There’s Always A Way: Alex Banayan on The Third Door

The day before his freshman year final exams, 18-year old Alex Banayan hacked The Price Is Right, won a sailboat, sold it, and used the prize money to fund his quest to learn from the worldʼs most successful people. Over the next seven years, he pursued a graduate degree in persistence and perseverance from the University of Life. He snuck into Warren Buffett's shareholders meeting. He chased Larry King through a grocery store. He celebrated with Lady Gaga in the hottest nightclub. Along the way, he landed remarkable one-on-one interviews with Bill Gates, Maya Angelou, Steve Wozniak, Jane Goodall, Quincy Jones, and many more. Alex's major discovery? Each and every icon shared one thing in common: they all took something he calls The Third Door*. Since that fateful day on the Price Is Right, Alex went on to become the world's youngest venture capital executive, a coup that landed him on Forbesʼ '30 Under 30′ list and Business Insiderʼs ‘Most Powerful People Under 30.' He has delivered keynotes at prestigious organizations like Apple, Nike, IBM, Dell, MTV and even Harvard. He has contributed to publications like Fast Company, the Washington Post, Entrepreneur, and TechCrunch. And he has been featured everywhere from Fortune, Forbes, Businessweek and Bloomberg to Fox News, & CBS News. This week, Alex's new book chronicling his wild seven-year adventure — aptly entitled The Third Door* — hit bookstores everywhere. I first met Alex about 6 years ago. Just 19 at the time, he was in the very early stages of putting his book together. I liked him instantly, and left our lunch impressed with his rare mix of precociousness, infectious enthusiasm and raw authenticity. We stayed in touch. And that day I made him a promise: should he ever finish his book (something I doubted at the time) that he had an open invite to share his story on the podcast. Today I honor that promise. This is a conversation about one young man's determination to find his way in the world. It's about a quest to learn what cannot be taught in the confines of a classroom. It’s about never giving up. And it's about always finding a way. But most of all, this is a very personal exchange between two friends about what it really means to pursue a dream. Peace + Plants, Rich Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Rich Roll?

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• 1:05Speaker 01

  Someone mentors you for three reasons, and they're all subconscious reasons. One, they see some of themself in you. Two, they want to help you be more like them, whether it's because they have a special expertise they want to help you with, but they want to help you, and they feel they can help you be more like them. The third one is the most interesting. They want to be more like you. And that's sort of confusing, but if someone's a 70-year-old CEO, sometimes the thing they need most in their life is 19-year-old enthusiasm about their company.

• 1:42Rich Roll?

  That's Alex Benayan, and this is the Rich Roll Podcast.

• 2:00Rich Roll?

  Let's say for the sake of argument, as a thought experiment, that you have an idea, you have a goal, perhaps it's even a dream. Well, right now, it's just this thing that's swimming around in your head. Making it real, well, that's a different story altogether. And making it a success is a completely different ballpark. It's something that at times can be so challenging that, quite frankly, most people end up abandoning it long before capitalizing on the opportunities presented. Not necessarily because of lack of will, but because they fail to see what this week's guest, Alex Banayan, calls the

• 2:39Rich Roll?

  third door. Let me explain. Alex analogizes it like this. Life, business, success, it's all just like a nightclub. There are always three ways in. There's the first door, that's the main entrance. That's where the line curves around the block, where 99% of the people just wait around, kind of just hoping to get in. Then there's the second door. That's the VIP entrance, where the billionaires, the celebrities, the people who are just kind of born into this kind of thing, slip through. But what no one really tells you, what really goes unaddressed, is that there is always, always a third door. It's the entrance where you gotta jump out of line, you gotta run down the alley, you gotta bang on the door

• 3:23Rich Roll?

  100 times, crack open the window, and sneak through the kitchen. In other words, there's always a way, a way to more creatively approach and tackle the obstacles that inevitably stand between you and the actualization of your goals and your dreams. My name is Rich Roll, this is my podcast, and today I explore this idea and much more with my young and quite enterprising friend, Alex Banayan. Alex is a guy who is wise well beyond his years. He's a really cool dude with a rather amazing and inspirational personal story that I think you guys are going to enjoy very much. As always, there's a couple of

• 4:07Rich Roll?

  things I want to say about Alex and this conversation before we dig in. But first,

• 4:20Rich Roll?

  So where to begin with Alex Banayan? Well, this is a guy, just to kind of paint the picture, a portrait of who this young man is. The day before his freshman year final exams, freshman year in college, rather than study like all his friends and peers, Alex decides to instead test his luck by going on the television show The Price is Right. He ends up figuring out, he kind of figures out the system so he can win. He wins a sailboat, he sells it, and he uses the prize money to fund this harebrained crazy quest that he had to go on a journey to learn from the world's most successful people. And that adventure becomes the basis of a new book that he spent the last seven years

• 5:05Rich Roll?

  writing entitled, I think you guessed it, The Third Door. And since that kind of fateful day on The Price is Right, Alex has gone on to accomplish many things. He became the world's youngest venture capital executive. That was a coup that landed him on the Forbes 30 Under 30 list, as well as Business Insider's Most Powerful People Under 30. He has delivered keynotes at all kinds of prestigious organizations like Apple, Nike, IBM, Dell, MPV, even Harvard. He's contributed to publications like Fast Company, The Washington Post, Entrepreneur, and TechCrunch, and he's been featured basically everywhere, everywhere from Fortune, Forbes, Businessweek, and Bloomberg to Fox News and CBS News.

• 5:48Rich Roll?

  On a personal note, I first met Alex, it had to be more than six years ago at this point, when he was in the very early stages of putting this book together. I think he was like 19 at the time, and we kind of go into this in detail on the podcast, so I don't want to get too much in the weeds here. But I just remember him being this super impressive young man, this kid who had a very rare mix of precociousness, but also like authenticity. And I just liked him instantly. We stayed in touch, and I distinctly remember telling him that if he ever finished that book he was writing, that he had an open invite on the show.

• 6:27Rich Roll?

  And I will admit to periodic doubt that he would indeed ever finish it, but finish it he did, and today I honor that promise. So. This is a conversation about many things. It's about one young person's efforts to find his way in the world, to really learn what he couldn't access in school. It's about persistence and perseverance and really never giving up and always, always finding a way to actualize your dreams. But mostly, it's two friends talking about what it means to pursue a dream. Here's Alex.

• 7:07Rich Roll?

  It's great to see you. Thanks for coming out to do this, man. I'm really excited for you. This has been a long time coming. I think I said to you like six or seven years. Like, at the very beginning of the podcast, I was like, "Well, let me know when the book's done and, you know, come and tell me about it." And I was like, "I wonder if that guy's ever gonna finish that book."

• 7:25Speaker 01

  Every time we've seen each other, you're like, "So, how's it going, Alex?"

• 7:31Rich Roll?

  Was I that dire? No.

• 7:33Speaker 01

  That tone came off to me because inside, for me, I was drowning, you know? Because it's been seven years.

• 7:40Rich Roll?

  I can't believe you've been working on this book for seven years. So, just to kind of lay the foundation for this, I remember, this is how we sort of first connected and met. My editor on Finding Ultra at Crown is an amazing guy called Rick Horgan, who we can talk about because he deserves to be recognized.

• 7:59Speaker 01

  He's incredible.

• 8:00Rich Roll?

  And I was having a phone conversation with him. I can't even remember whether Finding Ultra had even come out yet. Like, it was probably sometime in 2012. And he's like, "Hey, I'm working on this book with this young guy. He's really cool. I think you'd really like him. Like, I want to connect you guys. Like, this is gonna be a really cool book." And that's when your name first came up. And we had lunch. I can't remember when that was, but all I know is it was a long time ago. Yeah. And you told me your story, which I thought was amazing, and this book that you were working on. And then, we would bump into each other once or twice a year, and I'd be like, "How's the book going?"

• 8:44Rich Roll?

  And you know what's funny is that I know other people who get stuck in this kind of situation where they're working on a book and it gets protracted and a lot of them don't end up finishing it. So I was like, I wonder if maybe he's never going to finish this book. Like, I don't know what's gonna happen here, you know? So here we are. It's coming out in June.

• 9:04Speaker 01

  Thank God.

• 9:05Rich Roll?

  I'm proud of you. I feel very emotionally invested in this journey that you've been on. So it's really cool to be able to talk about it today.

• 9:12Speaker 01

  Thank you for all the encouragement along the way.

• 9:13Rich Roll?

  Yeah, it's great. I mean, we, so Rick Horgan was your editor on this book. And just so people understand, like, when I first pitched Finding Ultra, like, when you, when you write a book, you write a proposal, I'm sure you did this as well, right? And then, and then my book agent sent it out to a couple of publishing houses, and she was very tempered with me. She's like, listen, you really got to thread the needle here. You have a good story, but like, you know, it's really tough out there. And like, you know, I'm gonna do my best, but I'm just not sure. And then we got a bite with Crown. She's like, we got a call with Crown. And it was my very first, like, pitch over the phone. I'd never done anything like that before. And he's like, you're gonna have like 10 minutes or five

• 9:58Rich Roll?

  minutes on the phone with this guy. Like, you gotta sell yourself. So we did this call. And I remember I was like, at the Calabasas Commons, it's like outdoor mall down the street here. And the service was not very good. And I had, I like hid behind a bush to like, do this call to like, make sure there wasn't any kind of like noise. And I was like crouched down and did this call. And it went well. And he ended up like bidding on the book. He really wanted the book. And we ended up selling Finding Ultra to Crown. And I remember saying to my book agent, I'm gonna bring this around to you, don't worry. I remember saying to my book agent, Yeah, but this guy Rick Horgan, like, he's not actually gonna be my editor, right? Like, they're gonna assign me some kind of junior person because this guy, Rick Horgan,

• 10:42Rich Roll?

  who I later found out, I would have panicked on the phone had I known this during the call, had like edited, you know, Hillary Clinton's biography, like, he was the editor on like huge books, you know, and I was like, yeah, I'm like, this guy's way too senior and important to be interested in what I'm doing, you know, I was like, no, no, no, he's gonna be your editor. And we had this amazing collaboration, and I learned so much about the art of writing and storytelling, and he really pushed me. And I remember at one point, he said to me, he goes, listen, here's the little secret, dirty little secret about New York editors and the publishing industry, editors don't really edit, because they have too many books. So you have this romantic idea that you're gonna have this amazing relationship with

• 11:26Rich Roll?

  this editor, and you're gonna be on the phone with him at midnight, having these conversations about philosophy, you know, and it's like, it doesn't work that way. And he was basically saying, like, I don't have time to really even read everything that's coming across my desk that I'm responsible for, but I really like your story, and I really wanna help you, and I wanna make this book the best that it can be. And he really did roll up his sleeves, and he really helped the book become the book that it became. Like, I couldn't have done it without him, and I'm just forever grateful to him. And so I'm interested first, and I would imagine you had a similar relationship with him.

• 12:00Speaker 01

  Yeah, you nailed it. When I first met Rick, so I've been through three different, because I've been working on this for seven years, and turnover in the publishing industry is very high now, I've gone through three different editors.

• 12:13Rich Roll?

  Right, cuz he left Crown.

• 12:15Speaker 01

  He left Crown. But he was my original editor.

• 12:17Rich Roll?

  Right.

• 12:18Speaker 01

  And the thing Rick did that changed my life, and I really mean that, is when I had originally started this book, it was a book about, in my head, you know, I'm this 18-year-old kid, I'm gonna go interview all these people who I admire, figure out how they launched their careers, and each chapter's a different person, you know, chapter one is Bill Gates, chapter two is Warren Buffett, and that was my thinking.

• 12:44Speaker 01

  About, so it took two years until I got the deal with Crown. And then a year into the deal, Rick calls me into his office and you're gonna appreciate this. He calls me into his office and he has that like gruff New York voice, right? And he's like, Alex, what's the goal of this book? You have to understand, this is a year into me working with him.

• 13:05Rich Roll?

  Like, what do you mean, what is the goal? Thought we were clear on that.

• 13:07Speaker 01

  It's a very strange question again. And he's like, what's the, what's the goal? Is it to change people's lives or to inform them? And I'm like, well, that's clearly a leading question. Yeah, I want to try to change lives. And he goes, well, the book you're writing isn't gonna do that. And I'm like, we've been working together for a year. How, how are you bringing this up just now? And he's like, well, I have a son your age, you wouldn't have listened. And essentially what he told me is that if you look at any magazine Q and A, you know, there might be great information in there, but it's never changed a life. But if you look at all the stories, and we actually talked about this in our first lunch, I don't know if you remember, but the stories that changed lives are this same story arc.

• 13:51Speaker 01

  You know, there's this person who everyone can relate to. And as, you know, she or he goes on this journey and evolves, so does the reader. And that's how you change someone's life.

• 14:04Rich Roll?

  Yeah, I do remember having that conversation with you. And I think that's one of the reasons why he suggested that you read Finding Ultra, because one of the things that was sort of core and key. I mean, look, my book is about my story. It's different than your book, but, but I think what he was trying to convey to you is you have to get people emotionally invested in, in what you're doing here. And if it's too dry, if it's just informational, you're never gonna have that connection. So people aren't, aren't gonna be as engaged with the material as they could be. They need to see it through your eyes and your experience. So to the extent that you can invest yourself in this story and make your journey core to that narrative, the better off you're gonna be in that quest to transform lives. And, and you've accomplished that. I mean, that's ultimately what you ended up doing in this book.

• 14:48Speaker 01

  Right, and it took me really like at least three months. Cause I think when we had first spoken, I was in that three month period of like, Awkwardness of not knowing if I was going to follow Rick's advice or not. Because I had spent years saying I was not going to even use my name in the book. Like, this wasn't about me at all. And what Rick had to, you know, drill in my head-

• 15:09Rich Roll?

  Writing a textbook?

• 15:10Speaker 01

  Essentially, and he helped me realize, look, it's not about you, literally. You're a conduit for the reader.

• 15:18Rich Roll?

  Mm-hmm.

• 15:18Speaker 01

  And that's how the book is now.

• 15:20Rich Roll?

  Right, you have to be a cipher. You have to be a stand-in for the audience member. Yeah, cool. So, let's, uh, let's talk about how it all came together. I mean, your story's so crazy. Like, how old were you when I first met you? Twenty-three or something like that?

• 15:35Speaker 01

  I had just turned 20 when you and I first met.

• 15:37Rich Roll?

  You were just, you had just turned 20?

• 15:39Speaker 01

  So I'd been working on the book for about two years.

• 15:40Rich Roll?

  Right. All right, so backing it up from there, well, let's go all, all the way back. Um, you grew up in Los Angeles.

• 15:48Speaker 01

  Uh-huh.

• 15:48Rich Roll?

  Uh, Iranian Jews. Your grandfather, uh, was living in Iran. Like, I, I love this story about your grandfather. Because I think that, I, I feel like you're, you share a lot of DNA with him. And I feel like that part of your story kind of informs your ethos and perspective on business and life.

• 16:09Speaker 01

  So, and it's so funny, because I didn't know this story until much later in my life. When I was a kid, it was sort of kept secret from us. To fully understand who I am, you actually have to go back, like you said, to, you know, 90 years ago, when my grandfather was born. And he was born in Persia, in Iran. He was the youngest of six siblings, so five older siblings. Boy, four girls, and then him.

