nice moments with your son. The only way you get to those moments is by spending a lot of time with them, because they just happen totally randomly.

The thing that really was rough for me with my father is that my dad just wasn't around a lot. So I just want to be there every day at 9:00 p.m. Greenwich Mean Time, no matter where my kids are. One of my kids is at a tennis camp in Florida, and one is at boarding school. At 9:00 p.m., I call my oldest; at 9:15, I call my youngest. A lot of times they block my call or they're unavailable.

But I know when they're older, they're going to be like, “Yeah, Dad was self-absorbed and into his own thing and flew off the handle sometimes, but he called me every day. He called me every day, no matter what.” What I would say is, take from your father the things that upset you and try to correct those for the next generation. Try to compensate and make sure that you don't fall into that same trap.

Did you find that money changed the relationships around you?

My father's 95 and not doing well. I can say this because he's like a baby now. He has no cognitive ability; he's not there any longer. My dad loves me more than my sister because I have more money than her.

My dad was raised in Depression-era Scotland and was so obsessed with money because if you lived in Glasgow in the '30s and '40s, you could starve if you didn't have money. He had some very weird things happen to him. He was in the Navy for 2 years and sent his money home because he got his money stolen in his first 2 weeks on a ship. He sent all of his money home to his mother, came home, and his mom had spent it on whiskey and cigarettes. My dad just had a very unhealthy relationship with money, and it scarred him.

It scarred me because my dad was that guy who would be in town for the weekend and take me and my friend to see a movie, and then he'd ask my friend for $2 at the end of the movie to pay him back for the ticket. The closest my father ever came to physical violence was when we went to a hotel. I'd never seen anything called a minibar before, and I decided that I should eat and drink everything in the minibar. So he had a very unhealthy relationship with money.

The reason he came to be really impressed with me was that I made a lot of money. That's fine; I just recognize it for what it is. For the most part, it's been a really nice thing in my relationships. It helped me take care of my mom, which was one of my objectives. Probably the most rewarding thing about making some money was that I was able to take care of my mom toward the end.

It removes stress from your life in terms of your kids and your partner. So on the whole, it's been a really wonderful thing for me. I enjoy it and feel like I'm good at it. You don't feel that way?

I do, but I do feel that people treat me differently now than they used to. People don't argue with me as much. People stop talking when I talk. When it comes to family decisions, my voice matters much more than anyone else's.

Why?

Because I'll pay for it.

Yeah. But the fact that you're self-aware enough to know that is important.

I'm on constant editorial calls, and the majority of my team is 24 or 25. Someone will disagree with me or say something rude, and I'm like, “I'm going to fire that shit.” I get angry because I have such a big ego. Then what I realized with just a few minutes of reflection is that it's really important to keep those people around you, because you can start to believe your own press.

And that's also one of the wonderful things about kids.

Your kids are not impressed by your professional success at all. As a matter of fact, they're totally unimpressed with you. Like, “Dad is lame.”

I'm literally the uncoolest person in the world in their eyes.

But I definitely agree with you. Once you have money, people laugh at your jokes, people find you interesting, and people want to know you, and it can lead to bad places. I've found, as I've gotten older, that 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. 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 asking me questions and wanting to know more about me just because I have money.”

Maintaining and finding people and a practice that keeps you somewhat humble and grounded is really important. But even the fact that you recognize that means you're well ahead of where I was at your age.

12. Behind the Persona: Who Scott Galloway Really Is

Can I ask, do you feel like the public snippets, the media, the TikToks and Reels that go around of you are a representation of who you are, Scott? Just being transparent, I loved your content coming into this, which is why I wanted to do this show, but the person I'm interviewing now is completely different, in an incredible way, from the image I had of you. Do you feel like the image isn't aligned with who you are?

No, it's an aspect of me. I'm an introvert. I'm happiest after an edible at night, alone with my dogs, knowing my kids are safe, writing, and just being alone.

When people meet me, they're generally disappointed. They think I'm going to be some fascinating guy full of interesting data interspersed with dick jokes. I'm an introvert. I'm fairly intense. That side of me is a reflection, a personality, or a side of my personality, but it's not me.

Social algorithms just love moments where you're making a puncturing statement or someone's calling you out. But no, I don't think anybody who knows me—I don't know if you feel this way—would say, “Oh, yeah, that's who that person is.” I try to be authentic. I try not to put on an act, but there's no doubt about it: when the cameras go on and it's showtime, it's showtime.

