We talk to the guy who knows Silicon Valley’s darkest secrets | My First Million

I've got Steve Jobs stories.

I've got Jack Dorsey stories.

I've got Ross Ulbricht stories.

You name it. I got them.

I feel like I can rule the world.

I know I could be what I want to.

I put my all in it like no day's off.

On the road, let's travel, never looking back.

All right. Sam has been telling me about a book for probably 10 years in a row.

And I finally got around to reading it this year.

And the book is American Kingpin.

It's a story of the Silk Road, of Ross Ulbricht, who created it, grew it to great prominence, ended up going to jail, what we thought was for life, and then he just got pardoned by Trump.

And so Sam just re -read the book.

I read it this year.

We both love this thing.

It's a page turner.

And the author, Nick Bilton, not only wrote that, but he wrote Hatching Twitter and a bunch of other stuff.

Fascinating guy. And he's here with us today on MFM.

So let's do it. Nick, what's going on?

We wanted to talk about all types of stuff.

We want to talk about storytelling.

We want to talk about things that you researched that didn't make the book we want to talk about like the og stories of silicon valley because you've been covering this stuff forever but you're like one of the three people who we've had on the pod that i'm like nervous to talk to and i stayed up all

night like reading everything about you don't be nervous this is exciting this is fun it's gonna be great we're gonna tell some some crazy stories i've got steve job stories i've got jack dorsey stories i've got ross albrecht stories you name it i got them who of all those people did you have you become

friends or uh admire any of them or do you are you like a strictly like a journalist who doesn't cross the the barrier well that's a great question um i feel like we should save i should save that answer because i've got such great stories about all these people about bezos everyone where you know there are some

that i have become friends with and then unfriends with and some i'm still kind of friends with, but let's save that for when we get into the hatching Twitter, Elon Musk, Jack Dorsey territory of this pod.

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I was listening to an episode with David Perel.

It was all on writing.

And you talk about like what makes a great story.

And this sounds like a backhanded compliment.

I think that your writing is amazing.

Your storytelling is amazing.

I think you just happened to pick the best story of all time with the Silk Road.

Like it was like set up to win.

Well, I think, I mean, let me just tell you how I came to the story.

So I was a reporter at the New York Times and in Silicon Valley covering tech, I was writing about Apple and Facebook and Twitter.

And I don't even know how to describe this moment in time.

You know, it was like 2008, 2009.

It was, you know, right after the bubble had popped, the second bubble.

And it was, again, once again, this no -fly zone, you know, to be in Silicon Valley to do startups and whatnot.

And I started covering these companies that were not – the idea of one of them being a trillion -dollar company was just – it was ridiculous.

That would never happen.

And I would spend time with Steve Jobs and Bezos and Zuck and Dorsey and all these guys.

And I wrote the Twitter book, which we can talk about, and there's incredible backstories to that, and of people trying to kill the project and so on and so forth.

But I'd finished the Twitter book, and the Twitter book had done really, really well, and I was looking for a new book.

And I couldn't – you know, I really – I love writing books.

It's one of my favorite forms of writing to do.

And I heard about this guy who had started the Silk Road who had been arrested at this little public library that was like four blocks from my house.

And I knew the library.

And I knew the area.

And I also knew the Silk Road.

And so I wrote a piece for the New York Times about it.

It's like a short piece.

And then I was like, maybe there's a book in this.

And as I started to dig further and further, it just felt undeniable.

It was just an unbelievable story of this kid who—I say kid because he was very young at the time.

But he grew up in Austin.

He was incredibly smart, 1600s on his SATs, studied astrophysics.

Went off to one of the best schools and and then had this like libertarian idealism to him that is no different to like Travis Kalanick when he's building Uber and, you know, all these other people in Silicon Valley.

And he decides that drugs should be legal and the government should not be able to tell you what you can and cannot put in your body.

And the only reason that the drugs lead to these, you know, to deaths and murder and so on and so forth is because the government has so much control over it.

And so he takes the Onion browser, which is the secret browser that you can – where the dark web exists.

And then he takes Bitcoin, which both kind of come along around the same time.

And he creates this proof of concept, which is this website called the Silk Road.

And then next thing you know, he's making millions and millions and millions of dollars a day as the biggest drug dealer on the internet.

By the way, how good was the branding for that?

The fact that he called himself the Dread Pirate Roberts, the Silk Road, the logo behind it?

The branding was actually pretty brilliant.

No, the branding was great.

I forget the name. There was a name that he had originally wanted to call.

It was like some terrible name.

It was called Hardcore Underground or something where it was like, I'm interested in that.

But what's fascinating is, you know, at the time he's living in Austin, he's got this girlfriend, Julia, and they're kind of in this like toxic relationship.

And he has this business, and it's a pretty like nice business where he goes around and he collects books that people want to get rid of and then sells them and mails them out.

So when he moves into the drug trade and he goes to Bastrop State Park and he rents a cabin and he grows mushrooms so that he could sell drugs on there to show that you can sell drugs on there.

And then he starts mailing them out.

Like he's mailing the books out and then the drugs out.

And like – and it all kind of – it all comes together in this very, very unique way.

What ends up happening is Gawker, the website that is obviously now defunct, they write about it and then that's it.

It's like game over.

Like everyone on the planet knows about it and senators are coming after him and every government official from the IRS to the FBI to the Secret Service to the DEA, they're all trying to hunt down the Dread Pirate Roberts.

And Ross essentially goes on the run around the world as they're trying to catch him.

Yeah, it's one of the best things about the book is that it starts with, like, I don't know how much of this is your conjecture versus you had his diary, I guess, and you knew some of his thoughts.

But it's like, he knows he's smart.

He wants to do something special.

He's sort of bummed out that he hasn't done anything interesting or special with his life.

And, you know, has sort of tried but hasn't really made it yet doing anything.

And then you've got his girlfriend, and there's that part of it.

They've got the libertarian ideals.

And then it leads to, you know, the thing escalates like crazy where I think, I don't know if it's peak, but I think Silk Road was doing like, you know, over a billion dollars, like GMV through the marketplace.

Yeah. And there's like, you know, murder for hire plots going on.

Like, it escalates like the craziest crime movie would escalate.

But I like that you had that beginning part where it wasn't just this criminal mastermind.

It was like this smart kid, you know, just trying to do something and had a certain set of ideals.

How did you know what he was thinking?

How did you get access to his diary?

Why does a writer—how does a writer like you get that?

And you got a lot of stuff.

You got, like, the footage of the library where he got arrested.

You got, like, the chat logs from, you know, with the government.

How did you get access to all this information?

Well, I can't tell you exactly how I got a lot of it, because that's investigative reporting.

And I, you know, obviously can't divulge where it came from.

But the way I approach these stories is I want to know everything, literally everything.

And so I have these researchers who work for me, and one of them actually used to do OPPO research for the Democratic Party trying to find bad stuff on Republicans.

And we literally just blanket approach it.

And what's been really interesting, I have a new project, which I can't talk about, but I can tell you a little bit about how I've been reporting it.

What's been interesting is I have a new project that we're doing, and we've been using Google LLM's notebook.

And so now we stuff millions of words into these things, and I can just query it.

Whereas before we had to build like Excel spreadsheets and databases and like, it was very, very complicated the way we did it.

But we kind of put into three tranches.

So we have the DreadPire Roberts and we get access to the chat logs that were on his laptop, which I don't actually know if he knew were there because they were in a hidden folder.

And I don't think he actually knew he'd been saving them or maybe he was, I don't know.

And then there's some diary entries.

he'd literally been making a diary about about the thing because he would he the best line ever is he thought there'd be a book written about his life one day um and then we and then we go through social media and we and we get all the photos and all the posts and all that and we everything's on a timeline

it's all got time stamps and then and then lastly it's the interviews with everyone and with as far as like you know i we reach out we get yearbooks and you go and you find out everyone he went to elementary school with the middle school and high school and you interview everyone.

