The Saga of Silk Road

The US government took a thumb in the eye with the creation of the Silk Road website. Right there on the internet you could anonymously buy drugs and various other contraband, and for a couple years no one could do a darn thing about it. See omnystudio.com/listener https://omnystudio.com/listener for privacy information.

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

• 0:00Speaker 00

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• 0:04Josh Clark?

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• 1:04Speaker 00

  Welcome to Stuff You Should Know, a production of iHeart Radio.

• 1:14Josh Clark?

  Hey, and welcome to the podcast. I'm Josh and there's Chuck and Jerry's here too. And this is Stuff You Should Know, all about the dark web and all the crazy, crazy drugs and hitmen you can buy on it.

• 1:28Speaker 02

  Sorry, I was still doing my vocal warmups.

• 1:34Josh Clark?

  I didn't know that that helps. What does that help?

• 1:37Speaker 02

  Twenty dwarves took turns doing pushups in the lawn. I'm ready.

• 1:41Josh Clark?

  Okay, good. Well, so welcome to the podcast, everybody.

• 1:46Speaker 02

  I figured it should start warming up, you know, seventeen years into this? Eighteen, how long?

• 1:51Josh Clark?

  You'd think so, yeah. Sixteen-ish, a little over sixteen. Coming up on seventeen, Chuck.

• 1:57Speaker 02

  Just wait till you hear the way my lips move in this episode.

• 2:02Speaker 02

  They're so loose.

• 2:04Josh Clark?

  So, did you loosen your lips up just specifically because the content of this episode is so thrilling?

• 2:09Speaker 02

  Uh, I thought you were gonna say something about sinking ships. Uh, no, I didn't, but this is a good one. This, uh, if everyone heard our episode on the dark web from 2020, some of this will be familiar, but this is just more in-depth about the notorious Silk Road itself.

• 2:24Josh Clark?

  Yeah, for sure. Um, yeah, and we were talking about Silk Road. For those of you history buffs, Middle Eastern history buffs, um, who were disappointed, sorry, but you should stick around because this is gonna be a pretty interesting episode.

• 2:37Speaker 02

  I didn't think about that. When are they gonna talk about cinnamon?

• 2:39Josh Clark?

  About, we did a whole episode on cinnamon, so relax there, guy.

• 2:45Speaker 02

  Yeah.

• 2:45Josh Clark?

  Um, so, you know, we're talking about what is widely considered, because I think it is, the world's first illicit marketplace on the internet. That was opened in 2011, shut down in 2013, it had a very, very brief run. It was like the Beatles of illicit drug trading websites. And, um, its legend will live on for, basically forever, because not only was it just the most audacious thing anyone had ever done on the internet as far as anyone knew up to that point, uh, it created a blueprint for a bunch of imitators to come. And also, this, the, the way, everything that law enforcement threw at this case, um,

• 3:30Josh Clark?

  and the, the court case as well, it was just so nuts that, um, it's just a heck of a story. How about that, Brownie?

• 3:39Speaker 02

  That's great. Uh, boy, there were 15 filthy jokes, I was gonna say, when you said the most outrageous thing anyone had done on the internet up until that point. I was like, I had a, a rolling Terminator-like scroll about all the early internet nasty memes that would go around.

• 3:55Josh Clark?

  You couldn't pick any of them?

• 3:57Speaker 02

  No, I just didn't want to say any of them out loud, because then kids would look them up.

• 4:01Josh Clark?

  I gotcha. Yeah, I was wondering, and we probably should have talked about this before we recorded, are we gonna like, call out any active sites or anything like that?

• 4:10Speaker 02

  Nah.

• 4:11Josh Clark?

  Okay. Because I know some. I looked them up.

• 4:17Speaker 02

  Hey, just text us to me, it's fine.

• 4:19Josh Clark?

  Okay, so let's start from the start, right? We're gonna start with a guy named Ross Ulbricht. And the reason we're introducing him early on is because he is the mastermind behind Silk Road. It was his idea, he built it originally, he ran the thing by hand, almost single-handedly for a very long time. And you just really can't talk about Silk Road without him because his personality was so wrapped up into the ethos of the site that you can't really extract one from the other, despite the fact that while he was sitting in federal court, he really wished that they would extract one from the other.

• 4:59Speaker 02

  Yeah, big thanks to Kyle, first of all, our friend and contributing writer from across the pond for his work on this. But Kyle was keen to point out just a little bit about the dark web. You know, we have a whole episode from 2020 if you want to go listen to that. But if you don't know what the dark web is, it's a part of the web where you can go and do things anonymously. And that's just a, you know, the simplest way to say it. It's much more complicated than that, obviously, if we did a whole episode. But it's where you can go if you don't want to be indexed by Google, if you don't want your traffic monitored, and if you want your anonymity insured. Doesn't necessarily mean you're some awful person doing awful things. There's a lot of people there that just believe in the freedom and anonymity that you should

• 5:44Speaker 02

  have on the internet.

• 5:46Josh Clark?

  Yeah, also, yes, for sure. Some people are just like, there's no reason for you to be invading my privacy while I'm reading The Guardian or something like that, right?

• 5:53Speaker 02

  Yeah, just to sell me stuff.

• 5:55Josh Clark?

  Exactly, that's part of it for sure, too. And then also, other people are, like, they might be whistleblowers and they have information that could very easily get them thrown in prison, but it's really important to get out to the public. There's sites like ProPublica and other journalists that have dark websites to where you can submit information and even ProPublica doesn't know who you are. And with Silk Road specifically, there were three things that came together that made Silk Road exist, and without any of them, I don't think it would have ever existed. One was who I already introduced, Ross Ulbricht.

• 6:34Josh Clark?

  The second is Tor, the Tor network, which basically when you go on to the dark web using Tor, the first thing it does is route you through three different random servers and each one encrypts your information and gives you a new IP address. So no one can figure out who you are, including the websites you visit. And then the third thing is Bitcoin. There's just no way you could have made transactions on drug deals over the internet without untraceable currency that doesn't involve like a central bank or some other third party like that.

