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MicroStrategy's $64 Billion Bitcoin Investment: Is It Paying Off?

1.4K views· 33 likes· 5:35· Jun 5, 2026

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Michael Saylor famously said sell your kidneys before you sell your Bitcoin. Strategy just sold Bitcoin for the first time to satisfy financial obligations. The amount is tiny at 32 coins out of 843,000 total. But the behavior is a complete shift and the market is noticing. Strategy spent $64 billion accumulating Bitcoin now worth roughly $53 billion at current prices, an $11 billion deficit. Saylor changed his language from never sell to net accumulator. Options activity followed in near-term puts and in October at the 50 strike, more than 60 percent below where the stock is trading. Chris Vecchio and Jermal Chandler break down whether this is a signal or just noise. 📊 tastylive: https://www.tastylive.com/ 📰 Get Tom's pre-market analysis every morning: https://www.tastylive.com/newsletters 📘 FREE Options Strategy Guide: https://tinyurl.com/bp9ms763 📱 Follow tastylive on X: https://x.com/tastyliveshow Chapters 0:00 Strategy sells Bitcoin for the first time 1:00 32 Bitcoin to satisfy financial obligations 2:00 Near-term puts in June 12th and June 18th 3:00 October 50 strike puts: the standout trade 4:00 $64 billion spent, $53 billion worth today 5:00 From never sell to net accumulator 6:00 Is this signal or noise? #MicroStrategy #Bitcoin #Saylor #MSTR #SignalVsNoise #tastylive #CryptoOptions #OptionsTrading tastylive is a real financial network, producing hours of live programming every day. Follow along as our experts navigate the markets, provide actionable trading insights, and teach you how to trade. With over 120 original segments, and over 25 personalities, we'll help you take your trading to the next level, whether you are new to trading or a seasoned veteran. tastylive content is created, produced, and provided solely by tastylive, Inc. ("tastylive") and is for informational and educational purposes only. It is not, nor is it intended to be, trading or investment advice or a recommendation that any security, futures contract, digital asset, other product, transaction, or investment strategy is suitable for any person. Trading securities, futures products, and digital assets involve risk and may result in a loss greater than the original amount invested. Investment information provided may not be appropriate for all investors and is provided without respect to individual investor financial sophistication, financial situation, investing time horizon or risk tolerance. Options, futures, and futures options are not suitable for all investors. Prior to trading securities, options, futures, or futures options, please read all applicable risk disclosures, including, but not limited to, the Characteristics and Risks of Standardized Options Disclosure and the Futures and Exchange Traded Options Risk Disclosure Statement found at https://tastytrade.com/disclosures/. Past performance is not indicative of future results. Performance is not presented net of all commissions, fees, and expenses. Multi-leg option strategies incur higher transaction costs than single leg trades as they involve multiple commission charges. Examples provided are for illustrative, informational, and educational purposes only and are not intended to be reflective of results you can expect to achieve. Supporting documentation for any claims, including claims made on behalf of options programs), comparisons, statistics, or other technical data, if applicable, will be supplied upon request. tastylive, through its content, financial programming or otherwise, does not provide investment or financial advice or make investment recommendations. tastylive is not a licensed financial adviser, registered investment adviser, or a registered broker-dealer.

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