You find the neighbors, the kid that lived across the street, you know, which coffee shop you went to, you go to the coffee.

And then the thing I do, which is a little psychotic, but I do it anyway, is I want to be able to describe what the, I want you to feel like it's a novel in some respects, but it's all real, like nothing's made up.

And so like, if I know he, let's say he took a picture, there was one instance where he went camping And so I didn't know where the campground was.

It was near San Francisco.

But he had taken two pictures, three pictures, sorry.

One was when he left, and we could figure out the street because we could, you know, see the angles and the street signs.

The next was when he was driving over the Golden Gate Bridge, and then the third was when he got to the campground.

And we could tell the timestamps, so we just did the math.

And we're like, OK, it's probably 45 to 50 miles away.

And then we looked in the circle around San Francisco, and then we found these different campgrounds.

And I went to one, and there we are at the campground.

So I go there, and I find the place that he took the picture from, where he's sitting.

I sit in that spot, and I can smell the everything.

And so I can describe that because it hasn't changed in six months or a year.

It still looks the same.

And so I do that with, like, everything.

I go to the coffee shops he goes to.

I walk the same street.

And so you get to describe this and then you also can look with different apps where you can see the way the sun comes on certain days and you can describe what the shadows look.

And you just can describe everything.

Sam, isn't this wild?

It's wild in two ways.

One, it's the same sort of obsession of why Jobs is like, I'm going to design.

We need to finish the inside of the casing of the computer.

And they're like, Steve, nobody's going to see this.

And he's like, I've seen it.

I know it's there. that's why we have to finish this the inside case so this is a weird kind of product obsession which I respect but then there's also like dude nobody would know nobody would ever know and it might not ever matter why does it matter to you to do that well and it's also weird that Nick

you've written like hatching Twitter wasn't the most favorable towards like Jack Dorsey and some of these guys you guys all have the same flavor of crazy though you know what I mean like that that's what Sean's describing is like what the greats have look I totally agree look I mean it's fun for me

I think it's like, I, I love the challenge, but I, it's, what's interesting, you bring up jobs.

Like I spent, I spent quite a lot of time talking to him when he was alive.

And he was incredibly obsessive.

And of course, and like, and you know, one of the things that he always said that, that he may set it publicly too, but like, you should never know that the technology exists and how it happens and so on and so forth.

And, and it's, I'm fine coming on a podcast and talking about how I did it, but when you're reading, I'm not going to tell you, like there's nothing that drives you more insane where it's like according to a transcript that I found, it's like who gives a shit?

Like just tell me the story.

And I think that one of the beauties of great products is when you don't know how it works.

And I think one of the – it just works and it's magical and it's all those words that they use in the ads and everything.

And I think the same is true for storytelling.

You know, like, a lot of the greatest novels, I'm a voracious reader, I read a ton of novels.

And a lot of the greatest novels, the amount of research that people like Gabrielle Garcia -Mercedes put into 100 Years of Solitude and, like, into chess, it's like when you read these, they're not telling you all this, they're just telling you a story.

Why would – I saw that you – I think you said in another podcast you spent, like, three or four weeks with Julia, Ross's ex -girlfriend, when he was starting it.

and there are and and and i didn't know that you had spent time with them when i was spent time with her because i was like why why on earth would she ever talk to nick like you know if i'm her i'd probably just kind of shut up but you knew stories like you knew like when they had sex or like like the comments

that they made to each other i'm like how on earth does he know this and then i find out that you i heard you spent time with her like getting info why on earth would some of these sources talk to you why not why wouldn't they just say i don't need that in my life get out of here I think one of the things

I've learned as a reporter for two decades is that people want to talk for different reasons.

So you get – there's endless numbers of them.

And one of – I think – people think being a reporter is like you got to break the news and you got to write the story.

It's like no, it's relationships.

It's like it is literally just relationships.

And what you have to do is you have to figure out, you need these people to talk to you and you have to figure out how to make them want to talk to you.

And so, for example, everyone has a reason.

So people that would leak stuff to me that worked at Apple or Facebook, some of them were just so excited to say, oh, my God, I worked on this thing.

And it was like, and they just want it out there and they don't have the patience.

And, you know, and others of them worked on something that never got made or they got fucked over by their boss.

So they didn't get the credit and like, or like they have other egotistical reasons, whatever it is.

And so your job as a, as a reporter is to try to get them to talk to you and to try to figure out.

And my job is to be like, why, what can I say to you?

What is it that you want?

I know you want some, we all want something.

And so with Julia, you know, I think, I think she wanted, she wanted to be part of the story.

And I think she wanted to be famous a little bit.

And I also think that she, for her, there were some things that hadn't been said and hadn't been finished and that she hadn't, it was like a little bit cathartic, I think, in some respects.

And so that's the reason she talked.

When it came to the agents, you know, I spent time with all of the agents involved in the case, almost all of the agents.

And, you know, with Jared T.

Egan and I probably spent 400 hours, 500 hours together.

You know, we, I went to his office, I went to his house, I went to his.

we we met in all different places i saw the postal service where he worked and that we went inside the chicago airport and underneath the bowels of it i mean it was amazing to see all this stuff sean do you remember that where so jared was the guy who like he wanted to be an fbi agent or something like

that but he ended up being a homeland security agent which is like like i think the book starts with him it's like he's discovered a pill yeah a single pill one pill and what shocked me about homeland security and mail is that they would just sit there and watch packages come in and they would just

be like that that envelope looks weird because uh like it's handwritten in a certain way uh and it's just similar like it's just so crazy that one of the one of a few different ways that he was caught was just like traditional uh police work as opposed to like something more complex it was shocking

that it was just like eyeballing things well it's what's what's what i why i started with the pink pill the single solitary pink pill is because And then there's a paragraph in the book about how the website started with a single line of code, and all of a sudden he creates this world and so on.

I think what's interesting about technology, and this was just me, the way I wanted to tell the story, but what's interesting about technology is also the scene where, and I say scenes because I think of them in my head as scenes.

They're not chapters.

Everything's visual in my head.

And there's this scene where we see a computer being built.

And it starts with like a single diode.

And what I find so fascinating about technology is all these websites and all these products and all these companies, they start with this little – this one thing.

And the same with the books and everything.

And they grow into these – they take over the world.

And so for me, the pink pill, the single solitary pill of ecstasy was the beginning of the story, which was just going to become a fucking tidal wave that took over everything.

Did you ever feel in danger during your research?

I felt more in danger doing the Twitter book, quite honestly.

What was the danger there?

The powers that be didn't want?

Jack Dorsey did not want that book out.

And he was trying to do everything he could.

Dude, he's a peace -loving hippie.

As far as I could tell, he sits with a beard and a tie -dye shirt.

He just wants peace and love for all, I thought.

No, it's all a story that he tells.

Look, there are definitely stories I've worked on.

I wrote a book that I chose not to publish.

It was just about the NRA.

This was after Marjory Stoneman Douglas had happened because I went to school there.

And I spent a couple of years on the book and then decided to not do it for a few reasons.

But that one, I wouldn't even say that was – I wasn't, like, afraid someone would come after me except maybe, like, some gun nuts later.

um you know i've done some stories mafia stuff like russian hackers things like that um and i've never you know i think a lot of the times people respect the process and they don't they they don't want to start a war with the new york times or vanity fair or you know right i think it's different if you're

like covering mexican cartels in you know in mexico that what that's that's a whole different thing or if you're trying to be a reporter in russia or something like that, that's where you really do have to start to worry.

But in Silicon Valley, it's a bunch of nerds that talk a big game, and that's it.

