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Interview: Alex Winter on DEEP WEB, Silk Road, and The Trial of Ross Ulbricht

On Friday, May 29, 2015, Ross Ulbricht was sentenced to life in prison. The 31-year-old was found guilty on three drug counts relating to narcotics distribution, one count of a conspiracy to run a criminal enterprise, as well as charges of computer hacking, money laundering, and distributing false identification. Why? Because of his role as the founder of Silk Road, a difficult-to-access, anonymized digital market that specialized in selling some of the purest narcotics found anywhere. It was believed to have been a billion dollar business with a robust community of users from around the world. Ulbricht, for his part, steered the ship under the pseudonym “Dread Pirate Roberts”, a nod to The Princess Bride.

So, how exactly did a recent college graduate with a strong interest in libertarianism and the Austrian School of economic thought become an international drug kingpin? That is precisely what Alex Winter examines in his new film, Deep Web, which premieres tonight on EPIX at 8pm. The film itself offers a fascinating glimpse into the world of digital black markets, the next wave of security-minded internet users, and, of course, the strange saga of Ross Ulbricht and Silk Road.

Before we dive into things, here’s a basic rundown of how Silk Road works: As part of the deep web or dark web (scary terms for a portion of the internet that isn’t indexed by standard search engines), Silk Road is accessed via a browser called Tor, which anonymizes a user’s IP address and identity by routing it and rerouting it through a volunteer network of thousands of different machines, obscuring it to the point of near-undetectability. Once connected to Silk Road, users could buy and sell pretty much anything they wanted, including heroin, cocaine, LSD, and much more. For a more detailed history, I highly recommend reading Andy Greenberg’s two-part series for Wired, “Silk Road: The Untold Story”, which is incorporated into the film too.


To take you deeper into this weird, hidden world, I caught up with director/writer/producer Alex Winter to talk about his new film, Deep Web. In our wide-ranging discussion, we talk about how he first discovered this world, the moral grayness inherent to this story, the future of open-source technology, and, yes, Bill and Ted 3.

Nerdist: What first fascinated you about the deep web and the dark web, and more specifically, what about the Silk Road grabbed your attention and made you want to make a film about it?

Alex Winter: Well, I made [Downloaded], the movie about Napster, and I’ve been very interested in online communities since they appeared in the ’80s. I first started exploring online communities at that time. I really felt a desire to tell a story around that world. But frankly, when Ross Ulbricht was arrested in 2013, it really alerted me to the significance of the Silk Road. I had been following it, but the size and scale of it, and really feeling like it had become – it was sort of like a Napster redux, and sort of like Napster all over again.

So here was this giant, watershed moment in technology where Napster was the first time we had 100 million people on the internet ever, except once before, and it was just a huge sea change in human culture. So here was the first time we had a giant anonymous internet community. It was a million people online in one community, using a cryptocurrency that they could anonymize, so there was complete privacy, and everybody had the ability to trade whatever they wanted outside any kind of government control. It was just a huge, huge issue, and clearly was going to be the beginning of a whole new era, like Napster.

I looked at Silk Road and thought “This is the beginning of something; it’s not the end of something.” So that was another motivator, was to sort of look at another giant watershed in the culture.

N: Why is anonymity is so important to this sort of new breed of internet user?

AW: Because, you know, since the beginning of the internet, there have been people who realized there was going to be a need to create privacy in this space. That as the internet grew and became a ubiquitous part of all of our lives that we were going to need that privacy, just like we do at home. And they foresaw the challenges that we face today around privacy. Like, look what happened with the Sony hack, and with the Target hack, where people’s medical records are being exposed online and stolen. Social security numbers, and photographs of their children – it’s just that’s the world we live in today.

And so the dark net was first – creative dark net is a section of the internet that’ for privacy and anonymity of these special applications and tools to access it. That was originally created by the U.S. Navy. One of the main tools is called Tor. And then it was sort of spread out amongst other people for privacy and anonymity: journalists, dissidents, other government agents around the world. And it also began to be used by privacy activists, and then more radical people, like the people who created the Silk Road, who were interested in black market – creating free markets that were outside government control.

