Saylor Created MicroStrategy’s STRC Stock with AI, and Now It Crashed Below $100

MicroStrategy’s biggest Bitcoin financing tool is under pressure. Strategy’s STRC preferred stock fell well below its intended $100 level this week, raising fresh questions about the company’s complex plan to keep buying Bitcoin through Wall Street-style securities. 

The selloff drew extra attention because Saylor has linked Strategy’s new preferred-stock products to AI-assisted design.

“When we did STRC, I did it all with AI. I couldn’t have done it myself. I literally sat and used AI, went back and forth for hours,” Saylor said in an interview. 

STRC, formally known as Strategy’s Variable Rate Series A Perpetual Stretch Preferred Stock, was built to trade close to $100. Strategy can adjust its dividend rate each month to help support that target.

That design is now being tested.

STRC traded near the high-$80s after falling as low as the low-$80s, well below the level Strategy wants it to hold. 

For a product sold as a relatively stable, high-yield preferred stock, that drop has become a major signal for investors.

The AI Angle Turns a Selloff Into a Meme

The crash became more sensational because of Saylor’s comments about AI.

Saylor has said Strategy used artificial intelligence to help design some of its preferred-stock products. Critics are now mocking STRC as an “AI-designed” security that is breaking under market pressure.

The line is catchy, but the reality is more complicated. AI likely helped with modelling, structure, or product design. The security itself still went through bankers, lawyers, executives, and market approval.

Still, the optics are bad. STRC was pitched as financial engineering for the Bitcoin era. Its drop below $100 makes that engineering look less stable than advertised.

STRC is down 15% in two weeks.Saylor said he "designed it with ChatGPT." pic.twitter.com/GepEwnmbUx

— Zack Voell (@zackvoell) June 18, 2026

What STRC Actually Is

STRC is not Bitcoin or a stablecoin, but it’s not a normal company share either.

It is a preferred stock issued by Strategy, the company formerly known as MicroStrategy. Preferred stocks usually sit between common shares and debt. Investors buy them mainly for income.

STRC pays a high dividend. Strategy can raise or lower that dividend monthly to try to keep the stock trading around $100.

That is the core mechanism. If STRC falls too far below $100, the market expects Strategy to raise the dividend to make it more attractive.

The financial house of cards @Saylor built is collapsing. $MSTR's per-share discount to its Bitcoin holdings is soaring, $STRC is tanking, and Bitcoin itself is breaking down, taking the rest of crypto down with it. Soon Saylor will trade in his orange tie for an orange jumpsuit.

— Peter Schiff (@PeterSchiff) June 18, 2026

Why the Drop Matters

A higher dividend means MicroStrategy must pay more to investors.

That increases the cost of raising capital. It also makes future STRC issuance harder. If investors no longer believe STRC can hold near $100, Strategy may have to offer even higher yields to attract buyers.

For Saylor, that matters because Strategy has used securities like STRC to fund its Bitcoin strategy. The company raises money from capital markets and uses part of that money to buy more Bitcoin.

When that machine works, Strategy can keep expanding its Bitcoin holdings without selling much common stock at unattractive levels.

When it weakens, the choices get harder.

Will MicroStrategy Have to Sell More Bitcoin?

There is no confirmed sign that Strategy will have to sell Bitcoin again because of STRC.

The concern is about pressure, not an immediate forced sale.

If STRC keeps falling, Strategy may need to raise the dividend again. If dividend costs rise, the company needs reliable cash flow or fresh capital to keep paying investors.

That could lead to more common stock issuance, which would dilute shareholders. It could also reduce Strategy’s ability to buy more Bitcoin. 

In a more stressed scenario, investors worry the company may eventually face pressure to sell some Bitcoin to meet obligations or defend its balance sheet.

That would hit the core narrative around Saylor’s strategy. Strategy has built its identity around accumulating Bitcoin, not selling it.