Name: Private Jet Entrepreneur Got His Start Flying Barbra Streisand and Bill Clinton
Uploaded: 2026-01-11T17:45:00Z
Duration: 10 min 20 s
Description: Kenn Ricci, chairman of Flexjet, made a prescient bet on the rise of the ultra-rich—and in the process became a billionaire himself. He sat down with WSJ’s Gunjan Banerji to discuss how he built his private-jet empire from a $27,000 bet in 1983, and how he spends his fortune today.

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Kenn Ricci, chairman of Flexjet, made a prescient bet on the rise of the ultra-rich—and in the process became a billionaire himself. He sat down with WSJ’s Gunjan Banerji to discuss how he built his private-jet empire from a $27,000 bet in 1983, and how he spends his fortune today. Photo Illustration: Nikki Walker

https://m.wsj.net/video/20260111/c06cac24-584f-4a2d-9a3b-ce204d30c4af/2/hls/manifest-hd-wifi.m3u8

Kenn Ricci, chairman of Flexjet, made a prescient bet on the rise of the ultra-rich—and in the process became a billionaire himself. He sat down with WSJ’s Gunjan Banerji to discuss how he built his private-jet empire from a $27,000 bet in 1983, and how he spends his fortune today.

Private Jet Entrepreneur Got His Start Flying Barbra Streisand and Bill Clinton

I'm not waiting till I die. I wanna watch my kids enjoy their wealth.

When did you personally hit a billion dollars?

When the business was probably doing-

Did it make you want to get rich?

No.

Really?

I had done Barbara Streisand, Elton John. I said, this guy has no chance of becoming president. And then I flew to the inauguration.

Kenn Ricci is the man behind an empire of private jet companies, including Flexjet. He doesn't just cater to the 0.1% club, he's a card carrying member with a net worth above a billion dollars. As the number of ultra wealthy people surges to a record high, Kenn is betting on increased demand. Today, we're gonna break down how he got here and reveal what spending in that tax bracket actually looks like. So let's go back to the beginning.

Okay.

I wanna hear how you made your first million.

So come out of the Air Force. I worked for Northwest Orient for a brief period of time. I get furloughed. Unemployed, back living with my parents. I put myself out as a contract pilot called Professional Flight Crews. One of the companies I was flying for was called Corporate Wings. They ended up wanting to sell the company and I bought the company for $27,500.

I bet you're wondering where did he even get that $27,500 to buy that company in the first place? Here's how. Kenn noticed that the company had $27,000 of cash on its books. So he bought the company with a loan and used that money to pay back later. And the last $500, he called his dad to see if he'd spot him. I'll let Kenn fill you in on how that paid off.

By the early '90s, it's doing 3 million a year in revenue. I morphed Corporate Wings to be servicing concert tours. I had done Barbara Streisand, Elton John, and that's when one of the companies that I had contracted with said, "Have you ever done a political campaign?" So I asked them right away, well, how long is the campaign? And they said, "It's 13 months." Well that's a really good contract. And I said, well, what's the guy running for? He says, "We're running for president." And I said, well, who is it? He said, "Well, it's the governor of Arkansas." I said, the governor of Arkansas is not gonna need a plane for 13 months. This guy has no chance of becoming president. And then I flew to the inauguration. Coming out of Clinton, the company started to gain traction where I needed more and more employees.

Okay.

And that's when I started to grow the business.

Around that same time, another private jet company, NetJets was gaining ground.

I'm starting to think about what's the product I can have that compete with NetJets? And that's when I came up with the idea of Flight Options. So in '97, I'm out trying to raise 30, 40, $50 million to underwrite this idea, nobody was having it. And then in the summer of 1998, Warren Buffett buys NetJets and my proposal just happened to be on everybody's doorstep. I was the last guy there. In the summer of '98, and I had 50 million from Boeing, 50 million from Bombardier. I mean, it was amazing the amount of $50 million lines of credit I had because Buffett endorsed the industry. But concurrent with that, I had started the inertial navigation company.

Wow.

By having aftermarket repairs of this very particular device, I would've never known to start that business if I wasn't in the cockpit trying to understand how it fails.

He's talking about this company, Inertial Airline Services, which he started in 1990 after he saw how expensive it was to fix airline navigation systems. But then his company Flight Options took off.

We did a hundred million dollars in the first three months and then I realized I can't rate run any other company. That's why I sold the inertial navigation company the following year for like around $10 million. So that was probably the first significant wealth of any size.

At this point, Kenn was aggressively competing with NetJets and in 2002, his company merged with Raytheon and I bet that it would accelerate his business.

We merged the two companies, 50% to Flight Options, and 50% went to Raytheon, which was the owner of Traveler at the time. And I dunno if you're familiar with shareholders roulette, when you have 50-50 owners, one person puts a number out there and the other person either gets to buy or sell at that number. So I had the obligation to present Raytheon with the number within 18 months of the closing. I had gotten the valuation underwritten by Warburg Pincus for $360 million. I offer Raytheon 180 million for their half of the business. And they thought I was stealing it and they bought me out. So I lose the whole thing in 2002. And it was the worst day of my life. But what's crazy about that was at the time that that happened, I had already sold, I raised equity and I really only owned about 16%. So when the proceeds came in, it was about $20 million.

