John Pepper Puts Down the Burritos and Picks Up Remote-Controlled Drones

The former Boloco CEO is taking his new hobby sky-high, all around the world.

Images via John Pepper's Drone

All photos provided by John Pepper’s Drone

When you step aside from managing one of the region’s most popular burrito chains, the next logical things to do are spend time with your family, go on trips around the world, and, of course, learn how to fly drones.

At least that’s what Boloco cofounder and former CEO John Pepper has been up to these days. “Since I was a kid I have been basically obsessed with flying,” said Pepper, who resigned from his post as the burrito company’s CEO in October. “When I saw there were commercial drones available that you could buy easily, and get them set up in the air pretty quickly, I bought one. All because I’m unemployed from my own company.”

But, as Pepper quickly found out, one drone turned into two, and two then turned into three.

That’s not to say he’s been collecting the unmanned flying objects, however. Instead, he’s been crashing them while testing their limits in the air, bringing them to spots that the naked eye would never be able to experience without the use of the emerging technology. “I lost two. I am on my third one now,” he said, adding that he’s getting ready to bring his newest drone to Central America, and later, Costa Rica, when he embarks on upcoming trips with his wife and kids.

Pepper’s obsession with drones, which can cost anywhere from $500 to $1,000 depending on the type, started in January during a New Year’s Eve party. Pepper said a friend brought the aerial vehicles to his attention during a conversation at the party, and right then and there he decided to buy one. Pepper said he opened up Amazon on his phone, found a suitable drone, and hit “purchase.”

Ever since he’s been flying high with his newfound hobby. “The fact that you could just fly this thing, and it could take pictures, and you could see those pictures from your iPhone—I started to think, ‘what could I actually do with that, what odd perspective could we get with that camera?’”

Following along on Pepper’s Instagram and YouTube accounts, where he posts videos and photos recounting his drone adventures, you can see shots of Dartmouth College, parts of Boston, and exotic island landscapes, all from hundreds of feet in the air. “The coolest shot I got, I started looking for things people haven’t seen before. So as you look at Dartmouth College, there’s a shot of the very top of the Baker Tower that you couldn’t get to see unless you had a helicopter,” he said. “Another cool shot I got was in the Caribbean with my kids. From that perspective, it’s just totally spectacular.”


Pepper has also taken his drones out to sea, but, that’s where he lost one of them. “When I got down to Florida, I was trying to get a close-up of the waves and trying to get the curl of the wave, or inside of the wave,” he said. “My dad was screaming, ‘you’re going to go in the water!’ As I tried to bring it back in, I hit down with the wrong button, and it went straight into the ocean.”

But that hasn’t stopped him from continuing to play around. Nor has the scrutiny of the accessibility of drones, and the pending legislation both state and federal elected officials have filed to regulate commercial and business use of the unmanned aerial objects (there are currently limited guidelines set by the Federal Aviation Administration about recreational use).

While drones have been a point of contention with many individuals, and have called attention to the possible breaches of people’s privacy, Pepper said his drone use isn’t nefarious or “creepy,” and he’s merely enjoying “being a kid” now that he’s no longer responsible for running Boloco’s day-to-day operations. “When you fill burritos for 17 years—I’m trying to make up for lost time. It seems borderline crazy, but I’m hitting my mid-40s bucket list pretty quickly,” he said. “I would say I’m pretty obsessed with it.”

Below are a few videos Pepper captured after sending one of his drones, “Wilson II,” into the air: