Dan Tapiero: Bitcoin at same price as five years ago, says patience still the hardest trade

Why getting rich in crypto is easy but keeping it is nearly impossible

Dan Tapiero, founder of 50T Holdings, frames crypto's core challenge as survival rather than entry. He argues that every three to four years a bear market "attempts to wipe out everyone and then a few survive," and that the real skill is not chasing a single huge multiple but setting a long time horizon.

"Crypto is the easiest place in the world to make money. It's just the most impossible to hold on to it." — Dan Tapiero

He notes that Bitcoin and ETH are roughly at the same price as five years ago, which he says removes near-term enthusiasm for those core assets and makes a 100x repeat unlikely from here, even as he still expects Bitcoin could reach "2, 300,000" and longer term "a million."

Raising capital against the crowd: the Fund IV story

Tapiero describes raising his most successful fund, Fund IV, during the 2022-2023 bear market, a period he calls the hardest to raise money despite his 35-year track record. He says even longtime investors doubted the space after FTX collapsed, asking whether it would "come back."

According to Tapiero, Fund IV is up over 250% gross and has already returned 30% of committed capital 18 months into a ten-year life, with hits including Figure's IPO and Deribit's sale to Coinbase. He contrasts this with his smaller, less successful funds raised during hype cycles, arguing that FOMO-driven capital arrives "at the single worst time usually."

Passing on FTX in favor of Deribit

Tapiero says he saw "red flags" in Sam Bankman-Fried but didn't view him as "a complete fraud." His stated reason for avoiding FTX was valuation discipline: FTX was reportedly offered at roughly 50 times revenue, while his firm was buying Deribit at six to seven times net profit. He says some of his own LPs went around him to invest directly in FTX anyway.

"I could make the excuse to the LP that... this is outside of our valuation range." — Dan Tapiero

The next frontier: tokenizing illiquid assets

Tapiero argues the space is in "the first inning of the digitization of liquid assets" — treasuries, interest rates, commodities, and perps trading. The bigger prize, he says, is tokenizing illiquid assets like real estate and farmland, a thesis he has held since founding an agricultural farmland REIT with Stan Druckenmiller in 2006.

He says his firm would commit "at least 100 million" to a company generating $50-100 million in revenue doing genuine illiquid-asset tokenization, but states he hasn't found one yet. He points to RWA perp trading as a large addressable market and names Variational and Hyperliquid (referred to as "hype") as ways to play the broader liquid-asset trend.

Zcash and the privacy narrative

Tapiero says Zcash has risen roughly 25 times over 18 months, a move he ties to a renewed privacy narrative following unspecified hacks and to institutionalization of Bitcoin through ETFs and DATs, which he believes has eroded the privacy early Bitcoiners valued. He names Barry Silbert and the Winklevoss twins as prominent proponents.

He discloses his firm incubated a project called Zenrock that wrapped Zcash on Solana, but it was hacked and the project closed. He personally does not hold Zcash, saying "you can't do everything," while noting his team was bullish on it roughly 18 months earlier.

The hardest skill: selling into strength

Tapiero says the most valuable but least practiced skill is parting with part of a position when conviction and emotion are highest. He argues investors feel best right when they should be trimming, and recommends setting profit targets before entering a trade.

"No one ever went bankrupt taking a profit... you get rich because in the selling." — Dan Tapiero

He contrasts this with the common pattern of holding through pain, then selling in relief the moment a position recovers rather than when fundamentals justify it, calling repeated failure to take profit "a sin against the market god."

Skepticism toward "money disappearing" and AI-blockchain convergence

Tapiero disagrees with Elon Musk's claim that there will be "no money in 3 years," arguing value will not simply disappear and that humans will keep attaching value to things they want to own. He contrasts this with his conviction that nearly all value will eventually migrate on-chain because it becomes a single, fungible "ledger of truth."

He also argues that most traditional finance figures he encountered at a recent CEO conference did not mention Bitcoin or blockchain, focusing instead on AI, and that they underappreciate how blockchain could serve as the settlement layer for autonomous AI agents transacting value.