Tech moguls Peter Thiel and Michael Saylor are setting up crypto treasuries, but some financial analysts warn that their approaches could entail significant risks.
Thiel and Saylor have invested considerable sums in cryptocurrencies via their individual firms and investment strategies: Saylor’s software company, Strategy, is notable for its frequent acquisitions of Bitcoin (BTC), while Thiel has made venture capital investments in crypto firms and launched his exchange, Bullish, which went public earlier in August.
Both are not only looking to expand their holdings but also influence the structure and regulation of the cryptocurrency market. However, their strategies and views on crypto diverge significantly, with companies creating crypto treasuries potentially risking a “death spiral” when prices plummet.
Divergent Crypto Investment Strategies of Thiel and Saylor
Michael Saylor, co-founder and chairman of software firm Strategy (previously MicroStrategy), has stirred up the financial sector with his so-called “infinite money glitch.”
This “glitch” involves Strategy’s methodology of purchasing Bitcoin by issuing stock or equity-linked securities to acquire Bitcoin, which then sits on its balance sheet.
Typically, issuing additional equity would dilute the stock’s value, but substantial Bitcoin purchases tend to elevate BTC’s price, thereby increasing Strategy’s valuation and enabling it to incur more debt.
And thus the cycle continues.
The strategy has been remarkably effective, resulting in a plethora of imitators. The term “Bitcoin treasury company” is becoming increasingly prevalent, with 174 public companies reported to be holding Bitcoin, as per BitcoinTreasurys.net.
Saylor’s crypto approach is focused exclusively on Bitcoin, mainly aiming to accumulate a significant portion of this cryptocurrency, which he views almost metaphysically.
In 2020, he stated that Bitcoin is akin to “a swarm of cyber hornets serving the goddess of wisdom, feeding on the fire of truth, exponentially growing ever smarter, faster, and stronger behind a wall of encrypted energy.”
During a speech at the Bitcoin Policy Institute in March, Saylor asserted that Bitcoin constituted a “Newtonian network,” crucial for the US to sustain its global dominance.
He also proposed that an assertive Bitcoin accumulation strategy by the US government could eliminate the national debt and suggested in various interviews that a national Bitcoin reserve would represent “manifest destiny for the United States.”
Thiel’s strategy, while less revolutionary, is more diversified. In February 2025, the Founders Fund—a venture capital firm co-founded by Peter Thiel in 2005, which has invested in companies like SpaceX, Palantir, and Facebook—put $100 million into Bitcoin and another $100 million into Ether (ETH).
Which crypto investment strategy will prove more effective in the long run:
A) Michael Saylor’s Bitcoin-only approach
B) Peter Thiel’s diversified strategyShare your thoughts in the comments 👇👇👇
— Cointelegraph (@Cointelegraph) August 26, 2025
The Founders Fund holds a 7.5% stake in ETHZilla, a biotech firm that has pivoted into an Ether investment initiative, along with a 9.1% stake in BitMine Immersion Technologies, which Founders Fund aided in raising $250 million in ETH.
Additionally, Thiel has invested in the cryptocurrency exchange Bullish, which went public on August 19, gaining a valuation of $1.15 billion across multiple stablecoins, including USDC (USDC) and PayPal USD (PYUSD).
He’s clearly engaged in the crypto realm and maintains a positive outlook for its growth. However, Thiel has also expressed a more tempered skepticism, particularly concerning Bitcoin. Unlike Saylor’s depiction of it as a “swarm of cyber hornets,” Thiel has previously questioned whether Bitcoin may serve as “at least in part, a Chinese financial weapon against the US.”
“It threatens fiat money, but it especially threatens the US dollar, and China wants to do things to weaken it so China is long Bitcoin, and from a geopolitical perspective, the US should be asking some tougher questions about exactly how that works.”
To summarize, Thiel’s approach provides a more cautious and diversified exposure to cryptocurrencies, while Saylor adopts an aggressive, all-in-on-Bitcoin stance.
Rising Bitcoin Treasury Companies: Is It a Bubble?
The crypto market may soon determine which strategy prevails. Recently, the Bitcoin treasury model advocated by Saylor has been losing momentum.
The model’s premise of “raise capital, convert to Bitcoin, and await appreciation” may seem straightforward, but it also exposes the company to the notorious volatility of Bitcoin markets.
If BTC’s price declines too closely to the Bitcoin-per-share metric, or net asset value (NAV), of a company’s stock, that valuation buffer vanishes, compromising the stock price.
This may initiate a “death spiral,” where a company’s market cap diminishes, limiting its access to capital. Without buyers for its equity or lenders willing to provide funds, the firm cannot expand its holdings or refinance existing debts. If a loan matures or a margin call occurs, forced liquidations become inevitable.
Strategy’s NAV currently stands at 1.4 times its share price. This figure was nearly double the share price back in February, prompting Carnegie Mellon University finance professor Bryan Routledge to tell Fortune, “There’s no rational explanation for that difference.”
Thus, investors in Strategy face risks not only from Bitcoin price fluctuations but also from any factors contributing to the difference between the net asset value and the share price, adding an extra layer of risk.
In recent weeks, both the Strategy stock price and BTC have declined, yet Saylor’s acquisitions of BTC remain relentless. The company purchased 3,081 BTC for $356.9 million in the week concluding August 24.
While market conditions seem relatively stable at present, and the White House maintains a pro-crypto stance, history shows that crypto winters eventually arrive, revealing which strategy endures.
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