• 16:38Rich Roll?

  Uh-huh.

• 16:39Speaker 01

  And when my grandfather was three years old, his father passed away. And the thing you have to know about Iran at that time is that women weren't really allowed to work. So it was up to the men in the family to provide. Thankfully, there was an older brother, and he was about 18, so he started working and taking care of the family. And then two years after that, the older brother dies.

• 17:02Speaker 01

  So now, the only male left in the family is the five-year-old. Child, my grandpa. But the mom, thankfully, was very wise and she said, "Look, you're going to school and I'll find ways to make ends meet." So she's selling, you know, her wedding ring, she's selling the vase in the living room. She's just making things work, barely, you know, putting food on the table. And by the time my grandpa was about eight or nine, he realized, "This isn't very sustainable." So he was flipping through the newspaper one day and in, I think it might have been the classified section, he sees a order from the Iranian government asking for paint thinner for a government building.

• 17:44Speaker 01

  And he's like nine years old and I think he was like an apprentice at a local shop. So he knew like what a, you know, an assertion order is. So he, he like gets out the bid and he just, but because he's nine, he doesn't know how much the cost of these things are. He fills it out and sends it in and because he gave such a low bid, he, he won the contract.

• 18:04Rich Roll?

  Right, because they don't know that he's nine.

• 18:05Speaker 01

  No, no, we're on the form to say, "How old are you?"

• 18:07Rich Roll?

  This bid looks good.

• 18:10Speaker 01

  You know, his handwriting must have been fine. So, you know, he wins this bid and he's nine years old, has no idea what to do. So he, you know, goes to the bazaar and has this, you know, family friend who has paint thinner and he's, you know, gets the paint thinner from this guy, gives it to the government, makes a profit. And he even remembers like buying like pistachios on the way home and it was like this big bag of pistachios and he was like the happiest day of his life. A couple of weeks later, he's in geometry class and he's in like elementary school.

• 18:41Rich Roll?

  Right.

• 18:42Speaker 01

  And the police show up in his class and they pull him out of class and they say, "The paint thinner you gave us is expired and if you don't get us new paint thinner, you're going to have a serious problem." And Iran, especially when you're a Jew in Iran, when the police are saying, "You have a serious problem."

• 19:00Rich Roll?

  They're literally going to arrest and imprison this elementary school kid.

• 19:04Speaker 01

  They don't give a shit. And...

• 19:08Speaker 01

  It's, yeah, it's so wild because what he ends up doing is he goes back to that family friend and says, hey, the paint thinner you gave me is expired. And he goes, that's your problem, not mine. So now my grandpa has to go, you know, this young little Jewish boy in this, you know, bazaar in Tehran, ends up finding another paint thinner dealer, uses his profits to buy that paint thinner, gives it to the government and is home free. But that sort of sets him on this track of, you know, doing more orders for the government. And he starts getting better at it and better at it. In the meantime, he's getting his, you know, PhD in chemistry. And by age 50, he had done really well for himself. He had one of the,

• 19:50Speaker 01

  you know, tallest buildings in the, you know, nation's capital, you know, working on the top floor. And at age 50, he had four kids, my mom included. And right around then, the Iranian revolution happens. And they did something very ingenious, very cruel, but very ingenious, which is before the revolution literally started, they sort of created this list of influential Jews that they needed to take out to make it much easier to have the revolution. And my grandpa was on that list unknowingly. So he's in his office one day, and it's still crazy to hear him tell this story because he doesn't do it

• 20:31Speaker 01

  often. But to my understanding, you know, loads of men with like, you know, masks over their head, break in through the ground floor and surround the building, go up all the staircases, to the point where he knew, like through a telephone system, that they were coming. And he had like 30 seconds, but all the staircases were covered. And, oh, there's one part of the story that's crazy, which is, he got his passport and like threw it into an air, an air conditioning vent, and told his assistant, who is Muslim, look, they're not going to get you. They're only here to get me, like recover my passport in case I find a way out. And

• 21:14Speaker 01

  You know, my grandpa gets captured at gunpoint. Um, they put like a bag over his head and take him to this compound, which is essentially an execution compound. And even to this day, when I ask him about the scariest time, he's been through a lot. And when I ask him about the scariest time in his life, he said it was there because every night you would hear gunshots and a different person who's being held doesn't come back. So you figure out very, it's not like they're reading you Miranda rights. You're just held there.

• 21:45Rich Roll?

  Yeah, yeah, yeah. So you're just, you're counting down until you're the person who's picked.

• 21:48Speaker 01

  Yeah, and you know, my grandpa is trying to find a way out of this thing. He's trying to, you know, talk his way out, offer bribes, like nothing. And soon enough, over the speaker, they call his name. And they put a bag over his head and, you know, walk him down this corridor. And when the bag comes off, he's out of the compound. One of the guards had taken the bribe. And my grandpa, you know, escapes Iran during the revolution, makes it to America as a refugee.

• 22:19Rich Roll?

  Wow.

• 22:20Speaker 01

  And sadly, actually has to go back to where he was 50 years ago, you know, with nothing, having to rebuild a life. Except this time, he has a wife and four kids.

• 22:28Rich Roll?

  He brings, he's able to bring his family.

• 22:30Speaker 01

  Yeah.

• 22:31Rich Roll?

  And so that's how your parents.

• 22:32Speaker 01

  So that's how my mom, my mom came here as a teenager, um, through the revolution. So my grandpa, again, just, I think 12 failed businesses in America before he started this random spectrophotometer company and, you know, has rebuilt his life. But what that story really shows me is that it's just this incredible story of possibility, which is he started out in this unbelievably dire situation, built himself up and was taken to the darkest place that I can't even. Understand and was able to come out the other end.

• 23:11Rich Roll?

  Mm hmm.

• 23:12Speaker 01

  So that's really what I've taken from my grandfather.

• 23:14Rich Roll?

  The perseverance, but also like this guy, I mean, what he was doing in elementary school, like that's just built into his, the fabric of his DNA is like a little Gary V hustler, you know, like, you know, right out of the womb. And I see, I see aspects of that, elements of that in, in your, in your path.

• 23:35Speaker 01

  I appreciate that, man. Thank you.

• 23:36Rich Roll?

  You know what I mean? Like, I think you're, you're carrying part of your grandfather with you. I mean, is he still around?

• 23:42Speaker 01

  Yeah. You know what the craziest thing? He's still around. He's 92 and still goes to the office. He doesn't know another way to live.

• 23:50Rich Roll?

  Yeah.

• 23:50Speaker 01

  He's never taken a vacation.

• 23:53Rich Roll?

  Yeah.

• 23:54Speaker 01

  It's wild.

• 23:55Rich Roll?

  Well, I would imagine part of that is, you know, when you've suffered to the extent that he has and lost it, like there's a connection with holding on to it or continuing to grow something that's probably a little bit more deep than we can understand.

• 24:09Speaker 01

  Yeah. What he's been through is, like you said, it's very hard to understand.

• 24:12Rich Roll?

  Right. So your parents really grow up in the United States or this is, so your grandfather was on your mom's side.

• 24:20Speaker 01

  Yeah. So this is my mom's dad. My dad came when he was about 19 and my mom came when she was about, you know, 10 and they met here. And it's, you know, I can't fathom what life would have been like if I went through what they went through as teenagers, you know, leaving your entire, every, and they didn't come here thinking they were refugees. They came here thinking they were coming for a two month vacation as the riots calmed down back at home.

• 24:49Rich Roll?

  And then they would go back.

• 24:51Speaker 01

  They had all their stuff. They're like, oh yeah, just pack a day bag. We'll be back in a month or so. And they just never been home ever since.

• 24:58Rich Roll?

  Right, right, right. So how does that inform like their worldview? And how does that worldview trickle down into the expectations placed on a young Alex Banayan?

• 25:10Speaker 01

  Well, so how that affected their worldview, whether they knew it or not, was I grew up in a family where like fear was in the walls and

• 25:19Rich Roll?

  Understandably.

• 25:21Speaker 01

  Not to an eight year old Alex. I'm just like, why won't my mom let me sleep over at a friend's house? Why won't my mom like, let me go on a field trip like without her physically driving like?

• 25:34Speaker 01

  It was crazy. Um, like even school trips were giant debates in my family. Because there was just this tremendous amount of trauma that my parents had gone through.

• 25:47Rich Roll?

  Yeah, and a betrayal of trust too. Nobody's safe. Who to trust? You know? You're gonna get on a bus and go across town.

• 25:54Speaker 01

  Right, with the school, the government-funded school. And of course, like as a kid, I had no comprehension.

• 26:02Rich Roll?

  What are you talking about?

• 26:03Speaker 01

  I'm like, we're just going to Yosemite, let us go. And they're like, with my younger sister, my mom was, my mom followed the bus. I've never told anybody this, but you know, it's a testament to my mom's love and also to the the trauma they went through.

• 26:19Rich Roll?

  Yeah, but she came over at 10. Does she remember what her dad went through? Or is that a memory that she can't access?

• 26:27Speaker 01

  It's in your blood, you know, when you're, and there's a certain amount of shame too with it because when I was growing up, I would look in family photo albums and see my grandpa wasn't in pictures for like a year period or two-year period. And I would ask where he was and they would say, "Tudan ishka bu de," which means he was at the university. It wasn't until I was 18 I found out he was actually at Dev Camp.

• 26:51Rich Roll?

  They weren't even telling you what it actually happened.

• 26:53Speaker 01

  No, so it was almost this like skeleton in my family's closet that my grandpa was held to be executed.

• 26:58Rich Roll?

  It's hard to understand why that would create shame though. It certainly wasn't, you know, by any fault of his.

• 27:05Speaker 01

  You, you have to spend more time with Persian Jews. Does everything create shame? It's like, oh, the way I poured my water, it's very shameful.

• 27:16Rich Roll?

  Hang your head low, Alex. All right, so, so you come out of the womb though and they're like, this kid's gonna be a doctor.

• 27:23Speaker 01

  Yeah, because, again, I, exactly, I came out of the womb, my mom cradles me in her arms and stamps MD on my ass and sends me on my way. And that's what happens when you're the son of, you know, these Persian Jewish immigrants where, and I have a bunch of friends who I grew up with who went through the same thing. Because...

• 27:41Speaker 01

  And this is something my grandma would tell me. In a revolution, they can take your money, they can take your possessions, but they can't take away what you know. And if you're a doctor and you can save people, no one can take that away from you. So me being a doctor as a kid, wasn't this like amazing fun fantasy. It was like, it was a very focused, cemented life track. I wore scrubs to school for Halloween. I went to pre-med summer camp at high school. And by the time I got to college, I was like the pre-med of pre-meds. And it wasn't until the first month where I was living in the dorms that I wasn't surrounded by my parents, my grandparents, and this weird phenomenon happened.

• 28:25Speaker 01

  All these things that in my entire childhood were my identity, started sucking the life out of me. I remember looking at this like towering stack of biology books, feeling like they were like the mentors, totally sucking the soul. And at first I assumed, maybe I'm just being lazy. And that's when I started to wonder, well, what if I'm not on my path? What if I'm on a path somebody placed me on and I'm just rolling down? And thus ensues like this life crisis of, it wasn't about switching a major as much as it was changing my identity.

• 29:04Rich Roll?

  Right. And prior to that, I would imagine you didn't spend a lot of time really contemplating what makes you happy, or what would be fulfilling for you.

• 29:13Speaker 01

  I don't even know those questions existed.

• 29:15Rich Roll?

  Yeah, yeah, yeah.

• 29:16Speaker 01

  There's no discussion of happiness in an immigrant family.

• 29:19Rich Roll?

  Yeah. I mean, my, my, you know, my rearing is very different than yours, but you know, I can relate to that. Like I was, you know, in a somewhat analogous situation and it took me a lot longer to have that kind of dawning epiphany that you had much earlier. But I understand on some level, you know, what that's like. And, and, and, you know, coming up in this family where shame was very much a part of the, the sort of, you know, family ethos.

• 29:45Speaker 01

  It's not a part of it, it is the family ethos.

• 29:48Rich Roll?

  Like, is there anything more shame provoking than confronting the fact that you may not want to pursue this path that you've been on your whole life? And what would that look like, you know, in terms of communicating that to your parents?

• 30:03Speaker 01

  Oh my God, it was terrifying because when I first started even questioning what I wanted to do with my life, going through that life crisis, I couldn't tell my parents I was even questioning it. So it was almost like I was living this double life where my mom would call me and ask how my pre-med classes were going. I'm like, "Oh, it's great!" Then I would like hang up on her and like sneak the four hour work week under my like blanket and read it.

• 30:26Rich Roll?

  Were you still enrolled in the pre-med classes?

• 30:28Speaker 01

  Oh, yeah.

• 30:30Rich Roll?

  Yeah, but you're just, you know, checked out.

• 30:34Speaker 01

  Yeah, and it's so funny because a part of me thought I was being a slacker, but in hindsight, I was, like I said, I was like sneaking the four hour work week into class and reading it. So I was working hard just on these other things because the questions that evolved naturally were, okay, not only do I not know what I want to do with my life, how did all these people who I look up to, how did they do it? You know, how did Bill Gates, when he was a sophomore in college, 19 years old, nobody knew his name, sell software out of his dorm room? Or how did Spielberg, when he was rejected from film school, become the youngest director in Hollywood history? So I thought, all right, before I figure out what I am gonna do, let me just get some base knowledge so I can figure it out. So

• 31:18Speaker 01

  I just went to the library and just ripped through these biographies and business books and self-help books. But eventually I was left empty-handed. And that's when this naive 18-year-old thinking kicked in and I thought, well, if no one's gonna write the book I'm dreaming of reading, why not just write it myself?

• 31:36Rich Roll?

  Right. And you're 18, so are you a freshman in college at this point?

• 31:40Speaker 01

  And it doesn't really, it's like the perfect caliber of naive, where I'm dumb enough to not know anything, but I also like have resources in the sense that like, I'm in a dorm room with a computer and a lot of free time.

• 32:00Rich Roll?

  Naivete is underestimated. There's nothing like the power of not really knowing what you're getting into. Like, looking back now, seven years later, like, had you known, "Okay, this is gonna be a seven-year adventure." Like, with all of these pitfalls and valleys, you would have never undertaken it if you really understood what it entailed.

• 32:20Speaker 01

  Yeah, and that's...I like, think about this all the time, that while there's tremendous value in being an expert in a field, you know, you have connections, you have all this knowledge and expertise.

• 32:33Speaker 01

  One of the biggest advantages of being naive and being an amateur is you're not limited

• 32:42Speaker 01

  in the way an expert is. Because an expert sees the world through a lens of limitation, because they know how things work. But, you know, someone who's naive sees it through a world of possibility, and that is incredibly powerful.

• 32:55Rich Roll?

  Yeah, and I can understand how, at that time, you would think, "Well, how hard can it be? Like, I'm just gonna go find all these people that are super awesome, and I'm gonna, you know, interview them, and they're gonna be happy to sit down with me."

