Sometimes what insiders don't do tells you more than what they do. For 3.5 years, Strategy Inc. (MSTR) director Carl Rickertsen followed a simple playbook: receive stock options as compensation, exercise them, sell the shares immediately, repeat. Nineteen consecutive SEC filings documented this pattern without a single purchase.
That streak just ended in dramatic fashion. Rickertsen bought 5,000 shares for $779,395 on Monday, paying an average of $155.88 per share after the stock collapsed 68% from its $543 November high.
When the Serial Seller Becomes a Buyer
The last time Rickertsen actually purchased MSTR stock was June 2022. Since then, he reported owning $0 worth of shares between compensation grants because he sold everything the moment he got it. Over those years, he made tens of millions selling MSTR.
His Monday purchase wasn't just any buy. He almost perfectly caught the bottom of the day's $154.69 to $163.82 trading range. That's not beginner's luck. Rickertsen has served on Strategy's board since 2002, back when the company was still called MicroStrategy. He's lived through every cycle this business has seen and understands it intimately.
His day job adds context here. Rickertsen is a managing partner at two private equity firms and serves as trustee for two investment companies. He literally spends his professional life valuing distressed assets and hunting for opportunities when prices get crushed.
The Math That Changed Everything
So what flipped? The premium collapsed. In November 2024, investors were paying 3.4 times what Strategy's Bitcoin (BTC) holdings were actually worth. They valued MSTR at 240% above the company's BTC stash.
Then reality arrived. Trump pivoted from Bitcoin evangelism to promoting crypto more broadly, and BTC went sideways. MSTR crashed from $543 to around $169, and suddenly the stock trades much closer to the actual value of its Bitcoin.
Strategy now holds $67 billion in enterprise value against $64 billion worth of Bitcoin. That 240% premium evaporated to almost nothing.
For a director who's been selling for years because the valuation made no sense, that's the kind of reset that changes the equation. Monday's purchase doesn't guarantee the stock bottomed, but it signals that someone with deep company knowledge believes the risk-reward profile fundamentally shifted after the 68% decline.
Testing Support After the Crash
MSTR closed Tuesday up 6.63% and trades up 2.35% in premarket around $177. The stock is now testing the $177-$181 zone after bouncing from support levels.
The two-day rally looks encouraging, but the real test comes at $193-$200. MSTR needs to reclaim that range to signal an actual reversal rather than just another failed bounce attempt. Breaking above $193 would mark the first meaningful momentum shift, potentially opening a path toward $220-$237, though steep resistance waits at those levels.
On the downside, support holds at $165, then $155. If the stock loses $165, it likely triggers another test of the $155-$165 zone. Below that, downside targets sit at $150 and $135.
The technical setup matters, but so does the timing of Rickertsen's purchase. Directors file these forms because markets pay attention when longtime insiders suddenly reverse course. After 19 straight selling reports, one buy stands out. Whether it marks the bottom or just a pause in the decline, someone who knows this company better than almost anyone just decided the price finally made sense.