This is part 2 of 2 with one of my all time favorite thinkers Adam Robinson. 

Adam is the Co-Founder of The Princeton Review, a rated chess master, an advisor to large hedge funds and financial institutions,  who uses a unique approach that combines game theory and behavioral economics to outthink global markets and anticipate when major trends will change. 

This is a wide ranging conversation exploring topics such as:

☑️The epiphany he had that has forever changed his life.

☑️Getting clarity around things that don’t make sense.

☑️The ideas Adam feels have been most impactful in his life.

☑️The most important questions you can ask yourself.

So get ready to expand your thinking and learn how to go from theory to action with Adam Robison!

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Adam Robinson Part 2

Asking Incredible Questions

[00:03:31] Sean: When opportunity meets preparation. That has me thinking, Adam, you’ve been remarkable at understanding the impact of questions and asking incredible questions, this is going to be a little bit out there. Say you were someone’s current day, Bobby Fischer and your 13-year-old self runs into yourself on the street corner of 34th and sixth, what is the crucial question that 13 year old should be asking of you?

[00:03:58] Adam: It’s an interesting question. And I don’t know that a 13-year-old or anyone would get that interested in what Adam has to say or do, because it’s such an eclectic path that I’ve had.

[00:04:18] Sean: That’s why I see so much beauty in it.

[00:04:21] Adam: Anyone who said, what’s the common denominator? You’ve done so many different things, what links at all? That would be an interesting question for me. But that’s a really good question, you think about the power of questions. The first time I met Buffet was at a fundraiser. It was a sit-down dinner, 12 of us at a fundraising dinner. I’m not going to mention any names or anything, but it was a fundraiser. So I’m not going to say what it was for, but it was sorry, 10 of us with Buffet. And each of us had paid a fair amount of money for the fundraiser to have this dinner.

And each of us got to ask one question. The whole dinner that was it, you could ask one question and not surprisingly, everybody asked him investment questions. It’s Warren Buffet, let’s ask them about investing, it’s something he knows about. And the reason we only got to ask one question is that we’d paid a lot of money to have dinner with Buffet and everybody at the dinner knew that everybody else would like to start to hog the conversation. I wouldn’t have, but everybody knew that somebody there would start to engage too much and we had paid to hear Buffet speak. That was the rule, one question.

So everybody asked him about investing this and that, and I asked him, my question was this, what keeps you up at night? This is a man who’s thought about the world very deeply. And he’s been through a world war, a depression, many economic cycles, many cultural cycles, he’s seen it all. And one of the wisest men who ever lived, he and Munger. And so what keeps you up at night? I remember him saying, oh, let me think about that. And because he’s seen it all, not much keeps him up at night. I think the question that you asked, anyone in that kind of situation like that you just asked me, it’s a non-obvious one and it’s an authentic one. 

When I met Fischer, who was my hero, I’d done nothing in the last three years, but spend three or four hours every night playing his games. And I wasn’t trying to memorize, it’s just that they were so beautiful. I knew them all by heart as it turns out, and so when I went up to him at that moment, I was authentic. There’s something else at that moment. And this is a really important thing to go back to your earlier question about the ideas you live by, is that my attention was focused on him there was no room to be self-conscious.

And when I was with my mother, a hundred yards away, I didn’t hesitate for a second. I didn’t go, okay, wait, there’s Bobby Fischer. Okay. Let me think about it. It was like, oh. And then when I was with it, when I immediately ran up to him, mind you, this is my hero, it didn’t even occur to me to think about myself, like, oh, what would he think if I ran up to him and asked him something. I wasn’t aware of myself. I was only aware of him and the question I had. And by the way, that was one question, I had hundreds of questions because I knew all of his games.

Your attention should either be in one of two places, either on the task at hand or the other person in front of you.

That was just the one that spilled out of my mouth first. That brings me to another powerful notion that your attention should either be in one of two places, either on the task at hand or the other person in front of you. You’re either alone working on something, and if you’re not, you’re with someone, that person has your full attention. I had an epiphany, I’ve always been that way, but about the power of that. Like right now, my attention is on you. I have no idea what you are thinking about me, so there’s no self-consciousness. Sometimes people say he seems so confident in public situations, but confidence would mean I was aware of myself.

