Strive Chairman and CEO Matt Cole posted an image stating "The first billion is the hardest." Michael Saylor, founder and chairman of Strategy, replied, "You never forget the first one," shifting the focus from scale back to the initial entry.

The company Cole is part of is pushing the nominal scale of its perpetual preferred stock SATA towards the billion-dollar mark. In the past week, approximately 70% of the funds raised through this preferred stock were used to purchase 1,375 bitcoins from August 31 to September 4, at an average price of about $79,281, increasing the total holdings to approximately 24,531 bitcoins, with a market value of nearly $1.9 billion, ranking among the top five publicly traded companies in terms of holdings. The company has also completed a full stock acquisition of Semler Scientific, incorporating its over 5,000 coins.

On Saylor's side, as of September 7, Strategy holds 845,050 bitcoins, with an average cost of about $75,412. The price of bitcoin is hovering around $77,000 to $80,000, with the account nearly breaking even, still about 38% lower than the peak in October 2025. The company has just ended a buying halt of about ten weeks and spent $369.7 million from August 24 to 30 to repurchase 4,603 bitcoins at an average price of about $80,318; previously, from June to August, it sold about 3,000 to 7,000 bitcoins to pay preferred stock dividends.

On a personal level, Saylor bought his first bitcoin on May 30, 2020, while the company purchased 21,454 bitcoins for $250 million on August 11 of the same year, at an average price of about $11,653, thus transforming the business intelligence company into the world's largest corporate bitcoin treasury. On March 20, 2000, the company saw a 62% drop in a single day due to revenue restatement, and he later paid about $8.28 million to the securities regulator to return the profits and a $350,000 fine, without admitting wrongdoing.

Over the weekend, he shared a 20-page "Bitcoin Investor's Guide," which opens not with a million-dollar target but with a historical 93.1% drawdown, custody failures, and position discipline, listing a 28% drop in one year, an annualized return of about 63% over ten years, ETF holdings of about 1.27 million coins, and a total network hash rate of about 935 EH/s. The guide is aimed at advisors, banks, and allocation firms, shifting the tone from street slogans to institutional due diligence.

In terms of market mechanics, the buyer is the listed entity seeking bitcoin beta, while the seller is a treasury company exchanging common and preferred stock for cash to buy spot bitcoin. This is an event-driven hierarchical competition: SATA touching a billion, and Saylor using the "first one" to pull the narrative back to holding discipline. Funds are flowing from preferred stock subscription to the spot order book, benefiting those top treasuries that can continuously issue structured notes, while the pressured parties are latecomers who need to sell coins to generate income after chasing high premiums.

Source: Public Information