Jim Cramer questioned investing in Strategy Inc (NASDAQ: MSTR) as a proxy for Bitcoin exposure during the 1 October episode of Mad Money. Despite Strategy's 76% rally in the third quarter, Cramer suggested buying Bitcoin directly instead. Strategy continued accumulating Bitcoin in September, purchasing 1,665 Bitcoin for $142.7 million. Total holdings reached 847,666 Bitcoin at an aggregate cost of $63.95 billion. The company also reported $5.02 billion in US dollar reserves and $1 billion in additional cash. Strategy sold approximately 1.47 million common shares for $246.2 million during 21–27 September to fund Bitcoin purchases and preferred-stock repurchases. The company's enterprise-value-to-Bitcoin-holdings multiple stood at approximately 1.14x, compared with 0.72x for peer Metaplanet.

MicroStrategy, now called Strategy, purchased just 334 Bitcoin for $28.7 million last week whilst spending $176.3 million buying back its own preferred stock. The company now holds 848,000 BTC. The firm repurchased approximately 1.77 million shares of Stretch (STRC), a preferred stock paying 12% annual dividends. Most funding came from USD Cash reserves, with $154.1 million allocated to buybacks versus only $13 million for Bitcoin. Gold advocate Peter Schiff suggested Strategy has lost its Bitcoin-buying power because STRC no longer raises fresh capital. The company booked a $20.91 billion gain on Bitcoin in the third quarter. Smaller rival Strive purchased 2,000 BTC during the same period, six times Strategy's weekly acquisition.

MicroStrategy has transformed itself into a leveraged Bitcoin holding vehicle, with shares now trading as a magnified proxy for the cryptocurrency. The stock is down 51% over the past year but has surged 37% in the past month, tracking Bitcoin's recent bounce to roughly $84,220. MSTR's market capitalisation of $62 billion exceeds Coinbase at $44 billion and Marathon Digital at $5 billion. The company holds 846,000 BTC, trading at 1.2 times carrying value versus Marathon's 0.5 times. Management's seven-year plan targets doubling Bitcoin-per-share, funded by recent ATM issuance. However, the company carries $6.7 billion in convertible debt and reported an $8.32 billion unrealised digital asset loss in its latest quarter. Polymarket traders assign a 75% probability of MSCI index removal by year-end, presenting a technical risk to passive flows.