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CEO Interview: David Barrett of Expensify

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This week we interviewed David Barrett, CEO of Expensify, an expense-processing platform. Barrett launched the San Francisco-based startup in May of 2008 and now employs 10 people. 

Expensify has been recognized as CNN Money’s One of Five Best Apps for Business, has taken home a Best of Show award at FinovateSpring 2010, was featured as the App of the Week by both Gearburn and Salesforce, and has received $6.7 million in funding.

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Finovate: I see that you’ve been programming since the age of 6. Tell us about what you were programming and what drove you to do so at such a young age.

Barrett: I started watching my brother type in games from Byte magazine into our trusty Vic-20. Then when my parents went to the mall they’d leave me in Radio Shack and I’d write programs on the Tandy computers there while they shopped — a bat that flew around the screen was my favorite. The magazines I read alone in my room at night had pictures of the latest 8086 computer with its seductively glowing amber screen, quite unlike the magazines of my peers. But ultimately it was a combination of living in the midst of farm fields miles from friends (and being antisocial with few friends in the first place), combined with summer vacations on a sailboat in the middle of Lake Michigan. I didn’t really have much to do but write in my trusty notebook about ideas to explore, games to build, and things to do once I was off that damn boat and back in my room.

Finovate: Tell me about when you first had the idea for Expensify’s receipt-importing platform.

Barrett: The moment I saw the image quality an iPhone camera could have with auto-focus enabled. It’s not exactly a genius idea — it’s just so amazingly obvious. Of *course* it should work like this: just take a picture of the receipt, and magically everything is read off it and associated with your credit card feed automatically. I can’t think of any way *but* that to work. Unfortunately, it’s easier said than done, which is why it took literally years of development to make it possible.

Finovate: What has most surprised you about launching Expensify?

Barrett: How much fun it can be to disrupt a boring space. It sounds absurd, but in truth I picked expense reporting precisely *because* it sounded boring: Banks wouldn’t talk to me about my original idea because it sounded too crazy. So I re-cast it as expense reimbursement and, voila. Boring. Or so I thought, but it turns out that this space sits at the absolute heart of every organization. It affects all industries, all company sizes. Everybody in the company from the CEO to the janitor. It affects the obvious companies like sales and consulting, but also churches. Student groups. Families. It’s for anybody who’s ever put a receipt in their pocket.  It’s the great equalizer. As a result, Expensify has become — quite to my surprise — a product for Everyman. It’s equal parts humbling and exhilarating.

Finovate: Last year you took your entire team to Vietnam for a month. What was your favorite part and would you recommend it to other startups?

Barrett: My personal favorite moment was sitting in the midst of Marble Mountain, an ancient Buddhist temple carved into a deep cave accessible only from the top of a tall mountain, itself only accessible by a winding staircase up the sheer cliff sides. It’s so hard to get out of your habits at home and into a place — physically and mentally — truly different. It’s that different mental state that I find is the most valuable part of the trip. It triggers a level of introspective discussion that simply doesn’t happen in the office, no matter how many pizzas you order, or how late you order them.

Finovate: What advice would you give a fintech entrepreneur who is just starting?

Barrett: Everything goes slower than everybody tells you it will. Prep yourself for a marathon. Even worse: a marathon where everybody else is sprinting off the blocks, in different directions. In the fog.

Finovate: What is your favorite part about leading Expensify?

Barrett: I think “leading” is a strong word. As stressful and chaotic as it is, I like having a strong team of independent peers, each pulling the company in the way they feel is best. And then I like going home and having dinner with my wife and dog, confident that this is so much bigger than me, I can sleep soundly.

Finovate: How has Expensify adapted to accomodate growth?

Barrett: I don’t know that we have, at least not that well. For the astounding number of users we have and companies who depend on us, we’re still too small. We struggle to hire really great people, and are constantly tempted to lower our standards. But so far we haven’t, and that feels very good, despite the increased work it creates for everyone. (Hint:

Finovate: Can you give us a sneak peek of what’s next for Expensify?

Barrett:In broad strokes, Expensify has the basics down cold. Not perfect. Not even close to perfect. But pretty well, and better every day. But we only have the *basics* down cold. We’re always going to stay true to the roots of expense management — that not-so-boring field we call home. But we’re done catching up, and are beginning to lead in new directions that bring the latest technologies to bear on this age-old problem. Importing eReceipts from your online bank account, or SmartScanning receipts with your mobile phone — these are bold moves that nobody’s ever done before. But there are so many more things to be done (and so many better ways to do what we already do), we’re really just getting started.

To learn more about Expensify, watch David Barrett’s recent demo fromFinovateSpring 2011. Stay tuned for another CEO interview next month.