Nick Tomaino is explaining why CryptoPunks matter while eating steak at Gage & Tollner, the storied Brooklyn chophouse where cherry wood paneling and brass chandeliers preserve a century of New York tradition.

He’s just come from a basketball tournament at Barclays Center, where his team made the semifinals, still carrying that competitive energy into the dining room’s low murmur of conversation and faint clink of martinis.

“It’s art that captures crypto culture,” he says, slicing into a cut of perfectly pink flesh.

The 1confirmation founder and GP owns the Punk that once belonged to 4156, the blue bandana, eight traits, acquired for $3.3 million (“a good price”) from an investor who wanted to take a tax loss. The Punk sits in his office that doubles as an underground sports complex, alongside a Beeple, an XCOPY, and pieces from Coldie and Cryptograffiti.

“I’ve always collected stuff,” Tomaino says. Sneakers on NikeTalk in high school. Rare books like his father. Sports cards that he’s now tokenizing. But his most consequential collection began in 2012 when he bought his first Bitcoin at $3.

He sold at $6, doubling his money. “Everyone says they wish they bought early,” he laughs. “The hard part isn’t buying, it’s holding.”

Recently bought Cryptopunk #4156 for $3.31M

Here’s why: pic.twitter.com/l0GrSLFJBC
— Nick Tomaino (@NTmoney) July 26, 2022

Learning the Hard Way

In 2012, while working at North Atlantic Capital in Maine, Tomaino was analyzing SaaS companies and bored out of his mind. Buying Bitcoin back then meant withdrawing cash from an ATM, sending it through MoneyGram to a sketchy exchange, and hoping it went through. He did it anyway, putting $1,000 into Bitcoin at $3 a coin.

The process was so absurd that it gave him conviction about Coinbase. When he saw Brian Armstrong launch it on Hacker News, Tomaino became one of the first hundred users. “Just link a bank account and buy Bitcoin. Very simple.”

He started evangelizing, using his Yale.edu email address to cold-pitch merchants on accepting Bitcoin. Not as a company representative, just as a believer. He convinced e-commerce companies like Fiverr, Fancy, and Reeds Jewelers and hustled his way into Coinbase’s attention. When Armstrong finally met him, the message was clear: drop out of business school, come work for us.

Tomaino compromised. He’d be Coinbase’s East Coast guy while finishing at Yale School of Management. His business school classmates thought he was insane. He thought what they were doing was shortsighted.

“I don’t have the East Coast mentality about institutional prestige,” he says. “I actually think the stronger the narrative, the further from the truth. Whatever institution you think is super legit, the opposite is probably true.”

“I actually think the stronger the narrative, the further from the truth.”
NICK TOMAINO

Then he got hacked.

“I was all in on Bitcoin,” he recalls. “I woke up groggy one morning and saw what looked like an email from Coinbase saying that the company had updated its terms of service. I clicked the link, gave my password to a spoofed Coinbase site, and boom, my entire net worth was zeroed out. This was a week before two-factor authentication, which would have prevented the hack.”

It was a sophisticated phishing attack that targeted multiple Coinbase employees. At the time, the Bitcoin he lost was worth roughly $50,000. Today, it would be worth nearly $10 million.

For two days, he was wrecked. He thought about quitting crypto entirely, maybe doing “something safer” like insurance. His wife had just moved to the New York area for his business school. Everything felt precarious.

The company ended up covering some of the loss to soften the blow. Not as charity but as recognition that it was a targeted attack. “Very nice of Brian to do that. It was completely my own fault at the end of the day.”

The loss became a blessing. “You can make excuses and dwell on it, or you can be accountable and use it as fuel to go harder.”

Nick Tomaino in 2019. Credit: Courtesy of Nick Tomaino.

From Coinbase to 1confirmation

Three years at Coinbase taught Tomaino what matters in startups: not team, not market, not product in isolation, but product timing. “Brian built a trusted brand that made a new asset class accessible,” he observes. “If you’re a trusted marketplace for an emerging asset class, that’s a great business.”

The early Coinbase days were wild west meets Silicon Valley. Tomaino watched Armstrong navigate regulatory uncertainty, scaling challenges, and the constant threat of hacks. He learned that in crypto, paranoia isn’t optional; it’s survival. Two-factor authentication, cold storage, constant vigilance. The Bitcoin he lost became both tuition and a rite of passage.

By 2016, Coinbase had become big and bureaucratic in his eyes. The scrappy startup where Tomaino could directly impact merchant adoption had turned into something resembling a traditional financial institution. When he left, people called him stupid for abandoning a rocket ship. His answer was simple: “bleeding-edge crypto” was happening elsewhere.

He joined Runa Capital briefly, trying to convince them of crypto’s potential. When they proved too cautious, he started 1confirmation in the summer of 2017. Runa became his first LP, supportive despite his departure.

1confirmation launched with a contrarian premise: while everyone else was starting crypto hedge funds to trade tokens, Tomaino would build a venture fund for products no one understood yet.

