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

Unchained

Laura Shin

Tech News, Business News, News

4.6 • 1.3K Ratings

🗓️ 5 June 2026

⏱️ 35 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 https://crypto.fidelitycareers.com ======================================================== 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 - https://x.com/jdorman81 Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	So, you know, you're just in a weird situation now where, again, it's not like default is imminent
0:05.5	here, but this flywheel that he's created over six years is just slowly dying.
0:10.9	And he's put too many pieces in the puzzle that can't be serviced at the same time.
0:16.4	Hi, everyone. Welcome to Unchained. You're no hype resource for all things crypto. I'm your host,
0:21.1	Laura Shin. Thanks for joining this live stream. Fidelity has been investing in blockchain since 2014.
0:27.4	They're not wondering if digital assets will shape the future. They're hiring the talent to help ensure they do.
0:33.2	Explore opportunities today at crypto.fidelity careers.com.
0:38.0	Fidelity is an equal opportunity employer.
0:41.4	Today's topic is strategy's dilemma and why it's begun selling some Bitcoin.
0:46.6	Here to discuss is Jeff Dorman, chief investment officer at ARCA.
0:50.3	Welcome, Jeff.
0:51.9	Hi, Laura. Thanks for having me.
0:53.8	And as always, quick compliance. The views I express are my own and are provided for informational purposes only. Nothing I say should be construed as investment advice.
1:02.9	You wrote a tweet last week that was somewhat prophetic. You said, quote, the MSTR story has gotten so out of hand.
1:10.9	Excuse me. This is the first time that MSTR, BTC, and preff holders are really in a bind.
1:17.0	Someone is going to lose badly here, and it will happen in the next four months.
1:21.7	And then, of course, we heard on Monday that Indeed Strategy had sold 32 Bitcoin at the end of May for $2.5 million. And you've
1:31.3	written on your blog about how you used to be a fan of strategy and would defend it against
1:35.4	people's concerns that it would someday have to sell Bitcoin. But obviously now your tune has
1:41.0	changed and you ascribe that to their new capital structure.
1:45.5	So what changed in the structure and why do you think it's a problem?
1:50.2	Sure. Yeah, I guess I should have said within the next four days, not necessarily the next four
	...

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