I’m not confident, I’m only aware of the person in front of me or the task at hand. When you become aware of negative emotion, fear, doubt, anger, or any kind of negative emotion, it’s a reminder to refocus your attention on the person in front of you or the task at hand. Just do that, and other things will take care of themselves. And if you combine that with that earlier notion of inviting others to play. Now, if someone’s in front of me, they have a hundred percent of my attention and I’m just looking to have a good time, play, and with no agenda other than the play itself.

[00:11:23] Sean: There’s a line I love, I can’t remember who it’s attributed to, but this makes me think of it, and that’s, “ecstasy is attention at its fullest”. It’s a line I’ve thought a lot about.

[00:11:35] Adam: That’s fascinating. So the derivation of ecstasy you’re exactly right. Funny, you should mention that because ecstasy is to be outside of yourself. That’s literally what it means. You look up the derivation needs to be outside of yourself, that’s ecstasy. And again, my attention is on the other person or the task at hand, so each moment in a sense is ecstatic. This reminds me of another well, it’s a Greek word, “enthousiasmos”. People are always surprised by the derivation of enthusiasm, like the etymology from ancient Greek means to be filled with God.

 The “thou” in enthusiasm is a derivation from Theo. In theology, Theo is God. And that the Latin word for that is inspiration, which means to breathe in God. You’re exactly right on ecstasy. You’re outside of yourself and to be liberated from yourself. Michael Jordan said that he never once thought about missing a shot. And he couldn’t because he was fully focused on making the shot. Because if you’re worried about missing the shot, your attention is misplaced. He missed lots of shots, but that never entered his head because he was fully focused on making shots. Attention is super important.

Uncovering The Through-line

[00:13:33] Sean: I’m even blown away hearing about your 13-year-old self, that commitment, that dedication, that focus, was that a skill you had prior, or was that love for what you were trying to do in chess, did that bring that out of you?

[00:13:48] Adam: So it’s interesting. Remember it was a pretty simple goal. I just wanted to beat a kid in chess, that was it. It wasn’t like, oh, I’m going to make the chess team. Swimming, I was dedicated to and it didn’t occur to me to go, oh, maybe I should find out someone who knows how to go about it. Maybe there’s a chess coach or chess tutor. No. And I didn’t think about it, I didn’t join the chess team until late my sophomore year, like a year and a half later. I just wanted to beat the kid, and then I really liked the Fischer’s games and I would just study them.

And so it didn’t set out to be any grand goal. You asked me something earlier, Sean, and you said about when you’re earlier in your career, you’re casting about like, what is this, what am I building here with my life? And I had a recollection only a few years ago about something when I was 12. So you mentioned the age of 13, so I’m now addressing, I know you have men and women in your audience, listening, I know this is true for men because I was because I am a man. I don’t know if the same thing applies to women, but it’s this, and I would assert it, that men know who they are, males know who they are and will be in the world by the age of 12 before you’re 13.

For example, Buffet, when he was 12, his dad took him on a trip from Omaha to New York. He was 12 and this is 1942, depression, World War II raging and stuff, and his dad takes him from Omaha to New York, and on that trip takes him among various places took him to the New York Stock Exchange. And after that trip, Buffet turns to his dad and he revered his father, dad,  I’m going to become the richest man in the world so that I can give it all away. That was a statement he made to his dad when he was 12. So get this, and I only realized this a few years ago, it was a memory. 

I remember when I was 12, it was a mid-spring day, say April or May. It was a Sunday and I was walking with my dad, all 12 years old, and I used to have really deep philosophical conversations with my father, always like hours. And anyway, I’m talking about how much I hate school. I hate school. Why do I have to go to school? I always just wanted to be left alone so I could daydream or read whatever I wanted to read. So I’m with my dad and I’m talking about how much I hate school. And he turns to me and asks, “So what are you going to do about it?”

