Short seller Jim Chanos calls out Michael Saylor’s MicroStrategy originally appeared on TheStreet .
A new fiasco is emerging on Wall Street between famous short-seller Jim Chanos and Bitcoin maximalist Michael Saylor, executive chairman of Strategy (formerly MicroStrategy).
Chanos has focused on the company's high market premium relative to its Bitcoin holdings, suggesting that traders should consider shorting the stock and buying Bitcoin directly. But Saylor is not taking it lying down.
In a Bloomberg TV interview on Tuesday, he crudely dismissed Chanos's thesis, saying, "I don't think he understands what our business model is," referring to Chanos.
"We're not a passive holding company or trust. We're an operator; we're not a passive financial innovator."
Chanos' call-out focused on the company's high premium to net and its historic premium, at times exceeding 200%, to its Bitcoin reserves, which he saw as an arbitrage opportunity.
In contrast, Saylor defended the use of the Strategy's structure, arguing that it provided tremendous financial leverage. "We're actually the largest issuer of Bitcoin-backed credit instruments in the world," he said.
The company has raised nearly $1 billion through high-yield preferred stock backed by Bitcoin — STRK, STRF, and STRD — with STRD commencing trading on Nasdaq today.
Saylor gets back at Jim Chanos
Saylor stated that these instruments enable Strategy to capitalize on the delta between low-cost capital (a 10% yield) and Bitcoin's long-term growth rate (since mid-2020 at a 57% compound annual growth rate), thereby creating an effective 47% return spread for its shareholders.
"If the stock trades at a weak premium, we're just going to sell the preferred and buy back common shares," Saylor warned. "If the stock rallies, [Chanos] is going to get liquidated and wiped out."
Chanos gets back with a blunt response
Chanos didn't immediately reply to Saylor's comments. However, on June 10, Chanos took to X and said :
"This is, of course, complete financial gibberish. Mr. Saylor wants you to value his business based not only on the net value of his Bitcoin holdings (NAV) at market, but additionally with a multiple on the change in that NAV! Because now he can leverage his balance sheet, lol."
He likened it to saying a house worth $500,000 is worth $1.5 million, because its value had increased by $50,000, and applied a multiple of 20 times that gain.
Chanos also stated that Saylor's so-called "infinite money glitch" had a minimal impact on Strategy's market-to-net-asset-value (mNAV), which had remained flat at approximately 1.8x (i.e., unchanged since the company began aggressively accumulating Bitcoin in 2020).
As of June 11, Strategy's mNAV stands at 1.86, unchanged from the previous month.
Short seller Jim Chanos calls out Michael Saylor’s MicroStrategy first appeared on TheStreet on Jun 11, 2025
This story was originally reported by TheStreet on Jun 11, 2025, where it first appeared.