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MicroStrategy’s Debt Dilemma: A Balancing Act Between Bonds and Bitcoin

October 10, 2023
in Blockchain
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The behavior of MicroStrategy in borrowing money to purchase Bitcoin has stirred quite a controversy. Adam Cochran, a partner at CEHV and a known figure in the crypto space, recently dissected the precarious financial position of MicroStrategy, a company headed by Michael Saylor and known for its large Bitcoin holdings. Cochran outlined the company’s obligations regarding its 2025 and 2028 convertible notes in a series of tweets on October 9, 2023. The notes have pull forward provisions on liquidity, allowing them to be moved to 2025. With a forward of $120 million in revenue against costs of approximately $188 million, MicroStrategy still faces $36 million in coupon payments on its debt.

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MicroStrategy’s Bitcoin Accumulation

MicroStrategy has been aggressively accumulating Bitcoin, under the stewardship of its CEO, Michael Saylor. As of September 24, 2023, the firm holds a whopping 158,245 bitcoins, acquired at an average price of $29,582 per bitcoin, amounting to a total investment of approximately $4.68 billion​1​. The acquisition spree commenced on August 11, 2020, and has seen notable purchases including 29,646 bitcoins for $650 million on December 21, 2020, and 19,452 bitcoins for $1.026 billion on February 24, 2021. In 2023 alone, MicroStrategy acquired 17,778 bitcoins for a total of $494.3 million, as per the purchase records​1​.

Convertible Note Conundrum

Cochran highlighted the potential fallout if MicroStrategy fails to pay the convertible note for 2025, which would convert at a $725 million value against the company equity, causing around 15% dilution for holders. The alternative could be refinancing, but the last issuance had a 6.25% yield before the hiking cycle, and Cochran estimates refinancing could drive yields to a staggering 9%-11%.

The Bitcoin Balancing Act

He further noted that Saylor has a few options to manage this debt. One is leveraging the company’s Bitcoin holdings before the year end, which would exclude it from liquidity calculations and bring $2.8 billion in conversions. Alternatively, they could let the 2025 bonds convert for a 15% dilution, refinance to double-digit debt yields, or sell a portion of their Bitcoin to cover the debt.

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Implications on Bitcoin

Selling Bitcoin, however, could erode confidence and lead to more impairment loss, especially if Bitcoin’s price dips below $20k. Cochran suggests that such a move could potentially lead to MicroStrategy’s downfall, which he believes might be bullish for the markets. This is because a concentration of assets, particularly in a publicly traded entity, can mute upsides, and a short-term wipe could usher in long-term gains.

In a follow-up query by David Miranda, Cochran noted that although corporate debt refinancing usually starts a year in advance, Saylor’s outlier status might push negotiations to the last minute, making the year end a crucial period for MicroStrategy’s financial strategies heading into 2024.

Image source: Shutterstock


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