Strategy is Trapped & in Crisis — "It's Basically a Hedge Fund Now" | Jeff Dorman & Matt Walsh

Michael Saylor’s Strategy bought itself time, but did it actually solve the problem? David sits down with Jeff Dorman and Matt Walsh to unpack Strategy’s increasingly complex capital structure, why $STRC and MSTR are now fighting for oxygen, whether Saylor may need to sell Bitcoin, and why the company is starting to look less like a levered BTC play and more like an actively managed hedge fund. --- 📣OKX | THE NEW MONEY APP https://app.okx.com/en-us/join/usbankless --- BANKLESS SPONSOR TOOLS: 🔮POLYMARKET | #1 PREDICTION MARKET https://bankless.cc/polymarket-podcast 📊BITGET | TOKENIZED STOCKS 2.0 https://bankless.cc/bitget-stocks 🎯THE DEFI REPORT | ONCHAIN INSIGHTS https://thedefireport.io/bankless 👑BANKLESS PREMIUM | AD-FREE & BONUS EPISODES https://bankless.cc/spotify-premium --- TIMESTAMPS 0:00 Intro 2:30 Can Stretch Return to 100? 4:00 Explaining the New Framework 4:43 Can the Capital Stack Coexist? 6:39 Refunding the Converts 8:32 MNAV Near the Breaking Point 11:15 Option Value or Investor Betrayal 15:37 Legal Risk and Retail Exposure 19:52 Buying Time, Not Solving It 22:20 Scenario Odds After the Pivot 24:54 Sell Bitcoin or Wait 28:59 M&A as a New Path 34:13 Temporary Relief, Future Crash 36:21 Slow Bleed, Not Bankruptcy 40:58 Bitcoin Needs a Bigger Narrative 46:56 Would Jeff Buy Stretch? 48:26 Is the Model Actually Genius? 52:09 Closing & Disclaimers --- RESOURCES Matt Walsh https://x.com/MattWalshInBos Jeff Dorman https://x.com/jdorman81 --- Not financial or tax advice. See our investment disclosures here: https://www.bankless.com/disclosures