Taylor Lorenz’s Power User - A Crypto Convict's Spectacular Comeback Tour: How Ross Ulbricht Became A Powerful MAGA Influencer

Episode Date: October 8, 2025

SUPPORT ME ON PATREON!!Buy a subscription to my Tech and Online Culture newsletter, User Magazine to support my work!!!! 🙏 Nearly a decade ago, Ross Ulbricht, the founder of the Silk Road dark web marketplace was sentenced to a double life sentence in prison. Now, he's out and has become a powerful influencer and political figure in the MAGA movement.Ryan Mac at the New York Times has been covering Ulbricht for over a decade. He joined me to dive deep into Ulbrict's' past, how the Silk Road transformed the web, and how this crazy alliance between bitcoin billionaires, libertarians, and MAGA die-hards has skyrocketed Ulbricht to fame and set him up for a major role in politics.  If you like this video, please support me on Patreon!! READ RYAN'S FANTASTIC NYT STORY: https://www.nytimes.com/2025/09/07/technology/ross-ulbricht-silk-road-comeback.htmlFollow me:https://www.instagram.com/taylorlorenz https://www.instagram.com/taylorlorenz3.0 https://www.tiktok.com/@taylorlorenz

His friend bought it, gave it to him at this high school dance in Australia, and the kid thought he could fly and jumped off a balcony and landed kind of an iron fence and impaled himself, essentially, and died. Nearly a decade ago, Ross Ulbricht, the founder of the Silk Road Dark Web Marketplace, was sentenced to a double life sentence in prison. Once known as the outlaw mastermind behind one of the web's earliest illicit marketplaces, Ross amassed millions of dollars in cryptocurrency

before most people had ever even heard of the Bitcoin. Now he's out of prison and has transformed himself into a powerful influencer and burgeoning political figure in the MAGA movement. Ryan Mack at the New York Times has been covering Ross for over a decade from when his Silk Road saga was just beginning. Today, we're going to dive deep into Ross's life, talk about how the Silk Road transformed the web, and how this crazy alliance between Bitcoin billionaires, libertarians, and MAGA diehards has skyrocketed Ross Ulbric to fame and set him up for a major role in U.S. politics. Hi, Ryan. Welcome to my podcast.

What's up? How's it going? Okay. So I want to dig into the Silk Road. Ross Ulbricht, you wrote this amazing story, kind of detailing his like comeback. A lot of people, I think, aren't familiar what he's been up to recently, but I want to start from the beginning. Can you talk about the Silk Road and what it was for people who don't remember? Like, where did this website come from and what did it do? Yeah, it's crazy because it's, it's been so long. I mean, I started reporting on this story when Ulbrook was arrested in 2013, you know, as a kind of a cub reporter starting my career.

And to think of back and look back on it is like kind of crazy. But the Silk Road for those who weren't around at that time or don't remember it was a dark web marketplace to buy drugs. You could do a lot of other things on it too, buy other things. But mainly it was drugs. So anything from heroin to methamphetamine to pot to, you name it, you could probably find it on that website. And you use Tor to access the dark web. Tor is an anonymizing online software that kind of routes your internet traffic

through different places so you can't be tracked. And you use it to access the Silk Road on the dark web. And from there, you kind of just could, you know, browse anything like it was the Amazon of drugs, basically. The Silk Road is the first time I remember, and I was also just getting started in journalism, but hearing about, like, the dark web. And I feel like people, especially as tech reporters,

would always kind of like, you know, normally, people would, like, ask you about it. I never even knew how to access it. Like, what was being sold? I knew people that got like fake IDs off there and obviously like the drug stuff, but like what was actually going on on that website? Like was it all just like complete illegal debauchery or was there like some reason for it to exist other than that?

