The Dread Pirate Roberts has a mom, and she'll never stop fighting

An interview with Deep Web director Alex Winter and Lyn Ulbricht

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Today a judge sentenced Ross Ulbricht to life in prison for charges stemming from his involvement in the online underground marketplace Silk Road. Allowing its users to hide behind Bitcoin and the anonymous Tor network, Silk Road became a haven for the online drug trade before getting shuttered two years ago. Federal authorities named Ulbricht as the man behind “Dread Pirate Roberts,” the shadowy persona that masterminded the site.

The stork of Silk Road — and some of the still-unanswered questions surrounding the investigation into Ulbricht — caught the attention of Alex Winter, who’s transformed himself from the actor that once appeared in Bill and Ted’s Excellent Adventure into the director of movies like the Napster documentary Downloaded. The result is Winter’s new documentary Deep Web, which premieres this weekend. Earlier this year at SXSW, I sat down with Winter and Ulbricht’s mother, Lyn — who has become an outspoken advocate for both her son and Fourth Amendment rights — to discuss the film, Ulbricht’s case, and how governments and industries are fighting a losing battle against the inevitable tide of technological progress.

Bryan Bishop: Alex, what were the origins of the project — how’d you get started?

Alex Winter: I made the Napster movie, and this is a sort of continuing conversation about global communities and people whose motives were misunderstood. Not necessarily because they were great or bad or whatever — but they were not represented properly. And I was interested in continuing to tell the story of what the implications are of the internet right now as we shift from the industrial to the technological age, and what a lot of the motivations are for people who are doing things within that area. Privacy and anonymity advocates, including people who like moving contraband around — all kinds of stuff is going on there. So it was really just trying to create a more nuanced view. That was the motive.

The deeper I got into Ross’ case and the implications around it, the more I saw that a lot of the biases against these movements were creating a very black-and-white and inaccurate representation of what’s actually going on, and then I had more to chew on and more to tell as a story.

Lyn, what were your feelings when Alex approached you? You’ve obviously been very active in bringing awareness to Ross’ case, but was there some trepidation there?

Lyn Ulbricht: I do have trepidation about media, and [initially] I told him no. And there were other documentaries; there were about five, and I told them all no. But over time we reconsidered Alex because of his prior work. We had a verbal conversation, and Alex has a lot of integrity, and it just comes across. So I thought, okay, I’ll do an interview, and then once we met I realized he’s going to see the big picture. I can trust him not to do a "gotcha" on me and misrepresent things, and so I became more and more involved, and I’m very happy that I did.

You touch upon the ideology expressed by the Dread Pirate Roberts, and there’s this kind of idealistic, almost pacifist sentiment in the beginning. Whereas some of the people you talk to later, like [Bitcoin entrepreneur] Amir Taaki, are much more aggressive and hostile. Do you think that original idealistic sentiment is the reason the Silk Road community came together in the first place?

AW: Oh, completely. It’s the same thing with Napster. These things, they [come together] because there’s some form of ideology that sort of permeates it. There’s no doubt that was the glue, but again — that’s not new. It’s sort of what we talk about in the movie; that kind of ideology has been around since the beginning of the internet. It’s what drove the creation of the internet. People can get confused, or they like black and white — so they’ll swing from one side of the fence to the other. But it’s not about libertarianism, even. There are libertarians that are part of this movement. There are super pro-government, Randian capitalists that are part of this movement. It’s everybody. What tends to [unite] these people is sort of a mutual awareness of the implications of the digital age. A desire for privacy, for anonymity online, for rights online, and an understanding that if your rights are being breached online, they’re being breached in the physical space, too. So I think it tends to attract those kinds of people.

"If your rights are being breached online, they’re being breached in the physical space, too."
Deep Web promotional image (EPIX)

Amir Taaki and Alex Winter.

There’s a line in the film where someone says you’d be foolish to think the NSA hadn’t illegally hacked into Silk Road’s servers. Has it been disturbing to see all the revelations from Edward Snowden and others roll out over the past few years, or does it just feel commonplace to you at this point?

