Are You Going to Be a Pain in the Ass to Manage?

For the 10 million plus users of Expensify, the company's origin story will likely come as a surprise. In founder David Barrett's mind, Expensify was a fictional startup concept that he pitched to banks to gauge their reaction for an idea he had to solve homelessness in San Francisco. But when David lost his job in 2007, he decided to turn this fictional idea for Expensify into a real business. Expensify is known to most as an expense management app, but since going public in 2021, the company continues to throttle toward a broader vision: to be a platform that facilitates conversations that accomplish things in the real world. David shares how he's kept headcount to 140 while generating over a million dollars of revenue per employee, how an employee-first acquisition model was their key to growth, and how an async work culture means the sun never sets on the Expensify empire.