This year, Jack Dorsey emerged as the leading rep of bitcoin culture in Silicon Valley.

The Twitter co-founder and Square CEO is more relatable and trustworthy than Mark Zuckerberg and more rounded than Elon Musk, the weed-smoking mogul with a pop star girlfriend.

When asked if he would consider joining Facebook’s Libra Association, Dorsey replied: “Hell no.” Instead, he is betting on a different approach to mass technology: borderless and permissionless assets.

In March, Dorsey announced a new and separate entity, called Square Crypto, focused strictly on open source contributions to the bitcoin ecosystem. That team quickly snagged talent from Google, Facebook, Lightning Labs, and prolific Bitcoin Core developer Matt Corallo. No other company comparable with the FAANG gang has invested so much in contributing to bitcoin itself, rather than merely profiting from it.

“We do believe there’s opportunity to make banks a lot more accessible,” Dorsey said when I spoke to him on the phone in November. “If bitcoin delivers on its promise and its scale, then we maintain flexibility to utilize all of that [too]. That’s our intention.”

Dorsey’s commitment to bitcoin seems to be sincere. Bitcoin podcaster Matt Odell, who passed a small amount of bitcoin directly to Dorsey during the Lightning Torch experiment in February, said the maverick insisted on doing the transaction properly: that is, becoming a “full node” in a multistep process. This was the point of the “torch” and passing the same pot of digital gold around the world. Some more expedient participants were opting to use custodial wallets or direct channels for transactions. Not Dorsey.

“He runs a full node,” Odell said. “He said [the transaction] needed to be using a full node and I needed to be running a full node... I think it shows he’s here for the right reasons. And if later he turns on us, we’ll do the bitcoin thing and slay our heroes.”

This threat of public humiliation isn’t lost on Dorsey, who speaks cautiously and deliberately about bitcoin. During our interview, he repeated my questions several times and asked for clarity before answering.

He said he was attracted to the “philosophy” behind bitcoin and admired its creator for remaining pseudonymous. He sees bitcoin as a global and censorship resistant currency.

“It allows Square to act like a real internet [native] company, and launch services the whole world can use rather than going market to market, partnership to partnership, regulatory environment to regulatory environment,” he repeated, bored with these arbitrary borders applied to a virtual web. Along those lines, Dorsey has publicly stated he plans to spend more time in Africa next year, where he intends to meet with more bitcoiners.

“A global currency, of which bitcoin today is the best version, helps us move much faster. So we have every intention of helping it achieve currency status,” Dorsey said.

As Odell put it, Dorsey “puts his money where his mouth is,” in an effort to prove himself to the bitcoin community.

Square Crypto donated $100,000 to a payment processing project called BTCPay, which helps merchants run their own bitcoin full node, in September 2019. This might seem counterintuitive to anyone who views Square as a payments company. But Odell, whose podcast is partially sponsored by Square, said that Dorsey realizes BTCPay’s cypherpunk goals don’t compete with the heavily regulated fintech corporation. Instead, these interests run parallel.

“They’re each going to grow the pie and each benefit from it,” Odell said, referring to both Dorsey and the volunteers behind BTCPay. “We haven’t seen another [celebrity] CEO who really understands and tries to promote bitcoin adoption...There’s no one else really doing that.”

Bitcoin Lifestyle

Whether the motivation is profit or idealism, or potentially a combination of both, Dorsey positioned his businesses as pillars of the bitcoin ecosystem.

Twitter is the favored platform for networking and newsgathering among many bitcoin enthusiasts, while Square’s Cash App facilitated $148 million in bitcoin sales during the third quarter of 2019 alone. (Since Square reported $166 million in bitcoin sales in all of 2018, this year Cash App saw the type of growth that makes anyone with a Patagonia vest salivate.) But plenty of men have made more money, faster, in this space. That’s not what makes Dorsey so influential and worthy of praise.

He said Square Crypto would be tasked solely with improving and maintaining bitcoin as a public good.

Dorsey may be the poster boy for a “bitcoin lifestyle,” complete with arm tattoos, punk music, intermittent fasting, and a penchant of all-black ensembles. Yet he simultaneously contradicts the gun-toting libertarian carnivorous stereotype often (wrongly) associated with bitcoiners.

He personally donates to a variety of Democratic politicians, including Hawaiian congresswoman Tulsi Gabbard and rival presidential candidate Andrew Yang. Plus, Dorsey is an advisor to the Berggruen Institute, an independent think tank which develops ideas to shape political and social institutions. He almost focused on political science during his short stint in university and infamously told reporters he fantasized about becoming the mayor of New York. But he now knows he can influence the world more with his businesses than as a public servant. After all, his new dream is promoting global bitcoin adoption.

