Is $MSTR over? Jason takes his victory lap. | E2216
This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.
Jason Calacanis
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Is $MSTR over? Jason takes his victory lap. | E2216

E2216 • Dec 1, 2025 • 58 mins

Michael Saylor’s Strategy play is struggling with the price of Bitcoin on a steep decline… Is his new “dollar reserve” the answer? On TWiST, we’re looking into the state of $MSTR and why Jason remains SO skeptical about this increasingly convoluted financial scheme. Is CNBC giving Michael Saylor a pass? Is that why he won’t go on “All-In”? And do investors realize that loans go BEFORE equity? We’re asking the TOUGH questions… PLUS Jason’s Four Red Flags for companies with convoluted tactics… Why S&P Global downgraded Tether, and why Jason thinks the US government waited TOO LONG to pass stablecoin regulations… Jason reacts to the NYT “hit piece” on Bestie David Sacks… we’re checking out the new Matic robot vacuum and Sunday Robotics’ Memo bot… PLUS much more of the day’s biggest tech news and stories.

Key Points

  • Stablecoins like Tether need to be regulated to ensure they meet stringent US requirements and maintain financial stability.
  • The complexity and lack of transparency in MicroStrategy's financial strategies, including their Bitcoin holdings and associated loans, have led to a significant loss in their market value.
  • Glue employees, who enhance team performance through high emotional intelligence and proactivity, are crucial for building a resilient and supportive company culture.
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