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If Kobe Bryant had lived, he would have been on How I Write.
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Jimmy Sony says that the whole world is a conspiracy to stop you from writing.
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He's the guest on today's show and he's done all kinds of writing.
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He's written books, op-eds, done the business stuff, you name it.
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He's working on a book about Kobe Bryant.
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And I didn't realize this.
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Kobe wanted to become the Walt Disney of the 21st century. That was his plan.
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So, he studied writing, he studied storytelling, and he obsessed to like the level of Kobe obsession.
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And then we got into the world of AI.
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How does Jimmy use it for editing, for research?
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And we got really tactical. Let's rock.
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Well, when we were chatting before this, you said the craziest thing to me.
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You said, "If Kobe Bryant was still alive, he would have been on How I Write."
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He would have been on How I Write.
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And I was like, "What do you mean? What do you mean?"
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He said, "I'll tell you when we get to the podcast." So, what do you mean? >> All right.
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Um, so I have to offer a bit of context for that comment because, you know, I I'm I'm 5'8 and never played professional basketball and, you know, grew up loving Jordan's Bulls.
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So, this is a little bit of a non sequator, but it's an important nonsequittor.
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So, around the pandemic, I was um I was like the pandemic was was it was rough.
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the pandemic was was it was rough. I would say it was particularly rough for parents of young kids because you you suddenly are like in this like you know you're you're caged with these like tiny creatures who are accustomed to having much more freedom and you all of a sudden like can't have them interact
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with other people at the beginning you have to be very careful about you didn't know enough about COVID all that stuff and so there's basically like you know people turn to different sources of relief for this they turn to whatever alcohol television whatever and My source of relief was I I needed to get through big projects. Uh the founders
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Uh the founders book which I was working on, business things, client things, and raising a daughter.
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I built a pod school and it was all very hard.
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And I just somehow stumbled onto this video of Kobe Bryant.
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It was like one of these like video interviews that he did where he was talking about discipline and mental toughness and resilience and going through the his Achilles injury and everything else.
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And honestly, just as a casual like like way of of providing myself like a morning's dose of inspiration, I would basically just wake up and like watch Kobe videos.
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And so what I did was I just every single morning for like a year, two years, I would wake up and the first the fir one of the first things I would do is I would watch like five minutes or eight minutes on Kobe.
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And the reason is and the more I started to do that, the more I started to realize that he was a much bigger figure than just like a successful basketball player.
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I I just at the level of like brass tax like he won an Academy Award, he won an Emmy, he was a successful investor, he had done all he's he's working on homelessness, he was a coach for his daughter's teams.
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So I started to learn more about him.
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And one of the things that I learned is that in his life after basketball, what he wanted to do was become a storyteller and become a preeminent storyteller.
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He wanted to be Walt Disney.
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He wanted to be Walt Disney for this generation.
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And so he had he had written or conceived of I think like five novels uh I think four of which came out.
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Four or five of which came out.
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He had written I think the beginnings of a Broadway musical.
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Uh there were screenplays in the works.
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He had a whole media ecosystem that he was building to to take storytelling and turn it into something.
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And at first, my reaction was probably the reaction of a lot of people. Well, good for him. He's a celebrity.
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He's got millions of dollars.
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He can do whatever he wants.
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No, the difference is that Kobe actually studied the craft of writing.
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So, every day for 15 years, he journaled.
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He studied Joseph Campbell.
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He studied the hero's journey. He read Hemingway.
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He would go interview writers. George RR Martin. Yeah.
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He would hang out with George RR Martin and they would like talk about writing and he would like pick his brain.
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He would go he he he loved JK Rowling's work.
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So he would go obsessively study it.
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He obsessively studied the art and craft of storytelling.
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And so what fast forward when we were talking I was like you know the person who would had he not you know met his untimely end he would have been a guest on this podcast because I think he actually loved writing and storytelling more than you and I do which is saying something.
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Um, and so what I decided to do with all of that is I I'm actually my next project is going to be a book in the spirit of like the almanac of Naval Ravocant or the Almanac of Charlie Mer and it's called the tow of Kobe.
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And so the idea is what happens if you look at him not just as a figure in sports but as a much bigger figure in self-improvement and excellence.
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And so I'm collecting all of these quotes from about 400 450 interviews and kind of stitching them together into a story of his life that I don't think most people are familiar with.
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There's something that also happened that you didn't mention which is he won an Oscar. Yeah.
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>> For best animated short film. >> Yeah.
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So the story there is actually it's a such a cool story and to me the inspiring thing is that all right there's a few inspiring angles.
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one is, you know, you're you're this person who's at the top of his craft in one craft, basketball, and the the typical route for someone like that after they leave the game is to like go do TV or go be like a celebrity spokesperson, right?
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Go sell whatever, tires, grills, cars, anything, right?
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And when he was in the year before, year or two before he was getting ready to leave the game, people would ask him what he wanted to do next, and he would say, "I want to be a storyteller."
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And they would basically laugh at him.
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Like he had he had he would they would laugh.
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They would say like, "Oh, that's cute."
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Like when what are you going to do when you get serious, right?
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And so part of what they didn't know is how much time he had spent actually trying to become a better writer.
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This was a process that started when he was in high school.
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He had a really good English teacher.
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She got him inspired about storytelling.
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So he started just like working on things.
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So for example, people don't know, he was the ghostriter behind most of his ads. So all of his shoe ads. Yeah.
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He wrote all of his own shoe ads.
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And he would do the copy and then work with other people.
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But he was actually the pen behind a lot of his ads. He wrote rap music.
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It didn't do well, but he was like at least interested.
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And he actually talked about how rap doing rap taught him how to think about like musicality in words and harmony and the ways things fit together.
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>> I saw also how much >> how much you can pack a punch in a sentence.
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Rap like really force you to compress your language.
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>> And for him it was a little bit of a source of embarrassment because there was these like videos of him like rapping and stuff that were not the best, but it taught him a lot about writing.
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So when he is getting ready to leave the game of basketball, again, typical way you do this, you you have a press conference, right?
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You like assemble the mat, you assemble the cameras, you assemble your your whoever, your family, your friends, and you announce to that you're leaving.
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He decided to write a poem.
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So he wrote a poem called Dear Basketball that was published on Players Tribune, and it it was entirely his work.
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He wrote it, I think, in like one sitting or something, but it had taken a lot of time, obviously, to nurture these thoughts.
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and he called it a love letter to the game.
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So the idea was that he was going to write a letter to the game of he was anthropomorphizing basketball and saying I'm gonna write a letter to you basketball.
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So that's why it was called your basketball.
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He writes it and then this is sort of vintage Kobe.
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He starts to think about what else you could do with something like that because it made a real impact.
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Nobody had ever done this before.
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I mean these this is not the typical behavior of any elite athlete, right?
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Um he he had been in touch with John Williams of kind of symphonic fame, Star Wars, all the you know he's done every musical score that's important for the last whatever 25 30 years and Glenn Keane who was a Pixar animator who was most famous for I think doing Little Mermaid or something.
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He had done like some amaz like series of of different Pixar films that have been amazing.
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He had been in touch with them and he basically had this idea for turning the poem into an animated short.
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And so he went to them with the idea and said, "Listen, I have this concept.
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I want to turn this into a film.
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I think it could be a short film, but I think it needs handdrawn animation."
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And then he essentially just like like picked up the phone, talked to John Williams and said, "Would you be willing to do this?"
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And and John >> for the score >> for the score for the music.
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And John was like, "Well, I'm in the middle of Star Wars right now, so can you wait a little bit?"
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And then and like Kobe's response was like, "Yeah, I could wait a little bit." Right.
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And so he puts this team together and they they do this short film.
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No one knows how it's going to do.
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He doesn't know how it's going to do.
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And then it's it's a marvel. Like it's a triumph.
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It's beautiful and it's beautifully done.
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And he is a you know Academy Award finalist.
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And then they announce his name and he's won.
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And it's this incredible.
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He was the first athlete to ever win an Academy Award.
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And it was something that he wrote and created and crafted along the way.
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and he I think he and Glenn Keane shared the Oscar for it because obviously Glen Keane's the animator that did the work.
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But it's it's incredible I for me it's it's such an amazing story about basically just taking something that you know taking something from one format writing and turning into another.
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That's one piece of inspiration.
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The other is as a basketball player you could imagine like the looks that he's getting when he's working on something like this.
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Like imagine talking to your like closest friends or your agent about calling Glenn Keen to like ask him to animate a short film with you.
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Like people would be like, "Dude, just go sell Gatorade and make like a billion dollars." Right?
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I had the very distinct advantage of you sent me some of your notes so I got to read all these things before and there's a line where he says, you know, I'm out.
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I'm on the road with my team members and they're like, "Hey, why why don't you come out with us?"
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He's like, "I'm not going to go out.
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I got to work on my writing.
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I got to study Joseph Campbell."
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And people are just like, "Dude, what are you what are you doing?"
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>> The other part of it that's inspiring to me was when I was in the middle of the pandemic, I was working on a book.
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And I just remember thinking if Kobe Bryant was working on this book, he would be working like five times harder.
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Like it it actually set a standard for what someone how someone should work because what he did was he just took the the discipline that he had for basketball and applied it to writing.
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And that in that's like that's unbelievable to me.
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It is the most inspiring thing to think about.
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He just took his schedule.
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He described his schedule at one point and somebody asked him after he retired, "What do you do every day?" Right?
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And there were all these like like athletes that go through intense depression.
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They don't know how to like they don't know what to do, where to go.
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They've had a schedule, a routinized life for 20 years or 10 years or 5 years. >> Yeah.
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>> He said, "I get up, I drop," he's like, "It's the same schedule.
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I get up, I work out, I drop my kids off at school, I go to the office, and I write for eight or nine hours, right?"
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and he goes and then I come home and it was the same and it was the same schedule that he has an had as an athlete.
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And so it was super inspiring to me because I was like well this isn't somebody that was born with genius or became a writer when they were 12 like everybody identified that they were a talent.
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He just worked at it and worked at it and worked at it and worked at it over decades while becoming one of the best basketball players of all time.
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If he can do that if he can do that I can I can definitely get up and work a little bit harder on my books. Right.
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The thing that struck me was he was asked what is hard about writing?
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Like what do you get out of basketball that you don't get in writing?
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And he said it's the feedback, the energy.
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You know, in basketball, if you make a shot, the crowd goes wild, >> whatever it is.
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And he said, when you write, part of the thing that you miss is the look on someone's face when they read it for the first time.
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He was like, "I wish I could just be in the car with the kids when they watch a movie that I make for the first time."
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And it bummed him out that he couldn't couldn't really do that. Yeah.
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There were some moments where he did get feedback and it you could just tell what it did for him.
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Like the the truth is that I actually think someone said someone asked him once and I think he answered that he loved storytelling just as much as he loved basketball, right?
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That actually it was a passion with equal force.
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And I just remember thinking like, my god, like that's incredible.
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Like you, you know, to to be able to even speak in those terms as a pro player, like he was he wasn't using the language that most pro players use when they talk about something they're interested in, right?
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There's this great interview I found where the the the person actually asks him, "So Kobe, are you going to would you want to come do TV?
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I mean, you could be like Charles Barkley."
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And he actually gets like almost uncomfortable.
