While tech billionaires Peter Thiel and Michael Saylor have established financial liabilities for crypto companies, some financial observers have noted that their strategies can pose significant risks.
Both Thiel and Saylor pour a significant amount of capital into cryptocurrency through their respective companies and investment vehicles. Saylor bought frequent Bitcoin (BTC) in his software corporate strategy and through his exchange, which was published in early August with Thiel through venture capital investments in Crypto companies.
Each of them not only seeks to expand his holdings, but also wants how the cryptocurrency industry is shaped and regulated. However, there are still significant differences in each strategy and outlook on crypto, with companies that decide to form the Cryptocurrency likely to invite a “death spiral” when prices crash.
Thiel and Saylor have different crypto investment strategies
Michael Saylor, co-founder and chairman of Software Company Strategy (formerly MicroStrategy), has created waves in the financial world through what is called the “infinite money glitch.”
“Glitch” refers to a strategy approach to purchasing Bitcoin. This approach issues stocks or securities related to stocks to buy Bitcoin and holds assets on the balance sheet.
Normally, issuing more shares will reduce the value of the stock, but it will result in a significant increase in Bitcoin purchases, a rise in BTC prices, and then an increase in the strategy valuation, allowing you to issue more debts.
And the cycle continues.
The strategy has been so successful for its strategy that it has gained many imitators. The term “bitcoin financing company” has become increasingly common in the financial world, with 174 public companies reportedly owning Bitcoin, according to Bitcointreasurys.net.
Saylor’s crypto strategy is focused exclusively on Bitcoin. That is, it accumulates as much of the cryptocurrency as possible, and contains almost metaphysical properties of the assets.
In 2020, he wrote that Bitcoin is a flock of cyberhornets serving the goddess of wisdom, feeding the fire of truth, growing smarter, faster, stronger behind the wall of encrypted energy.
In a speech at the Bitcoin Policy Institute in March, Saylor said that Bitcoin is a “Newton Network” and that control of the US is necessary to maintain global power.
He further suggested that an aggressive Bitcoin accumulation strategy from the US government could erase national debt, and in other interviews suggested that the National Bitcoin Reserve is “a clear fate for the US.”
Thiel’s strategy is less groundbreaking, but more diverse. In February 2025, Founders Fund, a VC company co-founded by Peter Thiel in 2005, backed companies such as SpaceX, Palantir and Facebook, invested $100 million in Bitcoin and another $100 million in Ether (ETH).
Which crypto investment strategies prove to be more effective in the long term:
a) Michael Saylor’s Bitcoin-only approach
b) Peter Thiel’s diverse strategiesShare your thoughts in the comments
– Cointelegraph (@cointelegraph) August 26, 2025
Founders Fund owns 7.5% of Ethzilla, a biotechnology company that has been transformed into an etheric investment vehicle, and owns a 9.1% share of Bitmine Immersion Technologies, which helped Founders Fund raise $250 million in ETH.
Thiel also supported the bullish cryptocurrency exchange that was released on August 19th, and received a $11.5 billion valuation, which received several silly, silly, silly valuations, including USDC (USDC) and PayPal USD (PYUSD).
He is clearly invested in the crypto sector and is optimistic about its growth, but Thiel also shows even more measured skepticism, particularly regarding Bitcoin. Far from Saylor’s “a flock of cyberhornets serving the goddess of wisdom,” Tiel previously wondered whether the assets were, at least “not in part, China’s financial weapons against the United States.”
“It threatens Fiat’s money, but especially since it threatens the US dollar and China wants to do things to weaken it, so China is a long bitcoin and from a geopolitical perspective, the US should ask some more harsh questions about exactly how it works.”
In short, Thiel’s approach offers more cautious and diverse exposure to cryptocurrencies, but Saylor takes an offensive, direct exposure, an all-in-bitcoin strategy.
Bitcoin finance companies are on the rise: is it a bubble?
The crypto industry may soon find out which strategy wins. In recent weeks, the Bitcoin financial model defended by Saylor has lost steam.
The essay on the model “raising capital, converting it to Bitcoin, waiting for gratitude” may be fairly easy, but it makes the company vulnerable to the infamous volatility of the Bitcoin market.
If the price of BTC is too close to the stock metric per bitcoin of a company’s stock, or the net asset value (NAV), the stock will lose the valuation buffer that is supposed to raise the stock price.
This could lead to a “death spiral,” where access to capital is expected to be reduced as the market capitalization of a company shrinks. Without a person to buy a company’s shares or lenders, the company cannot expand its holdings or refinance existing obligations. If the loan matures or a margin call occurs, forced liquidation will continue.
Strategy’s NAV is currently clocking at 1.4 times the stock price. It was almost twice the stock price in February when Brian Routledge, a financial professor at Carnegie Mellon University, told Fortune “there is no reasonable explanation for that difference.”
Therefore, strategic investors face risks not only because of fluctuations in the price of Bitcoin, but also because “whatever drives this difference between net asset value and stock price, its additional component is an additional source of risk.”
Strategic stock prices have slumped alongside BTC over the past few weeks, but Saylor’s BTC purchase run continues unabated. The company purchased 3,081 BTC for $356.9 million in the week ending August 24th.
For now, the market situation may be relatively stable, with policies from the White House still remaining custody. However, the crypto winter is always here and when they do, the market will see which strategies will survive.
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