Buy high, sell never: Saylor keeps buying Bitcoin at local tops despite mounting risk

Strategy (previously MicroStrategy) has earned a popularity for making its weekly Bitcoin acquisitions close to the local prime in current weeks.

On Nov. 10, CryptoQuant analyst JA Marturn noted that the agency’s most up-to-date acquisition disclosure from Michael Saylor adopted the identical script.

According to an SEC filing, Strategy introduced that it had acquired 487 BTC between Nov. 3 and Nov. 9 for $49.9 million at a median value of $102,557 per coin.

While the flagship asset spent a lot of the previous week buying and selling sideways, Bitcoin had reached a high of above $106,000 on Nov. 3 earlier than sliding greater than 9% to commerce briefly beneath $100,000. It continues to battle with the $106,400 support-turned-resistance and the $100,000 local flooring.

However, Saylor’s agency was unable to purchase at the market backside. Instead, the purchases arrived at one of many highest costs the highest asset traded final week.

This is according to the agency’s earlier purchases, which coincided with short-term peaks, and raises the query of why the agency continues to “purchase the highest.”

While the consistency of this visible sample fuels an impression of mistimed execution, it tells solely a part of the story.

Why Strategy tends to purchase into BTC power

Strategy’s purchases are inclined to cluster round moments of elevated liquidity for causes unrelated to market enthusiasm.

The firm’s corporate treasuries deploy capital at particular factors, akin to after fairness gross sales, convertible issuances, or inside liquidity occasions.

These home windows not often align with discounted market situations. Instead, they usually open during times when Bitcoin is buying and selling with deeper order books and decrease execution risk.

Market analysts have famous that this structural actuality explains why Strategy’s entries usually align with local highs. Large company orders are executed when market depth is strongest, which usually corresponds with rallies moderately than durations of drawdown.

As a outcome, acquisition filings can create an optical phantasm of systematically buying at peaks, even when the timing is ready by liquidity availability and inside controls moderately than sentiment.

For Strategy, the marginal value of a given tranche is secondary.

Saylor has persistently framed Bitcoin as a long-duration financial instrument, and the agency’s operations observe that doctrine. The goal is regular publicity, not precision timing.

So, the agency’s execution home windows are outlined by company processes, and consistency of accumulation is prioritized over opportunistic entry.

Long-term efficiency vs. structural dangers

Over an extended horizon, criticisms of Strategy’s timing lose some drive.

Since Strategy started buying Bitcoin in 2020, its treasury has grown into one of the vital worthwhile company asset allocations in fashionable historical past.

The firm now holds 641,692 BTC, valued at roughly $68 billion, which was bought at a median value of $106,000, leading to a complete price foundation of $67.5 billion. At present costs, that place implies roughly $20.5 billion in paper good points.

Even extra putting, Strategy has generated over $12 billion in Bitcoin good points in YTD 2025, despite slowing its tempo of accumulation to a couple hundred cash in current weeks.

This is the paradox at the center of the Saylor technique: the entries look poor, however the outcomes are distinctive. It exhibits a company dollar-cost averaging on a structural timeline.

Short-term volatility amplifies the impression that Strategy buys tops; the multi-cycle actuality exhibits that these “tops” usually turn out to be deeply worthwhile entries over time.

A broader comparability emphasizes the purpose. Over the previous 12 months, Strategy’s equity (MSTR) has proven 87% volatility, sharply larger than Bitcoin’s 44%, and extra risky than the corporate’s different digital-asset merchandise.

Yet despite this depth, the cumulative publicity to Bitcoin has turned that volatility into uneven upside.

However, the sturdy returns don’t immunize the corporate from structural vulnerabilities. Barchart data exhibits {that a} $10,000 funding in MSTR through the dot-com peak could be value $7,207 right now, illustrating twenty years of volatility unbiased of the Bitcoin technique.

Moreover, some analysts argue that Strategy’s dependence on capital markets introduces materials dangers if the cryptocurrency enters a multi-year downturn.

Those issues have intensified as the corporate’s stability sheet has developed.

Chris Millas, an advisor at Mellius Bitcoin, Brazil’s first Bitcoin treasury agency, noted that over the last bear market, the agency carried no interest-bearing debt and had years earlier than its earliest bond maturities. So, its fairness volatility was painful however had a restricted operational impression.

However, this cycle is totally different. Strategy now holds interest-bearing obligations that have to be serviced no matter market situations.

Millas argued {that a} extreme drop in MSTR’s share value, which is traditionally believable given the inventory’s drawdowns of 70–80% in prior cycles, would restrict the corporate’s flexibility and enhance the probability of dilutive capital issuances.

According to him, that dilution, in flip, may stress the inventory additional, making a suggestions loop that magnifies draw back risk.

Indeed, Strategy faces roughly $689 million in curiosity funds due in 2026. Without new capital, the corporate can’t meet that obligation.

Moreover, current fundraises spotlight how financing situations have shifted, with preferred-share offerings pricing yields round 10.5%, above the preliminary steerage of close to 10%. The widening unfold indicators that capital is turning into dearer, complicating the economics of debt-funded Bitcoin accumulation.

Due to this, skeptics have identified that the mannequin resembles a leveraged carry commerce with restricted margin for error. In truth, some have labeled the method “Ponzi-like”, whereas arguing that the agency’s liabilities are rising quicker than working earnings.

According to them, this leaves Strategy depending on both rising Bitcoin costs or continued investor urge for food for high-yield devices.

Signal energy and narrative technique

Even with these dangers, Strategy’s purchases proceed to exert outsized narrative affect. The firm recordsdata frequent and clear disclosures, and its visibility permits the acquisitions to operate as a type of market signaling.

So, Strategy’s buying into power reinforces the message that Bitcoin is a long-term financial asset moderately than a timing-sensitive commerce.

Moreover, as a number of of Strategy’s higher-price filings in current weeks have coincided with durations of market hesitation, the filings contribute to stabilizing sentiment by demonstrating regular institutional demand.

This has allowed Strategy to successfully place itself because the market’s most constant large-scale purchaser, and its disclosures serve each operational and symbolic functions.

This twin function explains why Saylor continues to build up by short-term peaks.

For Strategy, the acquisition value of any given week is secondary to the multi-year trajectory of each Bitcoin and the corporate’s id as its largest company holder.

The optics could draw criticism, particularly during times of elevated volatility. Still, the framework guiding the purchases stays constant: Strategy will not be positioning for the following quarter, however for the following decade.

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