He meant that as a philosophical problem. Okay. You Adam, he was saying to me, you’re in a situation you don’t like, and you have to go to school. You’re not getting out of that, buddy. So what are you going to do about it? In other words, how are you going to frame this? How are you going to approach this? How are you going to deal with the fact that you’re stuck going to school? That was embedded within the question? And kind of frustrating, I said, I don’t know, maybe one day I’ll start my own. I had no entrepreneurial inkling at the time, I’m all at 12 years old. It’d be like someone saying, oh, I hate food, and my father turned and said, what are you gonna do about it? 

I don’t know, maybe one day I’ll start my restaurant, but that’s what I said, like for a 12-year-old boy who hated school. And it wasn’t like, oh yes, I could do school better. I hated it. I didn’t like it. And I think anyone else would like, it’s not like, oh yeah, I want to torture your kids too. So mind you, I’m sharing a memory that I only had about three or four years ago and you know because you know me and my background. When I was 25, I got out of Oxford and a law degree don’t know what I’m doing, and a year later I co-founded a company called the Princeton Review.

So I started a school 13 years after I said, I was, and that still goes on today. Millions of kids have read things that I developed. I remembered that memory only a few years ago and I went, wow, I did start school, just like I told my dad. And it wasn’t like a vow, like Buffet, that statement to his father, that was a commitment. I’m going to become the richest, he was proclaiming that. I wasn’t proclaiming it. Oh yes. I’m going to start school. No. And, I’ve asked others, my male friends and they go, yeah, it doesn’t have to be at the age of 12, but by the age of 12. And I say this, so if you are a male and you’re like, oh, what should I be doing in the world, that when you were a boy, you knew stuff about yourself. 

And I say, the reason 12 is so important to cut off is by the time you hit 13 and enter puberty, all of a sudden, you begin to compare yourself to other people, dating and, oh, I got to look good for them. It muddies the core authentic proclamation. As just a boy I want to do that not to prove myself. I think it’s worth everyone and it may be true also for girls, women, you know, that their path is theirs. It’s worth revisiting your childhood memories, the things you loved to do. So there, that’s another invitation, I’m inviting people to go back to their memories. Okay. Let’s see. Yeah, let’s try it. I always liked riding horses. What was that about? Whatever it is.

[00:21:39] Sean: That’s beautiful. I feel like it is a very important exercise to do that. One of the things you hit on there that has me thinking right now is around 13, you hit puberty, you’re comparing yourself. It’s almost that childlike, unobstructed authentic self-expression at that age, and that’s how you uncover that through-line, those golden threads.

[00:22:00] Adam: Exactly. So well said, that’s where you discover the through-line. You’ve just started it, it was very odd that through-line because I was an introvert. It wasn’t like, I’m going to start school so I can talk to others. This is how much of an introvert I was, so in high school, yeah, I’m on the chess team and I’m on the swim team, but those are the only people I talked to. And some people told me after I graduated, that they had never seen me speak not once in four years of high school, not once, just in my little world. Again, I had that epiphany and I’ve been very much informed my whole life, and then something shifted about six years ago, people, Adam’s in a candy store with lots of people, just have fun, play. And I’m doing serious stuff in the world, and yet it’s all a form of play.

[00:23:03] Sean: With that, one of the things that you’ve brought tremendous clarity to for me and my life is deciding to not ask yourself the question, what do I want to do? But more importantly, who do I want to be?

[00:23:17] Adam: Yeah. And unless you love doing something, I go, yes. Brady, ah, football, I love football, I want to be a football player. But then becomes, who do you want to be in the world? Which goes back to that earlier conversation we had about what statement are you making to the world? And the statement I’m making with much of what I do is, play is really important in everything you do. I mean, philosophically important, not just, oh, you should have a good time. That’s the highest form of gratitude for the gift of life, is play. It’s the highest form of reverence. The most serious things should be approached playfully.

Finding Clarity Through Distillation

[00:24:26] Sean: You mentioned some of the things you’re doing in this world are pretty serious and they are, but what I have such deep, profound respect for what you do is the clarity you can bring to those things where things don’t make sense to the majority of people, somehow you’re able to find clarity there. I would love to just hear you talk through this.

