#238 Jay Z: Decoded

What I learned from reading Decoded by Jay Z. ---- Get access to the World’s Most Valuable Notebook for Founders at Founders Notes.com ---- [1:39] I would practice from the time I woke in the morning until I went to sleep [2:10] Even back then I though I was the best. [2:57] Bourdain: The Definitive Oral Biography (Founders #219) [4:32] Belief becomes before ability. [5:06] Michael Jordan: The Life (Founders #212) [5:46] The public praises people for what they practice in private. [7:28] Lock yourself in a room doing five beats a day for three summers. [7:50] Sam Walton: Made In America (Founders #234) [9:50] He was disappointed in the world, so he built one of his own — from Steven Spielberg: A Biography (Founders #209) [12:47] The Pmarca Blog Archive Ebook by Marc Andreessen (Founders #50) [13:35] I'm not gonna say that I thought I could get rich from rap, but I could clearly see that it was gonna get bigger before it went away. Way bigger. [21:10] Over 20 years into his career and dude ain’t changed. He’s got his own vibe. You gotta love him for that. (Rick Rubin) [21:41] Against The Odds: An Autobiography by James Dyson (Founders #200) [25:27] I believe you can speak things into existence. [27:20] Picking the right market is essential. [29:29] All companies that go out of business do so for the same reason – they run out of money. —Don Valentine [29:42] There are two things in business that matter, and you can learn this in two minutes- you don’t have to go to business school for two years: high gross margins and cash flow. The other financial metrics you can forget. —Don Valentine [31:54] I went on the road with Big Daddy Kane for a while. I got an invaluable education watching him perform. [33:12] Everything I do I learned from the guys who came before me. —Kobe [34:15] I truly hate having discussions about who would win one on one or fans saying you’d beat Michael. I feel like Yo (puts his hands up like stop. Chill.) What you get from me is from him. I don’t get 5 championships without him because he guided me so much and gave me so much great advice. [34:50] Steve Jobs: The Exclusive Biography (Founders #214) [37:20] This is a classic piece of OG advice. It's amazing how few people actually stick to it. [38:04] Nuts!: Southwest Airlines' Crazy Recipe for Business and Personal Success(Founders #56) [39:04] The key to staying on top of things is to treat everything like it's your first project. [41:10] The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley (Founders #233) [44:46] We (Jay Z, Bono, Quincy Jones) ended up trading stories about the pressure we felt even at this point in our lives. [45:22] Competition pushes you to become your best self. Jordan said the same thing about Larry Bird and Magic Johnson. [46:43] If you got the heart and the brains you can move up quickly. There's no way to quantify all of this on a spreadsheet, but it's the dream of being the exception. [52:26] He (Russell Simmons) changed the business style of a whole generation. The whole vibe of startup companies in Silicon Valley with 25 year old CEOs wearing shell toes is Russell's Def Jam style filtered through different industries. [54:17] Jay Z’s approach is I'm going to find the smartest people that that know more than I do, and I'm gonna learn everything I can from them. [54:49] He (Russell Simmons) knew that the key to success was believing in the quality of your own product enough to make people do business with you on your terms. He knew that great product was the ultimate advantage in competition. [55:08] In the end it came down to having a great product and the hustle to move it. [56:37] Learn how to build and sell and you will be unstoppable. The Almanack of Naval Ravikant: A Guide to Wealth and Happiness (Founders #191) [58:30] We gave those brands a narrative which is one of the reasons anyone buys anything. To own not just a product, but to become part of a story. [59:30] The best thing for me to do is to ignore and outperform. [1:01:16] Poor Charlie's Almanack: The Wit and Wisdom of Charles T. Munger. (Founders #90) [1:06:01] Tao of Charlie Munger: A Compilation of Quotes from Berkshire Hathaway's Vice Chairman on Life, Business, and the Pursuit of Wealth With Commentary (Founders #78) [1:08:42] Jony Ive: The Genius Behind Apple's Greatest Products(Founders #178) [1:11:46] Long term success is the ultimate goal. [1:12:58] Runnin' Down a Dream: How to Succeed and Thrive in a Career You Love - Bill Gurley [1:15:11] I have always used visualization the way athletes do, to conjure reality. [1:18:14] The thing that distinguished Jordan wasn't just his talent, but his discipline, his laser-like commitment to excellence. [1:19:42] The gift that Jordan had wasn't just that he was willing to do the work, but he loved doing it because he could feel himself getting stronger and ready for anything. That is the kind of consistency that you can get only by adding dead serious discipline of whatever talent you have. [1:21:37] when you step outside of school and you have to teach yourself about life, you develop a different relationship to information. I've never been a purely linear thinker. You can see it to my rhymes. My mind is always jumping around restless, making connections, mixing, and matching ideas rather than marching in a straight line, [1:27:41] Samuel Bronfman: The Life and Times of Seagram’s Mr. Sam (Founders #116) [1:34:15] The real bullshit is when you act like you don't have contradictions inside you. That you're so dull and unimaginative that your mind never changes or wanders into strange, unexpected places. [1:36:25] There are extreme levels of drive and pain tolerance in the history of entrepreneurship. [1:38:45] Hit Men: Power Brokers and Fast Money Inside the Music Business [1:42:24] I love sharp people. Nothing makes me like someone more than intelligence. [1:44:17] They call it the game, but it's not. You can want success all you want but to get it you can't falter. You can't slip. You can't sleep— one eye open for real and forever. [1:51:49] The thought that this cannot be life is one that all of us have felt at some point or another. When a bad decision and bad luck and bad situations feel like too much to bear those times. When we think this, this cannot be my story, but facing up to that kind of feeling can be a powerful motivation to change. [1:54:18] Technology is making it easier to connect to other people, but maybe harder to keep connected to yourself. ---- Get access to the World’s Most Valuable Notebook for Founders at Founders Notes.com ---- “I have listened to every episode released and look forward to every episode that comes out. The only criticism I would have is that after each podcast I usually want to buy the book because I am interested so my poor wallet suffers. ” — Gareth Be like Gareth. Buy a book: All the books featured on Founders Podcast ---- Founders Notes gives you the ability to tap into the collective knowledge of history's greatest entrepreneurs on demand. Use it to supplement the decisions you make in your work. Get access to Founders Notes here. ---- “I have listened to every episode released and look forward to every episode that comes out. The only criticism I would have is that after each podcast I usually want to buy the book because I am interested so my poor wallet suffers. ” — Gareth Be like Gareth. Buy a book: All the books featured on Founders Podcast

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

• 0:00David Senra?

  It was the 70s, and heroin was still heavy in the hood. Unpredictability was one of the things that we counted on. Like the day when I wandered up to something I'd never seen before. A cipher. But I wouldn't have called it that. No one would have back then. I shouldered my way through the crowd towards the middle. It felt like gravity pulling me into that swirl of kids. No bullshit. Like a planet being pulled into orbit by a star. His name was Slate, and he was a kid I used to see around the neighborhood. An older kid who had barely made an impression on me. In that circle, though, he was transformed. Like the church ladies touched by the spirit. And everyone was mesmerized.

• 0:42David Senra?

  He was rhyming, throwing out couplet after couplet like he was in a trance. For a crazy long time. Thirty minutes, straight off the top of his head. Never losing the beat. Riding the handclaps. He rhymed about nothing. The sidewalk, the benches. Or he'd go in on the kids who were standing around listening to him. And then he'd go in on how clean he was. How nice he was with the ball. How all the girls loved him. Then he'd start rhyming about the rhymes themselves. How good they were. How much better they were than yours. And how he was the best that ever did it. All he had were his eyes, taking in everything and the words inside him. I was dazzled. "That's some cool shit," was the first thing I thought. Then, I could do that.

• 1:25David Senra?

  That night, I started writing rhymes in my notebook. From the beginning, it was easy. A constant flow. For days, I filled page after page. Then I'd bang out a beat on the table, my bedroom window, whatever had a flat surface, and practice from the time I woke in the morning until I went to sleep. I saw it as an opening. A way to recreate myself and reimagine my world. After I recorded a rhyme, it gave me an unbelievable rush to play it back, to hear that voice. Everywhere I went, I'd write. If I was crossing a street with my friends and a rhyme came to me, I'd break out my binder, spread it on a mailbox or a lamppost, and write the rhyme before I crossed the street.

• 2:10David Senra?

  Even back then, I thought I was the best. I'd spend my free time reading the dictionary, building my vocabulary. I could be ruthless, calm as fuck on the outside, but flooded with adrenaline. I wasn't even in high school yet, and I discovered my voice. That is an excerpt from the book that I'm going to talk to you about today, which is Jay-Z's memoir, and it's called Decoded. Before I jump back into the book, just real quick, I get messages every week for people asking how they can buy gift subscriptions to Founders for other people. There's always a link in the show notes on the Misfit feed. You'll see, "Buy a gift subscription." And if you don't see it there, you can always go to founderspodcast.com, and you'll see it in the header. And you can buy a gift subscription for like, a few months, a year, and now there's a lifetime gift subscription option as well. Okay, so this podcast is going to be similar

• 2:55David Senra?

  to when I read, I'll be back on Founders, number 219. I read the biography of Anthony Bourdain. And the reason this is similar is because before I read the biography of Anthony Bourdain, I had read his books. I watched almost every single episode of his shows. I was a massive, massive fan. He had a huge influence on my life. And it's the same way with Jay-Z. I've been listening to his music repeatedly for over two decades. I'd watch interviews with him. I'd take notes on what he says. I have a folder on Instagram that is labeled "motivation." And so when I come across something that just hypes me up, or just a good idea, I put it in there, and then I just go to that folder whenever I have a few minutes and just watch videos. And a lot of them, it's also Jay-Z just dropping pieces of advice or lessons that he learned through his life.

• 3:39David Senra?

  And I cannot believe it's taken me this long. I have no excuse that cannot believe it's taken me this long to read this book. I remember going to a friend's house back in like, 2010, 2011, and it was on his coffee table. And I remember picking it up and leafing through, and like, wow, this is amazing. I should read this. And so it's taken me more than a decade to circle back around, but I'm very, very glad. And once I got, read it, I just could not believe how good it was. So I want to go back to the part of the introduction. It's in the very first chapter, and I just want to pull out a couple of thoughts I had as I went through some of these highlights I just read to you. When he's seeing this kid in a cipher, which is just in the early days of hip hop, it's just one person sitting in the middle rapping. Sometimes it's one person, sometimes it's a few, and they're battling, whatever the case is, and just people surrounded by them. This is the first time Jay-Z is seeing that happen. He's watching it for a while. But it was interesting what came to his mind.

• 4:23David Senra?

  He's like, "That's really cool, and I could do that." And that's an illustration of a major point that pops up over and over again in these biographies of history's case entrepreneurs, is that belief comes before ability. He had never rapped a day in his life, but he already said, "Okay, no, I believe I can do this. If that person figured out how to do it, I can too." And if I had to distill everything that I've learned about the history of entrepreneurship from reading almost 250 biographies to as little words as possible, I would say the entrepreneurs, the great founders of history, they would combine Kanye West's levels of self-belief with the work ethic of Kobe Bryant. And so that leads me to the second thing that he says on this page that is really, really interesting, and it's about the importance of practice.

• 5:06David Senra?

  And when I read that 600-page biography of Michael Jordan, all the way back on Founders number 212, it blew my mind how much Michael, in that book, talked over and over and over again about his belief in practice, his dedication to practice, that he'd rather miss a game than miss practice. And Jay-Z said the exact same thing. He says, "I would practice from the time I woke up in the morning until I went to sleep." He is not even in high school. He is a teenager. This is 12 years before he creates his first album. He's 26 years old when he releases his first album, Reasonable Doubt. This is another example of that maxim that I've said on a few podcasts, that the public praises people for what they practice in private.

• 5:49David Senra?

  The public praises people for what they practice in private. We didn't see... We saw his first album when he dropped it, and when he's 26 years old, we didn't see the 12 years before that of him practicing his craft before it was in public view. Recently, Netflix has this documentary. It's a fantastic documentary on Kanye West. It's called Genius. It's a three-part series. You can skip the third part, but the first two is all about the struggle, the founder mentality that Kanye had to possess to break into the music industry and to actually achieve his lifelong dream. And so, just like we didn't see Jay-Z practicing for 12, 13, 14 years before he's actually in the music industry... Kanye says the same thing in that documentary.

• 6:30David Senra?

  When Kanye leaves Chicago to go chase his dream in New York, it's year 2001. Kanye is 24 years old and he's selling beats, although people at the time don't realize that he's only making and selling beats so he can rap on them, right? But that was his in. He found his in to the industry. But he had been producing beats since the seventh grade. So same thing. He was 12 years old when he starts making beats. We don't see him. He doesn't start becoming famous or well-known for another 12 years. It's an incredible, incredible documentary. I've watched the first episode four times. I'll probably watch it 50, 100 times in my life. Second episode's really good as well, and I've watched it multiple times. But Kanye, on his debut album, talks about what he had to do, again, out of view of the public, right? The public praises people for what they practice in private.

• 7:14David Senra?

  And so on Kanye's album, I'm just going to read you some of his lyrics real quick from his album Spaceship. And he says, "You all don't know my struggle. You can't match my hustle. You can't catch my hustle. You can't fathom my love, dude." And this is the punchline here. "Lock yourself in a room doing five beats a day for three summers. That's a different world. Like, three summers, I deserve to do these numbers." And the reason this is important, the reason I'm bringing this to your attention, is because this is all over the history of entrepreneurship. All the experiences, the practice you put in, the things that you're learning, you don't even have an idea how you're going to be able to utilize them in the future. And we just saw this recently when I reread Sam Walton's fantastic autobiography, Made in America, on Founder's Number 234.

• 7:55David Senra?

  I'm going to read, this is so fantastic, because he puts words to this idea that I'm trying to explain to you. And he says, "Somehow, over the years, folks have gotten the impression that Walmart was something that I dreamed up out of the blue as a middle-aged man, and that it was just this great idea that turned into an overnight success. It's true that it was 44 when we opened our first Walmart, but the store was totally an outgrowth of everything that we've been doing since Newport." So he's talking about the 12 or 14 years of his retail career, all the little tiny stores that he had opened before he had learned that there was a massive opportunity that he winds up calling Walmart. So it says, "It's true that it was 44 when we opened our first Walmart, but the store was totally an outgrowth of everything that we've been doing since Newport."

• 8:40David Senra?

