The Exchanges

Q like an Asian mom thing, I feel like. So good. Um, I want to talk about, like, okay, this is a little bit granular, but let's get granular, beginning of the year. Um, Let's say that your partner does make way more money than you do or way less. Do you split things 50 50 or how do you have that conversation with your partner about who pays for what?

A Yeah, you can split a 50 50 if you want to break up. Um, no, listen, I am someone who doesn't believe in things being equal. They have to be equitable because say we're dating and you make 250,000 dollars a year. And I make, I don't know, let's call it, 80,000 dollars a year. We go and get an apartment together and the rent is, you know, four grand a month. That is a huge proportion of my income, right? 80,000 dollars after taxes, you're probably looking at maybe 60 grand if we're lucky. Two grand a month times 12, 24 grand. 24 grand of 60 grand is what? A third over a third. 24 grand of two 50. Let's say you walk away with one 75. Oh, that's weird. That seems to be a much smaller fraction. No, we are not paying a commensurate amount on our rent. Because of that, I am shouldering a larger burden than you are, even though we are paying the same. And the problem with that is, over time, that leads to a lot of resentment. Because you know what's gonna happen? You're gonna pay the rent, and then you're gonna go around your merry way. You're gonna go to sushi dinner, you're gonna be able to go on vacation, you're going to buy nice clothes. I only have 36 grand left that I'm working with. I'm not going out to sushi dinner. So then I'm going to tell you, hey, I don't want to go out to date night. You're going to think I'm a killjoy. I can't afford to go on vacation. So now you have to…

AI assessment note: “You can split a 50 50 if you want to break up.”

Q have more friends than you, more status, however the game is that you want to play. What do you do when you're in that room to not look like you want to impress them when all you want to do is impress them? Or said alternatively, inverse, always inverse, what should you absolutely not do? So, brand new in a room. Tons of successful people. Please don't do these things.

A Don't name drop. It's a turn off. That can organically come up later, but if you're name dropping as a way to impress, you will absolutely turn people off because they probably know all the same people and know more people. So it'll show that you're really trying to get in. That's the first one. The second one is you don't have to go in there and try and impress them with all your achievements. Oh, when I did this, oh, when I did that, so don't do that. Don't drop all the achievements in there. Don't one up people. We see this a lot. Someone will be sharing a success and then someone else will jump in and say, oh, well, when I, and then they're trying to, It's not going to go down well at all. The best thing you can do is be interested. Show them respect. We've heard this a million times. Ask them questions. Show genuine curiosity, not only about their businesses, but also about them. People generally like talking to them, talking about themselves. It lights up a part of our brain, which is rewarding. Not everybody, but most, especially people who tend to be very successful in business, who are at events in these rooms. They love talking about themselves. So if you could ask them questions and not just the surface questions, get deeper. You know, what did you learn about yourself during that experience? What was one of the most challenging things you faced? You don't want to pu…

AI assessment note: “Don't name drop. It's a turn off.”

Q Love that. Let's talk about, um, high performers for a second. One, do high performers not have self-doubt, or do high performers, in fact, have a lot of self-doubt?

A In our experience, high performers have a lot of self-doubt, and they're very aware of their self-doubt because they hear it, and they feel like it is either something that's completely getting in their way, or they need it because that's what pushes them. But again, when we look at what the research says about high performance, we know that you're actually going to be more inclined to keep pushing, more inclined to keep growing, if you're more compassionate to yourself, and have less self-criticism, and less of that self-doubt. Fascinatingly, if we look at imposter syndrome, so imposter syndrome was initially called imposter phenomenon. It was a phenomenon that they found mainly in high performing women, but since they found it's actually prevalent Everywhere, including with men. And some studies have found that up to 82% of people have felt like an imposter at some point in their lives or careers. Which is huge. That's eight out of 10 people feeling like they don't deserve their success. So the definition of imposter phenomenon is believing that other people think that you are more capable or smarter than you actually are. So it's a mismatch between Competence. You know, Cody, early on you said competence and confidence usually grow, and that's how it should be when you're healthy, when everything is working. Imposter phenomenon is where your competence has increased because …

AI assessment note: “In our experience, high performers have a lot of self-doubt”

Q want people to get today, is how to take these core ideas that lead to a disciplined And in some ways more beautiful life because of that discipline and get it simply. And so you had this great quote that I loved, which is, when you're lacking motivation, remind yourself, discipline now, freedom later, the labor will pass and the rewards will last. Can you tell me more about that?