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like he he cracks a joke at the end says I'll do the contract if you give me 60% of the royalties or revenue or whatever.
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But but at the beginning he's like no that's not what I'm going to do.
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He's like that's what they that's what they do right become a storyteller and I'm going to go find stories around the world and then craft them and work on them and release them.
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He actually was so passionate about storytelling that when he took his book ideas to publishers, what they would do is they would sort of put him in the cookie cutter like, "Well, you're a successful celebrity athlete.
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You have a big following.
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Here's how we do the book."
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And he actually rejected like book deals.
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He decided to create his own publishing company because they weren't going to invest in the quality of the books that he wanted to do. So, here's an example.
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He talks in this one interview, and by the way, this is like, so just to to give people a window into this, this is like I'm on year three and a half or four of diving into every Kobe interview there is.
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So these are not the interviews that are like the famous press conference interviews after the like 81 point game.
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I'm watching the ones that he did on like Chinese television that are 12 minutes that have like a thousand YouTube views, right?
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Um, but what I found was that he actually spent two weeks with his team rearchitecting the barcode on one of his books because he wanted the barcode to more fluidly and elegantly blend into the backdrop of the book.
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And no publisher was going to spend two weeks and huge amounts of resources to rearchitect a a you know a barcode.
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And so there was at every part of it he was like well what's what's the highest quality thing we could do?
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Publishers were giving him insufficient answers.
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So he designed his own publishing company so the books could be better.
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And it's like it's incredible.
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I mean that's like an incredible level of commitment at betting on yourself when you have big publishing houses saying, "Yeah, you're Kobe Bryant. We will work with you."
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And he's like, "You're not going to do it to my level." Like it blew my mind.
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I mean, that that is like true love of craft right there.
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Um, and he even talked, you know, at every at every stage of the craft, he talked about the importance of outlining, how he how obsessed he was with getting the perfect word on the page, like find like really obsessing over sentences and paragraphs and structure, making sure that things were relevant to readers.
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You know, he had daughters, so he talked a lot about how sports heroes like he had never seen a sports fantasy novel.
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That was what he wanted to do.
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And he's like, "Yeah, but it has to be it has to be like female leads because I I have I'm the daughter of all girls.
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Like, you know, I've got to find a way to inspire them."
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And so he was he was reinventing the craft even as he was learning it, which I also really respected and admired.
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And so that's kind of this this hidden part of his life that to me to you and I to people like you and I, it's it's an approach to craft that is about discipline and about stickuitiveness and just about like actually loving the thing itself.
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He loved the thing itself. >> Yeah.
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The other thing that stuck out with Dear Basketball is a lot of people said, "It's not going to work. Basketball's too niche.
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You know, there's not a lot of people who who play the game.
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There's it's just not going to be enough, man."
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And what ended up happening, and I forget the exact details, but what happened was they said, "No, a lot of people can relate to your obsession with basketball, and they'll be obsessed with something like that in their life."
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And Kobe, when I was reading your notes, I saw that Kobe would think a lot about the introspection of the emotions that you're going through.
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you're going through. like you know people are different but if you go to Italy if you go to China human emotions love loss grief dreams hopes whatever it is they're the same and if you can really do the introspection and get to the core of your emotion then
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whatever it is no matter how niche that thing you produces whether it's basketball or painting or whatever it's really going to resonate because those core emotions are so timeless and so As I was looking at your notes, I was like, "Whoa, he is thinking at that level." >> Yep. >> Yep.
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>> Well, and and the thing is is that it's it's like anything.
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It what what struck me about his life and some of his research and some of the people that he was in touch with is that he would look for people who felt that exact same feeling you just described.
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So, he went to George RR Martin because George R.
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Martin feels the same way about his work that Kobe felt about basketball.
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He would talk to Johnny IV because Johnny Ive felt the same way about product design that Kobe felt about basketball.
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He would look for like these luminaries in every field, not because they were successful or famous, but because they were so obsessed with every detail, so obsessed at getting it right.
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He he actually did this long riff on uh on a podcast where he was talking about Taylor Swift.
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And you would think like, okay, girl, dad, like, look, I I have been to I've been to the store twice.
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I'm a devoued Taylor Swift fan.
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Huge Swifty in in part because I have a daughter and it was a huge bonding thing for us, but also I think she's incredible, right?
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the the thing that and you'd expect him to kind of say the same thing.
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What he said was really different.
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He said, "The reason that I I wanted to get to know her is not just because my daughters enjoy the music and I enjoy the music.
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The reason is because it is I wanted to understand how someone could be at that level of their craft for as long as she has been at that level of their craft."
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So, he was thinking about longevity.
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He would go and find these people and I think what he found is probably what you and I have found which is at base there has to be an impulse that's love.
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It has to be about love because everything else actually falls apart, right?
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Ambition, it's a fuel that burns relatively clean for a while and then it can it can not burn so clean.
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Revenge probably doesn't burn very clean, right?
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So, I think it it can, you know, you can find the fuel that you need.
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And granted, by the way, great writing has often come out of those impulses, too.
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But the true greats, I think it has to come from love.
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It's the only sustaining force there is.
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So he would go and he would I remember reading that he like he actually would go and find somebody in a totally unrelated field and just go to school on them.
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He said that he read, watched or saw everything that Bruce Lee had ever done.
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Every single word syllable uttered by Bruce Lee.
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And then the obsession went to the next level.
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He decided to study Jeet Kundo, the the martial art that that Bruce Lee like really, you know, uh made a mainstream phenomenon.
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He decided to study it so he could get inside his head even more. Right?
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And so I I think of this as like somebody who was looking for other people who love that fiercely.
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Like Kobe was on a search for people who love something as much as he loved basketball.
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He describes in one of the the interviews I watched that at the that he was obsessed with the smell of the basketball.
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He loved it so much he would smell basketballs because he loved it.
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He loved the he loved the sound of a basketball and he knew he could tell by the sound what kind of floor it was hitting, right?
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because he had just like obsessed over the sounds, right?
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That kind of thing I think does not come from I really need to make sure I hit 35 points a game, right?
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Like like yes, there's a part of it that is achievement and and ambition and competition, but he truly loved the game and then he went looking for people who just like loved anything as much as he loved the game.
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Um he had this great line that I always think about actually always makes me think about you because this is like your friendship and my friendship is born of this kind of obsession, right?
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Yeah, we there's no there's no accident that we connected.
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We're obsessed with many of the same things. >> He has this line.
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Somebody asks him, Kobe, do you have do you have friends >> and he pauses and it was in an interview in GQ >> and it roughly says he roughly answers the question. He says not really.
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He said, "What I have are fellow obsessives."
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He says, "So I'm grateful that I live in LA because in LA there are people who love what they do as much as I love what I do."
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And he goes on and he says, "Am I the friend who's always going to remember your birthday or like be at every event?" No.
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But I am the person that when I get together with you, we can go full nerd on our thing and really learn from each other's craft, right?
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And I remember thinking like my best friendships are often the people I see the least, but when we're together, there's an energy that you can't match, right?
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And that is to me the sort of essence of who he was.
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It's the essence of the people that you and I study and admire.
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They look for that in other people and then they go and just like chase it down.
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I want to talk about your obsession, your craft because you are basically the most you're one of the most obsessed writers that I know personally.
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>> The only person I can think who's maybe more obsessive than you is Robert Caro, which is like if you're in that league, you're doing something right.
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So, I want to just talk about like any given Tuesday, like what is a day in the life of you and then we'll go from there.
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Yeah, I can I mean I can tell you even any given, you know, dayto day, like any given Wednesday today, um I get up and I I start almost every day the same way, which is I go straight into the writing project.
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There's no no mus, no fuss.
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I get up, lights on, dive right into the work.
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Um there are a few reasons for this.
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One is it's a system that at this point has worked for me over many many years, right? Like it just works.
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The other is there is no one bothering you at 4 o'clock in the morning, right?
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Like honestly, you're >> up at 4 a. m. >> Yeah. 4 a. m.
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Because the thing is is that the world like the world is a conspiracy designed to prevent writing from happening.
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Like actually much of the world is designed to just screw with my my head, my time, my energy, right?
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It's like literally I see I can sort of I see myself as like a in a contest against the world a lot of the time to just protect and preserve three to four hours a day where I can write.
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And people get this all different ways.
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There are some people that need to move to a cabin in the woods.
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I don't have that luxury.
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I have a I have a daughter.
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She goes to school in Brooklyn. She lives a normal life.
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So, for me to live the abnormal part of my life, it has to happen from basically 4:00 a. m.
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to around, let's say, 8 or 9:00 a. m. every day.
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And during those hours, I'm working on whatever the most important writing project is that I'm working on. It is not email.
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It is not like the sort of administrative stuff, the TDM, making sure the kitchen's clean, all of that. I just go straight in.
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Dude, I'm gonna be starting my days at nine in the morning, grogg as hell, drinking my first espresso of the day, diving into work, and I'm gonna start thinking Jimmy has already done all of his writing for the day.
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Do you know how humiliating that is?
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>> It's not humiliating because your day might your day people people can find that time whenever they find that time.
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The point is the point is not the early rising because it's not like some weird aggro, you know, badge of pride thing. It's it's really basic.
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It's actually super basic in a way, which is like writing for me is a tough thing to do.
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And in order to do it well, I need to have time where other people don't bother me, where the world doesn't interfere, where I don't feel the pull of the inbox.
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And the truth is, the hours of 4 to 8:00 a. m. or 4 to 9:00 a. m.
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or sometimes 4 to 10 are ideal because nobody is bothering me.
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And because like even when I'm with my daughter, I can eek out 4 to let's say seven when she wakes up and then I get time with her where I don't feel like I'm like in parent guilt mode, right?
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You're not robbing Peter to pay Paul, right?
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But the the point is that those hours are really protected.
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And I would say that actually a lot of the creatives I know, they have to shift their schedules this way because after a certain hour, at least for me, it just doesn't nothing functions anymore. I need to turn it off.
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But that's like a big part of the 4 a. m. thing.
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Other piece of it is um if I get that work done first and I do it seven days a week, there is no possibility that a book won't get done.
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I don't know if the book will be good, right?
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That's a that's a separate conversation, but there's no chance that something doesn't get done if seven days a week you're doing the most important thing from 4:00 a. m. to 9:00 a. m. , right?
23:25
It's really like it's it's just a ma it is just math.
23:29
It's like if you have three to five hours a day that you devote to a thing, you're just going to finish it and then you can go on about the rest of your day.
23:36
And so you just stack enough of those days together.
23:38
This isn't again any kind of big breakthrough insight.
23:41
It's just the process that works for me.
23:43
There is a there's one other thing which is I try to give my best mental energy to the thing that's most important.
23:47
And for me, my best mental energy is like the first hours of the day.
23:51
If I if I frontloaded, let's say, other work and then I went to the books later, I'd kind of be giving it like like I'd be giving it like um like regular fuel instead of premium, right?
24:03
Like it wouldn't be the premium fuel.
24:05
The premium fuel is reserved for the morning and that's reserved for, you know, whatever the book project is.
24:08
So, for example, this morning you and I are going to record. I've been up since 4:00.
24:11
I was working on Kobe this morning.
24:13
>> I know you texted me at 5:16 this morning like, "Yo, I'm ready to go." >> Yeah.
24:17
>> And I I was up working on Kobe.
