SPENCER: Robert, welcome.

ROBERT: It's a pleasure to be here.

SPENCER: Why do you think debate is so important?

ROBERT: It embodies a lot of the stoic values that I talk about in the book. It's the idea of open-mindedness, critical thinking, and a certain amount of humility about one's own views. It's a way of bringing into the public square what I call a contempt-free zone, where people can appreciate the nuances of complex issues. They can hear the other side with respect, privilege facts over emotions, and prioritize logic over ideology. So it seems to me to be a very important way of bringing something to the public square that's sorely missing right now.

SPENCER: Do you think there's been a decline in debate?

ROBERT: There's certainly been a decline in the level of public discourse. I think our political culture has gone in the wrong direction, in a world in which almost everything else has gone in the right direction.

SPENCER: It's fascinating to read essays by politicians and think, wow, could never imagine the politicians today writing these.

ROBERT: No, it's true. One of the books that I cite in Stoic Capitalist is Enlightenment Now by Steven Pinker, in which he documents the huge amount of progress that's been made in so many areas of human life. Then he sets up political culture as the one counterexample, which he describes as an irrationality magnet. In the book, I talk about some of the reasons I think our political culture has gotten so toxic and dysfunctional, which we can go into if you like.

SPENCER: Yeah, what are some of those reasons?

ROBERT: Ironically, a lot of them are well-intended. When I was a young man, political candidates were selected in quote, smoke-filled rooms, and those were rooms that had professional politicians picking candidates that they knew personally who were, by and large, reasonably well qualified for the offices that they were going to hold. The process was not democratic, it was not transparent, and that got substituted with direct primaries. What happened was the combination of direct primaries and gerrymandering meant that 90% of all congressional seats were safe for one party or another. The only election that matters is the primary, and the only people who show up at the primaries are the most liberal Democrats and the most conservative Republicans. It's kind of pulled the political culture to the extremes and left the center politically homeless. That's just one example. Another example might be campaign finance reform. Again, it sounds benign, but if you're going to raise 100 million dollars to run for the Senate in a decent-sized state, and you've got to do it in $2,900 increments, the only way to get people to write checks is to fuel their anger. You get them afraid they're going to lose their gun rights or afraid they're going to lose their abortion rights; they'll write a check. If you campaign on the basis of believing in sensible compromise as a way of getting things done, nobody writes a check for that. Another one is what's gone on in network television. When I was a kid, there were only three networks. You would think 30 or 40 is a better situation, but when there were only three, their motivation, if you owned one of them, was to build as wide a tent as possible and alienate as few people as possible. Today, the motivation is to create a tight emotional bond with a narrow group of listeners or viewers. Fox did that better than anybody and is the most profitable network as a result. Those are just some examples of things that sound good on the face of them but, in the end, wound up hurting our political culture. Another very important factor is social media. People get their news largely through social media. They're basically living in a filter bubble where the algorithms that direct things to you only reinforce your current set of beliefs. They're not challenging your belief system. They're not making you confront any inconvenient facts.

SPENCER: On the example of campaign finance reform, there are significant drawbacks in either direction. As you point out, if you have lots of small dollar donations, that may create weird incentives to push, to get people afraid and make them hate the other side. On the other hand, if you accept really large checks, it may not be a very democratic process. It represents what wealthy people want rather than what people in general want. How do you think about that balance?

ROBERT: There are definitely advantages to campaign finance reform, although I would say that corporate money in politics has tended to be very bipartisan. Union money, on the other hand, has all gone to the Democrats. I think it's simply a more nuanced question and a worthy subject for open debate.

SPENCER: Yeah, so let's talk about Open to Debate. Can you tell us what it is and why you created it?

ROBERT: Open to Debate has become the kind of gold standard of debate in this country, and I created it because I was involved in a number of center-right think tanks. I felt that they were doing good work but basically preaching to the choir. I felt that political discourse in America had gotten kind of angry and dysfunctional. People weren't listening to each other, and I thought debate was a way of bringing something to the public square that would encourage people to engage with the other side, to listen to a different point of view than their own, maybe to be persuaded, but maybe just to emerge with greater respect. That seemed like a very worthwhile thing to do. I also had, from childhood or at least early adulthood, the idea of philanthropy, not so much as giving back, but as using the talents you have to create the institutions that you feel society needs. This one seemed manageable to me, something I could afford to do. I thought it needed doing, and so I ran with that ball 20 years ago. We were really right on so many things 20 years ago. Our very first debate was, we can tolerate a nuclear Iran, relevant today. 20 years ago, we said Russia is becoming our enemy, again relevant today. We We held a debate on Hamas — specifically, whether an elected Hamas is still a terrorist organization. So that was 20 years ago, and we were really ahead of the news cycle in terms of anticipating what are important issues, what are the issues worth debating.

SPENCER: And the format is that you have one person on each side, usually, and then the audience votes based on what side they start on. At the end, you can see which side they change to. Is that right?

ROBERT: That's certainly one of the formats we use. Sometimes it's two debaters versus two, sometimes one-on-one, sometimes a little more formal Oxford Union style, sometimes a little less, but basically the common element is that both sides are presented, and that voting, particularly in the live events, was great because it gave people in the audience a sense of really participating, and it gave the panelists a sense of wanting to get people to change their minds. The statistics were amazing. We had, generally around 30% of people who came with an opinion change their minds. I would walk around the audience at the end and ask people if they changed their vote. People who didn't would frequently say, "I voted the same way twice, but there were facts that I had never considered before, or moral sentiments on the other side that I had never considered before." I thought that was really a triumph.

