Name: Kenn Ricci Tried to Take His Company Public—But Walked. It Cost Him $32 Million.
Uploaded: 2026-01-13T20:00:00Z
Duration: 7 min 54 s
Description: Getting laid off, starting a company, going viral — are these moments driven by luck or by skill? Billionaire Kenn Ricci, chairman of Flexjet, has experienced both highs and lows throughout his career. In the first episode of The WSJ Money Interview, Gunjan Banerji puts Ricci’s business instincts to the test.

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Getting laid off, starting a company, going viral — are these moments driven by luck or by skill? Billionaire Kenn Ricci, chairman of Flexjet, has experienced both highs and lows throughout his career. In the first episode of The WSJ Money Interview, Gunjan Banerji puts Ricci’s business instincts to the test. Photo: Brian Wengrofsky

https://m.wsj.net/video/20260113/aaf2aa97-44c4-42be-b6cd-1514a8434175/2/hls/manifest-hd-wifi.m3u8

Getting laid off, starting a company, going viral — are these moments driven by luck or by skill? Billionaire Kenn Ricci, chairman of Flexjet, has experienced both highs and lows throughout his career. In the first episode of The WSJ Money Interview, Gunjan Banerji puts Ricci’s business instincts to the test.

Kenn Ricci Tried to Take His Company Public—But Walked. It Cost Him $32 Million.

Getting laid off. Oh.

Is it more driven by luck or skill?

Kenn: I can't go in the middle.

So you're trying to be strategic here?

I actually changed my thought process. I'm gonna go more on.

How much of success is just pure luck? We've got the ultimate guest for this topic. Kenn Ricci is the founder of a private jet empire, and he's here to play a little game of luck versus skill. Kenn, you are going to pick a card from here and then place a dart on where you think it ranks based on whether it's more driven by luck or skill. There's one rule, nothing can be 50/50.

It really can't be 50/50?

It can't be 50/50.

Okay. So selling a company. That is, I'm gonna go luck.

Really?

Mm-hm. Yes.

Tell me why.

You cannot like put a business plan together and say, "We're gonna develop this for five years, and then in year five we know that LVMH is gonna buy it because we've slotted it for here." You're susceptible to some luck. What's the environment doing at the time? Did LVMH make a lot of money so they still have a good cash account to buy you out? So you could have great skill, but that doesn't mean you're gonna be able to sell your company.

Sounds like that's also applicable to going public.

Absolutely, you hear the people all the time say the markets are open, the markets aren't open.

You tried to take Flexjet public in 2022, right, by merging with a special purpose acquisition company? And then you ended up terminating the deal.

Yeah.

Why'd you walk away?

Because I made a mistake. I had a partner in the business at the time, still a partner, and he asked me after eight years, "Do you have any thoughts about how to get liquidity?" And at the time, I don't wanna sell the company. And I'm the majority shareholder. People just don't buy my minority shares in the private market. So I did it out of trying to help Todd find a market to be able to find some liquidity in his stock. What I found in the next three months was that our customers hated it. They thought our service would go down. They thought we'd lose our culture. And I love to talk to our pilots, and they always ask me, "Mr, Ricci, what are we buying next? What airplanes are we having?" And I realized every time I talked to an employee, they have to go file a 10K and like tell the SEC what I said. So it became an environment I just couldn't operate in, and that's why I pulled it.

Did you mistime the market? Because in 2022, the stocks had started falling.

I was naive about what being public meant to me and to the culture of the company. And I was being genuine trying to help my friend, but I didn't realize the horrible, in my eyes, the horrible impact it'd have to the company.

Was it tough to back away?

It cost $32 million. Getting laid off. Oh. I can't go in the middle. Let's go.

So you're trying to be strategic here.