[00:24:47] Adam: Well, I mentioned before about my weakness, the strength that comes out of weakness, is that I have a hard time understanding complexity, complicated things. So I’m always taking complexity, I have like a cocoa puffs brain and I reduce it down to something that I can understand. And in that process of distilling it down, I get to court truths that are denied to people who can deal with complexity. But at that complexity is unwieldy which is why you need, again, whether in performance, sports, or art or anything, boil it down to a few things, and then you can use those things very well.

It’s all about distilling and I just don’t have to create a process, and much of it comes down to deconstructing it and looking at it in the simplest possible way. I remember as a boy, my father, again, we had these deep philosophical conversations, and I remember he was saying something, he said, if you can’t explain it simply, you don’t understand it. So, language use, and most people explain things really in complex ways. I alluded to a very thick book by a very famous person on how to live your life, could you boil that whole thick book down to a few rules that I can use?

And so it comes from a ruthless insistence on making things simple enough so that I, Adam can understand that. I figured if I can understand them, then other people can. When I started the Princeton Review with my friend John Katzman, I had no idea what I was doing, I was like, oh, maybe I’ll tutor a couple of kids a day, write novels on the side, and it grew and became the Princeton Review. Now that you said, I’m just thinking about this for the first time, it’s the same thing that I threw myself into the chess. You just throw yourself into it and you just keep digging, digging, and from that, you get some few core principles, and Ahas.

Think about it like this. When Wayne Gretzky was playing hockey, he was playing a very different game from everybody else on the ice. Same with Michael Jordan or anybody in any of those or Bruce Lee fighting. His fighting is very different from whoever his partner is. You just get the idea that they’re looking at things very simply. It’s the only way you can function at a very high level. 

Anti-confirmation Bias

One of my favorite questions, which I stole from Steve Cohen, the Met owner, I was talking with him about something and his friend and he said, “What would you need to see to know that you were wrong?” And there that’s a boom question. And because most people, when they’re presenting ideas, whether it’s to buy gold or invest in this or buy NFTs or whatever it is, they have a view, and they’re trying to convince you to do something. And always the question is, what would you need to see to know that I should be shorting gold? If they don’t have an answer to that question. They haven’t thought it through. 

And that’s a great internal check, like what would I need to see to know that I was wrong and, of course, you know about confirmation bias, right? Human beings are designed to look for information that confirms what it is that they already believe. I’m doing exactly the opposite always in real-time. Once I form a belief, I am now actively looking to disprove it. If I believe that gold will go up, I’ve done the analysis gold will move higher. I don’t look for information to confirm what I already know, that would be a waste. All I’m doing is, I’m looking at very specific things. 

What would I need to see to know I should be shorting gold, like oh, interest rates just spiked, gold is going down, but the dollar just jumped 2% this week, gold’s going down. I have very specific things and you can do that even in your personal life. Like what would I need to see to know that this person is committed to what I’m doing or what we’re doing? What would I need to see to tell me that that wasn’t the case? Again, it’s anti-confirmation bias. I think that’s a really important tool to add to our Batman utility belt when we go camping with Musk in Canada.

Living The Timeless Principles As Opposed To Capturing Them

[00:31:19] Sean: This question is fascinating to me, and I hope you don’t view this as “too in the weeds”. You do such a good job at deconstructing these timeless principles. And I’m just wondering for you, like, are you capturing these? Are you writing them down so you revisit or once you reach a deep truth, you just know it, and it is just in your head?

[00:31:37] Adam: Remember, it’s not in my head, I’m living it. It’s not something I have to remind myself of. This is a very profound topic. So all of your questions are good, being in the weeds with you. For example, when I saw  Bobby Fischer and changed my life in a pretty significant way. How often does somebody bump into their hero?  And that person was a famous recluse. I’m like literally one of 10 people in his whole life that he ever let in because he massively distrusted everyone, unfortunately. What was I talking about just a second ago?

[00:32:41] Sean: So I was asking in terms of when you’re deconstructing these ideas, you live them as opposed to just having them.

