Photo via flexjet.com
Kenn Ricci, chairman and largest shareholder of Flexjet, told David Senra on his podcast that he got into the jet business in 1985 by buying a small Cleveland charter company for $27,500, most of it the company's own cash.
Most founders who lose control of a company do not get it back. Kenn was bought out by Raytheon in 2002 and bought the business back in December 2008, in the depths of the financial crisis, after Raytheon had lost roughly $600 million running it.
"I'm accidentally wealthy. I didn't get here with some strategic, some monetary plan, financial plan."
Kenn built Flight Options as a used-jet rival to NetJets, bought the Flexjet brand from Bombardier in 2014 and now runs a fleet of more than 365 aircraft.
The full interview is covered here so you can skip it. 1 hour 11 minutes of audio, 10 minutes of reading.
Here are the 10 moments that matter.
David Senra · Oct 28, 2026 · 1h 11m · 61m saved
With Kenn Ricci, Chairman and Largest Shareholder of Flexjet
Key Takeaways
Kenn bought his first charter company for $27,500 to keep his own flying job
Warren Buffett's $750 million purchase of NetJets in 1998 is what got banks to lend to fractional jet companies
Kenn raised nearly $300 million that summer after 35 to 40 banks had turned him down
Kenn lost control of Flight Options to Raytheon in 2002 and bought it back in December 2008 for $135 million
Raytheon had lost about $600 million running it
Mergers that add 30% to 40% to a workforce destroy the culture, which is why Kenn has avoided them since
About 70 of Flexjet's 365 jets are never sold and exist to cover peak demand
The US flies 85% of the world's private jets, so Flexjet has no Asia strategy
Kenn gave his children their wealth while they were young, rejecting trusts that pay out at set ages
1. A $27,500 Buy to Keep Flying
Kenn learned to fly through Navy and then Air Force ROTC at Notre Dame. On his father's advice he went to law school, but kept flying part-time. In 1985 he bought J&J Aviation, a small Cleveland charter outfit riddled with fraud, for $27,500. The company's own cash covered $27,000 of the price, and his father lent him the rest.
Kenn bought the charter company to protect his own pilot's job, not as an investment
"I bought it so I could still have a job. I needed to make sure these airplanes didn't go away so I could keep flying." — Kenn Ricci
He renamed the business Corporate Wings and kept its four remaining planes in the air. Its niche was touring musicians. Kenn persuaded jet owners to finance large-cabin aircraft in exchange for three months a year of tour charter revenue, and Richard Branson later became a client as well.
Corporate Wings' early clients were touring musicians who needed large-cabin jets
"I flew Elton John, Bryan Adams, Bruce Springsteen, Tony Bennett, Barbra Streisand. Those were my clients." — Kenn Ricci
That arrangement grew the fleet Kenn managed into the low 20s.