A Yeah, there's a line from one of the great Stoic teachers, his name was Musonius Rufus, and he said, you know, when you do something in pursuit of pleasure, or you're taking a shortcut, like, the benefit that you get from that, uh, passes quickly, but the shame or the consequence of it lasts, and he says, conversely, when you do something hard, the labor passes quickly, but, like, the good from that remains. Like, when you work out, it's painful in the moment, When you get in a cold plunge, it's unpleasant at first. You know, when you get up early, you're tired. When you work an extra hour, you know, that's, that there's a, a cost to that. But the benefits, the benefits, they not just endure, in many cases, way off in the future, the pleasures or the benefits that you experience are a lagging indicator from that. And so, if, if we want to think of, of discipline Like, discipline is, or self-discipline anyway, is about constraint. Do this, don't do that, not, that's hard, but it provides you the freedom down the road, because you either have some financial security, you have strength, you have confidence, you have health, whatever the thing you're, Delaying gratification for, well, at some point you do get that gratification, and it's a more sustainable, enduring, and stronger reward than whatever you would like to get in this moment.

AI assessment note: “there's a line from one of the great Stoic teachers, his name was Musonius Rufus”

Q So good. Yeah, you had this video that I saw the other day that I loved. You were having a 16 and a half hour day, and someone asked you, what keeps you motivated on that kind of day? And you said, total bars, you said.

A Pure adrenaline tracing through my bones because that fear of losing hurts a lot worse than the pain of winning. Yes, I do remember saying that. That was a long day because I had to open up our Rhode Island office, and so the day started in New York, helicopter to Rhode Island, appointments back to back to back to back to back to back to back, launch party, helicopter back to New York City, back in the car to do all the work I hadn't done that day. Like, the work doesn't go away just because you're traveling or doing other things, you know, and I, I try to swallow the tired, and I try to appreciate the tired. If I'm not tired, Then I'm probably not pushing hard enough for better or for worse, but I do agree with that. I think, you know, you listen to a lot of CEOs, a lot of major athletes, and I think they all have this disease where they hate losing more than they like winning, and I definitely feel the same way.

AI assessment note: “Pure adrenaline tracing through my bones because that fear of losing hurts a lot worse”

Q Cause it can't be cheap too. Like going to alpha school, what does it cost?

A So alpha school is expensive. So our tuition is 40 to 75,000 dollars. And so when we back to design goal though, when I designed it, I was like, pretend price is no object. What can you do now? We are building a whole nother set of schools, right? At half the price at 20,000 dollars. We spend in America, 20,000 dollars a kid. To educate them. So that's sort of my price target. We're launching, right, and we've launched 10 of them so far, we hope to open hundreds next year, of these Texas sports academies. They're 15,000 dollars tuition. My middle school, right, they're micro schools, they're 25 kids, middle school D-one bound athletes. Think 25 really good basketball players, right, in middle school who do academics in the morning, you know, basketball in the afternoon. And so think of hundreds of these schools around Texas, uh, at 15,000, which the voucher program just was announced, which is like 12 grand. So parent pay will be like 304 hundred dollars a month, right? So dramatically more accessible than Alpha. And so we're building a whole set of schools like this. I need lots of entrepreneurs to go build this, right? We need a school for gifted and talented kids, right? Those kind of things. Sports, arts, theater, music.

AI assessment note: “So our tuition is 40 to 75,000 dollars.”

Q How long did you work like that, where it was like a dollar in, a dollar out, a dollar in, a dollar out?

A For a long time, Cody, no one would invest in me. Okay. So I had to do it on credit card debt and a line of credit for 10 years. I bootstrapped this business. And so every single dollar I made, I had to figure out, okay, how am I going to reinvest it and get the biggest ROI I can on that dollar? What I love about it is it made me incredibly scrappy. And as I run a billion dollar business today, I still have that scrappy startup mindset. And I'm so thoughtful about how we spend our money, What we're spending it on. What are we doing and thinking about it? And everyone I hire, I really remind them, like, I remember when I couldn't afford a second set of tools, folks. So before we just throw out, you know, a million dollars on this project, let's bid it out. Let's really think about what we're doing. What are we going to get in return for this? Why are we doing it? And it's kind of having that, you know, when you start with nothing and you build it, you never forget how hard that is.

AI assessment note: “for 10 years. I bootstrapped this business.”

Q You're like, calm down. He's fine. He's good. He's good. So what, what makes a good salesperson? You mentioned authentic, but if you were like, all right, if you want to get good at sales, this is what you need to do. What would you say?

