Vinny Lingham, co-founder of Praxos Capital and a figure once called “the Oracle” in crypto circles, recently revisited a bold prediction he made two years ago. Appearing on Laura Shin’s Unchained podcast on June 25, 2026, Lingham explained why he still thinks Michael Saylor’s actions could hurt bitcoin more than FTX’s collapse.
Lingham first published this warning on X in October 2024. At the time, MicroStrategy – now known as Strategy – was trading near its all-time high of $473.83. The prediction sparked much ridicule. But as of this week, MSTR has fallen more than 80% from that high, hovering around $90.70. Lingham noted that what seemed like an unpopular opinion 18 months ago now raises serious questions.
The “Saylor Plan” and complex capital structures
Lingham doesn’t outright call the strategy a Ponzi scheme. Instead, he coined his own term: a “Saylor Plan.” It describes a capital structure based on debt and multiple layers of preferred securities. “He issued STRC, STRD, STRK…and several others. When one offering stopped working, he simply brought in another,” Lingham said.
One of these preferred stocks, STRC, fell sharply. It closed at $75.69 after falling below $74 earlier this week. Lingham doesn’t expect him to recover. “I don’t believe STRC will ever go back to $100,” he said, adding that he would bet it never goes back to par again.
Zugzwang and the end of chess
Strategy recently raised $335 million by selling 2.7 million shares of common stock. About $300 million was spent building cash reserves, which now stand at about $1.4 billion. This cash is expected to cover preferred dividend obligations for approximately 10 months. But Lingham says the market still responded by selling MSTR and STRC.
He believes Strategy’s move to fortnightly dividend payments has made the situation worse. More frequent payments mean less time for management to react when conditions deteriorate. Each cycle tightens pressure on liquidity reserves.
Lingham described Saylor’s situation using a chess term. “Michael now plays in what we call zugzwang in chess,” he said. “Every move he has is a losing move. If he increases the dividend yield, he shortens his cash flow. If he issues more shares, he further dilutes common shareholders.”
The $6.7 trillion debt problem
During the podcast, Shin highlighted concerns raised by Matt Walsh of Castle Island Ventures. Strategy has approximately $6.7 billion in convertible notes outstanding, many of which come with put rights that allow holders to demand cash repayment if the notes are not converted or refinanced. Walsh estimated that to cover the first three maturities until June 2028, at a bitcoin price of around $60,700, one would need to sell around 74,000 BTC. To cover the entire program, approximately 111,000 bitcoins would be required.
Lingham responded by saying the market was already pricing in this risk. “The strategy only sold 32 bitcoins and the market reacted negatively,” he said. “Imagine what would happen if the company ultimately had to sell tens of thousands of bitcoins.”
The reflective loop in reverse
Lingham argues that the aggressive accumulation of the strategy created a self-reinforcing cycle that worked on the way up. The company bought Bitcoin, driving up prices, which increased the value of MSTR, allowing it to issue more shares and buy more Bitcoin. Today, he says the cycle is reversed.
“Once Strategy stops being the largest buyer of Bitcoin, selling pressure starts to outweigh buying pressure,” he explained. “Liquidity is disappearing. The biggest source of demand is gone.”
He also noted that Strategy’s mNAV sits around 1.06. Historically, this is a level at which similar investment vehicles trade at a discount. Lingham thinks a value closer to 0.90 would make more sense given the circumstances.
What comes next
Lingham told Shin that the healthiest outcome would be for Saylor to stop buying Bitcoin, stop issuing new shares, preserve its liquidity and wait for a recovery in the market cycle. But he doesn’t expect that to happen. “I don’t think he will admit that the strategy needs to change,” Lingham said. “I think pride plays a big role here.”
