We talk to the guy who knows Silicon Valley’s darkest secrets

0:00:01 I’ve got Steve Jobs stories.
0:00:02 I’ve got Jack Dorsey stories.
0:00:04 I’ve got Ross Ulbrecht stories.
0:00:05 You name it, I got ’em.
0:00:07 ♪ I feel like I can rule the world ♪
0:00:10 ♪ I know I could be what I want to ♪
0:00:12 ♪ I put my all in it like the days of ♪
0:00:14 ♪ On the road let’s travel never looking back ♪
0:00:17 – All right, Sam has been telling me about a book
0:00:19 for probably 10 years in a row.
0:00:21 And I finally got around to reading it this year.
0:00:22 And the book is American Kingpin.
0:00:26 It’s a story of the Silk Road of Ross Ulbrecht
0:00:31 who created it, grew it to great, you know, prominence,
0:00:34 ended up going to jail, what we thought was for life.
0:00:35 And then he just got pardoned by Trump.
0:00:37 And so Sam just reread the book.
0:00:38 I read it this year.
0:00:39 We both love this thing.
0:00:41 It’s a page turner.
0:00:43 And the author, Nick Bilton, not only wrote that,
0:00:45 but he wrote Hatching Twitter and a bunch of other stuff.
0:00:46 Fascinating guy.
0:00:48 And he’s here with us today on MFM.
0:00:49 So let’s do it.
0:00:50 – Nick, what’s going on?
0:00:52 We wanted to talk about all types of stuff.
0:00:53 We want to talk about storytelling.
0:00:55 We want to talk about things that you researched
0:00:56 that didn’t make the book.
0:00:59 We want to talk about like the OG stories of Silicon Valley
0:01:01 ’cause you’ve been covering this stuff forever.
0:01:03 But you’re like one of the three people
0:01:06 who we’ve had on the pod that I’m like nervous to talk to.
0:01:09 And I stayed up all night like reading everything about you.
0:01:10 – Don’t be nervous.
0:01:11 This is exciting.
0:01:12 This is fun.
0:01:12 It’s going to be great.
0:01:14 We’re going to tell some crazy stories.
0:01:16 I’ve got Steve Jobs stories.
0:01:17 I’ve got Jack Dorsey stories.
0:01:18 I’ve got Ross Ulbrecht stories.
0:01:20 You name it, I got them.
0:01:23 – Who of all those people, have you become friends
0:01:25 or admire any of them?
0:01:28 Or are you like a strictly like a journalist
0:01:30 who doesn’t cross the barrier?
0:01:32 – Well, that’s a great question.
0:01:34 I feel like we should save.
0:01:35 I should save that answer
0:01:37 ’cause I’ve got such great stories
0:01:39 about all these people, about Bezos, everyone.
0:01:43 Where there are some that I have become friends with
0:01:44 and then unfriends with
0:01:46 and some I’m still kind of friends with.
0:01:50 But let’s save that for when we get into the hatching Twitter
0:01:54 Elon Musk, Jack Dorsey territory of this pod.
0:01:56 (upbeat music)
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0:02:29 – I was listening to an episode with David Perrell.
0:02:30 It was all on writing.
0:02:33 And you talk about what makes a great story.
0:02:36 And this sounds like a backhanded compliment.
0:02:38 I think that your writing’s amazing.
0:02:39 Your storytelling is amazing.
0:02:41 I think you just happened to pick
0:02:44 the best story of all time with the Silk Road.
0:02:46 It was set up to win.
0:02:49 Well, I think, let me just tell you how I came to the story.
0:02:51 So I was a reporter at the New York Times.
0:02:54 And in Silicon Valley, covering tech,
0:02:56 I was writing about Apple and Facebook and Twitter.
0:03:00 And I don’t even know how to describe this moment in time.
0:03:03 It was like 2008, 2009.
0:03:08 It was right after the bubble had popped, the second bubble.
0:03:11 And it was again, once again, this no fly zone
0:03:15 to be in Silicon Valley, to do startups and whatnot.
0:03:18 And I started covering these companies that were not…
0:03:20 The idea of one of them being a trillion dollar company
0:03:22 was just ridiculous.
0:03:23 That would never happen.
0:03:26 And I would spend time with Steve Jobs and Bezos
0:03:29 and Zuck and Dorsey and all these guys.
0:03:32 And I wrote the Twitter book, which we can talk about
0:03:35 and there’s incredible backstories to that.
0:03:38 And of people trying to kill the project
0:03:39 and so on and so forth.
0:03:41 But I’d finished the Twitter book
0:03:42 and the Twitter book had done really, really well.
0:03:44 And I was looking for a new book.
0:03:47 And I really love writing books.
0:03:50 It’s one of my favorite forms of writing to do.
0:03:54 And I heard about this guy who had started the Silk Road,
0:03:57 who had been arrested at this little public library
0:03:59 that was like four blocks from my house.
0:04:03 And I knew the library and I knew the area
0:04:04 and I also knew the Silk Road.
0:04:07 And so I wrote a piece for the New York Times about it.
0:04:08 It’s just like a short piece.
0:04:10 And then I was like, maybe there’s a book in this.
0:04:13 And as I started to dig further and further,
0:04:15 it just felt undeniable.
0:04:17 It was like, it was just an unbelievable story
0:04:19 of this kid who, I say kid,
0:04:20 ’cause he was very young at the time,
0:04:23 but he grew up in Austin.
0:04:27 He was incredibly smart, 1600s on his SATs,
0:04:32 studied astrophysics, went off to one of the best schools
0:04:36 and then had this libertarian idealism to him
0:04:39 that is no different to Travis Kalanick
0:04:43 when he’s building Uber and all these other people
0:04:44 in Silicon Valley.
0:04:47 And he decides that drugs should be legal
0:04:49 and the government should not be able to tell you
0:04:51 what you can and cannot put in your body.
0:04:55 And the only reason that the drugs lead to deaths
0:04:57 and murder and so on and so forth
0:04:59 is because the government has so much control over it.
0:05:01 And so he takes the onion browser,
0:05:03 which is the secret browser
0:05:05 that you can, where the dark web exists.
0:05:06 And then he takes Bitcoin,
0:05:09 which both kind of come along at around the same time.
0:05:11 And he creates this proof of concept,
0:05:13 which is this website called the Silk Road.
0:05:14 And then next thing you know,
0:05:17 he’s making millions and millions and millions of dollars
0:05:19 a day is the biggest drug dealer on the internet.
0:05:22 – By the way, how good was the branding for that?
0:05:24 The fact that he called himself the Dread Pirate Roberts,
0:05:27 the Silk Road, the logo behind it,
0:05:30 the branding was actually like, it was pretty brilliant.
0:05:31 – No, the branding was great.
0:05:32 There was, I forget the name,
0:05:35 there was a name that he had originally wanted to call.
0:05:36 It was like some terrible name.
0:05:38 – It was called like hardcore underground
0:05:39 or something like. – Yeah, I think.
0:05:41 – Something where it was like,
0:05:44 does it sound like I’m interested in that?
0:05:46 – But what’s fascinating is at the time,
0:05:47 he’s living in Austin,
0:05:48 he’s got this girlfriend, Julia,
0:05:50 and they’re kind of in this toxic relationship.
0:05:55 And he has this business and it’s a pretty nice business
0:05:57 where he goes around and he collects books
0:05:58 that people want to get rid of
0:06:01 and then sells them and mails them out.
0:06:03 So when he moves into the drug trade
0:06:06 and he goes to Bastrop State Park
0:06:09 and he rents a cabin and he grows mushrooms
0:06:10 so that he could sell drugs on there
0:06:11 to show that you can sell drugs on there.
0:06:13 And then he starts mailing them out,
0:06:16 like he’s mailing the books out and then the drugs out.
0:06:18 And like, and it all kind of,
0:06:21 it all comes together in this very, very unique way.
0:06:24 What ends up happening is Gawker,
0:06:27 the website that is obviously now defunct.
0:06:29 They write about it and then that’s it.
0:06:30 It’s like game over.
0:06:32 Like everyone on the planet knows about it
0:06:33 and senators are coming after him
0:06:37 and every government official from the IRS to the FBI
0:06:38 to the Secret Service to the DEA,
0:06:41 they’re all trying to hunt down the Dread Pirate Roberts
0:06:44 and Ross essentially goes on the run around the world
0:06:46 as they’re trying to catch him.
0:06:47 Yeah, it’s one of the best things about the book
0:06:49 is that it starts with like,
0:06:51 I don’t know how much of this is your conjecture
0:06:53 versus you had his diary, I guess,
0:06:54 and you knew some of his thoughts,
0:06:56 but it’s like, he knows he’s smart.
0:06:57 He wants to do something special.
0:06:59 He’s sort of bummed out that he hasn’t done anything
0:07:01 interesting or special with his life
0:07:03 and you know, has sort of tried
0:07:06 but hasn’t really made it yet doing anything.
0:07:07 And then you’ve got his girlfriend
0:07:08 and there’s that part of it.
0:07:09 They got the libertarian ideals.
0:07:11 And then it leads to, you know,
0:07:14 the thing escalates like crazy where I think,
0:07:15 I don’t know if it’s peak,
0:07:17 but I think Silk Road was doing like, you know,
0:07:20 over a billion dollars like GMV through the marketplace.
0:07:22 And there’s like, you know,
0:07:24 murder for hire plots going on.
0:07:26 Like it escalates like the craziest crime movie
0:07:29 would escalate, but I like that you had that beginning part
0:07:31 where it wasn’t just this criminal mastermind.
0:07:33 It was like this smart kid, you know,
0:07:35 just trying to do something
0:07:36 and had a certain set of ideals.
0:07:39 How did you know what he was thinking?
0:07:41 How did you get access to his diary?
0:07:42 Why does a writer like,
0:07:44 how does a writer like you get that?
0:07:45 And you got a lot of stuff.
0:07:47 You got like the footage of the library
0:07:48 where he got arrested.
0:07:50 You got like the chat logs from, you know,
0:07:51 from like with the government.
0:07:53 How did you get access to all this information?
0:07:56 Well, I can’t tell you exactly how I got a lot of it
0:07:59 because that’s the, that’s investigated reporting.
0:08:01 And, and I, you know, obviously can’t divulge
0:08:02 where it came from.
0:08:04 But the way I approach these stories
0:08:08 is I want to know everything, literally everything.
0:08:11 And so I have these researchers who work for me
0:08:13 and one of them, one of them actually used to do
0:08:16 OPPO research for the, for the Democratic party,
0:08:19 trying to find, you know, bad stuff on Republicans.
0:08:21 And we literally just blanket approach it.
0:08:22 And what’s been really interesting,
0:08:23 I have a new project, which I can’t talk about,
0:08:26 but I can tell you a little bit about how I’m reporting it.
0:08:27 What’s been interesting is I have this new project
0:08:31 that we’re doing and we’ve been using Google LLMs notebook.
0:08:34 And so now we stuff millions of words into these things.
0:08:36 And I can just query it, whereas before we had to build
0:08:39 like Excel spreadsheets and databases.
0:08:42 And like, it was very, very complicated the way we did it.
0:08:44 But we kind of put into three tranches.
0:08:47 So we, we have the Dreadpire Roberts
0:08:50 and we get access to the chat logs
0:08:52 that were on his laptop,
0:08:54 which I don’t actually know if he knew were there
0:08:56 ’cause they were in a hidden folder.
0:08:57 And I don’t think he actually knew
0:08:59 he’d been saving them or maybe he was, I don’t know.
0:09:01 And then there’s some diary entries.
0:09:04 He’d literally been making a diary about the thing
0:09:06 ’cause he would be the best line ever
0:09:07 as he thought there’d be a book written
0:09:08 about his life one day.
0:09:12 And then we, and then we go through social media
0:09:14 and we, and we get all the photos
0:09:15 and all the posts and all that.
0:09:17 And we, everything’s on a timeline.
0:09:18 It’s all got timestamps.
0:09:19 And then the, and then lastly,
0:09:21 it’s the interviews with everyone.
0:09:23 And with, as far as like, you know, we reach out,
0:09:26 we get your books and you go and you find out everyone,
0:09:28 he went to elementary school with the middle school
0:09:30 and high school and you interview everyone.
0:09:32 You’re, you find the neighbors, you,
0:09:34 the kid that lived across the street,
0:09:36 you know, which coffee shop you went to,
0:09:37 you go to the coffee.
