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.

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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

Jeff Dorman

Not financial or tax advice. See our investment disclosures here: