764: Nick Bilton | Hunting the Dark Web’s Silk Road Kingpin

764: Nick Bilton | Hunting the Dark Web’s Silk Road Kingpin

[00:00:00] Jordan Harbinger: Special thanks to Nebula Genomics for sponsoring this episode of The Jordan Harbinger Show.

[00:00:04] Coming up next on The Jordan Harbinger Show.

[00:00:07] Nick Bilton: "Look at the things we're doing, we're selling these drugs and guns, and having people tortured and," you know, at least they think they are. "All these things that we're doing." He's like, "We've crossed a line a long time ago," and Ross's response is, "I don't believe we have crossed the line. I think we've just moved it."

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[00:01:15] On this episode from the vault, we'll be talking with my friend, Nick Bilton. He's a special correspondent for Vanity Fair where he writes about technology, politics, business and culture, and the occasional crime. He also wrote Hatching Twitter, which chronicles the turmoil and chaos inside Twitter as it grew from a fledgling startup into a multi-billion-dollar company, and it might be a time for an update on that one, man. What do you think? With Twitter going on right now. This is one from the vault recorded quite a few years ago. You'll be able to hear that we were not using the same kind of microphones, the same kind of audio set up and even the same kind of software to record. It's a little bit, that sounds a little bit like a phoner. Probably wasn't quite that bad, but you'll know when you hear it. It's not quite the same as what we put out now.

[00:01:53] Today, we're going to tell the story of Ross Ulbricht. He's a young Texas Boy Scout who decided to build a website where you could buy or sell anything. It's called the Silk Road. Soon became a 1.2 billion drug, guns, hacking tools website, not to mention hitman and murder for hire, all kinds of crazy stuff. Again, the Silk Road, if you haven't heard of it, it is quite a wild tale. We'll hear about that today. It made him the most wanted man on the Internet, and frankly, one of the most wanted men in the United States. Nick researched this story and its subject kingpin Ross Ulbricht so much. I actually think that Nick probably knew Ross at the time, at least better than he knew himself. We'll discuss that process of writing and diving deep into somebody's head and mindset, of course, to create a book like this. And in an age where technology consumes every moment of our lives, people need to know how their ideas could be used for both good and bad, positive and negative. And this story is really the perfect parable to teach that.

[00:02:47] So get ready. Enjoy this episode from the Vault here with Nick Bilton.

[00:02:56] Nick, thanks for joining us, man. Super interesting stuff you've written recently here.

[00:03:00] Nick Bilton: Thank you so much for having me.

[00:03:02] Jordan Harbinger: Now, this book kind of freaked me out, right? Because Silk Road, fascinating and cool, and you're thinking about this kid, Ross Ulbricht, and people on the Internet have all these differing opinions. "Oh, they just made an example out of him. Yeah. He's this innocent Internet entrepreneur that kind of got taken away. The best years of his life, he's going to be in prison forever, and he just made a couple of simple mistakes." But then when I read this book, when I read American Kingpin, I'm thinking, "This guy, he might have been good in the beginning, but he certainly didn't end up one of the good guys towards the end."

[00:03:35] Nick Bilton: Yeah, I mean, I think you're completely right. I mean, I think that he kind of embodies — I've been covering Silicon Valley for more than a decade and he embodies a lot of the CEOs I covered for a long, long time. You know, Ross was the sweet kid from Texas, Austin, Texas, who grew up in a family where, you know, rather than talking about football and whatnot on a Sunday evening around the dinner table, it was libertarian politics. And he got super into that concept of this idea that the government shouldn't be able to tell people what they can and cannot do, and decided to start a website called The Silk Road, where you could buy and sell drugs without having to worry about being arrested for that or anything bad happening.

[00:04:12] And the site explodes, essentially becomes a phenomenon, and by the end of it, you know, while it may have started with these altruistic libertarian philosophies, Ross thinks he's having people killed. He's selling poisons, disgusting selling body parts, all these things that were not what the ideals in the site were from the start.

[00:04:32] Jordan Harbinger: Yeah. He's almost like a pathetic figure in the beginning, right? He is this dork kind of kid who lives in a basement and has a garbage bag full of old hand-me-down—

[00:04:41] Nick Bilton: Two garbage bags.

[00:04:42] Jordan Harbinger: Yeah, two garbage bags.

[00:04:43] Nick Bilton: Yeah. He has, one is his clean clothes and one is his dirty clothes. That's literally everything he owns right there.

[00:04:48] Jordan Harbinger: When you meet somebody like this in real life, usually you're thinking, "Wow, you're essentially a homeless person that, temporarily anyway, has shelter." And you just think, "How is this person going to make anything out of himself?" This guy was a genius though in many ways, and the potential went towards something that just spiraled wildly out of control.

[00:05:06] Nick Bilton: Yeah, I mean, he's a genius in numerous ways. I mean, he decided when he was going to start, you know, working on the website, he didn't have, he had never studied computer engineering in college or anything like that. He wasn't like Mark Zuckerberg who had gone to school and studied any of this stuff or any of the other entrepreneurs that built these companies. He just taught himself and Ross ended up, essentially when he launched the site, he had grown his own magic mushrooms. He had rented a small little place in the outskirts of Austin and secretly grown his magic mushrooms there.