My favorite thing is to be around my kids and not say a word, just listen to them and be in the company of people. My partner consistently has to ask—or encourage—me. It's like, “Make conversation, for God's sake. You're so fucking boring.” I enjoy it. I'm paid to be an extrovert. I don't know if you feel this way, but I'm paid to be an extrovert. How I relax is, I just like to listen to other people and be an observer as opposed to a participant.

I'm paid to be an extrovert, too. Can you help me out, Scott? I've so enjoyed this. All my relationships say, “I've had enough of Brand Harry. The show's not on now. The lights are off. You can turn off the facade.” I've actually, in many ways, lost who I am because I'm always on show. I've just become the on-show version. Even when I'm at home on the sofa, there'll be a show.

Yeah, I never found that hard. You're at a stage in your life; you're so young, and you strike me as so self-aware that you're well ahead of where other people are. Just the fact that you're asking yourself these questions is important. I also think you're being a little bit hard on yourself. You've been very successful. You're in good shape, you're smart enough, and you're self-aware enough to ask yourself these questions.

The only advice I would give to a guy your age is that I did not engage. I wasn't very kind. All my energy, all my focus was on becoming more awesome and rich, not thinking, “Well, I'm in a unique opportunity to accelerate people's careers. I'm in a unique opportunity to pay people a lot of money to overcompensate them. I'm in a unique opportunity where young people admire me because I'm the head of this company.”

I have a unique opportunity that, when they do a good job, I can reward them, make them feel great about themselves, and just make their day. You're an impressive guy. You have people who work for you. It's such an incredible opportunity to just make people feel great all the time. Instead of paying someone £100,000, pay them £140,000. That makes such a difference in the world.

I wish I'd taken more advantage of the human capital I possessed to improve people's lives. Everything was about fucking me. I feel as if I just wasted so much opportunity.

What would you have done differently?

Just give more. I would have been kinder. When someone did a good piece of work, I should have called them out publicly. I wasn't bad; I was never mean. But you don't know how much power you have to improve people's lives when you have some success, right?

Tip them $100. Give some money away. Tell people you love them. Call your friends when they do something cool and tell them how impressive they are. Men have a tough time doing that with other men. If you're in a good relationship, tell someone how much they mean to you.

13. Marriage vs. Ambition: What Actually Keeps Love Alive?

Can I ask one final thing before we do a quick-fire? We haven't talked about marriage. When you think about sustaining a marriage through wealth creation, through kids, through kids going to boarding school, what have been your biggest lessons on what it takes to sustain a truly loving marriage through very different cycles of life?

It goes back to that first thing. First thing is, put away the scorecard. Say, “What kind of husband do I want to be?” Write it out: “What kind of husband do I want to be?” Then live up to that standard instead of saying, “Your parents were in town and you weren't very nice to my parents, so I'm not going to be nice to yours.” Just decide what kind of husband you want to be. Don't keep score. Decide, “I want to be a wonderful husband. What does that mean?” and live up to that standard.

Notice their lives. You're so successful that you're going to get used to everyone applauding for you. You need to take time to figure out a way for your partner to have stages where strangers and other people are applauding for her. Really go out of your way to give her venues, arenas, and environments where strangers can applaud for her, so it's not always about your success and you all the time.

Always express physical affection and sexual desire. It says, “I choose you.” I think women want to be wanted. I think that's so important in a relationship. Whenever you're feeling affectionate, whenever you want to hold their hand, whenever you want to do more, whenever you want to have sex, express that hunger, express that love, express that affection. I think it's really important in a relationship.

Then try to take time to appreciate and articulate what you've built together and really appreciate one another. I think the reason we get together is not to create more economic security or make children. I think it's so that we have someone to witness our lives, to notice our lives.

I've been married before, and I think one of the reasons I wasn't a great husband the first time around is that I didn't witness her life. I didn't notice her life. Whenever she was upset about something, I just wanted to manage my way out of it because I didn't want to deal with it, as opposed to really listening, witnessing, and noticing what was going on in her life, celebrating her victories, and just taking notes. I was in a hall of mirrors. I looked outside the window and saw myself.

Not keeping score, expressing physical desire, recognizing what you've built together, and witnessing their life. Those are the things.

This is so personal, so please forgive me. Have you found a stage of marriage harder than others? Be it kids going to boarding school, changing countries, refinding a chapter of yourself, or becoming parents?

Oh, there's a lot. The first time I realized I wasn't going to be able to have sex with other women, that was a real bummer. I missed that a lot.

Do you tell her that?

Oh, yeah. I think she feels the same way.

