Bitcoin Is Going to $1 Million: What 25 Years on Wall Street Taught Dan Tapiero About Risk, Conviction, and Crypto

In this episode of When Shift Happens, I sit down with Dan Tapiero to explore his journey from Wall Street to crypto. We talk about the lessons he learned working with legendary investors like Stan Druckenmiller and Steve Cohen, the painful experiences that shaped his approach to risk, and why he believes Bitcoin is heading to $1 million over the next decade.

Today, Dan is the founder of 10T Holdings and 1RT, managing $1.5 billion across 23 crypto companies. But behind the numbers is a mindset shaped by discipline, long-term thinking, and a deep understanding of macro change.

Early Lessons in Risk and Resilience

Dan’s career started in the high-pressure world of macro trading, with a 3:00 a.m. shift at Tiger Management. His earliest lesson? Structure your life to perform consistently. “If I don’t get eight hours of sleep, I take the time off I need to catch up,” he says.

His wake-up call in risk management came in 1994, when a large personal bet on Japanese government bonds collapsed. “In one week, I lost half of everything I’d made the year before.”

Although the trade was directionally right long term, the short-term volatility was unforgiving. That experience helped form one of his core principles: never be in a position where you can’t come back. “I give up a little bit of the upside to have control of the downside,” he explains.

What the Greats Taught Him

Dan spent time with some of the most successful hedge fund managers of the past few decades. From Julian Robertson, he learned how to develop a long-term, structural macro view. From Steve Cohen, he picked up the value of short-term sensitivity to market shifts, and also humour. “He was actually very funny on the trading floor,” Dan recalls. “People got his personality wrong.”

But it was Stan Druckenmiller who gave Dan his confidence. “He validated my mental process. After working with him, I stopped doubting myself.” Together, they launched an agricultural land investment that grew into one of the largest private farmland REITs in the U.S., eventually selling to a Canadian pension fund for $450 million.

Embracing Uncertainty

Dan views uncertainty as a prerequisite for success, especially in investing. “If there’s no uncertainty, you won’t make any money,” he says. But embracing uncertainty doesn’t mean ignoring risk. He points out that many investors get caught up in feeling good about a position right before it turns against them. “When you start thinking about buying a house or feeling rich, that’s when you should sell,” he says. “Because that feeling usually comes right before the fall.”

Rather than chasing 30x returns and wild volatility, Dan structures his funds for longevity. “I don’t ever want to be in a position where I’m so down that I can’t recover,” he explains. It’s a mindset that has kept his drawdowns minimal, even through crypto’s toughest years.

The Bitcoin Epiphany

Dan’s entry into crypto came after the 2018 bear market. With Bitcoin around $4,000, he saw a familiar setup: capitulation followed by opportunity. “It was either going to zero, or it was the bottom,” he says. He started buying for himself, for his children’s school endowment (which grew from $5M to over $60M), and eventually through what would become 10T Holdings.

The major convincing factor was a structural macro shift.

“Bitcoin is the greatest decentralized network ever built,” he says. “At the time, Amazon was worth $2 trillion, and Bitcoin was worth $300 billion. That didn’t make sense to me.”

That comparison gave rise to the name of his fund — 10T, short for 10 trillion. “I thought the entire space could 30x in ten years. Today, we’re at around 5 trillion. I think we’re heading for 50.”

Building for the Next Decade

Through his funds, Dan focuses on growth-stage crypto companies, i.e., those generating $50M+ in revenue, and increasingly, on special situations and secondaries. His portfolio is highly concentrated: “$700 million of the $1.5 billion is in just four companies.” He also has board representation in 11 of them, giving him direct insight into company operations.

Dan believes this institutional approach is necessary if crypto is to go mainstream. “Coinbase can’t be the only public crypto company. We need 40 or 50. That’s how we bring legitimacy to the space.”

He’s also preparing for the next wave of token-native businesses. “All value will eventually be on-chain,” he says, though he admits the transition will take time.

Conviction, Morality, and the Long View

Dan's portfolio exposure to crypto is over 50% both personally and through his funds. But he doesn’t trade. “I don’t talk about it. I don’t think about it. I just hold it.”

Beyond strategy, Dan values character. “The worst advice I got early on was to hire the smartest guy. No. Hire the one with the best values and the most passion.” In a space where grifters often outshine builders, Dan’s grounded approach is refreshing. “I’m a fiduciary. My job is to protect and grow my investors’ capital. That’s it.”

Dan Tapiero doesn’t make flashy bets or wild predictions. But he does believe in transformation. His bet is simple: the world of value is moving on-chain, and the institutions that don't follow will be left behind.

“Anybody can make a fortune short-term,” he says. “But the real challenge is not getting wiped. That’s how you win.”

👉If you enjoyed reading the summary, head over to When Shift Happens on YouTube or your favorite podcast platform to access the full convo.