[00:05:37] And even that is really hard. You know, I spoke to people who've done it and when you try to do it in bulk like he was doing, it's not an easy thing to do. And then, he built the site, he did the front end, the back end, he did the UI, the design, the marketing, everything. That's not an easy task to pull off. And like you said, you know, it's funny when you kind of think about where Ross ended up and where he is today, you can see that this was kind of the kid that we all knew in college. The weird guy that had these weird philosophies and had he not gone off and built this drug website, there's a chance that he could have just ended up going and getting a pretty standard job, or even ended up going and working for the government and doing the thing that he hated. And of course, he went in a completely opposite direction, and I think in a direction that he never thought it would end up taking him.

[00:06:20] Jordan Harbinger: It's weird. I've read this book and I thought, "There's a good chance that you know this story and maybe even this kid better than he knows himself for that period of his life.

[00:06:32] Nick Bilton: It's interesting because as a reporter who's covered stories from, you know, kind of one-foot view on a daily, if not hourly basis, and then reporter who's written books several years after the fact, you get a completely different perspective when you do that. You get to patiently sit back, go through all the evidence, all the research, and the thing with this book that was kind of astounding was the amount of information that Ross had left in his wake as he had built the site and run it.

[00:06:58] For the better part of three years, literally every single communication he had with his employees or with anyone related to the site was captured on his computer in the chat logs and emails. And I was able to get access to all the stuff, including photos and videos, and then got access to his social media profiles and all the things that were on there. And working with the research, we kind of built this database that ended up including — I'm not, you know, just saying this — it's literally millions of words, of different pieces of information. And that stuff all came together and showed this version of this person and actually showed him changing and morphing over time, going from this kid who was like, "I really truly believe this thing I'm building is going to make the world a better place." And then, by the end of it sanctioning the murders and paying for the murders of people that have wronged him on the site or that could potentially, you know, lead to its demise.

[00:07:48] Jordan Harbinger: First of all, I don't even remember chats I had last week, so the fact that you had chat records and email records from this guy from so long ago — the amount of insight you get into someone's mind is tremendous. It's certainly more than you would get with trying to look back at your own 20/20 hindsight, or maybe even 20/15 hindsight, right? Because everything's tainted by emotions. You're looking at the actual raw data here. You can't really deny anything. How do you think the process begins for someone to go from ideologue idealist, a libertarian, "Everybody should be able to do what they want with their body. Recreational drugs are healthy for your psyche," to, "Yeah, let me pay some Hell's Angels 50 grand to torture/murder some guy who I think stole from me, even though I have no proof?"

[00:08:36] Nick Bilton: Look, I think that one thing that happens is, in traditional instances, in traditional business, things don't change that quickly. You kind of open up shop and more customers lead to more customers and so on and so forth. And if you're lucky, you're successful, there's a very, very slim chance that you reach a huge audience and grow to become a big entity. With the Internet, it is incredibly different. You can build a business, a website with a few people that can take off in seconds, and when it does, it goes from one person using it, or a dozen people using it to a hundred million people using it. And doesn't necessarily mean that you build a successful business. I mean, Twitter is a perfect example of that. This is a company that's got over 330 million people on it, and it's still struggling to figure out what it is and where it's going and if it's going to survive. But a lot of these instances it happens, you know, almost like a rocket ship taking off. And that was what happened with Ross Ulbricht and the Silk Road.

[00:09:32] He built the site, he had a few trickles of people coming in and using it, buying the mushrooms. He'd grown the weed that he was selling, things like that. And then, more people started buying and selling on the site. And then, on June 1st of 2011, Gawker ran an article — Adrian Chen, a reporter from Gawker, and the article was talking about the Silk Road, this website where you could buy and sell any drug imaginable. And it exploded from that point on. It was picked up in every news site on the Internet and around the world — NPR, local news, you name it. And from that point on the site became essentially an instant phenomenon and people had realized, "Okay, well, whoever had started it, if they hadn't been caught by now, then they weren't going to be caught, and if the site was still going, and so people felt emboldened to use it.

[00:10:18] And next thing, you know, they're selling, they're allowing people to sell guns, then it's poisons, then it's bomb stuff, then it's how to build your own drug laboratory, then it's cyanide, then there's discussions of selling livers and kidneys, there's hacker tools — I mean, it was just endless the number of things that you could get on there that you couldn't get very easily in the real world. And there were all these repercussions from that. And you know, for Ross, I think from a personal standpoint — and you can see this when you kind of read the chats, as he starts to change — he starts to kind of become more aggressive in certain instances. He still remains like a sweet guy, but it's so clear that it goes to his head.

[00:10:55] And it's funny because you know, in the beginning when I first found emails of his from when he was younger, when he was in college or when he ran a business before — it was a bookselling business — he never cursed. He would always write the word fudge. Like, "Oh fudge, I just did this." It was very hokey the way he spoke and wrote. And even as he is running this website and ordering the hits of these people, he's still using those words. He's like still saying, "Oh fudge, I wish I hadn't had to kill him," you know? His personality is changing in the respect of he is becoming more emboldened. He's completely fearless at this point. He doesn't believe there's ever a chance he can ever be caught, but at the same time, he is still got these quirks that remain the same all the way through.

[00:11:38] Jordan Harbinger: That's so bizarre, and it kind of speaks to that separation that we can have when we're interacting with people online.

[00:11:45] Nick Bilton: Without question. There is someone who goes on Twitter and you know, tweets at me or you or anyone and says, "You're an X, Y, or Z piece of X, whatever," they would never, ever, ever say that to your face. They have no connection with the fact that the words they're typing into a computer are affecting a human being on the other side of that screen.

