How Daily Dividends Could Shake Up the MicroStrategy Stock Story Strategy wants its preferred stocks to pay dividends every single day. Here's how the plan works and what it could mean for MSTR stock investors. Barchart · Sep 30
Woman, 51, Puts 100% of Her Retirement Into Bitcoin and Refuses to Spend Money on Anything Else A 51-year-old woman recently said that her entire retirement is invested in bitcoin and Strategy shares, citing faith in Michael Saylor's cryptocurrency philosophy. International Business Times UK · Sep 29
‘A Little More Orange,’ Says Saylor as He Starts Buying Bitcoin Again. Here’s Why I Don't See Much Orange in the Short Term. Strategy still trades close to the value of the Bitcoin it holds. Without the existence of a share price premium, it cannot continue buying Bitcoin so easily. Barchart · Sep 28
Michael Saylor’s Strategy buys Bitcoin again as surprise rally pushes price above $85,000 The corporate Bitcoin giant returned to buying as the cryptocurrency defied its usual September slump. Fortune · Sep 21
Billionaire Michael Saylor Says You Now Have to Put Typos in Your Messages to Prove a Human Wrote Them: ‘If You Put Errors In It, I Believe You Typed It’ As discussions about the rapidly accelerating development of AI take center stage, Michael Saylor shared a more practical remark about the advancement of the technology. Barchart · Sep 14
Michael Saylor's Strategy Stopped Buying Bitcoin For 10 Weeks. Now It's Back With A $370M Purchase. Strategy raised more than $600 million by selling common stock and also spent nearly $152 million repurchasing preferred shares as it reshapes its balance sheet. International Business Times · Aug 31
Bitcoin is back—and so is Michael Saylor’s Strategy, which made its first buy in two months The company’s return to buying follows a summer downturn spent raising cash and selling Bitcoin. Fortune · Aug 31
Strategy Stock Surges as Bitcoin Briefly Tops $80K MSTR stock jumped as Bitcoin topped $80,000 this week, fueled by Treasury bond buybacks, a short squeeze, and returning institutional demand. Barchart · Aug 30
Michael Saylor Warns Strategy Investors: 'We Have to Be Prepared to Have Difficult Years' Strategy Inc. (NASDAQ:MSTR) Executive Chairman Michael Saylor and CEO Phong Le recently defended the company’s Bitcoin-focused capital strategy, arguing that near-term pain and equity issuance are necessary. Benzinga · Aug 19
Billionaire Michael Saylor Warns Against Buying a House Because ‘Every 36 Years You Actually Pay the Cost of the House in Tax to the Government’ Michael Saylor warns that buying a house isn't a great investment, especially in areas with high property taxes. Barchart · Aug 18
Cathie Wood Endorses ‘Best Way’ to Invest in This Crypto Cycle: ‘Get as Close to the End User as Possible’ Ark Invest CEO Cathie Wood endorsed on Monday a detailed analysis by her colleague on where value is actually being captured in the cryptocurrency market. Benzinga · Aug 18
Michael Saylor Says Don't Invest in Bitcoin Unless You’ll Hold It for Over 4 Years— MSTR Chair Offers No 'Useful Wisdom' for Short-Term Traders (UPDATED) Editor’s Note: The story has been refreshed with the latest market price action. Benzinga · Aug 18
Elon Musk says AI will make money disappear. But crypto billionaire Michael Saylor says he’s wrong for one key reason: ‘We're status-oriented animals’ The billionaire Bitcoin mogul Michael Saylor says technology has already made luxuries once reserved for kings commonplace. Fortune · Aug 12
Billionaire Michael Saylor Says Skip College and 'Spend $20 a Month on an AI Subscription,' Warns Not to ‘Learn How to Do Things That AI Can Do' Saylor's recent interview offered some interesting insight into AI, among other things. Barchart · Aug 11
International Business Times · Aug 10 Michael Saylor's Strategy Sells More Bitcoin, Increasing Its Cash Stockpile To $4.6 Billion. Its Stock Is Dropping. Strategy sold nearly $109 million worth of Bitcoin and more than $650 million of its own shares last week as Michael Saylor's company continues a major shift toward managing its increasingly complex capital structure.
Fortune · Aug 10 Strategy dumps yet more Bitcoin, latest $109 million sell-off comes amid a seven-week buying hiatus The company’s fourth Bitcoin sale since June underscores its push to build cash and reassure investors.
Benzinga · Aug 9 Michael Saylor Predicts Bitcoin Will Gain 30% Annually for 20 Years Strategy (NASDAQ:MSTR) Executive Chairman Michael Saylor says artificial intelligence helped the world’s largest corporate Bitcoin (CRYPTO: BTC) holder solve a financing problem that traditional Wall Street structures could not.
International Business Times · Aug 7 Michael Saylor Just Sold Bitcoin at a Loss for the Third Time in 2026 Bitcoin trades near $64,800 on August 7, and Michael Saylor picked this exact moment to reaffirm the most audacious goal in corporate finance: making Strategy the largest company on Earth by market capitalization.
International Business Times UK · Aug 7 'Don't Buy a House': Michael Saylor Explains How ChatGPT Helped Generate $15B in Value Michael Saylor discusses how MicroStrategy used AI to generate $15 billion, urging a rethink of traditional wealth strategies amid inflation and automation. He highlights Bitcoin and AI's role in financial innovation.
Benzinga · Aug 7 Michael Saylor Says ChatGPT Helped Strategy Raise $15 Billion for Bitcoin Purchases: 'They Never Thought to Do It' Strategy Inc. (NASDAQ:MSTR) co-founder Michael Saylor said OpenAI‘s ChatGPT helped Strategy design a novel preferred stock structure that ultimately enabled it to raise roughly $15 billion to purchase additional Bitcoin (CRYPTO: BTC).
Fortune · Aug 6 Crypto billionaire Michael Saylor says he made $15 billion last year with ChatGPT—and has one rule: 'Don't try to outwork the robots' In the age of AI, the key to building wealth isn’t trying to compete with machines—it’s using them to your advantage, says billionaire Michael Saylor.
International Business Times · Aug 4 Michael Saylor's Strategy Sold Another $105 Million In Bitcoin. It Boosted Its Cash Reserve And Bought Back STRC Shares Strategy continued adjusting its capital structure last week by selling more Bitcoin, raising nearly $291 million through common stock sales and repurchasing STRC preferred shares while keeping its dividend rate unchanged.
International Business Times UK · Aug 4 Michael Saylor Defends Strategy's Sale of 1,638 BTC Worth $105M to Fund Dividends Amid Coldcard Hack Michael Saylor's Strategy sold Bitcoin worth millions to manage capital, while Saylor maintains his personal BTC holdings. Learn about the impact on Bitcoin prices and investor reactions.
Benzinga · Aug 3 American Bitcoin Q2 Earnings Loom—Eric Trump’s Bitcoin Accumulation Play Faces Investor Scrutiny American Bitcoin Corp. (NASDAQ:ABTC) is set to report its second-quarter earnings before the opening bell on Monday. Here’s what’s happening with the company and its stock.
Benzinga · Aug 3 Bitcoin, Ethereum, XRP, Dogecoin Gain After Trump Holds Off Iran Strikes: Analyst Sees 'Strong and Vital Move' by BTC if This Happens Leading cryptocurrencies edged higher on Sunday as investors weighed President Donald Trump’s remarks about a potential Iran peace agreement.