Personal blog of Yzmir Ramirez

Take a close look at any ambitious startup and you’ll find pugnacity nestled in its core. Stubbornness and a bullheaded belief in the worth of what a company wants to bring to fruition is often the biggest driver of its success, and the people at such companies also tend to share this quality.

So it wouldn’t be too far off the mark to say the people at Expensify are a stubborn lot — to the company’s ultimate benefit. This group of P2P pirates/hackers that set out to build an expense management app stuck to their gut, made their own rules. They asked questions few thought of, like: Why have lots of employees when you can find a way to get work done and reach impressive profitability with a few? Why work from an office in San Francisco when the internet lets you work from anywhere, even a sailboat in the Caribbean?

It makes sense in a way: If you’re a pirate, to hell with the rules, right? And even more so when nobody can explain the rules in the first place.

With that in mind, one could assume Expensify decided to ask itself: Why not build our own totally custom tech stack? Indeed, Expensify has made several tech decisions that were met with disbelief — from having an open-source frontend and cross-platform mobile development to hiring contractors to train its AI and recruiting open-source contributors — but its belief in its own choices has paid off over the years, and the company is ready to IPO any day now.

How much of a tech advantage Expensify enjoys owing to such choices is an open question, but one thing is clear: These choices are key to understanding Expensify and its roadmap. Let’s take a look.

Built on Bedrock

I think another question Expensify also decided to ask in its early days was something like: Why not have our database on top of a technology that’s built for small-scale application software?

It may sound incredible, but Expensify actually runs on a custom database built on top of SQLite. This is surprising, because despite being one of the most widely deployed database engines, SQLite is known for running on small, embedded systems like smartphones and web browsers, not powering enterprise-scale databases.

This custom database is called Bedrock, and its architecture is as unique as they come. Expensify explains it as an “RDBMS optimized for self-healing replication across relatively slow, relatively unreliable WAN (internet) connections, enabling extremely high availability/high performance multi-datacenter deployments without any single point of failure.” RDBMS means relational database management system, describing SQLite and other row-based databases where entries are interconnected with each other.

But why would Expensify build this instead of going for any number of widely available enterprise database solutions?

To answer that question, we need to go back to the early days of the company, which was originally a side project for its founder and CEO, David Barrett. His initial idea was to develop a prepaid card for the homeless, but this required putting a server on the Visa network, which brought several strict requirements and challenges. “I would say one of the most difficult [parts] was that I needed the ability to automatically replicate and failover,” Barrett told TechCrunch when we interviewed him a couple of months ago.

This was no easy feat in 2007, but Barrett was up for the challenge. “I just hit a moment where the technology available off the shelf just wasn’t that good. And I happened to be a peer-to-peer software developer who had tons of spare time and really wanted to build this thing to put on the Visa backend,” he said. The P2P aspect was important, as Barrett had the skills to make it work. His first hires for Expensify, P2P engineers he had worked with at Red Swoosh and Akamai, were also unusually suited for the job.

Expensify may be the most ambitious software company ever to mostly abandon the Bay Area as the center of its operations.

The startup’s history is tied to places representative of San Francisco: The founding team worked out of Peet’s Coffee on Mission Street for a few months, then crashed at a penthouse lounge near the 4th and King Caltrain station, followed by a tiny office and then a slightly bigger one in the Flatiron building near Market Street.

Thirteen years later, Expensify still has an office a few blocks away on Kearny Street, but it’s no longer a San Francisco company or even a Silicon Valley firm. The company is truly global with employees across the world — and it did that before COVID-19 made remote working cool.

“Things got so much better when we stopped viewing ourselves as a Silicon Valley company. We basically said, no, we’re just a global company,” CEO David Barrett told TechCrunch. That globalism led to it opening a major office in — of all places —a small town in rural Michigan. That Ironwood expansion would eventually lead to a cultural makeover that would see the company broadly abandon its focus on the Bay Area, expanding from a headquarters in Portland to offices around the globe.

It makes sense that a company founded by internet pirates would let its workforce live anywhere they please and however they want to. Yet, how does it manage to make it all work well enough to reach $100 million in annual revenue with just a tad more than 100 employees?

As I described in Part 2 of this EC-1, that staffing efficiency is partly due to its culture and who it hires. It’s also because it has attracted top talent from across the world by giving them benefits like the option to work remotely all year as well as paying SF-level salaries even to those not based in the tech hub. It’s also got annual fully paid month-long “workcations” for every employee, their partner and kids.

Yet the real story is how a company can become untethered from its original geography, willing to adapt to new places and new cultures, and ultimately, give up the past while building the future.

The influence of a founder on their company’s culture cannot be overstated. Everything from their views on the product and business to how they think about people affects how their company’s employees will behave, and since behavior in turn informs culture, the consequences of a founder’s early decisions can be far-reaching.

So it’s not very surprising that Expensify has its own take on almost everything it does when you consider what its founder and CEO David Barrett learned early in his life: “Basically everyone is wrong about basically everything.” As we saw in part 1 of this EC-1, this led him to the revelation that it’s easier to figure things out for yourself than finding advice that applies to you. Eventually, these insights — and the adventurous P2P hacker attitude he nurtured alongside his colleagues and Travis Kalanick at Red Swoosh — would inform how he would go about shaping Expensify.

It’s striking how Expensify has managed to maintain this character 13 years later, even on the threshold of an IPO. How did this happen? During a series of interviews in February and early March, we found the answer is tied to the level of thought and effort this expense management business puts into its culture.

You see, the people at Expensify are prepared to invent their own playbook, develop it and, if needed, rewrite it completely. Its HR policies and strategy are tailored to find people who would have fun building an expense management product. It has a unique growth and recognition scheme to offset the drawbacks of a flat organizational structure. It’s even got a “Senate” that vets all major decisions. No kidding.

All this, and more, has ultimately helped Expensify reach more than 10 million users and achieve $100 million in annual revenue with just 130 employees. Let’s take a closer look at how Expensify makes it happen.

“We want the fewest people necessary to get the job done”

It’s clear Expensify’s unusually high employee-to-revenue ratio is intentional: “We want the fewest people necessary to get the job done,” Barrett says. But how do you actually achieve it? How do you hire and keep people who can deliver such results? Barrett had to learn how the hard way.

Expensify’s first team was based in San Francisco and comprised Barrett’s old Red Swoosh and Akamai colleagues, who joined a few months after Akamai fired him. A small team was enough to get started, but it was much more difficult to hire additional people. Barrett is eager to clarify the Valley is not really the best place to recruit talent: “Sure, Silicon Valley has a ton of really awesome people, but all of them have jobs!,” he says.

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.

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.