[00:12:04] And I think that the same exact thing was happening with Ross. He had no concept that the drugs he was selling were enabling, you know, teenagers and kids that would not necessarily have been able to get access to some of these things to get access to them. You know, there's a story in the book where Ross goes camping for a weekend and he enlivened by how well the site's doing. He's making tens of millions of dollars in commission fees on all these drug sales. He meets a girl in falls in love. And over that same exact weekend, there's a kid in Perth, Australia who gets access to this drug called N-Bomg, which you could never have gotten in Perth before. And I spoke to law enforcement there and they said that you could never have gotten it if it wasn't for the Silk Road because it connected you with these labs in China that make these things called N-Bomb and other synthetic drugs. And the kid had an adverse reaction and died. You know, for Ross, I don't think he had any concept of the negative effects of the website. He only chose to see the good side because he was behind a computer. That was it.

[00:13:01] Jordan Harbinger: And you see these sort of attempts for him to rationalize things that are going on and how he becomes more and more isolated from the women that he's dating. And his friends can't know about it. He's even having people help code the site that they don't know exactly what they're creating. So he becomes more isolated and in that sort of weird sphere of isolation, he starts to change in probably ways that he doesn't even recognize, and yet he doesn't seem to notice that it's happening because all of the people that are doing these things are super far away. He's never met them. He's never spoken with them in his libertarian, super-libertarian ideology. It also is their fault. So he's able to isolate himself from that and just kind of go retreat back into the ideology in a way.

[00:13:48] Nick Bilton: Yeah, the ideology was a justification all along, and I think that that's where I completely can understand where Ross is coming from, and I understand the arguments in the defense of him and the site when it comes to certain aspects of it. I do believe that certain mild drugs should not be illegal. I think it's just ludicrous. You know, this is one of Ross's original arguments. When you look at the number of people who die from eating Big Macs every single year, tens of thousands of people from heart disease and so on, or the number of people that die from alcohol. And then you compare it with the number of people who die from taking magic mushrooms, for example. There's only, literally, in the last 30 years, there's only two recorded instances of people dying from magic mushrooms, and those are not even proven to be from the actual magic mushrooms. Yet, if you get caught dealing that in Texas, for example, dealing magic mushrooms, you can go to jail for life. And I think that's insane, and I think that's part of the broken system, and I do agree with him on that.

[00:14:40] Where I don't agree is that things like heroin and fentanyl, last year alone, more people died from heroin and Fentanyl, the synthetic version of it than died from gun deaths in America. And I don't think that those things should be legal. And I think that we have a responsibility to society to stop them. Is the war on drugs working? No, it doesn't work in the way that it does, but that doesn't mean that these things should be legal. And I think that that's where there was this huge disconnect with Ross too, that he was never able to see that these drugs that he was selling were having incredibly negative effects on people's lives. He was just, in his mind, he thought he was saving the world from the tyranny of government and the rules that exist, and that was it.

[00:15:19] Jordan Harbinger: Have you ever spoken with him? I mean, I would imagine he's kind of literally on lockdown. Are you able to get in there at all and talk with him?

[00:15:26] Nick Bilton: No, I didn't speak to him. I spoke to his mom a little bit on the courthouse steps and I saw him during the trial. And for listeners, that's not giving away the ending, believe it or not. I didn't actually need to speak to him, like you said in the beginning, you know if I would've sat down with him and said, "Hey, Tuesday, the 14th of June in 2013, you ordered the hit of someone, what were you doing?" A, he probably wouldn't remember, and B, he's not going to tell me because he's in the middle of an appeal process and so on. And those chat logs, when you kind of take those chat logs, you take thousands of photos. I had access to the videos. His social media posts, which all happened concurrently, you can see exactly where he was and what he was thinking, and he had diaries that he kept on his computer. He would write online about dreams he'd had. I mean, he kept probably the most robust amount of information online in a digital form about himself than any single person I've ever written about in my entire life.

[00:16:21] Jordan Harbinger: You're listening to The Jordan Harbinger Show with our guest Nick Bilton. We'll be right back.

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[00:19:29] Now back to Nick Bilton.

[00:19:32] It seems like a strange contradiction because here's this guy that uses Tor and these encrypted web browsers, and all of the Bitcoin is all the payment system. He's moving around. He pays for things in cash, but this jackass can't get a Moleskine and write things down, or he's in live, chatting with his criminal business partner, every single thing that's going on all day long. I mean, how do you reconcile that level of carelessness?

[00:19:59] Nick Bilton: You know, for all of his genius, there was also stupidity and hubris I think was actually the biggest downfall. A lot of people say, "Oh, he went to jail for the drugs and so on." I don't agree with that. I think he went to jail because of his hubris. I think he could have, at the end of this all said, "Look, I screwed up. I made a mistake. It got carried away," and instead he decided that he was going to fight in what he believed, win. You know, I don't think that he would've ever thought that he would be caught. There's a couple of conversations he has with some of his employees.

[00:20:27] One employee in particular, this guy, Variety Jones, who is an incredible character in the story, he has this conversation where he says, "You know, I will eventually be able to unmask myself as the Dread Pirate Roberts," and the Dread Pirate Roberts was Ross's pseudonym on the Silk Road, "Because I will eventually prove that legalizing drugs is going to make the world a safer place." So he actually truly did believe that eventually so many people would be using the site and it'd be making so much money and drug overdoses would reduce and so on. That he would be able to come out and say, "Hey, I was me all along." Even if this thing would've grown to be the biggest drug system in the entire world, that would not have proven to be correct, because I think what we're seeing is that the Silk Road and other drug websites like it are actually contributing to more overdoses than in the past.