24:17
the there's also a part of this, you know, Jerry Seinfeld talks about not breaking the chain, like his calendar of hitting every day.
24:24
I do think >> Have you ever seen the photo of him in New York with all the yellow legal pads? >> No.
24:31
>> He would always write on a yellow legal pad and there's an entire street in New York and the whole cement is just covered with yellow legal pads that he had written on over the course of his career.
24:44
And when you talk about like the creative residue that comes, the obsession, the level of dedication, that photo. >> Yeah.
24:52
And and and the truth is that that's like a big for me a big part of it is if I do it seven days a week as opposed to five, you just here here's here's the feeling. All right.
25:01
So, I had this feeling like a a week or two ago.
25:05
Um I was on I was on vacation.
25:05
I was happy to be there, but it did not I did not have like the the time or the kind of structure to do book work at that moment.
25:15
>> And again, I was happy to be there.
25:15
Um, but I I realized I felt off like throughout the day, I actually like I could feel it in my body chemistry.
25:23
I was like, I didn't do the I didn't do the thing.
25:27
And I like knew right away.
25:27
I was like, something feels off.
25:29
Like it does not feel like a normal day.
25:31
And so I can at this point it's become such a habit that I can feel it when I don't do It's like breathing.
25:36
Like it's like I can really feel it.
25:38
And the the nice thing is when that becomes your default, this isn't work anymore, right? It's not work.
25:46
I don't wake up and I'm like, "Oh god, I got to work got to work on Kobe again.
25:49
Gez, like what am I going to do?" It's not the salt mines.
25:51
I'm not like packing a lunch pail and going to some place I don't want to go.
25:53
I'm waking up every day and doing the thing that I'm most passionate in the world about.
25:56
And because I've just gotten so accustomed to doing it, I protect that time.
25:59
So I go to bed super early.
26:02
like I like, you know, don't it's like these there's a lot of people think that the writing life is like this life of like like fancy cocktail parties in Manhattan or whatever and it's really like for a lot of the writers I know it's much more boring.
26:13
You go to bed early, you wake up early, you get your work done and that is the most exciting time there is in the day for me.
26:18
The other thing I want to talk about is the sheer diversity of writing that you've done.
26:23
I want to talk about the stuff that you're working on now, but you've done political speech writing, you've done opeds, you've done ghost writing, you've done books, you've done a whole book about a carousel in in in Brooklyn.
26:34
So many different kinds of writing. >> Right. Right. Right.
26:37
The the the the less charitable way of doing that would be like the Winston Churchill line when he when he was describing something he was criticizing, he was like, "This pudding has no theme." Right.
26:45
It's kind of how I feel about myself sometimes.
26:48
But, you know, I there's a few reasons for that.
26:50
One is, you know, careers in writing are rarely like a single track thing.
26:54
You don't, you know, it's it's it's hard if you don't know what this industry is all about.
26:58
Writing broadly defined can mean anything, right?
27:00
It can mean copywriting for ads.
27:01
It can mean doing novels.
27:03
And so, you sort of find your way, right?
27:05
And I kind of found my way in different domains.
27:07
Speechw writing, op-ed writing, ghost writing, like all sorts of different things, essay writing, and then books.
27:12
And for me often it was just I had something that I wanted to say and there was a format that was going to work well for it so I said it or it was just like it was work.
27:23
It was like I was being paid to do it and you just get better.
27:24
I I would say that there's a lot of value in thinking of different types of writing as crossraining for your core habit.
27:32
So if we go back to an analogy you and I have used before about training like an athlete.
27:37
Y like if you're a soccer player you might do yoga, right?
27:40
I'm a bookw writer who also writes opeds.
27:45
Opeds help me become a better bookw writer.
27:46
And by the way, writing books helps me become a better op-ed writer. It's cross trainining.
27:50
It is the way I think about it.
27:51
I'm stretching different muscles.
27:53
Opeds are typically 700 words.
27:55
That is not a lot to make an important point.
27:58
And so you have to really compress.
28:00
Where else does like word economy help?
28:02
Oh, in every other kind of writing you do.
28:05
Literally every other kind of writing, right?
28:06
Like like people are like, "Oh, you know, social media is terrible for writing."
28:10
And I'm like, actually, I think Twitter improved a whole generation of writers because it forced them into at the time 180 characters, then 240, and now a little longer, right?
28:18
But word economy is important in any format, and I learned it through op-ed writing.
28:22
I learned how to take words out of sentences, rearrange things so they're a little shorter.
28:26
That skill came through a totally different format.
28:29
So, I like having different formats.
28:31
I think it there are some novelists and other people I know and non-fiction writers where the only thing they can work on is one project at a time.
28:37
I have one core project, but I actually really like having to like get my brain into a different mode of writing and then come back to my core project after.
28:46
H tell me about research.
28:49
How does research factor into all this?
28:50
Because whenever I feel like I need to do research, I often use it as excuse for procrastination.
28:55
Oh, you know, I got to do research and then you kind of end up in rabbit holes.
29:00
And then the other thing I find that's a very specific thing but I find that I sometimes overindex on the things that I just learned when I'm doing research >> and how does that factor into your writing process?
29:16
Is that something that you do in the morning or is that like afternoon work?
29:19
Yeah, this is a great question and it's it's evolved over time >> because what I have discovered is that for myself >> and I I think for a decent number of people research is an excuse not to write. >> Yeah. >> Right. Exactly.
29:33
It is it is basically like look nobody nobody maybe except you loves a Wikipedia rabbit hole more than I do. Right.
29:40
Like no like it's like I just love them. Right.
29:41
It's like I I could spend hours just like researching random things, right?
29:45
But it's often an excuse for putting aside the work that I actually need to do.
29:50
So over time, I realized this about myself.
29:53
I was like, look, like, bro, you're just using your research time as a way of getting out of the anxious feeling that you feel when you have to put pen to paper and actually say stuff because it might embarrass you because it's said badly, right?
30:07
You've got some anxiety around this project and you don't think it's going to work.
30:11
So, what are you going to do?
30:12
You're going to convince yourself you're doing fake work by doing research, right?
30:14
So what I decided to do was I was like, well, I just need to like build this into the system.
30:17
So what I typically do is I structure my morning to get really really tactical and really specific.
30:25
So I have I I kind of realized I was like, look, if you if you wake up, fire up an open page, and just start to write, you're going to be scared out of your wits. It's really hard.
30:35
It's hard to you got to get the at least for me, I have to get the engine warm a little bit.
30:39
So I have like what I like to think of as like on-ramps.
30:41
So, one of my on-ramps is um whatever the the model book is for a book I'm writing, like a book I really admire where I'm trying to basically like do whatever that author is doing.
30:52
>> Wait, that's an interesting thing.
30:52
So, that's You have model books. >> I model books. All right.
30:55
Quick digression, then we'll get back to the the schedule. The degression of that.
30:59
One of the the best pieces of advice I got was just to take a book that basically is like the cast, like the plaster cast for your idea and study it obsessively.
31:08
And I mean really obsessively.
31:11
So, for the founders, it was The Everything Store by Brad Stone, which I think I've talked to you about before.
31:16
I read that book over 20 times.
31:19
Like, I will read the model book for a particular book I'm writing dozens of times if need be.
31:23
Part of how I do that is I spend the first 10 or 15 minutes of that time at 4:00 a. m.
31:28
reading the model book because it what it does, it sort of like tricks my brain into thinking like, "Oh, oh, you don't you're not doing anything right now.
31:36
All you're doing is reading to me. You love reading.
31:38
This is going to be so much fun.
31:39
like let's let's get just get on this on-ramp, right?
31:42
And the on-ramp is reading.
31:42
So, for example, I think and you know, Eric will be delighted to hear this because the book is phenomenal, but I've read the almanac of Naval Ravocant probably nine times already, right? All the way through.
31:53
And I'm taking notes and I'm dissecting things and I'm seeing how he made certain sections work and seeing why certain formatting things work and why other things didn't work and why is this sentence longer than this sentence and how did he do this?
32:02
I'm but that's the first 10 or 15 minutes and it's my little on-ramp but it also is teaching me why that book worked as well as it did. Right?
32:10
So once the on-ramp is done, what I typically do then is I'm like, "All right, let's do like a little bit of research."
32:15
So I set a timer and I'll do like I'll give myself 30 minutes, right, of like let's read some notes or like watch a video or like study some thing that I found or reread an interview or reread a book. 30 minutes of research.
32:26
Then I get into writing and then what I do is I just set a word count.
32:31
And so if I hit my word count every day, it's been a good day.
32:33
And like that's that's really a lot of the process is just very like brass tax battling your own psychology to get the on-ramp, then do a little bit of research and then get into the writing.
32:45
And what I try to do is obviously you have to calibrate some of this.
32:47
Like if I'm preparing for an interview, I have to dial up the research a little bit.
32:51
>> So that's an interview where you're interviewing like a source. Okay, got it.
32:55
But the the point remains you if you do if you spend the entire morning researching, you didn't do any writing.
33:01
But then I'm trying to figure out how this squares with the PayPal book or something like that, which is phenomenally researched. Yep.
33:11
>> So you're not doing that in 30 minutes a day. There's no way. >> Not 30 minutes a day.
33:13
30 minutes a day is my call it my like kind of candy excuse like before I start writing and then I'm I'm getting into the writing because you if you if you're too slow a lot of the research I would say happens as a blend of research and writing.
33:24
So if I'm in the middle of a section and I need to make a point I will just go dig up the fact I need and put it in the thing that I'm writing.
33:32
But that's is that research? Yeah. Is it writing? Yeah.
33:37
If they happen at the same time I'm not letting myself off the hook.
33:40
I'm actually doing them at the same time.
33:44
And it's far more productive.
33:44
People can spend people have spent decades researching books they never write.
33:47
I actually know somebody who has spent like two decades working on a book about Plato and he hasn't written it yet. It's not done. Right?
33:54
And like it's very easy to fall into this trap and it's very it can be because it's there's an anxiety around around creating new new material.
34:03
People want to talk about it.
34:03
They want to medicate it.
34:04
They want to run away from it.
34:06
At base it is there like writer's block can be real.
34:09
So you have to battle it.
34:10
And the way I battle is by blending writing and research.
34:12
Here's another here's another thing that I've done.
34:15
I turn all time that is quote unquote free time into research time. Here's how.
34:22
If I need to walk to go do groceries, I will listen to a podcast or an interview about the thing that I am writing.
34:29
In the evenings when I was doing PayPal, I was watching YouTube videos that were just interviews of the people I was writing about. So, it was research.
34:37
like it was research but it was also like like the time when somebody else might be watching Netflix I was watching like interviews with Peter Teal like like welcome to my life right but like but that was a useful way then of me having the time to do research so that the quantity of research was huge.
34:51
I would also say there are there are moments when you do need to spend like an afternoon really diving into some topic.
34:56
But honestly, honestly, you can typically set a limit on your research, start the writing, and then go back to the research cuz the research is the fun stuff. That's the discovery. That's the hunt. That's the game.
35:09
That's the like that's just like googling and it's reading and it's printing things out.
35:13
It's like when you it it's so fun that I don't even need to schedule it.
35:18
What I need to schedule is the creation of the thing itself. >> Right.
35:23
>> Can you tell the Ed Boa story? >> Yeah.
