Strategy executive chairman Michael Saylor told shareholders on Monday not to invest in bitcoin unless they intend to hold for more than four years, and warned that the company may need to endure a difficult stretch before conditions improve.
“If you’re a short-term price predictor, you’re a trader, I don’t really have much useful wisdom for you,” Saylor said during a live investor Q&A. “My advice is: don’t invest in Bitcoin unless you’re going to hold it for more than four years. Ideally, hold it for 10 years.”
He acknowledged the bear market has made things “tougher” while reaffirming Strategy’s commitment to continuing bitcoin purchases. “We might have to actually ride through some number of months or a year or two to get to the point where things start to work to the benefit of the equity,” he said.
The session was hosted by Saylor and chief executive Phong Le, moderated by author Natalie Brunell and streamed on Strategy’s own channels. Bitcoin traded around $64,079 on Tuesday morning, up roughly 1% over 24 hours.
Buybacks are not the plan
Asked directly about repurchasing MSTR shares, Saylor said buybacks are not currently a priority.
Repurchases would become likely only if the stock traded at a significant discount to net asset value, he said, describing that scenario as the trigger rather than the present situation. The session focused instead on cash reserves, the company’s STRC preferred stock and flexibility around bitcoin purchases.
Strategy holds 840,447 BTC. The company reported an $8.22 billion net loss for the second quarter on July 30, driven by an $8.32 billion unrealized markdown as bitcoin fell from roughly $86,000 at the end of March to $64,915 at the end of June.
Its average cost basis sits near $75,578 per coin, leaving the treasury several billion dollars below what it paid.
The four-year framing has history
The advice is not new, but its context is.
Saylor has recommended a four-to-ten-year holding period since at least December 2024, when bitcoin first crossed $100,000. In an interview at the time he said funds not needed for four to ten years should go into bitcoin, and described his approach as “just keep buying Bitcoin with your spare capital.”
What has changed is that shareholders are now being asked to apply that patience to losses rather than gains. Strategy shares fell 72% from a summer 2025 peak of $457 to $130 by mid-February, outpacing bitcoin’s own decline over the same stretch.
That divergence broke the mechanism the company was built on. Strategy’s model depended on issuing equity at a premium to the value of its bitcoin, using the proceeds to buy more, and increasing the bitcoin backing each share. Once the premium collapsed, issuing shares diluted holders rather than benefiting them. Enterprise mNAV fell below 1 on June 27.
The capital structure took priority
Strategy’s actions over the past two months have been about servicing obligations rather than accumulating.
The company paused bitcoin purchases for five consecutive weeks, built its dollar reserve to roughly $3.75 billion, and sold approximately $218.4 million of bitcoin under a newly authorised monetisation programme to help cover preferred dividends. It also repurchased $1.5 billion of convertible notes for about $1.38 billion and bought back STRC preferred shares at a 13% discount to par.
The pressure had been flagged in advance. CryptoQuant head of research Julio Moreno urged the company in June to stop buying and rebuild its cash buffer, noting reserves had dropped about 38% from early 2026 while dividend obligations quadrupled in six months to $1.2 billion. Dividend coverage fell from more than seven years to roughly 14 months. “Buying whenever capital is available is not a strategy,” Moreno said, calling it “a formula for accumulating at cycle peaks.”
Kang has since said the $3.75 billion reserve covers preferred dividends and interest for about two years.
The credibility question
Saylor’s messaging has drawn scrutiny this year, and the reason is a shift he has disputed.
He posted “Never sell your Bitcoin” on X in February 2025, and told interviewers in 2022 that “we’re not sellers, we’re only acquiring and holding bitcoin.” At Bitcoin Prague in June, after Strategy sold 32 BTC, he said he had never claimed the company would never sell. Critics have documented multiple instances suggesting otherwise.
His distinction is defensible in narrow terms. Strategy’s filings always preserved the option to sell, and advice to individual holders is not the same as a corporate commitment. But the brand was built on the shorter version, and the July sale of $218.4 million made the ambiguity harder to sustain.
That backdrop shapes how Monday’s advice reads. Telling shareholders to hold four years while the company itself pauses purchases and sells coins to meet dividend obligations is a coherent position, but it asks retail holders for a patience the corporate treasury has been unable to fully maintain.
What it means for shareholders
The practical guidance from the session is straightforward: no buybacks unless the discount widens considerably, continued bitcoin purchases when capital allows, and an explicit warning that the equity may not respond for a year or more.
For anyone holding MSTR as leveraged bitcoin exposure, the leverage now runs in the direction they did not want. The stock has fallen further than bitcoin, the premium that justified the structure has gone, and the company is prioritising preferred dividends over accumulation.
Saylor’s four-year horizon is a reasonable framework for a volatile asset. Whether Strategy’s capital structure can absorb four years at current prices is a separate question, and one the reserve build suggests management has been thinking about carefully.
Disclaimer: This article is for informational purposes only and does not constitute financial advice. Cryptocurrency investments carry significant risk. Always conduct your own research before making any investment decisions.