  I'm going to pause there, go back to what Jay-Z says. Yeah, I would practice from the time I woke up in the morning until I went to sleep. Everywhere I went, I would write. If I was crossing the street with my friends and a rhyme came to me, I'd break out my binder and I'd spread it on a mailbox or a lamppost and I'd write the rhyme before I crossed the street. It is the exact same idea, applied to two different domains. Sam Walton applied this idea to retail. Jay-Z applied it to being a rapper, to being, well, he considers himself an artist, a musician, going back to Sam. But that story was totally an outgrowth of everything we were doing since Newport. Another case of me being unable to leave well enough alone. Another experiment. And like most overnight, and like most other overnight successes, it was 20 years in the

• 9:25David Senra?

  making. And so, let's go back to Jay-Z's motivations, what I just read to you. I saw it as an opening, a way to recreate myself and reimagine my world. That is the exact same feeling. The feeling he's having is a 13 or 14-year-old saying, hey, maybe hip-hop was a way. I live in, you know, I'm not very happy with my surroundings. I live in the projects. My dad left. I'm being raised by a single mother. We don't have a lot of money. A few weeks ago, or a few months ago, I read Steven Spielberg's fantastic biography. This is back on Founders 209, in case you haven't listened to that podcast. I would highly, highly recommend. Filmmakers, I'm working on another podcast for you, on a biography of a filmmaker. Filmmakers are some of my favorite people to read about, because I think the way they approach their craft, there are just so many parallels and ideas that we can steal as founders for our own work.

• 10:10David Senra?

  But there's a line, talks about why Steven Spielberg was, he was obsessed. By the time he was like 12 years old, he's like, yep, I'm going to be the director. He starts practicing. Steven Spielberg, at 12 years old, started practicing. He said he would envision himself going to the Academy Awards and accepting an Oscar and thanking the Academy. He was 12 when he said that. Interesting enough, in that Kanye documentary I was just talking about, Kanye says something. He says, "Before I had a car, I would be walking to the train, practicing my Grammy speech." He was completely broke, couldn't even afford a car. "I'm walking to the subway to go from my apartment in Jersey to Manhattan to try to sell some beats, and I'm already practicing my Grammy speech." It's the same idea. But what I wanted to pull, what I wanted to compare for you, what Jay-Z just said,

• 10:55David Senra?

  he's like, "I thought it was a way for, an opening for me to recreate myself and reimagine my world." It's very similar to what Steven Spielberg said in his, they said about him in his biography when he was a young person. He was disappointed in the world. So he built his own. Jay-Z used hip hop and rapping to build his own world. Steven Spielberg used making movies, directing movies, to make his own world. And then just one other thing before I move forward in the book. Again, the importance of practice. That is the main lesson from, and Jordan, and Michael Jordan, you know, it says in the book that maybe no one has ever been as good at their job as Michael Jordan was at his like later in his career. So there's a lot, like, obviously, we're all trying to get to the top of our professions. We're trying to be the best we possibly can be. That's why we're listening to this. That's why we're reading these books.

• 11:40David Senra?

  That's why we're doing all the stuff we're doing. And so Jordan just has a lot of things to teach us, but the importance of practice. And so ever since I read, I'll tell you what I, like, how I interpret that for my own work. And so since, ever, ever since I read that, or Jordan taught me that, I spend hours, hours, every day, when I'm not reading books, or when I'm not making podcasts, I'm rereading the highlights. I told you, I have over 20,000 highlights in this app called Readwise. So every single highlight I make goes into this app called Readwise. It becomes this gigantic search, like, database of all my notes and highlights from the history of entrepreneurship, and I just read them over and over again. And so what do we see here? Jay-Z, what is he saying? He's a young kid, and he, he's like, all I have are my eyes and my words, right?

• 12:23David Senra?

  So he says, I'll spend, I'd spend my free time reading the dictionary, building my vocabulary. It's the same idea. Remember that, too, because there's a fantastic story where Jay-Z gets to have dinner with Michael Jordan later in the book, so I'll bring that up to you, because it's just fantastic. It's two of my favorite people having dinner together. So then he's talking about this time. This is the late 70s, early 80s. And if you ever study Marc Andreessen, so back on Founders Number 50, I read Marc Andreessen's, I think it's like 200-page archive of his blog that used to be on, you can go back there in, in Founders Number 50, you'll see the link to download the PDF for his blog. It's fantastic. It's absolutely free. There's no reason not to read it. It's, it's really amazing. But Mark's advice for young people, he's like, listen, you should only be working

• 13:07David Senra?

  in the industries where the founders of the industry are still in charge of their companies. I thought that was a really interesting idea. I never even thought about that before. And so what Jay-Z's picking up here, he's like, well, I'm in a brand new industry. They don't even really know like what, they don't even know, like, some people are making a tiny bit of money where the case is, he's like, but I have a gigantic opportunity. So not only can I practice my craft and get better over time, but I'm in this, I'm in an expanding market. And so it will lift me along with that. And he says, I'm not going to say that I thought I could get rich from rap, but I could clearly see that it was going to get bigger before it went away, way bigger. And then we're going to get into something that also blew my mind, and it's silly that it should blow my mind at this point, right?

• 13:51David Senra?

  Given everything you and I have talked about. But how much of this book is Jay-Z talking about studying the great people that came before him, breaking down their approach to their craft? So the book has chapters, but in between each chapter is Jay-Z's, he's like, handpicks some songs. And so he'll go through line by line, and he'll give you his interpretation. He's like, people listen to my songs, they don't even understand what they're about. And so the way he did that for his own music, he's been doing that forever for the music of other people. It's very similar to how you and I are approaching these books, where like, it's not just a line. We look at it, we underline it, we try to tie it to other things, we really think deeply about what the hell it means. And so in this case, this is the first example, he's talking about, hey, I really looked up to people like Run DMC, The Sugar Hill Game, Kool Moe Dee.

• 14:34David Senra?

  And so he's going to talk about what he liked about Run DMC's songs. And he says, their rhymes were crisp and aggressive. And he's talking about Run, Run DMC. He says, Run rapped about having a big, long caddy, not like a Seville. And so he's quoting him. And then this is the important part. He says, that line seems like a throwaway, but to me, it felt meaningful. And the note I left myself on that page is like, I feel the same way. Like, I'll be reading an entire paragraph, a page, and there's just something that jumps out at you. And you can't even really describe why it's so important. But they're not random lines. They have, if you sit down and pause, and they'll just skip to the next paragraph and think about what's happening, it's like a prompt for your thinking. And then here, Jay-Z describes his early life when he's starting to do this.

• 15:15David Senra?

  And the crazy thing is, so he says, I was just a kid from public housing, whose whole hood would rubberneck when an expensive car drove down the block. And what I wrote, and I wrote this several times throughout the book, when he says stuff like this, it's like a lot can happen in one lifetime. He goes from a kid living in public housing who is lusting after an expensive car to living in a $100 million house in Bel Air. That happened. That actually happened. That is possible. And the great thing about reading autobiographies is the fact that the stuff is not sugarcoated. They talk in a way that they may not talk in like, public interviews, or if they're marketing a new project, or whatever the case is. So in this case, he's describing the environment that he grew up in. And this is the environment he had to survive. And he talks about the

• 15:59David Senra?

  fact that he was a kid when the crack epidemic in the 1980s just exploded. And he says, "But when crack landed in your hood, it was a total takeover, sudden and complete. Most of these crack fiends were my parents' age or a little younger. They were skeletal and ashy, and they were as jittery as rookie beat cops, and their eyes were always spinning with schemes to get money for their next hit. Kids my age were serving them," meaning they were the ones, the kids were actually the ones selling the drugs to the older crackheads. "Guys my age," and why were they doing that? "Because guys my age, fed up with watching their moms struggle on a single income, were paying utility bills with money from hustling." So that hustling is obviously, he's talking about selling drugs. He says, "The courtyards

• 16:41David Senra?

  of my projects, of Marcy projects and projects across the country, contained teenagers who wore automatic weapons like they were sneakers. We had grandmothers who were afraid to leave their house." And he doesn't sugarcoat things for us. He's selling drugs at a very young age, and this is what's the person he used to buy. What happened to the person he was buying drugs from, so like, his supplier, like, his wholesalers, you can think of like that, his name was DeeDee. "When DeeDee was murdered, it was something out of a mob movie. They cut off his balls and stuffed them in his mouth and shot him in the back of the head, execution style." And so that is a crazy, crazy environment that he's got to develop the skills to not only survive, but escape and then thrive throughout life. So the main theme of the

• 17:23David Senra?

  book, because he spends a lot of time talking about, let's say, his teenage years to his like early twenties. He's selling drugs. He doesn't want to sell drugs, but he's not sure. He's like, if rap was actually a career. And he talks about the fact that people that were from similar projects like him, Biggie Smalls and Torres B.I.G. grew up in a project in Brooklyn. Nas grew up in a project in Queens. And he says, once he saw them blow up with their initial, with their albums. So Nas did Elmatic when he was like 17 years old, which is crazy. Like, it's just insane how somebody that young could build something, could make a classic album at such a young age. And then Biggie's Ready to Die, both came out before Jay-Z, and that really helped him realize, hey, this is actually possible.

• 18:08David Senra?

  And so that struggle of like straddling two worlds, like, you know, there's stories in the book where he's been selling drugs in Virginia for three days, and he's got to go and meet a record executive to try to get a label. So he's got to drive back from Virginia overnight, shows up all dirty, you know, smelling terribly, terribly, trying to convince this guy to sign him. And I guess I kind of just, I just turned the page and I kind of just ran over my own point that I was trying to make, and he says it better than I could. "I was still rhyming, but now it took a backseat to hustling. It was all moving so fast, it was hard to make sense of it or see the big picture. Kids like me..." Think about that, kids. He's a kid. "Kids like me..." And you don't feel that way. I remember being 16 or 17. You damn sure don't feel like a kid, but you definitely are. You just don't know it. "Kids like me were going through something strange and

• 18:53David Senra?

  twisted, and we had a crazy story to tell." So through a friend of a friend, he winds up meeting one of his idols, which is this rapper called Big Daddy Kane. And at this point, remember, when I'm about to read to you, Jay-Z has no intention. He's like, I'm not, he's, I guess I'll just be a hustler. You know, that's what I'm going to do for my life. So he winds up meeting Kane. He's still rhyming, so Kane puts him on an album, one of his songs. And that song is actually played on the radio. And he's like, this is crazy to me. And he says, people were talking about the second kid on the tape. That's him. The emcee before Kane. I was getting great feedback. I couldn't believe people even noticed my verse. And he says he couldn't believe they could notice his verse because Big Daddy Kane was so, he had a, like, an audience. He had people that liked him.

• 19:38David Senra?

  And people thought he was really, really good. And so Jay-Z gets on a track. He's like, wait a minute, I can hold my own with one of the best. And so then he goes back. And again, this just blows my mind. Jay-Z is studying the greats that came before him, which is exactly what you and I do every week on this podcast. There was no one like Rakim. His flow was complex and his voice was ill. He was approaching rap like literature, like art, which is exactly what Jay-Z considers it. He's like, I write, but I don't write things down. So I don't know if you know this, but Jay-Z is famous because he starts writing things in his notebook when he's younger. But as he gets older, and you can actually see this in, there's a documentary, it's called Fade to Black, came out like 15 years ago. I rewatched it for prep for this podcast. And it's when Jay-Z thought he was going to retire.

• 20:23David Senra?

  And it shows him building the album. And so he goes to California and he's working with this famous producer named Rick Rubin, who's one of the co-founders of Def Jam. And he's produced albums for everybody, not just hip hop artists, but country people, rock, everybody goes all over. They think Rick is just an amazing person. Actually, I have a note for you real quick. I wasn't planning on talking about it right now, but while I'm, in case I forget to talk about Rick Rubin later on, he's, Rick Rubin like hangs out with people like Jack Dorsey, like seeks his counsel and stuff like that. But in the documentary, it's funny, he says, this is what Jay-Z likes about Rick Rubin. He goes, listen, Rick ain't normal. I don't give a fuck. He is strange by strange standards. And he goes, when's the last time you seen a bison in some dude's studio? And he's making music with, in a room with Rick Rubin.

• 21:07David Senra?

  And Rick Rubin's got this huge stuffed bison. And so this is what Jay-Z loves about him. He goes, listen, Rick is 20, over 20 years into his career, and now almost 40 years. Over 20, and he's still doing it, that's amazing. Over 20 years into, this is Jay-Z talking, over 20 years into his career and the dude ain't changed. He's got his own vibe. You gotta love him for that. And so, our interpretation of that is, he didn't build, his product in some degree is himself. And he knows what Peter Thiel taught us. It's like, you don't build an undifferentiated commoditized product. You have to differentiate, you have to build something, and it's even better, like James Dyson taught us on his autobiography. Build something that looks strange. At least it gets people talking about it. Don't just go out and copy what everybody else is doing. Like, make it look weird.

• 21:50David Senra?

  Rick Rubin, your experience in dealing, and letting him produce your music, it's gonna be an odd experience. An experience that you can't get nowhere else. And so, in that documentary, Rick is telling something else. He's like, Jay-Z's very unique because he does everything in his head. He doesn't write it down. He waits to hear the track, and then he's got an idea, and you'll see him like, he calls it his Rain Man. He's like mumbling, like, you can't really tell what he's saying, but his lips are moving. And so, the reason I bring that up is because Jay-Z talks about, he's like, I think of, I'm like a poet. That's the way I look at what I'm doing, and that's why I have to explain it to you, because a lot of people are listening to my music and they're not even understanding what I'm trying to say. And so, this idea where he's like, wait a minute, like, Rakim is the first person I actually saw approach rap like literature, like art. That's what I wanna do.

• 22:35David Senra?

  And then he says, and his songs still banged at parties. Then he starts talking about what he learned from Ice-T, KRS-One, Dr. Dre, all these other people, over and over again. And so, the way I think about what's happening right there in the book is like, Jay-Z is doing exactly what Steve Jobs did, Bill Gates, Jeff Bezos, Warren Buffett, Charlie Munger, they all did this. They're analyzing the people that came before them, seeing how they approached their work, seeing what ideas that took them many, many decades to learn, and then taking the ideas and adding, he's taking their ideas and adding his own unique twist on them, and using them for his work. And I think the reason I like, I'm talking fast and like, getting kind of excited is because like, this is just a reaffirmation for me and for you, is like, we are on the right path. We are doing exactly what we should be doing. Just keep doing it.

• 23:20David Senra?

