Michael Saylor claimed he used AI to build part of Strategy. So we turned to AI to see whether it believed STRC could recover.
Share
Key Takeaways
Michael Saylor admitted to using ChatGPT to build parts of Strategy.
STRC has fallen well below its intended $100 value.
ChatGPT, Grok and Claude all said STRC could recover, but only under certain circumstances.
Shares of Strategy have slid sharply this week as pressure intensified on the company’s Bitcoin acquisition model following a collapse in its Stretch preferred stock, STRC.
The fall comes as resurfaced comments from Executive Chairman Michael Saylor revealed that ChatGPT helped shape parts of the security’s design.
As STRC trades well below its $100 target, critics have raised questions about the sustainability of the financing structure that has funded Strategy’s aggressive Bitcoin accumulation so far.
Saylor’s remarks prompted an obvious follow-up question.
If AI helped design parts of the structure, what does it think of its chances now?
To find out, we asked three leading AI models — ChatGPT, Claude and Grok — whether STRC can recover to its $100 target value and what Strategy must do to restore investor confidence.
Try Our Recommended Crypto Exchanges
Sponsored
Disclosure
We sometimes use affiliate links in our content, when clicking on those we might receive a commission at no extra cost to you. By using this website you agree to our terms and conditions and privacy policy.
The controversy reignited after users on X circulated clips from a May interview with CoinDesk in which Saylor described using AI extensively while developing elements of Strategy’s preferred stock offerings.
“When we did Stretch, you know, I designed all these with AI. You know, I couldn’t have done it myself,” Saylor said.
“I used artificial intelligence, and I went back and forth with the AI for a few hours.”
According to Saylor, he challenged the AI on various structural features and tested whether unconventional ideas would be legal.
“And at some point, I said, well, I want a monthly preferred and I wanted it to be stable at a hundred,” he explained.
Saylor said the AI responded: “No one in the history of the world has ever done this, but it’s totally legal, and it’s totally reasonable.”
Why STRC’s Fall Matters
STRC’s decline has become a central concern for investors because the preferred stock plays a key role in Strategy’s broader bitcoin acquisition machine.
That drop carries consequences beyond paper losses for holders.
Strategy has relied heavily on issuing preferred securities and other capital instruments to raise cash for additional bitcoin purchases.
When preferred shares trade materially below their intended value, issuing new shares becomes significantly less attractive and can limit the company’s ability to raise fresh capital.
Schiff Escalates Attacks On Strategy
Among the most vocal critics has been economist and longtime Bitcoin skeptic Peter Schiff.
Schiff warned that falling STRC prices could create a self-reinforcing cycle that becomes increasingly difficult to reverse.
“If Saylor raises the yield to 13%, he will have to sell even more MSTR at bigger discounts to fund it. If he doesn’t raise the yield, the STRC price will keep falling,” Schiff wrote on X on Wednesday.
Schiff had previously argued that investors would begin to question Strategy’s willingness and ability to maintain dividend payments if the preferred stock continued to weaken.
“The only way to stop the death spiral is for MSTR to cancel the dividend. Then STRC crashes, taking MSTR and BTC with it,” he wrote in April.
Following Thursday’s selloff, Schiff intensified his criticism.
“The financial house of cards Saylor built is collapsing,” Schiff wrote.
“MSTR’s per-share discount to its Bitcoin holdings is soaring, STRC is tanking, and Bitcoin itself is breaking down.”
In a separate post, Schiff criticized financial media coverage of Strategy’s preferred stock decline, accusing CNBC of ignoring mounting problems surrounding the company.
We Asked ChatGPT, Claude And Grok Whether STRC Can Recover
We asked three leading AI models — ChatGPT, Claude, and Grok — whether Michael Saylor’s STRC can recover to its $100 target value and what Strategy must do to restore investor confidence.
ChatGPT’s View
ChatGPT said a return to $100 remains possible but would likely require a combination of stronger market confidence, sustained dividend coverage, and a recovery in Bitcoin prices.
“The fastest path back to par would be restoring investor confidence that dividends can be maintained without relying on asset sales,” ChatGPT said.
The model argued that investors will closely watch whether Strategy can continue to meet its funding obligations through capital markets rather than by selling Bitcoin.
“If Bitcoin stabilizes and demand for income-focused securities improves, STRC could gradually move back toward $100,” it added.
However, ChatGPT cautioned that confidence could deteriorate further if additional Bitcoin sales become necessary.
Grok’s View
Grok took a more skeptical stance.
“Can STRC get back to $100? Maybe, but it’s going to be extremely tough,” the model said.
According to Grok, much of STRC’s future depends on Bitcoin’s performance and investors’ willingness to continue financing Strategy’s broader treasury strategy.
“The market is basically asking whether the engine funding the Bitcoin-buying machine still works,” Grok said.
The model argued that a sustained Bitcoin rally would likely be the most effective catalyst for recovery.
It added that a prolonged weakness could place additional pressure on both STRC and MSTR.
Claude’s View
Claude offered the most measured assessment.
The AI said preferred securities often recover from discounts to par value, but only when investors regain confidence in the issuer’s ability to meet long-term obligations.
“Recovery is possible, but it requires credibility more than creativity,” Claude said.
The model highlighted balance-sheet strength and access to capital markets as the key variables investors will monitor.
“Markets need evidence that the structure can function during adverse conditions, not just during periods of rising bitcoin prices,” Claude added.
Asked what Strategy must do to survive, Claude said the company will likely need to demonstrate that its financing model remains viable even if Bitcoin continues to decline.
Kurt Robson is a London-based reporter at CCN, specialising in the fast-moving worlds of crypto and emerging technology. He began his career covering local news in Cornwall after graduating from Falmouth University with First Class Honours in Journalism. There, he cut his teeth on everything from council meetings to missing swans.
He quickly rose through the ranks to become a frontline journalist at several of the UK’s leading national newspapers. Over the years, he has interviewed musicians and celebrities, reported from courtrooms and crime scenes, and secured multiple front-page exclusives.
Following the upheaval of the COVID-19 pandemic, Kurt shifted his focus to technology journalism—just ahead of the AI boom. With a natural curiosity and a trained eye for emerging trends, he has found a new rhythm in reporting on innovation.
At CCN, Kurt's work focuses on the cutting edge of crypto, blockchain, AI, and the evolving digital world. Drawing on his background in people-first reporting and his deep interest in disruptive tech, Kurt delivers stories that are insightful, entertaining, and human-centric.