SPENCER: That's great. I imagine there's some selection of the sort of people that come to watch the debates; they are more open-minded.

ROBERT: There's a self-selection process going on there, absolutely.

SPENCER: One thing that people sometimes say about debates is that they can fall into using persuasive tactics. If you're trying to convince others, then presenting a fully fact-based argument may not actually be the most convincing. What do you think about that?

ROBERT: I think that's generally true. If you present a lot of statistics, for example, you're not going to win a debate if you can frame an argument in a way that resonates emotionally with the listener; that's much more effective. I'll give you one anecdote. I think this was one of the most effective summations in all the debates we've done, which is hundreds. The resolution was "To prohibit genetically engineered babies." You can sort of imagine the public reaction would be in favor of that resolution. People are scared of science. They think of Frankensteins running around, and the woman who was arguing in favor of genetically engineering summed up her argument by saying, "I care a lot about the way you people vote today because it's very personal to me. A good friend of mine had a rare form of cancer and would be unable to have normal children, and with genetic engineering, she was able to have normal babies." Then she said, "I have that same form of cancer, and when it comes time in my life to have babies, I'd like to have healthy ones."

SPENCER: That's powerful rhetoric.

ROBERT: Debate over.

SPENCER: Do you worry that debates can become more about rhetoric, or do you think for the most part, just through the selection of who the debaters are, you're able to focus more on evidence?

ROBERT: It goes both ways. There are debates that have been extremely angry. We did one recently, the resolution that Israel's actions in Gaza are justified. Both sides were really angry. They almost had to be physically separated by the moderator; it was very hard to keep order, so it was not a model of reasoned discourse, but at least people got to see the passions that animated the other side. The Jerusalem Post wanted every member of the Knesset to see that debate, to hear firsthand the intensity of Palestinian feelings about their actions.

SPENCER: Yeah, sometimes what I say to people is that even if they think the other side is completely wrong, understanding the other side can still be helpful because it can help you figure out how to get people over to your side. It can help you figure out how the other side is convincing their side. So I think even if someone's not persuaded that the other side has any chance of being right, I think there are still arguments in favor of listening to debates.

ROBERT: Oh, absolutely.

SPENCER: A format that I've explored on this show sometimes is trying to do a kind of un-debate, where the idea is that I bring on two people who strongly disagree, and they work together to try to figure out if they can agree on why they disagree, trying to find sort of the key roots of their disagreement. I'm curious what your thoughts are about that.

ROBERT: I kind of like that. I mean, we had actually thought about a format that sort of started out with, "What do you two guys agree on?" And then move into the areas of disagreement, but we usually start with the disagreement and then explore the reasons and the areas of common ground. I thought it would be interesting to experiment doing it the other way around.

SPENCER: One thing I find fascinating is that a lot of disagreements involve disagreeing simultaneously on many different axes. For example, they might have a disagreement about facts, like what's empirically true, but simultaneously disagree about values. So even if they agree on the facts, they still wouldn't agree because one group thinks this is more important, another group thinks this other thing is more important, and they can even disagree on sort of more subtle things, like, "What is the right way to reason from the set of facts to a conclusion?" There are times when scientists might be looking at the same set of facts and disagree on what to conclude from it.

ROBERT: Sure, no, that's absolutely right. But I think the point is that issues are contentious because they're complex, because they're nuanced. If they were simple, you wouldn't have these divisions, and people living in filter bubbles can think that the issues are much simpler than in fact they are. When you get into debate, at least you understand that there are facts pointing the other way. There is moral sentiment on the other side. You might not agree with it, but at least you're aware of its existence, and that the people on the other side are not just idiots, but that they have some facts. They have logic too, and there are nuances here that if you're living in a completely filter bubble, you're not going to be aware of.

SPENCER: One thing I like to do every once in a while is look at something in society that's believed that I really don't understand how people could believe it. I'll go watch the commentators who support that viewpoint. You know, just as a silly example: how do people believe in flat earth? How in the modern world could someone believe that? But it's interesting to go watch people promoting a flat earth and look at the way they're talking about it, and then you can begin to see, "Oh, I can kind of see how, if this was most of the content people consumed on this topic, that, yeah, it could be quite persuasive," because they often have things that sound very persuasive, even though there are subtle reasons why they're totally wrong.

ROBERT: I was exposed to an example yesterday. I went to an art exhibition by an artist named Trevor Paklund, who is absolutely fascinated by the secret world of espionage, spies, and that kind of thing. And it turns out that UFOs, which is in this kind of category of how can you believe in it, there have been actual deception operations that have created the appearance of UFOs. So there you go. And you wouldn't have thought about that, or at least I wouldn't have.

SPENCER: Yeah, and someone who is really savvy, who's promoting ufologist beliefs, could point to these examples and say, "Look, look how convincing this is." And there might be something to it. Interestingly, I just learned yesterday what might have been the origin of the conspiracy that President Obama was not born in the US. Because I always thought that was just kind of made up of whole cloth, but it turns out it was due to a printing error. There was an old book that talked about him, and it misprinted him as being born in Kenya. And so suddenly it makes so much more sense. But why do people believe this? Because you can actually find this book that said that.

ROBERT: Interesting. I hadn't heard that.

SPENCER: Yeah, I thought it just sort of completely came out of nowhere, but then you have to be like, "No, no. That was a printer error. That was a mistake."

ROBERT: That UFO was a misinformation operation.