I am gonna be strategic. I've actually changed my thought process. I'm gonna go more on skill because first of all, if you're skilled as an employee, then the company's gonna do better anyhow and you might not get to the point where layoffs are needed. And I think if you're with the right company, maybe you can always avoid this. But if it does happen, a good company is gonna lay you off based on your skills, right? So it's not gonna be luck.

But doesn't what you were saying about macroeconomic trends, also, like a lot of people were laid off during the global financial crisis who, sure, they were quite skilled, right?

Yeah, but let's go back to then who got laid off? Somebody made a decision on what skill set they left behind, right? With the exception of the ones that just totally went out of business. If you have a high skill set within the company, then the likelihood even in a downturn is gonna be less. And also then you're likelihood of survival is gonna be better based on your skills, so be skillful.

Let's do the next one.

Marrying the right person. Mm-hm.

Gunjan: I like this one.

Kenn: I'm gonna go very high luck.

Really?

What you wanted at 20, what you wanted at 30, what I wanted at 40, it just changes. It's just the way life is, right? And it takes a lot of luck to find a person that can follow those changes, that their changes are in concert with you, and that over the course of time it kind of works out.

Can marrying the right person help you get rich?

It's one of the most important things to getting rich, right? Who's behind you? The right person certainly helps you, right? Because just think of the ease it makes within your life. Just think of the support, the things you don't have to worry about, the things that are taken care of.

I've noticed when you share pictures of you at chairman's events for Flexjet, your wife is often by your side. Was there something that she handled that she was better suited to handle versus you?

Oh, I mean she's the artist. She has the artistic brain and she thinks emotionally, right, where I think analytically. So I really respect her opinion of, you know? It's been 16,797 days we've been together, so I got a lot of time to play off that.

The next one.

Going viral. This.

Gunjan: Oh wow, okay.

I mean, you've seen people when they try to create the viral moment, right, and it's almost invented. So that leads me to say you can be very skilled. And who knows why did one thing go viral and the other thing doesn't? This seems to be chance. Getting a promotion at work. Okay, so I think one of the hardest things to do is properly evaluate and to put people in the right position to set them up for what they can do correctly and what they're good at. So to me, this comes about finding where your skills interact with needs.

What about meeting the right person, right, who helps you get promoted?

I'm gonna stay with skill. Let's do the contra argument. Someone's not gonna want you to get ahead, and they'll purposely hold you down. But I think skill will overcome that. And if you're not being recognized for your skill at that company, then you'll find another company. You'll move on.

The final one.

Final one. Starting a successful business. I'm gonna go one step up on the luck chart. You can identify a product that you really think there's a need for and do that, but there takes a little bit of of luck in finding the right opportunity. It's a lot of skill, but you do need a luck break.

What was your lucky break?

My luckiest break was a deer on the runway in Charleston, West Virginia. The captain froze, and I'm in the copilot seat. And I dunno if you know anything about spotting deer. I knew right away that the lights had blinded the deer, so I reached up where the landing lights were and I flipped them both off, and the deer ran away, and we went down the runway. Well, the guy I was flying that day was the CEO of a very prestigious investment banking firm called Prescott, Ball & Turben. I didn't know it, but he saw me do that. And he pulled me aside later, and he said, "What are you doing flying in the copilot seat?" And I told him that I was starting to build a business around flying aircraft. He said, "How can I help you?" And I said, Well, you could recommend me to other people in town." And he recommended me to Parker Hannifin, which is a big company. So flipping those landing lights off, he paid attention to me and helped me grow the business. That's a lucky moment.

I mean, I'm super interested that you do tend to skew in the luck direction here. You've clearly worked really hard and are very skillful, and yet you attribute all these things more to luck.

But also what I tell you is, you know, the harder I work, the luckier I am. And so I think maybe I'm defining luck as identifying opportunity or having opportunity come to you. Putting yourself in a position to be benefit from being lucky does take some skill. So I would just say, I think you put yourself in a position to benefit from luck. These are harder than I thought. I'm gonna do this at our company.

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