The unauthorized profile of Chris Dixon, the world’s top crypto investor

Desperate for guidance on how to build video games, the tech-obsessed preteen would persuade his parents each month to drive him down to the local air base, Wright-Patterson, about a 35-minute drive from the 1920s three-bedroom home where he grew up, in the small town of Springfield, Ohio. A group of engineers there who shared his affinity for computers hosted one of the state’s many monthly Atari “user group” meetings for other computer enthusiasts. 

But Dixon was more than just a casual enthusiast. Thwarted by the lack of technical information available to him, young Dixon penned a letter to Atari, asking if the company could send him some user manuals. Alan Kay, chief scientist at Atari, and an award-winning computer programmer, personally wrote him a letter back and shipped him a box of guides.

“I give him a lot of credit for my lifelong interest in computers,” Dixon would write in a blog post in 2009. Those were the roots of Dixon’s programming knowledge that would serve as the gateway to his career as a developer, a tech founder, an eBay manager, and later—his efforts to back and build the next iteration of the internet as the world’s most well-funded crypto VC.

Dixon, now 50 years old, oversees venture capital powerhouse Andreessen Horowitz’s crypto vertical—a purview that includes cryptocurrency exchanges, NFT projects, and decentralized finance apps. PitchBook pegs Andreessen as managing $6.3 billion in funds focused on digital asset investments, though that includes a $3.2 billion fund that holds non-crypto assets (Andreessen says it oversees about $3.1 billion among its crypto funds). The closest runner-up is Paradigm, which oversees a $2.5 billion crypto fund (Paradigm oversees $13 billion in assets, per its latest filings, but its other funds are not traditional VC vehicles). No investor has more venture capital money—nor such a large support team—to wield in the digital asset arena than Andreessen Horowitz, and Dixon is considered by many to be the most important dealmaker and one of the earliest backers in the nascent space.

But while he signs some of the largest checks in the hottest corner of the tech and investing world, Dixon is relatively unknown. Fortune reached out to more than 50 individuals for this story—people who have known him personally and professionally, worked for him, with him, above him, or alongside him—many of whom declined to participate on the premise that, while they knew of him, they really didn’t know anything about him. (Dixon declined to comment for this story on multiple occasions.)

Dixon is known to be a private person, and what makes its way to the public has largely been on his own terms—via the personal website he’s maintained since 2007, or his Twitter account that dates back to 2008, when he was a young CEO in New York City’s burgeoning tech scene. Since founding his second company, Dixon has preferred to remain in the background, ceding the spotlight to more forward-facing, attention-grabbing copartners, only emerging to talk about crypto, venture capital, and tech when and where he sees fit.

Dixon is alternately described as driven, nerdy, innovative, and prescient, but also enigmatic—qualities somewhat reminiscent of crypto, the field where he has made his name and much of his recent fortune. The decisions he’s making now will help shape what the future of Web3 holds—which companies ultimately end up being its most important players, and what role that crypto plays in all our lives going forward. Dixon could likely end up renowned like some of his (at times controversial) predecessors: Arthur Rock, who shaped the origins of Silicon Valley; Eugene Kleiner and Don Valentine, who would define the dotcom boom; and Peter Thiel and Bill Gurley, who were the first to back some of the companies that now make up Big Tech. Alternatively, hindsight might make Dixon out to be a gambler—a promising investor who, once he went down the rabbit hole, put one too many eggs in the same basket.

Angels in Silicon Alley

Dixon wasn’t born a New Yorker, but he became one. 

One way to trace his path through the city is, as it is for many Big Apple denizens, through the food.

There’s a small takeout window that serves bone broth under an orange canopy at the corner of 12th Street and First Avenue. Or you might have spotted him at Eisenberg’s Sandwich Shop before it closed during the pandemic, a 91-year-old New York institution recognizable by a simple photo of one of its duct-taped barstools, where Dixon would order the BLT. Then there is Mandoo Bar in Koreatown on 32nd Street, where Dixon likes bibimbap with an egg.

