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Behind the Success: Expensify

Posted 5 years ago in Apps by Rohan Reid
Posted by Rohan Reid

David Barrett is the CEO and Founder of Expensify. Named one of the Most Innovative Companies in 2015 by FastCompany, Expensify’s team has a simple goal — expense reports that don’t suck. That ethos made them a popular app in our marketplace.

David Barrett was just 6 years old when he started programming. Since he has attended the University of Michigan, written 3D graphics engines for the video game industry, and with Travis Kalanick built a peer-to-peer file transfer technology called Red Swoosh. In 2008 David started Expensify and has since been relieving the world’s frustrations, one expense report at a time. We chat to David about the triumphs and challenges on his business journey.

Why did you want to run your own business?

DB: It’s not that I’m set on running my own business. I’m just set on working somewhere great, and starting my own business was the most straightforward way to do that. Ultimately, “great” is in the eye of the beholder. In my case I wanted to work with people possessing three qualities:

  • Raw talent. The sort of people who casually move mountains without realizing others think it’s impossible. The value of raw talent is obvious.
  • Strong ambition. People who are committed to spending their life in the pursuit of some great personal goal. The value of ambition is less obvious. But I find ambitious people are far easier to work with because they waste less time on stupid things that don’t matter: their time matters to them more than someone who just wants a paycheck.
  • Deep humility. People who understand the limits of their own knowledge and not only respect, but truly welcome the opinions of others. This is the least obvious, but probably the most important. Because without humility, people who have talent and ambition are nightmares to work with, and tear the team apart.

I wanted to work in a company that only had great people, and I just couldn’t find it anywhere else, so I decided to build it. And let me tell you, it is great.

What was the the biggest surprise you found when you started your business?

How much easier it is than everybody says. Everybody makes it sound like it requires magic skills, contacts, money, expensive education, genius ideas, etc. In practice it just requires a decent idea to start, and a tremendous amount of hard work. Not to say starting a business is easy: far from it. But it’s much, much easier than people claim, and the amount of “inspiration” required is far less than the amount of “perspiration”. If you are able to work hard and avoid getting distracted by legions of people who are constantly trying to waste your time, you’ll do fine.

What was the hardest thing about getting started?

Confidence. Everybody around you wants you to fail, and thus will discourage you at every possible step of the way. Not outright, not overtly. But most people don’t try, and thus are relieved to see you fail as it reinforces their decision to keep going back to that job they hate, getting the paycheck they think is too small, working for the person they think is stupid.

What has been the most rewarding moment?

There are so many, it’s hard to pick. Just yesterday I was talking with one of my people, who was talking about how one of their people, was training one of their people, on how to let a candidate that they interviewed go. I realized at that moment that we had finally built a self-sustaining system of training the next generation of leaders in the company. Because the only way to get great people is to build them from scratch. You hire people with no experience right out of school, and heap as much responsibility as they can handle onto them as early as possible. Ultimately, technical skills are so much easier than leadership skills. It was incredibly rewarding to realize that we had created a self-reinforcing system of leadership development that didn’t involve me whatsoever.

What’s the one piece of advice you would give someone else about to start their own business?

Choose how much time every week you want to devote to starting your own business, and then start doing that. Even if you have no idea what to do. Just spend those hours every week trying to come up with an idea. Even if it’s just staring at a blank piece of paper, stare at it for that many hours. There’s no excuse to wait, except for the excuses you invent to fool yourself.

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