Interview: Alex Winter Ventures Down The Silk Road In DEEP WEB

For those of us in our third (or fourth) decade, we cannot help but think about Alex Winter as the actor who played Bill S. Preston, Esq., the curly haired co-protagonist, who along with Keanu Reeve's Ted "Theodore" Logan, traveled through time to learn about historically important figures in Bill & Ted's Excellent Adventure.

That was then, this is now. After a brief foray into directing fiction with the delightfully weird prosthetic-effects sideshow Freaked in 1993 and the quietly (but positively) received 1999 thriller Fever, he has been making documentaries that delve into the legal, moral and ethical morass that technology has a way of remaking our world. And in spite of reuniting with his excellent pal, Keanu Reeves provides voice-over for his latest film, the goofball feel-good shenanigans of 1980s cinema are well into the rear-view.

Alex Winter is almost 50, but has an enthusiastic and easygoing gift for gab. Had I strayed from the rather serious subject matter of Deep Web, his documentary on crypto-currency, anonymous communities, and the fate of Ross Ulbricht, one of the founders of The Silk Road, the infamous online black market at the hands of the US justice system, Winter probably would have likely, happily indulged my inner fanboy. In a rare fit of professionalism, I kept on topic and we spoke not of being excellent to one another (although we kinda did that in a round about way) but rather about the many thorny tendrils exposed when the American Constitution goes up against The Dread Pirate Roberts.

My review of the film is here. Below is an abridged version of our conversation.

Alex Winter: It's very hot off the press, Ross's sentencing is in a couple of days [editor's note: May 29, 2015*] and we are going to put that in once we know what the sentence is, other than the the film is absolutely done. That was challenging but like anything else in documentary filmmaking most of the challenges are assets (and most of your assets are challenges.) [*Laughs*] It was in progress insofar as I have been tuned in for many years to the changes within internet communities. 

My last film, DOWNLOADED was with a very specific group of people, which is really how I was looking at Napster as the first really big global internet community, and so I was very aware that changes in the way the internet was functioning were accelerating and that Bitcoin was going to produce something big, but it had not happened yet. Then the Silk Road happened, and when Ross Ulbricht was arrested in October 2013, Mark Shore (who worked on DOWNLOADED) called me, and he said, we should be telling this story, because we are already in it. I agreed, even though I knew what I had in front of me was somewhat daunting. 

Some of the players were the same, I was already talking to people, so we just hit the ground running. I knew a lot about this Cryptography, The Darknet, Bitcoin, and had been researching various black markets since the late 1980s. This was not anything new, but what I realized that The Silk Road was the Napster of this era, it was the brilliant combination of the anonymizing power of TOR, the fluidity of Bitcoin and the gigantic size of its online community. That is no prescience on my part, that is flagrantly obvious. 

The story was happening, and it is still going on of course. You could take the really-long view position of the story and just do interviews and compile information and put this out in three years when the dust settles. I did not want to do that this time. Napster was that. 12 years on that story. I wanted to tell a different kind of story this time, one that was happening in real time. Ross is arrested. Ross goes to court. I wanted to put a terrarium on top of time, and just say from here to here, this are the facts of what happened as I saw them.

Absolutely. He is the protagonist of this story. To his horror when he saw the film [*Laughs*] because he did not have that idea when I was was doing it. The movie is about his realizations, his opinions from his perspective on these things. That occurred to me fairly early on, we optioned his book on the subject, "This Machine Kills Secrets" fairly early on, before we did any crowdfunding for the film. 

We knew the movie needed a guide. And this guide had to be both technically adept, knowledgeable and relatable. I could have pulled a Michael Moore and stuck myself in the movie, but I didn't. That is not very dramatic, it is distracting; who really who wants to see 'Bill on the Internet!' I really liked Andy's curiosity, his humanity. We shared a lot of ways in looking at this world, the kind of outrage when Napster happened, he has for these stories. 

For instance, here all everyone was talking about was drugs and murder, and where is the historical precedent? Where is the crypto-community who created this 25 years ago. He asked about the real implications of the story. He was a real emotive way in. I did not want him to put forward my themes, there are things that we disagree on, that is fine. I don't want the film to be a just a thesis. 

