Alex Winter made his name as a film star—most famously as lovable doofus William “Bill” S. Preston, Esq. in 1989’s Bill & Ted’s Excellent Adventure and its 1991 sequel—but in recent years he’s become known for his decidedly non-bogus documentary work. In 2013, Winter released Downloaded, about the revolutionary music file-sharing service Napster, and two years later he put out Deep Web, focusing on the case of Ross Ulbricht, who ran the infamous dark web market the Silk Road. Now he’s back with Trust Machine: The Story of Blockchain, which feels like the third part of a tech trilogy.
“The formula I use for any of these documentaries about technology is always to focus on individuals,” Winter says. “I have literally no interest in trying to make a movie that will say, ‘Here’s an eight-minute infographic that’s going to walk you through how decentralized ledgers work.’ That’s what Google is for. Artistically, that would be a really horrible thing to do. If you tell an interesting story with interesting people, you’re not going to lose anybody.” Among the interesting people Winter talks to in the film are venture capitalist Tim Draper, industry luminary Vinay Gupta, tech-savvy musician Imogen Heap, Ethereum cofounder Joseph Lubin, hacker and activist Lauri Love, and blockchain journalist Laura Shin.
By turns serious and laugh-out-loud funny, Trust Machine, produced by SingularDTV (BREAKER’s parent company) and Futurism, opens in New York this Friday and in Los Angeles November 16. The film will become available on SingularDTV’s distribution platform next year. BREAKER recently spoke to Winter, 53, about the blockchain space’s visionaries, troublemakers, skeptics, and scammers—and what’s going on with the third Bill & Ted movie.
Related: TaTaTu Taps Johnny Depp to Collaborate on Films
Blockchain is an incredibly complicated subject. What gave you the nerve to make a documentary about it?
The last two docs before this were both about emerging technologies and global communities. I’ve been very familiar and close with a lot of the fundamental people in internet technology since the late ‘80s. So it’s a world I know very well.
Did it take any getting up to speed on blockchain before you started the film?
No. I’d been watching blockchain grow since I read the white paper years ago, so I’m well aware.
So you’re an OG then?
As much as there can be an OG in the bitcoin space, I am, yeah.
Do you personally own cryptocurrency?
There was a period where I had a fair amount of bitcoin, but to be honest with you, when Trump won I donated all of it to the ACLU and Freedom of the Press Foundation to fight the good fight. But I’m not a speculator. The cryptocurrencies that I own, I own primarily to keep an eye on the marketplace and also to stay familiar with the various wallets and keep abreast of the technologies and how they’re evolving.
Why not make a documentary focusing on cryptocurrencies like bitcoin and Ethereum? That’s the stuff that seems to capture the public’s imagination.
I really had no interest in that. When I made the Silk Road doc, I started off making it much more about bitcoin, and I interviewed most of the major players in that space, like Gavin Andresen and the folks at Coinbase. We traveled all over the world and have a lot of footage of all them, and we put a lot of it out. But I wasn’t that interested in bitcoin as a movie. I enjoy following it. I enjoy reading magazine articles about it. But it felt a bit more newsy than it did cinematic.
This movie was exciting to me because it could track both the potential for blockchain as well as this crazy moment we’re in, of complete hysteria and evangelism and speculation—which I knew was gonna pop. I always saw bitcoin/blockchain mania as really similar to the first internet bubble of the late ‘90s that completely exploded. It didn’t mean there was no more internet. Of course, the internet actually became fundamental to everyone’s lives.
In the film, you focus on Lauri Love, a British hacker and activist accused of stealing data from U.S. government computers. What drew you to his case?
That’s actually not what he was accused of—I don’t know where that’s been coming from. Lauri was accused of defacing government property. There was an Anonymous op that was protesting Aaron Schwarz’s suicide. He wasn’t actually ever charged with anything because the case got thrown out of the U.S. criminal justice system. It remains to be seen whether he gets brought to trial in the U.K., but it’s not looking very likely.
Lauri is a computer scientist who’s been doing a lot of work in the blockchain space from the very beginning and has been a big part of the bitcoin community. [His story] represented the fight by governments who are very threatened by these emerging technologies and tend to find scapegoats. I really wanted to get into explaining that because we’d already lost Aaron Schwarz because of an egregious attempted prosecution. Thankfully the film has—not to spoil it for people reading this—a relatively happy ending, in that the British government rejected the U.S.’s attempt to extradite Lauri, which is pretty unheard of.
Hacker and activist Lauri Love (center, in hat) in a scene from Trust Machine.

Each of your three tech documentaries have focused on an outsider like Love. In Downloaded it was Napster creator Shawn Fanning; in Deep Web it was Silk Road proprietor Ross Ulbricht. How in your mind are these three similar and how are they different?
