Block (Square) vs PayPal

In 2009, software engineer Jim McKelvey was trying to sell a custom glass faucet for $2,000 but had to walk away from the sale because he couldn't accept credit cards. Frustrated by the merchant account monopoly that required expensive equipment and long credit checks, he called his friend Jack Dorsey, who was then sidelined from Twitter. Operating out of a studio apartment, they jury-rigged a prototype that plugged a simple plastic reader directly into an iPhone's audio jack. This tiny square dongle bypassed the entire merchant banking cartel, allowing any vendor to process credit cards instantly for a flat 2.75% transaction fee.

In a desperate bid to gain mainstream corporate legitimacy before its IPO, Square signed a massive processing deal with Starbucks in 2012, with Howard Schultz joining the board. The contract turned into a financial disaster as Square severely underpriced its processing fees to win the volume. By 2014, financial filings revealed that the Starbucks deal had actively bled over $70 million from Square's balance sheet due to high transaction processing costs. Square was forced to terminate the agreement early in 2015, absorbing a huge loss but successfully preserving the cash-generating merchant base that Wall Street valued.

While Square was built for physical small businesses, its ultimate modern cash cow came from an internal hackathon project originally called Square Cash. Under the aggressive leadership of Brian Grassadonia, the app integrated a clever peer-to-peer network design that allowed users to claim custom "$cashtags." By adding instant Bitcoin purchasing in 2018 and aggressively sponsoring hip-hop culture through viral Twitter cash giveaways, Cash App evolved from a simple Venmo clone into a dominant banking ecosystem for underbanked demographics, generating over $2 billion in quarterly gross profits.

In late 2021, Jack Dorsey stepped down as CEO of Twitter to focus entirely on the fintech company, officially rebranding Square as Block, Inc. to signal a permanent shift toward blockchain technology and decentralized finance architectures. Weeks later, Dorsey executed the company's largest and most controversial transaction: a massive $29 billion all-stock acquisition of Australian Buy-Now-Pay-Later pioneer Afterpay. Critics slammed the deal as a peak-bubble acquisition that diluted existing shareholders, but Dorsey insisted it was crucial to integrate micro-credit directly into the Cash App checkout ecosystem.

By mid-2026, Block, Inc. successfully stabilized its dual ecosystem, with annual transaction volume climbing past a record $240 billion across its merchant terminals. Under Jack Dorsey's strict guidance, the company shifted a significant percentage of its corporate balance sheet and engineering resources into decentralized Bitcoin infrastructure, including the mass production of its proprietary three-nanometer mining chips. This heavy crypto integration drew persistent criticism from conservative institutional analysts, but Cash App's high-margin digital banking services kept total fiscal revenue strong at $24.8 billion.

PayPal was not originally called PayPal. Confinity — founded by Peter Thiel and Max Levchin — built software that could beam money between PDAs. At the same time, Elon Musk founded X.com, an online bank. In March 2000, they merged. The combined company was renamed PayPal in 2001, after a product Musk reportedly disliked. Musk would spend decades later trying to revive the X name for Twitter.

While Elon Musk was on his honeymoon in October 2000, the board voted to remove him as CEO and replace him with Peter Thiel. Among the complaints: Musk wanted to migrate the entire payment platform from Unix to Windows servers — a decision engineers considered technically catastrophic. Musk was furious. The company kept Unix. The episode foreshadowed Musk's combative relationship with boards for the next two decades.

PayPal went public in February 2002. Eight months later, eBay acquired it for $1.5 billion. The group of early PayPal employees — Musk, Thiel, Levchin, Reid Hoffman, David Sacks, Keith Rabois — became known as the "PayPal Mafia." They went on to found or fund LinkedIn, YouTube, Yelp, Palantir, SpaceX, and dozens of other companies. No single company has produced more consequential founders than PayPal.

After years of activist investor pressure, eBay spun off PayPal as an independent publicly traded company in July 2015. PayPal's market cap at separation was $46 billion. eBay's was $33 billion. The subsidiary had become more valuable than the parent — a pattern that would repeat across corporate history.

PayPal reached a peak market cap of over $360 billion in July 2021. Then rising interest rates, intensifying competition from Apple Pay, Stripe, Cash App, and Venmo eroded its edge. The stock fell over 75% from its peak by 2022 — one of the most dramatic collapses of any major U.S. fintech. Under new CEO Alex Chriss, appointed in 2023, PayPal pivoted aggressively toward AI-powered checkout tools and merchant services, attempting to recapture relevance in a payments landscape it once dominated.