Tech billionaires Peter Thiel and Michael Saylor are launching crypto company treasuries, yet some financial analysts caution that their methods may involve considerable risk.
Both Thiel and Saylor have invested heavily in cryptocurrencies via their respective firms and investment channels: Saylor’s software company Strategy frequently purchases Bitcoin (BTC), while Thiel has funded various crypto enterprises and recently took his exchange, Bullish, public earlier this August.
Each aims not only to increase their holdings but also to influence the direction and regulation of the cryptocurrency sector. However, significant differences exist in their strategies and perspectives on crypto, with companies creating crypto treasuries potentially facing a “death spiral” during downturns in prices.
Contrasting Crypto Investment Strategies of Thiel and Saylor
Michael Saylor, co-founder and chairman of software company Strategy (previously MicroStrategy), has made headlines in the financial realm with what has been termed an “infinite money glitch.”
This “glitch” pertains to Strategy’s method of acquiring Bitcoin, where it issues stock or equity-linked securities to purchase Bitcoin and retains the asset on its balance sheet.
Typically, issuing more equity would depress the stock price, but substantial Bitcoin buys elevate BTC’s price, leading to an enhanced valuation for Strategy and facilitating further debt issuance.
And the cycle perpetuates.
This strategy has proven so effective that it has inspired many imitators. The term “Bitcoin treasury company” is becoming increasingly prevalent in finance, with reports indicating that 174 public companies are holding Bitcoin, according to BitcoinTreasurys.net.
Saylor focuses exclusively on Bitcoin, aiming to amass the largest possible quantity of the cryptocurrency and attributes nearly metaphysical qualities to the asset.
In 2020, he tweeted that Bitcoin “is 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.”
In a speech at the Bitcoin Policy Institute in March, Saylor stated Bitcoin was a “Newtonian network,” whose control is essential for the US to maintain global dominance.
He further proposed that a bold Bitcoin accumulation strategy by the US government could erase national debt and insinuated in various interviews that a national Bitcoin reserve represents “manifest destiny for the United States.”
Thiel’s strategy, while less revolutionary, is more varied. In February 2025, Founders Fund, a VC firm co-founded by Peter Thiel in 2005, which has backed firms like SpaceX, Palantir, and Facebook, invested $100 million in Bitcoin and another $100 million in 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 7.5% of ETHZilla, a biotech firm that has evolved into an Ether investment vehicle, along with a 9.1% share in BitMine Immersion Technologies, which Founders Fund assisted in raising $250 million in ETH.
Thiel has supported a cryptocurrency exchange, Bullish, that went public on Aug. 19, achieving a $1.15-billion valuation across various stablecoins, including USDC (USDC) and PayPal USD (PYUSD).
He is clearly committed to the crypto sector and optimistic about its future, but Thiel has also exhibited a degree of caution, especially concerning Bitcoin. Unlike Saylor’s portrayal of a “swarm of cyber hornets,” Thiel previously expressed the concern that Bitcoin may, at least partly, serve as a Chinese financial tool 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.”
In summary, Thiel’s methodology adopts a more prudent and diversified approach to cryptocurrencies, while Saylor pursues an assertive, all-in-on-Bitcoin strategy.
Rise of Bitcoin Treasury Companies: Are They in a Bubble?
The crypto landscape may soon determine which strategy prevails. Recently, the Bitcoin treasury approach championed by Saylor has experienced a decline in momentum.
The model’s premise of “raise capital, convert to Bitcoin and wait for appreciation” might be relatively simple, but it renders the company susceptible to Bitcoin market volatility.
If BTC’s price drops too close to the Bitcoin-per-share metric, or the net asset value (NAV), of a company’s stock, that stock loses the valuation cushion designed to elevate its price.
This could lead to a perceived “death spiral” where, as a company’s market value diminishes, so does its ability to access capital. Without buyers for the company’s equity or any lenders, the business cannot grow its holdings or refinance existing debt. Should a loan mature or a margin call occur, enforced liquidations will ensue.
Strategy’s NAV currently stands at 1.4 times its share price. That ratio was almost double the share price in February, prompting Carnegie Mellon University finance professor Bryan Routledge to remark to Fortune, “There’s no rational explanation for that difference.”
As a result, Strategy investors encounter risks not only from Bitcoin price fluctuations but also from “whatever is driving this difference between the net asset value and the price of the shares … That extra component is an additional source of risk.”
Recently, Strategy stock has plummeted alongside BTC; however, Saylor’s BTC acquisitions continue without pause. The company recently bought 3,081 BTC for $356.9 million in the week ending Aug. 24.
Current market conditions appear relatively stable, supported by the White House’s pro-crypto stance. Yet crypto winters inevitably arrive, and when they do, the market will reveal which strategy endures.
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