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Beware of the Bitcoin Boom-Bust Cycle: The Risk of a MicroStrategy Sell-Off

by Ram ben Ze'ev


Beware of the Bitcoin Boom-Bust Cycle: The Risk of a MicroStrategy Sell-Off
Beware of the Bitcoin Boom-Bust Cycle: The Risk of a MicroStrategy Sell-Off

MicroStrategy’s relentless accumulation of Bitcoin (BTC) has long been a bullish signal for both retail and institutional investors. The company’s Bitcoin buying spree has created a cycle where it borrows to buy BTC, driving up demand and indirectly influencing the price of Bitcoin and its own stock, $MSTR. However, this strategy comes with a potential dark side. If MicroStrategy, pressured by debt obligations or a need to realize profits, decides to sell a significant portion of its Bitcoin holdings, the impact on the market could be substantial, triggering a cascade of events that would leave investors reeling.


While the allure of buying BTC at a potentially reduced price following a sell-off may tempt some investors, history suggests caution. Bitcoin has gone through major downturns before, leaving “bottom buyers” stranded in a sea of losses. To understand the possible fallout from a major corporate Bitcoin sale, let’s examine the key risks and why buying on the dip could turn out to be a costly misstep.


The Impact of a Large-Scale Bitcoin Sell-Off by MicroStrategy

MicroStrategy holds over 150,000 BTC, making it one of the largest corporate holders of Bitcoin. If the company were to offload a substantial portion, it would likely increase the market’s supply and create immediate downward pressure on BTC’s price. This situation could be exacerbated by the following:


  1. Market Sentiment and Panic Selling: MicroStrategy has been one of Bitcoin’s most vocal corporate backers. A sale would be perceived as a lack of confidence in BTC, potentially sparking panic among other investors who view $MSTR as a proxy for Bitcoin exposure. This could lead to a cascading effect, where other investors rush to exit their positions.

  2. Liquidity Constraints: While Bitcoin markets are relatively liquid, sudden large sell orders can overwhelm buy orders. This could create sharp price drops, leaving the market vulnerable to rapid, extreme volatility.

  3. Interconnected Market Impact: MicroStrategy’s sell-off could ripple through other Bitcoin-exposed assets, including ETFs, mining stocks, and blockchain-related equities. These sectors would likely see declines as well, amplifying the sell-off across the crypto and traditional financial markets.


The Trap for “Bottom Buyers”: Lessons from Previous Crashes

Bitcoin’s history shows a pattern of severe drops following bullish rallies, often wiping out late buyers or those hoping to capitalize on dips. Here are some cautionary lessons from past crashes that highlight the risks for those considering “buying the dip” if MicroStrategy begins selling:


  • December 2017 to December 2018: After reaching an all-time high, Bitcoin plummeted 84%, wiping out speculative gains and leaving many investors with severe losses.

  • March 2020: As markets reacted to the COVID-19 pandemic, BTC suffered a 50% drop in just a few days, catching holders off guard.

  • May 2021: Bitcoin fell 53% after months of record-breaking highs, as regulatory concerns and other factors disrupted market confidence.

  • June 2011 (99%), August 2012 (56%), April 2013 (83%), and December 2013 (50%): Each of these periods saw significant price declines that led to devastating losses for many investors who bought near the top or on smaller dips during the downturn.


In each case, Bitcoin’s volatility punished those who believed they were buying at a discount, only to see prices continue to decline as the market readjusted. MicroStrategy’s potential sell-off could trigger a similar downward spiral, trapping buyers who believe they’re seizing an opportunity but ultimately find themselves holding an asset in freefall.


Why a MicroStrategy Sell-Off Could Be Especially Dangerous

The risks surrounding a MicroStrategy sale are unique due to the following factors:


  1. Leverage and Debt: MicroStrategy has taken on significant debt to fund its Bitcoin purchases. If Bitcoin’s price declines sharply, the company’s debt obligations may become unsustainable, further incentivizing it to sell BTC and worsening the market impact.

  2. Institutional Confidence: Many institutional investors are watching Bitcoin’s corporate adoption closely. A significant sale by MicroStrategy could validate concerns that Bitcoin is too volatile for corporate balance sheets, potentially leading to a reduction in institutional interest and amplifying the downward pressure.

  3. Regulatory Attention: A rapid drop in Bitcoin’s price due to a major corporate sell-off could attract regulatory scrutiny. If regulators decide that Bitcoin holdings on corporate balance sheets pose financial stability risks, they could impose stricter rules on such practices, further dampening institutional interest.


Should Investors “Buy the Dip” or Stay Cautious?

For those watching the market, it might be tempting to jump in if Bitcoin’s price drops after a MicroStrategy sale. But history suggests that following institutional exits without careful risk management can lead to severe financial losses. Here are some reasons to stay cautious:


  • Market Cycles and Sentiment Shifts: As past crashes have shown, Bitcoin’s bullish phases often end in significant downturns. If MicroStrategy’s exit signals a shift in sentiment, the market could see sustained downward pressure as other investors offload holdings.

  • Potential for a “Long Winter”: Following previous crashes, Bitcoin often took months, if not years, to recover. Investors buying on a dip triggered by a major sell-off may need to be prepared for a long period of low or negative returns.

  • Liquidity and Volatility Risks: If MicroStrategy sells in stages, the market could see sustained volatility, with unpredictable price swings that make it challenging to enter or exit positions at favourable prices.


Conclusion: The Perils of Betting Against Bitcoin’s Volatility

MicroStrategy’s decision to sell Bitcoin, if it happens, could send shockwaves through the crypto market, triggering price declines and challenging the “safe haven” narrative around Bitcoin. Investors who consider buying during a potential dip should carefully assess their risk tolerance, as history has shown that Bitcoin’s price can fall far further than expected and remain depressed for prolonged periods.


The Bitcoin market, despite its maturity, remains a volatile and unpredictable space, where the actions of a single influential holder can alter the trajectory. For those hoping to time the market, it may be wise to remember the lessons of 2017, 2020, and 2021—what looks like an opportunity to buy the bottom may, in fact, be the beginning of a steep and prolonged descent.


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