I do have one story, but it's from the Twitter book.

So when I, I won't mention names here, but when I wrote the Twitter book, and there's a moment in the book where someone gets fired, and I got a call from a friend who's a journalist at bloomberg and they said hey someone there's a there's a bunch of people these like crisis pr people that are trying

to they're calling all the journalists they just called me and they're trying to say that your book is all fabricated and it's not true and this especially this moment it's all made up and um and i just wanted to let you know and i was so i just called this woman directly and i was like hey uh heard

you're calling everyone and saying she's and she's like i didn't say that.

And I was like, I said, look, I have the tapes of the interviews of that moment.

And I was like, I will happily post it on Twitter.

I said, you just keep calling people and I'll put it on Twitter.

And that was the end of it.

So there are these moments where you get these crisis comms people that come after you, but.

Well, when you do as much research as you do, you end up getting to know the subject in some ways better than themselves.

It's like in business, these CEOs will pay for these expensive 360 reviews where somebody goes and talks to their wife and their co -workers and their interns and they come back with this feedback and it's supposed to be this eye -opening thing about them.

This person can find out more about them and show them a mirror that they haven't really seen before.

In that case, they want it.

But, you know, when you're researching Jack Dorsey and you say something like, you know, that's all the story, who's the real Jack Dorsey?

Well, I think just one thing about what you just said is I know somebody asked me once how do you know when your book is done when you're like when you're ready to to because what happens is you research for for a long time you don't write a word until you're ready until you've done all the research

and you have everything and I have in my office I have these boards and I'd like create these cards like that that you can you know where they're just all the scenes of different colors and everything and put them up on a wall and And I know when I'm ready to write, when I start telling the people I'm

writing about things they don't know about themselves.

And that's the moment I'm like, okay, I got it.

And so that happened with the Twitter book.

I remember sitting with all the founders.

And there was a moment where I told Evan Williams something that had happened behind his back that I thought he knew about.

And he had no idea.

And I was like, oh, okay, well, there you go.

I'm ready. And, you know, as far as Jack specifically goes, the best quote I ever got about Jack Dorsey and I've written a lot about him was from one of the board members years ago who said the best product Jack Dorsey ever made was Jack Dorsey.

Because it's because that's what it is.

It's everything is everything is a story, right?

Every single solitary thing we do every single day is us telling a story.

The outfit you chose to wear today is a story about yourself.

Me telling a story about the book is me.

It's all we're doing all day long.

And we're telling these stories, and we choose which story we want to tell certain people based on how they want us to perceive us.

And I think that people like Jack and Jobs and Bezos, all of these guys and Zuck, that's one of the things they're great at is telling a good story.

And I think – like I personally believe that your story for a company is more important than anything.

I don't care if you have the greatest product in the world.

If you can't tell a story about it, well, what's the point?

What's the example that drives that home?

YouTube is a perfect example.

YouTube was not the first video platform.

There were dozens. And I remember seeing this.

Like when I was just a beat reporter covering Silicon Valley, and my days were like, it was like office hours.

And you'd have like startup after startup in like 2009, 11, 12, come in and meet with you.

And they would have, you know, some of them would have great ideas.

But they couldn't walk you through it.

And they didn't hire a PR person.

And they didn't like – and so, you know, and YouTube – YouTube had a great story and that they were able to tell.

And that became – and it became the video platform.

There were other video platforms that were, I would argue, way better than YouTube.

And I mean, Vimeo is a perfect example.

Vimeo was a thousand times of a better product and prettier, easier to – all these things.

And YouTube just told a great story, and Google helped them do that.

And it becomes – that's what it becomes.

And if you – if Jack Dorsey had told the real story about Twitter that his best friend Noah Glass really was the one that came up with most of it and he stole it, you know, from him and, like – and the place was a shit show and no one knew what was going on.

and it was all an accident.

You'd be like, oh, okay.

But to tell the story that I am the next Steve Jobs and I conceived of this idea of Twitter while I was in my mother's womb and like, holy shit, I got to check this thing out.

What is this? And it's like - Yeah, like the Jack Dorsey Twitter story I know is he grew up and he was just fascinated with dispatch or something like that.

He talks about like, I loved either taxi dispatch or some transportation dispatch service he used to listen to in that short form.

dispatch communication was always something he was into.

And then when he had the idea for Twitter and he has the sketch of the original Twitter thing that he's posted before.

That's the story that I know, right?

Because I'm just the receiving end of that product he's created.

Yeah, so it worked, right?

The story worked. Is it true?

No, it's not true. Yes, he was interested in dispatch in the same way he was interested in writing poetry and painting his nails black and dyeing his hair blue.

But that's not part of the story because what really happens is, and as I say in Hatch in Twitter, and no one knew this.

I was like, I had to talk to all these different people to kind of pin it together, except Noah Glass knew it, was Jack was living in San Francisco.

He was in his early thirties.

He was like a part -time manny in Oakland.

Like his life had not turned out in any way like the predestined version of Jack Dorsey we think of today.

he got a job working at a um you know the ticketing booths at alcatraz um the so there are these booths that are pretty small and he was the c programmer who would go and fix the ticketing booth and the reason he got the job was because he was small enough to fit inside the booth and programmed um so this was the life

he was living and he he had went he applied for a job at camper shoes to sell shoes, not, not like to build the website or be the CEO like, and he couldn't get the job and he was at a coffee shop and Evan Williams walks in and he'd read an article about Evan and he just felt like it was a sign, which it

probably was the universe was putting them together.

So you sent him a note and he said, I'm a programmer, you know, and they had Odeo at the time, which was the podcasting company, which was a decade ahead of its time, which was a brilliant idea that that noah glass had come up with and so noah and and evan williams had created this thing called blogger

um uh and blogger was again ahead of its time you know and google purchases it and one day this guy biz stone reaches out and he says i love blogger i'd love to come work for you and uh so evan williams and biz become friends at jason goldman who's also another part of this he's working at google they

all kind of become buddies they end up leaving and we'll get Goldman stays, but Evan Bizz end up leaving.

And the reason that they leave is because Evan lives on, I think it was like 18th and market or whatever the streets were.

And he, one day he was on his balcony and another guy, Noah glass was on his balcony and Noah had been reading that same article that Jack Dorsey had read.

And he recognized in the article that the photo of evan was of ev williams was taken on the balcony and in the background there's a little noah glass because they were neighbors and so he goes out he goes hey blogger and they become friends and then he pitches and noah pitches in this idea for this podcast

company he's like this is the vision this is the future it's going to take over radio and so on and so ev is like looking for a project and so he agrees to do it it's all discombobulated no one knows what's going on like They can't run the startup.

Apple comes along with podcasts.

They're screwed. Jack Dorsey comes along and they do a hack day and to try to like last hurrah to save the company.

And they, during the hack day, Jack presents this idea for status, okay?

And everyone's kind of doing the same thing.

The ideas are very, very similar and I'll tell you a couple of them.

But Jack presents this idea for status.

And what status is, is stat .us slash Nick Bilton, right?

And you go there and you see my status.

It's one status. If I say, and it's three, four words.

You're not really supposed to do anything more than that.

On a podcast. Now, if you go an hour from now, if I post a new status and I'm like taking a walk, on a podcast is gone.

And it now just says taking a walk.

It's like an AMAway message.

It's literally an AMAway message that they were doing.

And so Noah has a very similar idea, but Noah's like no one is going to go stat .us slash Nick Bilton five times.

Your mom will do it because she wants to know what you're up to but no one else is doing that and so they all start bringing these ideas together and it's truly it's like 11 people in the room it it is a collaboration between all of them and what Noah has this realization is he's a very emotional guy

very smart and he's like it needs to be about friendship.

