GOOD HUMANS: Introducing Tom Preston-Werner, hacker (and lockpicker) emeritus

Colin Sullivan

July 15 2021

Tom is a youthful-looking Iowa native who shows up to Zoom meetings early. He’s likable, doesn’t get rattled and juggles a dozen projects at once. And he seems more interested in raising his kids and starting humane companies than, say, yachting off the Italian coast or buying overpriced sports teams.

It’s unlikely he’s ever owned leather pants, in other words. He’s not the sort that would bother to make those comparisons or see himself in another’s shadow, either. Much more likely is a discussion of open-source web development or carbon offsets or how to bring the best out of talented people than promotion of his own brand.

Tom also doesn’t seem to pay much attention to what other billionaires are up to, because he’s focused on his own companies and projects.

“I’ve always approached business by not caring what other people do,” he said recently in an interview. “Mostly what people have done before is terrible. That’s kind of why we are where we are, isn’t it?”

“I really like building, it’s really satisfying,” he added, from his home in Mendocino, Calif. “I’ve always been, and I think I will always be, about building products. I like learning new things.”

In some ways, Tom’s path has been the cliche tech-success story, the latest version of the American dream. He dropped out of college and moved to the Bay Area, where after selling a company called Gravatar he helped to launched GitHub, a darling tech outfit bought by Microsoft in 2018 — to the tune of $7.5 billion. He’s also thoughtful, down to Earth and unassuming. He’s always working, and most days he wears a worn black t-shirt to work. His is a quiet alpha presence that tends to mean he says weird things that also happen to make sense.

During a recent Preston-Werner Ventures (PWV) meeting about the organization’s performance in 2020, for instance, Tom was happy to field a question about the chosen logo for his new open-web development platform, RedwoodJS.

“It’s like a pine cone, but it’s a Redwood cone,” he deadpanned, to chuckles from others in the meeting, as he held up a small inch-long cone for all to see.

image Tom’s Redwood cone.

That metaphor — tiny seeds leading to massive root systems and giant trees — seems apt for Tom and his open-web ethic. His ideas for making products lean toward helping others to make cool stuff, and RedwoodJS is no exception. More than 200 individuals have contributed code to the project, and that fits with PWV’s “Hypothesis” mode of living and working, which states that there are certain things that ought to exist … so why not build them?

RedwoodJS, moreover, appears to be the latest in a line of ideas that could fundamentally change the way developers work, but you wouldn’t know it from asking Tom about it, who hesitates to assess how significant the product could be.

“It’s really about people and collaboration,” he said. “One of the more challenging things you can do is a web application framework. Will it be a company one day? Who knows. It’s too early to tell. For now, it’s an idea we wanted to exist.”

When pressed, Tom admitted “it could be a very big deal” for seasoned developers, but whether RedwoodJS attracts tons of attention before it’s complete seems to be pretty far down on his list of priorities.

“This is how it goes with products, you don’t know,” he said. “The scope of Redwood could be quite large. It’s almost a super framework. It could become a big deal, if it goes further.”

Breaking out of state parks

But success didn’t just appear overnight for Tom. David Price, a RedwoodJS developer who lives a few minutes away from the Preston-Werners in Mendocino, said Tom’s wealth shouldn’t fool anyone into believing he didn’t fail often. He explained that some of Tom’s best creations were given away for free, including Jekyll, which he made while working at GitHub. Jekyll converts plain text into low-powered websites and blogs.

“He’s built a lot of things that didn’t work out,” Price said. “I’m so sick and tired of those stories that say ‘so-and-so started a company at 21 and became a gazllionaire’. That almost never happens.”

Price said that most tech entrepreneurs who double as developers, like Tom, end up shutting down their favorite companies or selling them short to pay bills, or “getting out by the skin of your teeth” a few times before the big success lands — IF the big success ever lands, that is.

Still, Price lauded Tom for his “spectacular product sense” and called his ability to create a process for starting a company or launching a product his best talent. He pointed to a well-known 2010 blog post by Tom that urged creators to develop what is essentially a creative brief or treatment about a given idea before starting to code and build the project.

