The Darling of the Coffee Shop
For years, Square was synonymous with one thing: empowering the little guy. Founded in 2009, its iconic white square reader allowed food trucks, artists, and independent coffee shops to accept credit cards with a simple iPhone plugin. The mission was clear,
noble, and incredibly successful. Square championed small business, building its entire identity around the 'seller' side of the transaction. It was the undisputed leader in in-store payments for a new generation of entrepreneurs. The brand was trusted, the hardware was sleek, and the business model worked. Internally and externally, Square was the merchant services company. This strong identity became both its greatest asset and its biggest potential trap.
The Secret Weapon Hiding in Plain Sight
Meanwhile, another project was brewing within the company. Launched in 2013, Cash App started as a simple, almost overlooked, peer-to-peer payment service, Square’s answer to Venmo. For years, it existed as a separate entity, a consumer-facing app in a merchant-obsessed company. It didn’t fit the primary mission. It was seen as a side project, not the future. The app was popular for splitting dinner bills, but it wasn't initially viewed as a core part of Square's grand strategy. But as it quietly grew, adding features like a debit card and direct deposits, it was building a massive user base completely independent of Square's traditional merchant ecosystem.
A Company Divided
The pivot wasn't a single decision but a creeping realization that the future might not be in hardware, but in software and services. The proposal was to lean into Cash App—to transform it from a Venmo competitor into a full-fledged financial platform for the underbanked, a place for everything from stock trading to receiving paychecks. This was heresy for a company built to serve sellers. The internal debate was significant. Committing to Cash App felt like abandoning the small businesses that made Square a star. It required a complete shift in mindset, from B2B to B2C. The two ecosystems—the merchant-focused 'Seller' business and the consumer-focused 'Cash App'—were functionally separate, and the question of which horse to bet on was a high-stakes dilemma. For a long time, the answer was to keep them apart, a reflection of the internal reluctance to dilute the original brand.
The Gamble That Paid Off
Ultimately, leadership, including then-CFO Sarah Friar and CEO Jack Dorsey, made the call to go all-in. They saw what others inside might have missed: having both the merchant and the consumer side of the transaction was a superpower. The company began pouring resources into Cash App, viewing it as a tool that could eventually replace a traditional bank account for many users. The results were staggering. Cash App's growth exploded, especially during the pandemic, and it quickly became Square’s primary revenue driver, at one point generating over 80% of the company’s total revenue. The little side project had become the main event. It was so transformative that the parent company even rebranded from Square, Inc. to Block, Inc. in 2021, a name reflecting a more diverse portfolio beyond just merchant payments.
