The bloom has come off Michael Saylor’s rose.

In the world of bitcoin, no company has captured the public imagination quite like Strategy (née MicroStrategy). Under its executive chair, this erstwhile business software vendor has reinvented itself as a bitcoin investment vehicle. Its pivot in August 2020 from software to “stacking sats” has delivered a 23-fold gain for stockholders, and pioneered the idea of bitcoin treasury companies, inspiring more than 170 imitators. With over 640,000 bitcoin — about 3 per cent of the entire supply — Strategy is a genuine whale in the crypto ocean.

Yet since the unveiling of its so-called 21/21 capital strategy in late October — a plan to raise an eye-watering $42bn to buy more bitcoin — the company’s shares have lagged the very asset they are meant to outperform. So far in 2025, bitcoin has risen 22 per cent compared to just a 9 per cent gain in Strategy, an extraordinarily large “tracking error” by any measure. The stock still trades at a premium of roughly 1.4 times the company’s net asset value, but that premium has shrunk from over three times in November, suggesting mounting market unease.