  And so, another theme in the book that Jay-Z talks about, he's like, I just love language. And so, this is him talking about his love of metaphors. I love metaphors, and for me hustling is the ultimate metaphor for the basic human struggle. The struggle to survive and resist, the struggle to win, and the struggle to make sense of it all. And something that may surprise you, but I kind of like, listening to his music and hear him talk in interviews, you kind of get this. He's rather introverted, and he says the promotion, he's talking about the, what happens after you create the album. He says, "The promotion was already starting, which isn't my favorite part of the process. I'm still a guarded person when I'm not in the booth, or onstage, or with my oldest friends. And I'm particularly wary of the media." And so he talks about, he's like, "Listen,

• 24:04David Senra?

  man, if I don't know you, I'm gonna be real quiet. But once I get to know you, I won't shut the hell up." And like, I'm the exact same way. And that's another thing I appreciate that Jay-Z talks about not only in his music, but in the book a lot. He's like, "Humans are multifaceted, man. We do things that we can't really explain. There's gonna be actions that we're really proud of, actions that we don't like about ourselves, and you have to take the person as a whole. But there's just simply no such thing as a perfect human." Okay, so now we get to the first example of when he's breaking down his own lyrics. This is from the song "American Dreaming," and it's really a story about entrepreneurship. I've mentioned Jay-Z a bunch of times on previous podcasts, because I think, especially like his album 444, a lot of them, it's like entrepreneurial anthems. And so I'm

• 24:45David Senra?

  gonna go through this and try to make sense. I have, the connections I make here are so bizarre. Okay, so it starts, first, I'm gonna give you his, the line he says, and then his interpretation of this. So it says, "This is the shit you dream about, with the homies steaming out. Back, back, backing them beamers out." So his interpretation of that line, this is Jay-Z talking. "This is really where it begins. In a room with your dudes, too young to shave, dreaming about big body Benzes you're gonna push. Obviously, for me, this is happening in Marcy, but this could be anywhere. A basement in the Midwest, a backyard in California, an Oldsmobile somewhere down south. The danger is that it's all just talk."

• 25:26David Senra?

  And then this is, I double on the line, this section, "I believe you can speak things into existence." So another thing that surprised me, and it shouldn't surprise me by now, Jay-Z talks over and over, he probably mentions it at least three or four times in the book, on the power, and he talks about in the documentary, "The power of visualization, of seeing things in your mind before you see them in person." This is something that we learned Estee Lauder did. Bob Noyce, the founder of Intel, did. Edwin Land, the founder of Polaroid, did. Steve Jobs did. Arnold Schwarzenegger. They all did this. Now, Jay-Z, I believe you can speak things into existence. And he says, "It starts from a dream. You're sitting there daydreaming with your friends about future success." And so then he says, "Seems as our plan to get a grant, then go off to college, didn't pan or even out."

• 26:09David Senra?

  He's like, "No one goes to college from where I'm at in the hoods." So he's like, "All right, so that's not going to work. What are we going to do? We need it now. We need a town. We need a place to pitch. We need a mound." And so that's the first time he's going to mention. "You need a product to sell and you need a market to target." That's exactly what he's telling us here. This is what I mean. They're just entrepreneurial anthems disguised as rap songs. He says, "Mama forgive..." I'm not going through every single... I'm not going to read... These are just the highlights I had, like the things I underlined in the song lyrics. And then so he says, "Mama forgive me. I should be thinking about Harvard, but that's too far away. We're starving." And so even though everybody didn't grow up in the projects like Jay-Z, there's a lot of people that understand exactly what he's saying there.

• 26:53David Senra?

  He's like, "I should be thinking about Harvard, but that's too far away. We're starving." I remember when I was about to graduate high school. He was like, "Hey, where are you going to go to college? What do you mean, where am I going to go to college? Whichever one I can drive to, whichever one I can work full-time while I'm doing this. My parents didn't even graduate high school. So this idea where I should be aiming at Harvard, that's ridiculous." And then he goes on to the next thing. Ain't no... This is going to remind me about... Okay, so he says, "Let me tell it to you first. Ain't nothing wrong with the aim, just got to change the target." So to me, he's saying you have to pick... Picking the right market is essential. This is something Warren Buffett warns over and over again in his shareholder letters. This is something Marc Andreessen talks about over and over again in his blog archive, that picking the right market is essential. In fact, if you would ask Marc Andreessen, he's like, "What is a more predictor for business success?

• 27:37David Senra?

  Is it the market, the team, or the product?" And then he... Marc's a great writer, too. And he gives the answers that you're most likely to expect. It's the team, it's the product. And he's like, well, actually, I'll take the market. And so what's crazy is all that stuff. Jay-Z just described all the ideas behind these lines. This is where I'm extremely envious of him is like his efficiency with communication. Like, he can just use, he can tell entire stories. And a lot of great musicians do this as well, in just a few lines. So we're not even, what is that, three, four lines? We're not even, we haven't even touched the surface of the song. So he says, ain't nothing wrong with the aim, just gotta change the target. I just gotta figure out where I'm gonna direct my talents. And so then he says, and it's not like, they're just young kids. They have to figure it out as they go. And it's not like we're professionals moving the decimals.

• 28:22David Senra?

  Do you know where to cop? Nah. Gotta connect? No. So what he's saying there is, that's obviously for drugs, but for our purposes, it's, do you have something to sell? Do you have a way to get something to sell? You can sell somebody else's product, or you're gonna make your own? So he's like, do you know where to cop? Do you know where to buy drugs? No. Do you gotta connect the person selling drugs? No. And then he summarizes the very beginning of an entrepreneurial journey. Who in the F knows how to be successful? They say it's celestial, it's all in the stars. And then he says, and at all costs, you better avoid these bars. So in his game, it's like, listen, you better not, you need to avoid going to jail. It's the way you go bust. You can't be successful if you don't first survive. So that's their example of that. You know what I wrote down when I got to the line?

• 29:07David Senra?

  He says, at all costs, you avoid these bars. It's something, I love the founder of Sequoia Capital, Don Valentine. And I don't think I even knew about him when he was alive. Maybe I did, but he passed away recently. And if you go back and like, watch videos of his on YouTube, they're just absolutely fantastic, because this guy's got no fluff. And what I wrote down when I got to this part, he says, at all costs, you better avoid these bars. Don Valentine says, all companies go out of business, all companies that go out of business do so for the same reason. They run out of money. And so Don would advise his entrepreneurs, like, you need to focus on cash flow. Another thing, I love Don, he just cuts through all the bullshit. Don says, two things in business matter, and you can learn this in two minutes. High gross margins and cash flow. The other financial metrics you can forget.

• 29:50David Senra?

  So back to Jay-Z, says, at all costs, you better avoid these bars. This is a crash course, this ain't high school. So it's obviously very dangerous. In his case, you could die or go to jail. In our case, we could go bankrupt. If we're not, like, we could run out of money, we can cause a lot of pain, not only to ourselves or everybody else around us. This is a crash course, this ain't high school. If we make mistakes, we have very, very real consequences. And then this is one of my favorite parts of the song that I've repeated over and over again in my own life. You're now in a game where only time can tell. Survive the droughts, I wish you well. Survive the droughts, I wish you well. How sick am I? I wish you health. I wish you wheels. I wish you wealth. I wish you insight, so you can see for yourself. I double underline that last part. I wish you insight, so you can see for yourself.

• 30:34David Senra?

  And that is him telling us you have to do the work necessary to trust your own judgment. Companies live and die by the founder. No one is coming to save you. I wish you health. I wish you wheels. I wish you wealth. I wish you insight, so you can see for yourself. Now, let's go back to when Jay-Z was 19 and his informal mentorship, right? With Big Daddy Kane. And so he says, it was 1988. I was still in the streets and I basically accepted that I'd be a hustler who happened to rap in his spare time. I thought the rap game was crooked and a little fake. Big Daddy Kane was playing a role. Hip-hop's first playboy. He had silk robes and pretty girls in all his videos and all that. But his flow was sick. So his point was, it's like, yeah, people see The Flash, right?

• 31:17David Senra?

  They see the girls, they see the robes, they see the jewelry. But I'm actually looking at what he's actually saying and how he does it. And I'll tell you what this made me think of in a minute. He was condensing, stacking rhymes on top of one another. Trying to keep up with him was an exercise in breath control, in wordplay, in speed, and imagination. He was relentless on the mic. So think about that. How many people watching Big Daddy Kane's music videos, how many people who are listening to his music are thinking about stacking rhymes on one top of another? How many of them are thinking about the importance of your breath control? The importance of your wordplay? The speed at which you're saying the words and how you space them out? And so he says, I went on the road with Kane for a while. And I double underline this section.

• 31:58David Senra?

  I got an invaluable education watching him perform. This is the exact same, the way Jay-Z is talking about Big Daddy Kane is exactly, exactly the way Kobe Bryant used to speak about Michael Jordan. And so Kobe said, when I grew up watching Michael play, my gener- Listen, this is, I have goosebumps right now. This is freaking crazy. When I grew up watching Michael, or excuse me, when I grew up watching Michael play, my generation saw the highlights and the fancy stuff. But what I saw was his footwork. I saw the spacing. I saw the timing. I saw the fundamentals of the game. Is that not exactly what Jay-Z was just telling us? I got an invaluable education from watching him perform.

• 32:41David Senra?

  I was watching his breath control, his wordplay, the way he stacked rhymes on one another. While you're watching the girls and the jewelry and the robes, just like Kobe's generation was watching the highlights and the fancy stuff. Kobe's focused on the footwork, the spacing, the timing, the fundamentals of the game. Back to Jay-Z. Kane had just an incredible amount of showmanship. Even today, I use some of the ideas I picked up back then in my own shows. Let's go back to what Kobe just said, or I haven't said it yet, but what Kobe said. Everything that I do, I learn from the guys who came before me. Go back to Jay-Z, before we go back to Kobe. I use some of the ideas I picked up back then in my own show. And he was generous, too. Generous, remember that word.

• 33:25David Senra?

  He'd stop the show and bring me out when no one knew who the hell I was. If you watched the fantastic documentary, The Last Dance, Episode 5, right before Kobe passed away, unfortunately, he was interviewed, and this is what Kobe said. "When I came into the league, Michael provided a lot of guidance for me." I don't know why I'm getting a little emotional. "I had a question about shooting his turnaround shot. He gave me great, detailed answers. And on top of that, he said if you ever need anything, he gave me a call." Guess what? Bob Noyce of Intel and Bill Hewlett and David Packard of HP were generation older than Steve Jobs, and they did the same thing. It's the right thing to do. And then Kobe says, "I truly hate having discussions." What is going on?

• 34:10David Senra?

  My voice is cracking. All right, okay. I get excited about this stuff, man. "I truly hate having discussions about who would win one-on-one, our fans saying that you'd beat Michael. I feel like, yo," and he puts his hands up, Kobe puts his hand up to say, "stop, to chill." And he says, "So I hate having these discussions about who would win a one-on-one, our fans saying that you'd beat Michael. I feel like, yo, what you get from me is from him. I don't get five championships without him, because he guided me so much and gave me so much great advice."

• 34:46David Senra?

  That is so powerful. It made me think of when I reread Steve Jobs biography by Isaacson. I just did, I recorded another podcast on it. It's episode 214, if you haven't gone back and listened to it. But there's something that Steve says as he's dying, because he's working with Isaacson, as he's dying, there's two things. But I want to read this to you. And he talks about like, you know, what did Nicoby could say, "Yeah, yeah, you know, oh, I'd give it to him one-on-one," and all this other stuff. He's just like, "I wouldn't have had five championships without them. Everybody builds on the work from the great people that came before them." And so Steve is telling us, like, he's parting words of advice to us. He's like, "Listen, I hate it when people call themselves entrepreneurs, when what they're really trying to do is launch a startup and then sell or go public so they can cash in and move on. They're unwilling to do what it takes to build a

• 35:27David Senra?

  real company, which is the hardest work in the business. That is how you really make a contribution and add to the legacy of those who went before. You build a company that will still stand for something a generation or two from now. That's what Walt Disney did, and Hewlett-Packard, and the people who built Intel. They created a company to last, not just to make money. And that is what I want Apple to be." And then the other example happens when Jobs is in a massive lawsuit with Google. And so he says, "Jobs had another visit that month from someone who wanted to repair fences. It was Google's co-founder Larry Page, who lived less than three blocks away and had just announced plans to retake the reins of his company. He asked if he could come

• 36:11David Senra?

  by and get tips on how to be a good CEO." This is really important because they're in a massive lawsuit against each other. And look at what Jobs does. He does the right thing. So it says, "Jobs was still furious at Google. 'My first thought was, "Fuck you," Steve said. But then I thought about it, and I realized that everyone helped me when I was young. What is happening in the book where we're at? Big Daddy Kane is a star. No one knows who the hell Jay-Z is. He does not have to give him the time of day. Not only does he put him on songs, not only does he let him go on tour with him, he brings him out and tries to introduce him to other people when no one knew who he was. But then I thought about it and realized that everybody helped me when I was young, from Bill Hewlett,

• 36:54David Senra?

  founder of HP, to the guy down the block. So I called him back and said, "Sure." Larry came over, sat in Jobs' living room, and listened to his ideas on building great products and durable companies.

• 37:08David Senra?

  So then he talks about mentoring Memphis Bleak, which is like this young kid that lived in his projects as well. They do a song together, and I just want to pull out one line here because just one line made me think of so many other examples. And so Jay-Z, in the song, he's playing the role of like the older mentor to the younger person. And he says, "Hold up, now, listen to me. You let them other dudes get the name, skip the fame. Ten thousand or a hundred, so ten thou or a hundred gees, so ten thousand or a hundred thousand dollars. Keep your shit the same." And so that's the line, and then this is Jay-Z now writing, many years after the fact, what it means. And he says, "This is a classic piece of OG advice." So, original gangster, like, the interpretation of that would be like somebody older and wiser than you. Okay, so their slang is OG. "This is a classic piece of OG advice.

• 37:53David Senra?

  It's amazing how few people actually stick to it." So, the advice from Jay-Z is, "Stay on your grind." That's the way he says it. If you go back to Founder's number 56, when I did the biography, the book on Herb Keller, the founder of Southwest Airlines, the only airline that was profitable for forty-something straight years. It's amazing. Herb's got a fantastic personality, one of the best personalities of anybody I've come across. But he says, and he's essentially saying the same thing, that the same advice that Jay-Z's giving to Memphis Bleak here, and giving to us, Herb gives it to us as well. He says, "Success has to be earned over and over again, or it disappears." And so Jay-Z's saying, "Doesn't matter if you have a little bit of money or a lot of money, you still act the same, you still do the same thing."

• 38:37David Senra?

  Jay-Z quotes later on, and he puts it on one of his songs, at the very beginning of one of his songs. It's Biggie Smalls talking about advice that he got from who signed him, which is Diddy. The advice that Diddy gave him when they were coming in, they were both young, you know, early twenties. And so, Biggie says, he says, "Just try to stay above water, stay busy, stay working." Puff, who was called Puff at the time, we know him as Diddy today, "Diddy told me that the key to this joint, the key to staying on top of things, is to treat everything like it's your first project. Do you know what I'm saying? Like it's your first day back when you were an intern. That's how you try to treat things. You have to stay hungry."

• 39:20David Senra?

