Jared Isaacman: From Business Aviation to Space

Jared Isaacman made his fortune by creating an online payments platform, and went from zero to hero in aviation (and now space) in a few years - all because he needed a hobby! Fabrizio Poli shares his story...

Fabrizio Poli  |  24th October 2022
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Fabrizio Poli
Fabrizio Poli

Fabrizio Poli is Senior Consultant at Orville Aviation. He is also an Airline Transport Pilot. Mr. Poli...

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Jared Isaacman and the Polaris Dawn team


When in kindergarten, Jared Isaacman told his teacher he would go to space someday – and she said she’d be watching.

Growing up he knew that the odds of becoming a NASA astronaut were very slim, but he wasn’t discouraged, always hoping that things would change one day.

As a ninth grader and a freshman, Jared discovered that he and his best friend, Brendan Lauber, had a talent for fixing computers and they started a computer repair business in his parents' basement called Deco Systems.

He had begun working, doing computer technical service and repair, aged 14. Two years later he got a job offer from one of his clients, which he accepted, dropping out of high school and obtaining a GED along the way.

By 1999, Isaacman was founding a retail payment processing company named United Bank Card, which was later renamed Harbortouch, a point-of-sale payment company based in Pennsylvania. By 2020, the company had been renamed Shift4 Payments with Jared being CEO.

The company was processing US$200bn in payments annually, with Shift4 handling payments for one-third of America’s restaurants and hotels, including the Hilton, Four Seasons, and KFC. Jared took it public in June 2020 and owns 38% of the stock.

Jared’s Path as an Aviator

Back in 2004, during the early days of his company, a 21-year-old Jared was living in his parents’ basement working around the clock and burning himself out.

He figured he needed a hobby – something to get him away from the office – and that’s when he took his interest in aviation to something tangible. Jared began flying Cessna 172s, and once he got his private pilot’s licence bought a Cessna Turbo 182. After 150 hours of flying, he upgraded to a twin-engine Beechcraft Baron, in which he earned his commercial, instrument, and multi-engine ratings.

He flew the Baron for about 700 hours over 18 months before stepping up again...

Before 2005, Jared had never been on a private jet because he’d never had the money. 

In fact, his motivation the first time he climbed aboard a private jet had nothing to do with business efficiency or time-savings. He was purely driven by his enthusiasm for aviation. But he soon discovered it was an efficient way to travel. 

Having chartered a Bombardier Learjet 35 to go to Tucson, Arizona for a meeting, he reasoned it would make sense to buy a company jet and learn to fly it himself. He chose a Cessna Citation CJ2.

Jared lives to take up new challenges, and in 2008 he made his first World Record attempt in a Light Jet – a round-the-world velocity record in his Citation CJ2 – missing the mark by just one hour after long ground holds in India and Japan. He didn’t give up, though, and on his second attempt he shattered the record by over 21 hours, completing the route in sixty-one hours, fifty-one minutes.

By breaking this record, Jared earned an 'Experimental Type' ranking allowing him to pilot L-39 Albatros and A-4 Skyhawk fighter jets, leading him to creating his own aerobatic squadron referred to as the Black Diamond Jet Team.

Jared teamed-up with five other pilots, and as a group they flew over 100 air show exhibits between 2011 and 2014, doing formation loops, rolls and other maneuvers, as well as flying just 18 inches apart.

Every time they sat down at the bar, the discussion turned to how they could not do air shows forever.

They brainstormed about how to pivot from something they enjoyed so much, to something that had real commercial opportunity but was safer – and  the idea of ‘commercial adversaries’ was conceived.

They realized they could buy fighter jets from all over the world: A-4 Skyhawks right out of Top Gun; MiG-21s; F-16s from New Zealand, the Czech Republic, Spain, Israel, and more. They could offer the government four or five planes in the air at one time for the same cost as flying just one F-16.