So it’s – frankly, it grew out of a privacy and anonymity movement, and then like everything else that evolves with technology, it started to be used for all different kinds of things.

N: Silk Road seems to be something of a double-edged sword because being able to conduct affairs without fear of being identified, can lead to it becoming sort of a haven for illicit activity…

AW: Let me qualify what I’m saying. I’m not saying any of this is a force for good. I’m just simply saying it is. It is, like any other community, filled with every different part of human nature. It’s like any other community. It’s filled with all different kinds of people, with many different kinds of motives. Part of what I wanted to do the film about was showing the motives of the people that created these markets. It was not to exonerate them, or to say that they were good. It was simply to look at the messiness and the multi-sidedness of these services, and of these issues that we face.

In fact, without siding one way or the other of saying “These are all good,” or “These are all bad.” I would maintain that you can’t accurately side with them wholly one way or the other. There’s too much gray; there’s too much nuance. And frankly, they’re just too big. There are too many different kinds of motives. One person may want to have a big part of the Silk Road in order to combat the drug war, and sort of create a marketplace that would allow higher-quality drugs to be sold, and to be able to communicate with each other, and for there to be less violence and less harm in the drug trade. Someone else on the Silk Road might have just wanted to get rich selling coke!

You’re dealing with a marketplace that was quite expansive, and it was all being used by anonymous users, so there isn’t one specific type of person you can point to. You can point to the motives for why these marketplaces were created. You can explore those motives, because they were largely political. Again, you may think they’re good, you may think they’re bad, you may think they’re somewhere in-between, but they are political.



The FBI takedown notice after they seized Silk Road.

N: When Silk Road is shut down, it’s like a Hydra — two more heads pop up every time. In particular, I was fascinated by this sort of new generation of cypherphiles that you focused on in London. Where do you see people like this taking these open-source technologies in the years ahead?

AW: I think that we’re at the very, very beginning of privacy movements. I think that in wake of Snowden, and the wake of these big corporate hacks, I think the average citizen is now aware that they’re very vulnerable, and they are slowly taking steps to protect themselves online. So I think we’re at the very, very beginning of privacy movements, and I think that people like Amir Taaki, who was in the squad in London who is an expert open-source programmer, is one of many people who are developing privacy and encryption tools and protocols to help the average person – to help sort of the ‘common man,’ for lack of a better way of putting it.

So you’ve got people like Amir, but you also have people within sort of regular, corporate industry who are going to be developing privacy and encryption tools that become part of your everyday internet experience – your everyday cell phone experience. We’re at the very, very beginning of that.

N: What was the most surprising or shocking thing that you learned while making this film?

AW: Man, every day – every day. [laughing] Oh my god, I don’t even know how to answer that. Every day was like, “Really? Seriously? All right, let’s go follow that lead.” I mean, it was literally a revelation a day. Every interview we had, we were like “Oh. My. God.” And then I finished the movie and I think I’m done, and then these two corrupt agents get indicted, and we learn all this stuff about what they were doing. It ties up all these loose ends I had wondered about, and so the case – it turns out these rogue cops are behind it.

And I mean, it was just – every day it was a revelation. Every single day, honest to god. I knew going in that there had been this privacy and anonymity movement, and that it had started in the ’70s and ’80s, and grown up on the internet, and gotten bigger and bigger, and blown up the dark net, and markets had kind of taken hold and gotten bigger and bigger. Suddenly the Silk Road had been started with a combination of this libertarian ethos and the desire to use technology to change drug war policy, and all of that was just the tip of the iceberg. There was just so much every day that I was learning. I wouldn’t even know how to boil it down.

N: I have to imagine that the way the Ulbricht trial kept twisting and turning, that must have made it a little difficult on your end to sort of plan out the trajectory of the film.

AW: Not really, no, because the trial was very short, so it wasn’t. It didn’t make it hard. I knew going in that I wanted to show the end of his sentencing, however he was sentenced. So that was my goal post at the end. That meant however long the trial took, I would just keep working on it until the trial was done and he got sentenced.