When we say the dark web, first of all, it means an unindexed part of the, you know, internet. You know, a lot of the stuff we see on Google is stuff that's indexable, it's findable, it's searchable. The dark web is not that. You know, it's everything else, basically. You use Tor to access it. But yeah, in terms of the Silk Road and what it sold, yes, there were a lot of drugs, but there was art, there was knickknacks, there was fake IDs as well. There was some limitations on what could be bought and sold there, for example, child porn, for example, was ruled out.

I think weapons at some point were ruled out, I have to double check that. But it wasn't like a complete free-for-all, you know, there were some limitations. But there were also a lot of dangerous things on there. There was one discussion about selling chemicals that could. could, you know, assistance side, basically. That was sellable on Silk Road. So, yeah, it was kind of a wild west in terms of a place where things were bought and sold. Well, also, you had to use Bitcoin or crypto, right? Like, you couldn't just put your credit card info even back then, obviously. So how much of the Dark Roads kind of like early success was tied in with like the crypto industry

back then? So Silk Road, yeah, was one of the first sites or first places to kind of mainstream Bitcoin. You know, there wasn't like you could, again, enter in your Visa credit card number and have a payment processor, take down your information so you could buy heroin. You needed something to also be anonymous for payments. And Bitcoin provided that, you know, it was this up-and-coming digital cryptocurrency. A lot of people didn't know about it or they saw it as kind of a speculative thing. But in this case, there was a real use case in terms of anonymizing online buyers and preventing your payments from being tracked, essentially. So you would put your Bitcoin into an account on the site. You would buy your drugs.

The money would go into an escrow account as the drugs were being shipped. And so they were literally shipped through regular mail. The drugs would arrive on your doorstep and then the money would be released to the seller. And you would use the product. You would rate it after that. Is it good? Is it bad? And in a way that you would rate like an Amazon package, it was kind of in some ways ingenious in that way.

Yeah. And in some ways it sounds like safer even or like more regulated almost like, you know, not top down, but like more streamlined rather than just like buying. drugs off the street. In some ways, and that was the argument that the Silk Road's creator made, and the Silk Road's creator was named the Dred Pirate Roberts. That was his online name.

And his argument was a very libertarian one, which is that if you rate what you're getting, you know, you can maybe tell other people how it is and make it safer. I think there's a lot of holes that argument as well. You know, what happens if you're the first person to use something from a first time seller and you die or you get horribly injured,

which happened in some cases to people who use Silk Road. But that was kind of the little libertarian argument to it, yeah, for sure. You mentioned Dread Pirate Roberts, who I think you said as a character in The Princess Bride and is this sort of like pseudonymous owner of the website. How long did Silk Road exist before it was shut down and what happened? Like when did Ross Ulbrichts get discovered and what was that process like? So I believe it was online for about two-ish years before it was shut down.

It was shut down in October. That's so short. Yeah, it was a short time, but it did, it went pretty far. And I remember the thing that really blew it up was Adrian Chen at Gop I mean, Gawker, wrote one of the first stories on it. And he said, you know, this is a place where people buy and sell drugs online. Eventually, Chuck Schumer found it and made a big stink out of it as any, I feel like, reasonable lawmaker would because it's illegal, essentially.

I mean, that was, I think that story was 2011. At the time I was at Forbes, I was starting my career. And my colleague Andy Greenberg actually was one of the first people to interview the Dred Pirate Roberts. We ran this kind of anonymized interview with the creator of Silk Road at the time. And so we were kind of along with Gawker, you know at the forefront of reporting on this and it was like very interesting to see at one point Andy did this experiment where he actually bought weed off the Silk Road and like there was a video online somewhere of like Forbes reporters buying weed and then eventually like flushing it down the

toilet but like the whole thing worked flushing it down the toilet yeah sure flush there was actually footage of it being flushed on the toilet but you know it worked and it was it was pretty stunning in how in the simplicity and the effectiveness and you know just as we were doing it I realized federal agents were doing they were trying they were trying to they were trying to figure out how this whole thing was working and trying to figure out who was behind this thing. So when did it all come to a head? When did the federal agents discover that it was Ross? And how did they piece that together? I've talked to some agents and folks that worked on the prosecution in the story. But they also saw the Gawker story in 2011. And that's when they started to catch on to this

