When a handful of Brex executives traveled to Santa Barbara for a leadership offsite in August 2021, instead of enjoying the breezy California beaches, they filed into a windowless, subterranean hotel meeting room. There, they holed up for three days—debating, soul-searching, and hair-pulling, their stress ricocheting off the four walls around them.

They were there to save the company.

Back in 2018, before Brex came along, founders often had a problem: Because many had no personal or business credit history, they were unable to get a corporate credit card—even if they’d just raised millions of dollars. Brex became a very Silicon Valley way of solving that problem: The company was founded by two Brazilian immigrants, one 19, the other 20, who had dropped out of Stanford and practically reinvented the very nature of how a startup credit card could work. Four months after debuting their breakthrough card, they raised over 100 million and achieved unicorn status—then grew to 1,200 employees in three years. That’s when everything started breaking,” says cofounder Henrique Dubugras.

As they settled at the table in the bowels of the hotel that August, the company’s future hinged on one question: What is Brex? The startup had begun with a singular mission, and a simple story to tell. But as it grew, that had gotten complicated. Now it was a lot of things to a lot of people, many of whom were unhappy. Brex had lost the defining clarity that had made it once stand out so boldly.

To address that big question and get back to the heart of Brex’s why, Dubugras and his cofounder Pedro Franceschi had a proposal. It seemed counterintuitive—and risky as hell. If it didn’t work, all those employees could be left without jobs. But the way they saw it, a radical problem required radical change. This was the company moment,” says COO Michael Tannenbaum. It was very scary.”