SPENCER: Yeah, exactly. These things are often more complicated. Or, you take something like these really wild QAnon beliefs about these pedophilia rings and all this stuff, and then you're like, "Well, okay, Jeffrey Epstein was a pedophile on a massive scale." You're wrong about the pedophilia rings, but there are other pedophilia rings. So there's a lot of nuance there. At first, it sounds completely crazy, but then you can begin to see why someone could, if they watch the right news or the right YouTube commenters, begin to believe that.

ROBERT: Well, we usually will do debates only if we feel that there are pretty good arguments on both sides. We're not going to debate Flat Earth, but we will debate Israel and Gaza. We did a debate, actually, the one that was released just a couple of days ago was Alan Dershowitz debating on the subject of, "Did Harvard have it coming against Larry Summers?" So you had these two really Harvard stalwarts, and nobody was defending the Trump administration's actions, but the debate was really about whether Harvard made itself a target by doing things that were really inappropriate for Harvard to be doing.

SPENCER: Sometimes people wonder whether they should give voice to one side because they worry if they think one side is sort of more righteous or has better arguments. They're like, "Well, even by giving the other side airtime, they might be doing harm." How do you feel about that?

ROBERT: Well, I'm totally against it, yeah.

**SPENCER:**Why is that? Is it because you just think the value of hearing both sides is more valuable than trying to choose the side that you think is more righteous?

ROBERT: If it's a complicated issue and it's a contentious issue, your side is never 100%. There's always something on the other side. There are some facts, there is some logic, there are some moral sentiments, and to deny them, to silence them, is just putting your head in the sand. It's not constructive.

SPENCER: Yeah, I think that's a really powerful framing of what is the side you disagree with right about? Just having that question, because it's so easy to assume that they're right about nothing. We have all the logic, we have all the facts, we have all the good values, et cetera, and the other side has none of it. Probably that's not true. I mean, maybe every once in a while it's true, but it's pretty rare.

ROBERT: Well, certainly in the debates we've done, first of all, we have to think that there are good arguments on both sides, so we're not going to do the debate. But secondly, the audience, which, as you say, is self-selected, is relatively open-minded, but still to get 30% of people to change their minds. I mean, that's really saying something powerful about not only the format, but political culture, and at least there are some people out there who are really open-minded, and I think that that's right, and that's what you can build on.

SPENCER: It's interesting how, on some topics, it seems that people's beliefs are essentially unmovable. It's hard to imagine anything that would change their mind. On other topics, it seems people are much more evidence-focused, where they might have an opinion now, but if they see the right evidence, they're going to switch their view. I wonder if that ties more to things around identity. On a certain belief, they might have an opinion, but it's not so wrapped up in their identity that they're unwilling to budge.

ROBERT: That's interesting. We never did a debate on abortion, for example, because I felt it was an area that, well, it's very contentious. Nobody was going to change their minds on abortion. We did do a debate on the effects of the repeal of Roe v. Wade, because that's very factually oriented, and how that might have played out. In fact, it played out with practically no change in the number of abortions in the country pre- and post-Roe v. Wade decision.

SPENCER: Really? Why is that?

ROBERT: Well, because people substituted pills for abortion procedures. The states with the biggest populations continued to have abortions available. People will travel if they need to, so it really didn't have that much of an impact. I'm just giving that as an example of something that could be a fact-based debate, whereas the feelings about abortion are ones where nobody's going to change their minds. So, okay, we wouldn't have debated abortion, but we might have debated the impact of that.

SPENCER: One thing I find fascinating about the abortion debate is the right tends to frame it as abortion is murder, and the left tends to frame it as abortion has no negative consequences. Nothing is lost through abortion, even up until the day before a baby would be born. If you look at the sort of most American people, they're actually, interestingly enough, somewhere in the middle, where they think early abortion, the first two trimesters, is totally fine. But then they actually become pretty wary of it as you get closer to birth, where they start saying maybe it should not be allowed, or only allowed in special cases. It's interesting to me that there's a pretty common majority view that is sort of in the murky middle.

ROBERT: Yeah, exactly. The fact that that middle is so murky is itself interesting, because where do you draw the line, and why? Very few people would be in favor of what they call a partial-birth abortion. There are definitely people on the left who support that, but it's far from a majority view. It's complex and nuanced, like most contentious issues.

SPENCER: You mentioned earlier that you don't like the framing of this idea of giving back. Why don't you like that idea?

ROBERT: I don't like the idea of philanthropy framed as "giving back" because it implies that you got the means to be philanthropic by taking something away, by hollowing out, by doing a process. The implication is that you've got the means to be philanthropic by taking something away from society. My view is that if you built a successful business, the odds are very high that you contributed something to society. Maybe it's a better technological solution, maybe it's creating a better environment for your employees to flourish and be creative, maybe it's a better way of serving your customers, or maybe it's a better way of using limited resources. Building a successful business contributes to society. You don't owe anything back to me. I call one of the chapters in the book The Selfish Philanthropist. The idea really is that if you don't owe anything back, why be philanthropic? The answer to me is because it's an opportunity to exercise your talents, your abilities, your organizational skills, whatever, for the benefit of society and grow yourself in the process.

SPENCER: Why say selfish? Because unless you are unconcerned with the benefit you're causing to other people.

ROBERT: It's selfish in the sense that it's a perfectly legitimate question to say, "What is in this for me as a philanthropist?" and to say, "Okay, well, engaging in this process and this activity is going to be very satisfying for me, so I'll do it." Something else, maybe just writing a check passively. Not so satisfying.