Young kids are hard. Little kids are hard. Very stressful, especially if you're both working. Really stressful. I barely even remember those 2 or 3 years, but I remember them being really stressful because my partner was working at Goldman Sachs and I was starting a business. It was a lot. She was up at 5:30 in the morning with 2 babies, and I was trying to build a business. That was really hard.

Do you agree? Never go to bed angry?

Yeah. I have a practice with my partner that I get into bed no matter what time it is. I stay up late and, although it sounds very Hallmark, I spoon her. So, yeah, we don't go to bed angry.

My partner is so vocal and willing to tell me everything that's not ideal that it's almost impossible for things to go unsaid. Things very rarely go unsaid. I would just say, try to be more emotive. Tell people what you're thinking and if you're upset, and be generous and listen to them.

Everyone has their own dynamic. I don't know. Northern Europeans just walk around morose all the time, and it seems to work for them. I think a lot of it is situational, but more than that, I'll go back to one of the things: I think it's so important to articulate how fortunate you are and what you've built together.

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?” She will say to me, “I'm really happy right now,” and that makes me feel really good because I see it as a reflection of my competence as a man that she's really happy.

But all of this is situational. It's the biggest decision you'll make. It's not where you work or where you live. The biggest decision you make is who you decide to have kids with, because you're in that person's life whether you want to or not for 25 years. It's a really important decision.

I have a lot of very successful friends who have a really lovely spouse but not a real partner, and their life is full of unnecessary anxiety. Then I have friends who aren't that successful professionally but have a real partner, and everything burns just a little bit brighter. It's hands down the most important decision you'll make.

For a young man like you, all you want to do is be out a lot and meet as many people as possible, but also give things a chance and see where they go. People would pray for your problems. Everyone who hears you talk about your problems is going to say, “I would kill for those problems.” I'm not exaggerating.

I'm embarrassed. You're the first person I told about this. I've been in a funk for the last 72 hours because there was a hugely successful IPO a few weeks ago, and I had a chance to invest. I got the CEO texting me that I was going to get an allocation in the IPO, and I was just too fucking lazy to follow up. This was a monster IPO, and all I can think about is the fact that I'm so angry and upset.

I'm embarrassed because why do I need more money? I don't need more money, but I'm still so fucking angry at myself that I missed this opportunity.

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

It's hard to get off the hamster wheel of identifying your self-esteem and your worth with money. Also, I would love a bunch more money to give away. 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 who we're willing to forgive: a guy who disowns his children on podcasts, is being sued by 2 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. In a capitalist society, every signal is telling you there's never enough. I think it's a natural, or at least understandable, instinct.

Is there anything you would do differently if you had a billion dollars? What would you do differently?

I would give a lot more money away. I'm sincere. Anything above my number now, I give away at the end of the year. It makes me feel important, and I don't do it out of ethics or virtue. I do it because it makes me feel important.

Will you give your money to your children? Do you believe in inheritance?

Yeah, I'll give them some money. I'll give them enough money so they can always have a house and always afford education. I'll give them a start, but they won't inherit—I won't give them a ton of money. I don't know what that number is, but I'll give them enough money.

I love what Warren Buffett said: “I'll give them enough so that they can do anything, but not enough so they can do nothing.” I'll give them enough money so they always know they can afford a home and afford their kids' education, which is a lot of money, but I'm not interested in building a dynasty or anything like that.

I know a lot of rich kids. They're not any less happy than other kids, but they're not any happier. I know a lot of rich kids in London, and they are much less happy. There's no reason to get up. They put most of it up their nose, and there's no passion. “I can get the Ferrari. I can get the Lamborghini. Why would I bother doing the work to get it?”

The joy is in the work.

Well, yeah. It's funny. It's not having money that's great; it was getting it that was really rewarding, right?

Yeah. Did you grow up with money?

No. So, you know what it's like. It's just so rewarding.

I didn't either. It's so rewarding now to spend money that you made and have some success. That's just such—

But I had this anger at society. I saw our family home get taken away, and I had this ruthless desire for revenge against what I thought was a brutal and unfair system for taking my family home.

Yeah, but those fires and that anger. So you were talking about rich kids.

If my dad had been rich and I knew I was going to have money, the only 2 things I know I would have in my life would be a Range Rover and a cocaine habit. I'm not self-motivated. I'm a fundamentally lazy person. Not having money, growing up in America, just seeing how important it was, and also feeling humiliation around not being able to take care of my mom when she got very sick, and having that amount of stress in a capitalist society in the US where you're underinsured—if you don't have money, it's really difficult to deal with real illness—that was really, really motivating for me. And I think probably the same disappointment and anger.