• 33:05Speaker 01

  Bill Gates helps kids all the time! You know, "Why don't you help me?"

• 33:08Rich Roll?

  Right.

• 33:09Speaker 01

  That was my thinking.

• 33:10Rich Roll?

  But the idea was, from the very beginning, like, "This is gonna be a book, I'm gonna write a book."

• 33:14Speaker 01

  My thinking was, you know, I was smart enough to know Bill Gates won't do an interview for a blog.

• 33:20Rich Roll?

  Right. Because if you're writing a book, you're legit. And this is the book, like, this is the book you wish had been available in the library that would, that would convey all the secrets and the wisdom to a young person about how to answer that question, "What should I do with my life?"

• 33:36Speaker 01

  Yeah.

• 33:36Rich Roll?

  Is that at its core, is that correct?

• 33:38Speaker 01

  At its core, at that time especially, it was less about an age and more about a stage. When someone's starting out, it doesn't matter if it's, you know, they're starting out from college, or they're in executive switching industries.

• 33:50Speaker 01

  When you're just starting out and no one wants to take your calls, no one wants to take your meetings, how do you find a way to break through? Because that was my problem. And I didn't want a book just focused on business or just focused on entertainment. I wanted a book that covered every industry. So what ended up happening is me and my best friends one night, and you actually know one of them, Kevin Heckman. Kevin, yeah. So, you know, we're all 18. I called them up and I'm like, guys, you know, I need your help. Because I didn't know what really the definition of success was, so I didn't know who to interview. And I don't really believe in these like Forbes 100 lists.

• 34:29Speaker 01

  So I was like, guys, if we can create our dream university, who would be our professors? And then that made it really easy. You know, Bill Gates would teach business, Lady Gaga, music, Steve Osnier, computer science, Jane Goodall, science, Maya Angelou, poetry, you know, Pitbull can teach Latin American studies. You know, we're just dumb 18-year-old kids. Right, okay. And we created this dream list, and I wrote it on a note card and I put it in my wallet. I was like, you know, how hard could it be? That I assumed would be the easy part. The hard part, I figured, was getting money to fund the journey. Right, how are you gonna do this? I mean, was the idea that you would stop out of college or you were gonna try to write this while you were in college?

• 35:12Speaker 01

  I mean, there's still a looming conversation with the parents that's out there that's gotta be causing you some strain. All of this was like my secret double life at this point. My parents didn't know any of this was happening. That's why even with the money thing, I couldn't like talk to them and brainstorm how to make it happen. I had to figure it out for myself because I was, you know, buried in student loan debt. I was all out of our Mitzvah cash, so there had to be a way to make some quick money. So two nights before final exams, I'm in the library and I'm doing what everyone's doing in the library. I'm on Facebook. And so I'm there and I'm on Facebook and I see someone's posting tickets to The Price

• 35:56Speaker 01

  is Right, and it's filming the next day. And the first, I know this sounds like preposterous, but the first thought was, what if I go on the show and win some money to fund this dream? You know, not my brightest moment, but I had a bigger problem. You know, I'd never seen a full episode of the show before. I'd seen bits and pieces growing up. I'd never seen a full episode. Plus, I had finals in two days. And I told myself it was a horrible idea not to do it. Um, I don't know if you've ever had one of those times where like this horrible idea keeps clawing.

• 36:30Rich Roll?

  You have a stupid idea, but you can't shake it.

• 36:31Speaker 01

  Exactly. So I had the stupid idea. I can shake it. And I remember, because I needed to focus on studying. I didn't have much time because finals were in two days. I opened my spiral notebook to make a best and worst case scenario list to prove to myself it was a bad idea. So I remember like so vividly, I'm sitting in the this corner table in the library and I'm like best and worst case scenarios, you know, worst case scenarios. Fail finals, get kicked out of pre-med, lose financial aid, mom hates me. No, mom stops talking to me. You know, look fat on TV. There are like 20 cons. And the only pro

• 37:09Speaker 01

  was maybe, maybe win enough money to fund this dream. And it felt almost as if someone had tied a rope around my gut and was pulling in a direction. So, you know, that night I decided to do the logical thing and pull an all-nighter to study. But I didn't study for finals. I studied how to hack The Price is Right.

• 37:34Rich Roll?

  All right. Well, first of all, why not just go on The Price is Right after finals?

• 37:39Speaker 01

  Dude, I had the tickets. I had one chance.

• 37:41Rich Roll?

  I see. Okay.

• 37:42Speaker 01

  I didn't know how to get tickets. I just, they like fell into my lap.

• 37:45Rich Roll?

  I see. And how do you hack The Price is Right?

• 37:48Speaker 01

  That's your inner parent right now. Looking at me like, you idiot.

• 37:54Speaker 01

  I mean, you know, The Price is Right isn't going anywhere. It's been around for a while. Oh, my god. So how do you, so, all right, so how do you hack The Price is Right? Like, what's the secret? So they make it look completely random, you know? Alex, come on down, as if they like pulled your name out of a hat.

• 38:14Speaker 01

  During my all-nighter of research, I learned there's actually a system to it. It wasn't just luck. There's like blog posts out there, people who are like... It wasn't even blog posts. It was like 1992 message boards with like the 50th comment. Like, I was... You were deep. I was like on the 23rd O of Google. Right. I'm like, super deep in this. And it's around 3 a.m. where I find out there's a producer who interviews every single person in the audience. And I, then I started, you know, researching everything about the producer, and I learned, you know, what his name was, where he was born, where he went to college. I essentially knew what he ate for breakfast that morning. And then I found out something even crazier. Because, you know, I would assume a lot of people know about the producer.

• 38:59Speaker 01

  I then found out there's also an undercover producer who's planted in the audience, who confirm or denies the main producer's selection. So while some people might know that, you know, you have a one-minute interview with a producer, no one knows that your four hours waiting in line is an interview in and of itself. Right, so this person's sizing everybody up, trying to figure out who's gonna be the best guest to get picked. Right, so I, the second I get to the CBS studio lot the morning of The Price is Right, I just, you know, I don't know who the undercover producer is, so I just assume everyone's the undercover producer. You know, so I'm like dancing with the security guards, I'm flirting with the old ladies, I'm breakdancing, and I don't know how to breakdance.

• 39:43Speaker 01

  And I'm waiting in line, and eventually it's my turn to meet the producer. And, you know, I knew all about him. I knew...

• 39:54Speaker 01

  You know, that he had a clipboard, but it was never in his hands. The assistant sitting behind him, you know, maybe 20 feet away, has the clipboard. And if he really likes you, he'll, he'll, he'll keep talking. And if he wants you on the show, he'll turn around, wink. Mm hmm. And she'll put like, put your name on the list. You knew that. I knew that going, so I knew like what I had to accomplish. I knew it wasn't just him like shaking my hand and saying, good luck. I knew I had to see the physical check. Right. So I get there and I'm standing right in front of him and he's like, you know, he has a rhythm. He's like, what's your name? Where are you from? What do you do? And I go, hey, I'm Alex. I'm, I'm 18. I'm a freshman in college. I'm a pre-med. And he goes, whoa, whoa, whoa, you're pre-med?

• 40:39Speaker 01

  You probably spend a lot of time studying. How do you have time to watch The Price is Right? And I go, oh, is that where I am? Like, no, I don't even get a pity laugh. Like, you're giving me more of a laugh than I got. So I don't even get a pity laugh. And I can see his eyes wandering and like quickly, I knew I had to do something. And in one of those business books I had read, it might, I think it was like a Tony Robbins book. It said, human contact speeds up a relationship. So I had an idea. I needed to touch Stan. So I, I go to the producer Stan. I'm like, Stan, like come over here. I want to make a handshake with you. And he, you know, is very hesitant and I'm like, come on, come on. And he, he comes over. I teach him how to pound it and blow it up.

• 41:24Speaker 01

  And, you know, he laughs and he's like, oh, you're gonna do great. Good luck.

• 41:29Speaker 01

  And starts walking away. You know, doesn't turn around. Strike two. Doesn't, the assistant is writing the clipboard. And this was like one of those moments where you can see your entire dream like right in front of you. And see it walking away, almost like slipping through your hands like sand. And the worst part was that you know, you didn't even have a chance to fully prove yourself. So I don't know what got into me, but I started yelling at the top of my lungs. Stan! Oh my god. Like, and the whole audience shoots their head around like, are you, what's going on? And Stan runs over, like they think I'm having a seizure. He's like, are you okay? What's happening?

• 42:15Speaker 01

  And now I have no idea what I'm gonna say. So I'm just looking at him.

• 42:18Rich Roll?

  You're either gonna get tossed out for being a lunatic.

• 42:21Speaker 01

  But my thinking was, you know,

• 42:23Rich Roll?

  You're already gone.

• 42:24Speaker 01

  Yeah, what's the point of staying, right? I, I'm not on the show at this point, so I might as well go all, all the way in.

• 42:32Speaker 01

  So I'm looking at him, he's looking at me. And this guy's like, you know, typical Hollywood, like turtleneck, you know, red scarf, even though it's 70 degrees, like, and I, I just look at him and I'm like, "Your scarf!" And now I like, really don't know what I'm gonna say next. And, you know, there, it's dead silent, like, every, there's so much tension right now.

• 42:55Rich Roll?

  They're like, "Let's watch this guy just bury himself, he's digging his grave right now."

• 43:00Speaker 01

  So, I end up just looking at Stan with like, all the confidence I can, and I just say the only thing I can think, I'm like, "I'm an avid scarf collector, I have 362 pairs in my dorm room and I'm missing that one, where did you get it?" And I'm like freaking out, and he starts cracking up, because I think he realized what I was actually trying to do. And he like, gives me his scarf, he's cracking, he's like, "Look, you need this more than I do." He turns around, winks, and his assistant makes him work on the checkboard.

• 43:30Rich Roll?

  And you know you're in.

• 43:31Speaker 01

  I know, I'm in.

• 43:31Rich Roll?

  That's so bananas, like, because it's not like, it's not like you gave him the secret to the universe, or like, imparted some wisdom that was undeniable, that made him, you just, you just kind of like threw a ninni. I mean, that was like a hail mary, I don't know what that was.

• 43:47Speaker 01

  The book journey is pretty much me desperately throwing hail marys and missing nine out of 10, but the one that makes it is like the craziest shit ever.

• 43:56Rich Roll?

  But I think, you know, behind that is your willingness to throw hail marys, like, you're, you have, like, look, you have gumption, you have hustle, you got, you have charisma, you have personality, I would imagine your grandfather must have seen this in you. Did he identify you as some kind of kindred spirit, even though you were on this empty track?

• 44:15Speaker 01

  You know, funny enough, that's actually why he doubled down so much on me becoming a doctor, because he didn't want me to live and suffer the way he had to as an entrepreneur.

• 44:23Rich Roll?

  It was almost like he saw too much of himself in you and wanted something different for you.

• 44:29Speaker 01

  That's crazy. I never thought of that. Yeah.

• 44:31Rich Roll?

  So, all right, so you get on the show and like you win big, right? Like what you win like a sailboat or something?

• 44:37Speaker 01

  I end up, yeah. So the way the hacking of the show worked, it was less Einstein and more Forrest Gump. And I end up winning the whole showcase showdown, winning a sailboat, selling the sailboat, and that's how I funded the book. And the sailboat I sold for like $20,000, which for a broke college student is like a million bucks.

• 44:58Rich Roll?

  Yeah.

• 44:58Speaker 01

  You know, my most expensive expense is like Chipotle with guacamole. So, you know, I'm feeling like a billionaire. And I used that money to fund the journey. And, you know, it took two years, but I eventually got to Gates. It took three years to get to Lady Gaga. And, you know, like you said, seven years later, the book is just finally finished.

• 45:18Rich Roll?

  Right. And, and you, so you take this money, do you end up stopping out of school or are you still a student while you're doing this?

• 45:25Speaker 01

  So I'm still a student because, you know, I love college and my, I had some awareness of just how much my parents had sacrificed for me to be in school. I remember, so when I got into college, my mom said I couldn't go because we couldn't afford it. And she really, really insisted on me going to a community college that was less expensive.

• 45:52Speaker 01

  But I remember my dad, you know, the night before the deadline enrollment date, the day you have to either confirm or deny.

• 46:00Speaker 01

  And my mom was like 100% against me going.

• 46:04Speaker 01

  And I remember through the walls, hearing my dad

• 46:09Speaker 01

  like cry, my dad never cried, like at funeral, just never would cry. The first time I'd ever heard him cry in the house in my life was that night, pretty much telling my mom he'd do whatever it takes. And I had to go and my mom said yes.

• 46:29Speaker 01

  So I understood that.

• 46:32Speaker 01

  How, how much my parents had given to help make this possible. So dropping out wasn't even on the radar. But what ended up happening is now that I had won the Price is Right, I was like gung ho on making this, this mission come, come together. And to me, the holy grail of interviews was Bill Gates. Cause when I was 18, I thought, you know, if anyone had the answers to the universe, it had to be Bill Gates. So I spent a whole year trying to get in contact with Gates's office.

• 47:04Rich Roll?

  And part of that is to legitimize this project, not only to yourself, but to your parents and to kind of solidify that this is a real thing.

• 47:15Speaker 01

  Maybe subconsciously, like I wouldn't be surprised if that was going on in my subconscious.

• 47:21Speaker 01

  What I was thinking at the time was, and you know, this might sound like a naive idea to some people, but to me, I really believe it, which is I just really believe that if all these people come together, you know, not for press, not to promote anything, but really just to share their best wisdom with the next generation, young people can do so much more. And.

• 47:46Rich Roll?

  Yeah, it's, that's an altruistic pitch. That's a pitch that's hard to turn down if you're somebody like Bill Gates.

• 47:52Speaker 01

  I, that was, that was my hope.

• 47:54Rich Roll?

  That's what you thought.

• 47:55Speaker 01

  To my surprise, Bill Gates doesn't do interviews with 18 year old college students. So, you know, I spent a year getting in contact with Gates's office. And finally, at, you know, a year into it, I'm 19, I get on the phone with Gates's Chief of Staff. And we're on the phone and, you know, you talked about the, what was it? The Calabasas Smart, where you're on the phone with the Crown?

• 48:19Rich Roll?

  Yeah.

• 48:20Speaker 01

  So I have a similar story where I'm in a CVS parking lot, holding an ice cream cone. When my phone rings and I see like the Seattle area code and I knew who it was, I like pick up the phone and on the line is Bill Gates's Chief of Staff, who like, it's like Melinda, Bill in this guy.

• 48:37Rich Roll?

  Right.

• 48:37Speaker 01

  Like they run it. It's crazy. And he's like, so you want to interview Bill, huh? It's very, I'm like, yeah, it's my biggest, I'm 19, I'm like, it's my biggest dream. And he's like, look, I love what you're doing. I love that you're doing this to help others. And I'm like thinking I'm, you know, 95% there. And he's like, but. The thing is, we don't really do interviews like this. He's like, especially, you know, with some, with a book that doesn't have a publisher. And he's like, look, if you can go get a publishing deal from, you know, either Penguin or Random House,

• 49:19Speaker 01

  and go build more momentum, call me back. Click.

• 49:24Speaker 01

  So that then, you know.

