Expensify CEO David Barrett: ‘Most CEOs are not bad people, they're just cowards’

The Trump presidency ends tomorrow. It's a political change in which Expensify founder and CEO David Barrett played a brief, but explosive role.

Barrett became famous last fall — or infamous, depending on whom you ask — for sending an email to the fintech startup's clients, urging them to reject Trump and support President-elect Joe Biden.

"Anything less than a vote for Biden is a vote against democracy," Barrett said in the email.

It was an unprecedented political maneuver by a CEO-founder in Silicon Valley, and one that drew praise from a preeminent historian of the region.

"This was a moment that utterly transcended politics as usual, and his statement utterly transcended politics as usual," futurist and historian Paul Saffo told Protocol. "I'm sure investors got a little bit of a case of indigestion over this. It was a bold move and I would say it was made with considerable character."

And it wasn't a one-off: Barrett sent another email to Expensify customers over the weekend, telling its users about its plans to spend $3 million on fighting inequality, while also railing against the "domestic terrorists" who invaded the Capitol earlier this month.

Barrett talked to Protocol last Friday, before the latest email, about the coming transition, which he reflected on in a celebratory mood even as he looked back on the controversial episode. "We just survived Trump. This is going to be an amazing year," he said. "The economy's coming back. The vaccines are rolling out. Travel is going to restart. We got a new administration that's going to make reasonable decisions. We avoided a civil war. Everything's on the up and up."

The interview has been edited for clarity and brevity.

You sent that email taking a position on the election. I've talked to a lot of CEOs in Silicon Valley who'd rather stay in the middle. They're not going to say what they think or even who they voted for because it's safer.

My opinion is a little bit different. I think this idea of "Oh, we're apolitical," I think that's kind of bullshit. I think there's no such thing in a democracy as being apolitical. Every action you take is your position. I think that a large number of these tech companies, by saying, "Oh, we're apolitical," that's a very convenient way of saying, "No, I'm voting for the status quo. I support the current administration, and I'm not going to take actions to do anything about it because it's actually good for business." I think it's actually pretty cynical.

There's going to be a change, and there will be new issues. It's probably not going to be as intense as Trump, but there will be issues. How do you navigate them? It can be a slippery slope when you start to take positions.

I think the litmus test is: What is the real-world potential impact of this? I don't anticipate to weigh in on the normal issues. It sounded bombastic back then when I wrote the newsletter: "Hey, I am genuinely concerned that we're going to have a true civil war, and that's going to be really bad for business. My business is great. We're profitable. We're growing. We're surviving the pandemic. So long as we don't descend into civil war, we'll be fine. But Trump is saying he's not going to leave office, and is anyone reading this crazy shit? We should take it seriously."

This is not normal politics. This is not taxes or health care or whatever. This is like the destruction of our nation up for discussion. The only reason I felt it was important as a CEO to weigh in was that the stakes are too high to be neutral here.

Even right now. The guy's still not out of office, by the way. The FBI's warning that we're going to have attacks on every state Capitol. Never has that happened in the history of the nation before. This is so wild, what we're talking about.

I feel that we need to keep reminding ourselves just how beyond the pale this is. As business leaders, it's just shameful to just sit out this entire thing. It's like, "Oh, remember that one time when we almost had civil war? What did you do about it? Oh, fucking nothing? Oh, good job."

What was the reaction to the email like? Did any of it give you pause?

Expensify is not a product you adopt overnight. You also don't leave it overnight. We just didn't know what the reaction was going to be. We saw this thing just go so much bigger than we expected. We were like, "Oh, fuck. OK. That's exciting."

Most people ignored it, or agreed with it, or vented about it or whatever. The vast majority of people, they're too busy. And in this Twitter news cycle, sustaining anger for more than like 10 seconds is hard. It's like, "Fuck Trump! Oh, such a cute puppy!" It's so hard to do anything.

Where does that come from, that belief in taking a position? Can you talk a bit about your background?

My background has always been in hard engineering. Never been in finance. Never been in politics or any of that stuff. I think what you're getting at [is]: Why are you so outspoken? I'm in a lucky position to do that. I run a very profitable business that has a very distributed customer base.

I think most CEOs, it's not that they're bad people, they're just cowards. They're like, "Yeah, I would like to take a stand, but I can't because of investors, customers and things like this." It basically comes down to, "I care more about hitting the next quarter results than preventing a civil war," which is so fucked up. They're more afraid of their investors than they are of militants. I'm in a lucky position where I don't have to be afraid of my investors. I'm super profitable. I can't get fired. There's no majority on the board that can fire me. So I think that I am in a position [where] I can take these stands much more than others.

I've heard from a lot of other CEOs [about speaking up, and they say]: "I can't. I wish I could. I feel bad. I feel ashamed. But I kind of can't." I feel I can give an example of, like, "Guys, speak up. The water's fine." Defending democracy is not actually a bold choice because most people agree with it.

Sure, we got a lot of shit on Twitter, or whatever. Those people weren't our customers anyway. It had no negative impact on revenue. If anything, I think we're gonna look back and this is going to be an incredible brand building event. We didn't expect this to go as viral as it did. It's like, "Shocker! Getting massive coverage for defending democracy is good for business, actually."

I think that CEOs need to have the courage to actually step up for things that matter, and be less sort of afraid of the impact on their businesses. Because most customers, especially the people who are actually buying the software, they care about stability, they care about democracy.

Would you consider politics after your business career?

No, that sounds like a huge pain in the ass. Plus that assumes that there is an "after my business career." I just made this giant profitable business, and it's fucking awesome. I want to work here forever. My goal is just to stay here forever.