A I think you need to come in. You need to be articulate what it is you're trying to sell in a very short sentence, right? Be very clear. Be very concise with your pitch and eye contact. And then ask questions. If they're saying no to you, this is the greatest opportunity for information. To me, that is on in the mirror, meaning the conversation has just got it started. So you say, no, you don't want the collection. I go, okay, well, what did you, what didn't you see today that you would have liked to see? What can I show you next time? Cause I've already now setting the appointment for the next time I'm coming back. When I come back in spring with my next season, I'd like to know what I could, could bring that you might be more excited about seeing. What other designers are you buying that you're really excited about? Can you tell me what it is about them that you like? So all of a sudden my sales call became this information source that I'm now going to take back with me and learn from and then come back to. And I promise most of those no's turned into a yes because of that. I didn't go, okay, oh, you don't like me. Okay. Bye. And then we're going to see you again. It was, I'm going to learn and I'm going to win a yes from you. And I'm going to keep trying. And there was, I would said cupcakes and cookies to buyers in the early days. Um, you know, if it was a spring theme, I'd …

AI assessment note: “You need to be articulate what it is you're trying to sell in a very short sentence”

Q article the other day that, um, we have a sleep epidemic in tandem with what you talk about often, which is a health epidemic. Like people are sleeping less. Their sleep quality is worse than ever. If somebody is listening to this right now and saying, I literally cannot sleep. I'm suffering from it. What else do you do? What do you tell somebody to do who's suffering from sleep?

A Yeah, a lot of people are not sleeping well, and to be frank, I don't actually love sleeping, but you have to do it. Here's a handful of things. So number one is wake up at the same time and go to bed at the same time. Limit overhead lights and a lot of stimulation. Number two, do not have, it's not great to have these huge meals before bed, but one of the things that we've seen in our clinical practice is people get hypoglycemic before, or actually in the middle of the night. So about four hours after people fall asleep, we see that they oftentimes get reactive hypoglycemia. Which is just a big word for low blood sugar, and it wakes them up. So, having a mixed meal, maybe a handful of carbohydrates and a handful of protein, you don't need to overcomplicate it, handful of both, could be yogurt and some fruit. And then you go to bed, you're much less likely to wake up with this reactive hypoglycemia.

AI assessment note: “Here's a handful of things. So number one is wake up at the same time”

Q get in trouble are the ones that think they're the best with it, right? And so, I want to talk about, I want to talk about a couple of things. You can kind of pick which one. Uh, I want to talk about either the pumpkin plan, or I want to talk about clockwork, or I want to talk about beacon. Do any of those speak to you in this?

A Yeah, they do. So I'd say pumpkin plan to start. Um, what I did just to give context, it's one of the books I wrote, uh, and it's the runner up to profit first in popularity. What I did was I hired a business coach before business coaches really existed. This is back in the nineties. And, uh, he came into my business and said, day one, we're going to go to a pumpkin field. I'm like, what? He's like, you gotta understand biology. Cause there's this thing called biomimicry. And when you study what mother nature's figured out, She's pretty freaking smart, and she spent a lot of time figuring things out. You can copy those strategies, and usually they have a more, a better success rate than something that's artificially engineered. So I went to a pumpkin farm, and studied colossal pumpkin farming, and sure enough, it works for business too, so that's the context.

AI assessment note: “Yeah, they do. So I'd say pumpkin plan to start.”

Q Do entrepreneurs Do entrepreneurs sell enough to their customers? Are most entrepreneurs scared of selling?

A They absolutely do not sell enough, and they don't sell the right way. I actually believe MVPs are not the right way to sell. So an MVP is a minimum viable product. I think that's too far advanced. We do a technique we call sell the tell. What we do is say, so we, I was a co-owner in a manufacturing business for a while, that we made leather products, sheaths specifically for knives, and instead of making a prototype and seeing what was out there, we simply Announce our audience. We're thinking about making a sheath, and it's gonna have this feature and that feature. Are you interested in buying it? But we ask the most important question. If you are, put down a deposit now. People speak the truth through their wallet. I was actually thinking about doing a conference at my old high school, but to pull it off, we needed 250 people there. We reached out to our audience. We had 75 people put a deposit down, and we said, no, this isn't gonna go, and refunded their deposit. Ironically, Prior to that, uh, our marketing team said, why don't we just ask? We had over a thousand people say, oh, I'm in. That's amazing. And if we acted on that, we would have blown money and embarrassed myself at my old high school.

AI assessment note: “They absolutely do not sell enough, and they don't sell the right way.”

Q That's so good. Um, let, let's talk about, um, distraction a little bit. You have a lot in multiple of your books, I think I'm referencing the pumpkin plan more here, but how do you personally decide when to double down on an idea versus when to call it a distraction and cut it?

