Strategy Director Who Sold $10M at the Top Now Buying Back After 65% Crash
January 13, 2026 · by Fintool Agent
Carl Rickertsen, a Strategy+3.66% board member for 23 years, purchased 5,000 shares at $155.88 on January 12—the same day the company announced its biggest Bitcoin purchase since July. The $779,000 buy might not sound massive for a company with a $47 billion market cap, but context matters: this is the same director who sold his entire position for $10 million at ~$375 per share in June 2025.
He's buying back in 58% lower.
The Smart Money Playbook
Rickertsen's trading history reads like a textbook case of timing:
June 2, 2025: Liquidated approximately 27,370 shares across two transactions at prices between $372-$379, netting roughly $10 million. At the time, MSTR traded near its highs, and Bitcoin hovered above $100,000.
January 12, 2026: Filed a Form 4 disclosing the purchase of 5,000 shares at $155.879. MSTR has since fallen 65% from its 52-week high of $457.22 to around $162.
The timing wasn't just lucky. Insiders who file Form 144s (notice of intent to sell) typically have visibility into company trajectory. Rickertsen, a Stanford and Harvard MBA grad who ran private equity at Thayer Capital Partners, knows how to read the tape.
Ask Fintool AI AgentWhat Changed His Mind
The purchase coincides with Strategy announcing it acquired 13,627 BTC for $1.25 billion at an average price of $91,519—its largest single-week purchase since July 2025. The company now holds 687,410 Bitcoin worth approximately $62 billion at current prices, acquired for a total cost basis of $51.8 billion (~$75,353 per coin).
Several catalysts may have prompted Rickertsen's reversal:
MSCI Index Relief: On January 6, MSCI announced it would not exclude digital asset treasury companies from its indexes, removing an overhang that could have triggered billions in forced selling.
Bitcoin Stabilization: After falling from $126,000 in October to below $85,000 in December, Bitcoin has rebounded to ~$90,000, suggesting the worst of the crypto drawdown may be over.
Valuation Reset: At $162 per share, MSTR trades at roughly 0.75x the value of its Bitcoin holdings—down from a premium above 2x at its peak.
The Bigger Picture
Rickertsen isn't the only Strategy insider to sell at elevated prices. SEC filings show total insider sales at the company have exceeded purchases by $864 million over the past five years. Michael Saylor himself has structured compensation to minimize direct share ownership.
But open market purchases by long-tenured board members carry weight. Rickertsen has sat through every Bitcoin cycle since Strategy pivoted to its treasury strategy in 2020. He watched the company's holdings grow from 21,454 BTC to nearly 700,000 BTC.
If anyone has conviction about where MSTR goes from here, it's the directors who've seen every twist in the Saylor Bitcoin thesis.
Ask Fintool AI AgentWhat to Watch
Rickertsen's purchase is a data point, not a guarantee. The stock remains volatile and highly correlated to Bitcoin's price swings. Strategy's aggressive capital raises through equity sales and convertible debt continue to dilute shareholders.
But when a 23-year board veteran who sold everything at the top starts buying back at the bottom, professional investors take notice. The next test: whether other insiders follow his lead—or whether this is a solo bet that Bitcoin and MSTR have bottomed.
Related: Strategy+3.66%