[00:32:50] Adam: Okay. Now I remember. Someone listening to that story, or if they were right in the room when I was saying, they might say, well, Adam, you know, there are no coincidences. How often have you heard someone say that there are no coincidences? So the person asserting that, do they live their life by that statement? Like if you believed that there are no coincidences, and I’m confessing to you now that I don’t. For example, what are the odds that you would bump into your hero? I did in New York City and I wasn’t even living in New York City.

I was living in Evanston and he would just happen to shop when you’re at a corner that you rarely on with your mother crowded. And I would say the odds looking back on it were a hundred percent, which is another interesting topic, maybe we’ll get to it. There are no coincidences, but they don’t live their day-to-day life by that. And so any idea that I get I ask can I use this in real-time? So for example, I’ve told you that, and you know this from other times we’ve spoken about this, about creating fun and delight, like inviting others, be playful and invite them to play with no agenda. How do I live that life?

So there are times when somebody says something I want to go, eh, that’s not true. And I will find myself at that moment in real-time going is what I’m about to say going to increase the fun and delight in the situation, or is it going to do the opposite? There are a lot of times I catch myself, Oh, I can’t say that even though I’m tempted. There are a lot of times I want to say or do something and yet I know it violates that principle. By the way, I’m not perfect at times I just go aah but as often as I can, as a human being, other things equal, there I optimize around maximizing play in any given situation. That’s what I’m optimizing for.

And someone else might be optimizing to get noticed or, oh, this or that, and I’m not judging those whatever, but I’m very clear about optimizing around something. If an idea doesn’t help you live your life or help others that you can share their lives. Like you started this off and said, oh, we’re going to uplevel here in this conversation, we’ve discussed lots of things. So I don’t write them down, I live them. I don’t think there’s much to be said. I think that all that can be said about life and would constitute all the wisdom that is known, can be reduced down to a very few principles, like not much to be said.

And then everything else is sort of a corollary of those few principles. I think it’s about just living in and doing so mindfully. Do you really, this is so cliche, but walk the talk? Do you embody that principle mindfully in real-time, minute-to-minute? It’s vitally important, like, you know, anything you’ve read of Munger and Buffet that they are living that day to day, minute to minute, that’s how they live their lives. There’s no doubt. I think that’s important to live mindfully around optimizing whatever you’re trying to optimize in the world, this gift we’ve been given as a planet.

Pascal’s Wager & Adam’s Wager

I mentioned that I’m doing some serious stuff in the world, and so one of the things that I’m doing is I pose myself the following quiz, and it’s a pretty serious one. What if humanity, our species was at a critical existential crisis right now? What if we don’t get this moment right, this moment, next few years we are likely going to spiral down into a very bad situation, possibly the end of our species? Pascal, a French philosopher, mathematician, something known as Pascal’s wager like he chose to believe in God because there’s four by four matrix, I believe in God or I don’t and God exists or doesn’t. 

So again, you go through the matrix. If I believe in God and he exists, yes, good for me. I’m lucky forever. If I believe in God, but he doesn’t exist, no foul, no harm. If I don’t believe in God and he doesn’t exist, no foul, no harm. If I don’t believe in God and he does exist, I’m in trouble. So you just go through the little four-by-four grid, mathematician philosopher he was, so therefore I choose to believe in God. So, here’s Adam’s wager. So here’s my conjecture, we are either at the end of times for our species, humanity or we’re not. Do you believe that or not? And if we are, and we don’t do anything, we’re screwed. 

If we are, if this is the end of the road, and I know people, of course, they go, oh, you’re just being alarmist, in the past we’ve dealt with very serious things, World War II, depression, lots of serious crisis, at the moment it seems it’s never been worse. And I’m asserting after a lifetime of thinking about things, I can think of no other time in history ever, that was this serious. And we don’t intend to go in it, but I am either right in that assertion or I’m not. Punchline coming in about 60 seconds. So if Adam is right and we don’t do anything, we don’t change what we’re doing, remember you’re not getting the results you want, got to change what you’re doing.

So if we don’t change what we’re doing, we’re screwed if Adam is correct. And if Adam is incorrect, that it’s not the end of time, and we don’t change what we’re doing, okay, still not a great world. They’re big problems. If Adam is incorrect, it’s not the end of time and if we don’t change and if we do change well, that’s also good because things could be improved. So either way, it argues that we, as a planet need a change big time, big time. Everyone listening to me right now has the sense that the world is flying apart. There’s a great poem by Yeats written in 1917 in World War I called The Second Coming. 