35:24
I feel like it's kind of like asking uh the Eagles to play Hotel California.
35:28
But could you just tell that story? It's so good.
35:30
Cuz I think the reason why is I think this is such a good example of what happens when research goes well. Yeah.
35:40
>> Is you find an alternative source, you tell a story that's super memorable and then also speaks to something that is core to the theme of what you're sharing.
35:50
And then you get, you know, some lunatic like me and I think about the story all the time, >> right?
35:55
So yeah, just for for context for people.
35:57
So this is a story that emerges from my research for the the founders book.
36:01
And that book, you know, it took six years.
36:03
Like it was a it was a really intense project. There was a ton.
36:05
I mean, I wrote double the quantity of words.
36:09
I wrote about 320 350,000 words for a book that ended up being about 140,000.
36:15
So I cut a lot of stuff, right?
36:18
a lot of stuff and I did lots of interviews.
36:21
I mean a lot of interviews and there there was this amazing thing that happened when I found somebody had shared a term sheet for one of the early companies that would become PayPal.
36:32
And it had not a term sheet, sorry, a cap table where it had listed the investors who had invested in PayPal.
36:39
And some of the names I I recognized, you know, it would like they were familiar names from my research.
36:45
And kind of toward the bottom there was this name of this guy, Ed Bogus.
36:49
And I was like, who is this?
36:49
I was like, this I've never seen this name before.
36:53
He's not some famous Silicon Valley investor.
36:54
He's not a technology person.
36:56
So I start I was like, but he invested very early in Peter Teal's company. It was called Infinity. I like what could why?
37:03
So I Google and I type in his name and I find out that he's like a musician living in San Francisco.
37:10
And I'm like, what the he this now it's even more perplexing.
37:12
I'm like, did I get the wrong Ed Bogus? is like an Ed Bogus Jr. , right? What is going on here?
37:18
So, I do one of those searches where you can just look up somebody's name and then they'll find like a few phone numbers that might be their phone number.
37:24
And I kind of screenshotted all those.
37:25
And I was like, I got to track this guy down and see if he's the right guy.
37:29
So, I I was like, what what other option do I have?
37:31
I call the number, right?
37:33
650 something something something.
37:34
Call the number and I'm like, hi, Ed.
37:37
Um, I'm not sure if you're the right Ed Bogus. My name is Jimmy Sony.
37:41
I'm working on a book about the origin story of PayPal.
37:42
And there's this um there's this document I have where it says you're one of the earliest investors.
37:48
I have no idea if this is you, but if it is, if you wouldn't mind giving me a call back, I'd love to talk to you about what led you to do the investment, blah blah blah blah blah.
37:55
And this is a this is like total Hail Mary, right?
37:57
I'm not actually expecting a call back.
37:58
So, I finish the phone call, leave the message, and within like 10 or 15 minutes, I get a call back from this guy.
38:05
And he and I didn't expect it.
38:08
So, I'm like a little I'm like a little caught unawares. I'm not like ready.
38:09
And so he calls me and he goes he's like, "Hi Jimmy.
38:13
Um yeah, you've reached the right ed.
38:15
I was actually an investor in like an early iteration of this company and uh like happy to chat about it." So I like had him right.
38:23
I had the fish on the line.
38:24
I've got to like do this now.
38:26
So I like dive in and I'm like, "Well, listen, like how did you find your way to this company?
38:30
You're not an angel investor of any renown."
38:32
Like he and he sort of cut me out.
38:35
He's like, "Yeah, this is like the only real investment I've ever made." Or something like that.
38:38
Like it's the only serious investment I made.
38:40
And it turns out he tells me this story which is the most amazing story.
38:45
He said what happened is that while Peter was building companies and investing in companies and kind of familiarizing himself with the technological landscape in and around PaloAlto, he was also playing competitive chess because he was an exceptional chess player.
38:56
So he and Ed would square off at chess tournaments because Ed was also a chess player.
39:01
They would face off against each other and he met Peter and played him and he described his style of play as merciless.
39:10
So one day Peter Thiel shows up at Ed Bogus' house.
39:13
He is looking for friends and family investment for his company.
39:18
And he knows Ed and he says, "Hey Ed, I don't, you know, I don't know if you'd want to invest.
39:21
I know you and I have had some good chess competitions or chess matches.
39:24
Would you want to would you want to, you know, participate in this in this thing?"
39:27
And so Ed stops him, goes to the back, grabs a check, writes the check on the spot, gives gives Peter the money.
39:34
And so naturally, as an interviewer, I'm thinking to myself, like, wait, hold on.
39:37
Like, why would you do that?
39:40
Like, why would you like that's money and you're just giving it to this guy you played chess with?
39:46
And he said, Peter was so ruthless, so merciless in his style of play that I knew that anything that he did, he would make it successful.
39:53
And and that's why he did it.
39:55
and he said, "And it was one of the best investments I've ever made in my life because I got in early on this company that became PayPal."
40:00
And it was just such an amazing thing to me because it for me it was really validating on a couple of one was just like it does just pay to run to ground every little thread of a story that you're looking for because you never know when a story is actually going to lead you to something that no the world had never known that anecdote.
40:20
Ed Bogus had probably forgotten all about Confinity and PayPal and his investment and everything, right?
40:26
But for me, the story spoke volumes about Peter.
40:28
It spoke volumes about that era, about how people can intersect and interact. It was amazing.
40:36
And it was one of these things that like I my friends would jokingly, they would joke about my obsession with PayPal.
40:40
They would actually like give me grief for it, but I was like, "Got you guys.
40:43
This is why this is why I'm as obsessed as I am."
40:46
There's another thing about the story which is that sometimes the best anecdotes come from the people on the periphery. That's right.
40:51
And not from the people in the middle, you know, and you this sort of like what you were saying with Kobe early, right?
40:55
Everyone knows the press conference after he scores 81 points.
41:00
There are certain things in the Kobe story that are just part of the cannon.
41:05
But then there's other interviews that have 634 >> y >> views on YouTube. Yeah.
41:11
And sometimes those are the things that lead you to the real nuggets. >> That's right.
41:18
One of my favorite writers, Michael Lewis, I heard him describe this once and it always stuck with me.
41:22
He was describing, he was an art history major at Princeton and he described this thing, I guess, that happens in Renaissance paintings because a lot of Renaissance paintings like basically look the same, right?
41:31
They're all like they're all like depictions of religious scenes.
41:33
He said, "If you want to find the intricacies, look at the toenails."
41:37
So the toenails, look at the toenails of the figures that are being drawn because it's where the artist would often like like basically lose steam or have their most like that's where they didn't have to depict everything the same way everybody else did, right?
41:50
So he's like if you look at the edges, those toenails, you'll actually see some very distinctive designs.
41:54
By the way, I don't know if this is true or not.
41:56
You might might be wrong, but the image always stuck with me because I would I always ask myself, what did everybody else looking at this miss?
42:03
Or what question didn't they ask? Right?
42:06
I'll give you an example for as a part of the founders book.
42:08
I was interviewing Elon and it was my like third interviewer interaction with him, maybe second, maybe third.
42:15
And I knew I wasn't going to have more.
42:17
There was no reason to have more.
42:18
I was almost done with the book.
42:20
I'd gotten from him everything I needed for his part of the story.
42:22
So then I said to myself, like what would be the question that I'd want to ask him that other people have not asked him about?
42:27
asked him about? and he had had a a close friend of his who was an early um investor in and adviser to his first company, Zip 2, this guy Greg Corey and and I and he was a close friend and he died at a very young age and in my head I was thinking look if I were in my 20s
42:46
or 30s and I had a young close friend of mine who built a company with me die that would leave an enormous imprint in my life in my makeup in everything right um I don't know if you have a vivid experience of death I I fortunately Not, but everybody I know that has been through that kind of experience. It
43:00
It shapes everything that happens after like like grief casts a shadow that never leaves you.
43:08
>> So I thought to myself like what if I started my interview with him by asking about Greg Corey >> and that's what I did and I remember I said Elon I want to begin our interview a little bit differently.
43:17
a little bit differently. I had read about this gentleman that had helped you early on in your life when you were trying to make it in technology and I found his widow and we talked and his name is Greg Corey and I wonder like like what he was to you or like what he
43:29
represents to you was he you know how can you talk about him and there's a pause and he goes oh my god and he like actually had this incredible response and he was like he gave me this like minutelong meditation on Greg and their friendship and everything that it meant to him. I don't think anybody's talking
43:43
I don't think anybody's talking to him about Greg Corey because because he's ultimately the people who are interviewing him or talking to him are dealing with much more day-to-day concerns.
43:51
But I always try to ask myself and remind myself like these the human beings that I interview or the projects that I'm working on, they have lives that exist outside of the very narrow frame of reference that we see them for.
44:03
So what's the thing that like they never get talked about or asked about that you can like kind of find a way in and it actually reveals something about their character, right?
44:11
Like I find for example like like if you if you're talking to like um a successful let's say I don't know a successful business person like they have a family life they went to college they you know like they they have lives outside of these little domains that we're in.
44:28
If you ask them about that you'll often learn more about the core thing.
44:32
And I have found this to work enough that it it is a technique that I like using also because it makes things just easier and more personal and more interesting.
44:42
And so that that sort of call it the toenail strategy is a part of what I try to do.
44:46
So like I like sure could I interview all the other important names on the cap table? Yes. And I did.
44:51
But Ed Bogus has a hell of a story to tell.
44:54
You just have to find him.
44:56
And that's the that's the fun. The fun is finding him. >> Yeah.
44:59
You were talking about Michael Lewis.
45:00
We talked about the model books.
45:02
But I want to talk about sort of like a hall of heroes that you have.
45:05
>> Who's on that hall of heroes?
45:05
Like who do you really look up to?
45:07
Who do you want to emulate?
45:08
Who are these masters of craft that you really admire? >> Yeah.
45:13
I would say for me a big one is someone you mentioned earlier, Robert Carrow.
45:16
So I mean talk about like you know the Kobe of non-fiction biography, you know, like like there's nobody that does it the way he does it.
45:24
All of us, I think, are actually just secretly in in my particular domain are all just trying to become Robert Caro. Like it really is.
45:31
It's like it's like we're just we're just trying to do that, right? He is that good.
45:35
Somebody who spends 10 years on a book.
45:37
Somebody who moves to Texas Hill Country so he can describe it better, right?
45:40
Like and lives that like somebody who runs from his apartment in Washington DC to cap to the capital so he can see the light on the Capitol dome the same way that Lyndon Johnson saw it in the morning sun.
45:52
>> A morning like unbelievable the level of dedication and commitment and everything else.
45:57
and and I look at him and I'm like, well, if he can do that, what's my version of that? Right?
46:02
So, I'll give you like an example is I remember when I was when I was writing the founders, I knew the street that the offices were on.
46:10
So, I actually would go this in Palo Alto. >> This is in Palo Alto.
46:13
So, I actually chose different times when I would walk the street just to get a sense for like what it would look like or feel like when I was doing it.
46:20
And I didn't end up including those observations in the book, but also having a sense for how boring PaloAlto is.
46:25
and how uninspiring those blocks are really important to know because it's no Manhattan.
46:31
Palo Alto is not an inspiring place and yet all of these things have happened within like a 5 mile radius of Stanford's campus.
