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Meet the 2015 SXSW Filmmakers #19: Alex Winter Explores the Internet’s Black Market in ‘Deep Web’

Meet the 2015 SXSW Filmmakers #19: Alex Winter Explores the Internet's Black Market in 'Deep Web'

Deep Web” (Alex Winter’s third effort as a writer-director) gives viewers an exclusive, inside look at The Dread Pirate Roberts (no, not that one — his real name is Ross William Ulbricht), the man behind the billion-dollar online market, The Silk Road. Through interviews with the man himself as well as his family, Winter takes a look at what things like the Deep Web and Bitcoin mean for the future of our digital rights. “Deep Web” will premiere on EPIX on Sunday, May 31 at 8pm.

What’s your film about in 140 characters or less?

The rise and fall of the Silk Road online black market, and the arrest and trial of Ross Ulbricht; accused of being the mastermind Dread Pirate Roberts.

Now what’s it REALLY about?

The film examines the socio-political digital movement that ultimately gave birth to unregulated, anonymous markets like Silk Road. This movement began with the origins of the Internet and threads through the Cypherpunks, Wikileaks, Crypto-anarchists and then Bitcoin and the black markets. Today, the movement is most active in a hidden area of the Internet known as the Dark Net. And while encryption and the dark net are routinely portrayed as nefarious, the truth is that they are largely used for good. The fight to curtail these tools, by government and law enforcement, puts not only the good actors of this movement at risk, but also threatens the rights to privacy online for all citizens.

Tell us briefly about yourself.

I am a filmmaker, writer and actor. For over twenty-five years I’ve been directing movies (Freaked, Fever), documentaries (Downloaded, Deep Web) and many many commercials, music videos and TV shows. I began in the industry as a child actor with starring roles on Broadway in King & I and Peter Pan. And also starred in a few movies such as the Lost Boys and the Bill & Ted Franchise.

Biggest challenge in completing this film?

Gaining the trust of the core architects and vendors of the Silk Road, the other main players in this movement and the Ulbricht family and defense team, and Ross Ulbricht himself. I have a long history of involvement with cryptography and Internet privacy, beginning with the BBS/Usenet era of the late 80’s. Spending over a dozen years on the Napster movie Downloaded introduced me to more of the key participants in this world which helped me here. Interviewing cyber-criminals, some of whom are still at large, also posed a great challenge.

What do you want SXSW audience to take away from your film?

I hope that they learn about a vast area of the Internet that exists alongside the visible net. And why this technology is primarily a good thing that should not be demonized and criminalized. I also am eager for people to be exposed to the plight of Ross Ulbricht, who faces life in prison, and decide for themselves whether he is in fact guilty or not of what he is being charged with. There are many important shades of gray in this story, with issues at play that will impact everyone, not just people who use encryption and the dark net. And all we have seen in the media so far is a black and white portrayal that is lacking in the grays and often erroneously reporting the facts.

Any films inspire you?

Too many! For this film specifically I was drawn to the simple, humanist work of Frederick Wiseman, Barbara Kopple, The Maysles brothers and Laura Poitras on the doc side. And Sidney Lumet, Costa-Gavras and Olivier Assayas on the narrative. Poitras’s “Citizen Four” and Assayas’s “Carlos” are two of the strongest and most perfect political dramas I’ve ever seen. Certainly the best of the century so far in my book.

What’s next?

I am co-writing two hour-long cable TV projects. Both dramas with factual/historical origins. Similar in tone to Downloaded and Deep Web, but narrative. And I’m developing two new documentary projects, one of which I will shoot next.

What cameras did you shoot on?

Alexa primarily. And Canon 5D, C300 and C100.

Did you crowdfund? If so, via what platform. If not, why?

Yes we certainly did. Marc Schiller (who is a guru in this world), actually cooked up the original idea for this movie. He and I worked together on Downloaded and built a big online community with that film. Together with our other producer Glen Zipper we mounted a Kickstarter campain for “Deep Web,” not asking for much. We funded and used that money to make a teaser which then secured the bulk of our funding. But as importantly we had created a very large online community for the film, before we even shot a frame.

Did you go to film school? If so, which one?

NYU Tisch School of the Arts. Undergrad. A hundred years ago and it’s still great.

Indiewire invited SXSW Film Festival directors to tell us about their films, including what inspired them, the challenges they faced and what they’re doing next. For profiles go HERE.

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