The original tweet is this...
“Can’t put my finger on it, but I’ve got a feeling Michael Saylor’s and MicroStrategy are introducing a level of risk for the Bitcoin ecosystem in a similar way that Sam Bankman-Fried and FTX did... Hope I’m wrong.”
I then asked ChatGPT to create a blog post based on the above tweet...
At first glance, comparing MicroStrategy and Michael Saylor to Sam Bankman-Fried and FTX may sound alarmist, even conspiratorial. Saylor has been one of the most vocal and consistent proponents of Bitcoin since MicroStrategy began its aggressive BTC buying spree in August 2020. He has made regular public appearances championing Bitcoin as “digital energy” and a “technological imperative.” Unlike the tangled mess of fraud and mismanagement uncovered at FTX, MicroStrategy’s operations appear clean, and its holdings are transparent.
Yet, the concern doesn’t stem from fraud, at least not yet. It stems from something far subtler and more dangerous: concentration risk, leverage, and the potential for unintended contagion. As the Bitcoin ecosystem grows, it's important to recognise that new systemic risks don’t always emerge from malevolence. Sometimes, they grow from overconfidence, hero worship, and too much leverage in the hands of too few.
Let’s break it down.
MicroStrategy: A Corporate Bitcoin Whale
MicroStrategy, a publicly traded business intelligence company, started accumulating Bitcoin in August 2020 under the leadership of Michael Saylor. By June 2025, the company will have amassed over 226,331 BTC worth more than $15 billion at current prices.
To put that in perspective:
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MicroStrategy holds more Bitcoin than any ETF, any single publicly listed company, and possibly any private entity aside from some early miners or Satoshi Nakamoto himself.
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Its holdings represent over 1% of Bitcoin’s total supply, and a significantly higher share of the circulating supply available on exchanges.
These figures alone introduce a form of single-entity exposure that no one anticipated during Bitcoin’s early days. Bitcoin was supposed to be decentralised, censorship-resistant, and robust against any single point of failure. But when one entity controls such a significant percentage of the asset and does so in a leveraged, debt-financed way, it’s worth asking: what happens if they fail?
Leverage: The Ghost of FTX
MicroStrategy has used a mix of convertible bonds, secured loans, and stock sales to finance its Bitcoin purchases. Notably:
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In 2021, MicroStrategy raised $1.05 billion through convertible notes at a 0% interest rate to buy Bitcoin. (SEC filing)
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In 2022, they took out a $205 million loan from Silvergate Bank (yes, that Silvergate) using Bitcoin as collateral.
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In 2024, they began selling shares to raise capital to buy more Bitcoin, effectively tying shareholder equity to Bitcoin price performance.
The concern here isn’t that MicroStrategy will rug pull its Bitcoin or engage in fraud. It’s that it has become a leveraged proxy for Bitcoin that could trigger volatility if things go south.
Sound familiar? This is similar to what FTX did, albeit with far less transparency and outright fraud. FTX, through Alameda Research, became a concentrated node of risk. When FTX collapsed, it sent cascading ripples through the entire crypto market, affecting retail investors, institutional funds, and even regulated firms like BlockFi and Genesis.
Now imagine MicroStrategy being forced to liquidate a substantial portion of its Bitcoin to meet margin calls or debt obligations. That sale could:
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Send shockwaves through the market.
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Damage investor confidence.
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Create the perception (even if unfair) that Bitcoin itself is risky or unstable.
The parallels may be uncomfortable, but they’re real.
Hero Worship and the Saylor Doctrine
One of the key cultural problems that enabled the FTX debacle was the cult of personality around Sam Bankman-Fried. He was seen as a genius, a philanthropist, a regulator-whisperer who could do no wrong, until it all came crashing down.
Michael Saylor has earned his followers differently, through consistent messaging and big bets. But the end result is similar: a significant segment of the crypto community now sees him as a prophet rather than a CEO. That creates blind spots.