0:09:40 And then the thing I do, which is a little psychotic,
0:09:44 but I do it anyway, is I want to be able to describe
0:09:47 what the, I want you to feel like it’s a novel
0:09:49 in some respects, but it’s all real.
0:09:50 Like nothing’s made up.
0:09:53 And so like, if I know he, let’s say he took a picture,
0:09:56 it was one instance where he went camping.
0:10:00 And, and so I didn’t know where the campground was.
0:10:01 It was near San Francisco,
0:10:04 but he’d taken two pictures, three pictures, sorry.
0:10:07 One was when he left and we could figure out the street
0:10:10 because we could, you know, see the angles
0:10:11 and the street signs.
0:10:13 The next was when he was driving over the Golden Gate Bridge.
0:10:15 And then the third was when he got to the campground
0:10:17 and we could tell the timestamps.
0:10:19 So we just did the math and we’re like, okay,
0:10:23 it’s probably 45 to 50 miles away.
0:10:25 And then we looked in the circle around San Francisco
0:10:26 and then we found these different campgrounds
0:10:29 and I went to one and there we are at the campground.
0:10:31 So I go there and I find the place
0:10:32 that he took the picture from where he’s sitting.
0:10:37 I sit in that spot and I can, I can smell the, everything.
0:10:39 And so I can describe that
0:10:42 because it hasn’t changed in six months or a year.
0:10:43 It still looks the same.
0:10:45 And, and so I do that with like everything.
0:10:47 I go to the coffee shops he goes to.
0:10:48 I walk the same street.
0:10:50 And so you get to describe this.
0:10:52 And then you also can look, you know,
0:10:55 with, with different apps where you can see the way
0:10:57 the sun comes on certain days
0:10:58 and you can describe what the shadows look.
0:11:00 And then you just can describe everything.
0:11:01 – Sam, isn’t this wild?
0:11:03 Like it’s wild in two ways.
0:11:08 One, it’s the same sort of obsession of why jobs is like,
0:11:09 I’m going to design.
0:11:11 We need to finish the inside of the casing of the computer.
0:11:13 And they’re like, Steve, nobody’s going to see this.
0:11:15 And he’s like, I’ve seen it.
0:11:16 I know it’s there.
0:11:19 That’s why we have to finish this, the inside case.
0:11:21 So this is a weird kind of product obsession,
0:11:23 which I respect.
0:11:26 But then there’s also like, dude, nobody would know.
0:11:27 Nobody would ever know.
0:11:28 And it might not ever matter.
0:11:29 Why does it matter to you to do that?
0:11:31 – Well, and it’s also weird that Nick, you’ve written
0:11:34 like hashing Twitter wasn’t the most favorable towards
0:11:36 like Jack Dorsey and some of these guys.
0:11:38 You guys all have the same flavor of crazy though.
0:11:39 You know what I mean?
0:11:42 Like that’s what Sean’s describing is like
0:11:43 what the greats have.
0:11:43 – Look, I totally agree.
0:11:45 Look, I mean, it’s, it’s fun for me.
0:11:47 I think it’s like, I, I love the challenge,
0:11:49 but it’s, what’s interesting, you can bring up jobs.
0:11:52 Like I spent, I spent quite a lot of time talking to him
0:11:55 when he was alive and he was incredibly obsessive.
0:11:59 And of course, and like, and, you know, one of the things
0:12:01 that he always said that, that in me said it publicly too,
0:12:05 but like, you should never know that the technology exists
0:12:07 and how it happens and so on and so forth.
0:12:10 And, and it’s, I’m fine coming on a podcast
0:12:11 and talking about how I did it.
0:12:13 But when you’re reading, I’m not going to tell you,
0:12:15 like there’s nothing that drives you more insane
0:12:19 where it’s like, according to a transcript that I found it,
0:12:20 it’s like, who gives a shit?
0:12:21 Like just tell me the story.
0:12:25 And like, and, and I think that I, you know,
0:12:28 one of the beauties of great products
0:12:31 is when you don’t know how it works.
0:12:33 And they, and, and I think one of the,
0:12:35 and it just works and it’s magical.
0:12:37 And it’s, you know, the, all those, those words that they use
0:12:39 in the, in the ads and everything.
0:12:41 And I think the same, the same is true for storytelling.
0:12:44 You, you know, like a lot of the greatest novels,
0:12:46 I, I, I’ve, I’ve, I’ve, I’ve, I’ve, I’ve read a ton of novels.
0:12:48 And, um, there are a lot of the greatest novels.
0:12:51 The, the amount of research that people like Gabrielle
0:12:54 and Garcia Marseille has put into a hundred years of solitude
0:12:56 and like, into chess.
0:12:58 It’s like, when you read these, they,
0:12:59 they’re not telling you all this,
0:13:00 they’re just telling you a story.
0:13:02 And why would, uh, I saw that you talk,
0:13:04 I think you said in another podcast,
0:13:07 you spent like three or four weeks with Julia Ross’s
0:13:09 ex-girlfriend when he was starting it.
0:13:11 And there are, and, and, and I didn’t know that you had
0:13:12 spent time with them when I was,
0:13:14 spent time with her because I was like, why, why on earth
0:13:15 did she ever talk to Nick? Like, you know,
0:13:18 if I’m her, I’d probably just kind of shut up.
0:13:21 But you knew stories like, you knew like when they had sex
0:13:23 or like, like the comments that they made to each other.
0:13:25 I’m like, how on earth does he know this?
0:13:28 And then I find out that you, I heard you spent time
0:13:30 with her like getting info.
0:13:32 Why on earth would some of these sources talk to you?
0:13:34 Why not? Why wouldn’t they just say,
0:13:36 I don’t need that in my life. Get out of here.
0:13:40 – I think, um, uh, one of the things I’ve learned
0:13:43 as a reporter for two decades is that people talk,
0:13:45 people want to talk for different reasons.
0:13:48 So, uh, you get, there’s, you know,
0:13:49 endless numbers of them.
0:13:53 And one of, one of, I think the thing,
0:13:55 people think being a reporter is like,
0:13:57 you got to break the news and you got to write the story.
0:13:59 It’s like, no, it’s a, it’s relationships.
0:14:01 It’s like, it is literally just relationships.
0:14:05 And, and what you have to do is you have to figure out,
0:14:06 you need these people to talk to you
0:14:09 and you have to figure out how to make them want to talk to
0:14:12 you. And so for example, everyone has a reason.
0:14:14 So people that would, would leak stuff to me
0:14:17 that worked at Apple or Facebook.
0:14:19 Some of them were so, just so excited to say,
0:14:20 oh my God, I worked on this thing.
0:14:22 And it was like, and they, and they just want it out there
0:14:24 and they don’t have the patience and you know,
0:14:26 and others of them worked on something that never got made
0:14:28 or they got fucked over by their boss
0:14:30 or they didn’t get the credit and like,
0:14:32 or like they have other, the egotistical reasons,
0:14:33 whatever it is.
0:14:37 And so your job as a, as a reporter is to try to get them
0:14:39 to talk to you and to try to figure out.
0:14:43 And my job is to be like, why, what can I say to you?
0:14:45 What is it that you want?
0:14:47 I know you want, we all want something.
0:14:50 And so with Julia, you know, I think,
0:14:54 I think she wanted, she wanted to be part of the story.
0:14:58 And I think she wanted to be famous a little bit.
0:15:01 And I also think that she, for her,
0:15:04 there were, there were some things that hadn’t been said
0:15:07 and haven’t been finished and that she hadn’t,
0:15:09 it was like a little bit cathartic I think in some respect.
0:15:11 And so that’s the reason she talked.
0:15:12 When it came to the agents, you know,
0:15:15 I spent time with all of the agents involved in the case,
0:15:17 well, almost all of the agents.
0:15:20 And, and, you know, with Jared Yegan
0:15:23 and I probably spent 400 hours, 500 hours together.
0:15:25 You know, we, I went to his office.
0:15:26 I went to his house.
0:15:28 I went to his, we, we met in all different places.
0:15:30 I saw the postal service where he worked
0:15:32 and we went inside the Chicago airport
0:15:35 and underneath the bowels of it.
0:15:37 I mean, it was amazing to see all this stuff.
0:15:38 Sean, do you remember that where,
0:15:39 so Jared was the guy who like,
0:15:41 he wanted to be an FBI agent or something like that,
0:15:43 but he ended up being a Homeland Security agent,
0:15:44 which is like, like,
0:15:45 I think the book starts with him.
0:15:47 It’s like, he’s discovered a pill.
0:15:48 Yeah, a single pill.
0:15:49 One pill.
0:15:52 And what shocked me about Homeland Security and mail
0:15:54 is that they would just sit there
0:15:56 and watch packages come in.
0:15:56 And they would just be like,
0:16:00 that envelope looks weird because like,
0:16:03 it’s handwritten in a certain way.
0:16:04 And it’s just similar.
0:16:06 Like, it’s just so crazy that one of the,
0:16:08 one of a few different ways that he was caught
0:16:12 was just like traditional police work,
0:16:14 as opposed to like something more complex.
0:16:18 It was shocking that it was just like eyeballing things.
0:16:22 Well, why I started with the pink pill,
0:16:24 the single solitary pink pill is because,
0:16:28 and then there’s a paragraph in the book
0:16:30 about how, you know,
0:16:32 the website started with a single line of code
0:16:35 and all of a sudden he creates this world and so on.
0:16:37 Is, I think what’s interesting about technology,
0:16:40 this was just me, the way I wanted to tell the story,
0:16:41 but what’s interesting about technology,
0:16:43 there’s also the scene where,
0:16:45 and I say scenes ’cause I think of them in my head as scenes,
0:16:48 they’re not chapters, like everything’s visual in my head.
0:16:53 And there’s this scene where we see a computer being built
0:16:55 and it starts with like a single diode.
0:16:58 And what I find so fascinating about technology
0:17:00 is all these websites and all these products
0:17:02 and all these companies, they start with this little,
0:17:05 this one thing and the same with the books and everything.
0:17:09 And they grow into these, they take over the world.
0:17:11 And so for me, the pink pill,
0:17:14 the single solitary pill of ecstasy
0:17:15 was the beginning of the story,
0:17:18 which was just gonna become a fucking tidal wave
0:17:20 that took over everything.
0:17:23 Did you ever feel in danger during your research?
0:17:25 I felt more in danger doing the Twitter book quite honestly.
0:17:28 (laughing)
0:17:31 What was the danger there?
0:17:33 The powers that he didn’t want.
0:17:35 Jack Dorsey did not want that book out.
0:17:36 And he was trying to do everything.
0:17:38 Dude, he’s a peace-loving hippie.
0:17:39 As far as I could tell,
0:17:41 he sits with a beard and a tie-dye shirt.
0:17:43 He just wants peace and love for all, I thought.
0:17:48 He, no, that is all a story that he tells.
0:17:50 Look, there are definitely stories I’ve worked on.
0:17:52 I wrote a book that didn’t,
0:17:55 I chose not to publish, it was just about the NRA.
0:17:58 This was after Marjorie Stone and Douglas had happened
0:17:59 ’cause I went to school there.
0:18:01 And it’s been a couple of years on the book
0:18:04 and then decided to not do it for a few reasons.
0:18:07 But that one, I wouldn’t even say that was,
0:18:10 I wasn’t afraid someone would come after me,
0:18:13 except maybe some gun nuts later.
0:18:15 You know, I’ve done some stories,
0:18:19 mafia stuff, like Russian hackers, things like that.
0:18:23 And I’ve never, you know, I think a lot of the times
0:18:27 that people respect the process
0:18:29 and they don’t want to start a war
0:18:32 with the New York Times or Vanity Fair or, you know,
0:18:34 I think it’s different if you’re like covering
0:18:37 Mexican cartels in, you know, in Mexico,
0:18:39 that’s a whole different thing
0:18:41 or if you’re trying to be a reporter in Russia
0:18:42 or something like that,
0:18:44 that’s where you really do have to start to worry.
0:18:46 But in Silicon Valley, it’s a bunch of nerds
0:18:50 that, you know, talk a big game and that’s it.
0:18:53 I did have, I do have one story,
0:18:54 but it’s from the Twitter book.