His reverence for New York food, cultivated while he was an undergraduate philosophy student at Columbia University, would later populate his Foursquare and Instagram accounts—both companies Andreessen has invested in. (Dixon’s COVID-era Instant Pot cooking has also made appearances.)

Dixon has three degrees: a philosophy undergraduate degree from Columbia, a master’s from its Graduate School of Arts and Sciences, and an MBA from Harvard University, where he would meet his first wife. His passion for academia shouldn’t come as a surprise: Dixon is one of four sons of two retired English department professors at Wittenberg University, a liberal arts college in Springfield.

His background in philosophy, logic, and syllogisms has resurfaced in his writing and even in his investments. One of the founders Dixon funded as an angel investor recalled him mentioning he had studied philosophy in their first conversation.

Dixon was a self-taught programmer from a young age since his time sitting in on the user clubs at Wright-Patterson. After college, he built algorithms for a high-frequency trading firm on Wall Street, Arbitrade (it eventually rolled into Citigroup after multiple acquisitions). But he didn’t see the value in finance. He had stints at other companies, as well, like Oddcast, a media technology company, where he developed its talking avatar software. His first foray into venture was as an associate at Bessemer Venture Partners, where he worked under general partners Jeremy Levine and Rob Stavis. He worked on Bessemer’s Skype investment during his time there.

“It wasn’t the sort of job I enjoy,” Dixon would later say in 2010 about his time at Bessemer, noting that he didn’t foresee himself ever working in the industry again full-time, and thought of himself more as an entrepreneur than an investor. 

Four people who knew Dixon in those years describe him as exceedingly smart and say he had a lot of ideas. As an MBA student at Harvard, he built an experimental tracking product called DidTheyReadIt with colleague Alex Rampell (who also went on to become an a16z GP), where he embedded pixels within emails that would report back the time a message was read.

“He is very adept at synthesizing information, taking risk, and learning at an amazingly accelerated level,” said Daniel Jeffries, who worked with Dixon at Oddcast but is no longer in touch. “I never met a more innovative programmer, and it wasn’t even his full-time job, just something he learned because he was interested and nobody else could do what he wanted done.” 

During his time at Bessemer, Dixon launched his first company, the security website SiteAdvisor, which was incubated at the venture capital firm. The company was an effort to prove to Bessemer he could start and run his own business, Jeffries recalled Dixon telling him, according to a blog post he wrote about Dixon in 2017. Dixon sold it within a year of its launch to computer security software company McAfee, when its product had only been out for about four months.

In 2008, Dixon bought his first property in the Big Apple with his first wife in Park Slope, Brooklyn, for nearly $3.8 million. And he had the cash to start making his own investments. Dixon called up Ron Conway, whose firm SV Angel had been a seed investor in SiteAdvisor, and who had become a friend, to ask how to get on the cap table as a solo investor.

Shortly thereafter, Dixon took a flight out to California to persuade Aaron Patzer, founder of Mint.com, to hear his pitch and offer Patzer money. But he quickly got a no. Dixon’s last company had nothing to do with the consumer internet or finance. First Round Capital, Felicis Ventures, Conway, and Yahoo’s Geoff Ralston were already on the cap table. 

That no was a light bulb moment for Dixon, who would later say he realized that investors had to offer founders more than just capital—they needed a track record of being useful. (For Patzer’s part, he says he had received 50 no’s before First Round Capital agreed to invest. “Once they said yes, the round was oversubscribed in a few weeks,” he said in an email, not responding to a request for further comment. “If Chris had contacted me a month earlier, I’m sure I would have said yes.”)

But Dixon took that no to heart, making it a point to show up for founders of companies he invested in, of which there would be many—including Kickstarter, Pinterest, Codecademy, Stack Overflow, Bloomreach, Optimizely, and OMGPOP. “He has good frameworks,” says one founder, who asked not to be identified. Dixon helped brainstorm how to find traffic and build the company’s presence on the web. He would always get back to staff quickly whenever they asked for anything, the founder says.

