This is Hamamoto from TIMEWELL.
What Jack Dorsey Is Building
Jack Dorsey's Twitter profile reads simply: "#bitcoin." That single word tells you a lot. Dorsey is currently CEO of both Twitter and Square, and founder of Square Crypto. Three companies, two CEO roles simultaneously.
My admiration for Dorsey starts with his philosophy. He practices Zen Buddhism, values wabi-sabi (finding beauty in imperfection), and carries a minimalist sensibility that resembles a softer version of Steve Jobs. His guiding mission—common across both Twitter and Square—is to use the internet's greatest strength: eliminating barriers instantly, at global scale.
- Twitter: Break down language and cultural barriers through information
- Square: Break down barriers to value exchange through finance
This article focuses on Square.
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Square's Three Business Lines
1. Cash App (Consumer payments, crypto, equities)
Cash App allows peer-to-peer money transfers, Bitcoin purchases, and stock trading. Its competitors include Venmo (PayPal), Robinhood, and Coinbase.
Two years ago, most observers assumed Venmo was untouchable. What happened instead was a rapid, domino-like market share shift toward Cash App. The key driver: exceptional user experience. Several early employees came from Apple's design team, and Dorsey's own design convictions run deep.
Cash App also has an interesting Bitcoin-specific design: the app is configured by default to automatically accumulate a small percentage of Bitcoin. This is deliberate—Dorsey is building toward Bitcoin as a global payments standard, not a speculative trading vehicle. Where Coinbase facilitates speculation, Cash App is designed for utility. The underlying infrastructure is Lightning Network, which resolves Bitcoin's original speed and fee problems. On Cash App's platform, Bitcoin transactions are effectively near-instant and near-zero cost.
2. B2B POS Systems (Point-of-sale for merchants)
Square's POS business is often compared to Recruit Holdings' AirREGI in Japan. But the business models differ significantly. Recruit's model historically bundled AirREGI as a free service, funding it through advertising revenue from platforms like Gurunavi. Square charges merchants a straightforward transaction fee.
For merchants, the advertising-dependent model requires constant spending on a platform whose performance they can't fully control. The transaction fee model is simpler and more predictable. Square also runs a rewards program for merchant loyalty customers—connected directly to Cash App—which creates a new revenue stream as it scales.
COVID hit the POS business hard. The recovery from that impact is one of the clearer tailwinds in Square's medium-term trajectory.
3. Square Capital (Data-driven lending)
This is traditional bank lending—reimagined with real-time merchant data.
Banks historically set lending limits based on deposit balances and transaction histories. Square's lending model uses live POS transaction data to assess business health and set loan amounts. The result is lending decisions that are, in theory, more accurate and faster than conventional bank processes. In a low-interest environment, the margins are compressed. But as rates normalize and economic activity recovers, Square Capital's lending business becomes a meaningful growth driver.
The Business Portfolio Logic
Square operates well regardless of macroeconomic conditions. Cash App performs in both bull and bear markets. The POS business is correlated to economic activity, but the lending business provides a natural hedge. The combination is more durable than any single fintech vertical.
More importantly, Square's long-term ambition is for Cash App to become the infrastructure for global payments—including international B2B settlement. If that vision materializes, the scalability of this business is extraordinary.
On Decentralization
I'll end with a personal note. Mark Zuckerberg attempted to create a proprietary global currency—a centralized financial system controlled by a single company. I find that model troubling. Bitcoin has no single leader; it's a distributed system. Everyone is an equal participant. A currency governed by its users, rather than by a corporation, is the kind of financial infrastructure that makes sense for the future. That's why I'm both a Square watcher and a Bitcoin supporter.
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