0:18:57 So when I, I won’t mention names here,
0:18:59 but when I wrote the Twitter book
0:19:00 and there’s a moment in the book
0:19:03 where someone gets fired.
0:19:06 And I got a call from a friend who’s a journalist
0:19:08 at Bloomberg and they said,
0:19:11 “Hey, somewhat there’s a bunch of people,
0:19:14 “these like crisis PR people that are trying to,
0:19:16 “they’re calling all the journalists
0:19:18 “that you just called me and they’re trying to say
0:19:20 “that your book is all fabricated and it’s not true.
0:19:22 “And this, especially this moment, it’s all made up.
0:19:24 “And I just wanted to let you know.”
0:19:27 And I was, so I just called this woman directly
0:19:31 and I was like, “Hey, I heard you’re calling everyone.”
0:19:32 And she’s like, “I didn’t say that.”
0:19:34 And I was like, I said, “Look, I have the tapes
0:19:37 “of the interviews of that moment.”
0:19:40 And I was like, “I will happily post it on Twitter.”
0:19:41 I said, “You just keep calling people
0:19:43 “and I’ll put it on Twitter.”
0:19:44 And that was the end of it.
0:19:47 So, you know, so there are these moments
0:19:48 where you get these crisis comms people
0:19:51 that come after you, but like, whatever.
0:19:54 – When you do as much research as you do,
0:19:55 you end up getting to know the subject
0:19:57 in some ways better than themselves.
0:19:59 It’s like in business, these CEOs will pay
0:20:02 for these expensive 360 reviews
0:20:04 where somebody goes and talks to their wife
0:20:07 and their co-workers and their interns
0:20:08 and they come back with this feedback
0:20:11 and it’s supposed to be this eye-opening thing about them.
0:20:13 This person can find out more about them
0:20:16 and show them a mirror that they haven’t really seen before.
0:20:18 In that case, they want it.
0:20:21 But you know, when you’re researching Jack Dorsey
0:20:22 and you say something like, you know,
0:20:25 that’s all the story, who’s the real Jack Dorsey?
0:20:29 – Well, I think just one thing about what you just said
0:20:31 is I know, somebody asked me once,
0:20:33 how do you know when your book is done?
0:20:35 When you’re like, when you’re ready to,
0:20:39 ’cause what happens is you research for a long time.
0:20:41 You don’t write a word until you’re ready,
0:20:44 until you’ve done all the research and you have everything.
0:20:45 And I have, in my office, I have these boards
0:20:49 and I create these cards that you can, you know,
0:20:50 where they’re just all the scenes
0:20:52 of different colors and everything
0:20:53 and put them up on a wall.
0:20:59 And I know that when I’m ready to write,
0:21:02 when I start telling the people I’m writing about things
0:21:04 they don’t know about themselves.
0:21:06 And that’s the moment when I’m like, okay, I got it.
0:21:08 And so that happened with the Twitter book.
0:21:11 I remember sitting with all the founders
0:21:13 and there was a moment where I told Evan Williams,
0:21:16 something that had happened behind his back
0:21:18 that I thought he knew about and he had no idea.
0:21:21 And I was like, oh, okay, well, there you go, I’m ready.
0:21:25 And, you know, as far as Jack specifically goes,
0:21:28 the best quote I ever got about Jack Dorsey
0:21:29 and I’ve written a lot about him
0:21:32 was from one of the board members years ago
0:21:35 who said the best product Jack Dorsey ever made
0:21:36 was Jack Dorsey.
0:21:42 Because it’s, because that’s what it is.
0:21:46 It’s a, everything is a story, right?
0:21:49 Every single solitary thing we do every single day
0:21:51 is us telling a story.
0:21:53 The outfit you chose to wear today
0:21:56 is a story about yourself, me telling a story
0:22:00 about the book is me, it’s all we’re doing all day long.
0:22:01 And we’re telling these stories
0:22:03 and we choose which story we want to tell certain people
0:22:06 but based on how they want us to perceive us.
0:22:09 And I think that people like Jack and Jobs
0:22:11 and Bezos, all of these guys in Zuck,
0:22:16 that’s one of the things they’re great at
0:22:17 is telling a good story.
0:22:21 And I think like I personally believe
0:22:23 that your story for a company
0:22:25 is more important than anything.
0:22:27 I don’t care if you have the greatest product in the world,
0:22:29 if you can’t tell a story about it,
0:22:31 well, what’s the point?
0:22:34 What’s the example that drives that home?
0:22:35 YouTube is a perfect example.
0:22:38 YouTube was not the first video platform.
0:22:40 There were dozens and I remember seeing this.
0:22:42 Like when I was just a beat reporter
0:22:44 covering Silicon Valley and I would,
0:22:46 my days were like, it was like office hours
0:22:48 and you’d have like startup after startup
0:22:51 in like 2009, ’11, ’12 come in and meet with you
0:22:53 and they would have, you know,
0:22:56 some of them have great ideas and,
0:22:57 but they couldn’t walk you through it
0:22:59 and they didn’t hire a PR person
0:23:03 and they didn’t like, and so, you know,
0:23:06 and YouTube, YouTube had a great story
0:23:09 and that they were able to tell and that became,
0:23:11 and it became the video platform.
0:23:13 There were other video platforms that were,
0:23:16 I would argue way better than YouTube.
0:23:17 And I mean, Vimeo is a perfect example.
0:23:21 Vimeo was a thousand times of a better product
0:23:25 and a prettier, easier to do, all these things.
0:23:27 And YouTube just told a great story
0:23:29 and Google helped them do that.
0:23:31 And it becomes, that’s what it becomes.
0:23:35 And if Jack Dorsey had told the real story about Twitter
0:23:37 that his best friend Noah Glass really was the one
0:23:40 that came up with most of it and he stole it, you know,
0:23:45 from him and like, and that place was a shit show
0:23:46 and no one knew what was going on.
0:23:47 It was all an accident.
0:23:49 Like, you’d be like, oh, okay.
0:23:53 But to tell the story that I am the next Steve Jobs
0:23:56 and I conceived of this idea of Twitter
0:23:58 while I was in my mother’s womb
0:24:01 and like, holy shit, I gotta check this thing out.
0:24:02 What is this?
0:24:03 And it’s like–
0:24:04 Yeah, like the Jack Dorsey Twitter story I know
0:24:07 is he grew up and he was just fascinated
0:24:09 with dispatch or something like that.
0:24:12 He talks about like, I loved either taxi dispatch
0:24:14 or some transportation dispatch service
0:24:16 he used to listen to in that short form.
0:24:19 Dispatch communication was always something he was into.
0:24:21 And then when had the, you know, the idea for Twitter
0:24:24 and he has the sketch of the original Twitter thing
0:24:27 that he posts, you know, he’s posted before.
0:24:29 That’s the story that I know, right?
0:24:30 Because I’m just the receiving end
0:24:31 of that product he’s created.
0:24:32 Yeah, so it worked, right?
0:24:34 That story, the story worked.
0:24:34 Is it true?
0:24:36 No, it’s not true.
0:24:38 Yes, he was interested in dispatch
0:24:41 in the same way he was interested in writing poetry
0:24:44 and painting his nails black and dyeing his hair blue.
0:24:45 Like, but that’s not part of the story
0:24:47 because what really happens
0:24:50 is, and as I say in hatching Twitter,
0:24:52 and no one knew this, I was like,
0:24:54 I had to talk to all these different people
0:24:55 to kind of pin it together
0:24:59 except no a glass knew it was, you know,
0:25:01 Jack was living in San Francisco.
0:25:03 He was in the early 30s.
0:25:06 He was like a part-time Manny in Oakland.
0:25:10 He, like his life had not turned out in any way,
0:25:12 like the predestined version of Jack Dorsey
0:25:13 we think of today.
0:25:16 He got a job working at a, you know,
0:25:18 the ticketing booths at Alcatraz.
0:25:21 So they’re these booths that are pretty small.
0:25:24 And he was the C programmer who would go
0:25:25 and fix the ticketing booths.
0:25:26 And the reason he got the job was
0:25:29 ’cause he was small enough to fit inside
0:25:30 the booth and program.
0:25:33 So this was the life he was living.
0:25:37 And he had went, he applied for a job
0:25:40 at camper shoes to sell shoes,
0:25:44 not like to build the website or be the CEO.
0:25:46 Like, and he couldn’t get the job
0:25:47 and he was at a coffee shop
0:25:48 and Evan Williams walks in
0:25:50 and he’d read an article about Evan
0:25:52 and he just felt like it was a sign,
0:25:52 which it probably was.
0:25:54 The universe was putting them together.
0:25:56 So he sent him a note and he said,
0:25:57 “I’m a programmer,” you know.
0:26:00 And they had Odeo at the time,
0:26:01 which was the podcasting company,
0:26:04 which was a decade ahead of its time,
0:26:06 which was a brilliant idea
0:26:09 that Noah Glass had come up with.
0:26:11 And so Noah and Evan Williams
0:26:14 had created this thing called Blogger.
0:26:18 And Blogger was again ahead of its time, you know,
0:26:19 and Google purchases it.
0:26:22 And one day this guy, Biz Stone reaches out
0:26:23 and he says, “I love Blogger.
0:26:24 I’d love to come work for you.”
0:26:29 And so Evan Williams and Biz become friends
0:26:32 at Jason Goldman, who’s also another part of this.
0:26:33 He’s working at Google.
0:26:34 They all kind of become buddies.
0:26:37 They end up leaving and will get Goldman stays.
0:26:39 But Evan, Biz end up leaving.
0:26:41 And the reason that they leave is because Evan lives on,
0:26:43 I think it was like 18th and market
0:26:45 or whatever the streets were.
0:26:48 And he, one day he was on his balcony
0:26:52 and another guy, Noah Glass, was on his balcony.
0:26:54 And Noah had been reading that same article
0:26:56 that Jack Dorsey had read.
0:26:58 And he recognized in the article
0:27:02 that the photo of Evan, of Evan Williams
0:27:03 was taken on the balcony.
0:27:06 And in the background, there’s a little Noah Glass
0:27:08 because they were neighbors.
0:27:10 And so he goes out and he goes, “Hey, Blogger.”
0:27:11 And they become friends.
0:27:13 And then he pitches in,
0:27:17 Noah pitches in this idea for this podcast company.
0:27:18 He’s like, “This is the future.
0:27:20 It’s going to take over radio and so on.”
0:27:22 And so Evan is like looking for a project.
0:27:23 And so he agrees to do it.
0:27:25 It’s all discombobiliated.
0:27:26 No one knows what’s going on.
0:27:28 Like they can’t run the startup.
0:27:30 Apple comes along with podcasts, they’re screwed.
0:27:34 Jack Dorsey comes along and they do a hack day
0:27:38 and to try to like last hurrah to save the company.
0:27:41 And they, during the hack day,
0:27:44 Jack presents this idea for status, okay?
0:27:47 And everyone’s kind of doing the same thing.
0:27:49 The ideas are very, very similar.
0:27:50 And I’ll tell you a couple of them.
0:27:52 But Jack presents this idea for status.
0:27:57 And what status is stat.us/nickbilton, right?
0:28:00 And you go there and you see my status.
0:28:01 It’s one status.
0:28:03 So if I say, and it’s three, four words,
0:28:05 you’re not really supposed to do anything more than that.
0:28:07 On a podcast.
0:28:08 Now, if you go an hour from now,
0:28:12 if I put it post a new status and I’m like taking a walk,
0:28:13 the on a podcast is gone.
0:28:15 And it now just says taking a walk.
0:28:16 It’s like an AM away message.
0:28:19 It’s literally an AM away message that they were doing.
0:28:24 And so Noah has a very similar idea.
0:28:30 But Noah’s like, no one is going to go stat.us/nickbilton,
0:28:33 five times, your mom will do it
0:28:34 ’cause she wants to know what you’re up to.
0:28:36 But no one else is doing that.
0:28:39 And so they all start bringing these ideas together.
0:28:40 And it’s truly, it’s like 11 people in the room.
0:28:43 It is a collaboration between all of them.
0:28:45 And what Noah has this realization
0:28:49 is he’s a very emotional guy, very smart.
0:28:51 And he’s like, it needs to be about friendship.
0:28:54 It needs to be about connecting with your friends.
0:28:55 And that is what it’s about.
0:28:58 And so he brought this humanity to it.
0:28:59 And so he came up with the stream.