A Yeah. So, um, I, I, we generally look at a revenue threshold, because that's just a, a shocking metric to many small businesses. We generally say, if you're not generating ten million dollars doing your one thing, you haven't arrived yet, you're not good enough yet. For most businesses, that's about point oh, one percent of the market cap. So, it's nothing. Yet most businesses said, oh, we're doing 300,000 in revenue, I should diversify and do more things, and it starts diluting you. It's all about the efficiency game. That's where we focus. The second thing is we just do diagnostics with AI. It's so easy now. Just look at the customer base, what they're consuming, what's the profitability per product, and we just focus in on those few things. I think businesses pursue diversification too quickly because we hear if you're diversified, you're safe, you're protected, but it also stalls growth.

AI assessment note: “if you're not generating ten million dollars doing your one thing, you haven't arrived yet”

Q invested in the business here. I, um, you know, I hired a new person, but I found that if we don't become better, our business never gets better. And so I'm curious, you've been in the sort of educational business for a long time. Do you still have coaches and mentors? How do you think about investing in yourself as the entrepreneur and getting better? Is that important to you?

A Yeah. So wickedly important. Surprise. Um, what I do is identified what is the role that I enjoy the most, meaning gives me the most joy. But first I had to eradicate myself from doing it. So let me explain. I get the most joy from being a spokesperson for my brand, ok? Um, I realize that requires a lot of public speaking, and I realize if I'm the only person doing it, I become the linchpin for my business. So, first I educated about 50 people on speaking on Profit First. In fact, there's like three Profit First keynotes going on today, and I'm not doing any of them. So that's the first thing, so I'm not necessary. Then I said, okay, I own the business, and I want to do what gives me joy. I'm not going to sit on the beach and stuff, so I'm going to reinsert myself, I want to be the best spokesperson I can. So, uh, I go to improv classes. Uh, I study comedy. Um, I, I look at, what, what do my contemporaries do? And most people sit behind a dais and, like, they just, like, that's the one thing I can't do. I have to be different. So, um, I study theatrics, performance, all those things constantly. I have a speaking coach who comes to my events and critiques me, sometimes live. Like, he'll be doing signals. He'll sit in the front row. He's like, Like we have these hand signals, like, oh gosh, hands out of your pocket. Um, named John Bates. Um, yeah, so I, I, I very much invested in…

AI assessment note: “I have a speaking coach who comes to my events and critiques me”

Q So you once started a crypto project with John McAfee, who was easily, I think the most Accentric, paranoid, and wild entrepreneur, maybe of all times. He founded, like, founded and sold McAfee antivirus software, investigated for murder in Belize, and later returned to the U.S. where he ran for president, not once, but twice. I think there's a whole Netflix documentary about him. Is that right?

A That's correct, yeah. So, it was like seven years ago, uh, eight, I don't know, but crypto was going crazy, and I was getting involved because I'm, you know, always distracted. And I kind of found this math equation that helped me predict the price of cryptocurrencies. And it was very simple. Here's the whole secret. Okay. I would, I found a way to measure how much hype, uh, cryptocurrency had, how many people were talking about on Twitter, Reddit, Facebook. And I put that into a number from one to a hundred. And then I use public websites to find out the market cap. Of the cryptocurrency, how much it was worth. And then I just divided the two numbers. So if there was a cryptocurrency that was very big, very popular, but people weren't really talking about it. My algorithm division told me it was going to go down in value at some point. Or if everyone was talking about something and it was had a small market cap, then it would go up in value. So I started investing my own money in this. It was working. And I felt like I had just discovered like Newtonian physics or something, right? I was like, this is huge. I'm going to be so rich. This is amazing. Um, but I, this was like years before I ever started publishing content. I had no following, no audience, no rich friends, nothing. And so I thought, who's the biggest name in crypto? John McAvee. He had like a million Twitter follo…

AI assessment note: “That's correct, yeah. So, it was like seven years ago”

Q Wild. And so do you think a lot of your entrepreneurial chops come from? Doing hard things like that really young?

A Oh, a hundred percent. Um, I was like, in high school, you know, I, I, I had a single mom. She was a wait, a waitress, and I had bad grades. I was not motivated. I was not driven. I was not valedictorian, three point O GPA, stupid stuff on the weekends. But after knocking doors in Eastern Europe in a foreign language for two years, and I added up how many times I got rejected loosely because we would knock on doors all day. Every day. Um, and so if you add that up, like x doors per day, it's like 24,000 times. Rejected to my face, ok? This isn't like a mean email. Like, I don't want what you're selling me. When you do that for two years and you come home, I can, I just remember sitting in my room after coming home thinking like, I can freaking do anything. Like, and I will. Like, this is America. I can do whatever I want. Because I met a lot of really smart, kind, talented people over there that had no opportunity. They could not get ahead if they wanted to. And I was like, I can do whatever I want here compared to Hungary, and so I've just been trying to do that ever since.

AI assessment note: “Oh, a hundred percent.”