Dixon has a Hunch

In the late 2000s, New York’s startup scene was small. Etsy, Buzzfeed, and Bloomberg were some of the tech company headliners popping up at the time. Many of those tech offices were in Chelsea, in what became known as Silicon Alley. Tech entrepreneurs and investors tended to run in various circles that weren’t necessarily connected. Yet there was a core group of individuals who had a presence online, and people would gather at tech Meetup events, says a venture colleague in the New York startup scene, who asked not to be identified. 

“Chris was definitely somebody who went to all the things,” the colleague said.

Dixon was well-known for what was, at the time, considered to be a rather robust online presence. He had been writing a tech blog on his website since 2009, and he was—somewhat ironically, given his very-public spat with Jack Dorsey over the value of Web3 and Andreessen’s investment in Twitter—one of the early users of the platform, signing up for it in 2007. (Dixon has been using the same avatar on Twitter, and later his blog, for more than a dozen years, although there was a brief point in time when he swapped it out for a similar-looking cartoon with a mullet.)

“At that time, you got some wind at your back for doing that,” the venture colleague says of Dixon’s public blog.

He also regularly leveraged the press—back when it was useful for him to do so and he could use it to his own advantage. SiteAdvisor, despite only being in business for less than a year, had a media relations person and blogger, and it posted a list of more than 30 articles or websites it was featured in prior to McAfee acquiring it. “We performed studies on data we had collected, which led to lots of coverage, which raised our profile and bolstered our credibility,” Dixon wrote about his press strategy on his blog in 2009. 

In 2009, Dixon started Hunch with Caterina Fake, who had cofounded Flickr (with her then-husband Stewart Butterfield, and sold it to Yahoo a few years later), and two others. By that time, both Fake and Dixon had made names for themselves having made multimillion exits in New York.

“By startup number two, we were clamoring to invest with Chris again,” says Conway, the investor in SiteAdvisor and friend of Dixon’s. He adds: “We were totally in love with Chris. We knew that he was one of the smartest founders that we would ever meet. He was down-to-earth and didn’t exaggerate. What you see is what you get.”

Hunch, which made book, movie, product, or hobby recommendations when you answered questions about yourself (such as whether or not you dance), immediately made a splash at launch. Fake had a more boisterous personality and Flickr a bigger following, and Dixon appears to have largely let her take center stage. 

“This is not somebody who yells from the mountaintops,” Conway says of Dixon, describing him as unpretentious, humble, and quiet. “He’s steady. He’s steady, and he likes being in the background. He doesn’t like being in the foreground.”

Dixon and Fake both were also founder-partners of a venture capital fund started by angel entrepreneurs called Founder Collective, intended to invest in seed rounds only and pursue burgeoning opportunities in New York. At Hunch, Dixon and Fake brought on several of SiteAdvisor’s old team members, and put together a company in an office space behind a maroon door in an 11-story cream-colored building on 21st Street in the Flatiron District. The office was casual and friendly, recalls one founder who came into Hunch to pitch Dixon. A schnauzer named Nanu roamed the office.

At some point, Dixon and Fake began a brief relationship, says a person familiar with the matter, who asked not to be identified. Fake—who had divorced Flickr’s other founder, Stewart Butterfield, in 2008 (he went on to found company messaging platform Slack), according to records—suddenly left Hunch at the end of 2010. Dixon and his first wife had separated in 2009, then were formally divorced in 2011. (Dixon’s first wife and Fake didn’t respond to requests for comment.)

Fake’s departure aside, a profitable exit would still be in store: eBay purchased Hunch for $80 million in 2011, with the hand of Conway, who says he helped engineer the terms of the sale with eBay’s then-CEO John Donahoe. Dixon stayed on to run the New York team and build out the company’s East Coast office—which included orchestrating a six-person secret trip to Australia to rebrand the company’s digital presence and turn it around, though he wouldn’t attend himself.

But corporate life did not last long for Dixon. By the end of 2012, conversations had been underway for some time, and Dixon was on his way to Andreessen—and to the West Coast.

