Michael Saylor, executive chairman of Strategy, formerly MicroStrategy, says the next Bitcoin bull market is not approaching — it has already begun. In interviews on Schwab Network and Bloomberg Television between October 13 and 20, 2026, Saylor argued that Bitcoin has entered a new four-year bull cycle, tracing the starting point to late June, when the asset established what he describes as its bear-market floor.
The call comes from an executive whose company holds approximately 4% of all Bitcoin, a stake that gives him an obvious interest in the outcome.
The technical case
The centerpiece of Saylor's argument is chart-based. Bitcoin fell to a bear-market low slightly below $60,000 in late June 2026 and then rebounded off its 200-week moving average — the average closing price over roughly four years, a line many traders treat as the boundary between a bruised market and a broken one.
Since that bounce, Bitcoin has climbed approximately $20,000. In late October it traded in a range of about $77,000 to $83,500, a 42% increase from under $65,000 in the third quarter, according to research compiled on the rally. The price remains roughly 34% below its all-time high near $126,000, set in October 2025.
Structural tailwinds, and one headwind
Saylor did not rest his case on the chart alone. He credited several structural shifts that he believes are feeding demand:
- Bank lending against Bitcoin, which lets holders borrow against their coins rather than sell them
- Tokenized securities, the growing practice of representing traditional assets on blockchains
- Digital credit issuance, an area where Strategy itself has been active
- A favorable regulatory environment for digital assets
Not every factor points upward. Saylor flagged restrictive monetary policy as a headwind, since tighter money tends to drain enthusiasm from risk assets of all stripes.
Targets and the size of Strategy's stake
Saylor attached numbers to his optimism, asserting that Bitcoin could reach $100,000 within the next year and anticipating an annual growth rate of 20-30% over the next two decades.
Context matters here. Strategy holds approximately 845,000 to 848,250 BTC, about 4% of Bitcoin's total supply. That stack is worth approximately $70-76 billion, and the company also carries $5 billion in cash. When Saylor says Bitcoin is heading higher, he is effectively talking about the single largest line item on his company's balance sheet — an argument from an interested party rather than a neutral reading of the tape.
A cycle Strategy knows well
The most recent wave peaked in October 2025 near $126,000. What followed was a slide that bottomed slightly below $60,000 in late June 2026, cutting the price roughly in half from peak to trough. Strategy held its position throughout, having built its identity on accumulating Bitcoin through good markets and bad.
What has changed since earlier cycles is the plumbing around the asset. Saylor's list of tailwinds, from bank lending to tokenization, describes a market increasingly wired into traditional finance rather than sitting off to the side of it.
What to watch
The first variable is the 200-week moving average. Saylor's thesis leans heavily on Bitcoin having bounced off it, so a decisive break back below that line would undercut the argument at its foundation.
The second is the gap between the current price and the prior peak. At roughly 34% below the October 2025 high, Bitcoin has meaningful ground to recover before a full comeback could be claimed. Saylor's $100,000 target sits above the late-October range but well short of the old record, implying a recovery rather than a new frontier within his one-year window.
The third is monetary policy, which Saylor himself flagged as a challenge. Restrictive conditions can weigh on assets that offer no yield, and Bitcoin has shown sensitivity to shifts in the broader rate outlook in the past. For Strategy shareholders, the stakes are more direct: with roughly 845,000 or more coins on the books, the company's fortunes remain tightly bound to whether the latest cycle call holds up.