0:29:01 And the, it’s like all, not the replies,
0:29:04 but the friends like that you had friends and you,
0:29:06 and that was what, that was Twitter.
0:29:08 It wasn’t status, you know?
0:29:11 There were a million other statuses back then.
0:29:16 I mean, and so when it ends up becoming what it became,
0:29:17 Noah was a mess.
0:29:18 He was getting divorced.
0:29:21 He was like, his life just wasn’t work.
0:29:24 And he gets pushed out by Jack and Eve.
0:29:26 And Jack, who his best friends would know,
0:29:27 it goes into Eve’s office one day.
0:29:30 And he says, “Either you get rid of Noah or I quit.”
0:29:32 And as far as Eve knew,
0:29:34 Jack had come up with the idea himself, you know,
0:29:37 when he was a little kid listening to fire trucks.
0:29:39 That was a story that was added later.
0:29:44 And so, you know, so, but that’s,
0:29:46 but the better story is not,
0:29:48 oh, I screwed over my best friend
0:29:50 for power and control of this thing.
0:29:52 It’s when I was a kid,
0:29:54 I used to sit in my room at 12 years old
0:29:55 and I had the vision for Twitter
0:29:56 by listening to fire trucks.
0:29:58 Okay, that’s a great story.
0:30:01 And so, you know.
0:30:03 You seem like you don’t like Jack Dorsey.
0:30:04 Is it, you don’t like him
0:30:06 or you just feel like that’s a wrong
0:30:07 that needs to be righted to that story?
0:30:09 Is that you want to trust the record?
0:30:12 That is, I don’t like people who fuck other people over,
0:30:14 especially their friends.
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0:31:02 All right, back to the episode.
0:31:05 – Did you find yourself,
0:31:08 like you had this great podcast with our friend David Perrell
0:31:10 and you set a line that Hitchcock,
0:31:12 someone came up with where it was,
0:31:14 every villain has a mother.
0:31:17 And it was like, I guess like you see yourselves
0:31:18 in the villain at times.
0:31:19 That’s what a good story is to do.
0:31:21 You kind of like a villain a little bit
0:31:24 or they’re a little, you know,
0:31:26 you’re interested in them.
0:31:28 Did you find yourself liking Ross?
0:31:30 Did you find yourself liking Jack at times?
0:31:32 Like, because you get so into their minds
0:31:35 and you also see that like,
0:31:36 even though they do a lot of bad things,
0:31:38 they do a lot of epic things, a lot of big things,
0:31:41 do you find yourself admiring and liking them?
0:31:43 – Well, they all have a charisma to them, you know,
0:31:47 that you can’t pull this off without the charisma.
0:31:50 I met Trump, he’s very charismatic,
0:31:52 very, very charismatic.
0:31:53 You’d like want to be around him,
0:31:55 even if you don’t agree with him.
0:31:56 – What was the context, how’d you meet him?
0:32:00 – Oh, just at a rally once years and years and years ago,
0:32:02 I think 2015 or something like that.
0:32:03 You know, spent time with Elon.
0:32:05 Like he’s kind of funny, he’s funny.
0:32:08 He’s like a weird dude, but he’s funny, you know.
0:32:11 Jobs had this like aura to him, you know, bezos too.
0:32:13 Like they, funnily enough,
0:32:15 Zuck doesn’t necessarily have the charisma,
0:32:16 but it’s almost like he’s a robot
0:32:18 and you’re like, oh, how does this thing work?
0:32:20 (laughing)
0:32:23 But they all have this,
0:32:28 there’s something to them that is enticing.
0:32:31 And Jack’s funny, he’s a funny, nice guy.
0:32:32 Like when you’re hanging out with them,
0:32:35 it’s like you’re like, oh, he’s fun.
0:32:36 I like hanging out with this guy.
0:32:40 And so, and I never met Ross.
0:32:42 I covered him in the court in the trial.
0:32:46 So I saw him many, many times, but never spoke to him.
0:32:48 And, but they have this charisma to them
0:32:51 that I think makes them great in some respect.
0:32:53 And it’s not something that you can learn.
0:32:56 It’s just something that you either have or you don’t have.
0:33:01 And so you cannot help but like them for that.
0:33:05 But I think for me, I just, I don’t understand.
0:33:06 Here’s the part with Jack
0:33:08 and then we should move on from it
0:33:10 because I could talk all day about this,
0:33:15 but Jack is worth $12 billion, give or take.
0:33:22 Noah Glass is worth about $0, okay?
0:33:25 He never got anything.
0:33:29 He gave him something and he had to live off that and whatnot.
0:33:33 If you’re worth $12 billion, give the guy $10 million.
0:33:34 You wouldn’t even notice.
0:33:36 It would literally be like losing a penny
0:33:38 between your couch cushions.
0:33:40 And like that to me,
0:33:42 even if you believe that you are the creator,
0:33:44 even if you believe that,
0:33:46 that you really came up with this on your own
0:33:48 ’cause he may believe that today,
0:33:50 I just don’t understand like why the kid
0:33:51 that you were best friend,
0:33:52 the guy you were best friends with
0:33:56 who without question helped you with this product.
0:33:59 Like go take care of him and it never happened.
0:34:00 And for me that-
0:34:01 – Well, Noah Glass, I agree with you,
0:34:03 but also Noah Glass now has a thing too, right?
0:34:05 Doesn’t he have Olo or-
0:34:06 – No, that’s a different Noah Glass.
0:34:08 – No shit, they’re not the same guy?
0:34:12 – Not the same guy, so everyone thinks that.
0:34:13 – I thought they were the exact,
0:34:15 I thought it was like his second coming.
0:34:18 – No, he’s, he just, he has a family
0:34:20 and he like, he married this French woman
0:34:22 and they have two kids and I think they-
0:34:23 – Dude, not only Twitter got stolen from him,
0:34:24 his own name got stolen,
0:34:27 his own name space on Google got stolen from him too.
0:34:28 – Let’s go buy the other guy.
0:34:29 – Mess him up.
0:34:30 – I did not know that.
0:34:33 I thought it was like, oh, he’s getting it back.
0:34:34 – No.
0:34:36 – Oh man, that ruined the story for me.
0:34:40 – Can you tell us some other stories of,
0:34:41 that have stood out to you?
0:34:43 Things you still remember, either experiences or whatever.
0:34:45 You said like, I got job stories.
0:34:46 I have Zuck stories.
0:34:48 I have Elon stories.
0:34:51 – Let’s see, jobs is the best one I think.
0:34:53 I’ll do the job story.
0:34:56 So when I was a reporter at the times,
0:34:59 I didn’t really know what I was doing.
0:35:01 Like no one knows what you’re doing
0:35:03 when you start out in these jobs.
0:35:04 You pretend you do, but you don’t.
0:35:07 And I don’t even think,
0:35:09 I think the 10,000 hours is nonsense.
0:35:10 I think it’s about 30,000, right?
0:35:13 To really understand what you’re doing properly.
0:35:17 But I was at the times and I was,
0:35:18 and what had happened was,
0:35:22 I come into the times by complete accident.
0:35:25 Let me just start with that story
0:35:26 ’cause it’s actually a very funny story.
0:35:29 So I was, my dream job was,
0:35:31 I wanted to be a war photographer.
0:35:33 And I’d read all these war photography books
0:35:37 and I saved up and bought like a fancy camera.
0:35:39 And I would like to practice war photography
0:35:41 with my friends where they would like,
0:35:44 run through the streets and I would take pictures.
0:35:47 And so I put together this portfolio
0:35:49 and I was a graphic designer.
0:35:52 And I’d done toy package design for a while.
0:35:54 And I’d like designed the verse Britney Spears doll
0:35:56 and stuff like that.
0:35:58 And so I was like, oh, I can use the designer job
0:36:00 to get to the times as a designer.
0:36:02 And then I can become a war photographer.
0:36:05 And so I end up doing that.
0:36:08 I’d do page layouts and stuff like that.
0:36:10 And when you do these, the way these meetings work
0:36:14 is these newspapers, you have a morning meeting
0:36:17 where all the editors and reporters go in one big room
0:36:19 and each section, the business section,
0:36:21 the culture section, the front page and so on.
0:36:23 You pitch, they pitch their stories,
0:36:25 the editor decides which is gonna go where
0:36:27 on the front page and off you go.
0:36:28 But I would always speak up
0:36:30 ’cause I didn’t know you weren’t supposed to.
0:36:31 And so I’d be like, well, what about this?
0:36:32 And what about that?
0:36:32 And I like that.
0:36:33 And what if you did this?
0:36:37 And I just became like friendly with a lot of the editors.
0:36:39 And one day I sit down with the photo editor
0:36:41 and I show her my photos.
0:36:43 And she looks to her name was Michelle McNally.
0:36:46 And she like slowly goes through one by one.
0:36:47 And she closes the book and she goes,
0:36:49 she’s like, you’re a good photographer.
0:36:51 She’s like, I think you’d be a good war photographer,
0:36:53 but I’m not gonna hire you to do it.
0:36:53 And I was like, why not?
0:36:55 And she goes, because you’re too normal.
0:36:57 She’s like, these guys are fucked up.
0:36:58 They’re on drugs.
0:37:02 They can only be in a war zone half the time.
0:37:05 Like they’ve just got something that’s missing
0:37:07 that they need that adrenaline.
0:37:09 And she was like, I don’t feel that from you.
0:37:12 And I’m grateful, so grateful that she said that.
0:37:15 And so I was like, well, what do I do now?
0:37:20 And at the times, I’d become friends with Marissa Mayer
0:37:23 and I was talking about going over to Google
0:37:25 to go to Google News.
0:37:27 I mentioned this to the editor-in-chief
0:37:29 of the business section.
0:37:31 And he said, oh, God, I wish we could keep someone
0:37:32 like you to be like a reporter
0:37:35 because everyone wants to write for the print section.
0:37:38 No one wants to write for the web.
0:37:40 And I just, the words just came out of my mouth.
0:37:41 I’d never wanted to be a writer.
0:37:44 It had never been anything on my list
0:37:45 of things I wanted to do.
0:37:47 And I said, well, I would do it.
0:37:49 And he was like, oh, well, why don’t we try it?
0:37:52 And then I was like, oh, shit, what have I done?
0:37:56 And so the first day, I’m on the job at the New York Times.
0:37:57 And I’m in this massive newsroom
0:38:01 with all these insane people that, you know,
0:38:04 back then you were just like enamored by these buy lines
0:38:05 that you would just like, holy shit.
0:38:07 And my editor comes over and funnily enough,
0:38:09 it was Twitter had gone down.
0:38:10 And he said, Twitter’s gone down.
0:38:11 Can you write a blog post about it?
0:38:14 You know, call the company and everything.
0:38:15 And I was like, yeah, yeah, no problem.
0:38:17 And so I looked at my computer and I Googled,
0:38:19 how do you write a blog post?
0:38:23 So that was my first, and then I realized like,
0:38:25 oh my God, what have I done?
0:38:27 I found myself in this job
0:38:29 that I just don’t know what to do.
0:38:34 And so I spent weeks just reading every buy line
0:38:36 of the greatest reporters.
0:38:38 And I was like, okay, this is how they write the intro.
0:38:39 This is how they do the quotes.
0:38:41 This is how they do the nut graph.
0:38:44 And I just figured it out and I made mistakes,
0:38:47 but like that was my foray into it.
0:38:51 So one day about, I don’t know,
0:38:54 six months a year into me being a tech blogger
0:38:58 for the times I reach out to Apple as you call
0:38:59 and you say, hey, I’m doing the story on this.
0:39:00 Do you have a comment?
0:39:04 And the PR woman that answers,
0:39:07 she says, Steve’s gonna call you.
0:39:09 And at the time there was a guy called Steve Dowling
0:39:11 who was like a very senior comms person.
0:39:13 And I was like, oh cool, Steve Dowling.
0:39:14 And she goes, no jobs.
0:39:15 And I was like, what?
0:39:18 And I was like, is that normal?
0:39:19 Does that happen?
0:39:20 And she goes, sometimes he’s gonna call you,
0:39:21 wants to talk to you.
0:39:23 And I’d been writing a lot of Apple stuff.
0:39:26 And so he never called.
0:39:28 And that night I went out for dinner
0:39:30 with my girlfriend at the time.
