Kenn Ricci grew up as the son of a government worker in South Euclid, a suburb of Cleveland, Ohio – what he himself describes as “a very, very poor family”. He got furloughed from his first real job and moved back in with his parents. Today, Ricci chairs a private aviation empire valued at $4 billion and has donated $100 million to his alma mater in a single cheque. However, if you ask Ricci how it happened, he will tell you “it was an accident”.
From Notre Dame to a furlough – and a $27,500 bet
According to the Wall Street Journal, Ricci enrolled at the University of Notre Dame, joining its Air Force ROTC program where he made his first solo flight and earned both his private and commercial pilot licenses.
He graduated with an accounting degree, served in the Air Force, and landed what seemed like the dream job – a position with Northwest Orient Airlines. It did not last.
“I worked for Northwest Orient for a brief period of time. I get furloughed. Unemployed, back living with my parents,” he told the Wall Street Journal.
Rather than wait for another airline to call, Ricci did something that in hindsight looks like genius but at the time looked like desperation. As per WSJ, in 1981 he used a bank loan to buy Corporate Wings – a small aircraft management and charter company – for $27,500.
Annual revenues grew from $300,000 to approximately $3.4 million between 1981 and 1985, landing the company on the Inc. 500 list of America’s fastest-growing businesses. During those years, Ricci was personally flying 600 to 700 hours a year – taking on concert tours, corporate clients, and political campaigns.
One of those clients was Arkansas Governor Bill Clinton, whom he flew throughout the 1992 presidential campaign. His private assessment at the time was not exactly prophetic. “I said, ‘The governor of Arkansas is not going to need a plane for 13 months. This guy has no chance of becoming president,'” he recalled to WSJ. “And then I flew him to the inauguration.”
Flight Options, a painful exit, and an empire called Flexjet
Ricci’s first real taste of significant wealth came when he sold Inertial Airline Services for $10 million according to Fortune. But the bigger swing came in 1998, when he founded Flight Options – built on the then-novel idea of selling fractional shares of pre-owned aircraft, going head-to-head with NetJets, which was selling fractional shares of new ones.
Revenues grew from $35 million to $300 million in just 17 months as per multiple reports. Flight Options eventually merged with Raytheon Travel Air, which bought him out – a deal Ricci later described as one of the worst days of his life.
Undeterred, he went on to found Directional Aviation Capital and acquired Flexjet, which according to Fortune raked in $3.8 billion in revenue and has since been valued at $4 billion following investment from a private equity firm associated with LVMH.
“I am accidentally wealthy”
Despite four decades of deal-making and empire-building, Ricci has never reframed his story as one of grand ambition. He remains characteristically grounded: “I am accidentally wealthy,” he has said, insisting that his motivation was never money but passion, and that the fortune is simply the byproduct of doing what he loved for long enough.
In 2017, that gratitude took a concrete form – he donated $100 million to Notre Dame, the largest unrestricted gift in the university’s history according to an official announcement by the university itself.
From a furloughed pilot living with his parents to the chairman of a $4 billion aviation empire – all by accident, apparently.