thing. And they were also buying drugs and trying to trace them back to the sellers and then arresting the sellers and trying to figure out how they were connected to Silk Road. And it was very long. investigation, long process, that initially wasn't taken very seriously by the federal government until they realized the volume of drugs that were being passed through the site. But eventually, you know, things caught up with Silk Road in October 1st, I think 2013, which was a crazy date because it was, I think that was the week of the Breaking Bad series finale, which is this like a tale about a drug dealer. And then you get like kind of a real life version of that a week later. And so he's arrested in a San Francisco library. Federal agents kind of surround him as

he's working on his computer logged into Silk Road and they had this whole plan sting and then they arrest him there and that's when he goes into custody. Wow. So he's arrested over a decade ago. The website shuts down or the platform and then he's just in federal prison. Does he start talking to anyone or is he silent? Like does he try to defend himself or does he just plead guilty? So the trial begins in I think 2015 and he receives he gets sentenced in 2015 to two life sentences with no possibility of parole because it's a federal sentence. And at the trial, they reveal all these things. There was discussion about murders for hire, for example,

that became quite a big talking point in the story of Ross Ulrich. There were also stories of people who lost family members because they used drugs off Silk Road. And so he gets sentenced to two life sentences in the Southern District of New York. And I kind of think like that's the end of his story, you know, that we'll never hear about this guy again. I want to dig back into the comment you just made on the murder for hire.

Could you do murder for hire on the Silk Road, and the dark web? And did he do that? I don't think you could. I have to double check that, but I'm pretty sure you could not hire murders on the Silk Road. But he, outside of Silk Road or someone, attempted to hire Hitman to go after people who threatened the existence of Silk Road, threatened revealing information or blackmailing him.

That information is pretty clear and revealed in these chat logs that have been entered in discovery for the case. Oberg, in his defense, has always denied that he tried to do those murders for hire. He said he wasn't running the site. at the time. And there's a big part of this whole story, which is that there were several federal agents involved who were actually in some ways corrupt. And they had kind of entrapped him in a way, but were also extracting Bitcoin from the site and trying to extract bribes. Okay. So first of all, they have him on the chat logs as Dread Pirate Roberts, whatever, allegedly seeking hit men. And then these federal agents were running a Bitcoin scheme. Like there were two agents that were corrupt and involved in the investigation out of, I think, the Baltimore office of the FBI. So their stories also intertwined with this because they also get prosecuted and sent to prison for essentially trying to scam the owner of Silk Road.

So they were trying to scam Bitcoin out of him? Yeah, essentially, and enrich themselves. Interestingly enough, the murder for hire charges, O'Brick was never tried for them. There was a separate case where he was charged with it. He was never tried on that charge. And so a lot of O'Brick supporters believe that the murders for hire are essentially trumped up against him. and they were used to kind of solely his reputation and build a case against him.

But I think there's a lot more nuance there. And I think if you look at the chat logs, you know, someone who was running the Dred Pirate Roberts account certainly did order up hits, whether he believed them to have happened or not. He was looking to enact them. I get why his supporters would say that, but also, like, if you've got the receipts

where it's his username asking for the murder for hire, seems not great. And I should be clear here that Ulbricks, one of his main defenses, is that he did create Silk Road, but he was not running it at the time when it took off and when these alleged murders for hire. So the other person could have been, got it, got it.