46:41
You're like and >> what there's something to that that you need to know. Totally.
46:45
And my friend calls it method writing.
46:47
She's like you're a method writer.
46:48
You like need to inhabit your subject's world as entirely as you can.
46:52
And I think of Robert Caro as basically the dean of that.
46:54
the guy, you know, to spend as long as he did with the kinds of projects that he was taking on, which are hugely risky projects.
47:01
By the way, there was no guarantee that Power Broker was going to work, there was no guarantee that any of even today, if you were to say the name Robert Moses, most people outside of like you and I and our friends don't don't actually know who that is, right?
47:12
And so to take on the risk, the level of risk that he took creatively and then to do it at the level that he did and then by the way >> to turn history into art >> to make it a pleasure to read like oh my god the books the books like they they they they vibrate.
47:27
They have their own frequency.
47:29
You get into a book from Robert Caro and you're just enraptured the whole time.
47:33
You're just like I don't know how somebody could do sentences like this. This is amazing.
47:35
He turned history into literature.
47:37
He turned it into high art and it it's incredible.
47:38
So for me, if there's a Hall of Heroes and there's a Zeus in like the Mount Olympus of He's the Zeus.
47:44
He's just that good and that disciplined.
47:46
I also, by the way, really like that he he would like treat his work like a professional treats his work.
47:52
He would like put on a suit even though he didn't have to wear a suit.
47:56
He would sit at he go to an he work at a typewriter.
47:58
He had like a real process about his work and it was just every day and it was day after day after day after day.
48:04
And I think there's something to that and that's why his books will be monuments for the rest of time, right?
48:08
Um, and and to the doggedness is just something to be admired that you you can't look at a person like that and not find something to admire about them. How about Michael Lewis?
48:20
So, this is an interesting one because, you know, there's a lot of fans of his, right?
48:23
And so, I'm a fan obviously, but I actually have, this is, you know, I've watched every interview he's ever done, right?
48:29
Like I I went to school on Michael Lewis because he's so good, but he's otherworldly good, right?
48:36
Like I I actually think of him as like a talent I'll never get near because he grew up on New Orleans porches listening to people tell stories like in the south, you know?
48:43
So there's a quality, a musicality, a rhythm of those stories that is in his writing and it infuses his writing.
48:48
Here's why I see him as on my hall of heroes.
48:50
I, as you could probably tell already, don't want to be pigeonholed as an author.
48:55
If I want to do a book about carousels and then follow that book up with a book about the justice system and then follow that book up with a book about Kobe Bryant, I that's what I'm going to do.
49:04
I'm gonna do that >> a lot of You want to be able to do any kind of book? >> Any kind of book.
49:08
And I want to follow my curiosity wherever it's going to take me to whatever crazy extremes it takes me, right?
49:13
And my list of books I want to write, I mean, you would think I belong in an insane asylum.
49:16
Like, it's like it's all over the place, right?
49:19
Like, it's truly all over the place.
49:19
Um, so for for me, what I admire about Michael Lewis is he he could have followed up Liars Poker with probably like 10 more books about finance, right?
49:31
He would have been like he he could have done that.
49:33
He could have just rinsed and repeated the entire time and he hasn't.
49:36
He wrote a book about coaching.
49:36
He wrote a book about parenting.
49:38
He's written books about the friendship between like two Nobel laureates. He did the blind side. He did the big short.
49:44
He would say that the common denominator is markets and like kind of understanding weird distortions in markets.
49:49
But you have to have some level of like dexterity and creativity to say I'm doing a baseball book and then I'm not just going to do a baseball book.
49:58
I'm doing probably the best read baseball book of all time. Right.
50:02
And so that is one of the um one of the things that like I really admire is just his willingness to say the world wants me to do this.
50:12
I'm going to go and do this other thing.
50:15
Now, he's ridiculously good and super hardworking as best as I can tell and like approaches his craft with real seriousness and and real like a real flare for storytelling, but it still takes a huge amount of creative courage to say, "I've been doing this thing well and I have a lot of success.
50:31
I'm going to abandon all of that and go do something totally different."
50:36
>> Didn't you say wrote under a pen name or something?
50:38
>> Yeah, this is one of my favorite stories that nobody knows.
50:40
Again, that's also because nobody's going to watch every interview Michael.
50:44
So >> you're such a maniac. >> I know.
50:46
But but so when he was working at Solomon Brothers, um he wanted to write op-eds and so he wrote an op-ed in the Wall Street Journal.
50:55
Big day in his life, but the op-ed basically made the argument that bankers were overpaid.
50:59
He works at Solomon Brothers.
51:01
So the I guess the the like leadership at Solomon Brothers was like, you can't keep writing opeds.
51:06
Like you this is not going to happen.
51:08
And he basically told them like, I'm going to keep writing opeds, but what if I did it under the name Diana Bleecker, my mother's maiden name?
51:16
So for years, Diana Bleecker was doing commentary about Wall Street, and people did not know that it was Michael Lewis.
51:23
And he got his first book deal because the publisher called around trying to figure out who Diana Bleecker is and managed to find their way to Michael Lewis.
51:31
And so he was writing under a pen name for years because he he wanted to keep writing about Wall Street, but his bosses at Wall Street said, "You can't do it."
51:37
And so that's what he was doing.
51:39
And I find that story super inspiring.
51:40
Like it would have been so much easier for him to just hang it up and be like, "All right, cool. I get it. I got to stand down." But he just kept going.
51:46
And to me, that's like that's that's the craft.
51:49
That's love of craft at its purest form.
51:51
I'm going to do it even if it's my mom's name on the OpEd. I mean, come on. That's incredible. >> Yeah.
51:56
What makes you so excited about what's happening with AI?
52:00
And before we get into this, I just want to establish something for our fellow listeners, which is there's something >> that a lot of people feel that AI is for people AI and writing is for people who don't take craft seriously.
52:13
And you'll notice that in the way that I structured this conversation, I really wanted to establish that Jimmy takes craft seriously.
52:21
And so whether you are pro AI or anti-AI, all power to you. Uh that's fine.
52:27
But I really want to hear about how you're think about AI, how you're feeling about AI, and I think it's far more interesting with the context of everything we've spoken about.
52:38
>> Yeah, I think of it as the most unbelievable tool I've ever seen to improve every single part of the work I do.
52:46
Like I am I have been blown away.
52:48
I've been a Power user now for a year and a half, right?
52:49
and a half, right? like just aggressively using every tool that comes out trying to understand the intricacies of the tools like stay trying to stay ahead of a field that's rapid rapidly developing and by the way I'm not a I'm not a technical person so I'm not an engineer and I'm not like a founder of a
53:06
tech company so my interest in this is purely at the level of like tooling like what tools are being developed for people like me to do our work better and honestly there there's been one other moment when I've been been this blown away and it was the first time I connected to the internet. Like the first time I
53:20
Like the first time I connected to the internet and I was like, "Wait, wait, wait, wait.
53:22
I'm connected to literally everything and everyone if I want to be the the great challenge for any kind of writer is one of the great challenges is like simply like getting stuff on the page that you think reflects the thing in your head.
53:38
You have an image in your head >> and in your head it's perfect.
53:40
It's like every pixel is exactly where it needs to be.
53:44
Now you need to describe that image to somebody else.
53:46
And that's where the challenge is.
53:48
M AI helps you do that better and faster. How does it do that?
53:53
Well, I'll give you an example actually from just a couple days ago.
53:55
I am I'm working to edit in my role as a as a publisher.
54:00
I'm working to edit a book about grief and the woman who wrote the book lost her daughter uh two years ago.
54:07
This book is extraordinary.
54:07
I actually haven't been able to edit it without weeping. Like it's that good.
54:09
Part of that is I'm a parent and when you read a book about somebody's child dying, you just it it hits too close to home.
54:16
There's a section in the book where she talks about how Judaism emphasizes the need for the body to be buried and in the ground very very quickly. Yes.
54:26
You're supposed to wait a maximum of 3 days.
54:28
That's the outer limit or something. >> Yeah.
54:30
Basically, I think the the soul or the spirit leaves the body after 3 days. >> Yeah.
54:34
And she talks about how there's actually a decent amount of writing in like Jewish liturgy about the importance of the speed.
54:41
Like why the speed matters, where does that come from?
54:43
And there are sort of two like abiding explanations, right?
54:47
And and one is that the spirit needs to to be back to God as quickly as possible or back to this back to, you know, the heavens as quickly as possible.
54:55
The other is that bodies if they were left out could become decayed.
55:02
They would start to like the the the flesh itself would would start to smell and rot and all these other things.
55:06
And so there was a there was a reason that was spirit and there was a reason that was flesh.
55:10
I wanted to understand that better and to understand what the rabbitical sources said about that better so that I could confirm that one she was telling me like she was speaking the truth. I'm not Jewish.
55:19
I don't come from this tradition.
55:21
But also if in case I missed anything like did we miss any quotes or ideas or something from the Talmud that should be in here.
55:26
Could I like go and spend a month like really getting you know understanding Judaism? Sure.
55:32
But instead, I could use AI to like take the paragraph and and ask AI to really give me sources and quotes and texture and nuance and please explain, you know, what this word means and what this word means, like is this the actual explanation?
55:47
And it gave me really incredible thoughts so that I could verify the information.
55:51
I could share some things with her that I learned that might make for better editing, right?
55:56
like it actually enhanced that paragraph taking it and putting it in AI and just asking it a series of questions.
56:00
There are people who could say that's unfair and I would say well all I did was just Google on steroids, right?
56:08
Like all I did was just like Google what I what would have taken me 10 Google searches took me one query with Claude.
56:13
Claude, by the way, is my preferred is my AI of choice.
56:17
I actually prefer it over Chat GBT. Okay.
56:19
Um I think it's friendlier for writers.
56:20
Uh and I think it has just a bit more personality.
56:22
I'm not the first one to say this.
56:23
There have been a number of pieces of writing about this, >> but the the point is that I think what it does is it one, it enhances your ability to research >> and it allows you to pull sources together that you wouldn't have otherwise thought about, right? There's a second thing.
56:37
Psychologically, having an editor that's always on call is new and super powerful.
56:42
I It used to be and it still is that you have editors and they help you punch up your work, right? No writer works alone.
56:49
They have people who work with them.
56:51
I now have the world's greatest editor, the world's smartest editor who never complains, who never gets tired, who never turns off.
57:00
So, if I'm working at four o'clock in the morning and I need my editor, I've got it. It's right there.
57:04
So, if I have a paragraph that feels flabby or if I have a word that doesn't quite sit right, I can put it in and say, "What are some other options for this?"
57:12
or "What's wrong about this?" Right?
57:13
So, that's like the editorial function.
57:17
There's another important function that I use it for.
57:21
I think and this is something that t that one of my another one of my kind of people in the hall of heroes is Tyler Cow.
57:25
I know you're close to him as well. >> Love Tyler.
57:28
>> One of the things that Tyler Tyler talks a lot about is like the ability to argue the opposite position is insanely important.
57:32
And so sometimes, particularly with opeds, when I have an op-ed I've finished or something I've written where there's an argument, like a real argument, I will have Claude argue the opposite position for me.