[00:21:10] But at the same time, I think his hubris was — he made these dumb, dumbest mistakes. You know, in the very beginning when he starts the site, he goes and posts on a forum and actually for the first two seconds, uses his real email address, and then goes back and quickly deletes it, but doesn't realize that it's stored in the server. And another thing he does is he keeps these chat logs on his computer and he thinks that his computer is encrypted, but his password is so simple. It's purple orange beach. It's not like 692-7/£/#/ you know, it's just a word that a computer could crack in a couple of weeks. And so there are all these kind of hypocrisies and the things that he does, and those are the things that his arrogance, I think, allowed him to do them. And that was what ended up being the thing that he fell to.

[00:21:52] Jordan Harbinger: That's unbelievable. First of all, do you go in chronological order researching? I'm curious about your process here because you ended up with an absolute pile. There's a whole library full of chat logs, transactions, and things like that. Not to mention the research you have to do just on his life in general. What's the process of even beginning to triage all that information?

[00:22:14] Nick Bilton: Well, it's interesting because I have a researcher I work with. She's amazing, and she was able to help me. We found stuff. She found stuff that I couldn't have found online using online databases and Wayback Machine and all these different things. There were people she connected to that a lot of the times when you're trying to connect these people that you want to interview, you go to them and you figure out through social media, through Facebook, like if you have a mutual friend in common. And if you don't, you figure out someone that does, and then you get an introduction, and a lot easier to talk to them. And so that's something that she did and we ended up interviewing at least over a hundred people. But for me, it's a process of getting literally as much stuff as I possibly can. And I know that I am completed my research when I get to the point that I am telling people that I'm interviewing things that they didn't know. And that usually takes for a book about a year or so.

[00:23:04] And because the book is written kind of like a novel, it's very narrative, non-fiction like, and I go to the places where these things happen. So if there's a photo of a restaurant, I figure out where the restaurant is. I go to the restaurant, I try to order the same food and sit in the same seat, and it's a little OCD, but then I can describe what that seat feels like or what that sushi tastes like, or that coffee. So I go to the places. I got to spend a lot of time with law enforcement. I got to see where the drugs come in Chicago, follow the trail of all these different drugs that come in through the normal flights across the tarmac to the big sorting facility, see the conveyor belts, meet the dogs that do the drug-sniffing. I mean, everything. And it's just, it's a tremendous amount of stuff and you just kind of have to keep it in your head and organize it that way. And the best way I describe kind of the writing process is if you imagine you have like a 10,000-piece jigsaw puzzle, you don't start in the left-hand corner and start putting it together that way, at least I would not. You start kind of trying to find a couple of pieces that stick together and eventually they all come together by the end. And so you have — the writing process is like, I'll start on chapter 72 and then I'll find myself needing more information. So I'll go to chapter 34 and work on that, and one and seven and bounce around in that respect.

[00:24:17] Jordan Harbinger: Yeah. It seems like just a tremendous amount of work in an organization. I feel sorry for your researcher. Obviously, she's born for this.

[00:24:24] Nick Bilton: She used to work for the DNC actually, and part of her job was to find good and bad things on Congress people.

[00:24:29] Jordan Harbinger: Yikes. Speaking of email hacks and chat logs, right?

[00:24:32] Nick Bilton: Yeah, exactly.

[00:24:33] Jordan Harbinger: So going back to Ross, and — I mean, he's in prison for the rest of his life. There's zero chance he's going to get out, pretty much, I think, given the amount of things that he's been convicted of here. Do you think that this was a slow process of him turning into a monster, or do you think that it happened quicker than you would've expected?

[00:24:55] Nick Bilton: That's a great question. I think it was both slow and fast. I think that he didn't believe that he was turning. There's a great conversation between him and his employee, Variety Jones. And Variety Jones was essentially his conciliar. He was the guy he went to if he was trying to figure out if he should have someone killed or if he should do this drug deal for a kilo of coke or, you know if there were problems on the site — and there were a lot of problems on the site, what he should do about them.

[00:25:20] One of the big problems that was kind of comical actually is that everyone on there is selling something, some illegal contraband, but they don't actually all like each other. And so the weed guys are like, "Well, I don't want anything to do with those gun people because I think guns are terrible." And the gun people, like, "I don't want anything to do with the heroin people because they're just a bunch of addicts and bad people that sell heroin." And so there were like problems like that. There were hackers that would try to take over the site and Ross would've to pay a $100,000 ransom and Variety Jones was the guy who helped him come up with the solutions for these problems. But there's a great conversation where pretty far in a couple of years into running the site and Variety Jones mentioned something about them being drug dealers and bad people.

[00:26:02] Variety Jones and Ross got along very, very well and Ross kind of snaps back and he's like, "What are you talking about? We're not bad people." And Variety Jones is like, "Of course, we are. Like, look at the things we're doing. We're selling these drugs and guns and having people tortured and you know, at least they think they are. "All these things that we're doing." He's like, "We've crossed a line a long time ago," and Ross's response is, "I don't believe we have crossed a line. I think we've just moved it." And so for him, I think that he believed all along, or at least he justified all along, that the things he was doing were not bad. And they weren't wrong. And that it was the price he had to pay for greatness in the same way that Steve Jobs thought being an assh*le to his employees was the price he had to pay for greatness. And I think that Ross just kind of was oblivious to the fact that he was actually doing some really, really bad stuff.

