Block's 'Square Mafia' Forms After Layoffs
Following Block's massive 40% workforce reduction of over 4,000 jobs, a Slack group of former employees called the "Square Mafia" has emerged. The group, which now has nearly 4,000 members, echoes the influential "PayPal Mafia" and serves as a hub for commiseration and networking, potentially seeding future ventures and diffusing institutional knowledge from the company.
In a public memo, CEO Jack Dorsey justified the deep cuts by citing the transformative power of AI, stating that "intelligence tools have changed what it means to build and run a company." The move reduces Block's headcount from over 10,000 to just under 6,000, a decision made from a position of financial strength, not weakness. However, this AI narrative follows a period of massive expansion where Block's workforce nearly quadrupled in three years, growing from 3,835 employees in 2019 to around 13,000 by 2023. Dorsey later acknowledged the company had over-hired during the COVID-19 pandemic and had incorrectly built separate structures for its Square and Cash App divisions. Prior to this 40% reduction, Block had already conducted several rounds of layoffs in 2024 and 2025 to manage its rapid growth. Despite the human cost, Wall Street reacted positively to the aggressive restructuring, with Block's stock price surging more than 20% following the announcement. The "Square Mafia" moniker is a direct reference to the "PayPal Mafia," a group of early PayPal employees who left after its $1.5 billion acquisition by eBay in 2002. That cohort went on to found or fund a generation of iconic tech companies, including Tesla, SpaceX, LinkedIn, Palantir, YouTube, and Yelp. The original group's success stemmed from the intense bonds and trust forged during PayPal's early days, which they leveraged into a powerful professional network. The term was cemented in Silicon Valley lore by a 2007 Fortune magazine article that featured the members dressed in gangster-style attire. Departing Block employees received a severance package that included a base of 20 weeks' pay,