• 7:06Speaker 02

  Yeah, for sure. And Bitcoin was huge because it was, they were good for each other. Like Ross Ulbricht sort of embraced Bitcoin in a big way, which even though it was on the dark web and even though Silk Road was, as you'll soon learn, dabbling in illegal drug trading, they used Bitcoin exclusively. So the rise of Bitcoin and the rise of, you know, things on the dark web kind of go hand in hand.

• 7:34Josh Clark?

  Yes, for sure. And this is also a time where, like the early 2010s, this was in like disruptive technology was just coming out left and right from Silicon Valley. Where it's like, well, say goodbye to newspapers, say goodbye to printed books, say goodbye to music. And I mean, it did have disruptive effects, but as we've seen, it's still kind of mellows out. It's not like the original thing just totally goes away. But this was that same time. So a lot of people have likened Ross Ulbricht to basically a darker version, if there is such a thing, of some of those Silicon Valley bros who started up a lot of those disruptive tech companies.

• 8:18Speaker 02

  Yeah. And you know what? I think we need to add a fourth on our Silk Road Mount Rushmore, because we have to mention Adrian Chen, who in 2011, when the Silk Road went live, wrote for Gawker and wrote this big expose on the Silk Road just a few months later, including like how to get there, what you can do there. And it would have been a thing anyway, but the fact that it was, it kind of exploded on Gawker made it. Bigger, quicker than it would have been, I think.

• 8:51Josh Clark?

  Right. And that also brought it to the attention of the authorities pretty quickly. Chuck Schumer.

• 8:57Speaker 02

  Yeah, Chucky.

• 8:59Josh Clark?

  He, he basically came out against it first, I think. So now the Senate was against it. He said it was a certifiable one-stop shop for illegal drugs that represents the most brazen attempt to peddle drugs online that we have ever seen.

• 9:13Speaker 02

  And they all went, yeah, exactly.

• 9:16Speaker 02

  You nailed it.

• 9:16Josh Clark?

  Yeah, right. And so because of that Tor network and because of just the anonymity of Bitcoin and the fact that people were drug dealers and drug users engaging in illicit crime over the internet, like, there was a sense like, it doesn't matter. Like, the government can't find any of these people. If they do, it's just random luck, like, say, intercepting a drug shipment in the mail. But if you're really trying to track somebody down who's a user of Silk Road, you're just not going to be able to do it. There was just a sense of security and safety that people had when they were using it, including Ross Ulbricht.

• 9:55Speaker 02

  Yeah, and they also were pretty smart early on, or I guess Ulbricht was, by making it a familiar shopping, online shopping experience. I mean, I never saw it. I think I managed to find some, like, screenshots and stuff. But it supposedly looked and operated much like any other e-retailer. You would go on there and you would have your little shopping basket and you would have your items that you could, you know, are all categorized and listed that you could sip through and you could look at customer reviews and, you know, I'm sure there were bad deals that went down, but supposedly, it was, it worked because the people selling the drugs

• 10:38Speaker 02

  believed that you should really sell the thing that you're trying to sell and you'll stay in business.

• 10:43Josh Clark?

  Right. Just like if you're a, like, you have terrible customer service and you're selling like,

• 10:51Speaker 02

  Widgets?

• 10:52Josh Clark?

  Sure. I was thinking like some sort of sewn strawberry pot holder, something in the shape of a strawberry.

• 10:58Speaker 02

  So much better than a widget.

• 11:00Josh Clark?

  But you tell all of your customers who say like it's the stitching's coming loose that they can go to hell and die.

• 11:06Speaker 02

  Yeah.

• 11:07Josh Clark?

  You're gonna get a bad rating and people are gonna stop buying from you, especially if there's other people selling sewn strawberry pot holders, right? Same thing if you're selling drugs on Silk Road. There were a ton of people selling pot and acid and ecstasy and heroin and cocaine that like you just didn't have to rely on just one dealer. So the dealers were competing with one another and to compete, they just tried to keep their user rating up as best as possible and that kept them honest. It's just nuts. Like this whole thing on, in theory, should have collapsed on day one. It just should never have worked out because it was just based on so many faulty assumptions

• 11:50Josh Clark?

  that just happened to come together and support this site until the feds shut it down.

• 11:55Speaker 02

  Yeah, they had a seller's guide where if you were gonna sell your drugs, they would say, hey, here's how to do that. Here's how you can ship drugs through the mail, you know, pretty safely, vacuum sealing and all, you know, all kinds of tips and tricks. And not that many packages supposedly were intercepted, a very small percentage of them. But you mentioned some of the things in your, I thought you were singing that Queens of the Stone Age song there for a second.

• 12:20Josh Clark?

  Which one?

• 12:21Speaker 02

  When you were, I don't know, they had that one song that was, I thought it was not so great. Cocaine and ecstasy and blah, blah, blah, blah, blah. And they were just like rattling off drugs or whatever.

• 12:31Josh Clark?

  That doesn't sound very great.

• 12:32Speaker 02

  No, it wasn't one of their best songs. I was into them for a minute.

• 12:36Josh Clark?

  I like that one hit song of theirs, it's really good.

• 12:39Speaker 02

  No One Knows, maybe?

• 12:41Josh Clark?

  Yes, that's the one. I didn't know.

• 12:44Speaker 02

  It's a good song. Yeah, so you could buy anything you want. And it wasn't just like, hey, here's some cocaine if you're interested in this upper. It was very, very specific stuff, like a very specific strain of Colombian cocaine, or a very specific strain of heroin, tar heroin that you could find. You know, if you've ever been to a legal cannabis shop in any of the states that allow that here in the US, it was sort of like that. You know, you get very detailed descriptions of stuff. And, you know, you could have a customer service representative help you find what you wanted. And it was like, if you were into that kind of thing, it was probably pretty great for you.