0:39:34 And then we went for sushi and I had a few Sockies.
0:39:36 And then all of a sudden I get a phone call
0:39:41 from this number in San Jose and I answer it and it’s jobs.
0:39:43 And I was like a little tipsy.
0:39:44 And he talked to me for like an hour
0:39:48 and he just convinced me not to do the stories
0:39:49 in the way I did it.
0:39:52 And I didn’t, it didn’t make any sense,
0:39:54 but he made so much sense.
0:39:56 And he just, he was like, oh, well,
0:39:57 you got this wrong and that.
0:39:59 And then if you actually, if you look at this,
0:40:01 you can, and then the next day.
0:40:03 So I wrote the piece and then a couple of days go by,
0:40:05 you know when like you’ve seen a movie
0:40:07 and then all of a sudden you process the movie.
0:40:09 And then it’s like, oh, that makes sense.
0:40:12 I played this conversation back in my head.
0:40:14 And I was like, holy shit.
0:40:15 He convinced me not to do the story.
0:40:17 That was the right story.
0:40:18 He got you.
0:40:19 He got me.
0:40:21 And so John Markoff, who was a veteran reporter,
0:40:23 I told him and he goes, he just says,
0:40:25 it’s the reality distortion field.
0:40:26 And I was like, what’s that?
0:40:28 And he goes, jobs invented it.
0:40:32 And every time, I would talk to him from time to time
0:40:33 and every time it was the same thing.
0:40:34 It was like this.
0:40:38 He had this ability to make you believe
0:40:41 that what you were doing was not the right story
0:40:42 and that this was the way to do it.
0:40:45 It was, it was a really fascinating thing to see.
0:40:46 – How does the reality distortion,
0:40:47 ’cause I’ve heard that so many times,
0:40:50 the reality distortion field, never been in it.
0:40:52 You’ve been in it.
0:40:54 What is he actually doing in your opinion?
0:40:56 You’re a smart guy, you’re a storyteller,
0:40:57 you’re a persuasive guy,
0:40:59 you’ve been around other charismatic people.
0:41:01 Is it just his aura?
0:41:01 Is it his gravitas?
0:41:03 Is he really good at reframing things?
0:41:06 Is it, is it an intimidation?
0:41:07 What is he actually doing?
0:41:08 – And it’s one of those things that you hear about
0:41:10 and you’re like, that won’t happen to me.
0:41:11 – No, exactly.
0:41:15 I was, yeah, like he,
0:41:16 it’s hard to describe what he’s doing
0:41:21 ’cause it’s so interesting he convinces you
0:41:26 that you’re wrong and you believe it, you know?
0:41:31 You, and look, I think there’s a part of Jobs
0:41:35 that we should all admire and respect
0:41:38 and be really amazed by.
0:41:41 But there’s a part of him that he was,
0:41:42 he could be a real asshole.
0:41:45 Like Walter Isaacson told me this story once.
0:41:48 Jobs was, he presented the iPad
0:41:50 and then what they did back then,
0:41:52 they don’t do it anymore as much
0:41:54 because the media has changed so much.
0:41:56 But what they did back then was they would go around
0:41:58 to all the newsrooms around the country
0:42:00 and they would meet with the editorial boards
0:42:03 and the reporters off the record in total private
0:42:06 and they would show you the products that they were doing.
0:42:09 So, and presidents would do it too.
0:42:11 And, you know, you would sometimes get invited.
0:42:12 They’d be like, you know, Bush is here
0:42:15 or the secretary of state like come in.
0:42:16 It’s a huge, at the New York Times,
0:42:19 it was this massive conference room
0:42:21 and on the walls were all these photos
0:42:22 of all the dignitaries that had come
0:42:26 over the last 150 years and business people and so on.
0:42:28 And so we got a call that Jobs was coming.
0:42:31 And there was 20 of us that were invited to this thing.
0:42:34 And I ended up getting sat next to Brad Stone
0:42:36 who now runs Bloomberg business
0:42:38 and Jobs was right next to him.
0:42:40 And Brad was the Apple reporter at the time
0:42:42 and I was the tech blogger.
0:42:44 And there was this moment where he passes,
0:42:46 he brings an iPad prototype
0:42:48 and, you know, we’re playing with them and everything.
0:42:51 And I was prodding it too hard and he was like, stop it.
0:42:52 You’re hitting it too hard, Nick.
0:42:54 And I was like, okay.
0:42:55 And so, but then he says,
0:42:57 this is another reality distortion field.
0:42:58 This actually will make more sense.
0:43:02 He says, we’re doing questions and answers and everything.
0:43:05 And then I said to him, I said, Steve,
0:43:09 I saw you a couple of years ago at Cupertino
0:43:12 and you were sitting on, there was three stools on stage
0:43:14 and you were on one of the stools
0:43:17 and you were just presented the Apple television box.
0:43:21 And I said, you said that you see Apple
0:43:26 as having these three businesses, right?
0:43:28 There’s the Mac and there’s the iPod
0:43:30 ’cause that’s what it was back then and whatever.
0:43:33 And I said, and then you said Apple TV will be the fourth lag.
0:43:36 So the stool will become a chair, something like that.
0:43:39 And I remembered it verbatim back then.
0:43:41 And he goes, I never said that.
0:43:44 And I was like, no, you said that.
0:43:45 I’m pretty sure you said that.
0:43:47 And he goes, I never said that.
0:43:49 He goes, I’ve never said that about Apple televisions
0:43:50 that experiment for us.
0:43:51 We’re just playing with it.
0:43:54 It’s like, ’cause it wasn’t doing very well at the time.
0:43:54 And that was my question.
0:43:55 It was like, it’s not doing very well.
0:43:58 Like, did you say that incorrectly?
0:44:00 And I was like, and I’m sitting there
0:44:05 with all the editors and the big maccas at the New York Times.
0:44:08 And I’m like, and I’m just like this young reporter.
0:44:10 And I’m like, no, you definitely said that.
0:44:13 And he goes, Nick, I never said that.
0:44:15 And I was like, okay.
0:44:17 And so, and then I just like shut up.
0:44:20 And then afterwards, John Markov was there again too.
0:44:23 I pulled it up on my computer and I was,
0:44:23 and I watched the video.
0:44:24 I was like, he said it.
0:44:27 And he goes, reality distortion field.
0:44:27 And that was just it.
0:44:29 And so what was I gonna do?
0:44:31 Go run around to the 20 people in that room
0:44:32 and tell them to say that he made it up.
0:44:35 No, he did what he did and it worked.
0:44:37 And they all believed that that was just an experiment.
0:44:38 Right.
0:44:40 (laughing)
0:44:41 Are there any of these guys
0:44:43 that you felt like had it all?
0:44:46 Meaning they have the extreme success.
0:44:50 They’re the extreme achievers of society.
0:44:51 But, you know, most of the time you look
0:44:53 and they’re on their fifth wife
0:44:55 and they’re kind of the stories
0:44:57 that they’re kind of an asshole to work for
0:44:59 or that they screwed somebody over or whatever, right?
0:45:01 Like they have the same as this quote,
0:45:02 you know, show me a great man
0:45:03 and I’ll show you a bad man, right?
0:45:07 Like, you know, there’s this stereotype with that.
0:45:08 Was there anybody you met that you were like,
0:45:11 no, this person’s actually, they had it.
0:45:12 They had the career success,
0:45:14 but they also were a good family man
0:45:16 or they were actually good to be around.
0:45:18 They’re a good human being to be around.
0:45:20 Yeah, people who you would say they’re winning.
0:45:21 Yeah.
0:45:24 There was one person, and I say was.
0:45:26 There’s two, there are other people.
0:45:28 Look, I think like there are really good people
0:45:29 that in Silicon Valley,
0:45:32 they’re not the most successful of like, you know,
0:45:34 they’re not worth the hundreds of billions.
0:45:35 Like, I love Aaron Levy.
0:45:38 I think he’s a great guy, like Dennis Crowley, you know,
0:45:41 along with people that I really, really admire and like
0:45:43 and I think are good people.
0:45:47 But there was one person that I was like, oh, you have it all.
0:45:50 And I had met him because I had done these series of stories
0:45:54 on the Kindle and it was Jeff Bezos.
0:45:56 And I remember spending time with Bezos
0:46:00 and when I became a columnist at the New York Times,
0:46:02 like when I got promoted to be a columnist,
0:46:05 there was a guy, I worked with David Carr,
0:46:08 who was just a wonderful, wonderful human being
0:46:11 who was the media columnist.
0:46:12 And he since passed away,
0:46:15 but he was like, he was everyone’s mentor.
0:46:16 He would make time for anyone.
0:46:19 He was just a lovely, lovely person, so smart.
0:46:20 And when I became a columnist,
0:46:22 I didn’t the first few columns I wrote, I was like,
0:46:23 I don’t know what the hell I’m doing.
0:46:26 And David used to smoke outside
0:46:28 and I would go down on the King Island with him.
0:46:31 And he said, pick a fight that you can win.
0:46:34 That’s what you need to do the first time
0:46:36 when you first become a columnist.
0:46:38 So I was flying out to LA for Thanksgiving
0:46:41 and I was reading a book on my Kindle back then.
0:46:45 It was like 2010 and nine, 11, 12.
0:46:47 And I was reading a book on my Kindle.
0:46:48 It was like three pages to go.
0:46:50 And I was like, oh my God.
0:46:53 And they were like, you must turn off your devices off now
0:46:55 and put them in air flow mode and whatever.
0:46:59 And I wanted to finish, so I was like hiding the book
0:47:00 so I could finish it.
0:47:01 And the stewardess was like,
0:47:03 we are not allowed to take off sir until you turn it off.
0:47:05 And I was like, it’s a calculator.
0:47:08 Like it’s not gonna destroy the plane.
0:47:10 And she got very terse.
0:47:14 And I was so angry that when we finally got up to altitude,
0:47:17 I wrote a column about just how ridiculous it was.
0:47:20 And it got published like the next day, whatever.
0:47:21 And it was like the most red thing
0:47:24 on the New York Times for weeks.
0:47:26 And I was like, oh, I’m picking this fight.
0:47:29 And so I started doing,
0:47:30 I went to all these testing facilities.
0:47:32 ‘Cause back then you were allowed,
0:47:33 there were rules in the FAA.
0:47:36 You could use a razor, a tape recorder,
0:47:38 a heart monitor and some others.
0:47:38 So we got all these things.
0:47:40 – Sean caused it going to Petticourt.
0:47:43 – Yeah, he took over Petticourt.
0:47:44 – Yeah, I was in Petticourt.
0:47:46 And so we went to these testing facilities
0:47:49 and we did like EMP testing and we put a Kindle.
0:47:50 It’s amazing.
0:47:52 These giant rooms that like,
0:47:54 and you just have a device and they can test all the EMPs.
0:47:56 It turns out like the razor puts off
0:47:59 like a hundred times more EMPs than a Kindle.
0:48:02 And so I just kept writing these stories
0:48:05 ’cause people like were so irate about the fact
0:48:06 that they couldn’t read their Kindle
0:48:08 or play on their phone while they were taking off.
0:48:10 And eventually it got overturned.
0:48:14 And Bezos during his earnings call that quarter
0:48:16 was like, on the earnings call was like,
0:48:18 I want to give a shout out to Nick Bilton for like,
0:48:20 ’cause it helped his business, of course, you know?
0:48:24 And anyway, I ended up meeting with him
0:48:29 and he was like so smart and thoughtful
0:48:35 and just you could tell was on a different level.
0:48:36 Like you could just see like,
0:48:40 oh, this is someone who never forgets anything.
0:48:43 And he was married, he was talking about his kids
0:48:46 and how his teenage son still sits on his lap.
0:48:48 And like, and then I ended up going to a dinner
0:48:52 at his house and he was talking about his family
0:48:56 and like, and I met his wife Mackenzie many times
0:49:00 and I was like, oh, this, he’s the guy who has it all.
0:49:03 He’s like created this unbelievable business.
0:49:07 He doesn’t, from what I could tell, he’s not like,
0:49:09 people don’t say he’s an asshole to work for, right?
0:49:11 I’m sure there were some, but most people
0:49:12 like really, really loved working for him
0:49:15 and stayed at Amazon for years and loved the culture.
0:49:17 And then, and then they got divorced
0:49:20 and he ended up in a very, very different relationship.