There was another guy. There was another guy, yeah. And is that guy in prison? Well, that's their allegation. I mean, you know, it's never, the human team never said. Oh, it's never, okay. This guy is never sort of counterversion. Okay, so this is 2015 when he gets sentenced. I feel like that's such a pivotal year, really 2016,

is when so much changed in culture. I mean, like you mentioned... What happened that year? Some of the support... with libertarians. But like, I mean, we have 2016 Donald Trump and this kind of like, I feel like, I mean, they call themselves libertarians, but it's sort of this like crypto libertarian types of people that are so against the federal government. They sort of want, you know, maximum freedom online, some of which I support. But what happened when he was sentenced? Like, you know,

did those people sort of come out immediately in support of him? What role did that sort of burgeoning crypto movement play? I don't think you could have created an individual who would have been like more sympathetic to people that mistrust the government than Ross Ulbric. A big part of his history was that he was a libertarian in college and grew up in this kind of Anne Randian kind of way and became deeply affected and influenced by libertarian thought. You wrap in the crypto element as well of these crypto supporters who already distrust government and that's why they believe in Bitcoin. And so you get these two groups of people, libertarians and the crypto supporters who become this very big support base for Ross almost from the get-go.

As soon as the trial is going, you know, you have these large groups of supporters. Someone who is very influential in this whole process is his mom, Linnelbrick, who dedicates her life to basically rescuing her son and goes out and does all these speeches and meetings and essentially lobbying with these groups, trying to get them involved with her son's cause

of Free Ross and trying to just keep him in the spotlight. And so, yeah, those two groups kind of coalesce behind him around him and become this very, big support base, which he builds on throughout the years. And over the decade, even though he is in jail, he has this big support group. You mentioned his mom. What's his background?

Like, how did he sort of come to this point of even founding Silk Road? And what role did his family play? I mean, Olbrecht is a very interesting character. He grew up in Texas, very smart, by all accounts. He went to grad school at Penn State. I think he majored in physics and studying economics as well. And known as a smart guy, someone who is technologically savvy as well. well. And by all accounts, you know, grew up in a pretty loving household. His mom was very

influential. His dad was there. But a loving household around the time of Silk Road, you know, his goal was to create something impactful, something that he would be remembered by. You got to remember this time, you know, there was a lot of startups popping up. We're just past like the social media boom. And so he's thinking about building something for the internet and of the internet. And that's kind of how he lands on Silk Road and starts to cobbling this thing together. I believe he grows his own mushrooms to sell on the site. Those are some of the first products that are sold in the site. And then the thing just takes off. You know, it has all the elements being secretive a little bit, working well, and it becomes global. You know, you get MDMA distributors from the Netherlands selling.

You get heroin distributors. It just becomes this kind of big thing that eventually kind of grows out of his control. Okay. So he's sentenced 2015. There's this burgeoning crypto libertarian movement that's behind him. Trump comes into office, Trump won his first term. How did he get up? on Trump's radar? Like, was he on his radar back then? And like, what was his life like during that first Trump presidency? I would say not at all, not on Trump's radar at all. And you got to remember that Trump's message coming in, you know, hard on crime, hard on immigrants who are bringing in drugs to our country, you know, in some ways Trump's message was completely antithetical to Oldbrook's cause, right? Like, if you're going to be hard on drugs and hard on criminals, someone like Oldbrook should be in

prison in the Trump reasoning of 2016. And so what happens during that period is he's not on Trump's radar at all. But Lynn Olbrick starts networking with people that can get her a meeting with the administration. And the thinking there was he was going through the appeals process. It wasn't looking pretty for him. So the only way he could get out was through some kind of pardon. And the person in power that could do that was with Donald Trump. And so Lynn Oldbrick actually starts networking with a lot of kind of far-right alt-right influences at the time. I remember being in DC at a completely different hearing, you know, something for social media, like I think Twitter CEO, CEO Jack Dorsey and Facebook CEO, Cheryl Sandberg were testifying on the hill. And I turn around and I see Lynn Oldbrook sitting next to

some all-right folks. And I'm like, how are they connected? It's very strange. And it took me a couple years to realize that she was building a support base, you know, of folks that could get her closer to to Trump or to people around Trump that she could build a case for her son. It's kind of interesting the way these like mothers come out in support of their kids. Like I don't know. I was just thinking of like Sam Bankman-Fried's mother as well or like just some other like parents of people that have been charged in in various like crimes. Okay.

