Startups and other businesses created from square mafia

  • The idea of ​​Silicon Valley “mobs” first appeared with the Oracle, Facebook and PayPal mobs.
  • Former Square employees have launched startups with a cumulative value of nearly $40 billion.
  • Insider tracked down 15 members of the “Square Mafia” to see what they’re up to these days.

Silicon Valley insiders have long been obsessed with the idea of ​​a startup “mafia.”

The “PayPal Mafia” was perhaps the most infamous company that spawned the founders of tech giants like YouTube, Yelp, Tesla and LinkedIn. Facebook and Oracle also have their own mobs of ex-employees who have produced iconic tech companies like Salesforce, Asana and GoodRk.

Recently, attention has been drawn to fintech giant Square, founded by Jack Dorsey, now known as Block, whose former employees have created and run startups cumulatively valued at nearly $40 billion, based on private valuations from PitchBook and enterprise value for public companies, from this is not an exhaustive list.

“Jack and I initially hired aspiring entrepreneurs — we deliberately sought out people who had aspirations to start their own company, and we wanted those potential founders to help us build Square,” said Keith Rabois, the company’s former CEO, who now a general partner at Founders Fund and CEO of Opendoor — which is on this list.

He added that as Square grew, the company introduced programming designed to teach employees how to be founders, and the best startups were paired with external mentors to help them develop skills and learn more about building companies.

“I’ve always told employees that my job is to make your job at Square so challenging and fulfilling that you keep putting off leaving to start your own company,” Rabois said. “If your role doesn’t expand in intellectually challenging ways, then I’m perfectly comfortable with you leaving.”

Many of these former Square employees have carried over certain core values ​​from fintech to their current ventures, such as focusing on the customer, using technology to elevate the business and emphasizing consistently strong execution, they told Insider.

“Our purpose at Nextdoor is to foster a kinder world where everyone has a neighborhood they can rely on, and as Square, we see how empowering communities and small businesses at the grassroots level can really change the way those neighborhoods survive and thrive.” Sarah Friar, CEO of Nextdoor and former CFO of Square, said.

Some said Square gave them a business model to emulate for their own startups. Others said they met their co-founders or first employees while at the company.

Insider followed 15 former Square employees in their current ventures, ranging from starting multibillion-dollar public companies to running high-profile VC firms. Here’s what they’re doing now.

Rental startup Divvi Homes, co-founded by former Square product manager and CFO Adena Hefets, declined to be included on this list.

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