• 13:27Speaker 02

  And probably much safer than going to some drug dealer's house, maybe? I don't know.

• 13:31Josh Clark?

  That's a big deal. So, one of the things that was touted by supporters of Ross Ulbricht and Silk Road was that it was a site for harm reduction.

• 13:39Speaker 02

  Yeah.

• 13:40Josh Clark?

  That it was so vastly safer than buying drugs on the street, often from some rando you don't even know, or at a club, or something like that.

• 13:47Speaker 02

  Oh, yeah. That's dangerous.

• 13:49Josh Clark?

  That it was actually providing a service that actually made the world safer. It didn't fly very well, as we'll see, but that was a big talking point for them.

• 14:00Speaker 02

  Yeah, and I don't want anyone to misinterpret that I'm saying that like, hey, you should just be able to buy drugs in the mail and it's totally safe and you should trust that. But they seemed to be setting up a situation where they were trying to ensure that. There was a lot of trust between buyers, sellers, everybody. Like, a situation like this doesn't happen if there's not trust between all the participating parties.

• 14:24Josh Clark?

  Precisely. Yeah, for sure. Yeah, it's just crazy to me that it ever worked.

• 14:31Speaker 02

  Should we take a break?

• 14:32Josh Clark?

  Yeah, let's take a break and we'll come back and talk about some of the nuts and bolts of the whole thing.

• 14:37Speaker 02

  All right, we'll be right back.

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• 17:49Speaker 02

  So you've mentioned this guy, Ross Ulbricht, the founder and creator. We need to talk a little bit about this dude. He went by the alias Dread Pirate Roberts. Even though later in his defense, there would be, it would be brought up that there were like many Dread Pirate Roberts over the years and that he, he sold it at one point and wasn't even involved anymore. It's, if you follow the court case, it gets really, really in the weeds.

• 18:15Josh Clark?

  Yeah, his quote in court was, "Do you not know the Dread Pirate Roberts reference?"

• 18:20Speaker 02

  Right, yeah. They were like, "Why would you name yourself that?"

• 18:23Josh Clark?

  Right.

• 18:24Speaker 02

  And he said, "Have you never seen The Princess Bride?"

• 18:27Josh Clark?

  Yes. And for the people who haven't seen The Princess Bride, number one, go see The Princess Bride. And number two, Dread Pirate Roberts was the name of a, well, a pirate who was essentially like a character that different people over the years and generations inhabited. So say Dread Pirate Roberts was 200 years old because he was made of, of successive pirates who wore that mask and used that name.

• 18:50Speaker 02

  Yeah, for sure. So Ulbricht had a very, very smart guy, is a very smart guy. He had a Bachelor of Science in Physics, got his Master's in Material Science and Engineering. And was in Austin, Texas in 2009 when he tried a few different initial companies. Basically, he had a video game company tried. He found the most success with a secondhand book retailer called Good Wagon Books, where he kind of learned how to do web development and inventory management and e-retailing. Kind of a starter kit for what he would need to start Silk Road. But it still wasn't making the kind of dough he wanted to make. I think they were pulling in maybe low six figures in a year.

• 19:35Josh Clark?

  Yeah, yeah. And he had like five employees sorting like 50,000 books.

• 19:41Speaker 02

  Not bad.

• 19:41Josh Clark?

  And they were selling them on Amazon like you do, like you can buy used books on Amazon. That's just what they did. But his heart wasn't in it. And after the shelves that he had built in this warehouse to hold the books all collapsed, he was like, I'm not going to pick those up. I'm just going to set this warehouse on fire and walk away.

• 20:00Speaker 02

  That's really funny. That sounds like something I would do.

• 20:02Josh Clark?

  I would do the same thing.

• 20:04Speaker 02

  I wouldn't set it on fire and walk away, but I'd just walk away.

• 20:07Josh Clark?

  So he, one of the other reasons he was keen to walk away is he'd been already thinking about Silk Road for close to a year by now.

• 20:15Speaker 02

  Yeah.

• 20:16Josh Clark?

  And one of the things that really kind of spurred his interest in creating something like an online illicit drug sale website is that he became interested in libertarian theory, specifically libertarian economic theory, which is basically that if you don't have economic freedom in particular, you're going to be a slave to the grind. They've got you, essentially. And that you can either get rich and remove yourself from that game or that rat race, or you can try to change the rules of the game and make it much more fair and equitable and get rid of coercion and all that stuff. And it's all based on the libertarian philosophy of self-ownership, which essentially explains itself.

• 21:01Speaker 02

  Yeah, he, I don't know. Explain it.

• 21:05Josh Clark?

  Oh, well, you own yourself. So any kind of laws or prohibitions of anything that say you do to yourself, say, taking drugs, is just completely outrageous and immoral and is illegitimate.

• 21:20Speaker 02

  Okay.

• 21:21Josh Clark?

  So drug laws specifically are illegitimate and terrible to libertarians because you're taking the drugs for yourself and that's your choice, right? It's a personal choice. So that really kind of explains a lot why he was like an illicit drug website. It was a thumb in the eye to the drug laws that he and other libertarians feel were illegitimate.

• 21:47Speaker 02

  All right. I'm glad I asked.

• 21:50Josh Clark?

  Yeah, I'm glad you asked too, because I really wanted to get that off my chest.

• 21:53Speaker 02

  So Silk Road grew. He started, it was not just a one-person operation. It was too big for that. So he needed some employees. These people all went by these kind of fun little nicknames, including Variety Jones and Enigo, also from Princess Bride.

• 22:13Josh Clark?

  Yeah.

• 22:13Speaker 02

  Didn't notice that. Libertas Smed. And then another one, Chronic Pain, one word. The first C is capitalized. And that person's name was Curtis Green, and he was the first person that would be arrested in the Silk Road operation. And so you'll just sort of put a pin in that guy.

