The Expensify EC-1

Let’s make it clear from the outset that this story is about an expense management SaaS business called Expensify. As you’d expect, yes, this is about the expense management market and how Expensify has grown, its technology and all of that. Normally, that would make us change the channel. But this is also a story about pirates; peer-to-peer hackers who asked, “Why not work from Thailand and dozens of countries across the globe?” and actually did it using P2P hacker culture as a model for consensus-driven decision-making — all with pre-Uber Travis Kalanick in a guest-starring role.

Most interestingly, this is a story about just not giving a damn about what anyone goddamn thinks, an approach to life and business that led to more than $100 million in annual revenue, and an IPO incoming on what looks to be a very quick timetable. Prodigious revenues, 10 million users and only 130 employees running the whole shebang — that’s a hell of an achievement in only 13 years.

If you’re going a bit “WTF,” well, we’d concur. Expensify is as contradictory as they come in the enterprise world. It’s managed to take what might well be the most boring part of the corporate business stack and turn it into something special. It doesn’t borrow its culture from other startups, it built its own tech stack from the ground up, and even hires in a completely radical way. Oh, and no one really has job titles either, because why the hell bother with hierarchy anyway? They’re pirates after all.

If expense management is about avoiding corporate plunder, then letting the pirates and hackers run the ship is probably the best approach. And now, Expensify is plundering the corporate spend world one travel ticket and business meal at a time just as the world is rebuilding in the wake of COVID-19.

TechCrunch’s writer and analyst for this EC-1 is Anna Heim. Heim is a tech journalist and former startup founder who has written for different tech publications since 2011. She recently joined Extra Crunch as a daily reporter, where she will be sharing insights on startups, particularly in SaaS. The lead editor of this package was Ram Iyer, the series editor was Danny Crichton, the copy editor was Richard Dal Porto, and original illustrations were created by Nigel Sussman with art direction from Bryce Durbin.

Expensify had no say in the content of this analysis and did not get advance access to it. Heim has no financial ties to Expensify or other conflicts of interest to disclose.

The Expensify EC-1 will be a serialized sequence of five articles published over the course of the coming weeks. We interviewed the company in February and March, well before the company announced a confidential filing of its S-1 to the SEC. Let’s take a look:

• Part 1: Origin story “How a band of P2P hackers planted the seeds of a unique expense management giant” (2,400 words/10 minutes) — Explores the colorful history of the Expensify founders’ days with Travis Kalanick’s venture before Uber, a P2P content distribution startup called Red Swoosh, and how that experience would eventually influence what would one day become an expense management giant.
• Parts 2-5: Upcoming shortly.

We’re always iterating on the EC-1 format. If you have questions, comments or ideas, please send an email to TechCrunch Managing Editor Danny Crichton at danny@techcrunch.com.