So he's sort of sitting away in prison. His mom is out there meeting with all of these right wing influencers trying to kind of get on get on their radar. Is he speaking to anyone? Is he saying anything? You mentioned like his appeals case was kind of going nowhere. But I think you mentioned in your story too that like he started talking to a girlfriend or I don't know if that was like later. Yeah, there are definitely media outlets, myself included, that tried to get in touch with him to very little success. And I think that was to his mom's credit of distancing himself from from media folks. But he was in our reporting in this story, we found out he was responding to people and

one of the people who responded to was this French woman who was working at some tech companies in California. Her name was Caroline DeBrion. And she just wrote him letters. You know, she became fascinated by his case and just started asking questions via written letter. And he would respond. And they struck up a friendship and then eventually kind of a romance, even though he was in prison. To the point where he's sitting in jail, she ends up becoming involved in the Free Ross cause and they get engaged. I guess there were some people that were getting to him. And he was getting his message out through, you know, his mom and this Twitter account she ran as well. So what was like the Free Ross message and movement?

What was his kind of like case that he was making for his freedom? The Free Ross argument was essentially there was a couple pillars. One, that he should not have received two life sentences. It does seem kind of excessive. There was a big argument to that, you know, and I think even some of the prosecutors were surprised by the amount of time he received. But you got to remember, you know, there were people that died from using

this thing and people got hurt. And I think the judge wanted to set an example. But the free Ross message was that the example that was set was way too harsh that Ross simply braided the site. He didn't sell or distribute the drugs himself. And they continued with this kind of suggestion that he wasn't even running it at the time that, you know, it grew and these supposed murders for hire happened that it was, it was potentially someone else. And so his mother, to his credit, continued to like hammer home this message. You know, there was a Twitter account. She had a website. She did a lot of speeches.

I would hope my mom would do the same if I was in jail, I guess. And she was relentless in this. It became a movement, a Free Ross movement, to the point where there were shirts. And the libertarians made this kind of their number one cause going into 2024, yeah. Yeah. So I want to kind of like zoom forward a little bit to, of course, Trump loses in 2020, has this resurgence.

When did this cause start to get back on Trump's radar? And who kind of brought it in? to his realm. So by the end of 2020, there was a drafted pardon or a commutation of Oberg's sentence or some kind of some version of that that got to Trump's desk. And Ollbrick's mom's efforts had largely worked. It got to the person who had the power to race this sentence and get him out. And what happened is January 6th.

And there were some elements within the Trump administration who felt like pardoning Ross Ulbricht or commuting a sentence would say the wrong message. And so Trump's last day in office. came and went. They were, there was sort of hope that would happen, but eventually it didn't. And when Biden came into office, there was simply no chance. They had no relationships with the Democrats. I don't think it was in Biden's interest at all in pardoning Ross Ulbricht. And so they kind of lost all hope by that point or lost a lot of hope. When did things change? I mean, so that's the end of Trump's first presidency. He announces he's going to run again, you know, 2020. When was that

23, 2022? How did he get back on the radar? Like, was this something that was, like in Trump's mind? Or was this something pushed by the libertarians? So his mom continues after 2020 to push for Ross's freedom. And I think what an interesting decision that was made by Ross and by Caroline, Ross and Caroline at the time,

was to participate in this documentary. There was a documentary filmmaker that approached them. And he starts to do these jailhouse interviews with this guy, Blake Harris, with the idea of doing a documentary that might change public opinion. You gotta remember at the time, there was no pardon on the table.

Maybe their best shot was putting out some kind of media or particularly participating in some kind of media that might sway public opinion and make him a more sympathetic figure. And so he starts to do about hours and hours of jailhouse calls with Blake Harris. And that begins, I think, in just around the pandemic tenor or shortly after. And who's Blake Harris? Like, is he some libertarian guy that's sympathetic to the cause? Like, how did he get hooked up in all of this?