• 22:32Josh Clark?

  Yes, for sure. So he gets the website launched in 2011, around the beginning of 2011. And to get things kicked off, he started growing psilocybin mushrooms so that there was something somebody was selling on Silk Road. And pretty soon, other people were like, wait, you're really doing this? Like, this is for real? I want to make money selling drugs online. It just kind of took off from there. Again, without cryptocurrency, there just wouldn't have been a Silk Road. And this is actually pointed to by some people as like an early proving ground that showed like, yep, Bitcoin works. It does exactly what it says it can do.

• 23:16Josh Clark?

  And it could completely revolutionize the global economy. This was the first chance for it to really kind of show its stuff. And it really did because it worked. And one of the other reasons it worked too is because Ross Ulbricht was honest. He hand, I guess, hand transacted every transaction between seller and buyer on the site for a while. And at that point, he would hold the money in escrow. And then when the whole thing was, when the deal was done and everybody was satisfied, he would release the money to the seller. At any point in that string, he could have been like, thanks for the money, chumps. Thanks for the money, chumps. Thanks for the money, chumps.

• 23:59Josh Clark?

  And just taken off with the Bitcoin and he didn't. And the reputation that that helped give that site was another reason it started to grow and flourish.

• 24:08Speaker 02

  Yeah, for sure. So as the site is, you know, kind of going along and it's making all kinds of money and getting more and more popular, or as popular as something is on the dark web. He started getting a little more political under his moniker. DPR Dread Pirate Roberts started making these big statements about just sort of his philosophies about politics. He would say things like, stop funding the state with your tax dollars and direct your productive energies into the black market. So it started sort of bordering on manifesto kind of stuff. I think they would have shut it down anyway, just because they were dealing in illegal drugs. But the US government definitely hates it when they don't like the word manifesto.

• 24:54Speaker 02

  So I think, I think all this other political stuff definitely drew even more attention and ire, maybe than it would have?

• 25:01Josh Clark?

  Mm hmm. Yeah, no, I think so. Like I said, it was a thumb in the eye. And I think it kind of felt like that to the government and the powers that be, right?

• 25:09Speaker 02

  Yeah, he thought, he kind of thought, and he kind of was, leading a revolution in a lot of ways, because as we'll see later on, a lot of more sites like this were born in its wake.

• 25:20Josh Clark?

  Right. So it's interesting to see, too, the evolution of him going from a libertarian idealist to what the feds eventually described as like the kingpin of a global drug cartel.

• 25:36Speaker 02

  Yeah.

• 25:37Josh Clark?

  Really overblown, as we'll see.

• 25:39Speaker 02

  Yeah.

• 25:40Josh Clark?

  But in the beginning, he, even as a libertarian, said, don't, there's limits here. Like, this is not just a free for all. You can't have child pornography. You can't try to sell weapons of mass destruction. You can't offer hitman services, sell stolen credit cards or personal information. Like, you just can't do that. And if you scam anybody, we're going to boot you off the site and we're going to hunt you down and sic dogs on you or something like that. He said, "Basic rules are to treat others as you would wish to be treated, and don't do anything to hurt or scam someone else." So that was like the whole idea. And then the fact that his moniker was Dread Pirate Roberts, and everybody loves, like, there's no one who's seen The Princess Bride and doesn't love it. Prove me wrong, I will prove you wrong.

• 26:24Josh Clark?

  So all of that kind of combined, almost a cult of personality grew up around Dread Pirate Roberts and attracted more and more people to Silk Road. And like, I think, I get the impression like you were, like, you felt cool to be a user of Silk Road.

• 26:40Speaker 02

  Yeah. Like, he created a kinder, gentler drug trade in a lot of ways.

• 26:46Josh Clark?

  Yeah.

• 26:46Speaker 02

  Um, if you're wondering like, yeah, but this guy could get shut down in a lot of ways that don't have anything to do with the government, uh, like a denial of service attack or something like that.

• 26:56Josh Clark?

  Mm-hmm.

• 26:56Speaker 02

  Uh, supposedly, uh, he was paying a lot of money, um, for protection for this kind of thing, uh, maybe up to $50,000 a week. Uh, Wired did a really great, and I remember reading this back then, I didn't go back into it, but, um, a big two-part report on this and, uh, they, they had it up to 50 grand per week in, in protection, but considering they ended up making about a billion dollars over, what, two years or so, uh, that's, you know, uh, pennies in the fountain.

• 27:24Josh Clark?

  Yeah, for sure, um, but protection is in quotes, like, that was from the very hackers who are like, we're gonna shut your site down if you don't give us 50 grand a week.

• 27:32Speaker 02

  It's like any other mob protection.

• 27:33Josh Clark?

  Exactly.

• 27:33Speaker 02

  We're not gonna wreck your store.

• 27:34Josh Clark?

  It's a racket, for sure.

• 27:35Speaker 02

  Yeah.

• 27:35Josh Clark?

  So, yeah, he would get blackmailed all the time, people were trying to shut down the site, like, it was a, uh, they're like, criminals were attracted to Silk Road and there's plenty of criminals who, um, they're like speculators, so blackmailers are, you know, they're not actually doing anything productive, they're just making money off somebody else's, um, work, right?

• 27:54Speaker 02

  Yeah.

• 27:55Josh Clark?

  Um, so, yeah, it kind of attracted that stuff, so, in addition to dealing with all of that, he was dealing with customer service, he was trying to keep the site running, something to know about Ross Ulbricht, too, he was a self-taught coder, so he was teaching himself how to keep this massive website going as he went along, and, um, keeping himself totally anonymous to everybody, including all of the people who he worked with who were, uh, de facto employees, basically.

• 28:22Speaker 02

  Yeah.

• 28:22Josh Clark?

  So it was a lot of stress after a little while.

