5 Tips for Entrepreneurs From Expensify CEO David Barrett


A few years ago, David Barrett took a homeless man to McDonald’s. “It’s an experience I recommend doing precisely once,” he said. “It’s really awkward.”

He was living in San Francisco at the time, working for a prosperous up-and-coming tech company and walking around with significantly more money in his virtual pockets than he was used to walking around with.

Being a kind and generous man, he wanted to use his newfound wealth to help feed the homeless. He just didn’t want to do it by inviting each homeless person individually to McDonald’s.

That’s when David had an idea. Not a great idea, in retrospect, but an idea nonetheless. He would supply the local homeless population with zero-balance debit cards that only worked at specific restaurants. Feeling confident, he took this idea to the bank.

Unsurprisingly, they turned him away.

But, by then, David had caught the entrepreneurial bug. He thought to himself, “Fine, that idea won’t work — what’s the most low-risk and boring business I can get into? Ah-ha! Expense reports!”

He went back to the bank and presented his new plan: a zero-balance debit card business owners could give to their employees. “Oh, and there would be a mobile app with a bunch of cool features and yadda, yadda, yadda. I really had no intention of doing any of that,” he later admitted, “but I needed something that would sound good enough to get the support of the banks.”

And support him they did. But, as it turns out, that mobile expense reporting app that Barrett had no intention of creating was the one thing people wanted the most. Thus, Expensify (and, yes, the Expensify mobile app) was born.

Since then, Expensify has dominated the expense reports industry, and CEO David Barrett has dominated headlines with his unorthodox business management strategies.

… And we were lucky enough to pick his brain during his recent visit to TSheets HQ. We asked him, “What’s your advice for small business owners?” This is what he had to say.


1. Don’t read business books.

“I hate business books,” Barrett said. “When I read books, I’m not reading them to get ideas, I’m reading them for inspiration — and it’s so much easier to be inspired by fictional characters.”

With that in mind, he recommends trading in your copy of “Who Moved My Cheese?” for something a little more inspiring — like “Starship Troopers.”

“I love science fiction books,” he said, “especially those from the 1950s. That was the height of American power. Everything was so optimistic and futuristic. There’s nothing like it.”

His top three picks:

  1. “Anything by Heinlein.” (See Heinlein’s published works on Amazon.)
  2. “Starship Troopers” by Robert Heinlein (“Just don’t pay attention to the movie.”)
  3. 20,000 Leagues Under the Sea” by Jules Verne


2. Dumpster dive for good ideas

“A good idea, by definition, has to sound bad,” Barrett said. “If a good idea doesn’t sound bad, it wouldn’t be a good idea — it would just be the thing that everyone does.” For Barrett, brainstorming good ideas can be compared to dumpster diving.

“You have to find the hidden treasure that’s been overlooked or tossed out by the person who came before,” he said. “And usually it’s been tossed out for good reason — like it really, really stinks. Like any good idea, there has to be some reason other people haven’t already found it. So the challenge is to take this piece of trash and convince everyone else that it’s a great idea.”

Take Expensify, for example. “Everyone thought expense reports were boring,” he said. “They thought the industry was already dominated and nothing more could be done … But they didn’t realize the impact the mobile app would have.”

Barrett had what many would consider a bad idea. But he saw why it had been tossed aside and turned one man’s trash into a very profitable and successful treasure.

“Don’t get me wrong,” he warns. “Not all terrible ideas are good. In fact, most are actually terrible … but not all of them. You have to be willing to dumpster dive.”


3. Get rid of your double-monitors

“I know what you’re thinking,” Barrett said. “’Why is he ripping on my monitors? I love my monitors!’ And that’s fine. But when you have two big-ass monitors on your desk, your entire world becomes your monitors. You can’t see anything else.”

Those monitors, your desks, your cubicles, or your office doors create physical walls that say, “we’re not part of the same team.” And that’s not what Barrett wants for his employees.

He believes in creating a truly open and truly flat workspace. “No walls, no cubicles, no desks,” he said, “and definitely no giant monitors.”

At Expensify, employees sit together in a large room — in a new seat each day. “It gives us the ability to sit down and work with whomever we want or need to work with in that moment,” he said. “It’s a team dynamic we could never achieve if we all claimed our own turf and sat next to the same two people day after day.”

This strategy won’t work for everyone, but Barrett makes an important point: Look for ways to make collaboration easier for your team.


4. Don’t divide and conquer, conquer as one

Expensify has offices in San Francisco, Portland, rural Michigan, Melbourne, London, and more. “It’s a challenge to keep everyone thinking of themselves as a part of the Expensify team as a whole,” Barrett admits. “They’re not just ‘the London branch’ or ‘the Portland branch.’ They’re part of the Expensify team, and we’re all working together towards the same goal.”

How does he keep his team operating as one?

“It helps to remind them of that team mentality from time to time,” Barrett said, “and I always encourage them to work on the same frequency.”

For example, Barrett noticed that his employees were creating different communication channels in Slack, a popular chat app. “Everyone started making different channels,” he said. “There would be a channel for ‘social’ and suddenly there was another channel for ‘UK social.’ It’s a minor thing, but it still creates virtual walls that separate the US social team and the UK social team.”

His team claimed they didn’t want to bother other teams with chats that may not be relevant to them. Barrett responded, “You’re talking about bagels — this isn’t relevant to anyone!”

That brings us to our final tip.


5. Talk about bagels

Sometimes, those inane conversations about bagels (or last night’s “Game of Thrones” episode) open the door for other more important conversations. And Barrett agrees.

“I’ve noticed that I’m way more likely to get a bunch of direct messages with important questions after I’ve said something like, “I love bagels,” in Slack,” Barrett said. “And I know they wouldn’t have pinged me with those questions if I didn’t share my genius bagel comment.

“Those conversations connect you with the others on your team. Saying ‘I like bagels’ is a roundabout way of saying ‘Hey, I’m here, and even though we don’t work in the same office, we do work together in the same company and we exist in the same universe.'”

So, go ahead, talk about bagels. Talk about “Game of Thrones” or which bear is best or who you think is going to the Super Bowl this year. Those conversations, while not always relevant to the task at hand, are of the utmost importance for team-building and camaraderie.


Have any unorthodox business tips of your own? 
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