Block (Square) — What I Think
Square started as a piece of plastic in a headphone jack. That little dongle carried a worldview most of the industry found beneath them: the small merchant is not a small bank’s customer. They’re an abandoned one.
The banks looked at the food truck, the hairdresser, the person selling at a craft fair, and saw underwriting risk and tiny volumes. Not worth a merchant account. Square looked at the same person and saw the actual frontier. Let anyone take a card in ninety seconds with no contract, and you don’t just win small merchants, you create them. People who never sold anything now could. That’s not capturing a market. That’s manufacturing one. The most underrated growth in fintech is when your product grows the number of people who can transact at all.
Then Square did the thing I think is its real genius, usually mistold as two unrelated companies stapled together. It built two flywheels facing opposite directions. The seller ecosystem, point-of-sale, capital, payroll, the merchant’s whole financial life. And Cash App, the consumer’s whole financial life. Same instinct on both sides: take the product the incumbents made gatekept and ceremonial, and make it a default. Cash App especially understood that for a huge population, the “bank account” is a phone app a friend told them about. Distribution through social proof, not branches. That’s a profound read on how money actually spreads.
Where it gets interesting, and where Block is bolder than its peers: Dorsey genuinely believes Bitcoin is the open protocol layer the internet’s money should run on, and he’s bet the company’s identity on it. The name change, the hardware, the mining, the self-custody. Most fintechs treat crypto as a feature to upsell. Block treats it as the eventual substrate. I don’t think Bitcoin-specifically is obviously the right horse for payments, its design optimizes for sovereignty over throughput, which is a real tension for a payments company. But the direction, that money should run on open permissionless rails rather than rented private ones, is the most honest long bet on this whole list.
The risk is the strength. Conviction. A company this thesis-driven can be early in a way that looks, for years, exactly like being wrong.
Favorite & worst CEO
This is essentially a founder-CEO story, so:
On its leadership. Jack Dorsey is the rare payments founder who treats money as a political and architectural question, not just a product one. The dongle, Cash App’s viral spread, the rebrand to Block, the full-throated Bitcoin bet, all from one belief that financial access shouldn’t need permission from incumbents. He’s also willing to be early and weird, which is how you get both Cash App and a decade of skeptics. My one critique: that same conviction can run over product focus, and a company carrying two huge ecosystems plus a protocol crusade can spread itself thin. But I’d rather critique a founder for believing too much than too little.
Part of “What I Think About the Top 50 Fintech Companies of All Time.” I’m Prajjwal Chittori. prajjwalchittori.com.