It needs to be about connecting with your friends and that is what it's about and so he brought this humanity to it and so he came up with the stream and the ad it's like all not the at replies but the friends like that you had friends and you and that was what that was twitter it wasn't status you

know it there were a million other statuses back then I mean um and so when it ends up becoming what it became Noah was a mess he was getting divorced, he was like he just his life just wasn't working, and he gets pushed out by Jack and Ev and those, and Jack, who is best friends with Noah, goes into

Ev's office one day and he says, either you get rid of Noah or I quit and as far as Ev knew, Jack could come up with the idea himself, you know, when he was a little kid listening to fire trucks, that was a story that was added later and so, you know, so, but that's, but the better story is not, oh,

I screwed over my best friend for power and control of this thing it's when i was a kid i used to sit in my room at 12 years old and i had the vision for twitter by listening to firetrucks okay that's a great story and so i you know you seem like you don't like jack dorsey is it uh you don't like him

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Again, billion dollar moves.

All right, back to the episode.

Did you find yourself like you had this great podcast with our friend David Perrell, and you said a line that hitchcock someone came up with where it was um every villain has a mother uh and it was like uh i guess like you you see yourselves in the villain at times that's what good stories do you kind

of like uh like a villain a little bit or they're a little uh you know you're you're you're you're interested in them did you find yourself liking ross did you find yourself liking jack at times like because you get so into their minds and you also see that like even though they do a lot of bad things

they do a lot of epic things a lot of big things, do you find yourself admiring and liking them?

Well, they all have a charisma to them, that you can't pull this off without the charisma.

I met Trump. He's very charismatic, very, very charismatic.

You want to be around him, even if you don't agree with him.

What was the context?

How'd you meet him?

Oh, just at a rally once, years and years and years ago, I think 2015 or something like that.

Spent time with Elon.

He's kind of funny.

He's funny. He's like a weird dude, but he's funny.

You know, Jobs had this like aura to him, you know, Bezos too.

Like they, funnily enough, Zuck doesn't necessarily have the charisma, but it's almost like he's a robot.

And you're like, oh, how does this thing work?

But they all have this, there's something to them that is enticing.

And Jack's funny. He's a funny, nice guy.

Like when you're hanging out with him, it's like, you're like, oh, he's fun.

I like hanging out with this guy.

And I never met Ross.

I covered him in the court in the trial, so I saw him many, many times but never spoke to him.

But they have this charisma to them that I think makes them great in some respect, and it's not something that you can learn.

It's just something that you either have or you don't have, and so you cannot help but like them for that.

But I think for me, I just – I don't understand – here's the part with Jack and then we should move on from it because I could talk all day about this.

But Jack is worth $12 billion, give or take.

Noah Glass is worth about a zero dollars, okay?

He never got anything.

Ev gave him something and he had to live off that and whatnot.

not if you're worth 12 billion dollars give the guy 10 million you wouldn't even notice you it would literally be like losing a penny between your couch cushions and like that to me even if you believe that you are the creator even if you believe that that you that you really came up with this on your

own because he may believe that today i just don't understand like why the kid that you were best friend the guy you were best friends with who who without question helped you with this product, like go take care of them.

And it never happened.

Well, No Glass, I agree with you.

But also No Glass now has a thing too, right?

Doesn't he have Olo or...?

No, that's a different No Glass.

No shit. They're not the same guy?

Not the same guy. Everyone thinks that.

I thought it was like his second coming.

No, he has a family and he married this French woman and they have two kids.

Dude, not only Twitter got stolen from him, His own name got stolen.

His name is based on Google got stolen from him, too.

Let's go by the other guy.

This guy gets no credit.

Mess him up. I did not know that.

I thought it was like, oh, he's getting it back.

Oh, man, that ruined this story for me.

Can you tell us some other stories that have stood out to you, things you still remember, either experiences or whatever?

You said, like, I got job stories.

I have Zuck stories.

I have Elon stories.

Let's see. Jobs is the best one, I think.

I'll do the job story.

So when I was a reporter at the Times, I didn't really know what I was doing.

Like, no one knows what you're doing when you start out in these jobs.

You pretend you do, but you don't.

And I think the 10 ,000 hours is nonsense.

I think it's about 30 ,000, right, to really understand what you're doing properly.

But I was at the Times and I was, what had happened was I'd come into the Times by complete accident.

Let me just start with that story because it's actually a very funny story.

So my dream job was I wanted to be a war photographer and I'd read all these war photography books and I bought like, saved up and bought like a fancy camera and I would like do practice war photography with my friends where they would like run through the streets, you know, and I would take pictures

and, and so I put together this portfolio and I was a graphic designer and I'd done toy package design for a while.

And they'd like designed diverse Britney Spears doll and stuff like that.

And so I was like, oh, I can use the designer job to get to the times as a designer, and then I can become a war photographer.

And so I end up doing that.

I become, I do page layouts and stuff like that.

And when you do these, the way these meetings work is at these newspapers, you have a morning meeting where all the editors and reporters go in one big room and each section, the business section, the culture section, the front page and so on, they pitch their stories, the editor decides which is going to

go where on the front page and off you go.

But I would always speak up because I didn't know you weren't supposed to.

And so I'd be like, well, what about this?

And what about that?

And I like that. And what if you did this?

And I just became like friendly with a lot of the editors.

And one day I sit down with the photo editor and I show her my photos and she looks at it and her name was Michelle McNally and she like slowly goes through one by one and she closes the book and she goes she's like you're a good photographer she's like I think you'd be you'd be a good war photographer

but I'm not gonna hire you to do it and I was like why not and she goes because you're too normal she's like these guys are fucked up they're on drugs they can't be in a they can only be in a war zone half the time like they've got like they've just got something that's missing that they need that adrenaline

and she was like I don't feel that from you.

And I'm grateful, so grateful that she said that.

And so I was like, well, what do I do now?

And there was, at the Times, I'd become friends with Marissa Mayer and I was talking about going over to Google to go to Google News.

I mentioned this to the editor -in -chief of the business section.

And he said, oh God, I wish we could keep someone like you to be like a reporter because everyone wants to write for the print section.

No one wants to write for the web.

And I just, the words just came out of my mouth.

I never wanted to be a writer.

It had never been anything on my list of things I wanted to do.

And I said, well, I would do it.

And he was like, oh, well, why don't we try it?

And then I was like, oh shit, what have I done?

And so the first day I'm on the job at the New York Times and I'm in this massive newsroom with all these insane people that, you know, back then you were just like enamored by these bylines that you were just like, holy shit.

And my editor comes over and funnily enough, it was Twitter had gone down and he said, Twitter's gone down.

Can you write a blog post about it?

You know, call the company and everything.

And I was like, yeah, yeah, yeah, no problem.

And so I looked at my computer and I Googled, how do you write a blog post?

Uh, so that was my first and then I realized like, oh my god, what have I done?

I'm I found myself in this job that I just don't know what to do and so I just I spent weeks just reading every byline of the greatest reporters and I was like, okay, this is how they write the intro.

This is how they do the quotes.

This is how they do the nut graph and I just figured it out and I made mistakes but like that was my that was my foray into it.

So one day about, I don't know, six months, a year into me being a tech blogger for the Times, I reach out to Apple as, you know, you call and you say, hey, I'm doing the story in this.

Do you have a comment?

And the PR woman that answers, she says, Steve's going to call you.

And at the time, there was a guy called Steve Dowling who was like a very senior comms person.

And I was like, oh, cool.

Steve Dowling? And she goes, no jobs.

And I was like, what?

And I was like, is that normal?

Does that happen? And she goes, sometimes he's going to call you.

He wants to talk to you.

And I've been writing a lot of Apple stuff.

And so he never called.

And that night I went out for dinner with my girlfriend at the time.

And we went for sushi.

And I had like a few sake.