SPENCER: So do you think that people should have an obligation to do altruism in addition to doing what's good for themselves?

ROBERT: I wouldn't say it's an obligation, because I don't subscribe to this idea of giving back that they owe something. On the other hand, I think the well-lived life, in my estimation, does include acting for the benefit of society. It does include using philanthropy as a broader way of exercising your own abilities, giving, taking, having a broader canvas to paint on with whatever creativity and abilities you can bring to bear.

SPENCER: As a billionaire, I imagine you're constantly inundated with people trying to get you to give to whatever cause they favor. Does that become frustrating, having everyone around you trying to get money from you?

ROBERT: Not really, because I operate by this principle: I really want my philanthropy to be in areas where I feel I can make a real contribution besides just writing a check. So Open to Debate is an example. Just a couple of weeks ago, the New York Times announced another philanthropic initiative of ours called Canyon, which is a new venue on the Lower East Side of Manhattan. It will be a place for video art, for artists who are using the moving image, integrating art and music, art and technology, and interactive technologies to create immersive experiences. These are all artists who are basically in museum collections and recognized as important artists, but I felt they needed an environment where people would take the time to engage with them. These take duration; they take time to engage with, and I felt you needed a custom-made institution to get people to engage with those art forms in the way that the artists intended. That's another example. The third major one for me is research on longevity, or more precisely, extending human health spans by understanding why we age in the first instance, what is going on at a molecular level in our cells that makes them, over time, become vulnerable to disease, that makes them less fit for purpose. Those three are all things that I felt were personal initiatives that I could get involved with, that I could direct, that I could lead, and that I can have a meaningful impact. That's how I'm concentrating my own philanthropic dollars.

SPENCER: I don't know if you've heard of the Effective Altruism movement before, but what do you think of the philosophy that comes from the Effective Altruism movement that says, "Yes, we're going to spend a bunch of our time and money doing things that are beneficial for ourselves, but when we're thinking altruistically, we should be thinking about what does the most good per unit dollar?" Good could be defined in different ways. Some people might define good in terms of reducing suffering, and so they want to say, "How do you reduce suffering as much as possible per unit dollar?" Or you might define good in alternative ways to that. But then basically it's taking an optimizing mindset.

ROBERT: It's fine. I think if that works for you, great, I have no argument against it as an individual choice. But I think there are other ways of looking at it. Yes, you can take a quantitative view of maybe the greatest good for the greatest number. But that would not have produced the Metropolitan Museum of Art. It would not have produced philanthropy at high culture. It might not have produced Harvard University or Yale. There are philanthropies that are more directed toward high culture, high intellectual achievements, high scientific achievements. There are others that are directed more at people who are suffering, as you say, and society needs both. I think the Effective Altruism movement is looking at one worthy thing, but it's not the only thing.

SPENCER: I think there are probably different opinions in the Effective Altruism community. But I think some would say something like, a museum of art, well, that's really nice. If you actually convert it into how many lives could be radically improved if you were to give that money to extremely poor people in Africa, for example, it doesn't stack up. It ultimately doesn't produce enough value in the world relative to what it could be used for.

ROBERT: You're the philanthropist. You make that decision. But I certainly wouldn't want to impose the Effective Altruism view on anybody else.

SPENCER: Yeah, I think it tends to, some people, resonate with them immediately, and other people, it doesn't resonate. I'm wondering if you feel like you have values that are bigger than yourself, for example, the value of truth-seeking. You could think of open debate as promoting the value of truth-seeking, which is something that's bigger than yourself. Do you feel that way with your philanthropy, that you're going after these values that are external to you, that are deeply important to you, or do you feel you kind of frame it differently?

ROBERT: I'd say in my own philanthropy, I think the values are consistent with my own. That's sort of part of the point, in a sense. I think the greatest gift that science could confer on human flourishing is extending our health spans, the period before we get the debilities of old age. That's absolutely consistent with my values, intellectual interests, and benefit to society. I don't see any particular conflict there. I think in Open to Debate, it's totally consistent with my values of privileging rationality and critical thought over emotional autopilot. I think philanthropy, in my case, is quite consistent with my values. I don't know why that's not a good universal principle.

SPENCER: That's kind of what I'm getting at. I think it's an alternative way. Effective altruists tend to think about it as a maximization principle. Get the most bang for the buck per dollar to minimize suffering or something like that. Another way to think about it is you've got a set of values that you care about deeply, and you're trying to create more of them in the world. Execute on those values. One principle in your book that comes up is this idea that the obstacle is the way. What does that mean?

ROBERT: It's a basic stoic idea that our actions can be impeded by obstacles, and the stoic is trying to look at those obstacles in a positive way. I give a few examples from my early childhood. I was in an extremely financially insecure situation where my parents were worried about paying electric bills or phone bills, and I was well aware of that. They were emotionally intense experiences when I was six or seven years old. The obstacle for me, in response to that, was taking full responsibility for my own life, realizing that I would have to figure out for myself how the world worked and how to make my way in it. An obstacle I faced early on was the burden of bad ideas. My mother was a communist, and she was very vocal about Marxist ideology at home. As a 10-year-old, I was hearing "from each according to his ability, to each according to his needs." I was thinking, "God, I'm able; I get good grades. Should I take my grade points and give them to some lazy kid? What sense does this make?" The obstacle is bad ideas, but the way is critical thinking. I had no role models at home or in the world I was occupying, or nothing that really seemed aspirational. The way for me became reading biographies, and I read them as how-to manuals: what is a well-lived life based on the lives of hundreds of people in different walks of life that I would read about. They only write biographies about pretty exceptional people, so that gave me a very interesting set of ideas about what my own aspirations might be. Those are some illustrations of the obstacle becoming the way.

