“I worked for [airline] Northwest Orient for a brief period of time. I get furloughed. Unemployed, back living with my parents,” Ricci told the Wall Street Journal in a recent interview when reminiscing on how he made his first $1 million.

But, instead of throwing in the towel, he saw a golden opportunity. Ricci took a contract pilot job at Professional Flight Crews, and one of the companies he flew for was private aviation company Corporate Wings. The budding businessman was intrigued when its owners put the business up for sale at $27,500 in 1981—and jumped on the opportunity to buy it. 

Ricci scraped together a $27,000 loan, but still came up $500 short. So he picked up the phone and called his father for the rest—and that call would launch his career in entrepreneurship.

By the early 1990s, his company was pulling in $3 million a year. Ricci took Corporate Wings to new heights, literally, flying artists like Barbara Streisand and Elton John on tour jets. But the real big break came when an Arkansas governor running for president needed a plane for a little over a year. That political hopeful wound up becoming the 42nd president of the United States: Bill Clinton. 

“I said, ‘The governor of Arkansas is not going to need a plane for 13 months. This guy has no chance of becoming president.’ And then I flew him to the inauguration,” Ricci recalled.

From humble beginnings to a billionaire lifestyle with $800,000 vacations and a $2.5 million watch collection

Corporate Wings was just the opening act in Ricci’s four-decade streak of business triumphs. 

In 1990, he launched Inertial Airline Services and Flight Options—with Flight Options pulling in $100 million in just its first three months. Sensing the goldmine he’d built, Ricci sold Inertial Airline Services for $10 million: his first real taste of “significant wealth.” Flight Options eventually merged with aerospace defense giant Raytheon, which bought him out on what he later described as one of the “worst days” of his life. But setbacks never stick: he went on to found Directional Aviation Capital (DAC), investing in aviation companies and scoring a massive win when DAC acquired Flexjet, raking in a jaw-dropping $3.8 billion in revenue last year.

From the humble son of a government worker in “a very, very poor family,” Ricci’s relentless drive in aviation catapulted him to billionaire status.

Now, the aviation boss says his whole life is like a vacation—and when asked how much he splurges on actual getaways, it’s a figure that’s jaw-dropping to most. Ricci spends six weeks in Italy with his family, dropping between $750,000 to $800,000 for the lavish trip. 

“I have way too many homes, and I spend way too much on travel,” Ricci said in the WSJ interview. “It might sound like a big number, but it more has to do with just the fact that if I’m going to go somewhere, I want to enjoy it. I want it to be the best experience it could be.”

The billionaire revealed he regularly shells out on big tips for workers at his vacation spots, giving $1,000 upfront to restaurant workers when visiting for the first time. At the hotels he frequents, he’ll drop “10 times that” at the start so staffers know what “level of expectation” he has. Ricci always wants his trips to be the best experience possible. 

The Flexjet chairman also likes to celebrate success with fine watches, similar to Tom Brady and Mark Zuckerberg. Any time something “important happens” in his life, he’ll shell out on another one. To date, he’s racked up a $2.5 million collection of around 40 watches—with the most expensive single purchase setting him back $150,000.

“The first company I sold, I bought myself a watch. And so over the years, it’s not so much that I love watches, but I associate a watch with a memory of something financial when we have a success.”