They’re pretty different. But I’d say that what was similar about all three of them is that they all were penalized for being ahead of their time. And to be really clear, that’s not to exonerate any of the ethical issues around what any of those people have done. In fact, it’s their duality and their complexity that’s most intriguing to me.
Fanning’s lightbulb moment was envisioning a global internet-based community where you would have an enormous amount of people on a single system at once, which had never happened. Ross, his lightbulb moment was connecting bitcoin to Tor and thus creating what I would call the first largescale anonymous global internet community.
I look at Lauri Love and—I doubt he would define himself this way—but to me he’s a really good example of a modern-day cypherpunk. Lauri to me represents the political idealism of bitcoin and cryptocurrencies, Satoshi’s original vision, and we’re seeing how people like Lauri are being penalized and attacked because they’re threatening to a lot of people.
Do you think your film will change people’s minds about cryptocurrency, which is widely associated with buying drugs on the dark web?
It never crossed my mind to try to do that. It’s funny, because I felt like Deep Web did a good job of showing that cryptocurrencies are actually terrible for buying drugs, because it’s the least anonymous currency that exists. A digital ledger is verifiable identity, right? So if you’re tagged on the other end of end-to-end encryption, that’s rock-solid proof that you spend X amount of bitcoin on whatever you were purchasing. When I was doing the festival circuit with Deep Web, a lot of people were like, “Oh my god, I’m so happy I saw this movie because I realized the last thing I want to use these cryptocurrencies for is anything illegal.”
There are elements of both Downloaded and Deep Web in Trust Machine, which makes it feel like a trilogy. Is that the way you looked at it?
When I was three-quarters the way through [working on Trust Machine], I felt, This is kind of the third part of one continuing conversation. Deep Web and Downloaded are connected, but I when I was making them, I wasn’t thinking of it that way, like, “Oh, here’s my companion piece to Downloaded.” But they tell a story of a very particular moment in time in the nascent days of the information age where there’s a lot of potential, there’s a lot of mistakes being made, there’s some flat-out ethical and criminal activity happening, and there’s a lot of threats to institutions and governments.
Will you ever make a fourth part?
I don’t know. It’s possible. The fourth piece I’d love to do is almost like a check-in, in 10 years. There’s a lot of people saying what blockchain is going to impact and what changes it’s going to make. There’s a lot of naysayers saying it’s just complete nonsense and it’s all going to go away and there’s no need for verified ledgers and that it’s a solution in search of a problem. I’m really curious to see which of those pans out. My guess is it’ll be neither. It will be some version of both.
For Trust Machine, did you try to interview any skeptics, like JPMorgan Chase CEO Jamie Dimon, who once called bitcoin “a fraud”?
The skeptics never want to talk because they know you’re going to make them look like an ass. [Napster foe] Lars [Ulrich of Metallica] didn’t want to talk to me for Downloaded. I met with him for like an hour to talk about what I was doing, and in the end, he was just like, “You know, I love you. But [if I were to be] in this movie, I’m going to be the asshole who’s saying no to everything.”
"[Skeptics are] fairly aware that they could end up being in the trailer looking like kind of a jerk, and nobody wants to look like a jerk."
Did you even bother approaching the skeptics for Trust Machine?
Yeah, we approached everybody. We always do. We go, “We’ll be nice.” You know, “This is what we’re doing. It’s not a puff piece for blockchain.” But I think they’re fairly aware that they could end up being in the trailer looking like kind of a jerk, and nobody wants to look like a jerk. I wasn’t worried about it, because there was so much archival footage of those people stating their piece that I felt we were well-covered. We do have people like Matt Green, who’s a highly respected computer scientist and tech expert who teaches at Johns Hopkins. Matt is a very well-known skeptic. He’s not completely a naysayer, but he does believe that there’s a lot of B.S. in this space and a lot of it’s just going to disappear.
There are some many scammers in the space. How did you vet people before you interviewed them?
We interviewed some scammers. I was interested in talking to everybody. I was also interested in telling the story of decentralization. So a lot of the individual companies I talked to I felt had a clear-cut view of decentralization, whether it was about identity, whether it was about refugees, whether it was about energy, whether it was about mesh networks and circumventing the telecoms. These were the people I thought would help an audience go, “Oh, I see. This is what the general thrust of this movement is about.” Vetting people is not hard. I have lawyers and researchers and archivists, and it’s pretty easy to dig into what someone’s doing and see what its authenticity is.
You said you interviewed scammers. I don’t recall seeing any outright scammers in the film.
Right, well… Not gonna answer that. [Laughs.] One person’s scammer is another person’s hero.
When I saw a screening of the film, there were a fair amount of laughs coming from the audience. What parts stand out as funny to you?
To me, these movies always have to be funny. I mean even Deep Web was funny in parts, despite the gravity of what was happening to Ross. To me, this movie is almost a flat-out comedy. Not in a way where we’re making fun of people—because that’s not what I find funny anyway—but there’s something really funny about watching the exuberance of a world that’s hellbent on something that they largely don’t understand or does not even necessarily exist yet.