• 49:26Rich Roll?

  Because now you have a mission.

• 49:27Speaker 01

  So now, well, I was torn. A part of me was like my head in my hands, but a few days later, I was like, okay, fine. He told me what I needed. I, what's the, what the fuck is Random House? Like, I had no idea. Like, how hard could that be? So I then go on this eight-month journey of, you know, getting rejected every single day, trying to get this publishing deal, because I was a 19-year-old kid trying to write a business book. And.

• 49:53Rich Roll?

  Right. I mean, like, just, let's just take a step back and like, analyze the preposterous nature of that.

• 50:00Speaker 01

  And I'm going to that, and I'm like, God.

• 50:02Rich Roll?

  Your, your biggest business achievement is like hacking Price is Right.

• 50:06Speaker 01

  And the funny thing is too, you know, maybe if I had interviews lined up, it would be a better thing. But I remember my book proposal, it was like, interviews that I'm very likely to get. I couldn't even say, like, these are the interviews I was gonna get.

• 50:21Rich Roll?

  At least you're honest, you know. Most people aren't. So, so I would imagine you put a proposal together. I mean, how did you get it in front of Rick Oregon and sell him on the idea of doing this book with you?

• 50:30Speaker 01

  So what I had learned over, so at this point, I'm about a year into my journey. And, you know, I'm reading every business biography. And I'm getting like some good interviews. I'm interviewing Tim Ferriss. You know, there's some, there's some early traction. And one thing I had learned is that, and Tim Ferriss actually gave me this in my interview with him. He gave me this cold email template where he launched his career by emailing VIPs and CEOs. And he gave me this cold email template that.

• 51:06Speaker 01

  Gave me sort of this like amazing tool. I don't know if you want me to go into it, but he gives me this tool that I then use to email about 30 different New York Times bestselling authors, asking for their advice on how to get a book deal.

• 51:21Speaker 01

  And the overwhelming advice I got from all of them, they gave me a lot of tactics, but the biggest thing was the number one thing to getting, you know, if you're unknown,

• 51:34Speaker 01

  the number one thing to getting a big publisher is a big agent, you know, no big agent, no big publisher. So my thinking was no big agent, no Bill Gates. So that eight months journey was really about getting the agent. And once I got the agent, and you know, I was rejected by dozens and dozens of, it's just crazy. Yeah. But when I finally got the publishing deal, well, this is a month before I got the publishing deal. I got the agent.

• 52:03Speaker 01

  And she had told me, look, Alex,

• 52:07Speaker 01

  you know, we're not going to go to the publishers during Christmas time. That's, you know, crazy. We can either go next month, or we can wait for the spring. It's up to you. And I knew it's already been a year, like almost a year since I spoke to Bill Gates' chief of staff. And I was like, look, I can't wait anymore. Like, he's probably already forgotten about me. I need to make this happen. The only problem was my junior year of college is starting the next week. And I knew, you know, trying to finish my proposal in a month was hard enough to begin with. Doing it while balancing school was impossible. And that's when I had to make at the time, the hardest decision of my life between

• 52:50Speaker 01

  moving forward on my dream,

• 52:54Speaker 01

  but turning back on my parents' sacrifice and their dreams. So how'd that conversation go?

• 53:01Speaker 01

  A conversation is a very generous way to put it.

• 53:06Speaker 01

  So what's crazy is when I started on my book, even before I even talked about leaving college, you know, my grandparents and my parents sort of sniffed this was coming. So my grandma, who, you know, I love dearly, I was just on the phone with her 30 minutes ago, an hour ago. She was like,

• 53:26Speaker 01

  "Fine, you want to, you want to write this book, you know, and you're part-time? Fine."

• 53:33Speaker 01

  But you're not going to become one of those, you know, crazy American kids who drops out of college and travels the world to find himself. You know, she had seen the movies. She's like,

• 53:46Speaker 01

  begu junaman, swear on my life that you'll graduate undergrad and get your masters. And only then will I support what you're doing. I like how she threw master's degree in. Oh my.

• 54:00Speaker 01

  Slid that in there too. Oh my God. And it was non-negotiable too. Cause she understood that, you know, in America these days, an undergrad doesn't have the guarantees it used to. And I was like, fine, fine. I promise. And she goes, no. Begu junaman, which literally means I swear on your life. It's the strongest promise in the world. So fast forward a year later, when I'm talking about leaving school,

• 54:26Speaker 01

  this junaman promise is looming overhead. So I had a problem because I don't want to, I don't want to break my grandma's promise. I didn't want to ruin, you know, my mom's dreams. So I call my mentor, who I know you know, Elliot Bisno. And I tell him, Elliot, this is, I don't know what to do. How, how can I choose between my family? Cause you know, family is the most important.

• 54:55Speaker 01

  But at what point do I stop living for them and start living for myself? And he's like, I don't understand the problem. And I'm like, well dude, I, the only way I can get this publishing deal and get to Bill Gates is if I drop out of school. And he goes, whoa, whoa, whoa. You are not dropping out of school. And I was like, what? And he's like, look, no one smart actually drops out of school. Go, you know, do your research and you'll see what I'm saying. And he hangs up and I'm like, what is he talking about?

• 55:27Speaker 01

  And he ends up sending me on this, you know, mini like 24 hour quest where I started ripping through Zuckerberg and Bill Gates' biographies and I finally found out what Elliot was talking about. When Zuckerberg had started, you know, the Facebook, that summer, he was working on a full time, he went to go meet with Peter Thiel to get a half million dollar investment. And Thiel goes to Zuckerberg, "You're gonna drop out of school, right?" Zuckerberg's like, "Not a chance." Thiel's like, "Oh, okay, let's see what happens." And even when school was starting, Zuckerberg still didn't want to drop out. It was only his friend Dustin

• 56:11Speaker 01

  Moskovitz who was like, "Look, man, we'll barely survive, you know, if we did this full time. Let's take one semester off and see what happens." Then I looked at Bill Gates' story and I realized he did the same thing. He took one semester off to work on Microsoft and when it wasn't working out, he actually went back to Harvard, which no one talks about. Yeah, I didn't know that. Yeah, no one, no one talks about this. That Bill, everyone calls, you know, "Bill Gates dropped out of college and, you know, threw his middle finger in the sky." No, he actually went back to school when things weren't working out as well as he wanted.

• 56:51Speaker 01

  So I called Elliot back up and he's like, "Bingo. Yeah, don't drop out. Take one semester off and it doesn't work. You didn't break your grandma's promise." Right. So I feel like I just discovered the secret to life. So I like drive to my college campus. I ask for like this leave of absence form, which says I have a seven year window. I drive home to tell my parents the good news.

• 57:14Speaker 01

  This is not good news. Literally, I remember my mom yelling, "My son will not be at college!" Just, you know, she's gone hysterical. And for weeks, I'm just going back and forth with them.

• 57:31Speaker 01

  And at the end, I had to come to terms with, although my mom might be right, although this might be the biggest mistake of my life.

• 57:42Speaker 01

  I'd rather be 80 years old and know that I tried than 80 years old and know I had failed.

• 57:48Rich Roll?

  Yeah, I think the the bigger issue here is that divining line between living your life for somebody else and living living it for yourself with the understanding that you know that this is your true north. You know, it's after a year or so into this project, I think you had paid your dues enough to know like, okay, this is the path for me. And that's tough as a young person. It's tough for anybody in any situation to have to wrestle with that.

• 58:16Speaker 01

  Yeah. You want to know the craziest thing that happened on that day? So it's the day to turn in the leave absence form. And I finally wait until the final day to, you know, sign the form. There's like, two hours left until the deadline. I'm gonna go drive to campus. I'm at my parents' house. I have the green form. I fold it up in my pocket and I hear the doorbell ring. So, you know, I grab my car keys. I walk towards the door. And I turn the knob and I open it up. And standing on the front step is my grandma. You know, just tears streaming down her face. And still to this day, I'll never forget what that felt like.

• 58:59Rich Roll?

  And how's it now?

• 59:01Speaker 01

  Ah, I love her.

• 59:09Rich Roll?

  I feel like half the time I run into you at this event or that event, you're with like 20, 20 family members. So I figure I feel like it all worked out.

• 59:18Speaker 01

  We actually have a picture with me and you, Cal, and my parents at one of Incu's shows.

• 59:25Rich Roll?

  Oh, is Cal in that picture too?

• 59:26Speaker 01

  I don't I don't think you guys knew each other yet.

• 59:29Rich Roll?

  No, you know, it's funny. And I want to talk about Cal in a minute. But I just ran into Cal like a week ago.

• 59:34Speaker 01

  Where was it?

• 59:36Rich Roll?

  I was down at Dodger Stadium to do this.

• 59:40Speaker 01

  The Spartan thing.

• 59:41Rich Roll?

  The Spartan, yeah. So Joe DeSena, who, you know, is the Spartan dude. There was a Spartan event at Dodger Stadium. And up in one of the skyboxes, he was doing podcast interviews and like video interviews. And so he's like, come down, like, I'd never met Joe in person. He's like, come down, like, let's, you know, come on my show, which was great. You know, we had a great time, totally cool. And then he's like, hey, I'm also, I'm, I'm doing this documentary thing. I'm trying to, he's like, I'm taking this guy, I'm putting this guy through the paces. You know, I'm trying to get him fit. I'm trying to sort out his diet and like, he just, the guy's not listening. I was like, I'm having such a hard time. He goes, will you talk to him?

• 1:00:24Speaker 01

  Did you know him before?

• 1:00:25Rich Roll?

  Will you? No, well, first of all, like, he just didn't say who it was. He's like, will you talk to him? Like, we're doing this, maybe we'll film you a little bit, like, we'll have a little interaction. I was like, yeah, whatever you want. So we go out into the bargain lot and I'm with this film camera, Joe, and like, you know, there's a cinematographer there and like, and we walk up and Joe introduces, he's like, hey, this is, this is Cal. I was like, hi, I'm Cal. And I'm like, like, oh, Cal Fussman. Like, I, Cal doesn't know who I am, but I was like, yeah, I know, I know who you are. Like, cool, nice to meet you. And he's wearing the fedora hat with the Spartan, like, the Spartan bandana on his fedora.

• 1:01:00Speaker 01

  Oh, my God.

• 1:01:02Rich Roll?

  And, and I'm like, yeah, I hear from Joe, like, you're, you're resisting. So we get into this weird conversation. And the bizarre thing is that I feel like we were, we were like ships in the night. Like, whatever Cal was saying, whatever I was, we were just missing each other. And I look at Joe and I go, you got your hands full with this guy. Like, I don't, I don't know if I can help you.

• 1:01:25Speaker 01

  I, I love Cal. At the same time, everything you just said makes, I can see that happening.

• 1:01:30Rich Roll?

  Yeah, and I hope it's okay that I told that story.

• 1:01:33Speaker 01

  No, that's very.

• 1:01:33Rich Roll?

  Big secret or something like that.

• 1:01:34Speaker 01

  No, he would probably say the same story too, because it's.

• 1:01:38Rich Roll?

  So next time you, you see Cal.

• 1:01:39Speaker 01

  I'm gonna call, as soon as we're done, I'm gonna call him on the train home and tell him that.

• 1:01:44Rich Roll?

  But what's cool, and to bring it back around to your story, like, Cal becomes, we should probably explain who Cal is and how he kind of came into your equation.

• 1:01:53Speaker 01

  So this is probably the most miraculous coincidence that happened on the whole journey. And there were a lot of miraculous coincidences.

• 1:02:06Speaker 01

  This was a few years into the journey and I had just spent eight months trying to, you know, track down Warren Buffett, writing him letters, and I was just getting rejected at every turn. To the point where at the end of the eight months, I was completely depleted, you know, just all the life was beat out of me. And one of my best friends, Corwin, was, you know, trying to get my spirits up. And he's like, come on, let's go, let's grab a bite to eat. So we go to this grocery store and we grab sandwiches and we're, you know, sitting on the sidewalk. And, you know, I'm just venting to my friend, you know, and I'm telling him, man, I don't know what the point of this, I don't know how I'm gonna do this.

• 1:02:49Speaker 01

  And he's like, come on, you gotta, you gotta, you know, you gotta have some interviews lined up. And I'm like, I got nothing. And he's like, come on, you gotta, you gotta figure something out. Like dude, do you know what, even if I had interviews, like I would probably fuck them up, you know? Look what happened in the last one. And he's, as we're complaining about how hard interviewing is, this car pulls up right in front of me. The door opens and out walks Larry King. And I don't know if you want me to go into the whole story.

• 1:03:21Rich Roll?

  No, I love this story. I know the story, but like, it's a great story. And I think it really, it, it, it creates the foundation for everything that follows. Like, I think it's, I think it's, you know, an integral part of, of the whole book. Because I think, and we can get into this later, but just to kind of like, define it now, I think the value of the book is much more the journey that you go on to create the book than it is the wisdom imparted by these people that you ultimately end up talking to. And yes, they're providing these insights and that has, you know, tremendous value, but you're

• 1:04:04Rich Roll?

  learning experientially through this and you're answering your own questions. You know, the book is called The Third Door and you can explain why that is, but ultimately, you know, you're finding the third door all the way through in every opportunity to try to make this happen. So it's almost like you're, you know, the solutions that you're looking for, you're practicing along the way. And it's a process of just coming into an understanding of that as you go.

• 1:04:32Speaker 01

  Thank you, man. That's.

• 1:04:35Speaker 01

  Feels really good to hear.

• 1:04:37Rich Roll?

  So back to the story.

• 1:04:38Speaker 01

  Okay, so back to, back to me just harassing Larry King. So, you know, his car pulls up, he walks out, but. And it's weird because I know I sound like this extrovert person who's like down too many Red Bulls, but I'm really a very shy and introverted and I, I grew up with a tremendous fear of rejection and failure. So as Larry King opens that car door, I'm like paralyzed and I almost call, I call the feeling the flinch. And he's literally walking right in front of me, right past me and goes through the store's

• 1:05:20Speaker 01

  sliding windows and I can't say a thing. And my best friend Corwin like nudges me, he's like, dude, what, what the fuck like? Why didn't you say something? And this is where the flinch gets very good. I start explaining all the good reasons why I shouldn't have said anything. I don't want to bother him. He's like, dude, come on. And you know, I, I'm like, look, he's already in the grocery store. I can't find him. He's like, dude, he's 80 years old. How far could he have gone?

• 1:05:47Rich Roll?

  Right. And, and you're complaining about how this isn't working out and then God just delivers like this dream, you know, interviewee right in front of you.

• 1:05:55Speaker 01

  Exactly. So just to not be embarrassed in front of my friend, I very reluctantly get up. I walk, I walk through the stores, you know, sliding glass windows and I look around the bakery section, no Larry. Yeah. So I jog over to the produce section, you know, fruits, vegetables, no Larry. And that's when I remember I had spent, or no Larry had parked in the loading zone, which meant he was leaving any minute now. So that like bolt of adrenaline and the fear of, you know, failing again, you know, overtakes me and I start sprinting through this grocery store, going down every aisle, no Larry, no Larry, no Larry, no Larry, no Larry.