  And so they're picking up on this natural tendency of human nature that you're really hungry when you're coming up, you're dedicated, you stick to it, but it's really hard. Like you got rich, maybe you don't have the same motivations that pushed you when you were younger, or when you were hungrier. You lose that hunger. And then what happens as soon as you stay off your grind, as he says, 10,000 or 100 Gs, keep your shit the same. Once you get off of it, you fall off. As Herb said, you can't do that. Your success has to be earned over and over again, or it's going to disappear. Skipping ahead, he's analyzing the song called, it's "De evils, devils," with an apostrophe, but there's just one line from here, and he says, "Nine to five is how you survive.

• 40:01David Senra?

  I ain't trying to survive. I'm trying to live it to the limit and love it a lot." That's why I feel they're really entrepreneurial anthems. "Nine to five is how you survive. I ain't trying to survive. I'm trying to live it to the limit and love it a lot." Entrepreneurs are chasing what Marc Andreessen says, like you only experience two, as an entrepreneur, you only experience two feelings, euphoria and terror. We're not seeking equilibrium. If we wanted to seek equilibrium, we'd go get a job. We're not interested in that. Going back to the Jay-Z's parallel, his thoughts on lyrics and rhymes is very similar to my thinking on books. He says, "Great rap should have all kinds of unresolved layers

• 40:43David Senra?

  that you don't necessarily figure out the first time you listen to it. Instead, it plants dissonance in your head. It leaves shit rattling around your head that won't make sense till the fifth or sixth time through. It challenges you." The problem isn't in rap, or the rapper, or the culture. The problem is that so many people don't even know how to listen to the music. And here's an example of that, because this is just one line, and I'll tell you, it's very similar to what you and I just discovered on that book about the early history of PayPal back on episode 233. "Every hustler knows the value of a feint," meaning a head fake, like a movement that is not actually, that is not going to reveal your intention, okay? "Every hustler knows the value of a feint. It keeps you one step ahead of whoever's listening in."

• 41:28David Senra?

  So in that fantastic book, Founders, that Jimmy Sony wrote about the early history of PayPal, there is something that Reid Hoffman, who was working at PayPal at the time, goes on to find LinkedIn, and now he's a venture capitalist and all this other stuff. But at the time, he gives the rope a dope. He does a feint to eBay. So PayPal's getting ready. They'd been in acquisition talks with eBay over and over again. They always fell through. And so PayPal's going ahead with the IPO. And they're worried that during the quiet period where they can't say anything, that eBay could torpedo their IPO by saying, oh, yeah, most of their business is on our platform and we're getting ready to kick them off our platform and just use our own payment system.

• 42:11David Senra?

  So essentially, when they're going to attack somebody that they don't like, because eBay and PayPal did not like each other, and they're going to attack the weakness of their enemy at a time when the enemy cannot fight back. So they come up with, and that's why you have to read the book over and over again, because these guys were geniuses on how they, just this unique way they solve problems. So Reid Hoffman says, hey, you know what? Let's sit down and let's have more acquisition talks. I think we can work this out. And so he's only doing that because if you're in the middle of, if your company's trying to buy my company, and I can convince you, I'm feinting, I'm faking, that I am really interested and I want to sell you my company, let's just get this locked up now, you're not going to say things that will decrease the value of the company.

• 42:55David Senra?

  You're not going to destroy my IPO. And the entire time, Meg Whitman, who's the CEO of eBay at the time, thought that they were serious. They were never serious. They did not want to sell the company. They just wanted you not to destroy the IPO. So let's go back. Again, that's a long story. It goes over a couple of pages in a book. Jay-Z says it. Every hustler knows the value of a feint. It keeps you one step ahead of whoever's listening in. So then we go back to studying the greats. Before he could meet the greats, he had, he would study them through their music, right? And at this point in his career, and this is not, the book is not in chronological order, just so you know. At this point in his career, he's already super famous, so he gets to sit down and meet with Quincy Jones and Bono from U2.

• 43:38David Senra?

  I met Bono years ago in the cigar room of a bar in London with Quincy Jones. This book is filled with stories like this, which, again, I've been a lifelong Jay-Z fan. I didn't even know that stuff. I spent most of the night quizzing Quincy about Thriller, which I think is the greatest album that's ever been made. Bono was beaming and laughing the whole time. I liked him right away. I was completely unprepared for what a genuine, humble, and open person Bono was. We became friends after that night. So then they run into each other later on in New York. He told me he read an interview I'd done somewhere. The writer had asked me about the U2 record that was about to be released, and I said something about the kind of pressure a group like that must be under just to meet their own standard. Bono told me that my quote had really gotten to him. In fact, he said it made him a little anxious. He decided to go back to the studio, even though the album was already done, and he kept reworking it until he thought it

• 44:23David Senra?

  was as good as it could possibly be. This is the important part, and the reason I'm bringing this to your attention. Because, again, from the outside, Bono's super famous, he's YouTube, like, he's settled. He's not nervous, he's not worried. Yes, he is. Everybody is. I really wasn't trying to make him nervous with that quote, and I was surprised to find out that at that point in his career, he still got anxious about his work. It is only right that I met him and Quincy Jones on the same night. They're both already in the pantheon. We ended up trading stories about the pressure we felt, even at this point in our lives. And so Jay says, I've heard him say in interviews over and over again, hey, listen, I respect the greats. I learned from the greats, but I'm competing with them, too. I want to be the best that ever did it. There was something beautiful about Tupac being my closest competition on the charts that week. So he talks about, they both released

• 45:06David Senra?

  albums. This is many years after Tupac died, and Tupac winds up coming in second, he comes in first. So there's something beautiful about Tupac being my closest competition on the charts that week. Aside from the heartbreaking, the heartbreak of losing two great MCs and one great friend, I've always felt robbed of my chance to compete with Tupac and Biggie. Competition pushes you to become your best self. Jordan said the same thing about Larry Bird and Magic Johnson. That desire to compete and to win was the engine of everything we did. So then he flashbacks in his life. He's still thinking, okay, like, am I going to sell drugs? Like, can I make this hip-hop thing work? And I'm going to read my notes to you first before I read this section, because I think it informs what's happening

• 45:48David Senra?

  here. And I wrote, "Founder mentality." You know exactly what Jay means here. I wanted money and excitement and loved the idea of cutting myself loose from the rules and low ceilings of the straight world. She's like, I'm not going to get a job. The kid on the street is getting a shot at a dream. He sees the guy who gets rich and thinks, yep, that'll be me. He ignores the other stories going around. So for his purposes, he's talking about death and jail. Our purposes, we're thinking, yep, that person's built a successful company. So can I? We also know that there's a ton of people who fail and there's devastating consequences to that. And so he goes back to this. These kids, he sees the guy who gets rich and thinks, yep, that'll be me. He ignores the other stories going around. They're working because they think they're due for a miracle.

• 46:31David Senra?

  The kid in McDonald's gets a check and that's it. I never even considered that as a possibility. When you've got a nation of hustlers working for a small handful of slots, you learn something that you never learned at McDonald's. If you've got the heart and the brains, you can move up quickly. There's no way to quantify all of this on a spreadsheet, but it's the dream of being the exception. And he also clarified, he's like, listen, I'm not dissing you if you go to work at McDonald's. Because he says it's like, it was very, there's like a level of courage to walk through the hood, the Marcy Projects, in your uniform. And everybody else is saying, hey, go play basketball, go sell drugs, do all this other stuff. He's like, no, I'm taking a predictable path to success, where I can actually pay my bills

• 47:14David Senra?

  legitimately and not worried about getting killed or going to jail, or whatever the case is. But Jay-Z's saying, he's just like, I don't ever, I never thought about that. I've never, he says in his rap, he's like, I never had a job. Like, he never had a job in his entire life, other than one that he made for himself. So one of the people that he gets to know when he's still, before he's in the music industry, is this rapper named Jazz. And there's just, he learns something because Jazz gets signed. He's one of the first people he knows to get signed to a major record deal. And that's where he's like, wait a minute, this isn't what we see. Like, they're not actually adding a lot of value. They want to, he says it's like the most crooked legal contract in history. So he says, I would link with Jazz. We'd go back and forth to each other's houses and write rhymes for hours. We'd lock ourselves in a room with a pen and a pad. So again, he's telling us, practice, practice, practice, over and over again.

• 47:59David Senra?

  Jazz got a record deal. EMI advanced him a ridiculous amount of money, nearly half a million dollars. That was huge back then. The label rented Jazz a flat in London to work with Chuck, which is this new, I guess, successful producer. So, "Go to London, we'll rent you an apartment and work with Chuck and record your debut." Jazz invited me along for the ride. Inside, I was doing backflips and shit. So Jay-Z's talking about it, I was like, "Listen, I barely..." I'd been out of my projects, I'd been to maybe Virginia, Maryland, New Jersey, but I'd never been abroad. Like, this is insane. And even though I didn't go around talking about it, even to my closest friends, I believed I could make it as a rapper too. So he talks about the time in London. "I was like a sponge.

• 48:43David Senra?

  When I'd sit in on Jazz's recording sessions and meetings, I never gave my opinion about how his business was being run. I was new and I didn't necessarily know how things worked in the music business. I did notice that even though we were in London for more than a month, when the guys from EMI finished Jazz's album, it didn't sound that different than his demo. So, okay, wait a minute, we spent all this time and money over here, like, his album's the same, and besides, you gave him one new track." He says, "The only new track they gave him was 'Hawaiian Sophie.'" But the point is like, "Well, this doesn't seem right, so I'm noticing, I'm trusting my intuition, saying, 'Hey, something's off here.'" But the problem is, is like, they have the experience. Like, they're the record label, like, they had just made a successful album with Will Smith, maybe they know something we don't. So it says, "But we were looking at the plaques on their walls and thinking about the radio

• 49:27David Senra?

  play that got Will Smith, and we let them convince us that 'Hawaiian Sophie' was gonna make Jazz blow. Unfortunately, it didn't read that way once the video came out. That single was nearly career suicide for Jazz. He went from being courted at the highest level to not having EMI return his phone calls. The wildest shit about the whole thing was that the executives at EMI, who had withdrawn support for Jazz's project, were coming to me behind his back to holler at me on some solo shit. I thought to myself, 'This business sucks. There's no honor, no integrity. It was disgusting.'" And he talks about how devastating it is from the individual's perspective. Jazz's debut album, something that he'd been dreaming about his whole life, did come out,

• 50:10David Senra?

  but in the end, it was nothing more than a tax write-off for a giant corporation. "After the way EMI handled Jazz, I buried my little rap dreams and I took it out on the block."

• 50:23David Senra?

  He says, "All right, I'm not gonna be a rapper. I'll go back to selling drugs." And then here's the problem, a little while after, he's like, "This can't be my life. This isn't how my life should be," is a very powerful motivator. He says, "In that bitter cold, folded into the crevices of a project wall, hundreds of miles from home, I sold crack to addicts who were killing themselves, collecting the wrinkled bills they got from god knows where. I stood there thinking, 'What the fuck am I doing?'" And so eventually, he's gonna be like, "I gotta give it a go." And he realizes, forget trying to get signed by a record label, right? Even though no one would sign him, which is hilarious, because he sold, what, 125 million records up until this point? No one wanted to sign him, so he had to make his own record label, which winds up being the best idea he ever had in his life, or one of the best ideas he ever had in his life.

• 51:07David Senra?

  But he goes back to studying the greats. And this is gonna be, I mentioned Rick Rubin, one of the co-founders of Def Jam. This is the guy, Russell Simmons, who essentially is the first rap mogul. So he says, "When I was moving off the street and tried to envision what winning looked like, it was Russell Simmons." Going back, see what I mean, how it blows your mind, or blew my mind? How much of this book is Jay-Z just studying the great people that came before him? Russell was a star, the one who created the whole model for the hip-hop mogul that many people, like Andre, Harold, Puff Daddy, and even Suge Knight, went on to follow. People in the record business had always made a lot of money, not the artists, who'd kept dying broke, but the execs. Still, regular fans had no idea who they were. Russell changed that.

• 51:52David Senra?

  His brand as an executive mattered not just within the industry, but among people in the street. And with Def Jam, he created one of the most powerful brands in the history of American entertainment. Russell also made being a CEO seem like a better deal than being an artist. He was living life crazy, fucking with models, writing in Bentleys with his sneakers sticking out the window. With his sneakers sticking out the window and never once wrapped a single bar. His gif was curating a whole lifestyle, music, fashion, comedy, film, and then selling it. He didn't just create the hip hop business model, he changed the business style of a whole generation of Americans. The whole vibe of startup companies in Silicon Valley with 25-year-old CEOs wearing shell

• 52:35David Senra?

  toes is Russell's Def Jam style filtered through different industries. The business idea, so he's still talking about all the lessons he learned before he met Russell. The business ideal for, the business ideal for a whole generation went from growing up and wearing a suit every day to never growing up and wearing sneakers to the boardroom. I understood what Russell was on to. He discovered a way to work in the legit world, but to live the dream of the hustler. Independence, wealth, and success outside of the mainstream rules. That's more founder mentality. Independence, wealth, and success outside of the mainstream, mainstream's rules. This was a better story than just being a rapper, especially based on what I now knew

• 53:20David Senra?

  about how rappers got jerked. And so we moved on to a different page. He's about to meet Russell and I just wrote, "So many gems are on this page." So he says, "I first met Russell when Dame Biggs and I," so Dame dash Biggs Burke, I think is his last name, and Jay-Z were the three co-founders of Rockefeller Records before Jay-Z is going to wind up breaking off on his own later on. "I first met Russell with Dame Biggs and I were negotiating for a label deal with Rockefeller after Reasonable Doubt dropped." So his first out, at this point in the story, he's already in the, he's already decided, "Hey, I'm not going to sell drugs anymore. I'm going to dedicate all my time and effort into making it as at this," he says, "making it at this rap shit," is the way he puts it. So his first album comes out, doesn't sell a lot, but it's like critically, it's like, "Wow, this guy's really good."

• 54:03David Senra?