0:49:25 So I, and now you like, he’s like this bodybuilding,
0:49:27 looking like raver.
0:49:29 So I think he had it all, but whatever reason
0:49:31 he had like this midlife crisis
0:49:33 that made him throw it all away.
0:49:34 I don’t know.
0:49:35 (laughing)
0:49:36 I don’t know.
0:49:39 So that was the one person that had it all.
0:49:41 – I want to talk about one more thing.
0:49:42 – Do you want me to tell that Walter Isaacson story?
0:49:45 – Oh, yeah, yeah, go ahead, go ahead.
0:49:47 So Walter told me this story of after the iPad
0:49:51 where he had met Jobs in the four seasons,
0:49:53 I think it was, which is connected to the,
0:49:58 the Musconi Center and they’d met for breakfast.
0:50:00 I don’t know if it was before or after the iPad.
0:50:04 And Jobs had ordered a fresh squeezed orange juice
0:50:06 and the waitress brings it out.
0:50:08 And it’s not fresh squeezed, it’s got like pulp in it.
0:50:10 And he calls her back over and he says,
0:50:13 “I asked for a fresh squeezed orange juice.”
0:50:15 And she brings another one out.
0:50:16 Again, that’s got pulp in it.
0:50:19 And he just becomes more and more angry
0:50:21 and about this orange juice.
0:50:24 And at one point, it stands in this,
0:50:26 she’s almost in tears, it’s like this, this poor waitress.
0:50:32 And at one point, Walter says like,
0:50:33 “Steve, what are you doing?”
0:50:34 Like it’s just an orange juice.
0:50:36 Like she’s, like she clearly doesn’t,
0:50:39 they clearly don’t have like non pulp orange juice
0:50:41 ’cause it’s fresh squeezed, whatever.
0:50:45 And he says, if she’s chosen to be a waitress for her living,
0:50:47 then she should be the best waitress she can be.
0:50:49 And it’s my job to push her to do that.
0:50:52 And it’s like, no, you don’t know her backstory.
0:50:55 You don’t know like where her life has gone
0:50:57 and why and things like that.
0:50:59 And like, and I think that like,
0:51:02 so for all the brilliance, there was a lack of compassion.
0:51:05 And look, we all, I think the thing is the reality is like,
0:51:06 none of us are perfect, we’re all good.
0:51:08 Yeah, well, do you think you have that?
0:51:10 You’re one of the best there is.
0:51:11 Do you lack that compassion?
0:51:13 I mean, like, are you accused of being an asshole?
0:51:16 Yeah, I fucking love when people call me an asshole.
0:51:18 Like I just like, I just don’t give a shit.
0:51:22 But like, what I pride myself on is,
0:51:26 I pride myself on being very, very easy to work with.
0:51:28 Like if we’re doing a creative,
0:51:30 if we’re writing a movie together
0:51:31 and I’m working with the producers
0:51:32 or we’re doing a documentary,
0:51:36 like I am there to make this the best possible.
0:51:39 And I will never, ever, ever be an asshole.
0:51:42 And you could never find anyone that would say I would
0:51:46 because I understand that what we’re doing is really hard
0:51:48 and we’re all doing our best.
0:51:51 And like, that’s the pursuit of creating great creativity.
0:51:54 However, I’ve picked fights with people
0:51:57 as a writer and a journalist and gone after people
0:52:00 that makes me into a fucking asshole, quite honestly.
0:52:02 You know, like I had that thing
0:52:06 when Dave Moran was doing, you know,
0:52:09 all of his products and startups.
0:52:12 Like I went after him and then later,
0:52:13 I actually later apologized to him
0:52:16 ’cause I felt like I was too much of an asshole
0:52:18 and we had like a heart to heart about it.
0:52:22 And like, and I do think like, there’s a great line
0:52:23 that Bill Keller, he was the editor in chief
0:52:25 of the New York Times for many years used to say,
0:52:26 and he used to say,
0:52:28 I don’t believe people should be able to write
0:52:29 about other people until they have been written
0:52:31 about themselves.
0:52:32 And I learned that when I,
0:52:34 people started writing stories about me
0:52:35 and it was like, oof, that feels awful.
0:52:37 Like that sucks.
0:52:39 And it was like a moment where I realized like,
0:52:42 oh, like I don’t need to be such a dick to people.
0:52:46 Like I can write these stories and I can be honest
0:52:47 and I can tell the truth,
0:52:49 but I need to, you need to have some compassion too.
0:52:50 And I, you know,
0:52:51 that was something I had to learn
0:52:52 at the beginning of my career.
0:52:57 – All right, Shawn here with a quick public service
0:53:00 announcement for any tech founders out there.
0:53:03 You know, listen, getting customers is your number one
0:53:04 priority and to land bigger customers.
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0:53:08 is that big customers need you
0:53:11 to pass security compliance checks.
0:53:13 That’s how you can bring in some of the big contracts,
0:53:14 but they take time and energy.
0:53:16 And one of the things I’ve seen over and over again
0:53:18 is a startup tries to do this all on their own.
0:53:19 They meet a customer,
0:53:22 the customer asks them about their SOC2
0:53:25 and then they start shifting their whole dev team over
0:53:27 to working on this and their features grind to a halt.
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0:54:03 All right, back to this episode.
0:54:05 (upbeat music)
0:54:08 You talk about like your time at the New York Times
0:54:10 where you’re like, we were in this room
0:54:12 and then the room had the portraits of all the important
0:54:14 people who used to come to us
0:54:16 and try to tell us what they were doing
0:54:17 because we were the messengers
0:54:19 and we used to kind of shape the narrative out there
0:54:21 and they tried to shape us and we shape the narrative.
0:54:24 And there was these people who were,
0:54:25 you recognize their names from the bylines
0:54:28 that you had just like so much respect for them.
0:54:31 Do you think that that’s still like,
0:54:33 does that shit matter at all anymore?
0:54:35 Because for me, I’m like,
0:54:36 if I’m a founder of a company now,
0:54:39 I don’t, I put $0 in the PR,
0:54:42 I put zero care and if I can get a press mention,
0:54:43 it’s like so low on the total,
0:54:46 compared to how it was 15 years ago
0:54:47 when I was building a company,
0:54:51 that has changed my respect for kind of mainstream.
0:54:54 I think Trump really like reality distorted everybody
0:54:56 when he started going after fake news,
0:54:57 and then he started seeing examples of it.
0:55:00 And like, I just feel like the credibility has gone down
0:55:02 but I’m also on the outside.
0:55:04 You’re almost, you know, you’re from that world.
0:55:05 Do you feel the same way
0:55:08 or do you think that’s completely misguided?
0:55:09 There’s a practical thing of like,
0:55:11 you can get an audience on Twitter or wherever
0:55:14 and you’re like, I don’t want you nor do I need you.
0:55:18 There’s two answers to that question.
0:55:20 And the first answer is that,
0:55:23 I think 90% of the media is utter garbage
0:55:27 and it is complete and utter ridiculous drizzle
0:55:31 that is opinionated and bad for society.
0:55:33 And I think 90, I think 10% is people
0:55:36 that are working really, really fucking hard
0:55:40 to try to do investigative reporting because they care.
0:55:41 And I met those people.
0:55:43 I remember those people at the New York Times
0:55:45 when I first started and I had, they were, you know,
0:55:48 they were people that were making 120 grand a year
0:55:51 and that could be making millions,
0:55:52 like working for a hedge billions.
0:55:54 I don’t know, like wherever they wanted
0:55:59 and they wanted to pursue the pursuit of honesty
0:56:01 and setting the record straight
0:56:03 and going after these bad people.
0:56:05 ‘Cause there are a lot of bad people in the world.
0:56:09 Does that 90% of the crap include your past employers?
0:56:11 Does that include New York Times?
0:56:13 Yes, 1,000% because I think,
0:56:15 because the system, it all broke.
0:56:17 Like it’s broken.
0:56:19 And I believe it’s broken beyond repair for now.
0:56:21 I might cope it so that,
0:56:23 and maybe this is me being delusional,
0:56:25 but like my hope is that AI can somehow help fix it.
0:56:29 But I believe that,
0:56:31 or AI in the hands of people can help fix it.
0:56:33 But when I first started at the times,
0:56:35 like you weren’t allowed an opinion.
0:56:37 You weren’t allowed, there was no, you know,
0:56:40 there was no social media, like there was no Twitter.
0:56:42 Like I was at the times when Twitter came out.
0:56:46 Like you, I remember being in meetings in those rooms
0:56:48 and I would ask an editor, right?
0:56:49 What do you think?
0:56:50 And they would be like, I’m not,
0:56:51 I don’t have an opinion on this.
0:56:54 My, I’m a journalist who comes at this impartially
0:56:56 and all I want to do is report the facts.
0:57:01 And so I think that what happened was you had this,
0:57:04 the problem was the internet came along, right?
0:57:06 And you had to get to the times.
0:57:07 Like I was the first one that,
0:57:09 one of the first ones that came in,
0:57:13 I remember being in a meeting once
0:57:15 with 40 or 50 people at the times, it was this big meeting.
0:57:18 And everyone kind of went around and they introduced themselves
0:57:20 and they talked about like where they’d gone to school
0:57:21 and how they’d ended up here.
0:57:23 I barely graduated high school.
0:57:27 Like I literally had a 2.1 GPA, I got kicked out of art school.
0:57:28 And like they were all like, I was at Harvard
0:57:30 and I worked at the Harvard Crimson
0:57:31 and I did this in the other.
0:57:33 And I was like, oh, I’m the odd one out here
0:57:35 that shouldn’t be here.
0:57:36 And like was only here
0:57:39 because no one wanted to write for the internet.
0:57:42 And that became, everyone became that.
0:57:46 And I think that like what ended up happening
0:57:50 was you had this generation that came in after I left
0:57:53 that was, they were the internet people,
0:57:56 they hadn’t been mentored, they hadn’t, you know
0:57:59 they hadn’t learned the ropes and they didn’t
0:58:02 and they felt like they had a right to say,
0:58:05 oh, we shouldn’t, we should not publish Tom Cotton
0:58:06 in the opinion section.
0:58:09 And we’re going to go, we’re going to be irate
0:58:11 because that is not the way the world works.
0:58:14 The world works is by listening to other people’s opinion.
0:58:16 And like, and I think the reason
0:58:18 that so many people in Silicon Valley
0:58:21 have have veered to the right, which they have
0:58:23 is because the left tells them,
0:58:25 oh, you can’t think like that.
0:58:26 And you can’t, and you’re stupid
0:58:28 if you believe this and so on and so forth.
0:58:33 And I think that, so the whole apparatus
0:58:35 is completely broken.
0:58:38 But at the same time, I am friends
0:58:41 with a lot of startup founders who tell me that like,
0:58:43 oh, we got a profile in the New York times
0:58:47 and we had the biggest influx of customers we’ve had ever.
0:58:50 Or we got mentioned, you know, a write up on here
0:58:52 or whatever it is in the same thing happened.
0:58:56 And so the eyeballs are still there.
0:58:59 People just don’t necessarily trust them
0:59:00 in the way that they did.
0:59:05 And I think that, you know, what’s interesting is that
0:59:07 you have all these new news outlets that come along
0:59:09 like Samaphore and the Free Press and things like that.
0:59:12 And they’re trying to get people,
0:59:14 they’re trying to say, we’re impartial in the middle
0:59:15 and so on and so forth.
0:59:17 But inevitably what ends up happening is
0:59:19 as soon as you put that opinion in,
0:59:23 the number of listeners or viewers or readers go up
0:59:26 and then the product ends up steering that way.
0:59:30 And so I think that there is a desperate need
0:59:33 for something that is, what I think the solution is,
0:59:37 honestly, is you don’t need a right-wing publication
0:59:39 or a left-wing publication, you need a both.
0:59:42 You need a place where there are people
0:59:43 who have right-wing point of views
0:59:44 and centrist point of views and left-wing,
0:59:46 and they’re all in there together
0:59:49 and they’re debating it and they’re respectful of each other
0:59:51 and maybe they disagree, but they are all there.
0:59:54 And the problem is the New York Times is all left
0:59:55 and the Wall Street Journal is all right
0:59:56 and so on and so forth.
1:00:00 And so you don’t necessarily trust any of it.
1:00:03 Yeah, I would love to read the debate.
1:00:06 I think that’s a lot more interesting format.
