Editor's Note: This article is part of a series that celebrates the Inc. 500 founders for whom good enough isn't good enough, the ones who blast past what everyone else thinks are boundaries.
Jared Isaacman took up flying in 2004 because he "needed an escape from my day job," which was running Harbortouch, a company that sells card readers and processes payments for retailers. One thing (prop planes) led him to another (corporate jets) and then to another (surplus military jets), culminating in 2012 with the founding of Draken International, a Lakeland, Florida, military contractor that operates one of the largest fleets of privately owned fighter jets in the world. Every day, most often in the lonely skies high above the Nevada desert, Draken employees help train U.S. military pilots in aerial combat--"simulating everything that should happen," Isaacman says, "short of shooting each other." Isaacman still flies. He was the right-wing pilot in a recent air show flyover at Disney World. "Unfortunately, I don't do as much upside-down flying as I used to," he says. "Just too busy." Here's how the 34-year-old entrepreneur handles juggling two fast-growth companies. --As told to David Whitford
I guess the easy answer is I genuinely love both businesses. If you love it, you don't mind working. I don't play golf or have sports hobbies. Just my two businesses and my family.
Harbortouch is in Allentown, Pennsylvania, and Draken is headquartered in Lakeland, Florida, but most of Draken's operations are based out of Las Vegas at Nellis Air Force Base. I'm always on the road, probably home one week a month. Every day is a 16-hour day. I tend to do more of the Draken work at night and during the weekends. Sometimes I'll work a full day, take off from Allentown to Spain for a meeting, and then fly right back. It's a little chaotic and contributes to sleep deprivation but we get the job done. Harbortouch gets everything it needs and Draken does as well.
I don't have a COO at either business. Both organizations have about seven VPs who are direct reports. I stay pretty engaged with all the tiers down from that. I'm not big on chain of command. I used to do a whole lot more flying. Now I'm sitting in the back with my laptop more and trying to catch some rest. My 3-year-old daughter told my wife she doesn't think I'm a pilot anymore because I don't fly. That was crushing.
From August through September, I was home only three days. As someone who flew in lots of airshows in his 20s, I know what immortal feels like. That's not what I feel like now. I know it's not sustainable. Definitely takes a toll on my health. But I have so much invested in both business. I love watching two interesting businesses mature, both with disruptive features. If the game is on, I want to play in it. I want to have the ball.