And then all of a sudden I get a phone call from this number in San Jose.

And I answer it. And it's jobs.

And I was like a little tipsy.

And he talked to me for like an hour.

And he just, he just like convinced me not to do this stories in the way I did it.

And I didn't, I didn't, it didn't make any sense, but I, he made so much sense.

And he just, he was like, oh, well you got this wrong and that.

And if you actually, if you look at this, you can, and then the next day, so I wrote the piece and then a couple of days go by, you know, when like you've seen a movie and then all of a sudden you process the movie and then it's like, oh, that makes sense.

I, I played this conversation back in my head and I was like, holy shit.

he convinced me not to do the story that was that was the right story he got you he got me and so john markoff who was a veteran reporter i told him and he goes he just says it's the reality distortion field and i was like what's that and he goes jobs jobs invented it and and every time i would talk

to him from time to time and every time it was the same thing it was like this he had this ability to make you believe that what you were doing was not the right story and that this was the way to do it.

It was, it was a really fascinating thing to see.

How does the reality distortion, because I've heard that so many times, the reality distortion field, never been in it.

You've been in it. What is he actually doing in your opinion?

You're a smart guy.

You're a storyteller.

You're a persuasive guy.

You've been around other charismatic people.

Is it just his aura?

Is it his gravitas?

Is he really good at reframing things?

Is it, is it an intimidation?

What is he actually doing?

And it's one of those things where you hear about and you're like, that won't happen to me.

No, exactly. I was, I, yeah, like he, I, it's hard to describe what he's doing because it's so interesting.

He, he convinces you that you're wrong and you believe it, you know, you, and look, I think there's a part of jobs that we should all admire and respect and, and be, be really amazed by.

But there's a part of him that he was – he could be a real asshole.

Like Walter Isaacson told me this story once.

Jobs was – he presented the iPad, and then what they did back then, they don't do it anymore as much because the media has changed so much.

But what they did back then was they would go around to all the newsrooms around the country, and they would meet with the editorial boards and the reporters off the record in total private, and they would show you the products that they were doing.

So and presidents would do it, too.

And, you know, you would sometimes get invited.

They'd be like, you know, Bush is here or the secretary of state like come.

And it's a huge The New York Times.

It was this massive conference room.

And on the walls were all these photos of all the dignitaries that had come over the last 150 years and business people and so on.

And so we got a call that jobs was coming.

And there was 20 of us that were invited to this thing.

And I end up getting sat next to Brad Stone, who now runs Bloomberg Business.

And Jobs was right next to him.

And Brad was the Apple reporter at the time, and I was the tech blogger.

And there was this moment where he passes – he brings an iPad prototype.

And, you know, we're playing with them and everything.

And I was prodding it too hard.

And he was like, stop it.

You're hitting it too hard, Nick.

And I was like, okay.

And so – but then he says – this is another reality of distortion, Phil.

This actually will make more sense.

He says, we're doing questions and answers and everything.

And then I said to him, I said, Steve, I saw you a couple years ago at Cupertino and you were sitting on, there was three stools on stage and you were on one of the stools and you had just presented the Apple television box.

And I said, you said that you see Apple as having these three businesses, right?

There's the Mac and there's the iPod because that's what it was back then and whatever.

And I said, and then you said Apple TV will be the fourth leg.

So, the stool will become a chair, something like that.

And I remembered it verbatim back then.

And he goes, I never said that.

And I was like, no, you said that.

I'm pretty sure you said that.

And he goes, I never said that.

He goes, I've never said that about Apple.

Apple television's an experiment for us.

We're just playing with it.

It's like, you know, because it wasn't doing very well at the time.

And that was my question.

It was like, it's not doing very well.

Like, did you say that incorrectly?

Exactly. And, and I was like, and I'm sitting there with all the editors and the, you know, and the big, the big mockers at the, at the New York times.

And I'm like, and I'm just like this young reporter.

And I'm like, no, you, you definitely said that.

And he goes, Nick, I never said that.

And I was like, okay.

And so, and then I just like shut up.

And then afterwards, John Markov was there again too.

I pulled it up on my computer and I was, and I watched the video.

I was like, he said it, and he goes, reality distortion field, and that was just it.

And so, what was I going to do, go run around to the 20 people in that room and tell them, say that he made it up?

No, he did what he did, and it worked, and they all believed that that was just an experiment.

Right. Are there any of these guys that you felt like had it all, meaning they have the extreme success, they're the extreme achievers of society, but you know most of the time you look and they're on their fifth wife and they're kind of an ad stories that they're kind of an asshole to work for or that they

screwed somebody over or whatever right like they they have same as this quote you know show me a great man and i'll show you a bad man right like you know there's a there's this stereotype with that was there anybody you met that you were like no this person's actually they had it they did they had

the career success but they also were a good family man or they were actually good to be around they're a good good human being to be around yeah people who you would say they're winning yeah um there was one person and I say was there's two there are other people look I think like there are really

good people that in Silicon Valley they're not the most successful of like you know they're not the worth the hundreds of billions like I love Aaron Levy I think he's a great guy like Dennis Crowley you know a lot of people that I really really admire and like and I think are good people But there was one

person that I was like, oh, you have it all.

And I had met him because I had done these series of stories on the Kindle.

And it was Jeff Bezos.

And I remember spending time with Bezos.

And when I became a columnist at the New York Times, like when I got promoted to be a columnist, there was a guy.

I worked with David Carr who was just a wonderful, wonderful human being who was the media columnist.

and he's since passed away, but he was like, he was everyone's mentor.

He would make time for anyone.

He was just a lovely, lovely person, so smart.

And when I became a columnist, I didn't, the first few columns I wrote, I was like, I don't know what the hell I'm doing.

And David used to smoke outside and I would go down and like hang out with him.

And he said, pick a fight that you can win.

That's what you need to do the first time when you first become a columnist.

So I was flying out to LA for Thanksgiving and I was reading a book on my Kindle back then.

It was like 2010 and 9, 11, 12.

And I was reading a book on my Kindle, it was like three pages to go.

And I was like, oh my God.

And they were like, you must turn off your, put your devices off now and put them in airplane mode and whatever.

And I wanted to finish, so I was like hiding the book so I could finish it.

And the stewardess was like, we are not allowed to take off Sir until you turn them off.

And I was like, it's a calculator.

Like it's not gonna destroy the plane.

And she got very terse.

And I was so angry that when we finally got up to altitude, I wrote a column about just how ridiculous it was.

And it got published like the next day or whatever.

And it was like the most read thing on The New York Times for weeks.

And I was like, oh, I'm picking this fight.

And so I started doing – I went to all these testing facilities because back then you were allowed – there were rules in the FA.

You could use a razor, a tape recorder, a heart monitor, and some other.

So we got all these things.

Sean calls it going to petticoat.

You took him to petticoat.

Yeah, I was in petticoat.

And so we went to these testing facilities, and we did, like, EMP testing, and we put a Kindle.

It's amazing, these giant rooms that, like, and you just have a device, and you can test all the EMPs.

It turns out, like, the razor puts off, like, 100 times more EMPs than a Kindle.

and so I did I just kept writing these stories because people like were so irate about the fact that they couldn't read their kindle or you play on their phone while they were taking off and eventually it got overturned and um and Bezos during his earnings call that quarter was like on the earnings

call was like I want to give a shout out to Nick Bilton for like because it helped his business of course you know and um anyway I ended up meeting with him uh and um Um, and he was like, so smart and thoughtful and just, you could tell was on a different level.

Like he, you could just see like, oh, this is someone who, who never forgets anything who, and he was married.

He was talking to me about his kids and how his, his teenage son still sits on his lap and like, and then I ended up getting, going to a dinner at his house and, um, uh, and And he's, you know, talking about his family.