“Technical people have a tendency to start with the technical stuff,” he said. “Tom really understands design and how helpful a product is going to be. He has an innate ability to understand product solutions. He is exceptional at it.”

In that post, Tom urges programmers to “write your Readme first,” calling it an essential step in conceiving good software.

“A perfect implementation of the wrong specification is worthless,” he wrote. “By the same principle a beautifully crafted library with no documentation is also damn near worthless. If your software solves the wrong problem or nobody can figure out how to use it, there’s something very bad going on.”

image Tom’s vibe on Zoom.

Another developer who works with Tom, Rob Cameron, said the “good guy” image Tom projects isn’t necessarily the whole story. He and Tom rebuilt a 1979 Jeep in the same Southern California driveway where he used to host fish frys, for instance, and once “he broke us out of a state park after it closed at sunset with a lockpick he kept in his wallet,” Cameron said.

Asked if he still has the lockpick in his wallet, or whether he still picks locks, Tom said he doesn’t use a wallet anymore (“bare cash and cards in the pocket”) but he also offered this, via Slack:

“I do keep a set in my car. I started when I was a kid and made my first lockpick by grinding down an old steak knife. In high school, I ran the light board for school plays, and one rehearsal I was bored and tried to pick the lock on the light board controller. I succeeded and ended up turning all the lights off, and they had to stop their rehearsal until we could find someone with the key to turn it back on. Lol.”

That “Lol” having not been followed by a lockpick emoji. Does one exist in Slack? Maybe we should invent one.

The Hacker Zephyr: Here comes the coding train

Higher up on Tom’s list of stuff he likes to chat about is the language-learning app Chatterbug, where he was the chief product officer until recently, and how to get young people from all socio-economic backgrounds into the tech industry. Just as important is how Tom wants to spread his wealth around, having pledged to give away 10 percent through the Preston-Werner Foundation, which he co-founded with his wife, Theresa. And while he has his mind in a lot of pots, Tom’s pet project is Hack Club, a group that encourages teenagers to start their own coding clubs.

For his 42nd birthday last month, Tom purchased 42 cross-country train tickets for fledgling coders who will embark on “a trip of a lifetime” this week, according to Christina Asquith, the group’s chief operations officer, during which they’ll participate in “the world’s longest hackathon” aboard a train they’re calling the Hacker Zephyr.

The adventure starts in Burlington, Vt. Assembled hackers will chug south to New York, west through Chicago and stop briefly to pick up Tom this weekend in Iowa. They’ll then cross the Rockies on their way to San Francisco and follow the Pacific Coast to Southern California, to finish at SpaceX.

Asquith estimated the on-the-rails hackathon at 3,502 miles long. She credits Tom (along with another Hack Club believer, SpaceX founder Elon Musk) for his enthusiasm about the project, as well as the $750,000 the Preston-Werner Foundation has donated to the club.

“Tom is a GREAT guy,” wrote Asquith, in an email. “He’s seriously an awesome thinker, builder, connector, programmer, creator and feminist.”

Tom’s interest in Hack Club started when he met its founder, Zach Latta, when Latta was 19, and encouraged him to pursue his non-profit vision for helping high schoolers with the inclination to explore tech careers. Latta, who has won a Thiel Fellowship and was named to Forbes “30 under 30” list, says he wanted to create an organization that he wishes had existed when he was in high school — and Tom has always been onboard.

The 42 hackers have been challenged to make 500 contributions to a server Latta intends to bring on the train since it won’t have Internet. Called ZephyrNET, the used server was refurbished for the trip with 2 CPUs, 192 GB of RAM and 16 TB of storage.

“It's hosting an intranet over WiFi, and we've configured a custom DNS server and a deploy flow for both static and dynamic sites,” explained a Hack Club VIP briefing about preparations. “A handful of Hack Clubbers have already mirrored crates.io, npm and the Ubuntu Package Archive, along with adding offline copies of Stack Overflow and Wikipedia to it.”

As for the word “hacking” itself, Tom acknowledged it’s a point of confusion for those outside hacker culture. The word isn’t just for “bad guys hacking into banks,” he said. To him, hacking means hacking something together, “to bend the system but in a positive way.”