[00:26:49] Jordan Harbinger: It just seems so unbelievable, and I'd like to think, "Wow, you know, I wouldn't have done that. This couldn't happen." But it's also kind of scary because you see him starting a business essentially, and it's working and he's living pretty large, and he's able to accomplish goals that most people with his ideology have only dreamed about. People are giving him a lot of credit for it, right? He's this legendary online villain/hero to the people using the site. Is it fair to say he was one of the most wanted men in the world at one point?

[00:27:22] Nick Bilton: I think he was the most wanted man in the history of the Internet at some point, without a doubt. I don't know about the most wanted men in the world, because I'm sure that there's some people out there we don't even know about, especially some ISIS and Al-Qaeda folks.

[00:27:33] Jordan Harbinger: Sure.

[00:27:34] Nick Bilton: But he was without question the most wanted man in the history of the Internet. And the thing that had happened with him was he had a point where he actually believes that — he has a conversation with his girlfriend. They get back together and his girlfriend, of course, knew about the site in the beginning and that was why they broke up. She has no idea. She hasn't been on the site. She has no idea all the bad things that are happening, but she says to him, you know, she's a born-again Christian. She tries to convince him to bring God into his life because she thinks that that's going to be the solution that's going to get him to stop doing the site and to realize the error of his ways. And his response is, "I don't need God." He essentially says to her, "I think that a man can be his own God. And I think that I know what's right and wrong and I don't need anyone else to tell me." And he was essentially saying like, "I believe I'm God in this world that I've created."

[00:28:16] And he was, you know, he was the person who decided who lived, who died, who was allowed in, who was allowed out, what you could sell, what you couldn't, how much commission he charged, and he was on track to do a billion dollars in sale that year that he was eventually caught and the numbers had just continued to grow and to himself, he was unstoppable.

[00:28:34] Jordan Harbinger: Do you think that he would've just continued on forever? Do you think at some point he thought, "I'm going to retire"? Because he didn't buy anything. It's even more strange.

[00:28:42] Nick Bilton: No, it's a really great question. It's interesting because you know, the people that are out there still defending him, and they're quite a number of them. They liken him to the CEO of Craigslist or eBay or something like that, that there are bad things that are sold on those sites, but those people don't go to jail. And I think the huge difference is that there's negligence on the part of those people of those companies that do sell those things. But there's not an intention to do that. You know, I spoke to one of the founders of eBay about this, because I was curious. And they were saying, "Look, you know, when we first started, we had no idea someone would come on the site and try to sell drugs. We had to institute policies to ensure that didn't happen. And then when people started selling guns, we had to institute PO policies to ensure that didn't happen and so on and so forth." So it was a process of eliminating those things. Whereas with the Silk Road, the intention, the entire intention was to sell those things, and the entire system was built to ensure that people didn't get caught. There was Tumblrs to ensure that your money couldn't be traced. There were tips on how to get certain drugs through the mail, or how to create a dead drop, which is where you leave things in certain places for people to get them. You know, the entire intention was to subvert the law and to get around the government, and so it's not necessarily a very valid argument in my point of view.

[00:29:50] And as far as the question of if he would've quit, he had this goal, and it's bizarre that he had this goal, but he had this goal and he told a few people about this. He actually told people in the real world about it, but he also told his employees on the website that he wanted to be a billionaire by the time he was 30 and when he started the site, he was in his mid-20s. If he hadn't have been caught, he would've gone to that point pretty quickly because the value of Bitcoin was doubling, tripling on almost like a daily basis. So if he had a dollar in his Bitcoin wallet one day it would worth two dollars the next and four dollars the next, and so on. And I wonder if he would've gotten to that point and then he would've quit if he would've been unable to walk away. The irony, something I'm sure that he regrets, is that if he would've walked away literally two weeks before he was caught, he would've gotten away. Even if they knew who he was, they would never have been able to charge him. And he would've gotten away with tens of millions of dollars.

[00:30:41] Jordan Harbinger: Yeah. He could have just wiped his laptop and been like, "I'm staying in Thailand. And I'm going to launder this.

[00:30:46] Nick Bilton: And they would never have been able to prove it was him. He could have said, "Well, I didn't register that account, it was somebody else." Or, "I have nothing to do with it," because they had to catch him red-handed with his hands on the laptop, logged into the site to be able to prove it was him.

[00:30:57] Jordan Harbinger: Geez, high bar. I mean, the law enforcement officers that were chasing him must have just been sweating bullets the entire time.

[00:31:04] Nick Bilton: They told me they didn't sleep for weeks. I mean, that's another aspect of the story that's fascinating. I mean, if you think about the book, it's really a book about ambition. That's a story of ambition of people trying to be successful and doing it at all costs. You know, when you kind of look at the law enforcement side of it, you have essentially four or five main groups around the country that are trying to figure out who this, the Dread Pirate Roberts, the founder of this Silk Road is. You've got the Department of Homeland Security in Chicago, you've got the DEA in Baltimore, FBI in New York, the IRS in New York, you've got local and state police, and then a secret service agent that's part of this DEA task force. Two of the people end up turning bad. The DEA agent, this guy Carl Force starts selling information to the Dread Pirate Roberts about his case and starts bribing him for Bitcoins. The other secret service agent seals over a million dollars in Bitcoins during an arrest and blames it on the person he arrested, and it just becomes, the story just becomes insane after a little while where it gets to the point where you're like, "Are you kidding me? This is what's happening?"

