Strive Chairman and CEO Matt Cole Posts Image Claiming 'The First Billion is the Hardest'
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
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Saylor's first purchase occurred after he was already preparing for retirement. In 2013, he stated that bitcoin lacked credible guarantees and would be regulated out of existence; seven years later, he viewed the company's $500 million cash as melting ice. On August 11, the first transaction of $250 million was completed, and he subsequently used convertible bonds and market-based issuances to pile up holdings to over 800,000 coins. The memory of the $60 billion market value evaporating in a single day in 2000 became the source of his later discipline of only buying and not selling, explaining why the guide first mentions the 93% drawdown instead of price predictions.
The capital path is to transform the equity and credit of a software company into a bitcoin leverage pipeline in one go. Convertible bonds and ATM stock sales are exchanged for bitcoin, while preferred stock sells "digital credit" to accounts needing coupon payments; the selling of coins for income from June to August indicates the pipeline has begun to reverse blood flow. Strive replicates the same blueprint but adds credit protection clauses: SATA interest rates cannot be arbitrarily lowered, and if interest is suspended, management receives no bonuses and interest rates are raised, with board seats available, using debt packaging to secure a billion-dollar subscription. Both sides are selling dilution rights of common stock to funds wanting to amplify bitcoin exposure without managing private keys themselves.
The analogy is not miners, but rather 20th-century railroads and trust companies using preferred stock to lay tracks. Strategy is the S&P of this track, while Twenty One Capital and Strive are second-tier acquirers and integrators, with Semler being acquired marking the treasury company's entry into elimination rounds. The industry phase has shifted from "who dares to exchange cash for coins first" to "who can sell preferred stock to a billion without being liquidated." The position is now about control and refinancing, not discovery.
Structural judgment belongs to capital concentration. The mechanism is: with a fixed bitcoin supply, entities that can continuously issue paper debt at costs lower than holding volatility will absorb the issuance space of retail and small treasuries. The first purchase determines faith, while the first billion determines who retains the financing window; those who cannot forget the first purchase are using the later billion to spread their average cost across the entire market.
ABAB News · Cognitive Law
The first purchase is faith, the first billion is the window.
Those who can issue preferred stock are qualified to talk about never selling.
When the supply is fixed, financing rights are scarcer than holding amounts.