• 1:06:39Speaker 01

  You know, I cut down the frozen food section, you know, I'm dodging old ladies, like I'm, you know, swerving around cans of tuna fish, no Larry. So he has to be at the checkout counter. So no Larry, no Larry, no Larry, no Larry.

• 1:06:57Speaker 01

  And at this point, I wanna, you know, kick myself because it was, like you said, it was right in front of me and I blew it. So I'm walking out of the parking lot and I'm looking down at my feet and I lift my gaze and right there, 20 feet in front of me is Larry King. And similar to that Stan story I told you about on The Price is Right, this feeling like overtakes me and I just, I'm trying to project, but I think all of this, you know, pent up anger and energy inside of me combusted and I accidentally shout, "Mr. King!" In the, it was an indoor parking lot, so it echoed and literally, I'll never forget

• 1:07:41Speaker 01

  the look on Larry King's, the poor guy, he's had like quadruple bypass surgery. He like jumps up like this, his shoulders arch up and he turns his head around slowly, like, like every wrinkle in his face, you know, sprung back, his eyebrows to his hairline, you know, as if he's seeing the Grim Reaper. So he, you know, starts, you know, heading towards his car. Get in my car as quickly as possible to get out of here. And I'm thinking like, shit, I'm too deep in this to, to stop now. So I like run after him, I'm like, "Mr. King, Mr. King, my name's Alex, I'm, you know, I'm 20 years old, I've always wanted to say hi." And he's like, "Okay, hi." And you know, speed, you know, goes off faster.

• 1:08:23Speaker 01

  And we're finally now in front of his car, he's like putting his groceries in the trunk. He opens the driver door and I just go, "Wait, Mr. King.

• 1:08:35Speaker 01

  Can I, can I go to breakfast with you?" In his look of confusion. Oh my god. And, you know, he's about to say no, but he looks around at the sidewalk and sees there's about like 10 people watching this go down. Right, so he better behave him. So he literally just like shrugs and is like, "Okay, okay, okay." I'm like, "Oh my god, thank you, thank you so much. Um, I, I, great, I'll, I'll see you tomorrow." And he like gets in the car and closes the door and I go, "Wait, Mr. King, what time?"

• 1:09:13Speaker 01

  And he looks at me and like starts the engine of this car. He can definitely hear me. I'm like, Mr. King, what time? He like puts the car into drive. I'm now standing like in front of the car waving my arms in front of the windshield. Mr. King, what time? And he just looks at me and he's like, nine o'clock and just speeds off.

• 1:09:37Speaker 01

  And the next morning.

• 1:09:39Rich Roll?

  You're like a celebrity's worst nightmare. A little schooling on like having a little more deft approach to, I mean, that's just like sheer desperation.

• 1:09:49Speaker 01

  Um, but look, that's what happens when you drop out of school and lie to your grandma and put it all on the line. You do some crazy stuff to try to make it work. And so I go to Larry King's restaurant. And I show up there nine o'clock and there he is, sitting in the corner booth with his, his friends and you know, I had a little bit of self-awareness at this point where I knew.

• 1:10:12Rich Roll?

  Right. We're talking about Nate and Al's, right? I've seen him in there. Does he still go there every morning?

• 1:10:18Speaker 01

  He, um, he goes to, he goes to, he has like a schedule where every week there's a, there's a every day of the, if you name of the day of the week, I can say where he's at for life. Right? So, right. That makes me sound normal.

• 1:10:34Rich Roll?

  You know, a little bit too much about this. All right, go ahead.

• 1:10:37Speaker 01

  Okay. So I get there and I was a bit embarrassed by how, how I had acted the day prior. So I was trying to be a lot calmer. So although there was an open seat, I didn't sit down. I'm just like, hey, Mr. King, good morning. And he goes,

• 1:10:55Speaker 01

  you know, sort of waves me away. So,

• 1:10:58Speaker 01

  I'm like, all right, he wants some time alone with his friends. So I sit at the table next to him, waiting to be called over. And 10 minutes passes. 30 minutes pass.

• 1:11:11Speaker 01

  An hour passes.

• 1:11:14Speaker 01

  And finally, he stands up.

• 1:11:17Speaker 01

  And he's walking towards me and I can like feel my cheeks lifting. And then he walks right past me and heads for the exit.

• 1:11:24Rich Roll?

  Uh huh.

• 1:11:25Speaker 01

  And I, I just like wave, wave my hand, my K, Mr. King. And he goes, what is it, kid? What do you want?

• 1:11:33Speaker 01

  And at this point, I'm just like, I have no energy. And I'm just like, honestly? I just wanted some advice on how to interview people. And this smile like spreads across his face, almost as if to say, why didn't you say so?

• 1:11:50Rich Roll?

  What do you think he thought you were trying to do?

• 1:11:55Speaker 01

  In high, he deals with a lot of crazy people, anyone of his caliber, especially someone as approachable as Larry. So you have to understand, he, when he was at CNN, he was, if not the, one of the most recognizable faces on earth.

• 1:12:14Rich Roll?

  He also doesn't hide from the public. Like you said, he's out, you know, like if you want to, if you want to find him, you can find him. Like he, he doesn't ensconce himself in his house. Like he's out in the public. So he's probably getting rolled up on quite a bit.

• 1:12:26Speaker 01

  Right. Especially by crazy kids.

• 1:12:30Rich Roll?

  I was like in a urinal next to him after a movie many years ago.

• 1:12:34Speaker 01

  Oh, he loves going to the movies. Yeah.

• 1:12:37Rich Roll?

  Anyway, go ahead.

• 1:12:38Speaker 01

  I have a funny movie story with him later. So, he's like, you know, he smiles and he ends up, you know, putting a hand on my shoulder and giving me, you know, this one minute monologue of the best interview advice I'd ever heard. And at the end of this monologue, he goes, he like looks up almost as if he's like debating something in his mind. And he looks at me in the eyes and like puts a finger in my face and goes,

• 1:13:07Speaker 01

  All right, kid. Tomorrow, 8:45. See you here. And I show up the next morning at 8:45. He calls me over to his table. I sit down. He asks me, like, what are you even trying to interview for? And I tell him about the book. And he's like, all right, I'm in. And over the course of the past few years, I've been at breakfast with him about 50 times. Wow. And this all comes full circle because the next thing that happens at the table is we start talking about the book on that first morning of breakfast. And now this is the second morning. This is my first morning at the table. And I'm telling him about my dream. And he goes, I got someone I want you to meet. Hey, Cal.

• 1:13:50Speaker 01

  And this younger guy who's, you know, in his late 50s, because everyone else at the table is in their 80s. This younger guy, a fedora, turns around and Larry goes, you have a minute? And, you know, sort of sends me off with Cal. And Cal, I learned Larry tells me that his name is Cal Fussman. And he is, you know, the writer of Esquire magazine's What I've Learned column. And he's interviewed Muhammad Ali, Mikhail Gorbachev, George Clooney, you know, every person who's defined culture the past 50 years. And Cal's a New York Times bestselling author. And Cal and I end up, for what's supposed to be a minute conversation, we talk for three hours.

• 1:14:33Speaker 01

  And that conversation turns into another conversation the next day. And Cal and I, you know, create this relationship where he realizes how much help I need. Because I have this big lofty dream of writing a book that changes people's lives, yet I have zero writing experience. And Cal was working in the magazine industry when it was shrinking at a very scary rate. And he didn't know, he didn't even know how to create a Twitter account. Forget about how to tweet. He didn't even know where the login page was. He's full analog.

• 1:15:10Speaker 01

  So we sort of create this relationship where I start helping him with his, you know, his, you know, create a Twitter account. I make a website for him. And he starts teaching me how to like, write a sentence. And.

• 1:15:23Speaker 01

  Like, again, like a miracle. While the Larry situation feels like a miracle, what Cal did for me was a miracle. And he sat down with me over the past almost four years. Every, you know, every week, at least three times a week, for about three hours at a time, looking over my chapters and teaching me how to write.

• 1:15:50Rich Roll?

  That's amazing.

• 1:15:51Speaker 01

  And

• 1:15:52Rich Roll?

  That's a, why do you think he was willing to invest so much of his energy in you?

• 1:15:59Speaker 01

  The obvious number one is he's so kind. And, you know, you can't, you can't fake it. You're either, you have that heart or you don't. I got that, I actually asked this guy who I met. He's really smart guy. He was the, he used to be a VP at Goldman Sachs. And I asked him, because he was giving me a lot of advice too. I asked him like, how do you choose like which people to mentor? You have such little time. And he has this theory, which I think is really brilliant, about why someone chooses to mentor someone subconsciously. Because it's never really a conscious decision when you give of yourself in that way.

• 1:16:43Speaker 01

  And he said, someone mentors you for three reasons. One, and they're all subconscious reasons. One, they see some of themselves in you. Two, they want to help you be more like them. Whether it's because they have a special expertise they want to help you with, but they want to help you and they feel they can help you be more like them. The third one is the most interesting. They want to be more like you. And that's sort of confusing, but what he explained to me is like, you know, if someone's a, you know, 70-year-old CEO, sometimes the thing they need most in their life is 19-year-old enthusiasm about their company.

• 1:17:29Speaker 01

  Because they're so, you know, lackluster at that point.

• 1:17:32Rich Roll?

  Right, right. No, I totally get that. I totally get that. And just not really knowing that much about your relationship with Cal and the dynamic, you know, it's clear to see how you were able to bring that to him because I've watched his career change in a very dramatic way, just in the last couple of years, from, you know, James Beard, award-winning magazine writer, to a guy who's now like, very well-known in the digital universe. You know, he's been on Tim Ferriss's podcast like twice, I think.

• 1:18:06Speaker 01

  Three times now.

• 1:18:07Rich Roll?

  And I saw him speak at The Shine, and I know our mutual friend Kevin is now his manager. And I believe you're the one who introduced him to Elliot, and then he became a speaker at Summit. And so now he's like, this guy who has, you know, like, this whole life and career that he could not have conceptualized prior to meeting you.

• 1:18:27Speaker 01

  Cal, I always mess with him, because I like to remind him. By the way, Cal's Twitter is fantastic. He puts out all these great quotes, and he gets tons of retweets. But I always joke with him, because in our first conversation, I asked him if he has a Twitter account. And he laughed in my face and said, "Twitter is my kryptonite." And he like, literally laughed in my face. And he's just done so well. And, you know, all credit goes to him. But like you said, he, you know, his podcast is incredible. His, his speeches bring people to tears. He, he has a newsletter now. It's just night and day, and I'm just so proud of him. And he's like, family to me. His goddaughter, his daughter is now my goddaughter.

• 1:19:15Speaker 01

  You know, I'd her bhamitvai, like, went up and lit a candle, and it's been one of the biggest honors of my life.

• 1:19:20Rich Roll?

  Super cool. And, and what was it that he, like, what's the main thing that you learned from him about writing?

• 1:19:29Speaker 01

  Oh, wow. I can, you know, I have this fantasy of one day, you know, after the book launch, teaching like, a, you know, a 10-hour course of what Cal taught me over four years. And, because I can give you, like, I'll give you three things, just off the top of my head, that are the biggest things, though. But I can give a whole, it's like my dream to pay it forward, because what he gave me was life-changing. Number one...

• 1:19:59Speaker 01

  Is, oh man, it's crazy because when I first sat down with Cal, I don't think I've ever told this publicly, in our first conversation, he said Twitter's my kryptonite and I said something even more preposterous. He asked me what my plans were of how to write the book and I said, I can't believe I'm admitting this, but I said, Cal, I've read a lot of statistics and blog posts and I know that with a business book, and I'm writing a business book, 90% of people don't read past the first chapter, so I'm not too worried. And he looked at me like.

• 1:20:30Rich Roll?

  That's like the worst thing you could tell a guy, like a real writer.

• 1:20:35Speaker 01

  Right. It is his profession. He's an artist. And so Cal taught me how to do the opposite, which is how to write a book where 90% read the final sentence. And there's three ways to do it. Well, there's a lot of ways, but the three main things he taught me. Number one is every single chapter, you cannot have an exception, needs to have tension. Every single one. I thought I could get away with like, you know, the first chapter having some tension, the middle chapter and the final, every, it doesn't matter. And that

• 1:21:17Speaker 01

  is really hard. My issue was if I was writing a fiction book, Cal's advice would have been very, much easier to implement. Because it was a nonfiction book and I had to write about, some of the, look, some of the chapters were my stories and I could tell them. But some of the chapters were me and Bill Gates sitting in an office for an hour with an audio recorder and Bill also recorded, his team was smart enough to also record it. So I can't even change a word of what was said in there.

• 1:21:48Rich Roll?

  Yeah, but what you can do is describe what was happening with you emotionally, because I feel tension just hearing that. Like, okay, you're a kid, you walk into this office, there's a whole team of people, they're recording it on their end, what are they going to do? What's their agenda? Like, how am I going to navigate that? Like, you know, my palms can get sweaty just hearing about that. There's a lot to work with there.

• 1:22:09Speaker 01

  Yeah. Well, I'm so happy that you're a brilliant writer. But that's, Cal had a big job of teach me that of, you know, every chapter needs tension. So that's number one. And actually, there's this great thing from, um, I don't know if you've ever seen MasterClass?

• 1:22:27Rich Roll?

  Yeah.

• 1:22:27Speaker 01

  These online course.

• 1:22:28Rich Roll?

  Right, right, right.

• 1:22:28Speaker 01

  They're incredible.

• 1:22:29Rich Roll?

  Yeah.

• 1:22:29Speaker 01

  And there's.

• 1:22:29Rich Roll?

  They're all like, super high end.

• 1:22:31Speaker 01

  It's like HBO for an online course.

• 1:22:34Rich Roll?

  Malcolm Glad- are you the Malcolm Gladwell?

• 1:22:36Speaker 01

  The Gladwell, but the one that I'd recommend to any creative writer, filmmaker, anyone is the Aaron Sorkin one.

• 1:22:42Rich Roll?

  Hmm.

• 1:22:42Speaker 01

  And he, in a perfect sentence, says what the key is to tension. And Cal taught me this too. He says, "You need a very strong intention

• 1:22:58Speaker 01

  and very, very, very crazy obstacles." Because you can have all these crazy obstacles, but if there's not an intention, like, "If I don't do X, Y will happen."

• 1:23:12Rich Roll?

  Right.

• 1:23:12Speaker 01

  Like, you can do a, um, a movie about.

• 1:23:14Rich Roll?

  Consequences.

• 1:23:15Speaker 01

  A consequence, stakes. And that's what Cal taught me. You need to have stakes.

• 1:23:22Rich Roll?

  Right, so then you're like, just to, to extend the analogy of the Bill Gates interview, what are the stakes? Like, okay, so he, he doesn't want to talk to me, or the interview doesn't go well. Like, what's the worst thing that could happen? Like, it's hard to come up with, like, stakes that are super high.

• 1:23:37Speaker 01

  Well, what Cal is so good at is because he's one of the best interviewers on earth, he would help me, he would ask me questions, almost like a therapist, that would pull the answers out of me that I didn't even know. Like, he would, like, I would write the first draft of the Bill, so the, the Bill Gates chapter, for example. Um, that was the hardest chapter to write by far. That took 134 edits. And that's before I sent it to Crown.