What parts are getting the most laughs at screenings that you’ve been to so far?
The laughs are throughout. We’re seeing how people reacted to Jeff Bezos. Like they just dismissed him as a fly-by-night weirdo. That gets a lot of laughs. Then all of the news anchors trying to wrap their head around blockchain or being outwardly and snidely dismissive of it. That gets a lot of laughs. And then the crazy kind of bitcoin people always get a lot of laughs. [Narrator] Rosario [Dawson] is witty, so she knew how to work with the dialogue to give it that lightness.
Your next two documentaries tackle very different subjects: Frank Zappa and the Panama Papers. What can we expect from them?
The Panama Papers will be out wide before Trust Machine is out wide. It’s about what I consider to be the gravest issue facing us today as a global civilization, which is income inequality. It’s a kind of a double story. On the macro side, it’s a story about how our economy is essentially a custom-built system to keep the middle class and the poor under the bootheel of the one percent—and that’s not an accident, it’s been constructed as an economic system. And then on the micro, it’s a story about the largest coordinated act of journalism in history. You had hundreds and hundreds of journalists working in total secrecy around the world to break the story, and that’s never, ever happened before, so that was really intriguing to me.
And Frank Zappa: I’m a huge Zappa fan, but I tend to make movies about, if not political issues, certainly social issues, and Zappa, as well as being a great artist, he was very connected to the time that he lived in. He fought the Senate over censorship, and he helped Václav Havel bring Czechoslovakia into its new era. Zappa did a lot of incredible things in the political and social space. He was also very polarizing, and I like polarizing subjects.
And there’s also a fair amount of Zappa family drama going on. Do you get into that in the film?
No, my film is about Frank Zappa, who died 25 years ago. It’s not about family drama that’s happening 25 years later. I’m telling what I think is the first really fun biographical story of Frank. It doesn’t get into present-day skirmishes.
"I want people to experience what it’s like to be caught up in the eye of the crypto and blockchain hurricane."
What do you hope audiences will take away from Trust Machine, especially those uninitiated with blockchain?
I hope first and foremost that people have an enriching and entertaining movie experience. That’s my job. I don’t really make issues or lessons movies. I want people to experience what it’s like to be caught up in the eye of the crypto and blockchain hurricane. This mad moment that a lot of people feel on the outside of, I want them to feel what it’s like to be whipped up on the inside of that. And frankly, that doesn’t require being an expert in blockchain. Because honestly, I can tell you, 99.9 percent of the people I know in that community have no idea how the technology of blockchain actually works.
Do any of the projects that you cover in the film stand out as favorites?
I really love what UNICEF is doing. The ability of a refugee to come out of a war-torn country—let’s say someone’s coming out of Syria and they have no kind of passport, no kind of ID—and to have a verifiable ledger of those people and give them a way to start to rebuild in a global society is really amazing.
The naysayers will say, “A verifiable ledger can be used for evil as well as for good.” My argument with that is that ship has sailed. Let’s wake up. That’s Equifax, that’s Anthem, that’s the Target hack. We live in a world where identity is already being traded as contraband and is already being violated and exposed. The verifiable ledger falling into the wrong hands is not the thing I’m worried about because that’s the world we’ve lived in already for a long time.
Is there anything, in terms of the blockchain, that keeps you up at night?
The things that keep me up at night are not blockchain-related at all. The fact that everybody’s [operations security], including governments’ and military installations’ is terrible keeps me up at night. The fact that our power grids are so easily hackable. The fact that all of our data is already completely out there for anybody to sell or use however they want. The current system is sort of like what they’re saying about New York subway: It’s Byzantine, it’s broken, it’s unsafe, and it needs to be completely dismantled and rebuilt with a more effective, efficient system. So the current system keeps me up at night. I’m really hopeful for something better coming along.
I have to ask: Word is there’s a Bill & Ted three happening. Where are you in the process, and what can we expect?
We are in what’s called pre-prep, which is pre-preproduction, meaning the writers are doing a production polish. We’ve done budgets, we’ve put crews together, we are looking at locations, and right now we’re on track to shoot next year. Look, it’s Hollywood, anything can happen. But everybody’s working very hard at the moment, so that’s a good thing.
Is there anything you need to do to switch from being a director to getting into the mindset of Bill?
Not really. It doesn’t require an enormous amount of gear-switching. I started acting when I was very young and I have a lot of experience, so it’s not something that you lose, but I have continued training over the years because I like it. Acting is fun, I just don’t like doing it professionally over my [directorial] work. I’m not rusty, but it doesn’t take an enormous amount. You know, I’m not doing Hamlet. [Laughs.] Then I would be nervous.
This interview has been edited and condensed. Images courtesy SingularDTV.