[00:32:03] Jordan Harbinger: Yeah, we see the secret service agent, essentially, they're kind of keeping one of the informants incognito. They rob his Bitcoin wallet or his blockchain wallet, and then that causes Ross/Dread Pirate Roberts to think, "I better kill this guy because he's stealing from me."

[00:32:19] Nick Bilton: And then he hires the DEA agent to kill the guy because he thinks the DEA agent is South American drug smuggler. I mean, just even saying these things out loud is just insane. And it turns out the DEA agent fake kills the guy and then takes the money that he was supposed to give back to the DEA for the murder and keeps it, and you know, it's just crazy. And then, you know, there were these other bizarre little parallels that happened like Ross, when he was started the website, he got really into the TV show Breaking Bad. And so he would sit there, you know, half naked in this room of chemicals and drug equipment growing shelves full of magic mushrooms in secret with cardboard taped to the doors and the windows, so no one could see In, watching Breaking Bad, and when he's finally caught in this library in San Francisco, he gets caught trying to download a conversation about the last episode of Breaking Bad because the grand finale of the show had happened the night before. And that was the whole reason he went to the library in the first place.

[00:33:15] Jordan Harbinger: This is The Jordan Harbinger Show with our guest Nick Bilton. We'll be right back.

[00:33:20] This episode is sponsored in part by Athletic Greens. Jen and I take Athletic Greens every single day. Add a little scoop of Athletic Greens to a bottle of water. Shake it up, drink it up in the morning. Each scoop has 75 vitamins, minerals, whole-food sourced, superfoods, probiotics, and adaptogens that are high quality, and your body will actually absorb. It's a quick and easy way to make sure we're getting all the nutrients we need. Athletic Greens is like all-in-one nutritional insurance, and it's cheaper and easier than getting all the different supplements yourself. No GMOs, no nasty chemicals, no artificial stuff in there. I've tried a few different green powder supplements and usually you got to like put it in a smoothie because it tastes disgusting. With Athletic Greens, the flavor is surprisingly good, not so good you'd think it's not working. It just got that slight green flavor, not bitter, not overpowering. Throwing a scoop with water. It's good by itself.

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[00:36:50] If you like this episode of the show, I invite you to do what other smart and considerate listeners do, which is take a moment and support our amazing sponsor. All of the deals, all the discount codes are in one place, jordanharbinger.com/deals. You can also search for any sponsor using the search box on the website over at jordanharbinger.com. Thanks so much for supporting those who support us. It really does keep us going and makes it possible to continue creating these episodes week after week.

[00:37:16] Now for the rest of my conversation with Nick Bilton.

[00:37:20] Of course, he's watching Breaking Bad and instead of, "Yeah, science," it's the, "Yeah, JavaScript," or whatever sort of encryption crap he's using. Do you think that this can happen to anyone? I mean, do you think, look, this isn't just youthful or this is maybe just youthful folly? This type of corruption of the brink can happen to anybody who ends up with this type of success this quickly or something like that.

[00:37:42] Nick Bilton: No, I don't think it can. I think that it's a specific personality. I think that there are a few things that come into play. One is he had a family that loved him. He had parents and siblings and cousins and aunts and uncles, and so on. But he became so insular he wasn't telling about what he was doing, right? And so, he didn't have — his girlfriend kept saying to him, "You shouldn't be doing this, you shouldn't be doing this," in the early days of the site, before it really kind of got out of control. He chose not to listen to her, and he chose not to listen to another friend who knew about it.

[00:38:12] And I think that the thing that I have found covering the biggest CEOs in the world for so long when I used to be at the New York Times and now Vanity Fair and interacting with them is the ones that are — the most successful, not in a financial way, because I don't think that is the key to success in any way, shape, or form, but are the most successful in feeling that they have accomplished something that they've contributed and so on — are the ones that have a family and that's more important to them than the thing that they're creating. The thing they're creating is fulfilling and it's important, but it's not more important than the people around them that they care about.

[00:38:45] And the other folks I think, that are willing to do anything at all costs to win, there's never going to be anything that they will win at because they're going to need more and more and more. And the perfect example of that is, you know, Donald Trump wants to be more famous and more famous and more famous, and there's no amount of fame that will ever satiate his appetite for feeling loved by this fame. Kanye West is the same way. A lot of CEOs in Silicon Valley are the same way as far as their success. It is a personality type that is able to build a huge business. It is the diversions of personality that decides that they're going to do everything at all costs to win and won that understands that this is not everything.

[00:39:22] Jordan Harbinger: What about the parallels, if any, between Ross and Silk Road and the founders of Twitter? Is there a link between personality change and success that you've identified here?

[00:39:33] Nick Bilton: Well, I wouldn't just say with the personalities of Twitter, but I would say with a lot of personalities in Silicon Valley. It's interesting because Ross, he read all those Ayn Rand books, all the Valley CEOs read. On Facebook, he quotes the same libertarian quotes, like "Ask forgiveness, not for permission," all these kinds of bizarre Ayn Rand quotes that I've seen, you know, founders tweet or post on social media. And the way that he ran his business was very similar, you know, to what the way these guys ran their businesses, defiant and recalcitrant and a point of pride that they are willing and capable of making decisions that could harm other people in order to save the business. That to them, to all these folks is a point of, "Okay, well, I'm doing the right thing and I'm the only person that can make this decision." And I think that that was a huge similarity between Ross and all these other CEOs.

