Here's a question: What do you get when you combine an electrical engineer, a kiteboard, and Thanksgiving weekend 2010? Answer: A venture capitalist who shouted about Bitcoin into an empty room on Twitter, got zero replies, and went on to back some of the biggest tech companies of the past decade anyway.

Bill Tai is not your typical investor. He doesn't have an office. He doesn't have assistants or managers. He's been living what he calls "the metaverse on Zoom" for years, finding billion-dollar companies while kiteboarding around the world. And his track record speaks for itself: 23 companies gone public, early investments in Zoom, Twitter, Canva, and Dapper Labs, plus he's currently Chairman of Hut8Corp (HUT), the third-largest Bitcoin miner by stockpiled BTC.

In a conversation with Anna Tutova, founder of AI Crypto Minds, Tai shared the unconventional path that led him from designing computer chips in 1980s Silicon Valley to becoming one of the most successful angel investors in tech.

From Silicon Valley to Silicon Chips to Venture Capital

Tai's journey started in the most conventional place imaginable for a future tech investor: electrical and computer engineering school. "I was originally trained in electrical and computer engineering and was trained to design computer chips initially," Tai explained. "I came out to Silicon Valley in the eighties, I was just lucky to be kind of there at the formative stages of the basic technology that would underpin everything else."

He joined silicon-related companies in those early days, and both went public. By 1991, he had transitioned into venture capital. Then he did something unusual: he took a few years off and started kiteboarding. A lot. That decision would turn out to be more strategic than it seemed.

The Metaverse Before the Metaverse

When Web 2.0 emerged, Tai came back to investing. But in 1999, something interesting happened. His friend Philip Rosedale, who was then CTO of RealNetworks, told Tai he wanted to take Neil Stephenson's science fiction novel "Snow Crash" and build it in real life.

The result? Second Life, one of the first real physics-based motion metaverses. And crucially, Rosedale introduced the Linden dollar in 2003, a digital currency that existed years before Bitcoin.

"So, when Bitcoin came out, I had already done a little bit of work on peer-to-peer networks," Tai said. This context made him uniquely prepared for what came next.

Shouting Into an Empty Room About Bitcoin

On Thanksgiving weekend 2010, Tai stumbled across Bitcoin's whitepaper. His reaction was immediate enthusiasm. He tweeted: "Is anyone else using this peer P2P currency, Bitcoin?"

The response? Nothing. "It was like shouting into an empty room," Tai recalled. "There were no replies. There were literally no replies or likes, how could this be? This is so cool, but nobody cares."

But that didn't stop him. Tai had experimented with peer-to-peer networks back in 1999-2000 for video content distribution. He believed in the underlying technology. "I also believed in the digitization of currency from the Linden Dollar days at Second Life, the peer-to-peer underlying indelible accounting," he explained. "The ability to have a currency that was not controlled by a single government was interesting. I did believe in the principles."

That belief led him to the people who would found Bitfury, which became responsible for a substantial portion of Bitcoin blockchain rewards at the time. Tai joined its board. Today, he chairs Hut8Corp (HUT), a major player in Bitcoin mining.

The Track Record: Zoom, Canva, and the Top Disruptors

When asked about recent investments, Tai pointed to an interesting metric: CNBC's annual list of the 50 top disruptive private companies. Of the top ten, he's backed three: Lineage Logistics (No. 9 in 2023), Canva (No. 5), and Dapper Labs (No. 9 in 2022).

"I was the first investor in Zoom video and helped catalyze what became Canva," Tai said. The Canva story is particularly wild. "I literally met Melanie when she was a young 20 something woman making essentially high school yearbooks out of her living room. And now she's running this company that's over $3B in revenue. And it's been profitable for years."

How does that happen from a small town like Perth, literally on the other side of the planet from Silicon Valley? "Because I went there on a kiteboard trip," Tai said.

Canva's last valuation was $42 billion, by the way. Not bad for a kiteboarding connection.

Creating the First NFT for Charity

Tai isn't just investing in crypto companies. He's actively building in the space as co-founder of two NFT projects: MetaGood and OnChainMonkey.

The MetaGood story started with his investment in Dapper Labs. When he funded them, he could see the power of marketplaces around CryptoKitties. "I asked Dapper Labs to create for me a special edition crypto kitty that I could auction off to support an ocean charity," Tai explained. "So, they created Honu Kitty for me, and I launched it at one of my Blockchain summits that I was doing and still do with Sir Richard Branson on his island, Necker BlockchainSummit.org."

Honu Kitty sold for about $50,000, becoming the first-ever NFT for ocean charity.

In 2021, Tai brought together Danny Yang, who ran the Stanford Bitcoin Meetup groups in 2013, and Amanda Terry, who had worked at Twitter, X, and NBC, to create MetaGood. The company created the OnChainMonkey NFT collection, which was also the first-ever fully on-chain collection completed in one transaction.

Decentralized Social Media and the Future

As an early investor in Twitter, Tai has thoughts about where social media is headed. "The soil is ripe for the planting of those kinds of seeds to create more decentralized versions where you, as the individual, have a little bit more sovereign identity, a little bit more control over your own data set, and can steer the marketing of that data on an opt in basis and possibly actually get rewarded for your own participation in that," he said.

He also sees innovation spreading beyond Silicon Valley's borders. "Technology is truly becoming decentralized in a way," Tai observed. "I think most of the good that advanced development comes from economically advanced countries. But I think it's no longer innovative. As we've gone to the expression layer on the UI, it started to expand everywhere and data science started to span everywhere."

The Kiteboarding Network Advantage

When asked how he operates without managers or assistants, Tai pointed to a pivotal moment about ten years ago. "My life completely changed about ten years ago, when Eric Yuan, who ended up founding Zoom, asked me to fund him and I said yes on the spot."

When Zoom was born, Tai had a network of techie friends around the world who used it to communicate. "I think because I've been able to effectively live on Zoom, I've had a competitive advantage," he said.

But the real secret weapon is the kiteboarding network. Larry Page and Sergey Brin learned to kiteboard before Google went public. Elon Musk, Drew Houston (Dropbox founder), Jamie Siminoff (Ring founder), Melanie Perkins (Canva founder), and Eric Yuan (Zoom founder) have all been involved in Tai's kiteboarding community at one time or another.

"So, I find a lot of my companies through just my personal network," Tai explained. "I think there's a certain construct for starting building and operating a group of people that are not in the same place, and you can still get a lot done. I think it's a different operating style that is available to people today because the world is a metaverse on Zoom."

It's an unconventional approach to venture capital, but when you've backed 23 companies that went public and have three in the top ten of CNBC's most disruptive companies, maybe shouting into empty rooms about Bitcoin and kiteboarding with tech founders is actually the smart play.