  So it says, "I remember sitting across the table from him and Lior Cohen." This is a really, remember Lior Cohen from later on in the story too, because Lior is really important to the story because he's one of, he's one of Jay-Z's mentors and is also, again, Jay-Z, he's demonstrated like, "I'm going to find the smartest people that know more than I do and I'm going to learn everything I can from them," right? And so he does that with Lior, he becomes, like, Lior becomes his mentor and this causes a rift between Jay and his co-founders. As he says, "I remember sitting across the table from him and Leo Cohen in disbelief that we were negotiating a seven-figure deal with the greatest label in rap history. But I was feeling a dilemma. I was looking at Russell and thinking, I want to be this

• 54:43David Senra?

  dude, not his artist. Russell would become a valuable, informal mentor for me. He knew that the key to success was believing in the quality of your own product enough to make people do business with you on your terms. He knew that great product was the ultimate advantage in competition. Not how big your office building is, or how deep your pockets are, or who you know. In the end, it came down to having a great product and the hustle to move it. He knew the culture's power and was never shy about leveraging it and making sure that it was the people who were creating the culture who got rich off of it." So let's stop here, this flashback. Just like Jay-Z said at the very beginning, "I

• 55:28David Senra?

  knew hip-hop was new. I just knew one thing, and I knew it in my bones. I knew it was going to be bigger than it was. It's going to be bigger in the future than it is today before it dies." Well, the analogy here is Russell knew how valuable. Russell was one of the first people that knew that the birth of the hip-hop industry was going to make billionaires. He knew it. He was one of the first people to profit off of it. And the whole part is like, "We're the ones in control. We're the ones making..." It's what Steve Jobs said, "The most important people in the company are the people that are making your product. The people that can create wonderful products, both in Apple and Pixar, those are the people that are valuable. And the way to build a strong company is to make sure that those people are the most important people in the company." And what Steve Jobs learned from getting kicked

• 56:13David Senra?

  out of Apple is like, "Oh, we used to be the most important people in the company. Then when we build a product that turns a company into a rocket ship, then they bring in like adults, they start prioritizing sales and marketing, and then eventually you've already peaked, you don't even know it. You're like the Walking Dead. And 10 years later, everybody that's capable of creating great product has left." So in the end, it came down to having a great product and a hustle to move it. So build and sell and you will become unstoppable. That is Naval Ravikant from The Almanac of Naval. I can't remember what podcast number that is, but you can find it in the archive. He knew if you can build and sell, you will be unstoppable. He knew the culture's power was never shot about leveraging it to making sure that it was the people who creating the culture who got rich off it. That was the idea.

• 56:57David Senra?

  Now, this is, again, I'm still on the same page. So many gems on this page. And I'm reading you almost the whole page. It's amazing. The idea was at the heart of Rockaware. So this is a company that they're going to start. They wind up selling. So Jay-Z sold multiple companies for hundreds of millions of dollars. Rockaware, he sold for 200 million. I forgot how much he sold his liquor company for. He's got a few liquor companies. He just sold Tidal to Jack Dorsey at Square for like 400 million. So he just does this over and over again. The idea was at the heart of Rockaware. I mean, that's how you wind up being able to live in a 100 million dollar house, right? The idea was at the heart of Rockaware. The clothing company we founded. In the late 90s, I was wearing a lot of clothes from this company called Iceberg. After a while, I'd look out into the audience at my concert and see hundreds of people rocking Iceberg. The executives at Iceberg looked at us like we were speaking a foreign language.

• 57:41David Senra?

  So they wanted to do a partnership deal. They wanted to get paid for their influence of sales, right? They go meet, executives are like, nah, get out of here. They looked at us like we were speaking foreign language. They offered us free clothes, but we wanted millions. We walked out of their office realizing that we had to do it ourselves. And so what he realizes is like, forget endorsing other people's products. I'm not doing that. I'm making my own. If you'll buy a T-shirt that you see me in, the T-shirt should be owned by me. If you go to the club and order a drink like Cristal or whatever else, because I rap about it, then I should just rap about, like, I should own everything. It's like, almost like a form of like vertical integration. And so he talks about this, like, forget Timberland, forget Cravassier, forget Versace and all that other stuff, like, we're going to make our own stuff.

• 58:25David Senra?

  And he just got a great line, like, what story are you telling about your product? And he says, "We gave those brands a narrative, which is one of the reasons anyone buys anything to own not just a product, but to become part of a story." That line could have came directly out of Coco Chanel's mouth. She said the exact, the sentiment behind that line is exactly what, how she built her massive, massive empire around. It's why anybody buys anything, not to just own a product, but to become part of the story. And although, so he picks up on something about change in his outlook on things in life, that he becomes older and wiser and just learns more. One thing like, like was interesting is like, you know, you have all these like rap beefs

• 59:10David Senra?

  and rap battles and they make songs about each other and all this other stuff. And it's still, you know, these people still fight over this stuff today. And when I was younger, I really liked that, that like the art form is very interesting. And as I get older, I'm like, this is kind of dumb. Like, if I'm making music and somebody else is making music and somebody's, that other person's making music says something bad about my music, like, the best thing for me to do is to ignore and outperform them, right? Instead of me giving them attention. Now, some of this is like all fake and they do, it's like, you know, wrestling thing where it's like, we, if we have this fake beef, we'll sell more records and stuff. But I think in general, it's like, I don't care what other people are doing. I'm just focused on me and my product and getting the word, the word out. Like, I just think that's smarter. And so, that's what he's realizing here. He's like, I'm not gonna freaking argue with every single person that comes at me.

• 59:55David Senra?

  Like, this is just, I don't have that much time. So he says, "I don't scrap with every up and comer these days. I got so many people coming at me, I'd never do anything else. I'm not competing with rappers anymore. I look at things a little differently than I used to. The competition isn't always zero sum like it was when we were on the streets. I discovered that there really is such a thing as a win-win situation." So his whole point is like, this is all zero, this is not a zero-sum game. You can like my music, you can like that person's music, you can like that woman's music, and like, it goes on forever. So he says, "I discovered there really is such a thing as a win-win situation. I'm only competing with myself to be a better artist and businessman, to be a better person with a broader vision. This is genius, this is exactly what we should be doing. I'm only competing with myself to be a better artist and businessman, to be a better person with a broader vision. I'm still that dude on the corner," and he talks about the mindset he has.

• 1:00:38David Senra?

  "I'm still that dude on the corner, seven nights straight, trying to get back the money I lost. I'm still the kid who'd fight to be able to walk through a park. I'm still the emcee who'd battle anyone in a project courtyard." So he's not saying this literally, he's saying, he's like, "I still have that mindset. This is what the streets have done for us. They, what they have done for me. They've given us a drive, they've made us stronger. Through hip-hop, we found a way to redeem these lessons and to use them to change the world." So this is just fantastic, too. The note left myself on this page is, "This is just great. It's a million dollars worth of game for $9.99." That is a line he said in his album 444. What he means is like, you're buying an album for 10 bucks and you're gonna get a million dollars worth of ideas for it. Very similar to what they said in Poor Charlie's Almanack, founder's number 90, if you haven't listened to that, where it said, "There's 30," the reason that all, like, when you study-

• 1:01:23David Senra?

  The best founders and the best investors, like, they all have deep historical knowledge. And the reason is, is a line in Poor Charlie's Almanack. They said, "There's ideas worth billions of dollars in a $30 history book." And so, this is just fantastic. So, he's going to analyze the career and life of Jean-Michel Basquiat, who, if you listen to Jay-Z music, you know who he is, because he won't shut up about him. And he's just talking about, he's analyzing his work, taking the good ideas, right? And then avoiding the bad. It's exactly what we're doing. Basquiat was from Brooklyn, like me. He started off living in the streets as a graffiti artist. He was hanging around with Madonna before she was famous, and he collaborated with Andy Warhol. He came onto the scene with a crew of graffiti writers, but he didn't want to be boxed in with that movement. So, when the graffiti scene died, he didn't die with it.

• 1:02:08David Senra?

  He moved in a white art world, but flooded his art with black images, attitudes, and icons. He wanted to be the most famous artist in the world. So, I double underlined that section, because Jay-Z may not want to be the most famous, but he wants to be the best. He wants to be the best artist in the world. He was hip-hop when hip-hop was still in its cradle. So, he's seeing things in Basquiat's art, and he's realizing that same theme that's running through his art is exactly the foundations of this industry that I just jumped into. On the night he died, he was 27. Basquiat had been planning to see a Run DMC show. When people asked him what his art was about, he'd hit them with the same three words over and over again: royalty, heroism, and the streets. When he died in 1988, I'm not sure I knew who he was, even though he was a Brooklyn

• 1:02:53David Senra?

  kid like me, and he wasn't that much older. And so, then he's saying, "Basquiat wound up getting his wish, but he got it in death. You don't want to get your wish in death, you want it in life." He's probably among the most famous artists in the world, two decades after his death. I own a few of his paintings. "His technique feels like hip-hop." Another sentence I underlined, twice. "His technique feels like hip-hop." This is where he's, again, don't think of things literally. The one thing you learn if you study the life of Claude Shannon, the inventor of information theories, like, he looked at everything like a giant abstraction, which is what you, you know, try and do with these books. His technique feels like hip hop in the way he combined different traditions and techniques to create something new. Okay? He brought together elements of street art and European old masters. He combined painting and writing.

• 1:03:36David Senra?

  He combined icons from Christianity and Santeria and voodoo. And on top of all that mixing and matching, he added his own genius. Bingo. Exactly. Which, and this is why you do that, which transformed the work into something completely fresh and original. So you go study the career, the life and career of Steve Jobs and you see elements that he learned from Edwin Land, which he called his hero. He called Edwin Land a national treasure. You see Edwin Land's ideas in the back of Steve Jobs, like the influence, the veins of influence runs through Steve Jobs' approach to his work. It's not Edwin Land's ideas. It's Edwin Land's ideas mixed in with Steve's own genius, which then transforms Steve's

• 1:04:20David Senra?

  work into something completely fresh and original. And if you want to put a price tag on it, what is it? Multiple trillion dollar market cap. It's insane. Basquiat's work often deals with fame and success, the story of what happens when you actually get the things that you would die for. One Basquiat painting I own is called Charles the First. It's about Charlie Parker, the jazz pioneer who died young of a heroin overdose, just like Basquiat. In the corner of the paintings are the words, "Most kings get their head cut off." So why is he telling us this? Why is he bringing it up? Is he just bragging about that he's got really expensive art on his walls? No. This is the important part.

• 1:05:01David Senra?

  And the reason I collect maxims and song lyrics and short form videos. I read, so he's talking about looking at that, walking in the corner in his house and seeing that painting on the wall. "Most kings get their heads cut off." It's the reason why I have Ernest Shackleton on my lock screen on my phone. Why? Because I see Ernest, I see Shackleton covered in snow, looking like death, and I'm immediately reminded of his motto, "By endurance we conquer." So when I look at my phone, I see, "Oh, you're gonna give up, David? You're really gonna do that? No, you're not gonna conquer anything. By endurance. Get used to taking pain."

• 1:05:42David Senra?

  And then when you open my phone, it's a line, a screenshot from The Last Dance, the biography of Michael Jordan, a guy that was totally focused on one thing and one thing only. So we see this, it's very common for people to have these little reminders set around their house. Same reason I leave the book, The Tao of Charlie Munger out, The Bed of Hercrustes, autobiography of a restless mind. These are just like little books that I leave in places in my house. So I just pick up, they're books of maxims and aphorisms. It's not to sit there and read for 15 minutes, pick one up for two minutes, read an aphorism, a maxim, turn to a random page, and it's going to prompt your thinking, right? It's going to remind you of things, just like Jay-Z's sitting in his big, beautiful house, looking at this Basquiat painting, and he's saying, "Most kings get their heads cut off."

• 1:06:27David Senra?

  This is what Jay-Z says. I read it as a statement about what happens when you achieve a certain position. People want to take your head, your crown, your title. They want to emasculate you. And you resist it until one day, your albums aren't moving, and the shows aren't filling up, and it seems like the game might have moved on without you. And this is the problem. You do exactly what you shouldn't. Then you start to change, and you do whatever you need to get back into that spotlight. And that is when you're the walking dead. So in that margin of that paragraph, I wrote, "Steve Jobs avoided that. Look at the weird, crazy arc of Steve Jobs's life." There were many times, like, "No, Steve, why are you..."

• 1:07:08David Senra?

  They said something about, he was trying to build really nice, expensive, Apple computers, when everybody was just buying, the market had shifted, and everybody was buying cheap PCs. And there's a line in that book, in Steve Jobs by Isaacson, it says, "Apple's problem is that they still believe the way to grow is serving caviar in a world that seems pretty content with cheese and crackers." "I'm not here to serve you cheese and crackers," Steve Jobs said. "I'm building insanely great products because that's what I feel I should do. And if I start to change and just build an undifferentiated commodity PC like everybody else is doing, then Apple never returns." He looked at Apple's, and this is, at this period, that line comes from when, this is

• 1:07:53David Senra?

  the late 90s, when Steve Jobs comes back to Apple, and he looks at the product lineup. He's like, "This lineup sucks. It's just too much stuff. All of it sucks. Let's get rid of it all, and we're going to build four products, and there's going to be four badass, insanely great products. And we're going to stake our claim, and we're going to rebuild our company on the quality of our fucking products." And that, that line of thinking, becomes the foundation for the greatest corporate turnaround the world has ever seen. Not sticking your finger up in the air and be like, hey, what's the, what, what way is the wind blowing? Oh, you don't like what I'm doing? Let me change. Let me do whatever I need to do, get it back in the spotlight. No, the spot, I'm going to build the best products and that's going to direct the spotlight. I'm not going to just copy you and go down this crappy path. That reminds me of this fantastic, fantastic anecdote that's in Joni, or Jon, I said it again.

• 1:08:37David Senra?

  I did a whole podcast on it. Johnny, his name is Johnny, Johnny Ive's biography, it's Johnny Ive, the genius behind Apple's greatest products. And so, at the time, the market, the market demand saying, everybody, all the undifferentiated PC makers were building these things called netbooks. And they go from being like nothing to the laptop market to like 20% of the laptop market. And when, when they were talking, it was like, should we build a netbook? Steve Jobs just nailed it. And you only know this by being authentic to yourself. And he says, even though they were 20% of the market, Apple never seriously considered making one. And Steve said, "Netbooks aren't better than anything." Steve Jobs said at the time. "They're just cheap laptops." And so he's like, "No, I'm not building that because they're not better, they don't do anything better than any other product.

• 1:09:21David Senra?

  They're just, they're just popular because people are mass producing them and buying them." And so, instead of dedicating time to build a netbook, you know what, what, what Steve directed Apple's resources at building instead? The iPad. That is why that, what Steve, or excuse me, what Jay-Z is describing to us is so important. So, back to this paragraph. "Nearly every rapper who made it big has had to deal with getting one of his heads chopped off. The stories you hear can really make it seem like success can be a curse." And so, what Jay-Z's describing us is, this is what Jay had had to successfully navigate his way through. "The stories you hear can really make it seem like success can be a curse. Rappers who have been dangled over balconies for their publishing money." That's a true story, by the way. Held by their ankles, signed this contract and were gonna drop it off the balcony.

• 1:10:06David Senra?

  Driven out of their hometowns, fucked up by drugs, sued by their own families, betrayed by their best friends, sold out by their crews. There are rappers who blow up and blow through whole fortunes. They squander every opportunity and before you know it, end up back on the block. And so this is why this book is really hitting hard for me, hitting home for me. Is because there's a bunch of other people that I like their music. The same time I discovered Jay-Z's music 20 years ago. And let's say there was 20 of them. How many of them are still surviving to this day? How many of, how many of them did not successfully navigate through that labyrinth? Of what he, of what Jay-Z just described to us? It's a handful, a handful.