57:41
argue the opposite position for me. I will have it write take write a takedown of this of this oped please criticize in 700 words this op-ed and I tell it I said and do not hold back I'll like add personality to it >> once I see how it's criticized the piece
57:59
I can then go back to my piece and strengthen it against those criticisms because everybody's got blind spots and so I have to actually be able to like unearth those blind spots so that I can address them and I would say nine times out of 10 the arguments that it makes really force me to Stop and think. Everything I've just described obviously
58:14
Everything I've just described obviously has hazards.
58:16
There are hallucinations. There are problems.
58:18
There are times when we get source material wrong.
58:20
But that's the whole point of human operators running these these, you know, these LLMs and using them judiciously.
58:26
I'm not substituting for the work of getting up every day and doing writing.
58:30
I'm using the tools in the places where it matters.
58:34
And I cannot emphasize enough how much better and faster my work is as a result. Bye.
58:38
Eastern Vasan has a line where he says AI is not end to end, it's middle to middle.
58:45
>> And what he means by that is when people criticize AI, they say, well, you're going to need to figure out what is the thing you want to do in the first place.
58:54
Hey, there's going to be hallucinations.
58:56
You have to check it at the end.
58:56
That's the end to end stuff.
58:57
Humans have to work at the very beginning to set the vision.
59:01
Humans have to work at the very end to >> to verify, to fact check, to make sure everything's good.
59:06
But a lot of that middle to middle work can now be done by AI.
59:10
And and also I I think look I think a lot of the criticism about AI is being leveled by people who don't use it.
59:15
I'll just be honest like I think a lot of the people who are critiquing it are people who have an understandable anxiety about how it might threaten their work, their income or just their like position in life, right?
59:27
But a lot of them don't actually use AI.
59:29
Like they don't actually sit down with the tools and sit down and like put things in and play around and learn how to use it.
59:35
Learning AI, learning how to use these tools effectively is a skill unto itself.
59:41
Learning how to ask better questions, create better prompts, use it for things like numerical analysis, use it to write code.
59:46
These are all actually things that take numerical analysis. >> Okay.
59:50
So, you're a word person.
59:50
I'm a word person, but often word people >> I'm not a numbers guy. >> Let me tell you that. >> Yeah.
59:56
And I I think I used to be a numbers guy.
59:57
I was much more math oriented earlier in my life, but now I've like long since abandoned that p those those passions.
1:00:02
But if you if you feel like you're like let's say your numerousy as compared to your literacy.
1:00:09
Let's say your numeracy is not as much as you'd like it to be.
1:00:10
Chat GBT in particular is extraordinary at number crunching spreadsheets taking things that are like super complex and coming up with analogies that are number related.
1:00:19
I needed to write something the other day and I was trying to compare the distance that I had written about to the number of times we a spaceship would have to travel around the moon. Right.
1:00:29
Yeah, I could probably that math is not that hard to do, but it's much better having Chat GPT do it, right?
1:00:34
And it's much more accurate and then I can fact check it and make sure everything's accurate.
1:00:39
It it's it's I I had a friend who's an engineer at a very prominent technology company that is doing a lot with AI. Let's just say that.
1:00:44
And I asked him about AI because engineers in particular are also feeling the same pressure that AI could replace them, that it could be a threat to their livelihoods.
1:00:52
And I asked him what he thought. He has a family.
1:00:54
He has a stake in the future of his financial life, right?
1:00:58
He's not independently wealthy.
1:01:00
And he said, "AI is the sharpest knife that an engineer has ever been given."
1:01:05
He said, "But it's still a knife.
1:01:05
I've still got to cook the meal, right?"
1:01:07
And so I think of it the same way.
1:01:09
I'm still cooking the meal when it comes to the Kobe book.
1:01:13
I'm still cooking the meal when it comes to all of my other projects.
1:01:16
But AI is an exceptionally sharp knife, and it is unlike anything I've ever seen.
1:01:21
There's one final piece that people don't necessarily think about that I talk about a lot when I encourage people to try using AI.
1:01:26
My my daughter doesn't have a hard time writing.
1:01:33
>> It's because she has no self-consciousness about the quality of her writing.
1:01:36
>> She doesn't care if it's good or bad. She just does it.
1:01:38
And it's it's an unadulterated childlike approach to creation.
1:01:42
And by the way, it's like marvelous.
1:01:44
Like all parents have experienced this at some point.
1:01:45
It's why, by the way, we put our crappy drawings of our kids stuff on the fridge is because like we're just like, "Well, look at this." You know?
1:01:50
Um, but the the the bigger point is ego is not interfering.
1:01:55
Self-consciousness is not interfering between the impulse that my daughter has to write something and the act of writing it.
1:02:02
Between my impulse to write and the act of writing is people who are going to hate me.
1:02:08
The people things are things people are going to say on Twitter like like all the interferences that get in the way.
1:02:13
all of the stuff that clo like clouds up cabbages up your brain that leads you to say, >> "Yeah, >> you know, I should shove this essay.
1:02:21
It's not going to be any good."
1:02:21
Like, and what if what if somebody doesn't like it or what if they think less of me or what if they think what if they think what if they think.
1:02:27
What AI does is actually allows you to shortcircuit a lot of that noise because it gets you to a finished product much more quickly and effectively.
1:02:36
So, I'll give you an example.
1:02:37
There's a there's a particular uh AI tool I like called Whisper.
1:02:40
I think it's called Whisper Flow. Yeah.
1:02:43
WPR and it's really really really effective voice dictation.
1:02:46
And so sometimes if I'm feeling really stuck or I feel like I'm not like I'm not myself that day or something's off, I will use Whisper Flow to just dictate thoughts and it'll do a very good cleaned up transcription or translation of what I just said.
1:03:00
And then at least I've got a bad first draft that I can play around with.
1:03:04
And I didn't get in my head about it and I didn't wait and wait and wait and agonize and research and clean the kitchen and make sure my shoes were all lined up by the door and all the stuff that we use to excuse ourselves from actually finishing the work itself.
1:03:14
AI is an anxiety antidote.
1:03:17
It's the people people think AI causes anxiety and I'm for sure for some people it does.
1:03:24
For me, it's been the ultimate antidote to the thing that prevents me from getting my work done because I can get to a bad first draft very, very quickly and then I can bring to it polish and flare and attention and refinement and all of those things.
1:03:37
And I think that's seriously underestimated.
1:03:39
Like I'll give you an example.
1:03:41
This is a little it's a little personal, but it's not.
1:03:43
I'll do the the broad strokes.
1:03:45
I had to write an apology to somebody like two or three months ago, and I've been dreading this note.
1:03:50
Like this is like one of those notes you're just like, "Ah, this person was a friend.
1:03:53
I maybe did something wrong or I said something wrong. What do I say? That kind of thing.
1:03:56
And so I I I basically used Whisper Flow.
1:04:01
I closed my eyes and I just said what I wanted to say to them and I had they they got a bad first draft transcription of it.
1:04:08
But it took a what would have been like what I don't know months of agony over a note and turned it into an email that I could take, edit, and send very very quickly. Right? It's still my words.
1:04:19
It's still my thought process.
1:04:21
AI just helped me overcome the anxiety.
1:04:23
And so for me, it's been an interesting tool psychologically as well as practically.
1:04:28
And I'm happy like the practical use cases are voluminous.
1:04:30
People are still discovering exactly what it can do.
1:04:34
>> But for me, it's been a a superpower.
1:04:37
And I think people who are running away from it, by the way, are doing so at their peril.
1:04:39
I think I think of it like this.
1:04:43
>> Could I write my books by by by hand? Yeah, Robert Caro does.
1:04:46
So, you know, no shade to be literally like literally by hand. >> Yeah.
1:04:51
Could I write them by typewriter? Sure.
1:04:52
But I'm choosing to use a word processor.
1:04:54
That's how I think about AI.
1:04:56
AI is the next iteration of that.
1:04:56
I am choosing to use this tool.
1:04:58
The words are still my own.
1:05:00
The research is still my own.
1:05:02
The facts are still my own.
1:05:02
The interviews are still my own.
1:05:03
All those things are still, they still belong to me.
1:05:05
They're still coming from my brain.
1:05:07
AI simply accelerates all of that and gives me a far bigger just canvas of research and potential options for words and phrases and paragraphs.
1:05:14
And so I don't I don't see how any modern writer couldn't use AI.
1:05:18
And I think the idea that it is like stealing work or no, it's been trained on work, right? It's not stealing.
1:05:26
It's it's it's borrowing to learn.
1:05:28
So did Google books, but there was no outcry about Google books, right?
1:05:32
Like like there were there's plenty of information on Google that is the quote unquote like like cliffnotes version of a given topic or fact or book or novel or something.
1:05:40
There's not the same outcry.
1:05:42
I think of it very much in the same spirit.
1:05:44
And I think the courts are going to, by the way, going to find the same conclusions, too. Hm.
1:05:50
>> You've been looking a lot into the book industry and the book industry is is uh a dinosaur. A dinosaur. A Tyrannosaurus Rex.
1:06:00
So, you've been looking at the Tyrannosaurus Rex.
1:06:03
>> And >> you were telling me that you went in and you were like, I have a feeling that this this this industry situation is a little a little wacky.
1:06:11
Lots of nonsense going on.
1:06:13
And it sounds like that's been affirmed. Yeah. So, what's going on?
1:06:18
>> Well, I think this is this should be comfortable to anybody.
1:06:19
This should be comfort to anybody who's listening or watching who wants to do a book who thinks that it's impenetrable as an industry, right?
1:06:27
Or thinks it's impossible to do or they have to have the right agent or go to the right parties or meet the right people.
1:06:31
Like, I' I've been doing books for 15 years now, right?
1:06:35
I and I got pretty good at it over time.
1:06:37
What I noticed when I was doing my books with traditional publishers is that all of the things that traditional publishers used to do, they started to do less and less of, right?
1:06:46
So like marketing or good cover design or editing or all these things.
1:06:53
In almost all of my projects with traditional publishers, I have had to pay for editing on my own just cuz I wanted extra editing.
1:07:00
I had to pay for my cover design for the founders because I wanted a better cover, right?
1:07:03
And I thought to myself, wait, so I'm doing a lot of these labors, and by the way, like I've had great relationships at Modern Publishers, like I I think the world of my editors, they did a great job.
1:07:14
They just they were so belleaguered.
1:07:17
There were so many projects on their plate that you always felt like you were kind of like getting whatever the table scraps were, right?
1:07:23
And to me, that was one problem with the industry is I just didn't feel like I was like getting the kind of focus and attention that one would want, and I was paying other people to like help me with my work.
1:07:33
Then the other thing I noticed is I had friends whose projects were being turned down, but they weren't being given very good reasons for why they were being turned down.
1:07:39
And the some of these, by the way, become legendary case studies, right?
1:07:41
Was legendary case studies of how like, I don't know, like Harry Potter was turned down by everybody.
1:07:46
4-hour work week was turned down by everybody.
1:07:48
And then I also noticed that there was a real allergic reaction to AI tools, to AB testing, to technology, to advertising, to all of the things that in the digital world if you if you become a digital native first, you learn like wait, you can like test everything and anything and make your products better as a result.
1:08:09
So once I started to kind of like nerd out on this stuff a little bit, I then connected with another another writer friend um who also has a podcast, Jim Oanisy, and we decided to create a new publisher.
1:08:20
So we created Infinite Books.