New chapter, same avatar

Heading West was a radical shift for Dixon, who had spent the past five years touting the growth and potential of New York’s tech scene. He had become one of the noisiest, most public critics of billion-dollar funds and mega-firms. And now he was going to join one of the biggest funds in the industry. Marc Andreessen and Ben Horowitz’s venture capital firm, which was founded in 2009, had scaled into a $2.7 billion fund with six general partners. 

“What I was critical of was…Just a lot of the practices that evolved in the business for a long time,” Dixon said on camera of the VC industry in 2013, shortly after his move to Andreessen. “Basically it was a business that was dominated [by] a few firms. There was this expectation that all entrepreneurs had to go through and pitch those firms, and there was a scarcity of capital. And I think as a result, a little bit of arrogance had gotten into the business.”

Andreessen was different, he said at the time. It was started by entrepreneurs and had around 65 people on staff dedicated to helping the portfolio companies succeed. “I think it was started with the idea of saying, ‘If we invented venture capital from scratch what would it look like, and what would a pro-entrepreneurial firm look like?’” Dixon said.

Dixon moved out West and invested in the likes of drone company Zipline; Buzzfeed, the entertainment and media company that had a disastrous SPAC merger at the end of last year, and Oculus VR, which Facebook (now Meta) agreed to acquire in 2014.

But whether it be his background in computers and programming, his longtime commitment to the idea of “decentralization,” or his distaste for traditional Wall Street from his time building algorithms at the high-frequency trading firm—Dixon jumped early into what would become one of the biggest asset-grabbing sectors in venture capital: crypto. For Dixon, blockchains were new computers—a new kind of computational platform. 

It started with a few investments: In 2013, Dixon led Andreessen’s first investment in Coinbase as part of its $25 million Series B round after the crypto exchange graduated from Y Combinator. That year he also led Andreessen’s investment in payments network Ripple Labs.  Then there was data analytics platform TradeBlock, led by former a16z GP Balaji Srinivasan. Marc Andreessen and Dixon quickly became two of the loudest proponents of Bitcoin—and later other cryptocurrencies; the blockchain-based decentralized Web3; and non-fungible tokens, or NFTs. Their thesis: The internet of the future would be built on the blockchain. 

With Dixon and Haun at the helm, a16z closed its first crypto-only fund in 2018 at what now seems like a measly $350 million. In total, Andreessen’s crypto-specific funds now boast more than $3 billion in assets, and it manages money for the University of Michigan’s Endowment Fund and Conway, among other undisclosed limited partners. 

“He just loves working with crypto founders,” Conway says of Dixon, noting that the two of them would get dinner together whenever he was in New York. “That’s his calling right now, building the crypto ecosystem, and he is having a huge hand in it.”

Dixon has led Andreessen’s investments in Coinbase, Uniswap, Ripple, Avalanche, Dapper Labs, Flow, DyDx, and other companies—though Andreessen’s full crypto portfolio also spans Phantom, Alchemy, and, more recently, NFT membership company Bored Ape Yacht Club. Andreessen invests in other funds as well, including Haun Ventures’ $1.5 billion crypto funds, which Haun raised from limited partners after departing a16z at the end of last year. 

“He’s not one to seek the spotlight for himself or anything like that—so whether it’s putting founders in the spotlight or putting other people on the team in that role, he’s very much focused on others around him.” Simpson says, recalling a dinner in Los Angeles for one of a16z’s portfolio companies where Dixon went out of his way to make sure people understood her role and that she was someone to be taken seriously.  

He’s as invested in the companies he’s backed as he is his team, his colleagues say. Yahya says Dixon held biweekly calls with Dapper Labs to discuss strategy in launching a gaming and NFT-focused blockchain (which would become Flow), building on-ramps and off-ramps and recruiting. People told Fortune Dixon has stuck his neck out for portfolio companies he believes in when crypto markets turned sour and other investors began to take a step back.

It’s just starting to become apparent which of Andreessen’s early bets in crypto are panning out. Coinbase went public at a valuation of $86 billion in April 2021—an enormous windfall for Andreessen, which held more than 14% of Coinbase’s voting rights at the company’s listing, per SEC filings (Simpson says a16z invested in 15 Coinbase rounds, including a down round). The Diem Association, a blockchain-based payment system, was acquired earlier this year. 