“Our worst investments were the hot deals.”
NICK TOMAINO

His first investment: MakerDAO. Then OpenSea, leading their seed round when NFTs were still a punchline. DyDx. Nexus Mutual. SuperRare. Almost every Fund 1 investment returned capital, unheard of in venture and nearly impossible in crypto.

“Our worst investments were the hot deals,” he says. “Companies that raised $10 million from Andreessen. When you’re a first-time fund, you want validation. But social proof at the seed stage is actually a negative signal.”

He lists the failures: Vest (formerly One Protocol), which raised $10 million from a16z and Polychain, hired Stanford kids, and returned 65% of capital. Basis, the stablecoin that raised $100 million and gave back 80%. Both were hot deals that everyone wanted in on.

“At this point, if a deal is really hot before product market fit, that’s negative for me,” he states. “I’ll still consider it, but heat is a red flag.”

To Tomaino, the best founders don’t care about impressing VCs. They believe in what they’re building, whether anyone else gets it or not. OpenSea’s founders were like that. So was Shayne Coplan at Polymarket.

Nick Tomaino and Polymarket CEO Shayne Coplan. Credit: Intercontinental Exchange.

Betting Big on Polymarket

Tomaino first noticed Coplan when he reached out about a 2018 blog post on prediction markets. “He told me about SuperRare and collecting crypto art. He’s a crypto-native guy who actually uses products.”

1confirmation has invested in every Polymarket round, putting more capital into later rounds than earlier ones, a rare move in venture that signals supreme conviction. Tomaino now serves on Polymarket’s board.

“Shayne’s team loves him,” Tomaino observes. “He’s just himself and gets it. He’s only 28 and can be the best leader in crypto that we have.”

When the FBI investigation happened, when the CFTC fined them $1.3 million, Tomaino stayed convicted. “Every setback has ended up being good for the company. Shayne has handled setbacks exceptionally well. Each one has turned into a blessing.”

“Nick is a one-of-a-kind investor. A true independent thinker who has helped Polymarket get to where it is today.”
SHAYNE COPLAN, POLYMARKET CEO

“Nick is a one-of-a-kind investor,” Coplan tells Now Media. “A true independent thinker who has helped Polymarket get to where it is today.”

Polymarket represents something bigger than betting: truth in a world drowning in narratives. “The biggest problem in the world right now is how do we know what’s true?” Tomaino argues. “Social media gets more views out there than controlled media narratives, but algorithms boost things that aren’t true. Prediction markets are an essential tool.”

He sees potential beyond sports and politics. “Creators could have markets on any event relevant to their audience and earn fees. We’re talking to many big creators about this.”

The competition with Kalshi doesn’t bother him. “Positive sum rivalry,” he calls it. “The prediction market space is big enough for multiple winners. Competition pushes everyone to be better.”

His conviction comes from personal experience. “I find truth in crypto in the comments,” he explains. “Not the bots and AI spam, but real comments from real people. Same principle as prediction markets: aggregate wisdom from people with skin in the game.”

Tomaino often returns to a mental model he learned from Virgil Abloh: the intersection of purist and tourist.

“The purist knows every detail, steeped in historical knowledge, but might miss the bigger picture. The tourist doesn’t care about any of that—they just want a product that works.”

Polymarket succeeded at this intersection. So did Coinbase. OpenSea too. Tomaino feels the best founders understand both the crypto community and the mainstream.

“Too purist, you stay small,” he says. “Too tourist, easy come, easy go.”

Nick Tomaino and Bridge co-founders Zach Abrams and Sean Yu. Credit: Courtesy of Nick Tomaino.

Conviction and Crypto Venture

Tomaino sees his rivals as the big funds that everyone fawns over. In his view, they don’t actually believe in human empowerment, the main value Satoshi set forth when creating Bitcoin.

“Think about it. If your LPs are big institutions that lose power when crypto succeeds, do you invest in the products that are empowering billions of people around the world? Probably not,” he says. “This is a big reason why you see so much garbage get funded. That and there was just too much capital raised by dumb, greedy people who had connections to LPs. No one says that out loud, but it’s the truth.”

That mindset shapes how he runs 1confirmation. He keeps the fund deliberately small, in the $50 to $150 million range, prioritizing conviction over scale. “Once you raise a big fund, you have to start investing in narratives,” he says. “My friends who’ve done that might be richer for now, but they aren’t having as much fun as I am.”

“Crypto is about human empowerment. Not just a few VCs getting rich, but actually empowering people around the world.”
NICK TOMAINO

That conviction shows up most clearly in how he talks about Ethereum.

“There are only two cryptocurrencies that are credibly neutral,” Tomaino states. “Bitcoin and ETH. Every other coin is a company coin.”

He’s held this view through every cycle, every Solana pump, and every “Ethereum killer” narrative. “Company coins can have strong narratives and price action short term. But they’re not the hundred trillion dollar, credibly neutral store of value opportunity.”

Earlier last year, when everyone said ETH needed a stronger narrative, Tomaino disagreed. “Not having a strong narrative is actually good. Companies have strong narratives because they pay for media or coordinate marketing. Those come and go.”

In his eyes, the distinction is simple. “Crypto is about human empowerment,” he says. “Not just a few VCs getting rich, but actually empowering people around the world.”

