Why MSTR Should Have Sold $2 Billion Instead of $2 Million of Bitcoin

Jeff Dorman on why Strategy's four stakeholder classes are all losing, and why Saylor should have sold $2B of Bitcoin at once instead of $2.5M. ======================================================== Thank you to our sponsor! Fidelity: Explore opportunities at ======================================================== Strategy’s late-May Bitcoin sale has turned a long-running investor concern into a sharper question: how sustainable is the company’s capital structure if its Bitcoin accumulation strategy now comes with large cash obligations? Jeff Dorman, chief investment officer at Arca, joins Laura Shin to discuss why the sale changed his view of the risks around Strategy. After months of pushing back on fears of forced selling, Dorman says the company’s preferred-share financing has altered the analysis. He points to roughly $15 billion in preferred shares carrying 10% to 12% dividend rates, which he estimates could mean about $1.7 billion in annual cash obligations for a company without operating revenue. Dorman also breaks down the stakeholder groups shaping Strategy’s choices, the tradeoffs each path may create, and the Polymarket dispute over whether Strategy sold Bitcoin in May. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained Guests: ⁠⁠⁠⁠⁠⁠⁠⁠⁠Jeff Dorman - Chief Investment Officer at Arca - Learn more about your ad choices. Visit megaphone.fm/adchoices

You can listen to Why MSTR Should Have Sold $2 Billion Instead of $2 Million of Bitcoin online on Radio and Podcast. Open the player on this page to stream the available audio.

Why MSTR Should Have Sold $2 Billion Instead of $2 Million of Bitcoin is an episode from Unchained: Big Ideas From The Worlds Of Blockchain And Cryptocurrency by Laura Shin.

This episode is 35:01 long.

This episode was published on Jun 5, 2026.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Unchained: Big Ideas From The Worlds Of Blockchain And Cryptocurrency when more episodes are available from the podcast feed.