I did not go into it with that intention. If you are being honest, there is no way to avoid it. I did not want this film to be a manifesto, or even a piece of advocacy, but there is a sense of outrage that is hard to hide when there is such a discrepancy in terms of the facts presented on television, the way this story is being told. The combination of malfeasance and ignorance, there is almost a premeditated intention to construct stories that are both superficial and misleading. I can excuse the lack of understanding of the technology, there is a lot of unknowns. 

I don't feel ethically or morally OK making proclamations that have not been proven out in court, when peoples lives are at stake. For me, sitting in the trial, X and Y were not clearly conveyed, and I was left with a great sense of unease. I still do not know. I thought I would end knowing categorically what had actually happened in the life-time of the Silk Road, that was something unforeseen when I started making the film.

Well, you can say these these things ("We Will Not Make Another Bill & Ted Movie!") but then you and I are sitting here having another conversation in five years. I would like to not make another one, If facts appear that are so shockingly revelatory, it would be hard not to, because of my current access and emotional connection to the story, and not just the Ulbricht case - the whole gamut, but I would like it to be just a story about the unknowability of the whole internet, anonymized communities, crypto-anarchy, the drug war. 

The difficulty of trying cases like this in court, why it is difficult, the unknowability. To me, my telling of the story is over. I wanted to be done now. I did not want to wait another year.

There will be a lot of movies made on this subject. I am aware of at least five in development, who knows how many of them will be made, but I am sure I will be outraged at a few of them. But I would like to be done if possible. 

Nobody had access to Ross, not me, not 60 Minutes, not anybody, it was a non-starter. The fact we managed do a few email exchanges and put them in the film is perhaps a bit superficial, but it did not run counter to my theme. The movie is about the unknowable and the anonymous. 

So many people around technology have a strong opinions on things ranging from anonymized communities to Who is Steve Jobs. They are all in opposition to one another, and perhaps all wrong. Nobody knows. Take Steve Jobs. One guy thinks he all around is an asshole who ignored his kids, the other thinks he was a heartfelt humanitarian. Every story does this to a degree, but technology stories seem to do it more extreme. Things are multifaceted and the internet adds its own multiplier. 

On the storytelling level, I like the Rorschach test of Ross Ulbricht. He is either this libertarian crusader or he was the Antichrist. Or, as Cody Wilson says in the film: "Maybe he did try to kill those people, and I still think he is a hero." So many perspectives on who this person is, and the person is not there.

There was stuff I could not put in for legal reasons, there were other elements that might cross ethical lines with the ongoing trial. I did not want to insert myself into the trail, nor have an impact on the outcome one way or another. If I had some bombshell truth or something, maybe. But I know a few of the architects of The Silk Road who are at large, but they are sources, and that is who that runs. 

Variety Jones in there because he is an example of just how many people are embedded in the the story of The Silk Road. From what we know, Variety Jones had extensive history going back to the late 1980s, in the BBS/UseNet era. These people were using encrypted email back then. Global business people with wives or children with savvy on the political side, the business side and the technology side of things. 

He is one of these types of people. Mark Karpelès [ed: The CEO of former Bitcoin Exchange Mt. Gox] comes up in the trial. Whether Karpelès has any real culpability we do not know. But what we do know is that there are a lot of very sophisticated people in these communities for a long time. 

Is there a survival instinct there? Its is a community until every three letter acronym government bureau comes down on it, and then things scatter.

Completely. People bail. These things have a shelf-life and it was evident. People who have been in these communities for decades are very aware, they know it is a matter of time. These things will be riddled with law enforcement the second someone hits 'Enter' and puts it online. 

They know that half the people they are trading with are law enforcement. They are transitory, they will do something in one place, then migrate to another market. They have been doing this for decades. It was very technologically cumbersome to do in the 1980s and now it is a hell of a lot easier. Once it becomes decentralized then we are off to the races.

Yes. It is a collision of problems. It is such an ass-backward movement to counter these technologies by pre-existing industry. It doesn't accept or understand the technology. Years and years down the road the same tactics and rhetoric are being used even as the technology changes. 

