Strategy Director Buys MSTR For First Time In 3.5 Years-Here's Why That Matters

Strategy Inc. (NASDAQ:MSTR) director Carl Rickertsen recently broke a 3.5-year pattern of only selling stock, buying 5,000 shares for $779,395 on Monday after the stock crashed 68% from its $543 November peak.

Director Flips From Seller To Buyer After 68% Crash

Rickertsen hadn’t purchased MSTR since June 2022. 

Over the past three and a half years, he filed 19 separate SEC forms showing nothing but stock sales. 

His pattern was predictable: get stock options as compensation, exercise them, sell the shares the same day.

Monday’s purchase marks a complete reversal. He bought at an average price of $155.88—almost perfectly timing the bottom of Monday’s $154.69 to $163.82 trading range.

The timing matters because Rickertsen has been a Strategy board member since 2002 when the company was still called MicroStrategy. 

He’s seen every cycle the company has been through and knows the business intimately.

Why He Stopped Selling And Started Buying

The key is what changed: MSTR’s valuation relative to its Bitcoin (CRYPTO: BTC) holdings collapsed. 

In November 2024, investors were paying 3.4 times more than Strategy’s Bitcoin was actually worth. They valued MSTR at 240% above the company’s BTC holdings.

That premium evaporated. Trump shifted from specifically promoting Bitcoin to promoting crypto broadly, and BTC went sideways. 

MSTR crashed from $543 to around $169, and suddenly the stock trades much closer to what its Bitcoin is actually worth.

Strategy holds $67 billion in enterprise value against $64 billion worth of Bitcoin. The premium shrunk from 240% down to almost nothing.

What Makes This Director Different

Rickertsen isn’t just any insider. He’s a managing partner at two private equity firms and serves as trustee for two investment companies. 

His day job is literally valuing distressed assets and finding opportunities when things get beaten down.

For years, he reported owning $0 worth of MSTR shares between compensation grants because he sold everything immediately. 

He made tens of millions selling MSTR stock over the past 3.5 years.

Now he’s putting his own money in for the first time since 2022. That’s not a guarantee the stock bottomed, but it shows someone with deep company knowledge believes the risk-reward flipped after the 68% decline.

Stock Attempts Bounce After 68% Crash

MSTR closed Tuesday up 6.63%, and trades up 2.35% in premarket at approximately $177.

The stock is now testing the $177-$181 zone after bouncing from support.

The two-day rally from support suggests potential short-term relief, but MSTR needs to reclaim $193-$200 to signal a genuine reversal rather than another failed bounce.

Breaking above $193 would be the first meaningful shift in momentum, opening a path toward $220-$237. However, steep resistance sits at these levels.

Support holds at $165, then $155. Losing $165 would likely trigger another test of the $155-$165 zone, with downside targets at $150 and $135 if that breaks.

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