1:00:07 Two people who take the other side,
1:00:10 two people who each believe or are willing to argue
1:00:12 the best case for each side so you can read it.
1:00:13 And I think that’s both entertaining
1:00:16 ’cause it’s sort of a fight, an intellectual fight,
1:00:17 but I think it’s also more informative
1:00:20 ’cause you get both perspectives sort of steel manned.
1:00:23 Is there a story you wish you could write
1:00:25 either if you had like infinite time
1:00:27 or sometimes you get successful
1:00:29 and you’re like, oh, somebody should do that.
1:00:30 It’s probably not worth me doing it,
1:00:31 but somebody could do that.
1:00:33 Is there a great story out there
1:00:34 that you think somebody should be doing?
1:00:39 I don’t know, my dream is I love thinking about stories
1:00:42 from all different perspectives,
1:00:46 like how, when do you do, when is a story a documentary?
1:00:47 When is a story a book?
1:00:48 When is it a magazine?
1:00:48 When’s it a tweet?
1:00:53 When’s it a movie or a nine-part series on Netflix?
1:00:57 And I do, I write all forms of writing
1:01:00 and I’m fascinated by,
1:01:03 there’s these different things that are fascinating
1:01:08 is like a documentary is the people from the past
1:01:12 talking about, they’re in the present
1:01:15 talking about the past, right?
1:01:18 A TV series is the story unraveling
1:01:20 as you’re watching it unravel.
1:01:23 A book is, you get to climb inside,
1:01:25 crawl inside someone’s head for seven hours
1:01:28 and let them understand how visually things
1:01:30 smelled and looked and like,
1:01:34 and so I’ve always, I wanna write a novel at some point.
1:01:37 I think that that’s like the next thing I wanna do.
1:01:42 And so, ’cause I love, I’m a voracious novel reader
1:01:46 and I just have so much respect for the amount of research
1:01:48 that goes into them and then they become,
1:01:50 but then it’s like, it goes back to the beginning,
1:01:52 like the magic is you don’t know that the people
1:01:56 that wrote the novel spent hundreds of thousands of hours
1:01:59 researching all the history or whatever it is to do that.
1:02:02 As far as like a net non-fiction,
1:02:05 like I just love stories that are,
1:02:07 that, you know, that old cheesy saying that like,
1:02:09 you know, if it was fiction, you wouldn’t believe it.
1:02:12 You know, it’s like, I really think that those
1:02:16 are the stories that to me are the most,
1:02:19 the most fun to read and to report and research.
1:02:21 – You have all these different seasons of life.
1:02:23 You know, you said to you, in evolutions,
1:02:25 you said you wanna be a war photographer
1:02:28 and then you accidentally became a columnist
1:02:31 and then you became an author and you’ve,
1:02:34 even though you’ve disliked some of the guys you cover,
1:02:36 it sounds like there is a lot of admiration still
1:02:39 for a bunch of others as well.
1:02:40 Have you ever thought about like,
1:02:42 going into the business world
1:02:44 since you’ve been able to see it so closely?
1:02:46 – I almost did this year actually,
1:02:49 there was a project that I was gonna go do,
1:02:53 which was a startup in the storytelling space.
1:02:55 – Can you say what it is?
1:02:58 – I think that what’s happening is there’s a change coming
1:03:01 in Hollywood as far as how we consume content
1:03:04 and short form versus and the way, you know,
1:03:06 there are these structures that happen to stories
1:03:09 that we, that become norms.
1:03:11 And so for example, in a film screenplay,
1:03:14 a film screenplay is 120 pages long
1:03:16 because each page is a minute.
1:03:17 That’s why when you look at screenplays,
1:03:19 they’re courier in the certain font
1:03:22 ’cause each page shot is usually one minute long.
1:03:25 And so 120 pages is two hour movie.
1:03:28 And so there’s a whole system set up.
1:03:29 There’s a book called “Save the Cat,”
1:03:33 which essentially made this world where you,
1:03:35 on page one, the first person you meet
1:03:38 is your main protagonist.
1:03:41 By page three, you have discovered what the movie’s about.
1:03:44 By page five, there’s the introduction of the antagonist.
1:03:46 By page 30, every single movie,
1:03:48 if you go back and watch on page 30,
1:03:51 which is 30 minutes in, it’s the changing moment.
1:03:54 It’s the, you know, it is the Joseph Campbell,
1:03:56 like this is when the journey begins.
1:03:59 And then by page 90, you’ve entered this third act
1:04:02 and we’ve come back around and so on and so forth.
1:04:06 And while every movie is different,
1:04:09 we understand that that’s the same thing.
1:04:14 And I think what’s happened is that philosophy
1:04:17 has been overused.
1:04:20 And I think, do you remember the movie “Parasite”
1:04:21 that won the Academy Award?
1:04:25 “Parasite” changed it and it wasn’t, by page 60,
1:04:26 it turned into a whole different movie.
1:04:29 And you were like, “Whoa, I’ve never seen that before.”
1:04:31 And that’s why people, I think, really loved it.
1:04:36 And I think what we look for in culture
1:04:38 is things that are new and different.
1:04:40 And every once in a while, a genius comes along
1:04:44 who does it and then everyone else copies that.
1:04:45 And then you gotta wait for the next genius
1:04:47 to come along to do the thing.
1:04:52 And I think that page one, page five,
1:04:54 page 30, page 90 thing,
1:04:56 it’s completely, it doesn’t work for today’s audiences.
1:04:58 They don’t have the patience to wait till page 30
1:04:59 to find out when the turn is.
1:05:02 And so in short form, there’s like this new philosophy
1:05:05 of like one second, seven seconds, nine seconds.
1:05:07 And I think that, like,
1:05:09 but then they don’t know how to tell stories.
1:05:12 And I think that there is a world where, you know,
1:05:14 we were exploring this idea of like thinking
1:05:17 about the new approaches of how to tell long form stories
1:05:20 and short form bites and things like that.
1:05:21 And, but at the end of the day,
1:05:23 like the reason I didn’t end up doing it
1:05:25 is because I just love telling stories.
1:05:28 And I don’t necessarily wanna be like a manager
1:05:30 meeting with VCs and boards
1:05:34 and getting kicked out by Jack Dorsey.
1:05:39 How many copies of your books have you sold?
1:05:42 Hundreds of thousands of copies, yeah, over time.
1:05:44 I don’t, I haven’t checked in a long time,
1:05:46 but hundreds of thousands
1:05:47 and they’ve been printed all over.
1:05:49 Why is “American Kingpin” not a Netflix
1:05:51 like seven part series?
1:05:54 Like I can’t believe nobody’s in an amazing show.
1:05:55 It was okay.
1:05:57 That movie was okay.
1:05:58 I mean, no, it was bad.
1:05:58 It was bad.
1:05:59 It was bad, yeah.
1:06:00 It was bad.
1:06:01 I’m not gonna tell you the story,
1:06:03 but the reason it has not is
1:06:06 because I got screwed over on the film rights deal.
1:06:07 So that’s the reason why.
1:06:09 But it may end up in, it’s still today.
1:06:12 It still may end up, may end up there.
1:06:13 We’ll see.
1:06:16 – All right, if I wanted to spend six weeks
1:06:18 getting as good as I could at storytelling,
1:06:19 what would I do?
1:06:20 Is there a book or is there some process?
1:06:22 Like if I was dedicated,
1:06:23 how would I become an amazing storyteller?
1:06:24 What would you do?
1:06:25 – Well, if you’re dedicated,
1:06:26 you’d need more than six weeks.
1:06:26 So let’s pretend it’s–
1:06:28 – What would be the first, what would be the,
1:06:29 well, what could I do in six weeks?
1:06:31 (laughing)
1:06:32 I got 19 bucks.
1:06:33 – What do you got for me?
1:06:35 (laughing)
1:06:37 – If you, I have all these books on like,
1:06:40 on storytelling that I read and like,
1:06:42 and they’re interesting and like you get a little snippet.
1:06:45 I think the most interesting of all the books was,
1:06:47 I read was when I wrote Hatchin’ Twitter,
1:06:50 I really wanted it to feel like a murder mystery
1:06:52 because no one knew what really happened.
1:06:53 And I read a book on murder mysteries,
1:06:55 which was unbelievable.
1:06:56 Like you can read any of them,
1:06:58 just Google like how to write murder mysteries.
1:06:59 It’s a, it’s a blue book.
1:07:02 It’s a collaboration where a bunch of murder writers
1:07:04 and screenwriters and so on,
1:07:06 each write a few chapters each.
1:07:07 And there’s a few things I learned from that,
1:07:12 which were, which one is I,
1:07:14 when you read a lot of books,
1:07:16 people forget to describe smells
1:07:19 and murder mysteries always do.
1:07:21 And it’s like, and it brings, it really brings you in.
1:07:25 It’s, it’s wild to see how it can add like this extra layer,
1:07:28 like sounds, smells, you know, the noises,
1:07:31 you know, not just the creaking stairs,
1:07:35 but, but the, you know, the mold or whatever it is,
1:07:37 it just creates this sense of story in your brain.
1:07:39 The other thing is the Save the Cat,
1:07:40 which is a really interesting,
1:07:42 even if you don’t write screenplays,
1:07:44 it’s a really interesting way of understanding character
1:07:45 and so on.
1:07:47 And I’ve read a bunch of screenplay books
1:07:49 by like some of the old greats
1:07:50 and they talk about characters
1:07:53 and things standing in your way and so on.
1:07:56 But I will say for me,
1:08:00 the best way to become a great storyteller is to read stories.
1:08:02 And I think one of the things that frustrates me
1:08:05 about Silicon Valley and the tech bro culture
1:08:07 is everyone’s trying to optimize their life
1:08:09 for the most number of seconds of this and that
1:08:10 and the other.
1:08:12 And it’s like, what they don’t realize
1:08:17 is that some of the greatest things that they will learn
1:08:20 is from things that have nothing to do with what they do.
1:08:24 So I, and I’m 48 now.
1:08:27 When I was 45, I, I love listening to piano music.
1:08:29 I’ve never played before.
1:08:30 I was like, you know what?
1:08:33 I’m going to, I’m going to just learn the piano.
1:08:35 And, and I got obsessed with it.
1:08:36 I learned how to read music for the first time.
1:08:37 Oh, look at you.
1:08:38 What is that?
1:08:40 – I’m on a, oh wait, the cover.
1:08:41 – That says like a New Year’s resolution.
1:08:42 – This is my new year.
1:08:43 This is my new year.
1:08:44 – How are you doing?
1:08:47 – I’m on the Faber method here.
1:08:49 So I’m on book two A right now.
1:08:51 I’m playing, I’m playing.
1:08:52 – There’s a great app.
1:08:55 It’s like, it’s called that I do in my spare time.
1:08:57 It’s called notes teacher.
1:08:59 And you just do it for like five minutes a day.
1:09:00 – Site reading practice?
1:09:01 – Yeah, site reading practice.
1:09:03 But I got obsessed, obsessed.
1:09:05 Like I literally would play two hours a day.
1:09:08 And like now I can play a couple of Chopin songs
1:09:09 and things like that.
1:09:10 And I, and the thing I,
1:09:12 and to me it was just a fun hobby.
1:09:13 And it was like really like,
1:09:15 but what you learn is that like,
1:09:18 they are telling a story and they’re telling a story.
1:09:21 You know, Hans Hans Zimmer says like,
1:09:22 the notes will ask a question
1:09:24 and then the next notes will answer the question.
1:09:26 And it’s like, and the way Chopin like is,
1:09:28 you just unbelievable when you,
1:09:30 if you sit and analyze the music
1:09:32 and think about like the highs and the lows
1:09:33 and the things that are repeated.
1:09:34 And it’s amazing.
1:09:37 And it started to kind of inform some of the ways
1:09:38 I thought about screenplays.
1:09:42 And like I read as many novels as I can.
1:09:43 I hate nonfiction books.
1:09:45 I can’t read nonfiction books.
1:09:47 Which is funny ’cause I write them.
1:09:49 They’re just boring to me.
1:09:54 So I, but I read novels and I love like just studying
1:09:55 as I’m reading like,
1:09:58 oh, that was really unique of the way they did this.
1:10:00 And I read a lot of like 1950s sci-fi
1:10:02 and then I read a lot of like 1930s,
1:10:05 ’40s, ’50s, ’60s incredible,
1:10:09 you know, like the writers that we all should read.
