Podcast Alpha

Podcast Alpha

Michael Saylor on Diary Of A CEO - How He Used AI For STRK

Podcast Alpha's avatar
Podcast Alpha
Aug 08, 2026
∙ Paid

Michael Saylor says AI helped him raise $15 billion by designing a financial instrument that had never existed before.

  • Strategy holds 847,000 BTC (about 4% of supply) and used ChatGPT to design STRK, a first-of-its-kind variable-dividend preferred stock that raised $15 billion Michael @ 34:09.

  • Saylor forecasts 30% annual Bitcoin appreciation for 20 years, citing a 33% six-year return versus 12% for gold and 15% for the S&P 500 Michael @ 90:44.

  • Saylor sold Bitcoin near $59,000-$60,000 to break a short-seller “doom loop” narrative that Strategy could never sell without crashing Bitcoin and its own stock Michael @ 86:45.

  • Saylor claims Strategy stays overcollateralized even if Bitcoin fell to $5,000, an unverified insider claim worth checking against filings Michael @ 84:39.


This breakdown is for paid subscribers. Below: the STRK mechanics Saylor says AI designed, the doom-loop math behind the Bitcoin sale, and the balance-sheet numbers worth checking against Strategy’s filings. Join to get full access.

User's avatar

Continue reading this post for free, courtesy of Podcast Alpha.

Or purchase a paid subscription.
© 2026 Podcast Alpha · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture