E191: Dan Tapiero: After 35 Years, I Figured Out The Secrets To Getting Rich In Crypto

Dan Tapiero’s central lesson is that making money in crypto can be easier than keeping it. Bear markets return every three or four years, test investors’ conviction and can erase gains. He sees patience as a learned skill: investors need to tolerate uncertainty, criticism and the possibility of being wrong. FOMO often pushes people to invest after an idea has become popular, which he considers a poor entry point. He recommends setting an objective, investing against a clear view and thinking in five- to ten-year horizons rather than expecting a quick 100x.

Tapiero advises deciding how to take profits before investing. One example is risking $1 to make $5, then taking some money off the table; if the fundamentals continue to improve, an investor might sell half and hold the rest. He cautions against becoming completely attached to a position and suggests considering a sale when an investment feels especially rewarding. It took him 15 years, from age 23 to 38, to feel fully confident as an investor, with lessons from Julie Robertson, Steve Cohen and Stan Druckenmiller. Because younger investors may underestimate the pain of losses and the time needed to recover, he suggests most people use a capable manager and manage perhaps 10%–15% of their investments themselves.

His experience also shapes his view of risk and fund management. In 2023–24, after 35 years investing and with more than $1 billion in assets under management, Tapiero still found fundraising difficult amid the bear market and after FTX. 50T’s fourth fund had a maximum drawdown of about 10%–15% while Bitcoin fell 80% in the 2022–23 bear market; 18 months into its 10-year life, it was up more than 250% gross and had returned 30% of committed capital. Tapiero said 50T generally avoided companies valued above five to ten times revenue and passed on more than 400 deals over six years. He declined FTX, citing red flags and a valuation around 50 times revenue, and instead invested in Deribit at six to seven times net profit. He said Deribit dominated Bitcoin and ETH options trading for six or seven years before Coinbase acquired it in what he described as the market’s largest M&A transaction.

Tapiero’s investment thesis is that liquid assets will move on-chain first, while putting illiquid assets on-chain is crypto’s “holy grail.” He said 50T would invest at least $100 million in a company generating $50 million to $100 million in revenue from genuinely tokenizing illiquid assets. His interest in the problem predates crypto: he founded Agcoa with Druckenmiller in 2006 to aggregate farmland holdings; it became the largest private farmland holder and was sold in 2013. For digital assets, 50T also backed “picks and shovels” businesses because Tapiero could not know which blockchains or uses would prevail over a decade. He cited Figure, Circle and Deribit as major successes, and said 50T bought Circle stock during the 2023 bear market at roughly three to four times revenue from a seller needing liquidity.

On prices, Tapiero said Bitcoin could reach $200,000–$300,000 in the near term and possibly $1 million over the long term, but he cautioned that buyers at $1,000 or $100,000 had already made 100 times their money and should not expect another 100x from current levels. He said Zcash had risen 25 times in the preceding 18 months, with demand for privacy contributing to interest; his team had been bullish for 18 months because it offered something distinctive and crypto-native. He sees RWA perpetual trading as an early, innovative area with a potentially very large addressable market, citing Hype and Variational as exposure. Traditional institutions are adopting Bitcoin, ETH and Solana, and he expects crypto-native and traditional finance to meet as more records, documents and property rights are verified on-chain.

For Tapiero, getting rich is not limited to holding crypto assets. Building or joining a business he believes in can provide equity ownership and reduce exposure to crypto price swings, although the business may fail. He recalled that his physical-gold business grew while gold prices went sideways for six or seven years before the business took off. He also stresses the ability to pivot, pointing to Circle’s Jeremy turning toward stablecoins in 2019–20 after Poloniex nearly pulled the business under in 2016–18. Ultimately, he defines a rich life through independence, freedom, family balance and the ability to pursue personal interests.