SkyBridge Capital founder Anthony Scaramucci is breaking down the mechanics—and the market risks—behind Strategy Inc.'s (NASDAQ:MSTR) high-yielding perpetual securities, calling the dividend play a potentially lucrative move for steadfast Bitcoin (CRYPTO: BTC) believers.
The 11% Yield Strategy
During a recent episode of the All Things Markets podcast, Scaramucci and Galaxy Digital Inc. (NASDAQ:GLXY) CEO Mike Novogratz analyzed MSTR’s strategy of offering a yield-bearing security.
Scaramucci noted that investors putting money into Michael Saylor's company, earlier known as MicroStrategy, can receive four quarterly dividend payments equivalent to roughly an 11.5% yield.
While emphasizing the attractiveness of the trade, Scaramucci made sure to clarify his firm’s exact position to listeners. “I’m a huge fan of his and obviously SkyBridge owns a lot of Bitcoin. We don’t own any of that security, but I just wanted to disclose that to people,” Scaramucci stated.
He added that as long as Bitcoin holds its muster and Strategy trades at a premium—or at least not at a huge discount—Saylor will be able to sustain the impressive payouts.
Leverage And The ‘Big Cushion’
However, the outsized yield does not come without inherent structural risks. Novogratz warned that the setup relies on corporate debt.
“It’s leverage on strategy,” Novogratz explained, noting that while Saylor currently enjoys a “big cushion” due to his massive cryptocurrency corpus, a severe drop in Bitcoin’s price would inevitably reduce that critical safety net.
If Bitcoin were to plummet to $30,000, investors might naturally worry about losing their principal. However, Novogratz clarified that Saylor has structured the perpetual offering quite favorably for Strategy.
In simple terms, a perpetual offering of bonds has no maturity date, meaning you can collect a continuous yield but forfeit the right to ever demand your initial investment back.
Understanding The Perpetual Risk
Because the security is a perpetual asset, Novogratz pointed out that investors have “no right to take the money back.”
Furthermore, Saylor theoretically holds the right to halt the dividend payments if necessary, though doing so would immediately cause the security to trade at a severe discount.
Ultimately, Novogratz believes the trade remains relatively solid for those willing to accept the specific market parameters. “In all likelihood, you’ll get your 11 and a half percent,” Novogratz concluded. “You’re just selling a tail, and it’s a pretty out-of-the-money tail you’re selling.”
Strategy Underperforms In 2026
MSTR has declined 19.20% year-to-date, outpacing the losses in the Nasdaq Composite index, which fell 6.00% during the same period. It was lower by 63.72% in the last six months and 59.88% over the year.
The stock closed Wednesday 1.64% higher at $122.78 apiece, and it was lower by 2.64% in premarket on Thursday. Benzinga’s Edge Stock Rankings indicate that MSTR maintains a weak price trend in the short, medium, and long terms.
Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.
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