Dorsey is also a former Catholic school boy who modeled Georgio Armani pants and humble-brags about reading Shakespeare. Bitcoiners might be expected to loathe such trappings of the establishment, although no one ever questions this mogul’s cypherpunk street cred.

Perhaps this is partly because, in a space full of bombastic blowhards, the soft-spoken billionaire stands out as a man no longer consumed by a hunger for external validation.

He sits in an interview with one leg casually perched across his knee, yet his back is straight and his posture is turned toward the interviewer. He gestures subtly, politely, with his hands. His black hoodie and slacks are neat and clean, not slouchy hackathon garb.

What sets Dorsey apart as a bitcoiner in Silicon Valley is he exudes the ease of a novelist rather than a rock star, charisma that demands attention without veering into the performative.

This portrait was painted by Trevor Jones

“He has this zen nature about him,” Lightning Labs CEO Elizabeth Stark said. “He knows how to surround himself with super smart people and empower them, which I greatly admire. He's curious, eager to learn, and likes to ask for ideas and feedback.”

This is what makes him one of the most influential leaders in the bitcoin industry. Bitcoiners value signs of personal integrity and respect above other displays of masculinity.

None of this should be mistaken for humility. It may simply be a sign of maturity (at 42). He’s passed through darker times. More than a decade ago, Dorsey was involved in a highly political power struggle with three other Twitter co-founders before he eventually came out on top at CEO and allegedly portrayed himself as the company’s leading creator.

New York magazine summarized this “insufferable diva” period as a squabble punctuated by “girl chasing,” “wearing Dior, imitating Steve Jobs,” and gallivanting around the world. Dorsey may already be weary of the wealth and fame tempting some crypto moguls to embarass themselves in front of the integrity-focused bitcoin community.

“The bitcoin community, I’ve always found it to be very principled, weird, and noble,” Dorsey said.

Long before he became the bitcoin king of Silicon Valley, Dorsey had a classic cypherpunk backstory.

Early Days

Dorsey was born in Missouri with a speech impediment that underscored his natural introversion. He first fell in love with technology when he was eight years old, playing with an IBM PC Junior.

By his teenage years he was writing open source dispatching code, thanks to his fascination with city-mapping. He eventually dropped out of New York University and moved to San Francisco to chase his dream of working at a startup, refusing to take out his nose ring when employers scoffed. (He wore a bandaid over his nose instead.) He shares this trouble submitting to trivial authority dynamics (clinging to his right to wear a nose ring) with many bitcoiners of his ilk.

In 2000, he had the idea of mini live-blogging location updates, inspired by a combination of his dispatching experience and the blogging platform LiveJournal. But it wasn’t until 2005 that a chance meeting with seasoned entrepreneur (and future Twitter co-founder) Evan Williams would change Dorsey’s story from rebel-without-a-cause to maverick-computer-legend. Williams’ podcasting startup Odeo pivoted to become Twitter in 2006, with Dorsey helping spearhead the charge.

The following decade was a period of accelerated personal growth for Dorsey. Up until that point, his professional achievements had some precedent in his fascination with urbanization. His childhood bedroom walls were once plastered with maps. His shelves housed homemade videotapes of nearby rail yards. His prolific contributions to dispatching software led naturally to the world of microblogging.

Dorsey, who had been hired by Williams as a contractor, became Twitter CEO in 2007. He reportedly struggled to scale the company. “Servers were crashing every day,” Williams said. The two clashed over managerial priorities and, within two years, Dorsey was ostracized. He told Vanity Fair that being removed as CEO felt like “being punched in the stomach.”

Dethroned, he started to explore other interests. Dorsey founded the fintech startup Square in 2009, inspired by the idea of payments as another form of communication.

“I think Twitter is the future of communications,” he recalled in a 2011 interview, “and Square will be the payment network. We’re going big.”

This represented a dramatic shift in Dorsey’s aspirations, from focusing on the mechanics of technology to the broader networks and societies that produce them. Dorsey said he was a longtime follower of Usenet message boards and idolized the cypherpunks of decades past. He doesn’t remember precisely when he first got bitcoin, whether it was a gift or a purchase, but he said it was “pretty early” after the cryptocurrency launched in 2009.

(This interview marked the first time that someone told me they couldn’t describe their first experiences with bitcoin. That may be reflective of the tumultuous period it was in his life. Regardless, he kept that hobby relatively private until the short-lived Square Market experiment with bitcoin in 2014.)