• 1:10:47David Senra?

  You can, and let's put that number, there's been thousands of people that have, that have made a hit rap, hit, a hit song. How many of them are still doing it decade after decade after decade? That's what I'm interested in. I'm not being, I'm not interested in being good at podcasting for a year or two. But a decade after decade after decade, because that is what my heroes did. Steve Jobs is a hero. He worked on his career for 40 years. Charlie Munger and Warren Buffett are still at it. Enzo Ferrari died. The Enzo Ferrari's exit strategy was death. Edwin Land ran his company longer than almost any other American business, uh, business founder, or excuse me, any other founder in American business history. Steven Spielberg is still at it. All these other people I look up to and admire for different reasons, like the one thing that they all have in common is longevity.

• 1:11:33David Senra?

  Jay-Z, same thing, longevity. So you take maybe thousands of people that had a hit song like Jay-Z did, and maybe five are still doing it for as long, maybe three or four, whatever the number is, are still doing it as long as he is. That, that long-term success is the ultimate goal. And so I turned the page and he's back at it and this is what I wrote. He just gets it. Jay just has the ability to connect the dots. I'm lucky never, I'm also lucky never to have needed the approval of the gatekeepers in the industry because from the start, we came in the game as entrepreneurs. That gave me the freedom to just be myself, which is the secret to any long-term success. But exactly what we just talked about with Steve Jobs, right? That is a secret to any long-term success, but that's hard to see when you're young

• 1:12:17David Senra?

  and desperate just to be put on, just to get, just to get put on. I don't accept, and I ran over my own point I just said a minute ago, this is the goal here. I don't accept that failing is inevitable. I think there's a way to avoid it, a way to win, to get success and it spoils, and to get away with it without losing your soul, or your life, or both. That's exactly what Jay-Z's able to accomplish. I'm trying to rewrite the old script, but Basquiat's painting sits on my wall like a warning. Few pages later, just one line here, reminder that this is something I learned from Bill Gurley. Be the best informed person in your field.

• 1:12:58David Senra?

  If you've never seen that fantastic talk, go to YouTube, type in "Runnin Down a Dream", how to survive and thrive in a career you love, I think it is. That's a, be the best person, be the best informed person in your field is a direct quote from that talk. And he says, "I'm a music head, so I listen to everything. People around me are passionate about music. We study music. We seek it out." Then he talks about, he's like, "You shouldn't be an artist, you should be a businessman. You should approach your art as a business." And again, really, he's just listing the pitfalls of the game that he was able to avoid. And so this idea, it's funny because everybody's like, they describe like this, the emergence of what they call quote-unquote "the creator economy." That is not a no idea. Back in 2005, and I think Jay-Z put it better than the term creator economy, he says, "I'm not a businessman.

• 1:13:43David Senra?

  I'm a business man." The other part of commercialization is the idea that artists should only be thinking about their art and not about the business side of what we do. When I committed to a career in rap, I wasn't taking a vow of poverty. I saw it as another hustle. Exactly. Dead on. It's just another product to move. I saw it as another, just how he happens to love and be obsessed with it. And obviously, the intent, or the, like, reading through the lines there is that that increases his ability, the likelihood of his success. I wasn't taken aback of poverty. I saw it as another hustle, one that happened to coincide with my natural talents. So I mind my business and I don't apologize for it. There's this sick fascination with the dead artist, the broke artist, the drugged-out artist. And another thing that's kind of surprising is how much Jay-Z talks about, like, don't

• 1:14:28David Senra?

  drink all the time, don't smoke weed, don't do coke, like, have a clear head. There's a fantastic story about him and Biggie with regard to that, I'll get to it in a minute. There's a sick fascination with the dead artist, the broke artist, the drugged-out artist, the artist who blows all of his money on drugs and big chains and ends up on a VH1 special. And he's just saying, he's like, "I'm not doing that. You're not going to catch me slipping like that." So then we get to the point where he's analyzing one of his freestyles, I'm going to skip the line, I want to tell you just a few sentences, two sentences, I think, about what he's talking about. And again, Bob Noyes, Estee Lauder, Edwin Land, Steve Jobs, Arnold, Jay-Z, they all do this in the song. "I keep talking about seeing it all before," and it's true.

• 1:15:10David Senra?

  "Not that I was prophetic, but I have always used visualization the way athletes do, to conjure reality. The mind is a powerful place, and what you feed it can affect you in powerful ways." And so I think for a lot of people, they think, "Oh, this is weird, you know, that's like willy-fu-fu stuff." Well, I see it all the time. I don't know what to tell you. I remember I was having coffee with a listener of the podcast, Seth, he's a founder and investor, and he's around the same age, and we both arrived at the same conclusion when we were having this conversation. And we talked about, you know, like, when you're younger, you're kind of like, I think we both had like a more analytical bent, and the more life experience you have, and you also see in this book over and over again, the more you're like, wait, intuition, just because we don't understand it, doesn't mean it's not powerful. And there's some kind of evolutionary benefit to listening to your gut, whatever you want

• 1:15:55David Senra?

  to call it, intuition, gut, your mind, it doesn't matter, inner monologue, whatever word you happen to put on it. But before, I completely discounted anything that was like, humans scorn the abstract. Well, I was one of those people that scorned the abstract before I understood how valuable that is. There's something about having this positive mental attitude, having a belief in yourself, like, even if you're walking out into the unknown, you think that you have a good product, you think you have some traction on your business, but you have to believe that you are going to succeed, you have to see it in your mind and brainwash yourself. And I'm kind of doing the same thing when I'm reading these books. Like, it's impossible. Like, it is absolutely impossible to read biography after biography of people believing in themselves when they had no reason to believe in themselves and using that as fuel

• 1:16:37David Senra?

  to fuel their dreams and not have a profound sense of belief in your own ability and what you're doing. That's not something you can put in a spreadsheet, but it's very real and it's very valuable. Like, listen to yourself, like, your heart, your soul, your intuition, your gut, whatever it is. It's the same thing that Jay-Z sang there. "I always use visualization the way athletes do, to conjure reality." Okay, so now we get to, like I said, there's tons of fantastic stories in the book. This is on having dinner with Michael Jordan. So he says, "I also believe there's a lot to be learned from elite athletes. Sports are one of the great metaphors for life. I know I'm not alone when I say this, but I absolutely love Michael Jordan. His career was a perfectly composed story about will.

• 1:17:22David Senra?

  I went to his restaurant at his invitation to have dinner with him." And so he's like, "This was just fantastic. I got to be a freaking, just an absolute fan, and I got to pepper him with any question I wanted to." So he says, "I found out how much Jordan loves Hakeem Olajuwon. He pointed out that Olajuwon was a leader in steals, which is rare in the center position. I asked him to name his five favorite centers, the best games he ever played, which championships meant the most to him. I got to be an unabashed fan. It was an absolute dream conversation for me. The things that distinguished Jordan wasn't just his talent," but this is the most important part, and it speaks to exactly like his dedication, the dedication that Jay-Z had in his craft, the one that Kanye, we mentioned earlier.

• 1:18:07David Senra?

  I'm locking myself, I'm doing, "Lock yourself in a room and do five beats a day for three summers. I deserve to do these numbers. The thing that distinguished Jordan wasn't just his talent, but his discipline, his laser-like commitment to excellence. That's something I always respect, especially in people who have great natural talents already." And so he's like, Jordan, that same approach that Jordan uses, I've seen it in other people. It's the through line through excellence. My earliest mentors in rap taught me that making music is work, whether it was jazz, locking himself in a room, working on different flows, or Big Daddy Kane, taking the time to meticulously put together a stage show. There's unquestionably magic involved in great music, songwriting, and performances.

• 1:18:52David Senra?

  Like those nights when a star athlete is totally in the zone and can't miss. But there's also work. Without the work, the magic won't come. There are 100 Harold Miners for every one Michael Jordan. So what he means, there's just plenty of people with talent. That's not enough. You've got to comply in discipline and laser-like commitment to excellence with your talent. And that becomes your, I guess, in the startup world you hear is they're looking for, they describe this phenomenon, this Jordan-esque phenomenon, as N of one founders. So that's the way you think about it. When you hear that, you think, oh, they're looking for the next Michael Jordan. And so Jay-Z talks about this because he also knows his rap, but he signs other rappers. When it comes to signing up new talent, that is what I'm looking for.

• 1:19:36David Senra?

  Not just someone who has skill, but someone who's built for this life. Someone who has the work ethic, the drive. The gift that Jordan had wasn't just that he was willing to do the work, but he loved doing it because he could feel himself getting stronger and ready for anything. That is the kind of consistency that you can get only by adding dead, serious discipline to whatever talent you have. And so one of these people that Jay-Z saw that in is, he winds up signing this rapper, who's one of my favorite rappers, like of the new school rappers, named J. Cole. And there was an interview Jay-Z was doing to promote his album. I think this was back in like 2013, 2014. He was releasing Magna Carta Holy Grail, that album. And he talked about the fact that him and J. Cole have albums coming out at the same

• 1:20:21David Senra?

  time. And he talks about the mentality that you should have. And he says, I know for a fact, J. Cole thinks his album is better than mine. And the next line is the sponge line. And he's supposed to. He is supposed to feel that way. That doesn't mean he's respectful to me. He learns a lot from me, just like I learned from-- and he says in the interview, he's like, "I'm studying Rakim, Big Daddy Kane, but I'm also competing with them." He's like, "You respect the people that came for you, but you're competing with them. You're supposed to." I know for a fact J. Cole thinks his album is better than mine. He's supposed to. You're supposed to feel that way. That is not something that people that don't have founder mentality, they can't wrap their mind around that.

• 1:21:04David Senra?

  So later on, he says something that's just a fantastic line, a fantastic point. He talks about, later on, he becomes like a business partner in this restaurant with Bono and Bill Clinton. And he's like, "I didn't really like the laws Bill Clinton passed. He was detrimental to people that looked like me and everything else." But he talks about meeting them and becoming friends with them. And he says, "But I'm not exactly-- and this is his great point. "But I'm not exactly the same person I was in 1992 either. Everyone needs a chance to evolve." Two great ideas on this page a little later on. "When you step outside of school and you have to teach yourself about life, you develop a different relationship to information. I've never been a purely linear thinker. You can see to my rhymes.

• 1:21:47David Senra?

  My mind is always jumping around, restless, making connections, mixing and matching ideas rather than marching in a straight line. Purely linear thinking will rarely get you from the projects to being a billionaire." That's obviously a good idea. "My mind is always jumping around, restless, making connections, mixing and matching ideas rather than marching in a straight line. It's exactly what I'm trying to do with founders. I'm trying to connect disparate thoughts. I've always believed in motion and action, in following connections wherever they take me and in not getting too entrenched. My life has been more poetry than prose, more about unpredictable leaps and lengths than simply steady movement or worse stagnation. It has allowed me to stay open," he's essentially saying the value of flexibility is what he's talking about here.

• 1:22:30David Senra?

  "It's allowed me to stay open to the next thing without feeling held back by a preconceived notion of what I'm supposed to be doing next."

• 1:22:38David Senra?

  And on this page, I just listed a bunch of people that optimized for flexibility too. Singleton, Herb Keller, Buffett, Munger, Nims Persia, the mountaineer we just covered a few podcasts ago, Chuck Feeney, the billionaire who wasn't, the guy that made $8 billion and gave it all away when he was still alive, Walter Chrysler, Henry Ford, Ed Catmull. They all say things just like what Jay-Z is saying here. Allowed me to stay open to the next thing without feeling held back by a preconceived notion of what I'm supposed to be doing next. So then he goes back to his childhood, and this is just insane. These are lessons from his dad. And just imagine, like, it's one thing, and they're both terrible, obviously, but it's one thing if like, you're never part of your kid's life and you ran away.

• 1:23:21David Senra?

  I still think it's cowardly, despicable behavior. But what his dad did to him is even worse. Imagine walking out on your nine-year-old son. So he raised his son for the first nine years of his life and then disappears and doesn't see him until, right before he dies, a few weeks before he died, they wind up meeting again. So this is my, I just cannot, I have a nine-year-old daughter. She's about to turn 10. Like, the idea that it would, like, that is just, you have to be so, something wrong. I remember one of my oldest friends, his friend, and I don't know how close he is to this, his friend, they went to college together, but he said that his friend did this, where it's just like, he got a girl pregnant and then just dipped out and never, like, didn't

• 1:24:01David Senra?

  support the kid and did, like, just completely, like, abandoned his responsibilities as a father. And I was like, you, and I told my friend, I was like, never talk to that dude again. Like, that's a scumbag. Like, he doesn't care for his own kids, he doesn't care for shit about you. And he thought, like, I was being harsh. And he's like, well, what if, and we'd been friends at that point, probably like 15 years when I was having this conversation with him. And he's like, well, what if I did that? I was like, I'd never talk to you again. Like, this is a despicable, despicable behavior. Like, you're destroyed, like, kids don't deserve that. You're the adult, you're the one that, like, had the responsibility, you're the one that had the sex, you're the one that did the, like, you're the one that made, helped make that baby.

• 1:24:43David Senra?

  Like, you take, it doesn't mean you have to be with the, like, the mom, obviously, and everything else, but like, you have to support your kid. And so Jay-Z talks a lot about that, not only in his lyrics, but in the book, about his generation really did their best to flip, because he's like, it was extremely common that... Our mothers would raise us, the dads were never around. And so we try to take that curse, that generational curse and fix it. And be like, yo, if you do this, you're a sucker. That's the way he puts it. My father was crazy for detail. I get that from him. Even though he didn't, we didn't live together after I was nine, there were some things he instilled in me early that I never lost. There was nothing he missed about a person. He was really good about taking it all in, taking in all the nonverbal clues people give you to their character. How to listen to the matrix of a conversation, to what a person doesn't say.

• 1:25:27David Senra?

  For my pops, it was just as important to take in places as people. He wanted me to know my own neighborhood inside and out. When I was walking with him, he'd always walk real fast. He said if someone following, he did that because if someone's following you, they'll lose you. And he expected not only to keep up with him, not only for you to keep up with him, but to remember the details of the things I was passing. He was teaching me to be confident and aware of my surroundings. There's no better survival skill than you could teach a boy in the ghetto. And he did it by showing me. And so then he talks about the fact that his dad left and that hip hop took this as like, hey, we gotta change this. The hip hop generation never gets credit for this, but those songs changed things in the hood. They were political commentary, but they weren't based on theory or books.

• 1:26:12David Senra?