Instead of catching up to NetJets, he was ousted from the company he founded, but he ended up using that money to start his next venture, Directional Aviation Capital, which invests in aviation companies. Do you start Directional Capital with 20 million?

Yes, with the money that came in from the Raytheon, from the sale. One of the first deals we found was Mercury Air Centers. And in 2007, we sold it to Macquarie. And that was sold for $625 million. We had about 200 million of debt. So there was about 400 million of proceeds. So that was a big payday. That changed life significantly.

I wanna hear what you did to celebrate the Macquarie deal.

I know exactly what I did. I'm embarrassed to say, you know, they'll tell you that when you have a big liquidity event, that you do nothing for six months just 'cause you're gonna do something stupid. And I did something stupid. So I went down and we took a two week vacation, Mike and I, we and our wives, to Cabo San Lucas and I bought a house. And I still have it. We still go down there and the families kind of spend a lot of time there. But yeah, that was my celebration.

How much did you pay for the house?

Three and a half million.

Okay.

Yeah.

And you had made hundreds of millions of dollars.

Like, 80 ish. But Mike and I are partners too, so that wasn't all mine, right?

And you spent 3 million on the house. I mean, not bad.

I know you're not supposed to do that.

You're not. Soon after, Kenn clawed his way back to Flight Options. This time he bought Raytheon out. But the company was struggling at this point, and his effort to turn things around would end up changing his plan entirely.

The first thing was to figure out what the plane situation was. So the right plane for us at the time was made by Bombardier, but Bombardier had a competing company called Flexjet. I visit Bombardier and he said, would you let me buy these Challenger 300s, even though it would be competing with a company you own? And they said, all right, we'll sell you the planes, but you have to buy Flexjet too. And so in 2014, that's how I come to buy Flexjet. They kind of made me buy it. I say made me, it was transformational, right? Because they had a big corporate base, they had a outstanding reputation. It's one of the reasons why we collapsed the Flight Options name and came up under Flexjet.

When did you personally hit a billion dollars net worth.

In 2021, when the business was probably doing maybe 170 or $180 million of EBITDA. But we also had these very expensive subordinated debt. You know, we had to borrow money at 15, 16% to be able to buy the flex ship property. So we decided to recapitalize the company in order to pay that debt down. And that recapitalization was done close to a $2 billion valuation with my ownership of the company, put me close to a billion, maybe not quite, maybe 800 million or so at the time.

How did that feel? I don't think you even recognize it.

I don't believe that.

But I think there's two parts of your net worth.

Yeah.

And I think, you know, because sometimes we just wanna focus on the headline number. You really have two net worth, someone like me. Like I have money that's not related to Flexjet. It's the homes you have, it's the cash you have, it's your investments. And then you have the part of the net worth that you never wanna liquidate, 'cause you want to keep growing Flexjet. I think the companies just halfway through its growth cycle. So there'd be no reason to wanna liquidate that. And that goes up and down and it varies, right? Depending upon a good month, a bad month.

I think your values stay the same, but I think the things that you can do and the generosity that you can have to your alma mater or your children or your colleagues, right? Like money does change things.

It does. If you wanna talk about where it's really changed, right? It's the fact that, so my children are older, so my youngest is 24. And so they're all at the age where, we've chosen as a family, not to disguise and not to hide from our wealth. And so we have family meetings every quarter and we're passing on wealth at this point in time. I'm not waiting till I die. I wanna watch my kids enjoy their wealth.

Wow.

And so we're passing on wealth to them now and we're helping them manage through it. And we're helping them navigate. We have a family limited partnership that any of the kids can borrow from to start businesses. And that's probably, if you say the where does the net worth become the focus, it's at those meetings, when we sit there and we talk about what's that you can get your hands on net worth and what are we preserving here and how are we using it? And exactly where are we giving money to? Which I've made them do since they were young.

I wanna hear just a little bit more about these family meetings.

Okay.

How often do they happen? Do you have an agenda?

We have 'em quarterly. Every year, once a year at the big meeting, I walk through the estate plan. What's gonna happen, like where does the money go? How does it get there? I start the meeting by showing my net worth. Then I show them where the assets are, what companies we own, what the liquid money is, who has the liquid money, how do you get to it if I'm not here, who's the guys you call? Like where does the money go? How do you get your share, how do you get your share? And then after I do that, I have all of them expose their net worth and that they tell their siblings what they invested in, what they're spending their money on. And then typically after that, we pass on some wealth at those meetings. Very important that they're not treated equally because life doesn't work that way. One's 12 years older than the other one. So one had 12 years of appreciation over the younger one. That doesn't mean we don't love you, it's just mean life is not gonna be equal. So don't like stand here like the three of you are equal. It's a lot of money for all of you. So I wanna make sure none of them get off about the fact that who has more than the other. So we go right down where it all falls, how the taxes hit each one and why things go there. I want them to understand it. Otherwise, when we're gone, when I'm gone, they're gonna fight. A lot of my peer group does not do that. They do not, like, they will not share family net worth. They feel like it could spoil their kids. If their kids knew how much money they were gonna get, they might live their life differently. I've just chosen to think about it. If I didn't raise the kids right, I'm not gonna correct them by not telling 'em what their net worth is.

So you wanna talk to your kids about money regularly.

It's very important. It's more important than sex. But yeah, we talk about sex all the time and we never talk about money in our family. It's kind of bizarre.