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From a $27,500 Charter Company to a $4 Billion Private Jet Giant | Kenn Ricci, Flexjet

Tell your children about your wealth while you are alive to guide them through it. Start with small, concrete conversations early. Young children can begin by deciding which causes to donate to. As they get older, walk them through a spreadsheet each year showing where the assets are, how they tran

1h 11m

Summary published by , updated .

David Senra

Key Takeaway

Tell your children about your wealth while you are alive to guide them through it.

Start with small, concrete conversations early. Young children can begin by deciding which causes to donate to. As they get older, walk them through a spreadsheet each year showing where the assets are, how they transfer, and who controls what.

Ken Rickett argues that keeping children in the dark signals distrust, and that handing over wealth after you die means you cannot help when they make mistakes. Being present for those decisions is the entire point.

Episode Overview

How should wealthy parents think about passing money to their children, and what does a business built on passion actually look like from the inside?

Ken Rickett built Flexjet, one of the largest private aviation companies in the world, starting from a $27,500 acquisition of a small charter operation in Ohio. The conversation covers his family approach to wealth, his accidental path through aviation, and the question of purpose that followed him throughout.

  • Wealth and family: Rickett shares how he structured early giving, annual financial meetings, and a family limited partnership to build trust across generations.
  • Building the business: From flying celebrity tours to fractional ownership, the story runs through furloughs, financing crises, a forced buyout, and an eventual repurchase of his own company.
  • Purpose and service: A recurring thread is Rickett's discomfort with accumulation for its own sake, and the conversations with mentors that helped him make sense of it.

Fractional ownership means buying a share of a private aircraft rather than owning or chartering one outright.

Main Insights

1. Share wealth with your children while you can still guide them

Rickett argues that transferring wealth only at death, or through trusts that unlock at set ages, is a way of maintaining control rather than building trust. By the time the money arrives, you cannot help your children navigate what to do with it.

His approach: gift shares of a family limited partnership when the children are young, hold annual meetings that cover the full picture of where the money is and how it moves, and be present for both the good and the bad decisions.

The concern that early wealth makes children lazy, he says, is really a confession that you did not trust your own parenting. If that one thing undoes everything, the parenting was the problem.

Charlie Munger put it simply when asked the same question: give them the money, because they will resent you if you do not, and what is the point of building a relationship across a lifetime only to have your children angry with you at the end?

2. Staying inside what you know compounds over time

Rickett describes his investment portfolio as "cash and airplanes." Every business he bought, sold, or backed was in aviation. That focus meant he could walk into a deal and immediately understand the operating metrics, the relationships, and where the risks were buried.

When he went looking for capital, the pitch was simple: I can tell you where the bodies are in this industry. You do not have to explain the business to me.

The pattern echoes what Buffett and Munger call the circle of competence. Rickett did not choose this deliberately at first. He chose aviation because he loved flying. The depth accumulated from passion, and the financial returns followed from the depth.

3. A business built on passion looks different from the inside after a forced exit

When Raytheon bought Rickett out of Flight Options in 2002, he describes it as the worst day of his life. Not because of the money, but because the purpose disappeared.

He moved cities to stop being asked what happened. He had no vision. He found himself hoping the company would not succeed without him, while also not wanting it to fail, because then his whole idea would have meant nothing.

He eventually bought the company back in the middle of the 2008 financial crisis, pledging his home and signing a personal guarantee, because he wanted it back regardless of the condition it was in.

What he lost in 2002 was not income. It was the work itself. That distinction is worth sitting with if you are building something you care about.

4. Good customer service lives in who gets to make the call

Rickett's explanation of customer service at Flexjet is structural. The person who answers the phone when something goes wrong has full authority to comp a trip or issue a refund. No supervisor approval, no escalation process.

His reasoning has two parts:

  • It signals trust to the employee, which carries through to how they treat the customer.
  • It means the problem gets solved at the point of contact, by the person who actually understands what happened.

Customer service is about what you do when things go to hell, not when they go well. A $80,000-a-year employee authorized to comp a $300,000 trip is a policy decision, not a one-off exception.

5. Prepare children to manage wealth together, not just individually

Rickett's three adult children, after years of annual financial meetings, arrived at two agreements on their own. First, they decided to exclude spouses from the meetings, because those relationships had not gone through the same decade-plus of financial transparency. Second, they built a structure for shared investment opportunities.

The rule they created: if one sibling makes an investment, they must offer 20% stakes to each of the other two, though participation is optional. The goal is to remove the jealousy that builds when one sibling does noticeably better than the others.

This was their idea, not their father's. Years of open conversation about money produced children who thought carefully about how to protect the relationships across the next generation.

Frameworks or Models

Family limited partnership for generational wealth transfer

A legal structure that allows a parent to gift ownership shares to children early, before assets appreciate significantly, while retaining operational control as the general partner.

Rickett's approach:

  1. Establish the partnership before children are born, so shares can be gifted at birth when values are low.
  2. As general partner, retain flexibility to make distributions on your own timeline.
  3. Hold annual meetings to walk all family members through the full picture: what is held, how it transfers, who controls what.
  4. Start conversations with giving rather than investing, so children build a relationship with money as a tool before they encounter it as an inheritance.