Q First your own, then a little bit of YC, then a little bit of third party investors. It's not like this was an overnight success at all, and so I, I'm curious, did you ever have a moment where you were like, we are not gonna make it, and I'm not good enough, and this company's not gonna work out?

A Yeah, yeah, I mean, in, uh, 20, 24, early 24, so last year, um, the company had not been growing all that much. We're actually, we're kind of hit a plateau and started decreasing a little bit, so we were in this awkward Position where we make it easy enough to get started, but not enough to get you all the way to building a business or a real piece of software. And because our focus is on getting everyone to make applications, anyone with a dream without any skill or background in computer science should be able to come to Replit and make an app that was always the kind of the core of the mission. We're also not very good for professional developers because they needed all these tools that we didn't have. And so we're in this like awkward middle and not making any revenue and have this Really large staff, 130 people, had raised two hundred million dollars, and as you know, you know, you, uh, you talk about it in the book, like, you know, there are businesses that you could build that provide a lot of, uh, you know, profits and good living for yourself, and you have complete, you know, control of what you do, but once you take on venture capital, there's almost a contract, uh, you're implicitly kind of getting into, which is, I'm gonna build a billion dollar company. This is this, I'm going to build something really scalable, really big. And I take that responsibility seriously …

AI assessment note: “Yeah, yeah, I mean, in, uh, 20, 24, early 24, so last year”

Q You went to Coachella with the Secret Service?

A I went when I was protecting Barbara, uh, Bush, which is George Bush's daughter. So I was her assistant detail leader. So I was the person who traveled with her, um, and I had a team. And so with her, the big thing was, because people didn't recognize her, when she was with Jenna, they were together, they knew the Bush twins, but when she was alone, she, you couldn't really tell. So to not draw attention to her, we would blend in. So if I'm going to Coachella, I'm not going to show up in my sunglasses and a suit, because right then and there, I'm drawing attention to her. So I would dress in a way where I was still tactically sound, but I blended in the environment for safety reasons.

AI assessment note: “I went when I was protecting Barbara, uh, Bush”

Q So if you had to give somebody a really tactical internet built list of things to read as a young man, what would those be? Like what would be the seven books that you'd be like, start here and then expand?

A So, you have to read Plato's Republic, and you have to do it, I'm convinced, with a tutor or in a group. I say this because I read it three times alone, in a corner, in a chair, after putting my kids down, and I was just, like, puzzling over it, and I didn't get quite as much out of it, right? And I'm, I'm a sharp guy, but, like, it's very hard to read these texts alone. So then I started going evening classes at St. John's College. I started doing tutoring with a guy named Mike Millerman, who people should check out. He's great. And that unlocked it for me. And why I say you gotta read that is that, you know, someone, I think, uh, maybe Bertrand Russell, I forget, but said, uh, all of, uh, philosophy is a footnote to Plato. And it's kind of right. Like these debates, he frames them really genuinely, really broadly. So I would say, read that. The next thing that I w that mattered a lot to me to read was a book called The Constitution of Liberty by Friedrich Hayek. And this is, I think, a good argument for why liberty is important. Like, you know, why freedom is something we cherish. He lays out an argument based on the usefulness of liberty. Particularly sacred is this essay called The Creative Powers of a Free Civilization. It's chapter two. And you can read that. It's like 16 pages or something. And that's wonderful. I would recommend Democracy in America. But it's very long.…

AI assessment note: “So, you have to read Plato's Republic... The next thing... The Constitution of Liberty”

Q You grew up on a farm and came from a lot of struggle and strife that only entrepreneurs know. Can you tell me about that time?

A Well, it was incredible to grow up on a family farm. And, uh, at the time, you know, I grew up in a house that had no upstairs heating. So we'd wake up in the morning in the winter and, and there would be frost inside the windows. And, but we, we never thought that was anything that, uh, would be different or wrong with that. We just had electric blankets that we slept under, but I saw how hard my family worked and I was inspired by it. I saw my grandmother writing the commodity futures prices on the Formica countertop. And then when my grandfather and dad would come in for lunch, they'd look at the prices and go back out. And that's where I first got my interest in finance and markets. And I saw my mom and dad building, uh, their trucking company together and dealing with the interstate commerce commission filings and the paperwork. And I saw our truck drivers coming over to collect their paychecks while my mom wrote them out and. It really impressed upon me that, wow, they're providing livelihood and they're building something for people that people are coming to us, asking them to haul grain, loads of grain off their farm, not just our farm, but theirs. And, uh, my parents sponsored our, the softball team in our small town, like I saw and what other small businesses did. And so I also saw how the toll it took on my dad, like How hard he worked, you know, 20 hour days plantin…

AI assessment note: “Well, it was incredible to grow up on a family farm.”