That tells you a lot. The fear, uncertainty and the sheer bureaucratic complexity of changing business models and the law. Then you add on top of that, the motivation of the Drug War, prison privatization, you start to pile on some very thorny issues that are not going to be easily solved.

Whatever the government does to Ross Ulbricht, it will be very sad for Ross, but it is a footnote in the story being written of the privacy for citizens vs. the government. As things step from the backrooms of the internet, to the running of the show, that is the world we are heading into.

I don't know. I don't know enough to say. That is the conundrum. If I step out and say Ross Ulbricht is a martyr, then I've drank one kind of Kool-Aid, if I say he was a well-intentioned and naive kid that got in over his head and became corrupt with power, then I've drank the other guys Kool-Aid. I don't think we have enough information at hand to make those kind of statements yet. 

It is one thing for Lynn and Kirk who know their son, and they know here he was the whole time The Silk Road was going. They have this very specific understanding of not only Ross as their sweet little boy, but where guy was, when he is accused of doing X and Y. Which is why they say, "There is no fucking way!" That is their understanding. I do not have that. For me, I have an opinion. When things go wrong, they are when very hasty proclamations go one way or another. The media making things black and white does not help us. 

What I will say about Ross, he is a casualty of this age. Given the things he had to say, he was aware that the world was changing, and he felt that there needed to be more of an impetus to use technology to move us forward. Now if suddenly everything went to hell in a hand-basket for him, we might never know. Maybe one day, we will get a trail that gets both sides to talk, maybe then we will get some satisfaction. I don't think we've had that trial yet. 

When you are dealing with other large charges, like drug kingpin for instance, sometimes the prosecution will not go after other bigger charges, because there are already a big sentence attached to the former. To put the burden of proving that he committed murders, knowing what we know now in light of various corrupt federal agents, they knew that going in at the time. 

To answer your question, it is not uncommon, but in this specific case, there were very clear-cut reasons to prosecute some and not others. If I am prosecutor, and I am thinking I have got this guy for what I view to be drug kingpin charges, why would I stick my neck towards this bucket of crap with corrupt federal agents.

There is hope. There is now brought to light pending indictments of law enforcement personnel. I think they feel there were not allowed to present a clear picture of how The Silk Road worked. To their point, it is hard to know. One agent presumably stole close to a million dollars in Bitcoin. When you are talking about that kind of money, and these kind of schemes from people who know the technology so well. 

How can you not argue the possibility of Ross's computer being hacked. Or that someone wasn't using his computer name and login to write his journal entries. There are not that many of them. Only three big ones. How hard would it write, 2011 this, 2012 that, 2013 et cetera. This is not my argument, but that is what the defense is arguing. For me, as an observer, I would be very eager to hear that side of the story, more detail. 

You have to look at the whole picture. The picture is very intense. Dialectical. There is a lot of internal conflicts. We have to understand that whether we like it or not, there is a consequence of actions, and yet the motivation that is there. A lot of these guys philosophy is that the drug war is a disaster, maybe it should circumvented. But if we decriminalize drugs, and get them out of the larceny bucket and into the metal health bucket where we can deal with them. 

But holy shit, what will that world is that gonna be? That is the fact. That was a part of their motivation. We are in our infancy of these sort of things. We are not where we are going to go, yet. These guys are so far ahead of the curve, the rest of us have not caught up to them yet. Be it copyright law and Napster, or the drug enforcement morality and ethics, and the Silk Road. We have not caught up to the fact that in the future, we might not have a drug war, we will have online drug services. There is a whole lot of work to get there, but these guys were like, fuck it, he we are. Deal with it. 

Now we have to get there. Who will die between now and then because now we are dealing with lives, not just Madonna tracks. What is going happen? What is the path going to look like getting there? You can't just hit it with a rubber stamp and say, "Illegal!" and put it away. It will never be put away, so you are missing a whole chunk of the point. 

Of course, in whatever way, the whole world is like that today, unarguably. The story is not going to stop, but the movie for me, for now, is done. We'll see.

Yea! Thank you.

*Since Ross Ulbricht's sentencing was pushed from May 15th to May 29th, it may not appear in the final version of the film, as intimated in the above interview, which took place during the HotDocs Film Festival at the end of April, 2015.