• 28:24Speaker 02

  Totally, and besides the drugs, he also had a, a team of, uh, crocheters making those strawberry oven mitts.

• 28:31Josh Clark?

  [laughing]

• 28:33Speaker 02

  Lots to keep up with.

• 28:34Josh Clark?

  For sure.

• 28:35Speaker 02

  So, um...

• 28:38Speaker 02

  How did it all go bad? Well, it's because, again, the government was very, very keen on getting this thing shut down as fast as they could. But, like you mentioned earlier, the very way this thing was built made it really, really hard, almost said impossible, but clearly not, but really, really hard to find out any real information about who these people were, where they were, where their computers were. So the FBI got involved initially in trying to take down Tor. It was called Operation Onion Peeler, and I'm pretty sure we talked about that in the dark web app.

• 29:19Speaker 02

  But they, in 2013, there was an agent named Chris Tarbell that identified a secret server at a data center, a Tor data center in Iceland, and this is really what got the ball rolling.

• 29:32Josh Clark?

  Yeah, so this is the official line of the FBI, the way that they finally discovered the actual IP address of Silk Road, was that Tarbell was sitting there analyzing the traffic going to and from the site while he was like sending in bad information at it, like bad passwords and stuff like that, and then tracking what IP addresses came back. And then he copied the IP addresses and he put them into a browser URL and do that over and over again. And eventually he struck gold and stumbled onto the real IP address of Silk Road, which was then traceable to that server data center in Iceland.

• 30:15Josh Clark?

  And from there, they then had a copy of the Silk Road website, including all administration access and privileges, and they started to set up their case from that point on.

• 30:25Speaker 02

  That's right. That was the FBI's line. If that seems a little hard to believe, that they would just sort of get lucky, you're not the only person who thinks that. None other than, oh geez, was he Bill or Ted?

• 30:39Josh Clark?

  Bill.

• 30:40Speaker 02

  Bill. Alex Winter from Bill and Ted's Excellent Adventure and Focused Journey.

• 30:43Josh Clark?

  And don't forget, he was a vampire in Lost Boys, too.

• 30:46Speaker 02

  Yeah, good point. He made a film called Deep Web that, geez, was that out this year?

• 30:53Josh Clark?

  I think so, or last year, very recent.

• 30:56Speaker 02

  Yeah, pretty recent film, I think 24, where he, you know, he doesn't, he didn't like create this contention, but he basically brought to light like, hey, a lot of people say that, no, no, no, that's not how you found out. What you did was trampled on Olbrich's Fourth Amendment rights. And that you hacked Silk Road, you didn't have a warrant to do so, and you had some sort of, you know, mass scanning going on, on the internet for passwords, and you lied about all this.

• 31:24Josh Clark?

  Yeah, the, the idea is that the NSA was involved, helping in this investigation, using their crazy, terrible powers to basically find passwords to that site. And they used it to hack in, and the, they're, well, you're like, okay, whatever, they're trying to take down the site. It's the FBI. Well, the, the gist of that is, is that they did that first, then got the evidence that they then went and got a search warrant for. And then everything started to get legitimate from that point on. So that's the, the contention about his Fourth Amendment rights to, against search, illegal search and seizure were violated.

• 32:00Speaker 02

  Yeah, and if, if it's all just sounds like weird and screwy because it's online, it would be no different than if they like broke into someone's house, took some evidence, and then said, now that we have the evidence, we're going to get a search warrant to go legally back into that house.

• 32:15Josh Clark?

  Right.

• 32:16Speaker 02

  Yeah.

• 32:17Josh Clark?

  And you mentioned Tarbell, he was an FBI agent. He and the FBI were just one of multiple agencies from Department of Homeland Security to the DEA, to the IRS.

• 32:29Speaker 02

  Oh, yeah.

• 32:29Josh Clark?

  All working, like each one had a task force, trying to take down this website, competing with one another in a lot of cases to take down this website and catch this big fish that Chuck Schumer didn't like. And like finally Tarbell was the one who gets the credit, not just for finding the actual IP address and then the server for Silk Road and all of the evidence that that yielded, but he was there on the day and helped orchestrate. This guy was a cybercrime FBI agent. So again, this is the official line. And it's very thrilling in the Wired article, how they describe it. But he helped orchestrate or oversaw the actual arrest of Ross Olbrich,

• 33:12Josh Clark?

  which in and of itself was just fantastically amazing.

• 33:16Speaker 02

  Yeah, for sure. All right, so the FBI gets that copy of the server contents from Iceland. They look at all the traffic and they found traffic to the administrator's login and then narrowed that down to the most recent traffic was in San Francisco at a place called Cafe Luna on Sacramento Street. They did some more investigation through the IRS, chipping in this time. Like you said, so many agencies involved. And they matched the San Francisco lead. So they were like, this is all lining up, you guys. There was an IRS agent named Gary Alford who saw posts about Silk Road on forums in,

• 33:58Speaker 02

  I think, a couple of years, 2011 and 2013, from a username Altoid. And the email in the post history said Ross [email protected]. They found out that he lived near that cafe and all roads, all of a sudden, were pointing to Ross Ulbricht.

• 34:15Josh Clark?

  And then supposedly, the really damning piece of evidence was that that user, Altoid, quickly changed their username to Frosty. And Frosty was the main user account that ran Silk Road.

• 34:27Speaker 02

  Yeah.

• 34:28Josh Clark?

  That was the name of the main central user account, right? So like, all of these things just falling into place, it was just almost too good to believe.

• 34:39Speaker 02

  Yeah. And then it went down like a movie. And you know what? Maybe that's a great time for a little cliffhanger, huh?

• 34:46Josh Clark?

  Oh, boy.

• 34:47Speaker 02

  All right. We're gonna see what movie we're talking about right after this.

• 35:03Josh Clark?

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• 35:12Speaker 02

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• 35:25Josh Clark?