Q a lot of people to do less complaining, to have less negativity in their lives, you know, and Uh, I've heard you talk before about what to do when somebody is complaining, and it was totally counter to everything that I've thought to do when people are complaining. Can you tell me what do you, what do you do when somebody's complaining and you don't want them to keep going?

A When somebody is complaining, you want them to stop. The trick is to make them keep going. Because if you haven't heard the end of it, you haven't heard all of it. Meaning that there's a source of it that they haven't told you. You're only hearing the symptoms of it. Think of a, so I have a seven year old and a five year old. My daughter can complain about the food, about what she's wearing. She's, she doesn't want to do this. She doesn't want to do that. And she starts to whine. It's not about the food. It's not about what's going on. It's that she's tired. It's just like at your base need. Some people, we know this, me included, everybody, all of a sudden you feel grumpy, you feel irritable, you're just hungry. So there's always like this spot that the issue that you're voicing is really the issue. So when somebody is complaining to you, it's, what I like to say is, what else? There's one phrase that I like to use is what else? Because they will find something else, but then they kind of run out of steam. And then you transfer it. Once you feel like they're out of steam, because that's the, you gotta, you gotta let them out. You have to let them get it all out or they're not going to listen to you, period. And so as soon as they get it all out, it's this idea of, uh, What do you think we should do? As soon as you try to like start getting them to think of solutions, but make …

AI assessment note: “The trick is to make them keep going. Because if you haven't heard the end”

Q a ton of views, likes, shares, and you subscribe. So that I can have him back because I have about 452 other questions for him. So if you have questions for Robert too, put them down below. I promise you next time we'll go even deeper. Without further ado, the one, the only Robert Greene. Do you think best when you write or when you speak or when you read?

A Um, wow. I mean, uh, when I'm reading, I'm, I'm doing a lot of thinking, and I have a very active way of reading. I, uh, I take notes, and I write in the book, in the margins of the book, and if I don't like a book, which happens every now and then, I'm, like, crossing everything out, and I'm writing F you on the margins. I argue, and I talk with the book as I write it, but, um, you know, uh, when I'm talking, um, sometimes, um, I don't feel like I'm bringing my ideas as clearly as I'd like to. So I really think best through the form of writing, but, um, I've always handwritten my first drafts. Um, now I can only handwrite because I can't type. I used to be a very fast typist. Now I can't because of my stroke. So, um, I handwrite, and there's something about, because You know, you're, you're younger. People who are younger, they don't even know what handwriting is anymore. It's like something that, you know, from, from thousands of years ago, as far as they're concerned. But when you handwrite, there's a different feeling than when you type. There's more of a direct connection between the hand and the brain than the computer. So, I feel like when I'm writing, I'm kind of scratching on the page something that's in my ear that I'm hearing. It's, Getting a little bit hard to describe right now, but I'm actually going through that as I'm writing this chapter at home, which I'll be …

AI assessment note: “So I really think best through the form of writing”

Q 26, had a couple million dollars in real estate net worth. You know, making a couple 100,000 dollars a year to flash forward a year bankrupt financial struggle to six hundred million dollar office. I know you've, you've mentioned this before, obviously, but I think there's a lot of people that are more like the former you than the current you. What was that like back then? And what happened?

A Well, we were, um, uh, I got my degree in real estate, and I sold my first house three weeks after I turned 18 years old, so I've been in real estate my whole life. Mom and Dad were in the business, and so when I got out of college, I bounced through a couple jobs pretty quick, and then started buying and selling houses, and I was doing Flip This House before there was cable TV or Chip and Joanna were born, you know, and so it was a long time ago. This is in 1984, right? So, um, but I was good at it. I'm always good at making a deal, and math is easy for me, and that Kind of stuff, so I would, and I hustled, and so I bought, started from nothing. We ended up with about four million dollars worth, a little over a million dollar net worth, and I'm making a couple hundred a year at, at 24 years old in eight, 1984, but I'd borrowed too much money, and I had a lot of short-term notes. The bank got sold to another bank, and a guy in another city looked down and said, there's a kid, 24 years old, owes us a million dollars. This is crazy, and they said, let's limit this relationship, which is banker talk for ruin his life. They called them, Um, and that started a snowball, a bad snowball. That took two and a half years to unfold, and we were bankrupt at the end of it with a brand new baby, a toddler, and a marriage hanging on by a thread. So, like my old pastor used to say, a man with …

AI assessment note: “I'd borrowed too much money, and I had a lot of short-term notes.”

Q Until you realize how to get other people's capital. So, like, if somebody was asking you, like, Ankur, right now, I need to get rich people's money in order to build this thing, what would you tell them?