[00:40:22] Jordan Harbinger: It seems like a little bit of a dangerous slope because when I read this, I thought, I would never do this. I just don't have the ideology really to back it up. It seems like it starts with the ideology and then you have to almost have quick success that you can't really handle or kind of acclimate to in order to have this. It's almost like a snapping point at which you just, you become somebody who's totally different, and it's not even just your dark side coming out. It's almost like you're becoming someone else. What do you think about that?

[00:40:48] Nick Bilton: I don't think you're becoming someone else. I think what happens actually is — so in the Twitter book, which was the story of the founding of Twitter, Hatching Twitter that I wrote, I remember this a point at the penultimate chapter, the last four chapters are essentially the closing of the fourth co-founders, and the second to last one is Biz Stone. And Biz Stone is incredibly sweet, kind, and thoughtful individual, grew up with a lot of hardships and I think was molded in those. The last chapter is, of course, of Jack Dorsey.

[00:41:16] And I remember saying to Biz, you know, "You grew up with no money. You know, you were literally on food stamps. Your mom gave you a bowl cut haircut once a week by literally placing a bowl on your head and snapping the scissors around to make your hair look that way." The Twitter story is four friends who accidentally create this thing two become billionaires and two do not. Biz is one of the folks who doesn't, but he still ends up making quite a bit of money. He makes tens of millions of dollars in the IPO. And I said to Biz, "Did it change you?" And he said, "No." He said, you know, "The money without a doubt didn't change me." He goes, "The thing I've learned about money being in Silicon Valley is that it doesn't change who you are. It only magnifies who you are. It magnifies the good things about you and the bad things."

[00:41:58] And the next chapter in the book is the last chapter which goes into Jack Dorsey. And I think for Jack, he had always wanted to be perceived as someone important who had created some great things and so on. In the same way that Donald Trump needs to be famous and there's nothing that can satiate that. There's no amount of attention that could satiate that for Dorsey. And he ends up taking credit for everything that, especially things he didn't create, and he ends up alienating everyone as a result of that. And I think that the money only made him do that more. And so if your question is, "Could I go along, Jordan, and say, 'I am going to start this drug website because I think that we should be legal. Will I end up ordering the hits of people by the end of it and being okay selling AR-15s to teenagers?'" No, you would probably get to a point where you're like, "Wait a second. This thing's getting a little out of hand. I should probably have some rules on here because anarchy does not work on the Internet," and I think that you wouldn't get to that point.

[00:42:58] Jordan Harbinger: Yeah, I would like to think so. And that's kind of what scared me a little bit about the book was you look at all his mistakes and you kind of go, "Well, I wouldn't do that. Well, I hope I wouldn't do that."

[00:43:09] Nick Bilton: I think that you wouldn't do that if you wouldn't do that, if you had no money and no power. There's a great Abraham Lincoln quote, and I'm going to bastardize it a little bit here, but it says something to the effect of, "To really see a true man given power, that's when someone's true personality will come out," and I think that that's evident in the Silk Road more than anything I've ever written about. But it's evident in Silicon Valley every single day.

[00:43:33] You know, when Travis Kalanick and his friends started Uber, they believed that the taxi system was broken and they were completely right, and they believed they were going to make the world a better place by creating a world where you didn't have to wait for a taxi for five hours at the airport, or, you know, have a taxi driver speed off because they don't want to go to Brooklyn on a Friday night or whatever it is. And that was the original concept. And then fast forward five years and 70-billion-dollar company later, and there's this fear by Travis and his co-founders and board members and so on, that they could be usurped by someone else. They could be overtaken by someone else. And they do anything they possibly can to win, including breaking more laws than I can count. Telling the DMV that they're not going to pay attention to their rules, you know, creating fake apps that throw regulators off their scent, all these things — screwing over their employees, screwing over drivers, cutting the amount of money they're going to pay them.

[00:44:31] And in the end, sure, Uber is amazing because drunk driving is down and we can all get a car whenever we want, but at the same time, they st ended up becoming the thing that they were trying to stop. And I think that's the exact same thing that happened with Ross in the Silk Road. You know, he thought the government was terrible because of what it did to people who dealt drugs, and in the end, he ended up doing the exact same things.

[00:44:53] Jordan Harbinger: Nick, this has been brilliant and a little scary depending on how introspective one might be.

[00:44:59] Nick Bilton: Should we go off and start a dark web website, me and you? We can see who ends up becoming the good guy and the bad guy by the end.

[00:45:08] Jordan Harbinger: Exactly. I don't know if I could handle the pressure.

[00:45:10] Nick Bilton: That's the thing for me that was, I mean, the most breathtaking parts of the story are that, you know, there's a point where the government's after him, he knows it. There's press conferences by senators saying, we have to catch these people. He fully understands that he could even get the electric chair for what he's doing. And he is just going on dates on OkCupid while running the website as if it's just a day in the life of a regular startup entrepreneur. That's the part — for me, I would've been popping Xanax and Ambien and God knows what else to make it through the day.

