DOXA Film Festival Interview: Alex Winter (Deep Web)

Deep Web gives the inside story of one of the the most important and riveting digital crime sagas of the century — the arrest of Ross William Ulbricht, the convicted 30-year-old entrepreneur accused to be ‘Dread Pirate Roberts,’ creator and operator of online black market Silk Road. The film explores how the brightest minds and thought leaders behind the Deep Web are now caught in the crosshairs of the battle for control of a future inextricably linked to technology, with our digital rights hanging in the balance.

Deep_Web_PosterIn addition to being the only film with exclusive access to the Ulbricht family, Deep Web features the core architects of the Deep Web; anarchistic cryptographers who developed the Deep Web’s tools for the military in the early 1990s; the dissident journalists and whistleblowers who immediately sought refuge in this seemingly secure environment; and the figures behind the rise of Silk Road, which combined the security of the Deep Web with the anonymity of cryptocurrency.

Anticipating the Sunday, May 3rd screening of ‘Deep Web‘ at the 2015 DOXA Documentary Film Festival, we spoke with the film’s Director Alex Winter on constructing a cohesive documentary narrative, his relation to objectivity in non-fiction, the importance of the Deep Web in a surveillance state, and more.

The 2015 DOXA Documentary Film Festival takes place April 30 – May 10, 2015 in Vancouver, Canada.

Find more information & tickets to ‘Deep Web’ at the 2015 DOXA Documentary Film FestivalHERE

Was there a specific moment where you realized this was a story you wanted to tell at the feature length level?
I’ve been involved in these technologies for a long time so I’ve had an interest in them since the late 80s. My last film ‘Downloaded’ was about the birth of Napster that looked at it as the birth of a large scale internet community.  The success and ubiquity of the Silk Road, and what it ushered in, really represented a new phase in this movement of combining gigantic internet communities with an anonymity aspect.  This was something I thought deserved a story.

As the documentary is titled ‘Deep Web’ as opposed to “Silk Road,” did you always have the intention of focusing on this one destination?
I knew I wanted to frame the story around one specific human event as an introduction to this world. When Ross Ulbricht was arrested in 2013 it became very clear that was the way in.  You had two things: the Silk Road as the largest marketplace on the darknet, and I would argue the reason Bitcoin became so popular, and the arrest of this enigmatic young man, who we knew very little about.  This was all very interesting as it addressed several questions:  Was he “Dread Pirate Roberts?”; How do you charge somebody in federal court for a crime when everyone is anonymized?

WIRED reporter Andy Greenberg

WIRED reporter Andy Greenberg

I had followed Ross’s story when it happened and your documentary reminded me of a similar situation to Aaron Schwartz’ tragic death.  It seems like the government plan is to make an example out of someone, making more of a point with incarceration, to adopt future legislation or legal precedent.

As a documentary filmmaker, what are your impressions toward constructing a documentary narrative?  Did you want ‘Deep Web’ to be observational or activist in approach?
I come from a narrative background so I don’t look at storytelling as anything other than storytelling.  I am looking to tell the best, most impactful story possible.  I am definitely not looking to present a thesis. In fact, in terms of objectivity vs subjectivity, it is about creating a dialectic so that there are internal conflicts within the story itself since that is the human experience.  Personally, whether it’s fiction or not, I have an aversion to storytelling that is either hyper subjective or objective.  People need to take away from the story what they will take away.  This issue is provocative so it elicits strong reactions.  To my amusement, these strong reactions frequently fall into antithetical camps.

How did you adjust your approach as a Director from ‘Downloaded’ to ‘Deep Web’?
You evolve with every story, but there are alway little nuances you do as a storyteller from one story to another.  With ‘Downloaded,‘ given the fact it happened in the past, I surrounded myself with narrative people and talked about it from a narrative perspective.  This was a story that had already

Deep Web’ was a story that had already occurred, and in a very classical way so the approach was exactly the opposite. It happened in real time so we did not know what was going to happen.  For that reason, I built this film in a very different way. I surrounded myself with people more familiar with making documentaries.  People with the ability to tell stories on the fly.

Lyn Ulbricht, mother of Ross Ulbricht

Lyn Ulbricht, mother of Ross Ulbricht

There are a lot of interesting personalities in the film, was there a specific interview that was especially impactful to you?
These kinds of stories are always very impactful.  You go into them with a very open mind and you learn a lot.  Here, everyone in it was extraordinarily fascinating.  For example, the story of Ross’s mother, who had no technological background at all, suddenly is thrust in the center of one of our societies biggest moral and ethical debates, embracing the role of activist, as well as mother.

The open source programmers in the UK, who are doing extraordinary work with Bitcoin, are all very interesting people too.

Even the law enforcement was interesting.  This film was the kind where everyone blew your mind.  I was continually surprised and inspired by these people.

Have you encountered any pushback from government agencies as a result of the film?
No.  Since it was a federal trial a lot of them wouldn’t talk to me.  The people I spoke to were in the FBI and DHS. Within government though, many people are actually quite pro-privacy.  In this wide open internet where no one has the ability to protect their communication, they are as vulnerable to hackers as anyone else.

This film was not about one side vs another, it was about the whole situation.  The people I spoke to were very aware of that, as well as of the challenges.  When it comes to people who may be more aggressive against these issues they usually don’t go on the record because they think it will make them unpopular.

Finally, what is it about northern Europe that breeds such a high percentage of ideologically driven tech figures?  I ask because, as I am calling from Amsterdam, I find that I am constantly hearing about websites, communities or servers located in the region or in Scandinavia.  I wonder what is it about these countries that make them so prominent in these discussions?
I think its 100% ideological.  There is no legal haven there.  As we see in the film, there is no safety in having servers in Iceland or Germany, but you’re still dealing with a lot of the most advanced ideological thinkers and technologists coming from that part of the world.  Look at The Pirate Bay.  There is a lot of the nuanced discussion on the topic to be found in Europe.

– Interview conducted, transcribed and edited by Steve Rickinson

* ‘Deep Web’ will also have its broadcast premiere on May 31, 2015 on Epix (8pm EST)

Alex_WinterAbout The Filmmaker
Lifelong actor, producer and director, Alex Winter started as a child actor on Broadway and came to prominence in the wildly popular Bill and Ted franchise. Winter has directed two narrative features: cult classic Freaked for 20th Century Fox and Fever, which screened at Cannes. His TV credits range from MTV’s The Idiot Box to Emmy-nominated work for Cartoon Network, two Ben 10 films, as well as numerous music videos.

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