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How Jared Isaacman Will Make Us Interplanetary
Methods of Prosperity newsletter no. 125: Jared Isaacman
Sean Allen Fenn
November 06, 2025
I have had the privilege throughout my career of observing many great companies through both the lens of an operator and investor. In that time, I have tried to distill all of the details into a simple list of what really drives success – and I use these criteria before making any investment decision.”
Many entrepreneurs compete on price, avoiding difficult problems.
Not Jared Isaacman.
He went out of his way to pursue complexity as a competitive advantage.
And he was only 16 years old when he founded Shift4 Payments. It’s a major payment processing company he started in 1999 from his parents’ basement.
Not only was it self-funded, but it turned a profit for 15 years (1999-2014).
American billionaire entrepreneur, accomplished pilot, and private astronaut, Jared Isaacman.
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Most tech entrepreneurs, especially in payments/fintech, raise VC early. They want to fuel rapid growth.
They give up equity and incremental control through multiple funding rounds.
They face pressure from investors to exit or go public on their timeline.
They never achieve true financial independence until a successful exit.
Not Jared Isaacman.
He held complete control for 15 years.
He gained financial freedom before ever taking outside money.
He possessed negotiating power when he finally did need capital.
His company accepted external capital in 2014.
He needed $250 million to acquire his former client/employer, Merchant Services. That’s why he only sold a 53.5% stake for $279 million.
Shift4 Payments grew to process annual transactions of over $200 billion.
He took the company public in 2020 at a $2.8 billion valuation.
“My base salary going forward will be consistent with a typical entry-level manager… it is my expectation that the financial successes from operating Shift4 as a public company will come to me much in the same way as they always have over the past 20 years: as a stockholder in the business.”
Isaacman maintained 31.5%+ ownership even after going public.
Shift4 Payments has a market cap of $6.65 billion as of October 28, 2025.
“Shift4 wins because our ‘true north’ is to seek out complexity and simplify it.”
This gave him the ability to pursue other ventures.
He co-founded Draken International. It’s a defense aerospace company providing adversary training for the U.S. military and NATO. Draken International operates one of the largest private fleets of fighter jets.
It’s one thing to be a 42-year-old American billionaire entrepreneur.
Isaacman is also an accomplished pilot. He is flight-qualified in multiple military jets, with over 7,000 flight hours. He’s well known for his call sign, “Rook”. He broke the world record for circumnavigating the globe in a light jet in 2009.
Why not be a private astronaut as well?
Isaacman has been a close collaborator and ally of Elon Musk. He bought several chartered flights aboard SpaceX. He facilitated partnerships between SpaceX and his own companies. Isaacman has flown twice to orbit aboard SpaceX rockets. He pioneered the first-ever commercial spacewalk in 2024. He commanded both the Inspiration4 and Polaris Dawn missions. These were historic private spaceflights, carried out with SpaceX. They advanced commercial astronautics and fundraising for St. Jude Children’s Research Hospital.
Isaacman was born in Union, New Jersey in 1983, dropped out of high school at 15, and later completed a GED. He was recently re-nominated by President Trump to lead NASA as its administrator. His estimated net worth is around $1.4–$1.9 billion as of 2025.
In conclusion, Isaacman built his wealth as an owner.
He chose to do it this way rather than as a hired CEO answering to venture capitalists.
This is his method of prosperity. Isaacman spends hundreds of millions on SpaceX missions and space exploration. He does it while still leading his company.
I like you,
– Sean Allen Fenn
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