[00:45:42] Jordan Harbinger: Yeah. It's like when you hear about those mafia guys that are older and they get caught and it's like, "That was my neighbor for 10 years. What the hell?"

[00:45:52] Nick Bilton: Yeah, it's true. It's completely the case. It's how much intensity and pressure and anxiety I felt just reading the chat logs and his diary entries. In the beginning, he's definitely stressed out about these things. By the end, he has these diaries he keeps of like what he's done every day, and in one of the diary entries he like, you know, "Had to recalibrate the server, paid Inigo 500 grand or whatever, 500 bucks for his employee, hired the Hell's Angels to kill six people." Just like it's a line item on his spreadsheets. It becomes almost nothing.

[00:46:23] Jordan Harbinger: Yeah, yeah. Brings a little bit of life to the cliche, "He was such a quiet boy," right? I too would be popping Xanax, which by the way is available for purchase on the Silk Road, along with AK-47 s and explosives and everything else.

[00:46:38] Nick, thank you so much, man. It's been super enlightening.

[00:46:40] Nick Bilton: Thank you for having me.

[00:46:43] Jordan Harbinger: I've got some thoughts on this episode, but before I get into that, Ray Dalio began investing at age 12 and now has over 160 billion dollars under management at his company, Bridgewater Associates, the largest and best performing hedge fund in the world. It's no surprise that he's known as the Steve Jobs of investing. Here's a preview.

[00:47:03] I think now it's very clear that this is an event that has happened before, but not during our lifetime.

[00:47:08] Ray Dalio: Of course, it is. The last one that happened was in 1918.

[00:47:12] Jordan Harbinger: Mm-hmm.

[00:47:13] Ray Dalio: And it happened right at the end of World War I. Today, how many pandemics, wars, depressions, revolutions, and so on have we been through, and they happen over and over again for the same reasons?

[00:47:27] Three big things that are happening now that haven't happened in our lifetimes before, but happened in the 1930 to 45 period. First, a long-term debt cycle that turns to the point where central banks can no longer ease monetary policy. And so we're at the end of a long-term debt cycle in which there has to be a lot of printing of money, much like in March 1933. Two, there are wealth and opportunity gaps and values gaps, which are very large, and those are the sort of things that produce some form of revolutionary changes. Three, there's a rising power that is comparable to the existing world power that is challenging it, the United States now with China.

[00:48:25] So when we look at the world, we have three big topics that we need to talk about, and they're very big and important to understand. The capacity of humans to adapt and change and do things is enormous, but the likelihood of being able to work in an intelligent, cooperative way to do the right things would have to be considered a long shot.

[00:48:56] Jordan Harbinger: For more with Ray Dalio, including the predictable cycles that contribute to the rise and fall of great and once great nations on the world stage and where Ray sees these cycles heading now, and how we should prepare ourselves for the less comfortable cycles we're bound to experience in the future, check out episode 389 of The Jordan Harbinger Show.

[00:49:17] Love these vault episodes. This kid, man, he just crumbled and corrupted. What a wild tale. He is still in prison. Don't know what's going to happen there. I'd love to talk to him personally, although he's not being very forthcoming these days. Of course, we'll have the book linked in the show notes as we always do. Thank you so much for listening and enjoying this one.

[00:49:34] All links at jordanharbinger.com. Transcripts are in the show notes. Videos are up on YouTube. Advertisers deals, discount codes, all at jordanharbinger.com/deals. Please consider supporting those who support this. I'm at @JordanHarbinger on both Twitter and Instagram, or just connect with me right there on LinkedIn. The majority of people on LinkedIn seem less crazy. I'm going to tell you out of all the social media, LinkedIn is the least crazy so far.

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[00:50:22] This show is created in association with PodcastOne. My team is Jen Harbinger, Jase Sanderson, Robert Fogerty, Millie Ocampo, Ian Baird, Josh Ballard, and Gabriel Mizrahi. Remember, we rise by lifting others. The fee for this show is you share it with friends when you find something useful or interesting. If you know somebody who's interested in Bitcoin, the Silk Road, true crime, this kind of cybercrime stuff, definitely share this episode with them. The greatest compliment you can give us is to share the show with those you care about. In the meantime, do your best to apply what you hear on the show, so you can live what you listen, and we'll see you next time.

[00:50:57] This episode is sponsored in part by the Mea Culpa podcast. Mea Culpa is hosted by Michael Cohen, who is Donald Trump's fixer, lawyer, right hand for over a decade. He, of course, went to prison because he defied his former boss. The Mea Culpa podcast is his redemption tour of sorts. Mea Culpa with Michael Cohen delivers political news, raw and unfiltered. Plus Michael, well, let's just say he's an opinionated guy. Twice weekly, Mea Culpa features the most important people in politics, offering listeners rare insight into what's happening that they can get no place else. His guests are a who's who of politics, media, and beyond, especially on the left, as you might guess — James Carville, Joe Trippy, John Dean, Laurence Tribe. Ari Melber, Joy Reid, Kathy Griffin — oh, she's a fan favorite, isn't she? Congressman Steve Cohen, Elie Honig, Neal Katyal, Norm Eisen, Molly Jong-Fast, Sam Donaldson, Ben Stiller. That's probably a fun one. You never know who's going to show up and what they will say. And if you're on the right, you're probably going to hate this podcast. Don't shoot the messenger here. But hey, if you lean left, do yourself a favor, check out Mea Culpa wherever you get your podcasts. Find it in your favorite podcast app.