Nick Tomaino and Frenetik Void. Credit: Courtesy of Nick Tomaino.

That contrarian conviction also extends to NFTs, even as floor prices crater and critics declare the movement dead

Tomaino’s digital art collection reads like a condensed history of crypto art. Beyond the famous punk, he owns significant pieces from the movement’s pioneers. “I like art that captures crypto culture, and I love the creative people behind the artwork,” he explains. His office features works that tell crypto’s story, from early experiments to cultural phenomena.

“Crypto-rich people are going to collect crypto art,” he states simply. “Just like traditional rich people collect traditional art. Long-term, scarce crypto art is going to be a great investment.”

He’s particularly drawn to the work of Cryptograffiti, one of the earliest Bitcoin artists. “The historical significance matters. These artists documented crypto culture when nobody else cared.”

“Crypto-rich people are going to collect crypto art.”
NICK TOMAINO

That instinct also shapes how he responds when something in the industry feels off.

On October 23, 2022, Tomaino’s birthday, he posted a Twitter thread questioning the legitimacy of FTX, joining his employee Richard Chen, who had been publicly criticizing the exchange’s regulatory proposals. Two weeks later, FTX collapsed.

“I didn’t know the extent of the fraud,” he says. “I just knew something was off.”

The signs were there: Sam Bankman-Fried pushing legislation that would regulate non-custodial exchanges like custodial ones (benefiting FTX), the Bahamas conference excess, the too-good-to-be-true narrative.

“There were many in the crypto community calling it out, most were anonymous,” he notes. “When everyone else was either shilling FTX, taking FTX money, or buying into the altruism narrative, there were also a lot of people asking questions.”

He comes back, again, to the same signal. “The comments are where you find truth. Real people in the comments were saying something was wrong when the mainstream media and prestige institutions were saying it was the best thing ever.”

Nick Tomaino and Phil Mickelson. Credit: Courtesy of Nick Tomaino.

The Family Man

Tomaino grew up in Gloucester, the fishing town north of Boston, middle class with two younger brothers. Every sport, every season, competition built into the fabric of childhood. Now he’s raising three kids (aiming for five) with the same values.

“I think competition was important for me,” he reflects. “My kids love competing in sports.”

Golf is more than a pastime for Tomaino. It’s part of how he stays sharp. He regularly hits the links with friends who share his competitive edge, including PGA legend Phil Mickelson and wrestling icon Steve Austin.

At a recent Member-Pro golf tournament in the Bahamas, his six, four, and two-year-olds watched the 39-year-old compete alongside professional golfers like Akshay Bhatia, Rickie Fowler, and Sergio Garcia. “It’s good for kids to see their dad still competing.”

“The best thing you can do as a parent is inspire belief in your kids. The best thing you can do as an investor is inspire belief in founders.”
NICK TOMAINO

The balance seems effortless, but it isn’t. “I’m lucky. I’ve done well, I work hard, but I can take time when I need it for family stuff.”

His office serves triple duty: serious basketball games with the team, family and friends, and art education.

The parenting philosophy mirrors his investing philosophy: don’t project too strongly. “Parents’ natural inclination is to project onto your kids: your insecurities, your hopes. Most people err on the side of projecting too much. Better to have a trust God and trust-the-universe mentality, inspire belief.”

“The best thing you can do as a parent is inspire belief in your kids,” he says. “The best thing you can do as an investor is inspire belief in founders.”

Nick Tomaino and Steve Austin. Credit: Courtesy of Nick Tomaino.

The Long Game

Tomaino readily admits that he invests on a longer time horizon than most.

He hasn’t sold Bitcoin since 2012. Never sold ETH. Barely sold any NFTs. “I used to trade when I was younger,” he admits. “Not anymore.”

The philosophy extends to his fund. He backs products people use and founders who believe in something more than getting rich, then waits for time to prove them right.

“Most people treat crypto like public equities because they’re publicly traded,” he observes. “Better to treat it like venture — either 10x plus in five years, or much lower.”

He believes crypto is “human empowerment technology,” while AI in its current state is “human control technology.” He uses ChatGPT and Claude as tools, but worries about people treating them as truth. “ChatGPT reflects media narratives. For truth, I look at prediction markets.”

“ChatGPT reflects media narratives. For truth, I look at prediction markets.”
NICK TOMAINO

His latest interest combines multiple passions: sports cards on-chain. “I want to bet $100K that Wembanyama will be a Hall of Famer. How do I do that?” The answer involves tokenizing cards, creating what he calls “stablecoins for physical collectibles.”

He’s been buying Wemby rookies — silver prizm PSA 10s — at $1,000 average, now worth $1,600. The complexity of knowing which card, which year, which grading company mirrors early crypto’s opacity. “It’s an insider game,” he says. “There’s an opportunity to democratize it.”

The prediction market for 1confirmation’s approach seems bullish. Following the success of Fund 1, both Fund 2 and Fund 3 have Polymarket at a cost basis that now looks prescient. Fund 4 and the NFT fund await their moments.

“I can play the long game,” Tomaino says, finishing his steak. “I’m not interested in chasing anything.”