1:08:21
And it turned out that when we kicked the tires on almost every part of publishing, there was so much desire for a new way of doing things.
1:08:29
I'll give you a really simple example.
1:08:31
Um the way publishing contracts work is you typically like will get an advance and then you earn like you earn like 10 somewhere between 10 and 15% on a given sale price of a book until you make back your advance.
1:08:46
So you only see new money once you've made back your advance.
1:08:49
There are a lot of people who don't want that deal.
1:08:51
What they want is David, you've published a book.
1:08:53
If the book is $10, when it sells you make seven, I make three as the publisher. They want that deal.
1:08:59
But that deal never existed because most publishing contracts were exactly the same.
1:09:04
They'd been done the same way for I don't know the Paleolithic era, right?
1:09:07
Like it was in they've been done the same way the exact same time.
1:09:10
And if you even asked questions about whether something could be different, you were called a problem author.
1:09:15
So you were like, "No, no, stay in your swim lane author person.
1:09:17
You don't you don't don't concern yourself with the commerce of this. Don't ask these kindh." So you're the artist. Go do your art thing. Right?
1:09:27
But for for a lot of us, we're we've had to develop multiple skill sets.
1:09:31
We've had lives in business that we that then translate over to our writing.
1:09:36
We at at Infinite Books, we're like, well, why don't we just talk to authors about the deal they want and then come up with a deal that makes sense for us financially.
1:09:41
So, for a number of our authors, we're giving away 70% of the royalties.
1:09:45
They might not want an advance.
1:09:46
Like, we're not going to do an advance and 70% necessarily, but and some authors do want an advance, and we'll work with you if you do, but there are a lot of authors who are just betting on themselves.
1:09:54
They just want a publisher to help shepherd the project and they want the lion share of the revenue.
1:09:58
That's not a hard thing to do.
1:10:01
That I'm not This isn't like inventing a new rocket and taking it to Mars.
1:10:02
Like it's like literally just shifting a contract.
1:10:05
Give you another example.
1:10:07
Here's like a good AI example.
1:10:09
There's all this hostility in the publishing industry to AI.
1:10:10
People are saying it's it's they've trained the LLMs on all these books and they're going to steal work from authors and they're going to be able to create stuff and it's all going to be slop and it's all garbage. Okay.
1:10:23
There are every few years you read about a scandal in the pl in the in the industry and the scandal is plagiarism.
1:10:29
Some author whether deliberately or accidentally will copy a sentence or copy a paragraph or copy chapters and they'll get tred and feathered.
1:10:36
Their careers will be ruined.
1:10:37
Many of them like they never come back from it. Right? Something will happen.
1:10:40
The publisher doesn't catch it.
1:10:41
They have to stop the presses. Huge scandal.
1:10:43
New York Times article career done. Right?
1:10:45
These people enter deep depressions.
1:10:48
Some of them never come out of it. Right?
1:10:49
or they get out of it and there's always a little bit of like a they have a checkered past or something.
1:10:54
In the age of AI, there should never again be a plagiarism scandal.
1:10:59
Because think about it, you could you can you can take someone's manuscript and as the publisher, this is your responsibility as the publisher, upload it and check to see whether this person stole work.
1:11:08
If they did, you either have a conversation with them and say, "Hey, listen.
1:11:13
Were you just did you just miss some quotation marks here? Was this accidental?"
1:11:17
or you look at the work and you say, "Oh, this person is actually just copying and pasting and they're stealing." Right?
1:11:21
There should never after 2025, there should never be another plagiarism scandal ever again.
1:11:27
AI is too good for publishers to not use it to check for something like that. >> Is that cheating? I don't think it is.
1:11:34
I think it's just good, honest, responsible publishing.
1:11:39
Like, why wouldn't you use it for that?
1:11:40
>> A final example, and this one's important.
1:11:42
I think there's this there's a there's a hottiness within publishing like an arrogance that publishers know best that they're taste makers that they know what the cover should look like. You don't know.
1:11:56
You audience don't have any idea what the cover should look like. We do. I disagree.
1:12:03
I AB test all my cover art and I use services that allow you to very quickly get hundreds of people to react to a cover. Why?
1:12:12
Because in the digital world, people are making snap decisions on Amazon and they're buying often based on the way a cover looks.
1:12:18
Look, you may like that or hate it.
1:12:20
It's the reality of the world we live in.
1:12:22
Why wouldn't you AB test cover art?
1:12:24
Well, because maybe your designer would be upset if you're at a publishing house. I'm sorry.
1:12:30
Like, that just isn't that isn't good enough.
1:12:32
That's not a good enough reason to not test what's going to work or not work.
1:12:36
And when you have tools available that allow you to cheaply test things that are going to work and not work and use that to sell more books, you should use those.
1:12:43
Some of those are AI tools, some of them are not.
1:12:45
But the point is, I just noticed a real lack of attention being paid to those sorts of tools.
1:12:49
And I wanted a publisher that was basically doing that natively and figuring it out.
1:12:55
So this is by the way this is like not these aren't popular opinions within the industry necessarily but if you talk to authors like the people actually creating the books they are wildly happy that these tools exist for their personal use and then that publishers are starting to adopt them because there's no going back.
1:13:13
Like you can very quickly get access to information, resources and feedback you couldn't before.
1:13:20
Authors are going to do it even if publishers don't. >> Yeah.
1:13:23
I had a I have a friend who really talented guy and he just published a book traditionally and I I have two copies of the book.
1:13:35
I have the original manuscript which is basically a printed out PDF with a cover he designed and a book that he wrote without any editing.
1:13:47
And then I have the final book done by the publisher with a change title and they made the the book cover.
1:13:58
And I've said this to him, it's an abomination. >> It's an abomination.
1:14:02
It is an absolute tragedy. >> Yeah.
1:14:06
>> To see what how degraded this book was.
1:14:07
And now >> I said to him straight up, I said, "Dude, >> you did not stand up for yourself like you needed to."
1:14:17
Y >> but what really irks me is the way that by going traditional he lost all sense of individuality.
1:14:28
And this is a guy who's unlike anybody I know who has a book >> that is >> just like every other book I see now.
1:14:36
>> Y >> and it's such a tragedy.
1:14:39
And I think part of the reason that we need alternate ways of publishing things is like the blob takes things and turns them into the blob.
1:14:48
And that's why you just see this homogeneity all over the place. >> Yeah.
1:14:53
>> Yeah. I'll give you another example that's really really compelling that somebody I'm talking to right now who's a super prominent author and he's done one kind of book and succeeded so well at it and he's a true craftsman cares a lot about the craft and he has been successful with this particular genre of book his publisher is a big five
1:15:11
publisher they love him to death he wrote a memoir uh which was an unexpected work he wanted to get it out on the page it was a bit of like mix think about like it was almost like personal therapy in addition to doing a wrote a memoir about his childhood and I guess he took it to both his agent and his publisher and they said to him, "You're really not the memoir guy, right? He is a brilliant like multiple
1:15:33
He is a brilliant like multiple New York Times bestselling author and because it's out of genre for him, >> right?
1:15:40
>> They didn't think it could work because quote unquote your fans only know you as this." >> Yeah.
1:15:45
>> You and I know that's BS.
1:15:45
If he did that book, people would love it because it was different, right?
1:15:50
Like just to get back to Taylor Swift for a second, we love her because she's had multiple eras, right?
1:15:56
Like we we want Why wouldn't you want your artists to reinvent themselves time and time and time again, right?
1:16:03
One of my favorite Metallica things is the the the when they partnered with the uh San Francisco Symphony Orchestra and they did the music with the symphony and the symphony is working with them to do something, right?
1:16:18
like you you obviously like there's a certain amount of creative risk that comes in doing that, right?
1:16:23
Like for every one of those there's like when Dr.
1:16:25
Dre did the Tango album and it was a huge flop, right?
1:16:27
But like you want to encourage a world in which authors are taking creative risks.
1:16:31
I don't know that the publishing industry does that enough.
1:16:35
And I know that because this person would be successful with this book and he's been successful with others books.
1:16:40
He's made his publisher a lot of money, but they don't want to take a chance on a memoir because he's quote unquote not a memoir guy.
1:16:47
I think this is one way to distinguish between art and content.
1:16:52
That what art is is you're trying to push on some sort of frontier.
1:16:54
The human being itself, we're not these static creatures.
1:17:00
You know, we deal with different joys, different sufferings as we change in life.
1:17:05
And there's a sort of meanderingness to life.
1:17:06
and you're trying to explore new frontiers.
1:17:11
And I think that that's what art is.
1:17:14
And then what content is is once you have a style, once you have a form, you begin to kind of have a quota that you need to meet.
1:17:23
And there's a very cookie cutter package sort of specs that you need to hit.
1:17:28
And I think that that's a lot of what you're saying is what traditional publishing gets people to.
1:17:35
>> I think that's part of it.
1:17:35
And look, here's the other thing.
1:17:36
It's like we shouldn't just turn this into like 30 minutes of bashing on traditional publishing. Like here's the thing.
1:17:42
>> These are exceptional professionals, many of whom are like world class at their craft.
1:17:45
Like this is an industry that is filled with super smart, super thoughtful people.
1:17:48
The the the problem is is that there's been so much consolidation and there's just less room to take risks because if you're if you have a bunch of books that aren't successful, like you're kind of costing the publisher money, right, without having a return.
1:18:01
So I can understand why editors feel the pressure they feel.
1:18:03
The thing is is that the entire business model is kind of predicated on your book being a hit within the first two weeks.
1:18:10
And if it's not a hit hit within the first two weeks, publishers sort of give up on it and move on to the next project.
1:18:14
That's one of the biggest issues.
1:18:16
So, one of my favorite one of my favorite books is Boys in the Boat, right?
1:18:20
It's a it's a quintessential example for me of the publishing industry getting it wrong. Here's why.
1:18:26
Boys in the Boat is a masterwork and it's a book about rowing and this rowing team, Berlin, the Berlin Olympics.
1:18:30
And it's it's an extraordinary story and it's beautifully told.
1:18:34
The book debuts, crickets, maybe got one or two reviews, no significant TV appearances, nothing happens with it.
1:18:44
And the publisher is just like, "All right, good. We're good. Enjoy your book, right? We're done. That was a write-off. Rowers pick it up."
1:18:51
Months, some months go by.
1:18:53
Rowers pass it to other rowers.
1:18:55
Then rowers start passing it to their families.
1:18:57
something like eight or nine months after the book debuts, it gets on the New York Times bestseller list and then it takes off like a rocket.
1:19:03
So then the rest of the world gets exposed to it and 10 years later it's a movie, right, with Tom Hanks or whatever on Netflix. >> Wow.
1:19:11
>> It takes a while for certain projects to take off, but the timelines in publishing are you are a hit within the first two weeks or you're just you're not like it's not going to work, right?
1:19:21
But meanwhile, we have example after example of people who continue to sell books over a long period of time and then hit their crescendo much later.
1:19:25
And I think that's the other thing is like the timelines in the industry force authors to basically chase instant success or you just like you're you drop like a like it's like we're not going to give you any marketing support.
1:19:38
We're not going to help you.
1:19:39
We're not going to do anything.
1:19:40
And it's not by the way it's not cuz they mean you.
1:19:42
It's not cuz they're mean.
1:19:43
It's just cuz they have to move on to other projects.