And like, and I met his wife, Mackenzie, many times.

And I was like, oh, this, he's the guy who has it all.

He's like created this unbelievable business.

He doesn't, from what I could tell, he's not, like, people don't say he's an asshole to work for, right?

I'm sure there were some, but most people like really, really loved working for him and stayed at Amazon for years and loved the culture.

And then they got divorced and he ended up in a very, very different relationship.

so i um uh and now you like he's like this bodybuilding looking like raver so he i think he had it all but for whatever reason he had like this midlife crisis that made him throw it all away i don't know i don't know so that was the one person that had it all i i want to talk about one more thing um

do you want me to tell that that walter isaacson's oh yeah yeah go ahead So Walter told me this story of after the iPad where he had met Jobs in the Four Seasons, I think it was, which is connected to the Moscone Center, and they'd met for breakfast.

I don't know if it was before or after the iPad.

And Jobs had ordered a fresh squeezed orange juice, and the waitress brings it out, and it's not fresh squeezed.

It's got, like, pulp in it.

And he calls her back over, and he says, I asked for a fresh squeezed orange juice.

And she brings another one out, again, that's got pulp in it.

And he just becomes more and more angry about this orange juice.

And at one point, she's almost in tears, this poor waitress.

And at one point, Walter says, like, Steve, what are you doing?

Like, it's just an orange juice.

Like, they clearly don't have, like, non -pulp orange juice because it's fresh -squeeze or whatever.

And he says if she's chosen to be a waitress for her living, then she should be the best waitress she can be.

And it's my job to push her to do that.

And it's like, no, you don't know her backstory.

You don't know, like, where her life has gone and why and things like that.

And, like, and I think that, like, so for all the brilliance, there was a lack of compassion.

And look, we all, I think the thing is, the reality is, like, none of us are perfect.

We're all good and bad.

Yeah, well, do you think you have that?

You're one of the best there is.

do you lack that compassion i mean like are you accused of being an asshole yeah i fucking love when people call me an asshole like i just like i i just don't give a shit but like i what i pride myself on is i pride myself on being very very easy to work with like if if we're doing a creative if we're

right if we're writing a movie together and i'm working with the producers or we're doing a documentary like i am there to make this the best possible and i will never ever ever be an asshole.

And you could never find anyone that would say I would, because I understand that what we're doing is really hard and we're all doing our best.

And like there's the pursuit of creating great creativity.

However, I've picked fights with people as a writer and a journalist and gone after people that makes me into a fucking asshole, quite honestly.

You know, I had a thing when Dave Morin was doing all of his products and startups, Like, I went after him, and then later, I actually later apologized to him because I felt like I was too much of an asshole, and we had, like, a heart -to -heart about it.

And, like, and I do think, like, there's a great line that Bill Keller, he was the editor -in -chief of the New York Times for many years, used to say, and he used to say, I don't believe people should be able to write about other people until they have been written about themselves.

And I learned that when I, people started writing stories about me, and I was like, oof, that feels awful.

Like that sucks. And it was like a moment where I realized like, oh, like, I don't need to be such a dick to people.

Like I can, I can, I can write these stories and I can be honest and I can tell the truth, but I, I need to, you need to have some compassion too.

And I, you know, that was something I had to learn in the beginning of my career.

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All right, back to this episode.

You talk about your time at the New York Times where you're like, we were in this room and then the room had the portraits of all the important people who used to come to us and and try to tell us what they were doing because we were the messengers and we used to kind of shape the narrative out there

and they tried to shape us and we shaped the narrative yeah and there was these people who were you know you recognize their names from the bylines that you had just like so much respect for them do you think that that's still like like does that shit matter at all anymore because for me i'm like if i'm

a founder of a company now i don't i put zero dollars into pr i put zero care and if i can get a press mention it's like so low on the total point compared to how it was 15 years ago when I was building a company that has changed my, my respect for kind of mainstream.

I think Trump really like reality distorted everybody when he started going after fake news and then you started seeing examples of it.

And like, I just feel like the credibility has gone down, but I'm also on the outside.

You're almost, you know, you're, you're from that world.

Do you feel the same way?

Or do you, do you think that's completely misguided?

There's a practical thing of like, you, You can get an audience on Twitter or wherever, and you're like, I don't want you, nor do I need you.

There's two answers to that question.

And the first answer is that I think 90 % of the media is utter garbage, and it is complete and utter ridiculous drizzle that is opinionated and bad for society.

And I think 90 – I think 10 % is people that are working really, really fucking hard to try to do investigative reporting because they care.

And I met those people.

I remember those people at the New York Times when I first started.

And I had – they were people that were making $120 ,000 a year and could be making millions, like working for a hedge – billions.

I don't know, like wherever they wanted.

And they wanted to pursue the pursuit of honesty and setting the record straight and going after these bad people because there are a lot of bad people in the world.

Does that 90 % of the crap include your past employers?

Does that include New York Times?

Everywhere. Yeah, 1 ,000%.

Yes, 1 ,000%. Because I think – because the system – it all broke.

Like it's broken – and I believe it's broken beyond repair for now.

Now, my hope is that, and maybe this is me being delusional, but like my hope is that AI can somehow help fix it.

But I believe that or AI in the hands of people can help fix it.

But when I first started at The Times, like you weren't allowed an opinion.

You weren't allowed.

There was no, you know, there was no social media.

Like there was no Twitter.

Like I was at The Times when Twitter came out.

Like I remember being in meetings in those rooms and I would ask an editor, right, what do you think?

And they would be like, I don't have an opinion on this.

I'm a journalist who comes at this impartially, and all I want to do is report the facts.

And so I think that what happened was you had this – the problem was the internet came along, right?

And you had to – to get to the Times, like I was the first one that – one of the first ones that came in.

I remember being in a meeting once with 40 or 50 people at the Times.

It was this big meeting.

And everyone kind of went around, and they introduced themselves, and they talked about like where they'd gone to school and how they'd ended up here.

I barely graduated high school.

Like I literally had a 2 .1 GPA.

I got kicked out of art school.

And like, they were all like, I was at Harvard and I worked at the Harvard Crimson and I did this and the other.

And I was like, oh, I'm the odd one out here that shouldn't be here.

And like was only here because no one wanted to write for the internet.

And that became, everyone became that.

And I think that like what ended up happening was you had this generation that came in after I left that was, they were the internet people.

They hadn't been mentored.

They hadn't, you know, they hadn't learned the ropes and they didn't, and they felt like they had a right to say, oh, we shouldn't, we should not publish Tom Cotton in the opinion section and we're going to be irate because we did.

That is not the way the world works.

The world works is by listening to other people's opinions.

And like – and I think the reason that so many people in Silicon Valley have veered to the right, which they have, is because the left tells them, oh, you can't think like that, and you can't – and you're stupid if you believe this and so on and so forth.

And I think that, so the whole apparatus is completely broken.

But at the same time, I am friends with a lot of startup founders who tell me that like, oh, we got a profile in the New York Times and we had the biggest influx of customers we've had ever.

Or we got mentioned, you know, a write -up on here or whatever it is and the same thing happened.

And so the eyeballs are still there.

People just don't necessarily trust them in the way that they did.

And I think that, you know, what's interesting is that you have all these new news outlets that come along, like Semaphore and the Free Press and things like that.

And they're trying to get people – they're trying to say we're impartial in the middle and so on and so forth.

But inevitably what ends up happening is as soon as you put that opinion in, the number of listeners or viewers or readers go up, and then the product ends up steering that way.

And so I think that there is a desperate need for something that is – what I think the solution is, honestly, is you don't need a right -wing publication or a left -wing publication.

You need a both. You need a place where there are people who have right -wing point of views and centrist point of views and left -wing, and they're all in there together, and they're debating it, and they're respectful of each other, and maybe they disagree, but they are all there.