And because the movie wasn’t about his trial, it wasn’t incumbent on me to do much other than explain what happened at the trial. As I do in the movie, prosecution said this, they presented this – Ross’s diary, they tied the Bitcoin back to him – that’s their end. The defense then says “Well, Ross wasn’t DPR, his laptop got hacked,” that’s their response. End of story, he’s convicted, and then we will put his sentencing in as we get it on Friday, and that’s the end.

Had I had a more open narrative approach, like “Now let’s see what happens on appeal, let’s see what happens with these two Federal agents, let’s see what happens with these other drug markets that are appearing,” I’d have another year or two ahead of me, no problem.


N: Realistically, do you think there’s any hope for appeal for Ross? It seemed like the trial had been so politicized and already tried in the court of public opinion that it’s kind of a moot point.

AW: Umm – I don’t know. I have to say that that’s where I would plead a certain amount of legal ignorance. I’ve been told both. I’ve been told that there is room for appeal, given the revelation with these two corrupt agents, and the question on how the Silk Road servers were found. Other people have told me that they have a very slim chance of winning an appeal.

I’m a filmmaker; I’m not a legal expert. The movie is very much about letting other people speak their opinions, rather than me saying it’s X or Y.

N: No, I agree. I think you presented a very balanced account of all the things that were happening. On the one hand, you see this person who is seemingly being persecuted by the government, but on the other hand, he was also complicit, seemingly, in these activities.

AW: Exactly. Exactly. I mean, I think the film – and frankly, I think the story on its own without my presentation, is interesting because of the contradictions that are inherent in it.

N: This film raises a lot of concerns, obviously, and questions about security and how you conduct yourself online. Do you have a piece of advice or a step that the average person can and should take to improve their online security?

AW: Yes, absolutely. They should start with an attitude check, which is just that they have a right to privacy. They should protect their private information, and they should know that privacy is not dead, and is something that can, and needs to be protected. Taking steps to protect your privacy in the digital space, once you’ve made an internal adjustment to your attitude is actually extremely easy, but it starts with that attitude.

If you have a resigned attitude – if you have the attitude that you have nothing to hide, so you have nothing to fear, well then you’re just waiting to get hacked. Once you do, you will have, I guarantee you, a very different attitude.

N: Oh, yeah! I was caught up in that Target hack, and I was much more protective afterwards!

AW: Yeah, it sucks! I’ve had my credit cards, my identity hacked for my credit cards, twice in the last two months and it’s a drag. It’s very violating. You only need to have that happen to you once you realize that you actually have a lot that you want to hide, and that you should hide. And then you can start to take steps to hide it.

N: Do you think those hacks were at all connected to the work on Deep Web?

AW: No, no, no! In fact, quite comically, I had the capability of tracking down – not the identities, exactly, of who did it, though I could have taken that step, had I cared to. But I was able to actually find these people, and both times – I think it was the same people twice, so they must have some way into my something. But both times it was these two seemingly young or very immature – it was kind of like getting – it was two young Valley guys in San Bernardino who were doing nothing but ordering Domino’s and playing PlayStation.

And it was like Domino’s, Domino’s, Domino’s, PlayStation, PlayStation, PlayStation, Domino’s, Domino’s, PlayStation. And it was like both times I got hacked, that’s what the charges were. [laughing]

N: Gotcha. Very high level, important stuff. [laughing]

AW: So I don’t think it had anything to do with my work with Deep Web.

N: That’s a relief. I just have one more question before I go. Can you give us any updates on Bill and Ted 3?

AW: I do not currently have any of value, and given that you guys are Nerdist, you are on the cutting edge of the universe, so it would be remiss of me to try to fabricate something out of clean, hot air. I got nothing for you at the moment. We’re working on it, it’s all good, and hopefully I will have news, and when I do, you can be damn sure you’ll get it early.


Silk Road founder Ross Ulbricht

Deep Web premieres tonight at 8PM on Epix.


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