MicroStrategy is not a decentralised protocol. It is a company with obligations to shareholders, debt holders, and regulators. It can fail. And if it fails, it will not be just Saylor that pays the price, Bitcoin’s reputation and price could also suffer, even if only temporarily.
Liquidity and Exit Risk
Unlike most Bitcoin hodlers, MicroStrategy has the legal ability to sell BTC at any time to meet financial obligations. If bondholders or creditors begin to doubt MicroStrategy’s solvency, or if equity markets turn hostile, the firm may be forced to sell Bitcoin. Even a modest sale by MicroStrategy could have outsized effects, not just on price but on market psychology.
Again, the comparison to FTX is instructive. Alameda and FTX were tied together in a feedback loop of confidence and collateral. When one faltered, the other collapsed. MicroStrategy isn’t doing anything nefarious, but its fate is increasingly tied to Bitcoin’s price and Bitcoin’s price is increasingly influenced by MicroStrategy’s behaviour. That’s a dangerous loop.
Regulatory Blowback
Let’s not forget the regulatory angle. The SEC and other global regulators have recently approved spot Bitcoin ETFs, ostensibly “de-risking” access to BTC for institutional investors. But if MicroStrategy an SEC-regulated public company starts experiencing financial strain due to its Bitcoin exposure, it could draw regulatory scrutiny on BTC as an asset class.
Consider what happened post-FTX: Congress rushed in with multiple bills, the SEC launched lawsuits, and regulatory uncertainty increased. A high-profile Bitcoin-centred implosion could reintroduce political risk into an ecosystem that’s just beginning to gain mainstream traction.
So, Is MicroStrategy the Next FTX?
No. But also... maybe.
To be clear: MicroStrategy has not committed fraud. It has disclosed its holdings transparently. Its accounting, while unusual, is open to public scrutiny. And Michael Saylor has never made promises he hasn’t backed with action.
But what makes systemic risk systemic is interdependence, confidence, and leverage not just bad intentions.
In the 2008 financial crisis, Lehman Brothers didn’t collapse because it was uniquely corrupt. It collapsed because it was too leveraged, too opaque, and too deeply embedded into the financial system. Its fall triggered panic, because the system had come to rely on its stability. The same was true with FTX.
Bitcoin’s entire value proposition rests on trustless, decentralised finance. But we must recognise when centralised actors become so large, so influential, and so intertwined with the asset’s perception that their collapse could hurt the broader ecosystem.
Conclusion: Hope I’m Wrong
This post isn’t a hit piece. It’s a warning not of Saylor’s malice, but of Bitcoin’s creeping fragility as it becomes increasingly financialised.
Bitcoin survived Mt. Gox. It survived China’s mining ban. It survived the collapse of FTX. But each crisis reshaped the ecosystem.
If MicroStrategy’s strategy fails or even stumbles it may not bring Bitcoin down with it. But it could inflict temporary damage to price, investor sentiment, and global regulatory posture.
Michael Saylor may not be Sam Bankman-Fried. But we shouldn’t need another FTX to remind us that hero worship, leverage, and centralisation are antithetical to the very ethos Bitcoin was built on.
Let’s just hope we’re wrong.
Sources and Further Reading:
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MicroStrategy Bitcoin Holdings: https://www.microstrategy.com/en/investor-relations/bitcoin
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SEC Filing on Convertible Notes: https://www.sec.gov/Archives/edgar/data/1050446/000119312521045739/d126945d424b5.htm
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FTX Collapse Explained (CoinDesk): https://www.coindesk.com/learn/ftx-collapse-explained/
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Michael Saylor’s “Bitcoin is Digital Energy” Speech: https://www.youtube.com/watch?v=e8Yjf8h4Q9Y
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Analysis of MicroStrategy’s Leverage (Lyn Alden): https://www.lynalden.com/microstrategy-bitcoin/