Thrill seeker Jared Isaacman made a small fortune training fighter pilots but his wealth soared this summer when he took his payments processing business public amid the pandemic
Thrill seeker Jared Isaacman made a small fortune training fighter pilots but his wealth soared this summer when he took his payments processing business public amid the pandemic.to say that everyone has a “useful fatigue life,” to use Air Force jargon. That’s literally the number of flight hours left in a fighter jet before it outlives its usefulness and needs to be retired from service. But Isaacman views the concept as a metaphor for how to live his life.
For fun, Isaacman bullets the MiG faster than the speed of sound and climbs mountains to unwind from nonstop, intense 80-plus-hour weeks. He spent New Year’s Day in Antarctica scaling Mt. Vinson, a 16,000-foot wall of snow and ice 800 miles from the South Pole. He had to turn back 500 feet from the summit due to dehydration, but he vows to try again.saacman has been chasing an adrenaline rush since childhood.
Six months into his job at MSI, he decided he could make the process faster, easier and cheaper. So he quit to start United Bank Card, the progenitor of Shift4, in his parents’ basement. His first hire was his father, Don, who would soon leave his sales job as vice president of a home-security company. Using his connections from MSI and a $10,000 loan from his grandfather, Isaacman convinced a bank to give him an identification number, which he needed to sell the credit-card terminals.
At the same time, he was burning out from years of work building the company from scratch. So he decided to take up a hobby: aviation. He started out flying prop planes, but within two years he wanted more—so he put in hundreds of flight hours to move up to flying jets.
Isaacman sunk money into Draken to buy dozens of fighter jets from around the world, with minimal investment from friends and former colleagues. Douglas A-4 Skyhawks from New Zealand. Atlas Cheetahs from South Africa. Aero L-159s from the Czech Republic. They eventually assembled 100 jets, the world’s largest private fleet of military aircraft.
In 2014, an opportunity emerged that was too good to pass up: His old employer, MSI, was looking for a buyer. Isaacman, who had bootstrapped his payments company for 15 years, sold a 53.5% stake in the business to private equity firm Prospect Capital for $279 million in equity and debt. He then used the cash to buy MSI for around $250 million.“There are very few people who get that chance to fly a fighter jet as a civilian. It is extremely rare. It’s just a testament to his desire and passion.
His old high school friend wasn’t surprised. “He’s the best at what he does, and he’s proven it in totally different industries, starting from zero,” Lauber says. “His personality is ‘see it, conquer it and be the best at it.’ ”with a nine-digit net worth and grand visions of an IPO. The company had reported record revenues of $731 million, though it was still losing money. Then came major, unexpected turbulence.
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