When Dorsey returned to Twitter in 2011, he started splitting his time between Twitter and Square. Balancing both companies may have put a strain on his personal life, since his romantic relationship with ballerina Sofiane Sylve ended within a year of the move. By the time Twitter went public with a 2013 IPO, Dorsey’s stake in the company was worth $1.5 billion.

In 2015, Dorsey was once again crowned CEO of Twitter and had come to occupy the public persona he’s known for today: The man who sparked a techie trend by endorsing Silicon Valley Vipassanas. Adding even further to his wealth, Square’s Cash App started offering bitcoin purchases in late 2017, at the peak of the cryptocurrency boom.

Now both Dorsey and his customers are “stacking sats,” buying as much bitcoin as they can reasonably afford, then hodling.

“This stacking stats trend is pretty spot on. I tend to buy as much as I can on a regular basis,” Dorsey said, when asked if he still buys $10,000 worth of bitcoin a week.

Ambitious as always, Dorsey is set on helping bitcoin become a “truly global currency,” with an emphasis on currency.

Crypto Investor

In 2019, Dorsey founded Square Crypto, an independent entity within Square, and cemented his place as a leading investor in crypto companies as well.

Dorsey was one of the first investors in Lightning Labs in 2018, a startup focusing on layered scaling solutions for bitcoin. This company’s work is primarily open source, underscoring the same ethos espoused by Square Crypto. This year Dorsey publicly stated the Cash App team is exploring ways to leverage the lightning network.

Then in October, Dorsey contradicted the limitations of the ‘bitcoin maximalist’ stereotype by investing in CoinList, a startup focused on token sales that helped companies raise roughly $800 million worth of cryptocurrency since August 2017. CoinList co-founder Andy Bromberg describes Dorsey as a “tremendously helpful” investor with a proactive approach.

Dorsey said his own businesses would use the best technology available. Right now, he sees bitcoin as the leading contender. But he avoids being dogmatic about it.

“We don’t want to be adamant about any one solution in the space,” he said. “We want to make sure that we’re looking at the best, the most resilient, the most scalable, and the most successful [currency], ultimately.”

Finding a like-minded team of technologists was the most salient challenge of incorporating bitcoin into Dorsey’s strategy across businesses. Dorsey said the biggest mistake he made in his earlier days at Twitter and Square was underestimating the importance of building cooperative teams. (The Square Crypto team is now lead by Google alumni and longtime bitcoiner Steve Lee, an angel investor in Lyft and Pinterest.)

“Even if someone might be a superstar on their own...I try not to stay too focused on the individuals on the team but more on the dynamics between them,” Dorsey said.

Aside from comparisons to Zuckerberg and Musk, some in the cryptocurrency industry might notice key similarities and stark differences between Dorsey and the billionaire entrepreneur Joe Lubin, co-founder of ethereum and leader of the ConsenSys conglomerate.

Both Lubin and Dorsey are dedicated to spreading the global adoption of their favorite cryptocurrency projects. They’ve both invested in crypto companies, accumulated massive quantities of their respective digital assets and built horizontal pipelines for the network’s distribution. But 2019 was a parade of shuttering departments at ConsenSys, Lubin’s “blockchain studio,” while Dorsey’s companies focused on incorporating bitcoin, a public good created by a group outside himself, into a broader and quasi-traditional business model.

As Cash App engineer Miles Suter tweeted: “Companies that support and strengthen bitcoin now will know how to optimize their business models when there’s no other choice.”

Across several companies and cultures he’s helped create, Dorsey’s leadership experience taught him to innovate by incorporating user habits and feedback rather than tossing everything at the wall and seeing what sticks. This is why Dorsey won’t just be an influential bitcoiner in 2019. This year was merely the harbinger of Dorsey’s potential empire, fostered by a man who isn’t in a rush to build and learn as bitcoin grows up.

Dorsey’s initial growing pains as the head of Twitter taught him the importance of leading through example. He recently announced that Twitter will sponsor a team developing open source standards and resources for social media, akin to Square Crypto’s mandate. He also, famously, doesn’t receive any salary from his role at Twitter and is deliberately cautious not to promote a dream that blockchain technology will overtake all fiat currencies or institutional processes. He is demonstrating, through his companies, how to help lead a movement without monopolizing it.

“There’s going to be a series of services within [Cash App] that might replace why you go to a traditional bank,” Dorsey said. “But that doesn’t mean we won’t use traditional banks on the back-end. We should always maintain flexibility.”