LU: Well I read 1984. I think about it often. And they have the technology now, you know? We don’t know how they found that server [that helped incriminate Ross]. They have this bogus claim that very eminent experts have said isn’t true. And they said, "Even if we did hack into it, it’s okay." It’s an important Fourth Amendment issue.

Silk Road got shut down, then there was another Silk Road. Now there are distributed and decentralized marketplaces out there. Ultimately this comes down to an ideological fight between that community and the government. What do you think the endgame is going to be?

LU: I don’t see how they’re going to stop it.

AW: It’s very similar to Napster — even technologically speaking, as you said. You now have these decentralized systems that are going to be proliferating, and I think that reality of it is that it is a game of cat and mouse. The technologists are usually a step ahead of the reaction to the technologies. I think that there’s no easy way to transition a culture from one giant age to another, so there [are] no easy answers. There [aren’t]. People get bent out of shape; I dealt with it on Downloaded. You have to really just try to examine the nuance of how we got here and what the motives are, and where we’re making mistakes as a society so we can try to correct those mistakes and deal with this stuff in a more humane fashion, because it’s not going away.

And I think underneath all of this really, is this deep-seated shift in power and the way culture works. And that’s beyond any one person that you can blame. It’s beyond Shawn Fanning, or whomever you want to say is responsible for these big changes. These are giant cultural changes, and we tend to demonize them and criminalize them and there needs to be enforcement, obviously. I’m happy that cyber investigators are getting real good at cracking down on child pornography and human trafficking, and that’s important, and that uses the internet in a large way. But these movements that have grown up online are important, and they’re important for human rights, and it’s important that we have privacy and anonymity online. It may be unpleasant for people, but you do have to be surgical. You really do have to pick apart each of these stories in fine detail before you just throw people away for life, or for posting a hyperlink, or whatever it is they’re doing.

Russ Ulbrich in Deep Web promotional image (EPIX)

Ross Ulbricht in prison.

It’s this odd side effect of being in an era that’s all about disruption. The minute any established interest gets upended, they react and spin up narratives designed to suppress that progress — and now the government is reinforcing it in many ways. At what point does it stop? Is it purely a generational thing?

LU: No, I don’t think so.

AW: I know a lot of people who were kinda pissed at me for making Downloaded and not just hanging the Shawns from a tree for taking away their vinyl. And they really couldn’t listen to a more nuanced argument. We’re not saying they’re heroes [in that movie]; we’re saying, look at this with a more nuanced perspective as to what their motivations were and how we got here. People have a hard time doing that. And I’m bracing myself for that with this [film], because the stakes are so much higher. You’re dealing with drugs, so people I’m sure are really going to wig out. "How can you be looking at this with anything other than these are all evil, horrible people that should just be thrown away for life?" And I’m ready, willing, and prepared for that response.

"25 years from now we’re going to look back at the weird witch hunts that are going on now."

But it makes me sad because I feel like [people are] not really being open-minded enough to look at shades of grey; your brain just swings from one pendulum side to the other. And that hard thing about working on this movie is when you’re dealing with something like Ross’ story where the implications are so tragic, it’s hard to be philosophical and go, "Well, everything’s going to be okay in the end." But I do think the longview, sadly, is actually probably pretty positive. I think that 25 years from now we’re going to look back at the weird witch hunts that are going on now and go, "Jesus, do you remember when we did that thing, and these people were sitting in jail for blah-blah-blah?"

And now you look at BitTorrent, which is becoming this completely aboveboard, successful mainstream [company], which is just what Napster wanted to do. And now it’s okay, and nobody’s calling for their head on a platter. To watch that happen is a little troubling, and it’s daunting, but I do think in the end…. it’s not really a generational thing. It’s a technological comprehension and acceptance thing. Because [EFF co-founder] JP Barlow, who is an older gentlemen, is probably driving as much positive change in this area as some 18-year-old who is really good at Tor. So I think it’s about what you know, and whether you’re willing to engage in these more mainstream, unpalatable conversations.

Deep Web premieres this Sunday, May 31st on Epix.