A I think you have to, for what worked for me was I had real fucking skin in the game. So what most people don't understand is they look at a venture fund, venture funds charge two and 20, right? Which is two percent management for your 20% carry, which is the take of profits. What people don't understand is it's actually closer to 20 and 20. It's one of the best kept secrets because venture funds charge those fees for 10 years. So if you raise a hundred million dollars, The investor makes twenty million bucks, maybe even 25, regardless of how the fund does. What I did with my fund is I took zero management fees, which was absurd for a fund of that size and a quarter of all the capital was mine. So yes, the notion doc is important. Yes. Like the mechanism is important, but end of the day, people saw I had real skin in the game that it became much easier for them to say yes.

AI assessment note: “what worked for me was I had real fucking skin in the game.”

Q That's a great line. What do you mean by that?

A So when I was 19 years old, 20 years old, I was in college. I had the chance to meet, you know, Marc Andreessen, Naval Ravikant, like all these, like, people that were iconic and I looked up to, and they all took me very seriously, almost as a peer. Like, what are you going to build? Like, this sounds so great. Contrast that with when I went to India and I tried to meet with the CEO of a couple of smaller companies. Would condescendingly ask where my parents were, right? It's such a different attitude, and I think San Francisco and Silicon Valley knows that young people have historically done incredible things, so young people are taken very seriously.

AI assessment note: “I think San Francisco and Silicon Valley knows that young people have historically done incredible things”

Q Yeah, exactly. I mean, people wouldn't believe that except that you have arguably one of the most popular classes, if not the most popular elective at Harvard, which is actually about love and happiness, right? We were talking before and, you know, I think, is it true that one of the keys to happiness is love?

A Happiness is love. So it's almost a, it's almost an identity. It's, it's almost a one-to-one correspondence is what we actually find. So yeah, the, so the class that I teach at the Harvard business school is called leadership and happiness, and it's an MBA class. Um, it's a very popular elective. It starts actually, um, we're taping this a week and a half before the class actually starts, so I'm, I'm, you know, developing. Every year I develop it new, and I'm looking at the roster, and it's completely jammed. I have, you know, 400 on the waiting list or something like that. It's a, it's a thrill to actually do it. But the main point that I tell them is that really it comes down to happiness at the end of the day. Getting greater happiness really has everything, the hygiene, the technique has everything to do with the love in your life is what it comes down to. Um, I'll give you an example. So there's this 85 year longitudinal study called the Harvard Study of Adult Development. You've heard about it before. It's been, Harvard researchers have been fielding a survey with the same sample of people for 85 years. So they can see what are they doing, how happy are they, how healthy are they, how are their relationships, et cetera, et cetera. And it's a good representative sample. Started off as just Harvard students in the late 19 thirties. Um, and it contained, you know, JFK was in…

AI assessment note: “Happiness is love. So it's almost a, it's almost an identity.”

Q really like that. You also said this, uh, this quote that I loved, um, which was, Every single thing you do today is something that your 90 year old self will wish they could go back and do. The good old days are happening right now. I was wondering for you, since most people never think about time, you think about it a lot. When did that flip and why?

A In 2021, I had a single conversation that changed my life. I was out for a drink with an old friend, and we were just catching up, and he was asking how I was doing, and I had spent the last seven years of my life rising through the ranks in the finance world. I was working 80 to a hundred hours a week. I was making more and more money, and thinking that that was how I was going to reach the land of success and happiness, and a lot of other areas of my life had started to suffer, namely I was living very far away from my parents, 3000 miles away, and they were getting older. And so my friend asked how I was doing in this moment, and I said that it had started to get tough being so far away from my parents. They had started to show chinks in their armor, if you will. They were mortal. And he asked how old they were, and I said mid-sixties. And he said, how often do you see them? And I said, maybe once a year. And he looked me in the face and just said, Ok, so you're going to see your parents 15 more times before they die. And I remember feeling like I had been punched in the gut. I mean, the idea that the amount of time you have left with the people that you love most in this world is so finite, so countable, that you can put it onto a few hands, shook me to my core. And in that moment, I recognized that Something had to change that if we didn't make a change, I was going to wak…

AI assessment note: “In 2021, I had a single conversation that changed my life.”

Q And then I realized this is the thing about you, like, you sort of have this ability, I think, to get really big, powerful people to quote unquote mentor you without being annoying, right? And I think a lot of people today are like, I want a big mentor, or how could I get somebody like Tim Cook to care about me? How did that relationship start? Tell that story.