SPENCER: Is it fair to describe that as the idea that when the world presents you with an obstacle, you can actually use it as a growth experience, and so the obstacle then becomes the thing that directs you to the next step?

ROBERT: Yes, exactly.

SPENCER: On the topic of communism, I'm curious, have you had an open debate about communism versus capitalism?

ROBERT: Yes, we've definitely done that. We've done debates on capitalism. It was not exactly communism versus capitalism, but I think one of the resolutions was two cheers for capitalism. So not three cheers, but that capitalism works okay.

SPENCER: Do you think that communism is completely devoid of value as a philosophy, or do you think it might get some elements right, but then it kind of puts them together in a way that leads to bad conclusions?

ROBERT: It's been tried and it hasn't worked. We've seen that generally economic freedom is associated with progress and human welfare. I think China is the greatest example in my lifetime. I still call it a communist country, but basically, they've really, I argue in the book, there's a chapter called Give China Face, and one of the arguments is that China is one of the least communist countries. If you measure communism by the share of GNP that the central government controls in China, that share is about 16%. In the US, it's 26%, in Britain, it's about 45%, and in France, it's 54%. So, my definition of communism might not be well-aligned with the reflexive view about what a communist country is, but I definitely feel that it's almost proven that economic freedom and the freedom of individuals to innovate, to build businesses, to act with economic freedom produces better outcomes than when things are centrally controlled by the government.

SPENCER: It's interesting to hear you say that, because when I went to China for a little while, just a couple of weeks, I was shocked at how capitalist it felt to me. I really expected it to not feel capitalist, but it was. In certain ways, it feels more capitalist than New York, just the vibe of it.

ROBERT: Oh, sure. If you drive around in taxis in China, I don't know if this is true now, but eight or 10 years ago, taxi drivers would have photographs of Jack Ma as a kind of hero figure in their cabs. I can't think of any taxi driver in New York that has a business leader as a hero.

SPENCER: The particular quote you mentioned, "from each according to his ability, to each according to his need," seems to me that that model might be useful in some circumstances. Imagine a family. The person who can provide is going to provide, and the person who has needs is going to get taken care of. To me, it seems like it actually becomes less and less tenable the bigger the group and the less incentive aligned the group is.

ROBERT: That makes sense. But even at a family level, it can get very tricky. I know families that, for example, might have an autistic child, and that's the neediest child, but how much of a sacrifice do the more able children have to suffer because of the attention given to the child with the greatest need? Even on a family level, it's not a no-brainer.

SPENCER: That's an interesting point. It also reminds me of the Rawlsian veil of ignorance idea where he said you should try to maximize the worst off, and that's sort of the approach to making a good society, which many people disagree with, but it kind of rhymes with that same idea.

ROBERT: Yeah. The book talks about Rawls a bit, but it also talks about Nozick. Rawls is talking about distributive justice. He asks how goods and services are distributed in society and what he thinks is the optimal way of doing that, whereas Nozick talks about the process. The question is not whether the outcome is fair, but whether the process is fair. If the process is a result of free exchange by free people, with no coercion, no force, and no misinformation, you just accept the results. We did a debate that really outlined this issue very nicely. The resolution was, "Taylor Swift deserves our billions." The philosophical idea there was that whatever Rawlsian distribution of resources you made, if people chose to give a couple of billion dollars for the pleasure of hearing her perform, what's wrong with that? She's better off, they're better off. They made free choices. Just because you wouldn't have given that particular person a couple of billion dollars in whatever Rawlsian framework you had, it's almost asking the wrong question. The Nozick question would be, was there anything wrong with the process by which she got her billions? The answer, at least in the debate, would have been no.

SPENCER: This seems to get at a core divide between the left and the right about how they view the effects of making money. People on the left are more prone to say, "Well, there are a lot of companies that make money in ways that are not beneficial to society. Some are even harmful to society. Sometimes it's indirect harms, like pollution or increasing global warming. Sometimes it's direct harms, like ripping off customers. Yet, some of the companies, while sometimes that's illegal and the companies get taken down, other companies are able to skirt around the law; they're able to play the game where it's not technically illegal, but they do end up harming customers." On the right, people tend to view it as, "Look, if people are willing to give you their money, then you're probably benefiting them. Why would they give you their money otherwise? As long as it's truly a free exchange, as long as you're not lying, each transaction probably creates good in the world." It sounds to me like you kind of tend to fall more on the right side of that divide, but what do you think of the left perspective on that?

ROBERT: I think you've framed it well. The reason we picked Taylor Swift as the subject of that debate was precisely because there's almost nothing you could say against the way she made her billions. Nobody understands how hedge fund guys or private equity guys make their billions, so you can't really hold them as a model.

SPENCER: People don't know how to evaluate their behavior?

ROBERT: Yeah, nobody knows how they did it, or why they did it, or what benefit it gave them, so they're not good. That wouldn't have made a good debate. And as you say, people on the left approach corporate, there's a kind of anti-capitalist framing, almost where they will look for evidence that supports the idea that building a successful business has to be quasi-corrupt or taking advantage, or exploitative in some fashion, or whatever. And if you come at the world with a frame — and this, again, is a stoic principle — you will find evidence to support that frame, and you'll interpret and be ambivalent evidence again to support your framing and evidence that goes the other way you just disregard. So framing is a cognitive mistake, and I think it's a mistake that the stoics caution against. The idea is to distinguish between facts and interpretation. Try to look at the facts as coolly and as rationally as possible, and don't approach the world with a framed view and then try to only consider the facts that support that view.

