Lawrence Lepard, a longtime bitcoin investor and advocate, laid out one of the most aggressive bull cases for Strategy (NASDAQ:MSTR | MSTR Price Prediction) on a recent appearance on Thoughtful Money with Adam Taggart. Lepard says he is buying shares both for his fund and personally, and his target price is striking: “I think it’s a $1,000 stock within a few years.”

MSTR last traded around $127.69 after falling 35.53% over the past month and 67.34% over the past year, alongside a sharp pullback in Bitcoin, which is down 21.27% over the past month to about $63,495.

The $1,000 Call and the Leverage Thesis

Lepard’s idea is that MSTR is a leveraged proxy on Bitcoin. Strategy borrows in dollars, issues equity and preferred stock, and channels the proceeds into Bitcoin. That structure amplifies Bitcoin’s moves in both directions, which is why MSTR has historically outrun Bitcoin in rallies and undercut it in drawdowns. “I’m very, very bullish on MicroStrategy,” Lepard said, framing Strategy stock as the most concentrated way to express his view that Bitcoin annual returns continue in the 30-40% range.

The Weimar Germany Analogy

Lepard compares Michael Saylor’s strategy of borrowing in fiat currency to buy bitcoin to that of a Weimar-era investor who borrowed money to buy industrial businesses. As the value of the German currency collapsed, investors who had borrowed money to purchase hard assets such as businesses, real estate, or commodities often saw their assets rise in value while their debt became easier to repay in increasingly devalued currency.

In an inflationary environment, debt denominated in a depreciating currency becomes easier to service over time, while the hard asset purchased with that debt appreciates in real terms. Lepard’s broader macro view is that, “the monetary system we’ve constructed is fatally flawed.” This is his foundation for treating Bitcoin as digital gold and MSTR as a vehicle to compound it.

The Stretch Preferred and Financial Engineering

The newest piece of Saylor’s financing stack is the Stretch preferred stock. It pays an 11.5% dividend, with proceeds generated from the preferred stock used to buy more bitcoin. “To me, it’s an intelligent corporate financial engineering bet,” he said.

The strategy is straightforward: raise capital through high-yield preferred stock offerings, invest the proceeds into Bitcoin, and rely on Bitcoin’s appreciation to more than cover the dividend payments. The challenge is that an 11.5% dividend is a fixed obligation that must be paid regardless of whether Bitcoin is trading at $100,000 or $40,000.

Saylor Becomes the “Richest Man in the World” or Bankrupt

Lepard is candid that the outcome for Strategy is binary. On the upside, he believes Saylor “will end up probably the richest man in the world, but it’ll probably take 20 years for that to happen.” On the downside, if Bitcoin fails, Saylor “is going to go bankrupt faster than anybody else.” His conviction is unambiguous: “I kind of feel like we’ve won this game now. It’s become pretty obvious we’ve won this game.”

Prediction markets paint a more measured picture. Polymarket traders assign only an 8% probability of a MicroStrategy margin call in 2026, but just a 36% probability that the company reaches 1 million BTC by year-end. Sell-side analysts maintain a consensus target of $351.54, with 14 buy ratings and 1 hold, well below Lepard’s $1,000 figure but well above today’s price.

Lepard’s MSTR thesis is among the most aggressive expressions of Bitcoin bullishness in public markets. The same financial engineering that makes the $1,000 scenario possible, layered preferreds and dollar-denominated debt funding bitcoin purchases, also stacks fixed obligations that get harder to meet if Bitcoin keeps sliding. MSTR is a leveraged, binary-outcome way to play bitcoin rather than a substitute for owning it directly.