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• 35:41Speaker 02

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• 36:05Speaker 02

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• 36:19Josh Clark?

  Well, with Base44, describe that in your own words. You don't need to know coding or programming. Then you just keep editing and refining it until it works exactly the way you want. Your build comes headache-free with built-in login, data storage, backend, and hosting. So what's the app you wish existed?

• 36:37Speaker 02

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• 36:48Josh Clark?

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• 37:05Speaker 02

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• 37:20Josh Clark?

  Yeah, plus, everything at Quince is priced 50% to 80% less than similar brands. They work directly with ethical factories and cut out the middlemen so you can give luxury quality pieces without the luxury price tag.

• 37:33Speaker 02

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• 38:08Josh Clark?

  Chuck, I'm going to guess the movie is Old Yeller.

• 38:14Josh Clark?

  Is it? Am I right?

• 38:16Speaker 02

  You nailed it.

• 38:16Josh Clark?

  Okay. Poor Old Yeller. I hate how this goes.

• 38:20Speaker 02

  I was going to spoil Old Yeller, but I decided not to.

• 38:24Speaker 02

  Watch it. That dog may live. You never know.

• 38:26Josh Clark?

  Good for you for not spoiling a 60 year old film.

• 38:30Speaker 02

  Yeah, and a book, I think, too, right?

• 38:32Josh Clark?

  Yes. Although there was a sequel, it wasn't very well received.

• 38:36Speaker 02

  Old Yeller 2?

• 38:39Speaker 02

  Really?

• 38:39Josh Clark?

  It turns out the little kid missed. The first time. He didn't in the second film, though.

• 38:45Speaker 02

  And now Old Yeller's back for revenge?

• 38:50Speaker 02

  Write that down. That's a good one.

• 38:51Josh Clark?

  Okay. So, okay, what movie are we talking about then? How about what type of movie are we talking about?

• 38:57Speaker 02

  Well, we're talking about a probably some sort of a courtroom thriller because what happened was they went to a library and literally, and this is what the prosecution said, literally caught him with his fingers at the keyboard, running Silk Road. They were in the library. They had a, an agent, you know, chatting with him and obviously surreptitiously undercover. And while this was happening, they drew his attention away by starting a little like quarrel among some other people, also, you know, FBI actors or whatever. And there was a woman, another FBI agent, sitting across from Olbret at the time when this happened and Olbret turns around and is like, what's going on over there? She grabs that laptop and.

• 39:42Speaker 02

  Because he could probably in a single swipe of a keystroke or something, like encrypt everything on his laptop if he saw somebody coming at him. So they knew that could happen. They diverted his attention just long enough for this agent to grab his computer and that was it.

• 39:58Josh Clark?

  And boy, oh, boy, did they find some just damning evidence. It turns out Ross Ulbricht kept a diary of his like ideas and growth and like administration and all the problems he had to deal with for Silk Road. Dear diary. Exactly. Chronic pain really hurt my feelings today.

• 40:25Josh Clark?

  Those were found on his laptop. Logs of chat logs that he had between him and other administrators about running the site. He was logged in as the main user Frosty, the person who was actually running the show when they stole or grabbed his laptop, no stole it. He had spreadsheets like tracking Silk Road. I mean, like just if a prosecutor could be like, I want this, this, this, and this for evidence. It couldn't get any better than what they found on Ross Ulbricht's laptop.

• 41:00Speaker 02

  Yeah, so they also traced about $80 million in profit to him. This is a dumb question that I'm just now thinking of, but what did he just take a cut from every transaction? Was it that simple?

• 41:13Josh Clark?

  Yes.

• 41:13Speaker 02

  Okay. That's what I figured. I just didn't know for sure.

• 41:16Josh Clark?

  And I think it was a reasonable cut. I don't think it was some massive take or anything like that. And he would only, he would just transfer it like once a week, like his accumulated cuts from that week. He was very honest in that sense.

• 41:32Speaker 02

  So he would get his, his small percentage, a bottle of Delaudet and a strawberry oven mitt? For every transaction?

• 41:40Josh Clark?

  Every Saturday night.

• 41:43Speaker 02

  So we mentioned earlier that as part of his defense, they were like, you know what? He may have started Silk Road, but he sold it. And there were many Dread Pirate Roberts and one of the other ones framed him. All of this stuff was just a small part of his defense. It was not an easy sell. It did not work. He was convicted for creating and operating Silk Road and got five sentences. Got a 20 year sentence, a 15 year sentence, a five year sentence, two life sentences with no chance of parole. And the judge said, it was your opus. You wanted it to be your legacy and it is.

• 42:22Josh Clark?

  Yeah, the judge mentioned harming the fabric of, it was very destructive to the fabric of society. And when your judge is pulling out fabric of society in your sentencing.

• 42:33Speaker 02

  Yeah, you're screwed.

• 42:34Josh Clark?

  You're in big trouble. And so he was effectively handed a death sentence. Like you don't outlive a sentence like that. And it was just totally out of proportion to the charges he was facing. Like conspiracy to commit like drug trafficking and fraud and just, I mean, it was some hardcore offenses, but nonviolent offenses. And he was given the kind of sentence that you would give like a multiple killer or a mass killer or something like that. Right? And the reason why is because he was, there was evidence found of five to six murder for

• 43:13Josh Clark?

  hire schemes that he had ordered or agreed to as Dread Pirate Roberts to kill like a blackmailer, a witness, some other people. And even though he was never charged in federal court for this, even though they couldn't prove any of those cases and the prosecutors in this case even said to the jury, like, we're not saying, like, this is not part of his, his, um, his charges. We're not prosecuting him for that. But seriously, let me, let us just tell you about that. And so they're like, they, they, he was tainted by the media. He had a bad reputation from that point on, because that's totally different from setting

• 43:57Josh Clark?

  up a libertarian illicit drug marketplace.

• 44:01Josh Clark?