What’s unequivocal is that Dixon’s personal net worth is mounting as his exits stack up. There’s the likes of Coinbase, of course, but Dixon had also been exiting profitable personal angel investments—like Pinterest, Behance, Warby Parker, and Foursquare—since he joined Andreessen (He has only fully exited Behance). Dixon and his second wife, Elena Silenok—whose retail startup Clothia Dixon invested in as an angel prior to joining a16z in 2012—purchased a two-story penthouse in Tribeca near New York’s City Hall in 2015 (they sold it last year during the pandemic). And they bought a $5.7 million home in Hillsborough, Calif., in 2019. 

But as some investments mature, so do some of the risks Andreessen and Dixon have taken on. One of its portfolio companies, Ripple Labs, has been in a two-year, very public battle with the SEC over whether its two founders had sold $1.3 billion in unregistered securities (the company vehemently denies the allegations). In March, a16z-backed Axie Infinity, the NFT play-to-earn game, experienced a $622 million hack on its platform after the North Korea–based Lazarus Group allegedly used stolen private passwords to validate transactions then withdraw Ethereum and stablecoins. In April, Andreessen Horowitz was named in a lawsuit lodged against its portfolio company Uniswap and the founder over alleged “rampant fraud” taking place on its platform. The exchange is reportedly being investigated by the SEC over how investors use the platform and how it is marketed, according to a Wall Street Journal report from the end of 2021. (Uniswap says the lawsuit claims are “meritless,” and it told the Journal that it is “committed to complying with the laws and regulations governing our industry and to providing information to regulators that will assist them with any inquiry.”)

SEC filings from a16z lay out pages upon pages of risks the firm has taken on by investing in crypto companies. Venture capital is high-risk by nature, but crypto is different. A fund’s GP is responsible for arranging custody of the fund’s digital assets, according to disclosures, and “certain key personnel” are the only individuals with access to private keys needed to access digital assets in certain funds. Should those keys be lost, or the firm’s disaster recovery plan fails, “a limited partner could incur substantial, or even total, loss of capital.”

The next big thing

The German philosopher Immanuel Kant explained that there is a difference between objects as they exist—their essence—and objects as we perceive them. We rely on our own senses and experiences to interpret the world around us in the “phenomenal realm.”

Considering his programmer roots, Dixon finds a surprising number of answers in people—not hard data and product. That was a lesson he’s learned through investing, he said in 2011 at a virtual angel investing event. 

Now he spends most of his time in conversations. “That’s where I get all of my information—is talking to entrepreneurs, talking to people that are smarter than me,” Dixon would say on the Tim Ferriss Show podcast.

Why hasn’t he shared more about himself? It might be that he doesn’t do much outside of work. As he said in a Venture Capital Journal interview in 2013: “I don’t really have hobbies other than blogging and startups. When I was interviewing at AH, they were like, ‘So what do you do for fun?’ In the past I was working at starting my own companies, then on the weekends, I would do the angel investing stuff. It’s really kind of pathetic. They were like, ‘This guy has to get out more.’” Or perhaps it is an effort to protect himself and those he cares about from the army of crypto hackers in search of personal tidbits they can use to get their hands on digital assets.

But Dixon is also complex, and like the technologies he is immersed in, is not without contradictions. He values transparency—but hides much of who he really is behind an avatar. He embraces the philosophy that crypto is transformative and will elevate the everyday person, but he uses his own position of power and status at the hottest fund in the hottest center of the investing world to say so. He is private, but also one of the most public-facing voices in crypto. He likes bone broth and grilled shishito peppers. He plays the German board game Carcassonne and Guitar Hero. He’s fiercely loyal and also a “little awkward.” He spends most of his free time reading and learning. He believes deeply in people and the secrets they hold close. And like that 10-year-old he once was in Springfield, Ohio, he’s still relentlessly searching for the manual that will help him unlock the next big thing.