He said the world is flying apart in anarchy. He said the best lack all conviction, and the worst of us are full of passionate intensity. And that’s like such a description. If you’re listening to me right now, you should look up the poem The Second Coming, it’s very short, very short, and that’s 1917. So 105 years ago in the aftermath of World War I, which was horrific. So now I’ll make the following statement or ask the following question, if you thought it was the end of time, in other words, for our species, as humanity, we have really messed things up, and we have the technology now to do a lot of damage quickly, what steps would you take? And you have to get it right.

I’ve been pondering that question for five years and  I’ve come up with an answer. What would you do if you knew you had to get everyone to change what they were doing, and you had one shot at it? Do you remember the movie Armageddon? So in Armageddon, those of you who haven’t seen the movie, a comet is headed toward earth, and if Bruce Willis and his ragtag team of wildcatters don’t stop that comet, it’s game over. So they have to stop the comet. I look at the world with that kind of urgency and have for the last five years and have addressed it.

I think I figured out an answer. It takes a little while, I’m about to publish a white paper called the Renaissance Project. You in the weed questions, they’ve been so good because it all circles back to who do I want to be in the world, share, and there’s play and there’s a world that’s falling apart. There is a lot of pain in the world clearly, and it’s getting worse every day. When I think back about history, I look back at the difference between now and then is the technology. We can do a lot of harm, really fast, really fast. Genetic engineering just takes one virus to get all wiped out or a new life form.

AI is a very serious threat. There are all these technological threats, not to mention the social, political, and economic unrest in the world. I’ve been thinking very deeply. And again, here’s the question, what would you do if you knew you had to succeed, not make your best effort like you had to stop the comet? That’s a question I’ve been working on as deeply as the other questions you’ve heard me think about. And again, have to succeed, not just good college try. That sounds like a really serious topic and it is but I’m playful when I approach it, and I’m gathering resources to make it happen. 

Long-form Conversation with Anyone Dead or Alive

[00:45:58] Sean: Adam, thank you for this, for the wisdom, the insights, the tales along the way. This has just been as we mentioned five years in the making, this was a true pleasure for me. I would love to know one final question, if you could do this long-form conversation with anyone dead or alive, just not a family member or friend, who would you want to spend an evening with just asking questions?

[00:46:27] Adam: Wow. Wow. A bunch of names comes to me. Oh, that’s so tough. Okay. Here’s the thought experiment, I get to meet Jesus Christ and have dinner with him. I get to talk to him today, I say, knowing that much of your wisdom has been misinterpreted would you say anything different? Seeing the world that you see today if you could go back and say things differently would you say things differently? That would be a very interesting conversation because here’s a man clearly, and he’s not the only man in history or woman in history who was dedicated to up-leveling as many people as he or she could, and yet if they were to look at the world in all the wisdom that they imparted, has it made a difference? 

And of course, it has, every piece of advice is an invitation to accept it or reject it. And they can only invite people, here, that’s the door out of your jail cell human beings. There that’s the door, you can open it, you can go right out or you can choose to be inside a jail cell that you call life. You can only point the way. I’d want to know that because it comes back to me like trying to help as many people. So given what you now see, what advice would you give yourself, and what advice would you now give me, Adam? I can think of other people.

[00:49:09] Sean: Adam Robinson, that is a beautiful place to close out what I hope would be one of the multiple conversations on What Got You There. So, thanks again.

[00:49:17] Adam: Let’s go back in the weeds and get a tweet and invite Elon, must go camping with us, and ask lots of questions.

[00:49:29] Sean: You guys made it to the end of another episode of What Got You There. I hope you guys enjoyed it. I do appreciate you taking the time to listen all the way through. If you found value in this, the best way you can support the show is by giving us a review, rating it, sharing it with your friends, and also sharing it on social. I can’t tell you how much I appreciate it. Looking forward to you guys, listening to another episode.