• 1:24:04Rich Roll?

  Drafts, you mean, drafts?

• 1:24:05Speaker 01

  Drafts.

• 1:24:05Rich Roll?

  That's like insane.

• 1:24:07Speaker 01

  And that's before I sent it to Crown. And then, once it got to Crown, it went through probably another, like, 30 to the final one. So it's probably about 160 at this point. Um, and then proofreading, prob- it's probably.

• 1:24:17Rich Roll?

  Meanwhile, meanwhile, I'm like, on my phone, looking at your Instagram, and you're like, "Sitting down to rewrite this chapter again." I go, "This guy's just afraid." Like, I'm not, I'm like, "This guy is paralyzed because he's so afraid of sharing what he's written that he thinks the solution is to rewrite it again."

• 1:24:34Speaker 01

  My.

• 1:24:34Rich Roll?

  And I was like, "Is this guy ever gonna, like, finish this thing?"

• 1:24:37Speaker 01

  So Cal.

• 1:24:38Rich Roll?

  So not knowing that that's what was really going on.

• 1:24:40Speaker 01

  So that, that was what was going on behind the scenes. And Cal and I made a promise. He was too, he's like, "Look, this is your book, I'm not gonna write a word of it." So you can't have that expectation. But the one thing I'll promise you is that if you send me something, I'll read it. And I'll let you know when it's good enough to move on to the next chapter. I was like, great. Now, to my surprise, like with Bill Gates, it took 134, you know, drafts for me to Cal go, all right, fine, move on. That's amazing. So some of the things, okay, so we have tension. That's what Cal taught. The second thing is there needs, needs, needs to be a grip.

• 1:25:24Speaker 01

  And that was the hardest thing for me to understand. And what he means by that is every chapter and every story, you can't just, you know, throw it out. So there's a chapter where I go to meet Mark Zuckerberg and it ends up being a disaster because security comes and they think I'm an imposter and they threaten to call the police and it's this whole crazy story. But I'll tell you, for example, the opening of that chapter is the founder of TED once told me, I live my life by two mantras. One, if you don't ask, you don't get. And two, most things don't work out. And that created this grip, or some people might call it a frame,

• 1:26:09Speaker 01

  to almost, and there's a sense of confidence that, you know, someone like Cal has over writing, that you really have to grab it like a slab of clay and hold, grip it in your hand and throw it down on the table. As opposed to just sort of being like, it was a bright summer day when I got the email from Mark Zuckerberg. That year, the story owns you. You need to own the story. So that's number two is grip it. And number three, which is a very practical one. And again, why the book took so long to write. This is the attention of detail Cal forced me, thankfully, to have with the writing of this book. Every sentence, he said, you need to treat like a restaurant.

• 1:26:50Speaker 01

  And every sentence, by the way, this is, this book is about 80,000 words. So we're looking at about 8,000 sentences, right? Maybe more, maybe less. And he goes, think of it like a restaurant. The first word is the mater diem.

• 1:27:10Speaker 01

  It invites you in. And then the pacing of that sentence needs to depend on what the mood is of the customer. Is it a straight through course? Is it fast food? Then you can't have commas in that sentence. Is it an a course meal like very extravagant? Then you can use commas and a semicolon, maybe an M. And you have this elegance to it. And then the final word is dessert. And if you, you can have the best mate or D, the best courses, but if the dessert is too salty, it's the worst restaurant you've ever been to. So every sentence of the book, you know, starting at the first word, no one will believe the amount Cal and I obsessed with.

• 1:27:53Speaker 01

  The first word we debated for months and we decided the best word is right. R I G H T. Right.

• 1:28:02Rich Roll?

  First word of the whole book.

• 1:28:04Speaker 01

  The whole book. The, the opening sentence is right this way. And that sets off the whole tone of the book.

• 1:28:11Rich Roll?

  Creates, yeah, it creates a tone.

• 1:28:13Speaker 01

  And the final sentence, oh my God. That was weeks of brainstorming because it had to be the perfect sentence. And what's the word that you end an entire story, you know, on? And it's the word home.

• 1:28:33Rich Roll?

  It's beautiful.

• 1:28:34Speaker 01

  Thanks, man.

• 1:28:35Rich Roll?

  So of all the people that you interviewed, all the wisdom that you collected.

• 1:28:41Speaker 01

  I don't know why we're laughing.

• 1:28:44Rich Roll?

  The most impactful was the guy who helped you write the book, it seems like.

• 1:28:52Speaker 01

  To you personally. Cal, yeah, it's crazy because I set off on this journey to learn from Bill Gates and to learn from Buffett and to learn from Spielberg. And while I did learn so much from them and what they taught me, you know, changed me forever. The greatest and most valuable thing that happened on this journey was both Cal Fussman and Elliot Bisno being like family.

• 1:29:19Rich Roll?

  So, let's talk about Elliot for a minute. I mean, this guy's become your mentor, sort of, right?

• 1:29:26Speaker 01

  This is my bet, and I'll say this on this podcast, I want to plant my flag in the ground. In 20 years, he will be one of the most, you know, impactful names in business. The only reason no one knows him right now is because he's purposely, by design, tried to avoid all, you know, public opinion and attention.

• 1:29:52Rich Roll?

  I can see that. I mean, I love Elliot and his wife. You know, Julie and I have become close with them, and I think the world of him, and I think what he's built is so extraordinary. You know, it's so extraordinary that like, I can't wrap my head around it, like, it doesn't make sense. And maybe a good way to kind of launch into this part of our conversation is like, I first became aware of, like, these summit people many years ago, a long time ago. A friend, a yoga teacher called up Julie and said, hey, I'm supposed to go teach this class at this house, these people, I can't do it, I gotta go, will you just fill in for me? And Julie wasn't like, really a yoga teacher at that time, but as a favor to a friend,

• 1:30:36Rich Roll?

  she said, sure, and here's the address, go to this. She goes to this house, and it's like, I don't know, 15 people there in Malibu. This was many years ago.

• 1:30:45Speaker 01

  Yeah.

• 1:30:46Rich Roll?

  I mean, this had to be 2002 or something, a long time ago. She comes back from that experience, and she's like, I don't know who these people were, and like, it was kind of weird, like, I'm in this house, and it's sort of like a commune, and I taught yoga to these people, and they were all like, so engaged, and like, friendly, and present, and... So much so that it like weirded me out like I'm like, what is happening? Like, I don't know what these people are doing, but there's something going on here. You know, and then I think it was a couple of months later where there was like a double page ad in Vanity Fair and they're all like walking down the beach together. And she's like, those are the people I thought you and that was my first introduction to what Summit is. And then I started to learn about what they were doing and, you know, I've now been to

• 1:31:28Rich Roll?

  Eden, these people like Elliot, you know, at, at, at, with Elliot at the helm, this group bought a mountain in Utah and they're creating this community and they host these annual events or biannual events, um, where they bring incredible speakers in and.

• 1:31:44Speaker 01

  Ah, Bezos was the, one of the best speeches I've ever seen in my.

• 1:31:47Rich Roll?

  And they cultivate this community around ideas. And I think it's truly remarkable. And I think Elliot is somebody whose heart is in this amazing place and the team that he's built is incredible. It's disheartening when you read press and it, they don't get it or it gets missed sort of, you know, they, they're portrayed in a way that, that is different than I think it, what is what, than what is real.

• 1:32:11Rich Roll?

  But I have nothing but the utmost respect for Elliot and, and what he's created.

• 1:32:15Speaker 01

  It's mind blowing.

• 1:32:17Rich Roll?

  And how he came into your life is a crazy story.

• 1:32:19Speaker 01

  Oh my, well, it's funny because we sort of touched on that moment a little when I was sharing, when I was in that CVS parking lot on the phone with Bill Gates, the chief of staff. He said two things, right? Get a book deal and go build momentum. So, you know, I had some thoughts on how to get that book deal or figure it out, but the word momentum, like what the, I'm 19, I'm like, what the fuck is momentum? And I remember going back to my room that night and just like literally my head in my hands, like momentum? And I'm just sitting there like rocking in my chair and I don't know how this happened. But you know, sometimes like just thoughts flurry in your mind when you're just in a panic.

• 1:33:05Speaker 01

  So I'm just thinking like momentum, like if I'm only like 5% of there for Bill Gates, I must be at like negative 20% with, you know, Bill Clinton or Richard Branson. And I'm like, wait.

• 1:33:18Speaker 01

  Bill Clinton, Richard Branson. Didn't someone tell me last summer that Richard Branson was on this cruise ship or something? It's almost like procrastinate. I take out my computer and I Google like Bill Clinton, Richard Branson cruise ship. And this article pops up and it's on Fast Company and it is like Summit Series takes the high seas with a cruise ship packed with Richard Branson, Gary Vaynerchuk, The Roots as the house band by the pool, Blake Mycoskie leading shark tagging, Tim Ferriss canoeing. Like it just, I was like, what the fuck is this? Right? It sounds like this, like, you know, entrepreneur's dream.

• 1:34:03Speaker 01

  And I'm reading this article and it's like Elliot Bisno, the founder and CEO of Summit Series with many companies to his name is 26 years old. And I'm like, what? 26 is like my cousin's age. Like, how is that possible? I thought you had to be like this big CEO. So I just start, I Google Elliot Bisno and I'm just ripping through it, going down this rabbit hole. And, you know, I missed like two meals without noticing and I'm just clicking and clicking. And the weird thing about him is that there was a lot of articles that mentioned him, but none that actually said what he did. So it was almost like I was this detective trying to piece it together. It's part of the whole mystique.

• 1:34:47Speaker 01

  Right. I learned later it's by design. And it's almost like Googling the guy from Catch Me If You Can. You think you're on to something and then you get thrown off. And so I'm Googling and Googling and by the end I'm like,

• 1:35:04Speaker 01

  if there is one person on earth who can, you know, teach me about momentum and show me what I need to do to get to Bill Gates, it has to be this guy. And I remember this night very vividly. I, you know, closed my eyes and said a prayer and then I opened my journal and I, at the top wrote, "Dream mentors." And I underlined it and on the first line I wrote Elliot Bisno.

• 1:35:37Speaker 01

  And a couple of weeks later, I was again studying for an accounting final this time, and I couldn't stop thinking about what it would be like to instead be learning from Elliot. So again, I can't focus on finals. So I just am like, all right, let me get it out of my head and out of my system. So open my computer and I start writing this email for Elliot. But I end up spending three hours writing what I think is like the perfect email. I use the Tim Ferriss cold email template. I email Elliot. I send it off and literally the next morning, he goes, great email. What are you doing Thursday? And I look at my calendar and Thursday is my accounting final. So I say the only thing that I can. I'm completely free. What do you have in mind?

• 1:36:23Rich Roll?

  And, and just to kind of put a, put a punctuation mark on this, your greatest skill might be finding all these people's emails somehow. Like, how are you doing?

• 1:36:34Speaker 01

  There's, there are surprisingly, a lot of very effective systems. But do you know what's crazy? Actually, this is wild. It was easier for me to find Bill Gates' email address than it was to find Elliot's.

• 1:36:50Rich Roll?

  Wow. So when you emailed Bill Gates, you were actually emailing Bill Gates? You weren't like emailing an assistant or something?

• 1:36:56Speaker 01

  No, but with people of this caliber, they have assistants who

• 1:37:01Rich Roll?

  Read their stuff.

• 1:37:02Speaker 01

  Read their stuff and filter out the junk. So what's left in his inbox is stuff for him. And so I got intercepted really quickly with Bill.

• 1:37:12Rich Roll?

  Anyway, yeah. All right. So somehow you get Elliot's email through some kind of cyber sleuthing. I don't know.

• 1:37:19Speaker 01

  Well, for Elliot's, actually, I can tell you the way I did it for him because I remember I couldn't, with all my methods, it didn't work. So with him, I was like, all right, I'm just gonna pick, you know, 10 of the likely things that might be it.

• 1:37:38Speaker 01

  And I just guessed.

• 1:37:40Rich Roll?

  You literally guessed it?

• 1:37:41Speaker 01

  I put them all in the BCC field. And one of them was the, I got nine bounce backs and one didn't bounce back. Ah, that's smart. So he ended up responding. And, you know, so I say, I'm completely free. And he says, great, meet me at this hotel. Um, I'm there for this conference in Long Beach. Um, and before you come, like, read a chapter of this book.

• 1:38:08Speaker 01

  And this is like my dream mentor. So if he says, read a chapter, I'm reading the whole book, right? So I read the whole book. I don't stay for my accounting final.

• 1:38:16Rich Roll?

  What was the book?

• 1:38:17Speaker 01

  It is unbelievable book. It's called, When I Stop Talking, You'll Know I'm Dead by Jerry Weintrup.

• 1:38:22Rich Roll?

  Mm hmm.

• 1:38:23Speaker 01

  Unbelievable book. And for anyone who's like an entrepreneur on their hustle, like, this is one of the greatest impresarios of the, you know, 20th century. It's his autobiography. And I go, I think, all right, it's not a big deal. Elliot's gonna meet with me for 15 minutes. My accounting final isn't until noon. It's only, the hotel's only an hour away from school. I can still make it on time.

• 1:38:52Rich Roll?

  Mm hmm.

• 1:38:53Speaker 01

  So what ends up happening is I show up the morning of, you know, 8:00 AM. I get there early. Elliot walks in right on time. Our 15 minute meeting turns into four hours. And I, it turns out that we're meeting at the Westin Hotel in Long Beach during TED, which is the main lodging of the TED conference. So I'm sitting at this breakfast room with, you know, everyone I, you know, Larry Page is sitting five feet away and then over there is Tony Hsieh, then over there is Reid Hoffman. And I'm 19 and I'm like, what? What? It's literally like The Wizard of Oz.

• 1:39:36Rich Roll?

  Right.

• 1:39:36Speaker 01

  From black and white to color. And my four hour meeting with Elliot turned into an entire summer traveling the world with him to now him being one of my best friends.

• 1:39:47Rich Roll?

  That's amazing. And what do you think you said or impressed upon him in that meeting that,

• 1:39:56Rich Roll?

  that clicked with him?

• 1:40:03Speaker 01

  I think, and you know, there's no way to know for sure. But I think when it comes to having a mentor, they can only help you as much as you're willing to help yourself. So I knew that everything Elliot would advise me to do, I'm gonna go, you know, 10x. So, you know, he says, hey, can you read this chapter for me? I'm gonna read the whole book. He says, hey, I remember when we had first met, like, I didn't have any, you know, I was 19, I didn't have like a debit card or a credit card or anything. And he is like, you fucking idiot. How do you expect to be traveling around without a... So, you know, the next morning I opened up,

• 1:40:45Speaker 01

  like, you know, I just did everything he advised, you know, to the 10th degree. And what, you know, my theory is that when someone like yourself or like Elliot, who, you know, has very limited time, if you're gonna invest in a young person, you wanna make sure there's some, you know, in addition to doing it out of the kindness of your heart, you wanna make sure there's an ROI that, that advice you're giving is actually going somewhere. And with Elliot, everything he told me, you know, I ran with it. And, you know, it started small and it got bigger and bigger and bigger to the point where it's now not only a mentor relationship, he,

• 1:41:30Speaker 01

  he was standing at my dad's bedside when he took his final breath. So he's very much like family.