Blake's a filmmaker. He's someone I talked to a lot for this piece because it comes up again later in the inherited. But he's just a filmmaker and an author as well. Ross just decided to trust him? Yeah. I mean, it's quite strange. Blake, I think, had written a book about Palmer Lucky, the founder of Oculus and founder of Anderil now.

And I think Ross read that in prison or something and thought that the portrayal was good and decided to trust Blake, who, to his credit, was very forthright and relentless in trying to get him to talk because he saw this as a great opportunity to make a film. And so, you know, as any reporter would or any person working to get a story would, he kind of works his source and eventually gets him to a point where he trusts him and starts talking to him for hours at a time. Where does that end up going and what year are we in now? Like, because he's just doing all these interviews, which by the way, seems like a huge liability. But I get the mentality of like, what else do we have to lose? Might as well get my story out.

But how does this progress as we get closer and closer to the 24 election? So these interviews keep happening, I think, throughout 2022, 23 and 24. And Ross is continuing to work on, you know, to talk to Blake and tell his story. But at the same time, in late 2023, Trump is kind of ramping up his campaign. And he's looking for votes. And one of the places he goes to for those votes is the Libertarian Party. He sets up a meeting with Angela McArdle, the head of the Libertarian Party at the time, and asks, like, what is your one demand? What does the Libertarian Party want for me if I were to get

the presidency? And their number one concern was the freeing of Ross Ulbricht. And so Angela McArdle tells him, you know, if you free Ross Ulbric, then you'll get our votes. Just promise that. And so Trump then goes to the Libertarian National Convention and says in a speech, you know, I will free Ross Ulbert on day one. I'll commute his sentence if you vote for me. And that became his promise. He repeated it again at another crypto conference later that year. And we're now in 2024. And it became kind of this weird campaign promise that really wasn't linked to anything else on his platform besides, you know, essentially it was a deal.

It was favor trading. And yeah, the libertarians got what they wanted. All right. So the libertarians have taken this up as their cost. Trump's like, I got you, we're going to pardon him, comes into office, pardons him, I believe, on day two. What happened next? I mean, did they just let Ross walk free?

And what did he do with his life? Like, where did he go? Yeah, so day two, so not quite the same promise he made, although he did exceed it because he said he was going to commute the sentence, which, you know, just erases the time and, you know, puts it to time served. But he issues a full pardon. So erases this from his record, full stop. And Ross walks out of prison.

his Arizona federal prison with his backpack, his gray jumpsuit, and this plant that he's carrying from his cell. I'm sure it's a surreal feeling, but someone who thought they would spend their life, whole life behind bars is now suddenly free and free to do whatever they want, because there's nothing holding them back, right? And at that time, my colleague, David Yafi Bellany,

who worked in the story with me, we wrote the story about the pardon how it came together. But we were thinking like, man, this guy's gonna have some weird shit happened. You know, there's like a lot of things that are gonna happen to him because he's reintering, After a decade behind bars, he's a cult hero in some of these communities. What is he going to do next? And so we spent the kind of last six months following him.

And I don't know what you would do if you were 40 years old and in prison for 11, 12 years and then rejoining society. Well, also, I mean, he doesn't have any money, right? Like, he's just coming out of jail. And then so, like, he wasn't allowed to keep any of that Silk Road money, right? So, I mean, do people start donating to him or what happens? The government sees most of the silver. Silk Road Bitcoin or all of it as far as I'm aware and he no longer has access to it at some point he was like struggling for cash to the point where he starts auctioning off some of his possessions from jail for for money a couple months out of jail though he receives a 31 millionish donation in in Bitcoin from this unknown account which people have now

researchers have found that it's linked to another defunct drug site called Alpha Bay so you know now he is wealthier than probably you and I he has these opportunities in front of him he's been doing these speeches. He's been giving talks. He went to the Bitcoin conference in May and spoke in front of like this cheering crowd. He's had job opportunities from the crypto industry because, you know, he is a hero to that community. He is one of the Bitcoin OGs. I mean, $30 million seems like he doesn't have to work, but he's become this figure like. What is his current life like, if you can describe it? So he didn't participate in the story, unfortunately, didn't talk to us. But as far as we understand it, I think he's moved out of Arizona and is now doing speaking engagement. These speaking gigs, by the way, are very, like, interesting because they feel like a political campaign.