A Uh, yeah, so I met Tim for the first time, um, In 2014, when I first started working, I just graduated from Stanford, and I took a job working in private equity. I was going to work 80 to hundred hour weeks, and that was the job. That's what it was going to be. And so I knew if I wanted to work out, I was going to have to go early in the morning. And that meant getting to the Equinox in Palo Alto at four 45 in the morning every single day. And that meant I had to get up at 3:45 and like wake myself up and be at the gym at four 45. It turns out that There aren't that many people that are willing to get to the gym at four 45. So there was a group of like eight of us that would show up every single day at that time, like waiting for them to open the door. And you would talk to those people cause you were with them every single day. So six months go by and I'm like talking to all these people early in the morning. And I was having a conversation with one guy and I walk away and someone comes up to me and is like, do you know who that is? That guy you were just talking to? And I was like, I don't know. That's the guy, like one of the guys that's here. And he goes, that's Tim Cook, the CEO of Apple. And I was like, oh shit. Cause I've probably been saying the dumbest stuff to this guy for the last six months. And look, I wasn't in tech, so it wasn't close to the space. I didn't know …

AI assessment note: “I met Tim for the first time, um, In 2014”

Q talk really quickly about some of the frameworks I've stolen from you to make my life better, easier, simpler, a little richer and wealthier. Um, you kind of popularized this idea for me around razors, like a rule of thumb that simplifies decision-making, but you have quite a few of them. Can you explain what it is and what are some of your favorites and how do you use them?

A Yeah. Um, so the idea of a razor comes from philosophy originally. It's, it's, Something that allows you to shave away, uh, possible explanations and get to the heart of something. So the best way to say it is what you said. It's a rule of thumb that simplifies decision making. The most famous razor, which is probably my favorite one, uh, is Occam's razor, which is the idea that the simplest possible explanation is often the best one. So this is for all the conspiracy theorists out there. I'm sorry. Uh, but Occam's razor typically will say that Uh, if there is some, you know, crazy thing happening, and we want to say that the government is doing some whole, like, crazy back-end, you know, crazy thing, the simplest explanation is like, uh, no, it's just the obvious thing that is happening. Uh, the government is not particularly competent. If you have ever flown, uh, you have seen the government in action with the TSA, or if you have ever gone to try to get a new license, uh, you have seen it at the DMV. That's the government. Uh, but, uh, all jokes aside on that, Occam's razor is amazing because it's all about the idea that simple is beautiful. And so, uh, whenever you have a simple explanation for something or a very complex one that will require a lot of assumptions to be true, usually the simple one is correct. Another one of my favorites for the world of the internet is Hanl…

AI assessment note: “The most famous razor, which is probably my favorite one, uh, is Occam's razor”

Q What exactly is tactical empathy and why does it matter?

A Um, it's effectively proactive listening based on patterns of behavior that are predicted by things like your five core emotions and neuroscience. Now originally, um, empathy was originally designed to not be sympathy. It's been contorted, convoluted into usage. These days people say if you have empathy, that means you sympathize, you have compassion. Empathy is just observing the other person's Emotions. And where it's you getting out of the way. Um, empathy, uh, from an Israeli to a Palestinian is for the Israeli to say, you hate us because you think we're a colonizing power that's bent on your extermination. That's not agreement. That's observing the other side's point of view. Palestinian to an Israeli. Uh, the world persecuted you. You feel that this is your homeland, which is taken away from you 2000 years ago. Ultimately, there was a global effort to exterminate you perpetrated by the Nazis in the 19 thirties. Most of the world stood back and watched. And then finally, you had, after all these years, you finally have a homeland, and this is the only place you feel safe. There was no agreement from either side on that. That's empathy. That's stating the other side's perspective. And that's the true application of empathy. We call the tactical empathy originally because it's a little why you tell a SEAL guy, no, we're not teaching you yoga breathing. We're teaching you tac…

AI assessment note: “it's effectively proactive listening based on patterns of behavior”

Q So did you just, have you always been the type of person who just kind of ignores when people make fun of you or think that something you're doing is goofy?

A No, no. When I was a kid, I was super overweight, and so I got bullied pretty significantly. Um, but I think that kind of like gave me a pretty thick skin early on. Um, and I mean, I ended up losing all the weight, which was great. I lost like a 140 pounds when I was like 16. So, you know, In a weird way, they kind of pushed me to do that, so it's hard to, I, I regained this new perspective where I was like, I mean, you know, they were mean to me, and they made fun of me, and I'm not saying it was right, and the way they went about it was way, way, way not okay, and I don't condone bullying, but It did push me in a direction that changed my life, which made me realize, oh, I can, like, literally just change something in my life and make good things happen for myself if I'm willing to put in the work. Ok, cool. And that attitude stuck with me from that moment forever. So the whole, like, people saying negative things about me kind of was this wash after that.

AI assessment note: “No, no. When I was a kid, I was super overweight”