• 1:41:35Rich Roll?

  Wow. That's amazing. You know, I think it's pretty rare, I mean, you have Cal Fussman and Elliot as like, you know, on your speed dial, as this kid, I mean, you're, I think your talent really is your people skills, you know, your ability to connect with other human beings.

• 1:41:56Speaker 01

  I appreciate that, man.

• 1:41:57Rich Roll?

  I know that that's been the history of our relationship. And I don't know how much of that is teachable versus just the way you're baked.

• 1:42:06Speaker 01

  Hmm. So first of all, I appreciate that. I've thought a lot about, you know, what things I can pull out that I've learned along the way. And...

• 1:42:19Speaker 01

  You know, I've made a ton of mistakes. So while my relationship with, you know, you or Elliot or Cal is great, you know, there are some relationships that I've completely fucked up on. You know, to the point where I'm like blacklisted from some people's, well, I might be on Elliot's feed, I'm blacklisted from some people's.

• 1:42:36Rich Roll?

  It's like this crazy guy just won't stop emailing me kind of thing.

• 1:42:39Speaker 01

  Right, so with, so like Warren Buffett, for example, I spent, like I told you, I spent this eight month quest, you know, trying to track him down and I spent literally eight full months, it wasn't part time. You have to understand, every morning waking up, I'd put in my headphones at 6 a.m., run down the sidewalk, imagining Warren Buffett was at the end as I'm doing my sprints, like obsessive. And I would write handwritten letters to him that I would take weeks editing and I'd handwrite these letters and mail it to him and he would actually handwrite some responses back. So it was this like very awkward pen pal situation.

• 1:43:16Rich Roll?

  Thank you, Alex.

• 1:43:17Speaker 01

  Thank you, Alex, go away. He was much kinder, but that was essentially what it said. And I just kept every week calling Buffett's assistant, week after week after week. And it almost felt like I was in this, you know, boxing, you know, world championship with, you know, this young kid who's never picked up boxing gloves versus, you know, Floyd Mayweather. And I'm just getting pounded in the gut, punched in the face, you know, I'm bloody, I'm spitting up blood, you know, my insides are bruised and, you know, each rejection felt like I'm just getting pounded. And by the end of these eight months, you know, I had flown to Omaha, I had sent so

• 1:44:00Speaker 01

  stupidly Buffett a shoe to try, you know, I did all these crazy things where at the end of the eight months.

• 1:44:06Rich Roll?

  Why'd you send him a shoe?

• 1:44:07Speaker 01

  Oh, this is a very embarrassing story.

• 1:44:12Speaker 01

  We, so someone who was advising me, who had said he worked for Buffett was like, "Trust me on this. They'll think it's funny." And I was like, "Are you sure?"

• 1:44:29Speaker 01

  I can go in, it's a whole nother. All right, forget it. It was a misfire. It was a giant misfire, but pretty much I kept pounding, because I just believed every business book says persistence is the key to success. So I thought the more I pounded on the door, the sooner I'll break it down. Yeah, there's a limit to that. But ultimately, you end up bum rushing his shareholders meeting, right? Correct. So I end up- Did you get tossed out? Oh my, okay, so for that, what ended up happening was, you know, after this eight months, Buffett's assistant, you know, she knew me. She, I had sent her flowers. It's Alex again. Right, yeah, she knew who I was. And she, I think, felt bad for me, and she goes,

• 1:45:10Speaker 01

  "Look, I know Warren. I know he's not gonna say yes. So why don't, you know, as my guest, you come to the shareholders meeting?" And I was like, "Oh my God, like, thank you so much. Do you think I can bring some friends?" She's like, "Of course." So she sends me six tickets. And when I'm on the phone with her, I'm like, "Hey," her name is Debbie, I'm like, "Hey Debbie, isn't it true that people at the shareholders meeting and the audience can ask Warren Buffett questions?" And she goes, "Alex, Alex, Alex, I know what you're trying to do, but it's just not possible. There's 30,000 people there and only 30 ask questions. Your odds are one in a thousand. I wouldn't get your hopes up."

• 1:45:53Speaker 01

  But Debbie doesn't know, I'm the king of hopes up. And you're also the guy who figured this out with The Price is Right. All right. So you're gonna do- So I'm like, you know- Apply your Price is Right tactics to- So what's funny is it actually was very similar to The Price is Right, in the sense that it's advertised as this lottery luck system, but there's a system-

• 1:46:18Speaker 01

  And the odds aren't exactly the same. So me and my, you know, five childhood best friends, you know, again, Kevin is with me. We go there. We end up finding a loophole in Buffett's lottery system. And out of the six of us, although the odds were one in a thousand, four got winning lottery tickets. And that's how I asked Buffett my questions.

• 1:46:39Rich Roll?

  And the question was?

• 1:46:40Speaker 01

  Um, so there was four different questions. One was about raising a fund. Another one was about negotiating skills. Another one was about, um, you know, value investing. Another one was about how he focuses his time, but.

• 1:46:54Rich Roll?

  But like straight up questions. You didn't get up and say, hey, it's Alex.

• 1:46:58Speaker 01

  No, no, no, no. My thinking was, look, you know, I have, let's say 20 questions I wanted to ask him in an interview. All right, let me take the top four and ask them in front of 30,000 people. What ended up happening is, you know, Buffett, I think, caught on to what was happening. And by the time my fourth friend went up, the spotlight turned on. Buffett saw my, my fourth friend and goes, well, this is a great time to end the shareholders meeting. Thank you for coming. And, you know, who knows what, if he knew what he was doing, but the, it was a.

• 1:47:34Rich Roll?

  Right.

• 1:47:35Speaker 01

  Very cra- this, and my friend, as he started asking the question, the microphone got cut off.

• 1:47:40Rich Roll?

  Right. So Debbie's like in his ear. But you sent him this, right? Tell me that you sent him the book.

• 1:47:48Speaker 01

  I haven't sent it.

• 1:47:49Rich Roll?

  How could you not have sent this to him with a, with a note saying like?

• 1:47:53Speaker 01

  I think it'll fall into his hands eventually. I, I don't want to like rub it in his face. But what ended up happening after the shareholders meeting was I ended up interviewing Bill Gates. And the interview with Gates went so well that his office was like, look, how can we help this mission? And I was like, well, I still really would like to sit down with Warren Buffett. And they go, easy. They contact Buffett's office. And I'll never know what was said, but I do know that Gates.

• 1:48:22Rich Roll?

  That guy?

• 1:48:23Speaker 01

  Yeah. Essentially what my assumption is they're like, we know all about Alex. We're not doing this.

• 1:48:30Rich Roll?

  Right.

• 1:48:31Speaker 01

  And Gates's office sent me an email, like very terse. Please no more contact to Buffett's office. Thanks.

• 1:48:39Rich Roll?

  Whoa.

• 1:48:40Speaker 01

  And, and they're like my buddy. You're like, they're.

• 1:48:42Rich Roll?

  Right.

• 1:48:43Speaker 01

  We're friends. So I was like. Oh my God. And what I learned, finally, I learned my lesson that there's a such thing as overpersistence. You know, you can bang on a door so much that they'll call the police. And no business book talks about that. No one talks about the dangers of overpersistence. And I realized I had dug myself into such a deep hole that even Bill Gates couldn't pull me out.

• 1:49:10Rich Roll?

  Yeah, you need, I mean, that level of, you need, you need EQ, you need emotional intelligence to be able to read those cues and understand where those lines are.

• 1:49:19Speaker 01

  Well, I

• 1:49:21Rich Roll?

  It's like, exuberance got the best of you with that one, I think.

• 1:49:23Speaker 01

  Yeah.

• 1:49:24Rich Roll?

  Good lesson to learn. So, in, in the, in the wake of all of these people, you know, Lady Gaga, Spielberg, Maya Angelou, Wozniak, Jessica Alba, Pitbull. I was like, I'm too old to like, understand that one.

• 1:49:38Speaker 01

  Dude, that one, it was a good interview.

• 1:49:40Rich Roll?

  So, we don't have time to talk about all these people, but is there, I guess my question is, like, what is the through line? Like, what is the consistent, you know, piece of advice? Or what is it that, that unites all of these people that you talk to? If you could like, condense that down into some wisdom that the person who's listening to this, or who's gonna read this book, is gonna take away with them?

• 1:50:06Speaker 01

  When I had started out on the journey, I was very cognizant of, I'm not looking for this, you know, one silver bullet. You know, we've all seen those TED Talks or those business books, you know, the one key to success. And I sort of roll my eyes. What ended up happening was, as I went on the journey, you know, do these interviews, and on the outside, you know, Bill Gates and Maya Angelou could not be more different. Right? Like, Maya Angelou grew up in rural Stamps, Arkansas, Gates, you know, a wealthy suburban Seattle, to a rich lawyer, and

• 1:50:47Speaker 01

  You know, I just kept doing these interviews. And about like 70% of the way into them, I started realizing that almost like a good musical album, there was like a common melody to every interview. And the analogy that came to me, because I was, you know, 21 at the time, was that it's sort of like getting into a nightclub. So what I realized is life, business, and success, it's just like a nightclub. There's always three ways in. There's the first door, the main entrance where the line curves around the block. And that's where 99% of people wait in line, hoping to get it. You know, you're standing there with your resume. There's the second door,

• 1:51:32Speaker 01

  the VIP entrance, where the billionaires and the celebrities go through. And school and society have this way of making you feel like those are the only two ways in. You're either born into it, or you wait your turn like everybody else. But what I've learned, and what you know very well, is that there's always, always, the third door. And it's the door where you jump out of line, run down the alley, bang on the door 100 times, crack open the window, go through the kitchen. There's always a way in. And it doesn't matter if that's how Gates sold his first piece of software, or how Lady Gaga got her first record deal. They all took the third door. So that's not only the title of the book and the thesis of the book, but that's really the energy I'm trying to inject into the next generation.

• 1:52:14Rich Roll?

  It's another way of saying, you have to think creatively and out of the box. Like, there's always, there's always a solution that's not immediately self-evident, if you're willing to experiment and explore, and, you know, be unconventional in your approach.

• 1:52:29Speaker 01

  And grab life by the collar, you know, roll up your sleeves, get messy, get dirty. There's always, always a way.

• 1:52:37Rich Roll?

  But I would say this to you, young Alex Banayan. Not everybody is cut out to go through that third door. Some people are just wired to, you know, they're better off in line, waiting to go through the front door.

• 1:52:56Speaker 01

  What I've learned is that...

• 1:53:00Speaker 01

  And something that I had to learn along the way is that taking the third door isn't always about, you know, yelling, "Stan, your scarf!" You know, that's what worked for me. You can look at Chi Lu, for example. He's one of the most fascinating people I'd ever interviewed in my life. He grew up in a-

• 1:53:20Rich Roll?

  He's this Chinese guy, right? Yeah.

• 1:53:22Speaker 01

  He grew up in a village outside of Shanghai, China, with no running water, no electricity. People were so poor that they walked around with deformities from malnutrition. For every, you know, we think our education system's bad in America, for every 300 students, there was one schoolteacher. So those are the circumstances he was born into, and he's, you know, very quiet. You know, he was smart, so he worked very hard, and by age 27, he was making the most money he had ever made in his life: $7 a month. Fast forward 20 years later, and he's a president at Microsoft.

• 1:54:04Speaker 01

  And his story is, and you know, throughout the book, there's a lot of people who, you know, aren't these extroverts, who are very introverted, who are very quiet, who do like to stay in line, but the third door isn't about, you know, being wild and loud, or, you know, being crazy and creative. It's about doing whatever it takes to find a way, and taking your life in your hands, and making sure that you're gonna do everything you possibly can to make it happen.

• 1:54:37Rich Roll?

  First, you gotta figure out what that is.

• 1:54:41Speaker 01

  Yeah.

• 1:54:42Rich Roll?

  You know? That's the struggle you went through. You know, I can't help but listen to you and try to think how that relates to my own life experience, and of course, you know, I struggled for a long time trying to figure out what I wanted to do, and, you know, I'm sitting here with you today only because I had to figure out my version of the third door, which was a door into a room that, you know, I don't know that there were too many people in. You know, it's like, it's not like I'm trying to break into a room where there's a bunch of people already there. It's like I'm trying to find a path to something that I don't even know exists. Like, there's no template for it, like, learning as you go. But I think I always bring it back to-

• 1:55:27Rich Roll?

  That internal journey of like trying to really figure out what it is that I'm trying to express in the most honest way possible. So that before you start trying to break down the third door, you want to make sure it's the right third door.

• 1:55:45Speaker 01

  Yeah, absolutely.

• 1:55:47Rich Roll?

  So how do you think you figured that out for yourself?

• 1:55:50Speaker 01

  Well, Elliot told me this great quote once. He said, "Sometimes going down the wrong path leads you to the right one." And I think that's very true, but that's only if you're paying attention and you're listening.

• 1:56:04Speaker 01

  For me, when I started with this book, it was never to be an author. It was, you know, I wanted to find out this information, share with my generation, move on to what I actually wanted to with my life.

• 1:56:18Speaker 01

  For me, as this journey has unraveled, I've realized that in many ways,

• 1:56:26Speaker 01

  it's so closely tied to what I feel my purpose is. And again, I didn't, it's not this overnight realization.

• 1:56:35Speaker 01

  I'll tell you this story that I heard once. It's this woman, she's teaching in Baltimore for Teach for America in this really, you know, tough school.

• 1:56:46Speaker 01

  And she's teaching, you know, young kids, you know, eight years old.

• 1:56:51Speaker 01

  And, you know, it's just they're in a really tough neighborhood. So she decides one day she's not going to do the math lesson. She's going to, um, I think, you know, grab some paper and some crayons and help them

• 1:57:05Speaker 01

  write and draw their biggest dream in life. So she passed out the paper and the kids are running and, you know, coloring and everyone's having a lot of fun. And then there's this one kid in the back who like is frozen.

• 1:57:17Speaker 01

  And she's watching him and about halfway through, he has this idea and starts coloring a picture. And at the end of the lesson, you know, she collects the papers and at the end of the day, she's flipping through them and sees that he drew a pizza delivery man.

• 1:57:31Speaker 01

  And she calls the mother that night because she was concerned. And the mother wasn't surprised. The mom said, "The only man in his life who's not on drugs or in jail is his uncle who delivers pizza." And what that story showed me is that

• 1:57:52Speaker 01

  Young people will always strive for the highest branch they see possible. It's our jobs as society to illuminate those branches. And in many ways, when I had started this book, you know, we talked about how I wanted it to be, you know, very informational, like, you know, Q and As. And while there's still a ton of practical and tactical lessons and tools in the book, I've learned that you can give someone all the best tools and knowledge in the world and their life can still feel stuck. But if you change what someone believes is possible, they'll never be the same. And that's very much what my purpose is with this book.

• 1:58:31Rich Roll?

  Yeah, I believe that. That's a good purpose to have.

• 1:58:33Speaker 01

  Thanks, man.

• 1:58:34Rich Roll?