In 2012, Drakken International was born, and by 2016 the business had grown to $6bn. Drakken currently has close to 100 fighter jets, and a high-margin, profitable business model. Jared sold part of his stake in Drakken to Wall Street firm Blackstone for a nine-figure sum in 2019.

Next Step, Space

Indeed, Jared was aiming even higher. He approached Elon Musk, and in 2021 bought an entire passenger flight from SpaceX. Taking three others with him on the world’s first all-civilian spaceflight to orbit, the mission, called Inspiration4, raised more than $243m for St. Jude’s Children's Research Hospital, and is featured in the Netflix show, Countdown: Inspiration4 Mission To Space.

But Jared hasn’t stopped at one space flight. His new adventure, the Polaris program, was announced just recently, that will take Jared into space another three times.

The first flight, called Polaris Dawn, will feature Commander Jared Isaacman, as the Mission Leader, and three passengers, who will spend five days in orbit.

The purpose of these missions is to present how non-government astronauts may very well be productive in space. Now that the door is open, there’s a lot to build, really opening this frontier. Polaris – a joint program with SpaceX – is a sequence of technically-demanding developmental missions that can conclude with the primary flight of the brand-new launch rocket, Starship.

Assembling two proficient engineers at SpaceX in Sarah Gillis, the SpaceX lead astronaut coach, and Anna Menon, a SpaceX managing engineer and mission director of mission management, who beforehand worked as a biomedical operator at NASA, Jared added, Scott Poteet, who he flew with for over a decade in the air shows and at Drakken. Scott was also the mission director for Inspiration4.

The next two missions after Polaris Dawn will be Polaris II and III. Polaris II's objectives will be based mostly on what is learnt from Polaris Dawn, and the un-crewed check-flights of Starship. If profitable, Starship would be a spaceship that can return humans to the Moon, and finally carry the first people to Mars.

When Conquering Space Helps Business on Earth

While Jared has been busy conquering space, Shift4 is expanding its reach on Earth, and to do that Jared has been flying his Bombardier Global XRS back and forth from the US to Europe, allowing him time to train for space while still building his business.

With all the media attention on Jared’s space endeavors, Shift4 has taken the opportunity to branch out internationally. In March 2022 Shift4 (NYSE: FOUR), announced that it will acquire both Finara, a cross-border eCommerce payments provider with a large European presence, and The Giving Block, which specializes in cryptocurrency fundraising for non-profits.

These acquisitions better position Shift4 to pursue a multi-trillion-dollar addressable market across the world, including accelerating growth in eCommerce, gaming, stadiums, restaurants, hospitality, specialty retail, charitable giving, and a new capability with cryptocurrency enablement.

Jared explains, “Cryptocurrency is quickly moving beyond early adoption and becoming increasingly mainstream as more people want to invest, transact and donate in crypto”. Shift4 intends to be at the forefront of this movement and leverage The Giving Block technology across the entire enterprise.

These two acquisitions are expected to contribute over $15bn of end-to-end payment volume and $35m of adjusted EBITDA in 2023.

Success is About Learning to Handle Fear

When asked about success Jared says it is about learning how to handle fear. “You compartmentalize, focus on what you can do not to get hurt or die,” he observes. “Right now, I’m training for [Polaris Dawn] six months from now.

“How I perform during that training and the knowledge I accumulate will help if I have a ‘moment’. I’ll know what to do tactically. “If you’re flying an airplane and it stalls, it’s going to hit the ground if you do nothing – so you remove fear of hitting the ground from the equation, then do what you need to recover. Preparation is part of it, then compartmentalizing, then doing everything tactically that you can to mitigate a possible bad outcome.

“Also, I don’t take unnecessary risks,” he shares. “A few of my air show buddies started riding motorcycles. I tried it for two days, and thought, ‘I’m going to kill myself on this thing. It’s not compatible with my skill set’. You have to know your limitations.”

I guess it’s fair to conclude that knowing your limitations, and taking things one step at a time, you can truly go to infinity and beyond!

Read more about the positive impact of private jets on businesses

More information from www.bizjettv.com


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