He went and spoke at the Turning Points USA Conference in Tampa, the student conference, and gave a very kind of raw-rah speech initially, like, about Trump and the Republican Party, but then kind of veers into why drug laws are bad. And, you know, he's talked about prison reform. And in some ways, it's, like, a politician doing these, like, testing out these various stump speeches. It's very interesting. You know, most of these speeches are 20, 25 minutes long, and then he walks off stage to, Cheers. Very controlled environment. He's also been like posting Instagrams with his wife on this

like shared account that he has. I'm obsessed with this shared Instagram account. We all have shared in Instagram accounts with our loved ones. But yeah, this one's interesting because it's like very controlled and it's like, you know, I'm in a loving relationship with my wife and we are at the Grand Canyon and we're swimming now and everything is like a celebration of his freedom. Does he want to potentially run for political office or play a bigger role? Do you think like in our political system because it seems like he's also, I mean, he's amassed enormous power as like an influencer and as the face of this cause. But just given how intertwined he is with the political movement that ultimately got him freed, do you see a future in which he runs for office? I do, but I have no evidence of him doing it.

You know, you mentioned this idea of him potentially becoming an influencer. I feel like he's right at the beginning of that. Like he hasn't realized that he can become the face of whatever shit coin, you know, and get paid millions of dollars for it. But he is right at that point, you know, where There are plenty of people willing to sponsor him and use him as a face because he's, he means everything to that community, to that demographic of crypto users and libertarians. And I guess now Trumpers. He is indebted to Donald Trump. And at every speech, he kind of gives this impassion, this man saved me kind of spiel. It seems like the crypto world is also so intertwined with Trump still.

And I'm curious kind of what that relationship has been like. Obviously, we have David Sachs as like the cryptos are. I think he's still there. Well, he was at that dinner recently, so he's definitely still there. But, like, what is the libertarian sort of crypto people's relationship with Trump? Like, is it strengthening? Is Trump still all in on crypto? I feel like he's used it a lot to enrich himself financially.

But what is their endgame? I mean, they see him as the most crypto-friendly president of all time. He is someone that has deregulated the industry. He has got rid of a lot of the regulators and overseers at places like the SEC and the CFTC. And he's made it so that these things can flourish, I guess, and be pushed and not regulated, essentially. And yeah, the Trump family has personally benefited to the, in the tunes of hundreds of millions,

it's not billions of dollars from this, you know, Trump coin scheme and all these other crypto initiatives. So the crypto industry in some ways loves it. And if you view Ross Ulrich through that lens, it's a very smart move because it ties him further to that industry. You know, he's known as the president who saved their hero and who wouldn't embrace that. Some of when I read your story made me feel sympathetic.

to Ross because it's like he's this young guy, he makes this website. Yes, it's facilitating a lot of bad things. But isn't that also just true of like every single one of these Silicon Valley companies and billionaires? Like, I mean, haven't they all created products that lead to death and harm and like horrible things in various ways? And like, you know, he ends up with two life sentences and it seems like the rest of Silicon Valley and all these other young guys that have, you know, wrought so much harm

on our worlds, like haven't been held accountable at all. Well, I am very familiar with the people you talk about because I report on them every day. But at the end of the day, Ross Holberg did something that was highly illegal and knew that he was doing something highly illegal. You know, it's not illegal for Mark Zuckerberg to create a social media site that sucks everyone's time and attention to the point where you go down rabbit holes and believe in conspiracy theories that, as far as I know, isn't against the law. But it is against the law to distribute heroin and take money for heroin. And that's just how our society is built. I don't know if that connection is fair, but Ross Ulbricht did something that was highly illegal