  They were based on reality, on close observation of the world we grew up in. The songs weren't moralistic, but they created a stigma around certain kinds of behavior. Just by describing them truthfully and with clarity. One of the things we corrected was the absent father karma our fathers' generation created. We made, and Jay-Z puts it very eloquently, more eloquently than I could put it. And he says, we made it some real bitch shit to bounce on your kids. We as a generation made it shameful to not be there for your kids. So then he goes back to the burden of growing up poor and how you never, and I've seen this, what he's about to describe to us. I've seen this in a lot of the books that we've read as well.

• 1:26:57David Senra?

  The burden of poverty isn't just that you don't always have the things you need. It's the feeling of being embarrassed every day of your life and that you'd do anything to lift that burden. I remember coming back home from doing work, so selling drugs, out of state with my boys in a caravan of Lexuses that we parked right in the middle of Marcy. I ran up to my mom's apartment to get something and looked out at the window and saw those three new Lexuses gleaming in the sun. And I thought, man, we're doing it. In retrospect, yeah, that was kind of ignorant. But at the time, I could just feel that stink and shame of being broke lifting off of me. And it felt beautiful. The sad shit is that you never really shake it all the way off, no matter how much money you get. And so all the way back, I think it's like founders 115, maybe, or 116, actually.

• 1:27:41David Senra?

  And it's Samuel Bronfman, who grew up extremely poor in Canada and winds up building the gigantic Seagram's business that produced generational wealth. He's one of the first examples of this thing, this topic you and I've talked about a few times, which is the generational inflection point, where you have an entire family, a history of a family seeped in poverty, and you have the one, like Neo, like The Matrix, like you have the one, the one person that's going to change the generational inflection point, that changes the trajectory of the future generations forever. Sam Bronfman is that one in his family. And it's certainly the role I'm trying to play in my family. And it says, "Sam recorded little of his childhood, except to reiterate how painfully he experienced the poverty in which his family lived.

• 1:28:23David Senra?

  He worried that his parents might fail to make their payments on the family home. Sam later recalled the shame of appearing before his classmates in torn clothes. A humiliation he recounted to his own children the rest of his life." His daughter in the book talks about, they're living in a giant mansion. And he'd bring up the fact that he would have to go to school, be around his peers in torn clothes, and he would shiver, literally many decades later, shiver at that thought. And what did Jay-Z just say? "The sad shit is that you never really shake it all the way off, no matter how much money you get." It's the exact same idea.

• 1:29:05David Senra?

  So Jay-Z talks about the value of mentorship. Really think about this, the mentorship you either get in books or in person is just a way to speed up time, right? It accelerates, it accelerates the learning curve because you can learn from their experiences. You don't have to put in the 15 years that they put in. So Leo Cohen, who I consider my mentor, once told me something that he was told by a rabbi about the eight degrees of giving in Judaism. So I didn't know where this came from, but I've heard Jay-Z rap about this before. The seventh degree is giving anonymously. So you don't know who you're giving to and the person on the receiving end doesn't know who gave. The value of that is that the person receiving doesn't have to feel some kind of obligation to the giver and the person giving isn't doing it with an ulterior motive. The highest level of giving, the eighth, is giving in a way that makes the receiver self-sufficient.

• 1:29:50David Senra?

  So now we get to the point where he describes this as literally crossing over from one life to another. From going from, "I'm a full-time drug dealer," to "I'm a full-time rapper." All of these threads came together at a pivotal moment in me, the moment when I fully crossed over from one life to another. I was sitting across the table from Ruben Rodriguez, who was a music business vet, wearing the uniform. Double-breasted silk suit, pinky ring, tie. The room, the table, the view outside the window of a skyscraper, the whole scene was surreal to me. I'd been living like a vampire. The only people I'd seen in weeks were the people in my crew down south and of course the customers, the endless nighttime tide of fiends. My hands were raw from handling drugs and handling money. My nerves were shot from the pressure. Now I was in this office, sitting next to me was Dame Dash.

• 1:30:34David Senra?

  So this is going to be one of his co-founders. He says Clark Kent, the producer, so Clark Kent was a well-known New York producer and DJ. And he introduced, he's another important person in Jay-Z's life. He made beats for him, put him in the music business. He says, and he introduced him to a bunch of people. Clark Kent was the person who introduced me to Dame. Clark was pivotal at this stage in my life. In the mirror, all I saw was a hustler. Clark would find me and say, "Let's do this music." I appreciated him. Him, Clark Kent, Ty Ty, Bee Hi, all these other people, they would encourage me. But I was also skeptical about the business that I would also get, I was so skeptical about the business that I would get annoyed at them. Bee Hi, which is his cousin, used to really come down hard on me. He was real honest and direct and told me straight up, he thought I was throwing my life away.

• 1:31:19David Senra?

  Clark thought I had something, this is why, again, if we can encourage, especially younger people, like people, like it's just so important. Clark thought I had something new to offer to this world that he loved. So he's saying, I love your music. You have something new, something valuable. I want to help people discover it. He's like, stop dealing drugs, Jay. Take the rap shit seriously. You're good at it. Clark knew Dame was hungry, Dame Dash, was hungry for talent to represent so he could break into the music industry and thought we'd make a good match. Dame walked into the room and room talking and didn't stop. He was a Harlem dude through and through. Flashy, loud and animated.

• 1:32:01David Senra?

  He projected bulletproof confidence. That is important. He projected bulletproof confidence. And this is advice. I talked to a founder the other day and this topic came up where it's just like, he knows his stuff. He's got a good product that's valuable, but he's just like, I don't have the confidence. It's like, doesn't matter. Act like you do. Act like you do until you actually do. That's not even me. Like, that's not advice for me. That's the advice Nolan Bushnell gave to a 19-year-old Steve Jobs that Steve Jobs ran with. Nolan said, "Only the arrogant are self-confident enough to press their creative ideas on others." Steve believed he was always right and was willing to push harder and longer than other

• 1:32:43David Senra?

  people who might have had equally good ideas, but who caved under pressure. Dame Dash projected bulletproof confidence. If you're not like this, act like you are. Who cares? You have, just act like you are. So it goes more into the early days of them trying to hustle and just trying to, especially bootstrap is what they're doing. They're trying to bootstrap a record label. And again, this, no doubt of myself, many times in this, in this book, a lot can change in a lifetime from five dudes in an SUV and sharing hotel rooms to a billionaire. Every time Dame left these meetings, he'd get so heated. He couldn't believe that they didn't get me. But I wasn't surprised. I expected nothing from the industry. I just tried to shrug it off and I'd get back to my real life. Dame was getting frustrated trying to keep up with me. So he put together a makeshift tour to keep me focused on music.

• 1:33:25David Senra?

  Sometimes Dame and his group and I would just pile into a Pathfinder, Toyota Pathfinder, or Nissan Pathfinder, sorry, and do shows up and down the East Coast. I was being a team player. I piled in the truck, stayed in the double rooms with the rest of them. In some ways, these were like my college days, taking road trips. Jay-Z didn't even graduate high school if I'm not mistaken. In some ways, these were like my college days, taking road trips, bunked up with friends, learning my profession, except that I still had a full-time job selling drugs.

• 1:33:54David Senra?

  And so he's talking about like not trying to hide who he was, essentially on being human. This is one of the great, the things that make rap at its best. It's so human. It doesn't force you to pretend to be, to be only one thing or another, to be a saint or a sinner. It recognizes that you can be true to yourself and still have unexpected dimensions and opposing ideas. Having a devil on one soldier, shoulder, excuse me, and an angel on the other is the most common thing in the world. The real bullshit is when you act like you don't have contradictions inside you, that you don't have contradictions inside you, that you're so dull and unimaginative that your mind never changes or wanders into strange, unexpected places. And so now he's fast forward into his career a little bit, and the note I have myself that I've left on a lot of these books is how bad do you want it? There's all these examples in the book.

• 1:34:39David Senra?

  I'll just, I'll just give you one that pops in my mind because I just talked about it. Sam Bronfman, the generational inflection point, the one that made generational wealth and ended his family's curse of poverty. At the time, he's growing up in Canada, it's extremely cold. They're, they're learning, hey, we're going to sell liquor. You have to, at the time, they had like all these weird prohibition laws and things like that. And so, one way to get around that is you buy an existing hotel that's like grandfathered in, that's exempt from this law that allows you to sell liquor. He hears about a hotel that is for sale. There's another guy in the same town that lives, that he lives in, that also wants to bid on this hotel. Turns out the owner of the hotel is in the middle of nowhere, like the, like the middle of like icy tundra somewhere out in Canada hunting.

• 1:35:23David Senra?

  And so, you have Sam who wants the hotel, to make an offer on a hotel, you have Sam's competitor that wants to make a hotel, offer an hotel. They found out the guy's not going to be back for a few weeks. The other guy's like, okay, I'll just wait. Sam's like, all right, where's the guy at? He, he's in this remote, you know, Yukon Territory, or wherever it is. How do I get there? Oh, I have to rent a dog sled and I have to sled in the ice, in the freezing cold for six days and I can't bring food, so we have to hunt and kill our food on the way just to get to this guy's remote location? Yeah, I'll do that. Does that for six days in unbearable pain and struggle, gets to the guy's camp. You already know the end of the story, don't you? Who is going to get the deal?

• 1:36:06David Senra?

  Not the guy sitting on his ass back by the fire, waiting for this guy. The guy that went through it. So Sam Bronfman winds up getting, meeting the guy, negotiating a deal in the camp spot, and getting the hotel before that other guy, sitting with his feet up, even knew what hit him. And so, the way to summarize is that, how bad do you want it? Because there's extreme levels of drive and pain tolerance in the history of entrepreneurship. Okay, so, this isn't necessarily painful, but Jay-Z's not also one to take no for an answer. He's gonna describe how he gets the clearance for what becomes his biggest hit. So, he did this song called Hard Knock Life. This is on his second, excuse me, his third album, if I'm not mistaken.

• 1:36:48David Senra?

  It is before that, before Hard Knock Life, Jay-Z's critically acclaimed, not selling many records. After, he sells 5 million records, and he completely changes the trajectory of his entire career. And so, they have to get clearance from that movie, like Little Annie. I forgot the little, like, you know, the little redheaded girl. I forgot, Orphan Annie, or whatever her name is. To use the song from Annie, we had to get clearance from the copyright holder. "I wasn't surprised when the company that owned the rights sent our lawyers a letter turning us down. Lord knows what they thought I was gonna rap over that track. But I felt like the chorus to that song perfectly captured what little kids in the ghetto felt every day. Instead of kisses, we get kicked." So, that's the hook, right? "So, I decided to write the company a letter myself, after being rejected.

• 1:37:32David Senra?

  I made up this story about how, when I was a 7th grader in the ghetto, our teacher held an essay contest, and the three best papers won the writers a trip to the city to see Annie on Broadway. That was a lie. I wrote that, as kids in Brooklyn, we hardly ever came into the city. That was true. I wrote that from that moment on, or from the moment the curtain came up, I felt like I understood her story. Of course, I had never been to see Annie on Broadway, but I had seen the movie on TV. They bought it, they cleared it, and I had one of my biggest hits. How bad do you want it?"

• 1:38:08David Senra?

  And so the note I left myself a few pages later could also have applied to what Jay-Z just, the story Jay-Z just told us. When somebody puts up a wall in front of you, what do you do? You put up a wall in front of Jay-Z, Sam Bronfman, all these other people, they're knocking the wall down, they're tunneling under the wall, they're jumping over the wall. But that wall is not going to stop them. After every label in the industry turned us down, and I do mean every label in town, Dame, Biggs, and Izz decided, fuck it. Why be workers anyway? Being a recording artist on a major label is the most contractually exploitative, exploitative relationship you can have in America, and it's illegal. All three of us had read Hitman, which is this book, which is the industry bible, and we knew what kind of gangsters had established record companies. So in 1994, Dame, Biggs,

• 1:38:53David Senra?

  and Izz pooled our resources to form Rockefeller Records. Obviously, an homage to some degree of John D. Rockefeller. The name was aspirational and confrontational. The first record we made was called I Can't Get With That. We made in Clark Kent's basement studio, and we shot the video for $5,000. We pressed up our own vinyl, and we made champagne baskets and sent them to DJs. So he's just saying, he's like, doing things that don't scale, which is Paul Graham advice to startup founders. He's starting a business, and he just knows how to hustle. He's like, we don't have endless amount of money, so we gotta be resourceful here. So like, we're just do things on the low, we'll do things ourselves as much as

• 1:39:35David Senra?

  we can, and we're gonna, we're gonna push this and get the momentum of our label going. And so he says, we didn't know the business yet, but we knew how to hustle. We did more than talk about it. We wrote it down. The key thing is, we wrote it down. This is exactly what Arnold Schwarzenegger says. He's like, you gotta have a goal, you gotta write it down, and you gotta think about it. That's the only thing you think about. And so Jay-Z says, the key thing is, we wrote it down, which is as important as visualization and realizing success. How many times is he gonna talk about visualization, seeing it in your mind before he's seeing it in person? Over and over again. Back then, we'd go to record stores who still sold singles on consignment. This is wild. They, we would drop the single off and come back every couple of days to collect half the proceeds of what had been

• 1:40:18David Senra?

  sold. We'd show up and we'd collect $150.

• 1:40:23David Senra?

  I was right there in the stores politicking with the retailers and personally building relationships with DJs. It was do or die.

• 1:40:33David Senra?

  So they own all their records. The only thing they don't have is distribution. So they have to, then distribution usually takes like a 20% fee. In some of the videos I saved on my phone from Jay-Z, he's like 26 years old talking. He's like, "Yeah, own everything." I mean, I have actually, I wrote down what he says, hold on. He says, "I want full control over my," this is him, he's like 26 at the time. This is wild. "I want full control over my music." This sounds like George Lucas. "Try to own as much of yourself as possible because it's going to pay off in the long run." He's like, "We own everything except the 20% distribution fee and we're working on that." Young dude. And he knew back then. This is amazing. "We negotiated a deal with payday that guaranteed wider distribution than the one we'd be, than the distribution we'd be able to get on our own. Once we secured that deal, we rented an office in the financial district.

• 1:41:18David Senra?

  Check this out. We started a fan club before we even had any fans." So the note I left myself here, something I already told you from the Kanye documentary. "Before I had a car, I'd walk to the train practicing my Grammy speech." So they find a way to get their single on a, getting radio play, it's getting, it's getting popular. He's like, "Oh, I don't have the album done. I gotta hurry this up." Says, "We had a small window of opportunity from the time," this is, he calls him Flex, that's Funkmaster Flex, very famous DJ on Hot 97, which is a very big radio station in New York. Remember, this is way before streaming or any of that stuff. "We had a small window of opportunity from the time Flex started playing it in the beginning of 1996. I figured I had until the summer to complete an entire album." That's about three to four months from studio to a packaged product with a marketing plan.

• 1:42:02David Senra?

