Startup Stories: Expensify

Hey, I’m Chris. I wrote this article and I’m also the founder and Editor of DailyTekk. Lets connect on Twitter, Instagram, Snapchat and YouTube. Check back daily!

Prepare to laugh and learn on this edition of Startup Stories where we get a first-hand glimpse into the genesis of Expensify, whose playful slogan “Expense reports that don’t suck” should clue you in to the fact that this is no boring story. David Barrett, Expensify’s founder who has been a programmer since age 6, who ironically hates expense reports, sheds some tells you how Expensify got its start. 

A funny think about Expensify is that we initially had absolutely no interest in expense reports. In fact, we only intended to use the guise of being a boring expense report company in order to convince a bank to let us build an entirely different financial technology product: I literally picked expense reports because it was the dullest thing I could imagine. But once we launched, we realized expense reports is actually an amazing space in every possible way: great customers, technology, revenue, viral opportunity, mobile, travel, etc.

Our first non-coffeeshop office was the penthouse suite of a high-end apartment complex in San Francisco. 19th floor, amazing views, conference room, pool table, wifi. It’s free for tenants to reserve for parties, but is always empty during the day. But we didn’t live there, so every morning we’d wait for someone else to open the door, and then casually slide in before the door closed. We did this for 8 months. Even though we had several employees and millions of dollars in funding: it was such a great place to work we didn’t bother getting an office for a long time.

The local community helped less than I expected. Don’t get me wrong: the Bay Area is the ultimate place to raise money. But it’s extremely noisy, and most startup “best practices” are really about how to pump and dump your company by selling it to a bigger sucker. Ultimately I think the community can be very harmful and distracting if you don’t have confidence and a clear sense of purpose.

Fun fact: Expensify started as a prepaid debit card company, and only built an expense report system to demonstrate our awesome financial technology. MasterCard canceled our cards the day after launch.

Startups are emotionally trying experiences. The highest high was convincing my co-founder, Witold Stankiewicz to join. It’s incredibly validating to have someone else you respect tell you that you’re not crazy after a year of secretly working on an idea that most people thing is stupid and impossible. The lowest low would be unwinding the demoralizing consequences of an employee disrupting the company and ultimately being fired. I absolutely hate firing people, but I find it a depressingly regular part of the job—one that I’ve learned to do sooner, rather than later—despite enormous pains taken to hire only the best.

I’d have to say Travis Kalanick, the current CEO of Uber, and founder of Red Swoosh (the company where we met). Working with him gave me the confidence that I could actually do this, and for that I’m eternally grateful.

This is an incredibly difficult challenge. There are so many pressures to conform to the expectations of others that it takes enormous discipline to build the company you want, rather than the company everyone tells you you’re supposed to build. For example, we go overseas as a company for a month every year — we just got back from Thailand. It sounds totally crazy: 25 people on a remote beach with nothing but laptops and backpacks? But we do it anyway, and that’s just one of countless examples of doing what makes sense to us, even if it’s inconceivable to others.

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