And the problem is The New York Times is all left and The Wall Street Journal is all right and so on and so forth, and so you don't necessarily trust any of it.

Yeah, I would love to read the debate.

I think that's a lot more interesting format.

Totally. Two people who each believe or are willing to argue the best case for each side so you can read it.

And I think that's both entertaining because it's sort of a fight, an intellectual fight, but I think it's also more informative because you get both perspectives, sort of steel -manned.

Is there a story you wish you could write, either if you had infinite time or sometimes you get successful and you're like, oh, somebody should do that.

It's probably not worth me doing it, but somebody could do that.

Is there a great story out there that you think somebody should be doing?

I don't know. My dream is I love thinking about stories from all different perspectives, like how, you know, when is a story a documentary?

When is a story a book?

When is it a magazine?

When is it a tweet?

When is it a movie or a nine -part series on Netflix?

And I do – I write all forms of writing.

And I'm fascinated by, you know, there's these different things that are fascinating.

it's like, you know, a documentary is the people from the past talking about – they're in the present talking about the past, right?

A TV series is the story unraveling as you're watching it unravel.

A book is – you get to climb inside – crawl inside someone's head for seven hours and let them understand how visually things smelled and looked and da -da -da -da.

And, like, and so I've always, I want to write a novel at some point.

I think that that's, like, the next thing I want to do.

And so, because I love, I read, I'm a voracious novel reader.

And I just have so much respect for the amount of research that goes into them.

And then they become, but it's, like, it goes back to the beginning.

Like, the magic is you don't know that the people that wrote the novel spent hundreds of thousands of hours researching all the history or whatever it is to do that.

And as far as like a net nonfiction, like I just love stories that are that, you know, that old cheesy saying that like, you know, if it was fiction, you wouldn't believe it.

You know, it's like I really think that those are the stories that to me are are the most the most fun to read and report and research.

You have all these different seasons of life.

You know, you said you in evolutions, you said you want to be a war photographer, and then you accidentally became a columnist and then you became an author.

and even though you've disliked some of the guys you cover, it sounds like there is a lot of admiration still for a bunch of others as well.

Have you ever thought about going into the business world since you've been able to see it so closely?

I almost did this year, actually.

There was a project that I was going to go do, which was a startup in the storytelling space.

Can you say what it is?

I think that what's happening is there's a change coming in Hollywood it as far as how we consume content and short form versus and the way you know there's there are these structures that happen to stories that that we that become norms and so for example in a film screenplay a film screenplay is 120

pages long because each page is a minute and that's why when you look at screenplays they're courier and the certain font because each page shot is usually one minute long and so 120 pages is two -hour movie and so there's a there's a whole system setup there's a book called uh save the cat which essentially

made this world where you you on page one the first person you meet is is your is your main protagonist um by page three you have discovered what the movie is about by page five there's the introduction of the antagonist by page 30 every single movie if you go back and watch on page 30 which is 30 minutes

in it's the changing moment it's the you know it is the joseph campbell like this is when the journey begins and and then by page 90 you've entered this third act and and we've come back around and so on and so forth and um and while every movie is different we we understand that that's the same thing

and i think what what's happened is that that um philosophy has been overused and i think do you remember the movie parasite uh that won the academy award parasite changed it and it wasn't by page 60 it turned into a whole different movie and you were like whoa i've never seen that before and that's

why people i think really loved it and i think what we what we look for in culture is things that are new and different and every once in a while a genius comes along who does it and um and then everyone else copies that and then you got to wait for the next genius to come along to do the thing and um

and i think that the that page one page 5, page 30, page 90 thing is completely, it doesn't work for today's audiences.

They don't have the patience to wait till page 30 to find out when the turn is.

And so in short form, there's like this new philosophy of like one second, seven seconds, nine seconds.

And I think that like, but then they don't know how to tell stories.

And I think that there is a world where, um, you know, we were exploring this idea of like thinking about the new approaches of how to tell long form stories and short form bites and things like that.

And, um, but at the end of the day like the reason i didn't end up doing it is because i just love telling stories and i don't necessarily want to be like a manager meeting with vcs and boards and i'm getting kicked out by jack dorsey how many uh how many copies how many copies of your books have you

sold uh hundreds of thousands of copies yeah over time um i don't i haven't checked in a long time but uh hundreds of thousands and they've been printed all over and why is american kingpin not a netflix like seven part series i can't believe nobody's amazing show it was okay that movie was okay i mean no it

was bad it was bad it was bad yeah it was bad i'm not going to tell you the story but the reason the reason it has not is because i got screwed over on on the film film rights deal so that's the reason why but it may end up in it's still today it still may end up uh may end up there we'll see all right

if i wanted to spend six weeks getting as good as I could at storytelling, what would I do?

Is there a book or is there some process?

Like if I was dedicated, how would I become an amazing storyteller?

Well, if you dedicated, you'd need more than six weeks.

So let's pretend it's...

What would be the first...

What would be the...

What could I do in six weeks?

I got 19 bucks. What do you got for me?

If you... I have all these books on like on storytelling that I read and like...

And they're interesting and like you get a little snippet.

I think the most interesting of all the books I read was when I wrote Hatch and Twitter, I really wanted it to feel like a murder mystery because no one knew what really happened.

And I read a book on murder mysteries, which was unbelievable.

Like you can read any of them, just Google like how to write murder mysteries.

It's a blue book. It's a collaboration where a bunch of murder writers and screenwriters and so on each write a few chapters each.

And there's a few things I learned from that, which one is when you read a lot of books, people forget to describe smells and murder mysteries always do and it really brings you in it's wild to see how it can add this extra layer like sounds smells the noises not just the creaking stairs but the mold

whatever it is, it just creates this sense of story in your brain The other thing is The Save the Cat which is really interesting, even if you don't write screenplays it's a really interesting way of understanding character and so on.

And I read a bunch of screenplay books by like some of the old greats and they talk about characters and things standing in your way and so on.

But I will say for me, the best way to become a great storyteller is to read stories.

And I think one of the things that frustrates me about Silicon Valley and the tech bro culture is everyone's trying to optimize their life for the most number of seconds of this and that and the other.

And it's like what they don't realize is that some of the greatest things that they will learn is from things that have nothing to do with what they do.

So I'm 48 now. When I was 45, I loved listening to piano music.

I've never played before.

I was like, you know what?

I'm going to learn the piano.

And I got obsessed with it.

I learned how to read music for the first time.

Oh, look at you. What is that?

I'm on the Faber method here.

So I'm on book 2A right now.

I'm playing. There's a great app that I do in my spare time.

It's called Notes Teacher.

And you just do it for like five minutes a day.

Just like sight reading practice?

Yeah, sight reading practice.

But I got obsessed, obsessed.

I literally would play two hours a day.

and, like, now I can play a couple of Chopin songs and things like that.

And the thing I—and to me it was just a fun hobby and it was, like, really, like— but what you learn is that, like, they are telling a story and they're telling a story, you know, Hans Zimmer says, like, the notes will ask a question and then the next notes will answer the question and it's, like—and the way Chopin,

like, is just unbelievable when you—if you sit and analyze the music and think about, like, the highs and the lows and the things that are repeated and it's amazing and it started to kind of inform some of the ways I thought about screenplays.

And like, I read as many novels as I can.

I hate nonfiction books.

I can't read nonfiction books, which is funny because I write them.

I just, they're just boring to me.

So I, but I read novels and I love like just studying as I'm reading like, oh, that was really unique of the way they did this.

And I read a lot of like 1950s sci -fi and then I read a lot of like 1930s, 40s, 50s, 60s incredible, you know, like the writers that we all should read.

And you just understand that these stories are about people, not the stories that we think.

It's like the guy who wrote Game of Thrones, George R.