SPENCER: It's intriguing, because most people see themselves as looking at things in an objective way. I 100% agree with you, but I also think a lot of people would be like, "Oh, that is what I'm doing," even if they're not.

ROBERT: Yeah, I think stoicism teaches humility and makes you more conscious of that framing — what I'd call a cognitive distortion. If you're privileging rationality, you should avoid approaching the world with preconceived frameworks and instead be open to evidence in all directions. So if you're privileging rationality, you really want to avoid a sort of preconceived framing of anything and be open to the evidence that points in all different directions.

SPENCER: As I started studying rationality and cognitive biases more when I was younger, I started thinking that I'm less and less rational, and I would suggest that that's actually the ideal thing to happen, because chances are, you are more irrational than you realize. As you start to study it, hopefully you'll start noticing the ways that you've been irrational and hadn't identified before. At least that's my thinking.

ROBERT: The last sentence in the chapter in the book dealing with being open to debate is one of the precepts I took away from this whole experience: beware of ideology, especially your own.

SPENCER: Yeah, absolutely. And that's the hardest by far. It reminds me of what Feynman said: the first thing is not to fool yourself, but you're the easiest person to fool. On the question of the Left-Right divide around companies, I'm curious to hear your reaction to how I think about it, which is that I think whether companies cause good or harm actually hinges to a significant extent on the quality of regulation and the enforcement of regulation. In an environment where laws are not effectively made, let's suppose it's totally legal to dump your sewage in the river and poison all the people in the village; some schmuck is going to come along and do that because they can make it more profitable to do so. Good regulation will say, "No, you can't dump your waste in the river. If you do, you're going to go to jail." And then, of course, that has to be enforced. I think of it as there are ways that companies can help and make money helping the world, ways that companies can make money that are kind of neutral for the world, and ways that companies can make money that harm the world. Good regulation tries to eliminate all the ways they can make money harming the world. Once you do that successfully, then companies become a force for good. I'm curious to hear your reaction.

ROBERT: I think the example you gave is completely unexceptional, because if a company imposes costs on society by polluting rivers or stuff like that and doesn't have to pay for that cost, that's simply a distortion. That's not the way markets are supposed to work, and that kind of regulation seems absolutely clear. If a company causes harm as part of its process, either they should be regulated so they can't do that, or if they do it, they've got to pay the people who are harmed.

SPENCER: Just on that point, really quickly, I think this is often a misunderstanding people have, where they think that economics says you should have a completely free market, but actually economics says that in cases like this, you need regulation. You need taxing to solve the distortion. I think that is what you're getting at.

ROBERT: In that situation, regulation is probably a good thing, but you could argue that it could work in an unregulated way if the people whose water was polluted would then sue that company and force them to pay the costs of the pollution or avoid polluting in the first place, because it's much less costly to do that than to pay for all those damages. There are different ways that you might get to that result, but the result you want is that a company has to pay for all of its inputs and pay for all of the costs of its operation. A trickier example to me would be social media companies. I really grappled with that one. I would have felt initially that a company like Facebook was a great thing for society. It made it much easier to form communities of common interest and helped people maintain social networks. It seemed like a very good thing at the beginning. I now feel like these companies are potentially damaging our civil society by setting up these filter bubbles in which they're operating like capitalists. They're operating in a valid way to give you what you want and give me what I want. It seems good to give you the news that's of interest to you and give me the news that's of interest to me, but the unintended consequences are that you're getting news that reinforces your pre-existing views, and I'm getting news that reinforces mine, leading to a very polarized society as a result. To me, you're getting into a very subtle and tricky area. It's not obvious what kind of regulation you would want, who would be the regulators, or who would have the expertise in government to regulate these complicated areas. These are tricky questions.

SPENCER: That's a good example. Another example I think about is multi-level marketing companies. I don't know how familiar you are with them, but I don't want to say that they're all the same, but quite a number of multi-level marketing companies convince people to become agents for them, who then sell their products on their behalf. Most of the compensation comes not from selling the product, but from convincing other people to also become agents. It ends up being a situation where you make the most money by convincing people to join, to convince people to join, to convince people to join, and they start looking very Ponzi scheme-esque. I think there's an argument to be made that although people are freely choosing to join, nobody's coercing them, many of the people involved end up harmed. In many cases, well over 90% of the people who join end up losing money. It's a tricky case because people are acting freely, yet they often end up worse off than they started. How do you think about a case like that?

ROBERT: I think a case like that is simply an information issue. Companies should be required to disclose the fact that 90% of the people who are selling this product wind up losing money doing it, and that has to be a disclosure item. The analogy would be like the disclosure around securities or disclosure around side effects of drugs. That seems like a basic disclosure requirement. Free people are making free decisions, but they're not making well-informed decisions. If there's an information asymmetry here to correct, that seems both capitalist and desirable.

SPENCER: Yeah, and I agree with that. But a fascinating thing is that many of these companies actually do release disclosures of how much people make, income disclosures, and the income disclosures are absolutely horrendous; they make the company look terrible. And yet the companies are so good at persuading, or their agents are really so good at persuading people, they continue to exist. So it goes back to critical thinking on some level.

ROBERT: It reminds me of a quote by Albert Einstein that I love. He said, "Human intelligence is limited. Human stupidity is not."

