Expensify began as a cover story for a much riskier idea. In fact, Expensify wasn’t supposed to exist at all.
Back in 2008, David Barrett had a different plan: a prepaid debit card linked to his personal account to help people experiencing homelessness buy food without handing over cash. But the banks balked—too weird, too risky, and too hard to understand. So he came up with a Trojan horse: pitch a boring corporate expense platform to get the card idea funded.
The problem? Everyone loved the Trojan horse.
Barrett wasn’t even planning to build it—at the time, iPhone cameras were too grainy to scan receipts, and enterprise apps didn’t come from app stores. But then autofocus arrived. Suddenly, the impossible became real. Barrett scrapped the card idea and doubled down on expenses. What started as a workaround became the real deal.
Expensify caught fire through word of mouth. No sales team. No marketing budget. Just a product that users liked enough to pitch to their own finance teams. By 2021, it went public on Nasdaq. Today, more than 12 million people use Expensify to scan receipts, reimburse employees, manage corporate cards, pay bills, and more—all from a single app.
But Barrett never stopped questioning the status quo. He built a blockchain-powered database before Bitcoin existed. He rejected traditional sales playbooks, avoided “brilliant jerks,” and took the entire company overseas for a month every year. Along the way, he introduced Karma Points, a first-of-its-kind card reward that donates a portion of revenue to causes like housing equity and food security.
His mission hasn’t changed since those early days in San Francisco’s Tenderloin district, where the idea was born: build something useful, with people he believes in, and never let the soul of the company get swallowed by scale. In a world obsessed with polish and perception, Barrett is still betting on instincts—and he’s still proving everyone else wrong.