  "I don't think I slept for weeks at a time back then. I was living off of pure adrenaline." One of his singles that's going to be on the album, he actually gets through his relationship with Clark Kent. When Biggie Smalls came through one of my sessions to see Clark, Clark played him the beat for Brooklyn's Finest. He told Clark he had to get on it. I met Big and we clicked right away. More than anything, I love sharp people. Men or women, nothing makes me like someone more than intelligence. And then he talks about what it's like being on the forefront, on the frontier of a brand-new industry, and why brand-new industries usually attract a certain personality type. Rap started off so lawless, not giving a fuck about any rules or limits.

• 1:42:47David Senra?

  It was like a new frontier. We knew we were opening up new territory, even if we left behind a whole country or sometimes our own family. We struck oil.

• 1:42:58David Senra?

  And so then, this is when he gets into a fantastic Big story, and really, just a powerful lesson. So he says, "I hadn't been on vacation since I'd gotten serious about music, so I was happy to go to Miami to shoot the video for the song he's got with this other rapper named Foxy Brown. Big was touring, but he took the time out to fly down and make a cameo in the video. Big loved to smoke, so smoke weed, but I could count the number of times that I had smoked trees. Champagne and the occasional Malibu run were my thing back then, but mostly, I liked to stay sober. The better to stay focused on making money. I come from the class of hustlers who looked down on smoking as counterproductive. We used to judge dudes who smoked as slackers. When I did smoke, it was on vacation in the islands.

• 1:43:42David Senra?

  But when Big asked me to smoke with him, I told myself, 'Relax, you're not on the streets anymore.' It was happening, and I had to admit it. I was out of that life, so I smoked with Big, and he smoked blunts. The last time I had smoked, whenever that was, I'm pretty sure I was hitting a joint. A couple hits later, and I was high as shit, sitting there, feeling outside of time, slightly stuck, and laughing uncontrollably. Big leans in, so only I can hear him. I gotcha." That fucked me up. Big was a friend, but also a competitor. He gave me an important lesson at that moment. They call it the game, but it's not. You can want success all you want, but to get it, you can't falter. You can't slip. You can't sleep.

• 1:44:27David Senra?

  One eye open for real and forever. Big's joke was such a small thing, but I was like, fuck that. The director was setting up shots and all that. And I went to my room and I sobered up before I came downstairs. When I came down, Big was laughing. His laughter was a beautiful thing, even when the joke was on me. This time, I leaned in close to him. Never again, my dude. And so that might be surprising because maybe he mentions it as music, smoking or drinking. I mean, he sells alcohol for God's sake, right? But that's, it's really interesting. Like again, actions express priority, which might be my all time favorite maxim. Like what you do is what is actually important to you, not what you think in your mind or what you say.

• 1:45:08David Senra?

  And it's interesting, like he might rap about smoking blunt or drinking or whatever, but he's telling us, he's like, no, I actually don't like smoking that much. And I don't like drinking that much. Like I try to stay a clear mind. He talks about that too, it was like, especially in hip hop in the nineties, they glorified like going to the club. That was really big. They would hang out. And so he tells a story in the book where he would show up to do a performance. He'd get on stage at a club, do a couple of songs. And then people think, oh, Jay-Z's here. And in many cases, you'd even be like paid by the club to show up because it's like, oh, Jay-Z's here. So those more people come, the more alcohol they sell them, et cetera, et cetera. But he's like, what I would do is like, I'd get on stage, I'd rip it for 10 minutes and then I'd leave. I'd get in my car and I'd go home or go back to work or whatever. He's like, I'm not hanging out in the club. I'm not wasting time like that. So here we go.

• 1:45:53David Senra?

  Jay-Z talking again about studying and learning from the greats that came before him. Slick Rick was the wittiest shit out back then. He can make the rawest rhymes sound like masterpiece theater. And he had the kind of style that hustlers aspire to. His songs were energetic and hilarious. Like all great comics, he knew how to hide deeper emotion between his punchlines. He kept it clean and honest and respected his listeners enough not to manipulate them. Slick Rick taught me that not only can rap be emotionally expressive, it can express those feelings that you can't really name, which was important for me and a lot of kids like me who couldn't always find the language to make sense of our feelings. Then he talks about another guy that he was studying, which is Scarface.

• 1:46:33David Senra?

  And so he says, "Scarface is one of my favorite rappers and maybe the first truly great lyricists to come out of the South. He's known as a rapper's rapper, and it's true. He gets respect across the board and his influence is enormous. His music is an extended autobiography. Scarface always feels like he's rapping right in your ear, like the guy on the next bar stool unburdening himself of a story that keeps him up at nights, or a nightmare that comes back to him all day. The power of his stories come in part from his willingness to pull the covers off of taboos, to get into the shit that people pretend isn't really happening. And so that's why I try to bring up these crazy stories in the books, because I feel there's stories in the books that people are willing to share in like an autobiography or memoir form, that they just won't talk about in like

• 1:47:14David Senra?

  an interview or in otherwise. They'll talk about stuff in private, they're not talking about publicly. They'll put it in their books towards the end of their life. And so that line really hit me. His willingness to pull the covers off taboo, to get into shit that people pretend isn't really happening. So Scarface is also, I'm gonna really try to convince you to watch that Kanye documentary if you haven't seen it, but Scarface makes an appearance in that documentary. At this time, Kanye had produced a song or two from Scarface, and he asked Scarface to come to the studio to listen to his music. And so Scarface says two things that are really interesting. One, he pulls up, he's like, what the, like, at the time Kanye's having this video crew, like, follow him around.

• 1:47:58David Senra?

  And he's like, Scarface is like, "Why are the cameras here?" He's like, "Oh, they're doing a documentary on me." And he's like, "On who?" He's like, "On you." And, you know, Kanye's barely known. You might know him as like a supplier in industry, right? Just because he's making beats for people. And so Scarface says something about Kanye that really demonstrates the relentless resourcefulness that a young Kanye West had. Forget everything you know about him now, that's irrelevant. Study the first two episodes of this documentary, and tell me that's not founder mentality. Tell me that is not founder mentality. It's just amazing what he did, like, not only like put in 12 years of practice of his craft, but then to make people believe.

• 1:48:38David Senra?

  But Scarface says when he learns that the documentary accrues for him, he goes, "That goddamn Kanye be pulling rabbits out the hat, man." That is the perfect way to describe relentless resourcefulness. Pulling goddamn rabbits out the hat. Or, excuse me, "Goddamn Kanye be pulling rabbits out the hat, man." It's the exact quote. But anyways, the reason, the real reason it's important is because he goes in and he's like, "Listen, I know you like my beats. I want to play you music that I have rapped on." And so, and you see this in the video, that's why it's crazy, or in the documentary. He plays it, and this, again, Scarface at this point is a legend. One of the best to ever do it in what he, so think about it, it's like Kanye's aspiring to be, to just be taken serious as a rapper. Now, Scarface is taken serious as a rapper.

• 1:49:22David Senra?

  He's widely acknowledged as one of the best to ever do it. And so, he plays that song for him, and we get this on, on the documentary. It's on tape. And he says, "This is incredible." And then the narrator of the documentary says, "Getting validation from one of the best rappers alive was more encouragement for Kanye to keep moving forward." It is so important to encourage the next generation as much as you possibly can. This is a tale as old as time. Go back to Henry Ford. He's like, "This is weird, man." All the cars at the time, they're either steam, or they're electric cars. I'm really thinking that the internal combustion engine is like, it's self-contained, we can fuel it, it can go farther, it's more reliable, et cetera, et cetera. He winds up meeting his hero, right?

• 1:50:07David Senra?

  He didn't know him at the time, they wound up being really good friends, but at this time they weren't. He meets Thomas Edison. And he gets to explain his idea to Thomas Edison, and seven words changes, seven words, seven words from Thomas Edison changed the trajectory of Henry Ford's life. "You have the thing. Keep at it." And it says, "With encouragement from the man who Ford regarded as the greatest inventive genius in the world, ringing in his ears, Ford returned home with the conviction that he should persevere." Go back to the Kanye documentary. After Scarface leaves, Kanye is in the parking lot, beaming, beaming, full of energy and enthusiasm. And he said, "He said it was incredible. Getting validation from one of the best rappers alive was more encouragement for Kanye

• 1:50:52David Senra?

  to keep moving forward." So he goes back to studying them. Rick and Scarface, slick Rick and Scarface, share the ability to get under your skin by dredging up all kinds of emotions that young men don't normally talk about with each other. Regret, longing, fear, and even self-reproach. So then he talks about this, now he's fast-forwarding in the story because he's talking about, it's crazy, like I admire Scarface and I'm doing a song with him. And so he says, "On the verse I did with Scarface, I went into some dark, personal storytelling about a time in my life when I felt truly confused and lost. Every entrepreneur in the world has felt this before. I went into some dark, personal storytelling about a time in my life when I felt truly confused and lost. I was between worlds, the voice in my head screaming at me to leave the street shit alone. While outside, I watched Big and Nas blow up.

• 1:51:37David Senra?

  It was a verse about fear of failure, which is something everyone goes through, but no one, particularly where I'm from, wants to really talk about. But it's a song that a lot of people can connect to. The thought that this cannot be life is one that all of us have felt at some point or another, when a bad decision and bad luck and bad situations feel like too much to bear. Those times when we think, this, this cannot be my story. But facing up to that kind of feeling can be a powerful motivation to change. Amen. It was for me." And then he talks about, yeah, I struggled when I was younger, I survived a crazy environment, I did things that could have wound up getting me killed or in jail, and I survived.

• 1:52:21David Senra?

  But the feeling from that earlier struggle never goes away. Inside, there's still part of me that expects to wake up tomorrow in my bedroom in apartment 5C in Marcy, to slide on my gear, to run down the piss-filled stairway and hit the block with one eye over my shoulder. So then he talks about one of his songs that he feels is like a hidden gem in his catalog. It's "Beach Chair," featuring Chris Martin. It's on his Kingdom Come album, which is the album that Jay-Z thinks is his worst. But there's just two things from his interpretation of the song, from his explanation of the song, rather. And so, there's two things I want to pull out for you. First, there's a line in the song where it talks about, "I hear my angels singing to me," and then you hear Beyonce's voice, "Are you happy, Hove?"

• 1:53:06David Senra?

  Hove, obviously, being Jay-Z's nickname, in case you're not a listener to his music. So it says, "I hear my angels singing to me. Are you happy, Hove?" And so, this is why he put that in the song. "When you get things you think you'd always wanted, it doesn't stop the voice in your head's interrogation. If anything, it gets more insistent. When you get the things you think you've always wanted, it doesn't stop the voice in your head's interrogation. If anything, it gets more insistent." And then in the song, he talks about, "I'm not spending all my day tied into what other people are thinking or saying. Like, I give myself space so I can come up with something unique." So he says, "I'm not afraid of dying. I'm afraid of not trying. Every day, hit every wave like I'm Hawaiian. I don't surf the net.

• 1:53:50David Senra?

  No, I've never been on MySpace. I'm too busy letting my own voice vibrate, carving out MySpace." And so, what does that mean? "Give your brain space to think," just like Henry Singleton did this. He sat alone in his corner office with his Apple II computer, and that office produced a cornucopia of ideas. Jay-Z says, "It's always been most important for me to figure out MySpace, rather than to check out what everyone else is up to, minute by minute." And this hit me so hard. "Technology is making it easier to connect to other people, but maybe harder to keep connected to yourself." And that's essential, being connected to yourself, that is, for any artist, I think. And I've heard this song over and over again, and now that I read his interpretation of

• 1:54:33David Senra?

  it, it's just like when I say, like, if you, like, I start reading the biography of entrepreneurs, and you realize how much of their life went into what they do. Like, you appreciate an Apple product more if you know Steve Jobs' story. Like, you'll appreciate Trader Joe's more if you know Joe Colombo's story. Like, it's the same thing. And this song, I've heard it Thousand times, still didn't understand it as much as I should have. And really, what he's, it's just, and the fact that he doesn't write this down is just insane talent. So he is speaking, this is still the same song. He's speaking to his unborn child, and this is before he was a parent. And so he says, "This song is like a Hallmark card until you reach here." So he's speaking to his unborn child, okay? His unborn daughter. "This song is like a Hallmark card until you reach here.

• 1:55:18David Senra?

  So till she's here and she's declared the heir, I will prepare a blueprint for you to print, a map for you to get back, a guide for your eyes." He's essentially telling the story, I'm gonna start this over. He's doing exactly what a good parent does, right? We're trying to, I'm not trying to control your life. I'm trying to prepare you for what life can throw at you. "This song is like a Hallmark card until you reach here. So till she's here and she's declared the heir, I will prepare a blueprint for you to print, a map for you to get back, a guide for your eyes. And so you won't lose scent. I'll make a stink for you to think. I ink these verses full of prose so you won't get conned out of two cent.

• 1:56:01David Senra?

  My last will and testament, I leave my heir, my share of Rockefeller records and a shiny new beach chair." And so his interpretation of that is, I'm still trying to give this unborn child something more than just money. A blueprint for life, a map, a guide, a scent to follow. And I really do believe that that is why, how many autobiographies of 80 and 90-year-old entrepreneurs have you and I studied on this podcast? They know, like, I got a couple more years, man. Maybe I got a couple more months. And they just sit there and they write all their best nuggets of wisdom. And they're trying to give us something to follow. A blueprint, a map, a guide, a scent to follow.

• 1:56:43David Senra?

  And then I'll close with what Jay-Z says about the power of language and storytelling. What he's about to describe here is the same way. I feel the same way with these books. And I think that's why biographies hit so hard when you read them. Whether it's in a movie, or a television show, or whatever, the best characters get inside of us. We care about them. We love them. And we start to see ourselves in them. And in a crazy way, we become them. And that is where I'll leave it. I absolutely loved, loved reading this book. If you are a Jay-Z fan, no brainer, don't make the same mistake I did and not read it. Even if you're not a fan of his music, or you don't know much

• 1:57:24David Senra?

  about it, there's still just a ton of lessons, I think, from hearing his story that can be applied to your life. So if you want to get the full story, read the book. I'll leave a link in the show notes. If you buy the book using that link, you'll be supporting the podcast at the same time. If you want to give a gift description to somebody else, that link is below and is also available at founderspodcast.com. I'm seeing a lot of people do something that I think is really smart, something that I've seen other people do. Like Jeff Bezos talked about the importance of having a shared base of knowledge with coworkers. So they, like, executives in the early days of Amazon would read the same books. They'd have this basically shared base of knowledge. So I'm seeing a lot of people like the same, from the same company, buy gift descriptions for other people in the company. So in case you haven't thought about doing it, that's an opportunity. Links

• 1:58:05David Senra?

  down below, also at founderspodcast.com. That is 238 books down, 1,000 to go. And I'll talk to you again soon.