“Just play with stuff, just tinker, that’s what it means,” he said. “Hacking is like that. Taking the initiative to build something to do something. It’s the maker movement.”

As for hackers that have more aggressive (if not nefarious) notions of the calling, Tom admitted “we have to be more and more careful” as more infrastructure goes online, in reference to a recent ransomeware attack on the Colonial Pipeline in the United States. He promised that RedwoodJS, for one, will be as secure out of the box as possible and urged other developers to take security seriously.

“It’s really become obvious that you need to pay someone to try and break in,” he said, referring to security audits and penetration testing while noting that he’s made for-profit investments in companies focused on cybersecurity. “If you don’t do that, someone else will.”

On climate change and philanthropy

The core work of the charitable arm of PWV is not web development, however. The focus is climate change, and its difficult political reality, and by the way that’s demonstrably a much trickier problem than Tom or any other web guru is used to.

One of the ideas behind this newsletter is to connect the tech industry with activists trying their best to put a dent in the planet’s carbon emissions, to somehow draw that crowd and their talents to the cause. Tom wants to attract more developers, programmers, engineers and entrepreneurs to get into the mix on climate, because he believes his industry tackles complex challenges in a much different way than governments or policy experts — even if it’s a difficult marriage to pull off.

“We need more engineers and scientists in politics,” he said. “Engineers really don’t like the government process, because you can’t go solve your own problem. Maybe that needs to change.”

He’d also like to see the general population get angrier at the corporations that are largely responsible for emissions and slowing the process towards addressing them. If there was ever a hint of outrage during our interviews, it was about the sorts of untruths and distortions that have led low-income humans into disbelieving core issues they associate with progressive (and often privileged) liberals, whether that’s systemic racism or the warming planet.

“Part of the right-wing approach is to pit the low-income person against the other low-income person, telling them it’s the immigrant that’s going to steal your job,” he said. “But is that really the problem? Part of this is to get some truth into people minds about where culpability is.”

It’s that search for political truth that has become a kind of mid-career segue for Tom, leading to the creation of a family foundation over the last few years. A nimble organization that’s still finding its way, Tom defers to his wife, Theresa, calling her “the real brains behind the operation.” Theirs is a partnership launched in the same “Hypothesis” mode, because that’s truly how “TnT” (as they sometimes refer to themselves) like to operate. It’s part marriage, part business partnership, part constant brainstorm, and he credits Theresa — an anthropologist by training and a natural connector — with complementing what he refers to as his “operational” strengths.

“I’ve always been a better operator than a strategist,” he said. “I think the two of us together are really effective.”

Tom also credits the ethic at GitHub, which he founded with three others, for creating the framework that feeds their “TnT superhero duo”. He believes their dynamic is possible anytime two smart brains are directed to work side by side, feeding off each other.

“We did it purposefully,” he said. “We would try to find two people at GitHub, and each person would try to impress the other. We found that good things can happen when just two people explore a larger scope.”

“You might end up in a bubble if you’re too much the same,” he added.

That’s also part of why TnT wanted to launch this newsletter, because the Preston-Werners suspect communication is another way to improve their climate hack — to tinker with the subject in a more transparent manner that might draw others to the urgent need to collaborate and amp up political pressure. Tom hopes that doing so will support a broader effort that isn’t about self-promotion of his brand or the TnT way so much as the creation of a a movement in politics that might better resemble the open source paradigm in tech.

Or as Theresa put it, perhaps more candidly, when asked about why Tom was so invested in the cause: “He’s not necessarily driven by trying to do good in the world. He’s curious about trying to solve the problem.”

Here’s hoping that curiosity draws in more brains like Tom and Theresa’s.

Next week: More on Hack Club’s hackathon from the railroad and a deep dive into “theory of change”. Stay tuned for much more on the excellent humans behind PWV, our grantees and our community in the weeks and months ahead. Feedback always welcome! This newsletter is a new venture. Get in touch anytime.

— by Colin Sullivan

Sullivan is the former West Coast bureau chief and congressional editor for E&ENews. He’s based in Washington, D.C.