  Now you're ordering hits on people to keep your drug enterprise going? That is a whole different kettle of fish in the public's mind. So his reputation was smeared from the outset. The jury was tainted with this information. And the idea, oh, and the judge referenced it in explaining why the sentence was so harsh. And so all of that is generally considered illegal, like illegitimate. And he tried to appeal all the way to the Supreme Court. They wouldn't hear it and that was that. So his last chance is some president coming along at some point and saying like, you know what? You're not so bad. Presto, changeo, you're no longer a felon.

• 44:39Speaker 02

  Yeah, he was actually, would likely have been indicted for a murder conspiracy in Maryland. It was dropped because he got convicted, you know, for whatever, life and beyond. It was dropped because he was convicted on the other charges for a gazillion years or whatever, with no chance of parole. But it was a pretty interesting situation with what ended up being a corrupt DEA agent and a secret service agent and a sting operation, basically, right?

• 45:11Josh Clark?

  Yeah, one of the guys who was really pursuing him from the outset was a guy named Carl Force, a DEA agent.

• 45:18Speaker 02

  What a name.

• 45:19Josh Clark?

  Yeah. He posed as a gangster named Nob, who basically became a confidant of Dread Pirate Roberts. And it went so far out of undercover that he became a criminal himself. He posed as another user to sell tips and stuff about the investigation against Silk Road to Dread Pirate Roberts for like a hundred grand. He stole 350 grand in Bitcoin, which was one of the reasons why Dread Pirate Roberts ordered a hit on one of the people, because he thought that other person had stolen it. This guy was dirty as the day is long. And they say in part because a lot of the charges, including that extra murder for hire

• 46:02Josh Clark?

  that was in Maryland, was arranged by this crooked DEA agent. They're like, we're not, we're not even going to try this one.

• 46:09Speaker 02

  Yeah. Yeah, I guess there's no point at that point, especially because it's not like it was carried out. If there was like a, you know, if it had been carried out and there was a murder victim or something like that, they probably would have. But, um,

• 46:21Josh Clark?

  Right.

• 46:21Speaker 02

  Yeah, there were never any, just to be clear, you know, no murder for hires ever took place, but it was just the hint that that was going on really influenced the judge and the sentencing and everything. Um, he was, uh, I believe in Alex Winter's documentary, he points out that a lot of the people that were also brought to trial for this got very, including some of the drug sellers, uh, people that, that ran Silk Road 2.0 after this.

• 46:47Josh Clark?

  Yeah.

• 46:47Speaker 02

  They got sentences of like six years on average. And so there's been a lot of calls for, for clemency that it was, you know, it was too stiff of a sentence.

• 46:55Josh Clark?

  Yeah. And they were clearly, I think the judge also referenced like, this is a huge, like, everybody's watching this case, everybody's following this, you know? Um, and I want to send a message to anybody who would follow in your footsteps that we're going to basically give you a death sentence if you, if you try it. They just didn't follow through on that, which makes his sentence all the more unfair.

• 47:16Speaker 02

  Yeah.

• 47:17Josh Clark?

  Like, had they handed down sentences similar to his for people, you know, sets, like, setting up illicit drug marketplaces? There's some sort of like legitimacy to it just because of the precedent and then the custom that developed.

• 47:32Speaker 02

  Yeah.

• 47:32Josh Clark?

  Just doing that to one person and then not following up, you, that's just, that's just wholly unfair. And again, possibly a violation of his Sixth Amendment rights to a fair trial.

• 47:44Speaker 02

  Yeah. Uh, I mean, the idea may have been to send a message like, hey, this will never be tolerated. Uh, this is the first example of this and we're going to throw, you know, 10 books at them. Uh, but it, you know, it didn't stop anything. Uh, like I just mentioned, there was a Silk Road 2.0.

• 48:00Speaker 02

  That was closed in 2014, along with 26 other sites, uh, doing similar things. So Silk Road definitely opened that whole door and it's, it's, I don't know if they can shut them down as fast as they can be born at this point, probably.

• 48:16Josh Clark?

  It seems like the kind of thing like, um, mushrooms just cropping up. Like you pluck one and two more go in its place, essentially. Like, there's just nothing. I mean, it's not just American kids doing this. They're like, the Russians are like, I'm sure the North Koreans are doing it. Like, everybody's doing it. Like, you just can't, it's impossible to stop now. So much so that almost makes you wonder if somebody else would have come up with this concept had Olbrich not first, you know?

• 48:42Speaker 02

  Yeah, yeah, I'm unsure someone would have come along.

• 48:45Josh Clark?

  Um, there's a freeross.org website, which his supporters created, uh, that's still around. Um, and if you're asking like, wait a minute, how can everybody support him if he's ordered like five or six murders for hire? Their position is that like, that was the other Dread Pirate Roberts who set him up, whoever that was.

• 49:03Speaker 02

  Right.

• 49:03Josh Clark?

  That Ross Olbrich did not order those hits, that he's a good guy, humane guy, would never do something like that. Um, but he's still in prison. I saw a tweet from him, I don't remember when, but he was saying, uh, the thing he misses the most is not being able to see the night sky anymore, which is somehow like the saddest thing you could say as a prisoner. But yeah, there, there's a lot of people out there who are like, that kid is never getting out. He just puts such a thumb in the eye of the US government and law enforcement that I don't know, I don't know if he'll ever get clemency.

• 49:36Speaker 02

  Yeah, the night sky thing is definitely better than saying Olive Garden.

• 49:42Speaker 02

  Get more sympathy.

• 49:42Josh Clark?

  I don't know, man. Never ending breadsticks?

• 49:46Speaker 02

  That's true. I think that, uh, oh, nevermind.

• 49:49Josh Clark?

  Okay. Let's go get some breadsticks after this, okay?

• 49:53Speaker 02

  Oh, that'd be great. Oh, boy, remember that time we went to Red Lobster?

• 49:56Josh Clark?

