How a band of P2P hackers planted the seeds of a unique expense management giant

Individuality often has no place in the enterprise software space. In a market where a single contract can easily run into the millions, homogeneity is the herald of reliability and serves to reassure buyers of the worth of their potential purchase.

So it’s natural to think a company in the expense report management business would keep it simple and play it by the book. But one look at Expensify is enough to tell you that this is a company that never even looked for the book.

Right from its famous “workcations,” to its management structure and its decision-making policies, Expensify has it in its DNA to eschew so-called best practices for its own ideas — a philosophy rooted in its founder and early team’s P2P hacker background and do-it-yourself attitude. As a result, Expensify is atypical of startups in many ways, inside and out.

Founder and CEO David Barrett made it clear his company was different in our first call itself: “We hire in a super different way. We have a very unusual internal management structure. Our business model itself is very unusual. We don’t have any salespeople, for example. We’re an incredibly small company. We focus on the employees over the bosses. Our technology stack is completely different. Our approach toward product design is very different.”

That description would make some people call Expensify weird even by startup standards, but this essential difference has set it apart in a space dominated by giants such as SAP Concur and Coupa. And that’s ultimately been to its benefit: Expensify reached $100 million in annual recurring revenue in 2020, with hefty 25% EBITDA margins to boot. There were also rumors of the company planning to go public during our interviews for this EC-1, but they stopped speaking to us in March, and now we know why: Expensify confidentially filed to go public on May 3.

Expensify’s origin story is one of a scrappy group of developers who turned travel into a catalyst for ideas and stuck together through highs and lows, ending up building one of the most unexpectedly original companies in enterprise software today.

When David met Travis …

To truly understand Expensify, you first need to take a close look at a unique, short-lived, P2P file-sharing company called Red Swoosh, which was Travis Kalanick’s startup before he founded Uber. Framed by Kalanick as his “revenge business” after his previous P2P startup Scour was sued into oblivion for copyright infringement, Red Swoosh would be the precursor for Expensify’s future culture and ethos. In fact, many of Expensify’s initial team actually met at Red Swoosh, which was eventually acquired by Akamai Technologies in 2007 for $18.7 million.

Barrett, a self-proclaimed alpha geek and lifelong software engineer, was actually Red Swoosh’s last engineering manager, hired after the failure of his first project, iGlance.com, a P2P push-to-talk program that couldn’t compete against Skype. “While I was licking my wounds from that experience, I was approached by Travis Kalanick who was running a startup called Red Swoosh,” he recalled in an interview.