Those are embers that have burned and motivated and probably been, net-net, a positive for you. It sounds like you channeled those things into very productive ambition. Now take the gratitude and try and extinguish that anger.

14. Quick-Fire Round

Can we do a quick-fire round? I've so enjoyed this. I'm going to say a short statement, and you give me your immediate thoughts.

Sure.

What 1 belief do you have that most people think would be insane?

Well, on a practical level, young people need to drink more. I get a lot of pushback from that. But my source of power that most people don't engage in is that I'm an atheist. I'm 100% convinced that at some point I'm going to look into my kids' eyes and know our relationship is coming to an end. But it's hugely empowering for me. I worry about what everyone thinks, worry about being shamed, worry about being embarrassed, but it doesn't matter: they're going to be dead soon, and so am I. So my atheism is this incredible source of courage and comfort that I think a lot of people don't have the joy of participating in.

How does knowing that you'll be dead soon, and your atheism, change how you act on a daily basis?

Most people don't start companies because they're worried about public failure. Most people don't approach a strange woman much hotter than them because they're worried about embarrassment. Most people don't ask for $30 million for their VC fund because they don't think they're qualified or they're worried about public embarrassment. Most people don't tell other people they love them because they're worried about it not being reciprocated.

We're all going to be dead. It doesn't matter. Why wouldn't you take all sorts of risks, even if they have a very outside shot of paying off? Why would you be scared? Why would you care what the downside is? As long as you don't hurt people, as long as you're not taking stupid risks, if you want to score above your weight class economically and romantically, get out a big spoon, get ready to eat shit, and endure rejection.

If you ask someone for money or a job and you don't get the money or the job, or you ask someone out on a date and you don't get the date, you're all going to be just fine. You're all going to end up dead. But the person who is unafraid and asks for all of those things every day ends up wealthier and with a higher-character mate than their peers.

What were you most afraid to ask for?

I've always had a certain level of impostor syndrome. I didn't think I was going to get into college, and I didn't. Then I got in, and I felt like I fooled them. Then I got into Morgan Stanley, and I felt like I fooled them. So I've always felt like an impostor, but I've always done it.

If you don't feel impostor syndrome, you're either arrogant or not reaching far enough. I'm consistently embarrassed to ask for stuff, but I never let it get in the way. I got past that pretty early.

One of the best things that happened for me was that I ran for sophomore, junior, and senior class president in high school and lost all 3 times. Based on my track record, I decided to run for student body president, where I lost. I asked 7 women to prom. All 7 said no. I think that has built a level—it didn't traumatize me; it built a level of calluses and scar tissue—where I'm just not afraid of rejection.

If I could teach my kids any skill, it would be, 1, to communicate, but, 2, to be able to endure rejection, to be able to mourn and move on.

What do you think is great communication?

The ability to make people feel something. The communication that resonates for me with people is when I write about putting my dog down, when I write about coming home from a long business trip and noticing that my kids had grown, and wondering, what's the point of all this success if I miss my kids' growth because I'm not home for 2 weeks?

Something that makes people feel something, where you talk about something in a very real, vulnerable way and it makes people feel something.

Completely agree with that. Okay, you mentioned your father earlier. What are your biggest lessons from your mother?

Unconditional love is everything. Giving simply—it was simple. My mom, I said this before: if you tell people you love them and that they have value every day, they can't help but at some point believe it. And that's what she gave to me.

Do you tell your boys you love them every day?

Every day.

What have you changed your mind on in the last 12 months?

I don't know. I can't think of anything. I'm very open to change, but I can't think of any 1 big thing where I've changed my view on it. I'm drinking less. I've always said I love alcohol, but I've just substantially reduced the amount of alcohol because I realized my 60-year-old liver isn't what it used to be. I can't think in the last 12 months of anything I've really changed my mind on.

I'm very passionate about being a good interviewer. I care deeply about telling people's stories and, bluntly, having a great experience. When you reflect back on the many interviews that you've done, what would you say to people who listen to you today and go, “Fuck, he was great”? What would you say, other than this, is the best reflection of you—in an interview, in a piece of writing, in an article? In your mind, what piece of content have you produced?

I struggle with happiness. I struggle with anger and depression. I wrote a book called The Algebra of Happiness. I read every book and study on happiness, and it's my least bestselling book. I think that's what I want my kids to read.

Scott, as I said, it wasn't the show I was quite expecting, but this was incredible. It's one of the reasons why I love what I do: doing shows like this. Thank you so much for doing this with me.

Thank you, and congratulations on all your success.