SPENCER: It's a tough one. Maybe where you and I disagree, if we disagree on this, what percentage of companies find a way to make money doing harm versus doing good? I think a lot of companies make money doing good or doing neutral stuff that's at least not harmful, but I do think a non-negligible fraction are making money doing harm, and that's something we should try to regulate out of existence, insofar as possible.

ROBERT: Definitely there are. I gave the Facebook example as one that I would regard as pretty tricky, pretty ambivalent as to whether a company like that is, on balance, doing good or harm. I'm interested in really big companies that are going to have significant social impacts. The kinds of Ponzi scheme things might be interesting examples to talk about, but they're not a big part of the economy. People are not becoming mega-rich building companies like that. People are getting richer because they are doing major innovations, like Google, Amazon, Facebook. These are the really big impacts — things I personally would like to focus on.

SPENCER: I'm curious if you've thought about the consequences of AI, and are you concerned about the consequences of AI? Are you more bullish on it?

ROBERT: I have to say I'm a resolute techno-optimist. I think AI is very likely to propel a huge increase in productivity. I sense it myself. I'm much more personally productive since I started to learn to use the various AI platforms. It's almost like I have a handful of PhD-level assistants researching and doing great, quick work on almost anything I'm interested in or anything I'm trying to accomplish. I'm very optimistic that AI and AI plus robotics are going to really spark a huge increase in productivity. But people tend to, and I've done enough debates on almost every technological innovation, the common reaction is techno-pessimism, and there's so much more public conversation about the risks than there is about the potential. The risks are real, but personally, I'm much more excited about the potential than I am concerned about the risks, and I think the prevailing view is the other way around.

SPENCER: It's interesting because there are many different risks that people worry about, things like job loss on one hand, or deep fakes, or bots being used to spread misinformation at a new scale, or automated hacking. You have so many of these different things, and you have these different constituent groups that worry about different aspects of it. Some people worry about losing their job. Some people worry about AI being uncontrollable and destroying civilization.

ROBERT: That's true. People tend to be, I think it's sort of wired into human nature to be more concerned about the risks and less persuaded by the upside. One of the points I make in the book is that stoic idea that change is inevitable, nothing is permanent. The people who create change are going to be on the right side of things. The people who adapt to change are going to do fine, but the people who resist change are not; that's not going to be helpful. It's not going to produce a good outcome.

SPENCER: Nick Bostrom has this interesting thought experiment. He imagines technology as though you're drawing balls from an urn. Some of the technology you draw, it's like society invents a new technology. We don't know what it's going to be like. Some of the balls drawn from the urn are white balls that he describes as beneficial technologies. They improve health care, et cetera. Some are gray balls where there are mixed effects, maybe social media is like this, where there are some good things and some bad things. It's complicated. But then he has this idea that some technologies might be black balls, where once you draw them from the urn, once you invent them, it sends society on a dangerous path or harms society. But you can't put them back in because now the technology is unleashed; it's very hard to get rid of it. His question is, what percentage of technologies are black balls, and how many can society afford to draw? Maybe we draw one black ball, and society is over. If we think of it this way, it makes it harder to be a techno-optimist because it might be that we're doing these experiments on society that nobody's planning. We're just kind of doing it because someone invented the technology.

ROBERT: Well, I think that's a terrible idea. I mean, it basically is an argument for freezing knowledge where it is now. It completely goes against human progress. It strikes me as an awful idea.

SPENCER: If you think about the risk to society, let's say there's a new technology that has a 1% chance of creating some devastating effect, like mass nuclear war. How do you think we should best handle cases like that?

ROBERT: Well, I think, again, you need rational decision-making. People do have a tendency to catastrophize, to think about absolutely the worst-case outcome and focus on that. That's simply not a rational way of deciding. Rational decision-making involves looking at costs, looking at benefits, weighing them against each other. You're not obsessing over a single unlikely case. I think it's a cognitive distortion to constantly catastrophize and think about how to mitigate the risk of the most unlikely case, as opposed to how to maximize the expected value of this innovation, of this activity.

SPENCER: I feel like it's complicated, because if it's too catastrophizing, where you're putting much more weight on something than it really deserves. I completely agree. But if you do an expected value calculation, if you've got one really, really big negative, even if it has a small probability, it can change the whole expected value calculation.

ROBERT: Well, the story I start out with in the book is a story where I risk the entirety of my liquid assets in a very leveraged way, in a transaction where, if we lost 20% of our money, I would be wiped out. I explained why I made that calculation, why it was something that very few people would do, but why it was the rational calculation, and I addressed this catastrophizing idea, because in this example, if I had thought that the worst case was that I'd end up homeless and living under a bridge, I wouldn't have done it. But by thinking, "Well, okay, if I lost 100% of my liquid assets, what situation would I be in?" Well, I would have learned something from the experience. Would I be able to recreate the kind of job I left to start the business? My family's not going to go hungry. It's not going to be horrible. By thinking realistically about the undesired outcome, it helps you get over your innate emotional response. The emotion in that case is fear, and what's going to happen if this doesn't work, and that fear is very natural, but I didn't act on fear. I acted on what I thought was a rational calculation of risks and rewards, and it stood me in very good stead. And that's the sort of opening story of the book.

SPENCER: In retrospect, what do you think the percent chance was that you would have gone bust?

ROBERT: I thought one in three. I thought there was one chance in three that I'd make 100x my money, and one chance

SPENCER: A good expected value, though, very scary.