  You know, I think what's interesting about you, you know, one of the things we kind of didn't even get to, we glossed over, is the fact that like, you know, part of your story is that at 19, you become this venture capitalist. You get hired by a VC firm, you're like the world's youngest venture capitalist. It gets a lot of press, there's articles about you in like Fortune and stuff like that. You make the Forbes like 30 under 30. My question for you is, I mean, ultimately, you made this choice to like not do that anymore so that you could finish this book. I would imagine there were a couple of people who told you that's crazy, that you had this, you know, burgeoning career as a successful venture capitalist.

• 1:59:14Rich Roll?

  Like, why did you, how did you make that decision to walk away from that?

• 1:59:20Speaker 01

  So the book is actually what led me to the VC job. And when I first joined the VC firm, and they're incredible people, they knew from day one, when I started working with them, that the book was my number one priority. So it wasn't really this like shocker plot twist as much as them saying, you know, thank you for all you've done, it feels like now's a good, because it got to the point where...

• 1:59:55Speaker 01

  You know, my book was always my number one thing. And something can be your number one, taking 80% of your time. But it sort of becomes unfair to that number two. So I still love Venture, and I think it's fascinating. And my time with Alsoft Louis Partners was incredible. But to me, it was a very obvious decision of my heart is this book. My heart is this mission. And Venture was this great opportunity along the way.

• 2:00:32Rich Roll?

  Right. And what's really insane about how this is unfolding is that you're going off and like giving keynotes at Nike, IBM, Apple, Harvard. And essentially, from what I can tell, this keynote is all about like The Third Door, this book which hasn't even come out yet. Like, okay, let's say the book comes out, it does huge, then you go to talk to Apple. It's like, how are you like?

• 2:01:02Speaker 01

  You just hit on my biggest mystery in my life.

• 2:01:04Rich Roll?

  And as somebody who's like, you know, been doing this for a little while, I'm like, I haven't spoken at Apple or IBM or Harvard. Like, what are you, how are you doing this? What's going on? How can I learn from you? Like, Alex, will you be my mentor?

• 2:01:22Speaker 01

  You're way too smart for that. It's crazy, because when I was, I think I was maybe nine, I was 20 when I got my first like corporate speaking engagement. It was with Nike. And, you know, I had like talked a little before about the book, they're all free things. I like a startup thing or this entrepreneur thing.

• 2:01:51Rich Roll?

  It's the two-year promotional tour for the book.

• 2:01:55Speaker 01

  Which turned to seven-year promotional tour for the book.

• 2:01:59Speaker 01

  What's been very fascinating to me is, you know, I started out writing this book, really initially, just with my friends in mind. You know, we're going through this life crisis. We don't know what we want to do with our lives. We don't know how to break through. I'm going to write this for us. And I had mentioned this slightly before, which is, I learned that the book is less about a specific age than a stage. And I learned that through corporate speaking, where these big corporations would reach out to me, which I, you know, it wasn't like I was pounding the phones for corporate gigs, because I was pounding the phones trying to get to Bill Gates. My focus was on finishing this book. What I realized is that there's

• 2:02:41Speaker 01

  tremendous value in not only stories that inspire risk-taking, but also someone coming in to help break down the science of it. And that's what I've been doing with a lot of these big corporations, which is going in and really decoding the art of risk-taking for them. You know, breaking down the steps, also telling crazy stories along the way. And obviously, I think it's going to be a lot more fun when they can actually hold the book, you know, starting, starting now. But over the past few years, these keynotes have been even surprising to me of how well they've gone, because I didn't understand,

• 2:03:20Speaker 01

  because I've never worked in a big corporation, how hungry they are for that kind of energy and that kind of insight. Because we've talked about it, sometimes it gets very, you know, linear there, where there's a lot of bureaucracy and innovation only happens with risk-taking. And I didn't know this at the time, but this book, in many ways, is an entire study on risk-taking. You know, how Bill Gates dropped out of school and started Microsoft. You know, how Spielberg, you know, snuck onto the Universal lot to become the youngest director. All these crazy stories. In the end.

• 2:03:59Rich Roll?

  Well, baked into your, your story, you know?

• 2:04:02Speaker 01

  Right.

• 2:04:02Rich Roll?

  Right? Which is your own risk-taking adventure and journey to this point.

• 2:04:07Speaker 01

  Or in my mom's words, how I made her life a hell for the past seven years.

• 2:04:12Rich Roll?

  But they're good now, right?

• 2:04:13Speaker 01

  Yeah.

• 2:04:14Rich Roll?

  All right. Well, we got to wrap this up, but I don't want to end it without, um, I think a good place to kind of land the plane is to talk a little bit about your relationship with your dad who passed away this past year. And, you know, I know you're somebody who's very close to your family. So I'm interested in, you know, how that process, um, of letting go and kind of being there when he was passing, how that's informed your perspective on your career, your life, ambition, what's important and what's not.

• 2:04:52Speaker 01

  It was, you know, it goes without saying, the hardest thing I've ever gone through in my life.

• 2:04:59Speaker 01

  Not only the dying process, but there's something, it's,

• 2:05:08Speaker 01

  there's something very life-altering to see the person who gave you life, like in front of you, taking his final breath.

• 2:05:19Speaker 01

  And

• 2:05:24Speaker 01

  what I've learned

• 2:05:27Speaker 01

  is what matters in the end.

• 2:05:34Speaker 01

  It's weird to almost like couch this into the story of what we're just talking about because I, when I was starting out,

• 2:05:42Speaker 01

  I think it was this like subconscious belief that at the end of life, you know, if you really succeed, if you do it really well, there's almost this like trophy at the end.

• 2:05:51Speaker 01

  And if you do very poorly, you know, you get punished. And

• 2:05:59Speaker 01

  You know, my dad had pancreatic cancer for 14 months. Or he probably had it for longer, but from when we found out of his diagnosis to when he passed was a 14-month period, where it was pretty much 14 months of me sitting with death every single day, you know, going with my dad to the chemo ward, sitting down with the hospice people, reading on grief and grieving, you know, really. Yeah, I'm the one who told my dad he had three months to live. When you spend that much time with death, you learn how to live. And you find out what matters in the end, you know?

• 2:06:41Speaker 01

  For the final, about Wednesday, Thursday, Friday, Sunday, for the final five days of my dad's life, he had no access to anything that today, like, if he was alive, he would count as giving him pleasure. You know, food, he loved food, he couldn't eat, he couldn't drink, he couldn't talk. My dad loved to talk, he loved to go out, he couldn't do that, he couldn't, he loved to like, watch TV, he couldn't open his eyes, he had no access to money, possessions, literally every material pleasure was gone for those final five days. And

• 2:07:22Speaker 01

  I remember the day he first slipped into his coma, where I was at Elliot's apartment. It was a Wednesday morning, and I got a call from my dad's doctor saying she had just visited him at home, and it looked like he had just a couple of days left to live. And though, it's very hard to describe what that feeling is, because it's not like a cognitive moment, it's not a, you're not thinking of like, alright, what to do, it becomes, and although you know that call was coming at some point, it's one of those things that once you hear it, like, everything changes.

• 2:08:06Speaker 01

  So I called my sister who lived not too far away. I like picked her up in the car. We went to go visit my dad at my parents' house. And we get in there and I see my dad and my mom and my dad's caregiver, because he was on hospice, in the living room. But my dad visibly did not look the same. I had seen him, you know, a day earlier, two days earlier, where he was moving around and talking. And he was very still and his skin had yellowed. And his breathing was very labored. And I remember like trying to, you know,

• 2:08:49Speaker 01

  touch his hand and see if he was resting and definitely wasn't resting.

• 2:08:56Speaker 01

  And I remember sitting on the couch with my sister, looking at my dad and,

• 2:09:04Speaker 01

  you know, realizing slipping into a coma.

• 2:09:11Speaker 01

  And a few minutes later, my dad's caregiver said it was like time for him to take his pain medication. Because with pancreatic cancer, it's very painful. It's literally like, imagine like a football growing inside of your abdomen. So all those nerve endings are being squeezed. So I knew if he didn't take his pain medication.

• 2:09:31Speaker 01

  And he had slipped into the coma very rapidly. So there wasn't time to get like an IV in him or something because he was at home on hospice. So he had to take this pain medication. So that, you know, the caregiver's trying to give it to him and she's saying, "David, please, open your mouth." And he's unresponsive.

• 2:09:49Speaker 01

  And, you know, she's asking over and over and over again. And I'm really panicked. And then my mom stands up and she like kicks off her shoes and grabs the pill in her hand and like kneels down on the floor.

• 2:10:04Speaker 01

  And I remember like seeing her. I'm sitting on the couch and she's kneeling down and she puts her hand on my dad's hand.

• 2:10:15Speaker 01

  And the second she opened her mouth, asking him to open his mouth, his mouth opened seamlessly.

• 2:10:29Speaker 01

  He took the pill and swallowed it very easily. And I remember just sobbing in that moment. Not out of sadness, because I wasn't sobbing when I saw him in the coma. I was scared when I saw him in the coma. But in that moment, I was sobbing out of like the beauty of it. And what I had learned that day is that, and I remember writing that down that night, was that like at the end of life, when you don't have, you know, access to money or possessions,

• 2:11:05Speaker 01

  all you have is your breath, your heartbeat, and your connection to those you love. And that's, you know, probably the biggest lesson my dad's ever taught me.

• 2:11:19Rich Roll?

  And how have you carried that into how you live your life now?

• 2:11:25Speaker 01

  You know, if my dad didn't pass, and this sounds weird, because I am, you know, working as hard as I can on this book launch, because I care about it so much, but I would probably be doing it and being a lot more tightly wound and probably miserable. Because what I learned is that, look, I want this, look, this is, this book is my dream. You know, I spent seven years on it. I want it to, you know, do as best as it possibly can and touch as many lives as it possibly can. But I also, I saw the end. I know what, when I'm dying, it doesn't matter if I'm a bestselling author.

• 2:12:07Speaker 01

  It doesn't, and truthfully, it doesn't even matter how many lives I've touched. While that does matter to me personally, in the end, what matters is if the ones you love are like sitting behind you, beside you. And it's shifted the priorities to the point where, you know, again, if my dad hadn't passed, you know, Mother's Day is this month and Father's Day is next month, like I probably would have been like, guys, I can't, I gotta stay at the office. It's a no-brainer for me to take the entire day off. Forget about having a Mother's Day breakfast, it's a Mother's Day day.

• 2:12:49Speaker 01

  It's helped re-prioritize in a very major way that no, no lesson from Bill Gates ever could have given me.

• 2:12:57Rich Roll?

  Yeah, I mean, I'm just sitting here thinking, well, this is the most powerful, you know, lesson that you've learned in this seven-year exploration.

• 2:13:05Speaker 01

  Yeah, and it's crazy. He passed away as soon as the book was done, like.

• 2:13:12Rich Roll?

  And he was, he had his wits about him enough to know what you were doing and everything.

• 2:13:17Speaker 01

  Yeah.

• 2:13:21Rich Roll?

  Well, I think that's a good place to end it, my friend.

• 2:13:23Speaker 01

  Thank you, man. I appreciate it.

• 2:13:24Rich Roll?

  Yeah, it's powerful. I'm super proud of you. You stuck with it. The book is amazing.

• 2:13:33Speaker 01

  Thank you, man.

• 2:13:33Rich Roll?

  You did an incredible job, and I think it does have the potential to impact a lot of people. So I can't wait to see it out in the wild.

• 2:13:42Speaker 01

  Me too, man.

• 2:13:42Rich Roll?

  I want to see it in the airport, next time in the airport, and anything I can do to help you, man.

• 2:13:48Speaker 01

  It means a lot.

• 2:13:49Rich Roll?

  Yeah, much love, Alex.

• 2:13:50Speaker 01

  Thank you.

• 2:13:51Rich Roll?

  Cool. So The Third Door, you can pick it up wherever you buy fine books, independent booksellers, Amazon, all those good places. Are you doing any talks that are open to the public or book signings or anything like that?

• 2:14:03Speaker 01

  Yeah, absolutely. It's on my book website. So it's thirddoorbook.com, T-H-I-R-D, thirddoorbook.com. Yeah, all the tour stuff's on there.

• 2:14:13Rich Roll?

  Are you doing like a full tour, you know, in a multi-city kind of thing? You're going to do that?

• 2:14:17Speaker 01

  Yeah.

• 2:14:17Rich Roll?

  Yeah, cool.

• 2:14:18Speaker 01

  It's gonna be really fun.

• 2:14:19Rich Roll?

  Awesome, man. All right, we'll come back and we'll talk some more.

• 2:14:23Speaker 01

  Thank you, man. This was really, really enjoyable. I appreciate it.

• 2:14:25Rich Roll?

  Cool.

• 2:14:26Speaker 01

  Peace.

• 2:14:30Rich Roll?

  What do you know, people? It's over, it's done, we did it, and it was good. This officially concludes episode 370 with Alex Banayan. Hope you guys enjoyed that. Do me a favor, give Alex a high five on the social networks. He's @alexbenayan on Twitter and Instagram.

• 2:14:47Rich Roll?

  Pick up The Third Door wherever you buy fine books. There's a link in the show notes, a nice hyperlink to do that very thing. And speaking of show notes, check them out on the episode page at ritual.com. Why? Because we put a lot of work into them. They're almost like a syllabus to extend your learning, your edification, your entertainment beyond the conversation. And simply because they are awesome. Don't forget to pick up a copy of the Plant Power Way Italia, or the new edition of Finding Ultra if you haven't already. And if you're looking for more extensive nutritional direction, check out our meal planner, the Plant Power Meal Planner. It's at meals.ritual.com. We have thousands,

• 2:15:28Rich Roll?

  literally thousands of plant-based recipes. Everything is super customized based on your personal preferences, your allergies, your budget, how many people are you cooking for, what foods do you like, do you not like? We have unlimited grocery lists, even grocery delivery in most US cities, with international delivery in certain cities coming very soon. You get all of this for just $1.90 a week when you sign up for a year. People who have been using this, it's been a little over a year since we launched this product. It's been super popular. Everybody really enjoys it. It just makes plant-based eating super convenient as well as delicious. So for more on all this, go to meals.ritual.com or click

• 2:16:09Rich Roll?

  on Meal Planner on the top menu at ritual.com. And if you would like to support my work, it's easy. Just share this show with a friend or on social media. Subscribe to the show on Apple Podcasts or on whatever platform you enjoy this content. Subscribe to my YouTube channel. This episode is on YouTube in video format for the Visually Inclined, youtube.com/richroll. Subscribe if you're enjoying the videos. All of this just helps with the show's visibility, extending reach and audience. And all of that helps me to, in turn, book the very best people for future shows. You can also support the show and my work on Patreon at ritual.com/donate.

• 2:16:50Rich Roll?

  And as always, I want to thank everybody who helped put on this show today because I do not do this alone. It is a team effort. Jason Camiolo for audio engineering, show notes, production, interstitial music. Blake Curtis and Margot Lubin for the video work and the editing and the graphics and theme music, as always, by Analemma. Thanks for the love, you guys. See you back here in a couple of days. Until then, find that third door busted open, walk through, realize your dreams. Peace. Plants. Namaste.