R. Martin, I saw him speak once at a conference years and years ago.

And he said, you know, you could take my story, you could put it in a spaceship and it would still work.

You could put it in present day and it would still work because it's about the relationships in the characters.

And I think that that's what ends up happening is as you watch something, the best stories are the ones where you imagine yourself as the character and then you want to know how you would solve the problem.

If I'm James Bond, how would I get out of this as the drill is about to sever my heart or whatever.

And then you can't figure it out and the storyteller does.

And you're delighted by that because it's great storytelling.

I think that's your secret, by the way.

You're like, nonfiction is usually pretty boring, but yours aren't.

And I think yours aren't because you consume so much content that's on the mystery side.

Yours are page turners.

And so that lateral thinking where you take a skill from one discipline and apply it to another that usually doesn't have it, that's what some of the best business people do as well.

The best hedge fund renaissance is because they took the best AI, machine learning, mathematical prowess and applied it to finance.

And we had Mike Posner on the podcast and he was talking about how he started as a rapper, but all his hit songs are him singing.

And he's not the best singer, but he's like, I am the best writer.

And he sang one of his lyrics and he's like, the rhyme scheme I'm using here, The reason people like that hook and it's catchy is because I'm using a rap rhyme scheme, which no singer -songwriters would typically do.

But that's why my song sounds different because I'm using a rapper's lyrics, but I'm singing them in the way that is rarely done.

But it sounds like you've kind of done that same thing.

No, I think it's totally true.

And look, I think Jobs did this thing where he, you know, computers back then were these nerdy, like, circuit boards.

And he was like, oh, I'm going to marry graphic design with technology.

And so for me, like, I want to marry the style of a novel with a narrative nonfiction story.

And, you know, there's great writers who've done that in the past that I have such, such admiration for.

Whenever I get done reading your books, like, when I get done, each time after I've read American Kingpin, I'm, like, pretty bummed.

i'm like oh i was so like in love with like reading this and i was looking forward to fit or i was looking forward to like i would sneak off to like find the page and see if i can just like read a few uh chapters and i felt bummed that like i was like in this relationship with this book and it's over

now and i would i've like searched so long and hard to find something that could fill that need and like only one out of like 20 or 30 books like fills that need i think i think mastermind was another great book that was a similar topic he did and the author did a great job of a very similar style of storytelling

but in general it's been really hard for me to find things i read a lot of novels but i like reading i like sometimes when i read a novel i'm like i fall in love with this character and then i find out that i have to remind myself the character is not real and i get kind of like bummed about it you

know and so what who do you view as a peer uh or uh someone you look up to or you they do your style of non -fiction storytelling having well just to real quick on the novel like yes they're not real but they are based on reality like every every novelist pulls from the people around them to create the characters

that you're reading so you know it's like what you know if you go do research into like whatever your favorite book is uh your favorite novel like and you look at how they did it if they talk about it they're like oh this is me you know when i was a kid my grandfather used to tell me the stories about da -da -da -da -da -da or like

there was a neighbor across the street so i think they are it is real and it's still people um as far as as um as far as people i admire and i look up to i like i said before i don't really read a lot of narrative non -fiction uh i'm sorry a lot of non -fiction i don't think there's that like i and i

love i have such admiration for people's reporting and and even the writing but this is i i need a story i can't have and so that's what i'm describing i want more like story -driven non -fiction.

I need a story. This is the shit, man.

I just love learning about this stuff.

Well, you had one last question, Sam, and I interrupted you.

Or did you answer it?

Well, it was about, Sean, did you see the documentary on Netflix about, what was it called?

It was with Ilya. Was it Bitfinex?

What was that called?

It was the couple, Bitcoin, Bonnie, and Clyde.

I did a documentary on them for Netflix with chris smith who did tiger king uh that was about this couple that had stolen 5 .4 well they stole 72 million dollars in crypto uh and then were trying to launder it and every they were the only two people on the entire internet who wanted the price of bitcoin to

go down uh and they had every time they were trying to launder it it would double and double and double and double and double and to the point that it was one point at its peak was worth 8 .4 billion dollars and she was that's like wacky uh cringe rapper and he was like a part -time magician investigator and like

it's one of those stories if it were fiction you'd be like yeah this is stupid this had never happened she uh shot she or the the guy ilia spoke at the very first hustle con which is kind of funny oh and then the woman had the new forbes 30 to 30 dude you said listen listen listen the woman heather

she was like a copywriter or something but she wasn't any good and she like dm'd me asking to talk at one of our things or to like do freelance work or something like that and then uh she was kind of a sex freak i had a bunch of friends that like fooled around with her and they were like this woman's

wild man you should stay away like like those types of stories and i was like joking with nick i was like whoever i guess we interact with just like you know maybe 10 of them are gonna end up becoming like amazing criminals uh because for some reason we've been around a bunch of these people like right

as or right before they were committing some huge crime but that was also a good story yeah that was a great story that was such a wild story that they that they went on they went to ukraine and like uh had like fake passports and i mean it was just yeah it's nuts is uh is making a netflix documentary

is there a good money in that or you do it just because it's sick and it's like you know it's art and i'm doing this for art How does that work?

There's not. Look, being a writer, I think, you know, it's good money, like if you can pull it off.

Somebody sent me an article a while ago that you're more likely to become a billionaire than to become a successful writer.

And, yeah, it's like I think the way in the olden days, you know, at Vanity Fair, for example, or The New Yorker, they had these contracts for these writers.

They would get paid hundreds of thousands of dollars a year and they would write four stories a year.

And like – and then they had the house upstate and the place – the brownstone in Brooklyn.

And like it was a different time.

And now, you know, everything has been diluted.

Media has been completely diluted where we have podcasts and blogs and newsletters and mainstream media and all this stuff.

And so the advertising dollars and the revenue dollars, it's not like they've gone up.

It's just they've evenly – been more evenly distributed.

And so for me, I just want to tell stories and I just don't give a shit in what format it is.

And so it's really fun to be able to write screenplays, to write books, to write magazine features, to make documentaries.

And then it all just kind of adds up from there.

I could talk with you for hours, man.

Thank you for doing this.

Thank you so much for having me.

This has been really fun.

We appreciate you. All right, that's it.

That's the pod. That's the pod.

hey sean here a quick break to tell you an ev williams story he started twitter and before that he sold a company to google for 100 million dollars and somebody asked him they said ev what's the secret, man?

How do you create these huge businesses, billion dollar businesses?

And he says, well, I think the answer is that you take a human desire, preferably one that's been around for thousands of years.

And then you just use modern technology to take out steps, just remove the friction that exists between people getting what they want.

And that is what my partner Mercury does.

They took one of the most basic needs any entrepreneur has managing your money and being able to do your finance or operations.

And they've removed all the friction that has existed for decades.

No more clunky interfaces, no more 10 tabs to get something done.

No more having to drive to a bank, get out of your car, just to send a wire transfer.

They made it fast. They made it easy.

You can actually just get back to running your business.

You don't have to worry about the rest of it.

I use it for not one, not two, but six of my companies right now.

And it's used by also 200 ,000 other ambitious founders.

So if you want to be like me, head to mercury .com, open up an account in minutes.

And remember, Mercury is a financial technology company, not a bank.

Banking services provided by Choice Financial Group and Evolve Bank and Trust members, FDIC.

All right, back to the episode.

[The Art of Narrative Non-Fiction: Uncovering the Truth Behind Silicon Valley's Legends]-[We talk to the guy who knows Silicon Valley’s darkest secrets]

📋 Summary

The Craft of Investigative Storytelling

The "Reality Distortion Field" and the Power of Myth

The Duality of the "Great Man"

The Future of Media and Narrative

🎯Key Sentences

📝Key Phrases

📖 Transcript