  Yeah, in Silver Spring?

• 49:58Speaker 02

  Yeah, and I had never really eaten there much, and that was one of your like special things as a kid, right? Eating those, uh, cheddar biscuits or whatever?

• 50:05Josh Clark?

  Yeah, kid.

• 50:08Speaker 02

  An adult.

• 50:10Josh Clark?

  I love those things. Yes, I introduce you to them is what you're saying, right?

• 50:13Speaker 02

  I think so. Like, I may have had one when I was a kid, but we just didn't go out to eat a whole lot, and Red Lobster was like, far fancier than we could even afford on special occasions. So, uh, yeah.

• 50:23Josh Clark?

  You always make me feel so bad about my upbringing, which was not wealthy or well-to-do in any way, shape, or form.

• 50:28Speaker 02

  You were silver spoons. Are you kidding me?

• 50:31Josh Clark?

  Not silver spoons, Red Lobster.

• 50:34Speaker 02

  Yeah, no, that's fine. Red Lobster was a very, or I imagine is a very doable fancy dinner. Uh, we just didn't go out to eat much. Don't feel bad.

• 50:42Josh Clark?

  Yeah, I think the fancy part also is really largely marketing, Chuck. I think when you see the actual product in front of you, it's not, not super fancy. Yeah. Although, did you hear? I think they filed bankruptcy because of endless shrimp.

• 50:57Speaker 02

  Yeah, it was a disaster.

• 51:00Josh Clark?

  Can you imagine? That's like, that's like an Onion headline.

• 51:03Speaker 02

  Yeah, I've read quite a bit about that for some reason, because it was just so interesting to me. And sad, you know? It's an American icon. Who knew?

• 51:12Josh Clark?

  Well, since we talked about Red Lobster, of course, that triggered listener mail, everybody.

• 51:20Speaker 02

  Uh, I'm gonna call this the Stuff You Should Know bump. Uh, hey, guys, longtime listener, first time caller, love the show. Uh, I'm curious if you've ever tracked the Stuff You Should Know bump. Does it even exist? I know that every time you mention a documentary with more info or something like that, my wife and I end up coming through our streaming services to find it and learn more. Uh, most recently, we watched Tread after the Killdozer episode. Now I'm teeing up American anarchist after Swatches. Uh, he said, oh, wait, I may have mixed that up with the anarchist cookbook episode. Anyway, and by the way, everyone, we forgot to mention the Swatch Guards. I feel so bad about that. We heard from a lot of people on that.

• 51:58Josh Clark?

  Oh, yeah, I forgot all about that.

• 52:00Speaker 02

  I totally forgot about Swatch Guards.

• 52:02Josh Clark?

  Yeah.

• 52:03Speaker 02

  Anyway, Swatch Guards are little rubber things that went over the, the glass, not the bezel. I was wrong about that. The bezel is the, the ring that holds the, the glass, so.

• 52:12Josh Clark?

  Man, I understood it before, but not now.

• 52:16Speaker 02

  You know, you look at a watch face and I said, I think I said the glass was a bezel. I just misspoke. The bezel is the ring that holds that glass in place.

• 52:23Josh Clark?

  Okay, I think I got it that second time around.

• 52:25Speaker 02

  Yeah. All right, back to the email. Anyway, guys, it made me think that if other viewers like me, if there were other viewers like me, there could be a noticeable bump in views or listens every time a documentary or song or something gets mentioned. Creating your own version of the Colbert bump. We need statistics. We're getting meta and do a SYSK episode about the STSK bump. I think you just goofed up on that last part. That's Andy from Baltimore. Andy, we don't have data on this, but we definitely had people send in, I can't remember what song it was that you referenced, but it ended up like ranking in Spotify or something and we like to think that was because of us.

• 53:07Josh Clark?

  Well, we know it was because remember we conducted an experiment and talked about Barry Manilow, I think even now in Black Sabbath's War Pigs and they showed up in the top 10 of Spotify searches.

• 53:19Speaker 02

  That's right. So, hey, I guess we should plug Silver Spoons then, the Josh Clark life story and we'll see if that gets a bump on wherever that's streaming.

• 53:27Josh Clark?

  Speaking of bumps and plugs, there is one other podcast I'd like to plug. Chuck, you know our friend and colleague Daniel White son from Daniel and Jorge Explain the Universe podcast?

• 53:38Speaker 02

  Oh, yeah.

• 53:39Josh Clark?

  So their podcast just came to an end, but ever the productive person, Daniel, came up with another one that just launched called Daniel and Kelly's Extraordinary Universe. He said, new podcast, same universe. So if you're into all the stuff that is very interesting, like space and time and aliens and black holes and philosophy and just the whole coolness of the universe we live in, then go check out Daniel and Kelly's Extraordinary Universe podcast for a recommendation.

• 54:09Speaker 02

  Sounds great. Good people.

• 54:11Josh Clark?

  Well, if you want to be like, who was that that sent us the STSK?

• 54:15Speaker 02

  Andy from Baltimore.

• 54:17Josh Clark?

  All right. If you want to be like Andy from Baltimore and get in touch with us, then we would love to hear from you. You can wrap it up, spank it on the bottom and send it off to [email protected].

• 54:31Speaker 00

  Stuff You Should Know is a production of iHeartRadio. For more podcasts, iHeartRadio, visit the iHeartRadio app, Apple Podcasts, or wherever you listen to your favorite shows.

• 54:47Josh Clark?

  Buy smart, drive for less and trade for more. That's Toyota affordability. And it starts with a great deal on an off-road-ready Tacoma or half-ton Tundra, two of Toyota's longest-lasting trucks, combining power for work, tech for adventures, and style in between. And they're built on a reputation for quality and reliability, which is why Toyota trucks are known for holding their value, which could mean big savings when it's time for your next Toyota. So get a great deal today and a great value tomorrow. Shop toyota.com for more. Toyota, let's go places.

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