1:10:11 And you just understand that they,
1:10:16 it’s really, these stories are about people.
1:10:18 Not the stories that we think they,
1:10:20 it’s like the guy who wrote “Game of Thrones”,
1:10:22 George R.R. Martin, I saw him speak once
1:10:24 at a conference years and years ago.
1:10:26 And he said, you know, you could take my story,
1:10:28 you could put it in a spaceship and it would still work.
1:10:30 You could put it in present day and it would still work
1:10:32 because it’s about the relationships and the characters.
1:10:35 And I think that that’s what ends up happening
1:10:38 is as you watch something,
1:10:42 the best stories are the ones where you imagine yourself
1:10:45 as the character and then you want to know
1:10:47 how you would solve the problem.
1:10:49 If I’m James Bond, how would I get out of this
1:10:53 as the drill is about to, you know, sever my heart
1:10:56 or whatever and then you can’t figure it out
1:10:57 and the storyteller does.
1:10:59 And you’re like delighted by that
1:11:01 ’cause it’s great storytelling.
1:11:02 – I think that’s your secret by the way.
1:11:05 You’re like, nonfiction is usually pretty boring,
1:11:06 but yours aren’t.
1:11:08 And I think yours aren’t because you consume so much content
1:11:10 that’s, you know, on the mystery side,
1:11:12 yours are page turners.
1:11:15 And so what, you know, that lateral thinking
1:11:17 where you take a skill from one discipline
1:11:19 and apply it to another that usually doesn’t have it.
1:11:22 That’s what some of the best business people do as well
1:11:25 is they take, you know, the best hedge fund,
1:11:28 you know, renaissance is ’cause they took the best AI,
1:11:30 machine learning, mathematical prowess
1:11:32 and applied it to finance.
1:11:34 And like we had Mike Posner on the podcast
1:11:37 and he was talking about how he started as a rapper,
1:11:40 but all his hit songs are him singing.
1:11:41 And he’s not the best singer,
1:11:43 but he’s like, I am the best writer
1:11:45 because he sang one of his lyrics
1:11:48 and he’s like, the rhyme scheme I’m using here,
1:11:50 the reason people like that hook and it’s catchy
1:11:52 is ’cause I’m using a rap rhyme scheme
1:11:55 which no singer-songwriters would typically do,
1:11:57 but that’s why my song sounds different
1:11:59 because I’m using a rapper’s lyrics,
1:12:01 but I’m singing them in the way that, you know,
1:12:03 is rarely done.
1:12:05 But it sounds like you’ve kind of done that same thing.
1:12:07 – No, I think it’s totally true.
1:12:09 And look, I think Jobs did this thing
1:12:11 where he, you know, computers back then
1:12:14 were these nerdy like circuit boards.
1:12:17 And he was like, oh, I’m gonna marry graph design
1:12:19 with technology.
1:12:23 And so for me, like I wanna marry the style of a novel
1:12:25 with a narrative nonfiction story.
1:12:28 And, you know, this great writers who’ve done that
1:12:31 in the past that I such, such admiration for.
1:12:32 – Whenever I get done reading your books,
1:12:33 like when I get done,
1:12:35 each time after I’ve read “American Kingpin,”
1:12:36 I’m like pretty bummed.
1:12:39 I’m like, oh, I was so like in love with like reading this
1:12:41 and I was looking forward to,
1:12:42 or I was looking forward to like,
1:12:44 I would sneak off to like find the page
1:12:47 and see if I can just like read a few chapters.
1:12:51 And I felt bummed that like I was like in this relationship
1:12:53 with this book and it’s over now.
1:12:56 And I would, I’ve like searched so long and hard
1:12:58 to find something that could fill that need.
1:13:01 And like only one out of like 20 or 30 books
1:13:01 like fills that need.
1:13:03 I think “Mastermind” was another great book
1:13:05 that was a very similar topic.
1:13:07 And the author did a great job
1:13:09 of a very similar style of storytelling.
1:13:12 But in general, it’s been really hard for me to find things.
1:13:13 I read a lot of novels, but I like reading,
1:13:15 I like sometimes when I read a novel,
1:13:17 I’m like, I fall in love with this character.
1:13:19 And then I find out that I have to remind myself
1:13:20 the character is not real.
1:13:22 And I get kind of like bummed about it, you know?
1:13:25 And so what, who do you view as a peer
1:13:27 or someone you look up to
1:13:32 or they do your style of non-fiction storytelling?
1:13:34 – Oh, well, just to real quick on the novel,
1:13:36 like yes, they’re not real,
1:13:38 but they are based on reality.
1:13:42 Like every novelist pulls from the people around them
1:13:45 to create the characters that you’re reading.
1:13:48 So, you know, it’s like, you know,
1:13:52 if you go do research into like whatever your favorite book is,
1:13:53 your favorite novel, like,
1:13:54 and you look at how they did it, if they talk about it,
1:13:57 they’re like, oh, this is me, you know, when I was a kid,
1:13:59 my grandfather used to tell me the stories about Da-da-da-la,
1:14:01 or like there was a neighbor across the street.
1:14:04 So I think they are, it is real and it’s still people.
1:14:09 As far as people I admire and I look up to,
1:14:11 I, like I said before,
1:14:13 I don’t really read a lot of narrative non-fiction,
1:14:15 I’m sorry, a lot of non-fiction.
1:14:18 I don’t think there’s that, like,
1:14:22 and I love, I have such admiration for people’s reporting
1:14:25 and even the writing, but this isn’t, I need a story,
1:14:27 I can’t have a, so I,
1:14:28 – That’s what I’m describing.
1:14:30 I want more like story-driven non-fiction.
1:14:31 – Yeah, I need a story.
1:14:32 – This is the shit, man.
1:14:35 I’ve just, like, I just love learning about this stuff.
1:14:37 – Well, you had one last question, Sam,
1:14:39 and I interrupted you, or did you answer it?
1:14:42 – Well, it was about, Sean,
1:14:45 did you see the documentary on Netflix about,
1:14:47 was it, what was it called with Ilya?
1:14:48 Was it Bitfinex?
1:14:49 What was that called?
1:14:52 – It was the couple, a Bitcoin Bonnie and Clyde,
1:14:54 I did a documentary on them for Netflix
1:14:57 with Chris Smith, who did Tiger King.
1:15:01 That was about this couple that had stolen 5.4,
1:15:04 well, they stole $72 million in crypto
1:15:06 and then we’re trying to launder it and ever,
1:15:09 they were the only two people on the entire internet
1:15:11 who wanted the price of Bitcoin to go down.
1:15:14 And they had, every time they were trying to launder it,
1:15:16 it would double and double and double and double and double
1:15:17 and to the point that it was,
1:15:21 at one point at its peak was worth $8.4 billion.
1:15:24 And she was this like wacky cringe rapper
1:15:26 and he was like a part-time magician investor
1:15:28 and like, it’s one of those stories.
1:15:30 If it were fiction, you’d be like,
1:15:32 “Yeah, this is stupid, this had never happened.”
1:15:35 – She shot, or the guy, Ilya,
1:15:38 spoke at the very first Hustle Con, which is kind of funny.
1:15:39 And then the woman had–
1:15:41 – The new Forbes 30 to 30, did you smile?
1:15:43 – Well, listen, the woman had there,
1:15:45 she was like a copywriter or something,
1:15:46 but she wasn’t any good.
1:15:50 And she like DMed me asking to talk at one of our things
1:15:53 or to like do freelance work or something like that.
1:15:55 And then she was kind of a sex freak.
1:15:58 I had a bunch of friends that like fooled around with her
1:16:00 and they were like, “This woman’s wild, man.
1:16:03 “You should stay away,” like those type of stories.
1:16:05 And I was like joking with Nick.
1:16:08 I was like, whoever I guess we interact with,
1:16:09 just like maybe 10% of them
1:16:12 are gonna end up becoming like amazing criminals.
1:16:13 Because for some reason, we’ve been around
1:16:16 a bunch of these people, like right as or right before
1:16:17 they were committing some huge crime.
1:16:21 But that was also a good story.
1:16:21 – Yeah, that was a great story.
1:16:25 That was just a wild story that they went on,
1:16:30 they went to Ukraine and like had like fake passports.
1:16:33 And I mean, it was just, yeah, it’s nuts.
1:16:35 – Is making a Netflix documentary,
1:16:36 is there good money in that?
1:16:37 Or you do it just ’cause it’s sick?
1:16:40 And it’s like, as art and I’m doing this for art,
1:16:41 how does that work?
1:16:43 – There’s not, look, being a writer, I think,
1:16:46 it’s good money, like if you can pull it off.
1:16:49 There’s somebody sent me an article a while ago
1:16:51 that you’re more likely to become a billionaire
1:16:54 than to become a successful writer.
1:17:00 And yeah, it’s like, I think the way in the olden days,
1:17:04 Vanity Fair, for example, or the New Yorker,
1:17:05 they had these contracts for these writers.
1:17:08 They would get paid hundreds of thousands of dollars a year
1:17:10 and they would write four stories a year.
1:17:12 And like, and then they had the house upstate
1:17:13 and the place, the Brownstone in Brooklyn.
1:17:15 And like, it was a different time.
1:17:18 And now, you know, everything’s been diluted,
1:17:22 media has been completely diluted where we have podcasts
1:17:25 and blogs and newsletters and mainstream media
1:17:26 and all the stuff.
1:17:30 And so the advertising dollars and the revenue dollars,
1:17:32 it’s not like they’ve gone up.
1:17:34 It’s just they’ve evenly been more evenly distributed.
1:17:38 And so for me, I just want to tell stories
1:17:42 and I just don’t give a shit in what format it is.
1:17:47 And so it’s really fun to be able to write screenplays,
1:17:48 to write books, to write magazine features,
1:17:50 to make documentaries and like,
1:17:53 and then, you know, it all just kind of adds up from there.
1:17:55 – I could talk to you with you for hours, man.
1:17:56 Thank you for doing this.
1:17:57 – Thank you so much for having me.
1:17:58 This has been really fun.
1:17:59 – We appreciate you.
1:17:59 All right, that’s it.
1:18:00 That’s the pod.
1:18:01 – That’s the pod.
1:18:03 ♪ I feel like I can rule the world ♪
1:18:06 ♪ I know I could be what I want to ♪
1:18:09 ♪ I put my all in it like no days off ♪
1:18:12 ♪ On the road, let’s travel, never looking back ♪
1:18:22 – Hey, Sean here.
1:18:23 A quick break to tell you an Ev Williams story.
1:18:25 So he started Twitter and before that,
1:18:27 he sold a company to Google for $100 million.
1:18:28 And somebody asked him, they said,
1:18:29 “Ev, what’s the secret, man?
1:18:31 “How do you create these huge businesses,
1:18:32 “billion-dollar businesses?”
1:18:34 And he says, “Well, I think the answer is
1:18:36 “that you take a human desire,
1:18:39 “preferably one that’s been around for thousands of years,
1:18:42 “and then you just use modern technology to take out steps.
1:18:44 “Just remove the friction that exists
1:18:46 “between people getting what they want.
1:18:47 “And that is what my partner Mercury does.
1:18:49 “They took one of the most basic needs
1:18:51 “any entrepreneur has, managing your money
1:18:53 “and being able to do your financial operations.
1:18:54 “And they’ve removed all the friction
1:18:55 “that has existed for decades.
1:18:57 “No more clunky interfaces,
1:18:59 “no more 10 tabs to get something done,
1:19:01 “no more having to drive to a bank,
1:19:03 “get out of your car just to send a wire transfer.
1:19:05 “They made it fast, they made it easy.
1:19:06 “You can actually just get back to running your business.
1:19:08 “You don’t have to worry about the rest of it.
1:19:09 “I use it for not one, not two,
1:19:11 “but six of my companies right now.
1:19:14 “And it’s used by also 200,000 other ambitious founders.
1:19:17 “So, if you want to be like me, head to mercury.com,
1:19:18 “open them to account in minutes.
1:19:21 “And remember, Mercury is a financial technology company,
1:19:22 “not a bank.
1:19:24 “Banking service is provided by Choice Financial Group
1:19:26 “and Evolve Bank and Trust members, FDIC.”
1:19:28 All right, back to the episode.