1:19:45
But what I actually have a suspicion about is that there are a number of projects that could have been successful if there had been just a little bit longer window attention paid to like how do we get this book in the right places?
1:19:56
And the way I know that is like my books continue to get attention.
1:19:59
They are evergreen books.
1:20:01
Somebody discovering Claude Shannon for the first time is going to seven years they don't care when my book was published.
1:20:07
They're going to find him now.
1:20:08
So I can continue to market my book now.
1:20:10
And it's as new to the person who's discovering it for the first time as it was to every other person who discovered it when it first debuted, right?
1:20:17
That also needs to change.
1:20:19
Like the time horizons on these projects are so short and it puts authors in this really uncomfortable position because they're basically like go go go. They have the launch.
1:20:26
If they succeed, they're like the hot new thing.
1:20:32
If they fail, they're forgotten about and nobody wants to do business with them again.
1:20:35
And that's really depressing.
1:20:36
Like it's like actually like a lot of these books should be revived.
1:20:39
a lot of these authors should get more support on how to market or how to be aggressive and make yourself into the kind of book that sells perennially.
1:20:48
The other thing that's crazy is that you wrote a coffee table book. >> Yeah.
1:20:52
>> About a carousel y >> in Brooklyn Bridge Park, which is >> you wrote about Claude Shannon, you wrote about PayPal, you write about Kobe now.
1:21:00
Like this is a huge outlier.
1:21:00
So what's the story of this?
1:21:03
>> So this is Yeah, this project was a labor of love uh in every way actually.
1:21:08
So this is this is the book. It's Jane's carousel.
1:21:09
Um, and it's actually a pretty pretty weighty substantial project.
1:21:13
Um, and the quick story on this one, I had a very young daughter and I was living in New York and I was at a loss for what to do with her all the time, right?
1:21:22
It's like, which is a classic parent problem.
1:21:26
And so, one of the things that we got into the habit of doing is we would go to the carousel, which is right on the water's edge in Dumbo at at right at the edge of Brooklyn Bridge Park.
1:21:36
and she for some reason my daughter just became obsessed with this carousel.
1:21:41
So I've ridden that carousel over 200 times.
1:21:43
One of the things you notice if you go to enough carousels in New York is Jane's carousel is a cut above all of the others.
1:21:53
>> And I kind of became interested in like why.
1:21:54
And so then I went on Google and I I learned that the woman who had put this project together, her name is Jane.
1:22:02
She had basically hand restored this carousel for 30 years.
1:22:04
And I remember thinking like 30 years like I can barely do anything for 30 minutes, you know?
1:22:11
It's like you don't you know and so I was like I was obsessed with her because I was like how do you do this for for three decades? Like why?
1:22:16
And so I wrote an email to her and it was like janejane carousel. com or something.
1:22:20
And I emailed her and I said listen I'm looking for a gift for my daughter that is not like a Chinese plastic toy thing.
1:22:26
Do you have any like a do you have a book that I could like write a note to her inside and then maybe it's like a picture book or something?
1:22:33
like I assumed she'd like done something and she's like, "You know, I don't."
1:22:36
And then I I kind of wrote back and I was like, "You should really think about doing one.
1:22:39
I think it'd be really cool."
1:22:40
And she said, "Let's have lunch."
1:22:42
So, we get together for lunch.
1:22:43
And basically what I said is I was like, Jane, you know, the story of this carousel is a story of a of a of a creation from 1922. It survives a world war.
1:22:53
It survives a fire in Idora Park in Ohio, which is the first park that it was placed in.
1:23:00
It is crafted at the during the heyday of American carousel making when each of these horses was actually handcarved like handcarved hand painted.
1:23:07
This is when carousels truly were like these incredible works of art.
1:23:12
And I said and you then buy it after it's been burned and hand restore it for 30 years not knowing if it's ever going to get into Brooklyn Bridge Park.
1:23:22
Like what could possess you to do? This is a story.
1:23:23
And I said and I think you should really think about doing it as a visual like a coffee table book.
1:23:28
and she went for it and we sat down with a contact of hers who was at Feden.
1:23:34
Fedden is one of the world's pre-minent coffee table publishing companies next to Tashin Oelene Rosolei.
1:23:39
They make beautiful books, beautiful books.
1:23:41
So we go in and I'm there.
1:23:44
I'm like ready to pitch and I we're sitting in front of all these like assembled editors, right, who are a lot cooler than me and have a lot better aesthetic sensibility than I do.
1:23:50
And I said, "Listen, you you need to take this project on because the book on the Highline is exactly like this.
1:23:56
the Highline is a Marvel and that coffee table book is so beautiful and it tells the story of how the Highline was created and it's got all these amazing like design features and elements.
1:24:05
I said just in the same way that people appreciate the Highline, they love the carousel and I know this because I love the carousel and I'm a parent of a of a young kid who loves his carousel so much and the editor at Fiden starts laughing and I kind of was like, "What? I'm sorry.
1:24:21
Did I like I'm did I offend you?"
1:24:23
He's like he's like, "No."
1:24:23
He's like, "Jimmy, I was the editor on the Highline book."
1:24:28
>> And he's like, "And I love that project and I do want to do this project for the exact same." >> Wow.
1:24:32
>> And so then we started working on this book.
1:24:34
And the the tragic part of the story is that I did my last interview with Jane >> and it was right around COVID times and it was like uh June, May or June of 2020. She had gotten COVID.
1:24:44
She went in to get the all clear, but then they found stage four lung cancer.
1:24:48
So she would never survive to see the book done, but her husband and her son have carried on the carousel's legacy and the book is a monument to her work.
1:24:56
And to give you to give people watching and listening a sense for how committed she was to this carousel, she refused to have the horses chemically stripped of their paint because you could clean up a carousel just by like tossing a bunch of chemicals into the horses, getting rid of all the paint, and then starting from scratch. She said no.
1:25:17
And the reason is because if you didn't if you did that you would lose whatever the original coloration was. You wouldn't know.
1:25:23
So for three decades using Xacto knives which I have seen which I have held.
1:25:28
She would file away the paint on every part of these horses to see what the original color was and then color match to that paint and then restore the horses that way.
1:25:41
She like she brought in the best pin stripers in the world to do pin striping because there's a lot pin striping on these carousel horses.
1:25:46
She found an organ that matched the exact organ that the carousel used to have.
1:25:51
She did a an architecturally and historically faithful restoration of this carousel.
1:25:55
And it took her three decades to do it.
1:25:57
And it was I could not I could not believe in the same way that I can't believe Robert Carroll would do 10 years on a book.
1:26:03
I couldn't believe that somebody would do 30 years on a carousel.
1:26:07
So learning about it, I was like, there's a story here. I mean, this is amazing.
1:26:11
And so that's what resulted.
1:26:12
And it it captures one woman's commitment to something that an obsession about something that like surpasses understanding, right?
1:26:19
Like it it really to me the the the greatest things that I get to encounter in my life as an author is when I meet or find somebody that is that obsessed with something, right?
1:26:29
Because as to get back to the beginning of our conversation, what is at the heart of that?
1:26:32
The heart of that is at least partly love.
1:26:34
you like have to love this thing so much that you're willing to give up decades of your life for it, right?
1:26:42
And like if you have one wish for the people in your life, it's that they find something they love that much, right? And she did.
1:26:48
She had she had the carousel. >> I love that story. Um, what did you learn?
1:26:54
How is publishing one of these books different? >> Yeah.
1:26:58
So, it it it's I mean the almost the entire process is different in the sense that it's it's not that many words, right?
1:27:03
So it's it's it for one thing it's and what I would say is it's actually um it's an artistic challenge and so you have to you have to think a little differently in how you structure and present information and you don't you know you don't get the benefit of like here's 70,000 words on the carousel.
1:27:20
No, like that's not what this is.
1:27:21
This is designed to be flipped through in exactly the way that you're flipping through it, right?
1:27:24
And so you have to think a lot about what are we keeping, what are we cutting, how are we presenting certain images, what another thing I learned is like captions are super important.
1:27:32
So, I like rewrote and wrote all the captions, right?
1:27:35
>> What goes into writing a good caption? >> Word economy.
1:27:37
I mean, talk about word economy.
1:27:38
You don't have any space at all, right?
1:27:39
So, you really you've got to decide what you're going to keep, what you're going to cut, what stories you going to tell, that kind of thing.
1:27:43
Um, another good example of something that I learned in doing this book is, you know, you you really do um in in coffee table book publishing, you get what you pay for.
1:27:54
So, that's a full color book, which costs a lot more to make than a black and white book.
1:27:57
Um, we did a really clever thing in the middle of the book where we used tissue paper to show the color of the horses and that was a design decision, but obviously it cost money to have regular paper and then tissue paper.
1:28:10
We did little fold out things, cutout things.
1:28:12
We, you know, not cutouts, but foldouts of of different things so we could show all the horses in one place.
1:28:17
It it basically like I had never had the chance to think about the design of a book as creatively.
1:28:23
And I will say part of this is like it wasn't my my work at all.
1:28:27
It was the brilliant people at Fiden who put all of this together and really made it into something that was monumentally beautiful.
1:28:34
So this is a great example of I wanted people to see how obsessed she was with the colors.
1:28:37
So we figured out how to use tissue paper to show the color on top of a black and white image of a horse.
1:28:43
And you can see right there, by the way, in those two pages, you understand why she did not want to chemically peel the paint from the horses because the only way to get the original colors was to file away and file away and file away, layer after layer after layer of paint, and then do little notations for what the paint was, and then have the paints recreated.
1:29:00
I think that what I'm really taking from this conversation is just the liberty to just follow wild rabbit holes and intersections y or you know what, whatever the word is. I don't even know.
1:29:14
I'm very moved, so I can't really think clearly right now.
1:29:16
But but I think that as you were talking, I was like, "Oh my goodness, he loves this so much.
1:29:21
This is such a beautiful story."
1:29:22
And as you were talking, I was like, "We have taken such a departure from the rest of this conversation."
1:29:28
And like that is the point that I'm trying to make. point.
1:29:31
The point is that I mean I think the point is you you you know you have felt the same thing about your podcasts and about different projects you've done when you you obsess over it so much.
1:29:42
You enjoy it so much that you simply cannot help but think about it and work on it and continue to refine it.
1:29:52
>> And it's not by the way this is not for everyone.
1:29:54
Like the truth is like there are some real hazards to living this way.
1:29:57
Like socially it can exact a huge price, right?
1:30:00
And you and and like honestly you like you have to find friends like David because all your other friends are like you're too much for me, right?
1:30:05
Like I can't I can't hang out with you and have you talk about the carousel again like for the 15th time, right?
1:30:10
Um like that's like that's a thing.
1:30:12
But at the same time when you feel when you find somebody else like that, it's a little bit like probably the conversation that Kobe Bryant was having with George RR.
1:30:22
Martin, you just you know that energy and you can sense that energy and you feed off that energy.
1:30:26
And so it's one of those things that like that's if I have one quest in life, it's that.
1:30:32
It's just to find that and then then to turn that into stories.
1:30:34
So for me, that's a big part of what I I feel I'm a part of is like a tradition of storytellers.
1:30:41
>> Dude, I could hang out with you forever.
1:30:43
Thanks for coming on the show. >> Of course, man. Thank you. So fun of me.