ROBERT: Now that's the arrangement I made. Just to flesh it out, the story is, the normal deal at that time was for people doing what I was trying to do, which was the early days of leveraged buyouts. The guy doing the work would get 20% and wouldn't put up any money. So it was sort of heads, he wins, the investor loses. My investors didn't like that structure. They felt that it didn't align interests well, that I would be inclined to take excessive risk. I said, "You're right, it doesn't align interests well, and you want me to take more risk. I'm willing to do it. I'll put up 100% of my liquid assets on this basis. I want 50% of the profits, and I'll absorb 50% of the losses." They viewed that as a very courageous decision, but a decision that would completely get me focused on minimizing risk. It worked out extremely well for them. It worked out extremely well for me.

SPENCER: What multiple did you make on the investment?

ROBERT: Oh, dear. The first deal we did, we lost $100,000. Think about this. This was a long time ago. So these numbers, you sort of multiply by 10. I was risking $400,000, which was my liquid net worth at the time. I think it's maybe $4 million in today's purchasing power. The first deal we did, we lost $100,000. The second deal, we made $100 million, so it sort of averaged out.

SPENCER: Wow, that's wild. Before we wrap up, I thought it might be fun to do a rapid-fire round or ask you a bunch of difficult questions and just get your quick take. How do you feel about that?

ROBERT: Sure, whatever.

SPENCER: All right, cool. So, relevant to what we were just discussing, imagine your life was rerolled over and over again. Obviously, you've been tremendously successful. What percentage of the time do you think you would end up at the level of success you have now versus other levels, if the dice were rerolled over and over?

ROBERT: Well, luck definitely played a part. You don't know quite the road that's taken. You don't know what might have happened if you were unlucky. Samuel Butler has a quote that I always like, "As a man succeeds in life, he develops a deeper appreciation of his own abilities; as he fails, he develops a deeper appreciation of the role of luck in human affairs."

SPENCER: It's probably something to consider. What would you like to see debated more in society?

ROBERT: Everything.

SPENCER: That's a good answer. Is there any particular topic that stands out as something people aren't talking about that we should be?

ROBERT: I'm a free speech absolutist. I really feel like there should be no subjects that are off the table.

SPENCER: If any anecdote, we ran a study on intelligence recently, and one of the funny correlates of IQ is that higher IQ people were more willing to have people they hate be able to speak out and protest and debate, which I thought was fascinating. If you hate the Neo-Nazis, higher IQ people are more willing to allow the Neo-Nazis to speak and give debates.

ROBERT: I would feel that way.

SPENCER: If someone wants to watch one of the open debates. What do you think is a great debate to start on?

ROBERT: Well, probably the most contentious one, and the one that had the biggest audience, was the Gaza debate. Israel's actions in Gaza were justified. The most nuanced and almost least debated was the one that we just released on Harvard Had It Coming. Those would be two great ones to start.

SPENCER: What do you think is a critical thinking skill that most people don't learn?

ROBERT: I think most people don't learn critical thinking period. Probably the best discipline is this idea of really trying to very consciously separate facts from interpretation. I think that's the starting point: to simply look at the facts with no interpretation whatsoever, and then layer in interpretations, but realize that those interpretations are flawed. Have some humility about your interpretations, but start with simply the facts.

SPENCER: Yeah, it's so interesting how we all have stories we tell, but we don't treat them as stories. We don't see them as stories. We just see them as the way reality is, right?

ROBERT: Yeah.

SPENCER: What's your perspective on how to use your time? You could be doing so many things with your time. How do you prioritize?

ROBERT: Well, that is an absolutely key stoic idea. Stoics view time as your most limited resource. It is far more important to discipline yourself about time than anything else. What Marcus Aurelius says is "for peace of mind, do less, but do it with greater concentration and eliminate the things that are non-essential." Just don't clutter up your calendar. Don't clutter up your mind. Don't use your time on things that don't really matter. Think very consciously about, "What really matters to me? What relationships matter, what projects matter, what skills matter, what objectives matter?" And use your time purposefully. It's a very key stoic principle. It's something that I've tried to follow in my life and a critical idea.

SPENCER: I could have a benefit from doing more of that. All right, last two questions. People who are incredibly successful often have a challenge that they can live in their own filter bubble where people don't want to disagree with them because they want their favor. Do you find you have a challenge getting people to be honest with you, or do you find that it's actually not so hard to get people to tell you the brutal honesty?

ROBERT: Well, I think if you write a book, people are probably going to tell you nice things about it rather than critical things about it, which is sort of the experience I'm having right now. But on a more serious level, if I'm having a meeting, I make a very conscious effort to ensure that the most junior people at the meeting are free to speak up and free to throw their ideas out. I even have a rule in certain kinds of meetings that no idea can be criticized until enough time has passed to evaluate them later, but the purpose of this meeting is to simply get ideas on the table. I'm very conscious of the fact that people are not necessarily comfortable speaking out in the presence of figures of authority and try to consciously encourage them to do that.

SPENCER: Final question, where do you think people should get their news from? I think this is a big struggle, that people end up getting news from just one perspective or from social media, et cetera.

ROBERT: I think you should consciously look for a variety of news sources. I read The New York Times, I read the Wall Street Journal, I read The Financial Times. I think The Economist is pretty good. There is a real issue when getting news from social media because it will be filtered in ways that are not helpful.

SPENCER: Robert, thanks so much for coming on.

ROBERT: Spencer, it's been a good conversation. I've enjoyed it. Thank you for inviting me.