and was prosecuted as such. And when you talk to the people who were harmed by the site, you know, I talked to this guy, Rodney Bridge, whose son took this LSD kind of derivative product that was made out of China and Seoul on the Silk Road. His friend bought it, gave it to him at this high school dance in Australia. And the kid thought he could fly and jumped off a balcony

and landed kind of an iron fence and impaled himself, essentially, and died. Those are the people that get harmed by this stuff. And I think about like negative externalities of not just Silk Road, but when I report on Facebook or Twitter. And when you talk to those people, you can really see pain. And I sympathize with that. So yeah, I'm not someone who's going to like judge a sentence

and think it's like too harsh or too easy, but like that's what Ross got. The Silk Road shut down and now we have just the internet sort of explosion throughout the 2010s almost like after he kind of went away. It seems like there's this move towards this more decentralized internet with crypto and just less accountability, Also, have there been Silk Road copycats? As soon as Silk Road 1 went down, there was a site called Silk Road 2.0 that came up. There's definitely been some that have been arrested and sites that have been shut down.

I think this will continue. You know, it's just something that will exist and people will hop onto the next thing and the next thing. It'll be a kind of game of whack-a-mole. But in some ways, Ross Ulbricht was the first and the O.G. And the guy that popularized it. So he'll always be remembered in that way. Okay, so Ross is a free man. Whatever happened to that documentary?

So Ross, interestingly, has been trying to kill it and is very fearful of it to the point where he offered $1.77 million to buy it, so it wouldn't see the light of day. And I've heard audio recordings and scene tape. And basically the answer or the reason why he wants to do that is because he thinks he's said too much on these tapes. You know, there's 80 hours of it for this filmmaker. I guess he believes he implicated himself in some ways or is worried about what that's going to be made into a film, which is kind of a ironic given that he was the one that participated in the first place. Well, and wasn't it supposed to be like a positive film meant to like help his PR? I think that was the thinking behind it, you know, something that would make him more sympathetic.

But the whole point of doing that was to change public opinions so you could lobby for release. And if you're already released, it means nothing to you anymore. Now it's just a liability. Right, it's a liability. And it's, it gets in the way of potential earning opportunities. You know, he wants to write a memoir. Maybe he wants to make his own movie. And if his memoir,

doesn't match up with what's in the movie, people are gonna ask questions. It's very interesting and says a lot about a guy, you know, who wants to control his story. And it makes me think about the speeches that he's giving now, and he loves talking about creating Silk Road. He loves talking about being in prison.

But there's kind of that gap where he doesn't talk about in the middle, and because it's the stuff that I think makes him most uncomfortable. And it's probably the reason why he doesn't want to talk to a journalist, because those journalists are gonna ask him those very questions. Did you run Silk Road in the era, you know, in 2012, 2013 when it got very popular?

Did you order up those murders for hire? And I think those questions get to very uncomfortable places for him, and that's why he's been very controlled in his appearances. So the documentary filmmaker did not take the 1.77 million? He did not. He thought he'd be compromising his ethics to sell his film back to his subject. But he did counter with something like a $10 million. He's like, you know, if you could be $10 million,

you know, maybe I'll think about it. And I think that kind of cut off negotiations at that point. And so as far as I know, the documentary is still kind of full steam ahead. They're talking to distributors. Now it has a different ending because Trump pardoned him, which kind of changes the film's trajectory. And yeah, I think it's in the works. Has a streamer bought it or anything?

I think there's conversations right now. So I think eventually they'll get to that point. All right, Ryan, well, thank you so much for chatting with me today. Thanks for having me. All right, that's it for the show. You can get bonus episodes of Power User on my Patreon. Don't forget to subscribe to my tech and online culture newsletter, usermag.co.

That's usermag.com, where I'm where I write about all of this stuff and more. If you like this show, please give us a rating and review on Apple Podcasts, Spotify, or wherever you listen. I'll be back next week with a brand new episode. See ya then.