The structure separates legal control from transparency. Rickett kept control as general partner while treating the children as informed participants from an early age.

Notable Quotes

"If you're going to spoil, this is going to spoil your kids, then you really weren't that good of a parent. If that was the one thing that did it, they couldn't handle this."

Ken Rickett

"Money comes naturally as a result of service."

Ken Rickett (quoting Henry Ford)

"To have a life of significance, you only have to do three things. Be true to your God, be as good as your parents and champion the causes of underdogs."

Ken Rickett (quoting Father Ted Hesburgh)

"Customer service is about what you do when things go to hell. It's not about what you do when things are going well."

Ken Rickett

Action Items

Suggested exercises inspired by the conversation.

  • 1
    Start a family financial meeting

    Rickett began these meetings when his children were young, starting with giving rather than investing.

    1. Pick a recurring time, once a year at minimum.
    2. Begin with something concrete and low-stakes, such as which causes the family wants to donate to and why.
    3. As children get older, add a simple spreadsheet showing assets, how they are held, and what the transfer plan looks like.
    4. Make it a two-way conversation, not a lecture.

    The goal is familiarity and trust, not a formal financial education.

  • 2
    Audit who has authority to fix a problem in your organization

    Rickett's customer service model gives front-line employees full authority to resolve issues without escalation.

    • Identify the most common type of problem your customers report.
    • Find out how many steps it currently takes to resolve it.
    • Ask whether the person closest to the customer can be given the authority to handle it directly.

    Notice whether your current process signals trust or control, and whether that matches what you intend.

  • 3
    Map your circle of competence before the next investment

    Before committing capital or time to a new venture, write down what you already know deeply.

    1. List the industries or domains where you have spent at least five years building knowledge.
    2. For each one, note what you understand that an outsider would have to spend years learning.
    3. Compare any new opportunity against this list.

    Rickett's edge in every deal he did came from being able to skip the explanation phase and go straight to the risk.

  • 4
    Test whether a major decision is driven by fear or by actual values

    Rickett describes buying Flight Options back during the 2008 financial crisis, pledging his home, because he wanted the work regardless of the risk. That clarity came from knowing what he actually cared about.

    • Write down a significant decision you are weighing.
    • List the reasons you are leaning toward the safer option.
    • For each reason, ask whether it is protecting something you value or mainly protecting you from discomfort.

    The distinction often becomes clear once it is written out.

Full Transcript

Read or copy the complete episode transcript.

I just interrupt you before we start recording. I want to, well, you brought up your kid about the addiction of flying privately and, and, and I, um, I have three children and they're six years apart. So there's 12 years from the oldest to the youngest. And when I was building the business, and of course, remember I started the business, I was flying too. So I would fly and run the business. When you raise a child, you start on Braille and you start to figure out like, you know, what's the relationship going to be like that? I spend enough time that I miss little league games. But I decided I was going to give them a love of travel. So I had them all skip eighth grade and we traveled during their eighth grade year. And we didn't leave for, for the whole year. We'd go on six, three week trips. And during that time I would homeschool them and I'd make them build a curriculum around where they wanted to go. And we didn't take them to Paris and London. I mean, we took them to places around curriculum who wanted World War II, who wanted to go to India, who was fascinated with Asia. So we built these curriculums around, actually the two places I made them all go was Auschwitz, and North Korea. So I'm probably the only person that's been three times to North Korea. But you know, life changed. So starting in 2005 to 2017, think of the 12 years between. The youngest one who, when he did his trip in 2017, I realized had never been on an airline. And I... An airline? You mean a private jet? No, no, no. He'd never been on an airliner because life for me had changed. Oh, he'd never been... He'd never flown commercial. He'd never flown commercial. And so I decided it's a bad way to raise a child. So I decided his name's Austin. So I said to Austin, we're going to go commercial. We were going to Tokyo. And we go to the airport. Never done this before. We wait in line, check our baggage, wait for our seat to be called, sit down, don't take your shoes off. But all the things you do, right, security and so on, we sit down and finally we're getting ready to take off. And I look over at Austin. I go, Austin, what do you think? He goes, hey, dad, there's people on this plane I don't know. So what he didn't get was like the commercial, the public part of commercial transportation. It's funny that you... We were talking about this right before we started recording. I was like, we got to hit play because I'm so interested in... Like you started talking about, you know, a lot of people that build successful companies like you do, there's this huge doubt in their mind. Like, you know, I'm hugely driven. I have a goal in my life, but like there has to be things that are sacrificed. So I go, obviously time with the children is one thing that people do. But one of the things you didn't even know I was going to ask you first was I heard you talk about something that's interesting to me. That is, you decided to share your wealth with your kids, not when you die, not when they're older, but right now. You have a very interesting perspective on this. Can you explain what you're doing? I came to believe that we have the wrong perspective on raising children. We seem to think it's about the time we spend with them. So therefore we kind of raise this helicopter mentality, right? We go everywhere with the kids. We don't let them out of our sight anymore. When I was growing up, I left at nine in the morning on my bike and I just had to be home for dinner and mom didn't chase me around Cleveland, Ohio, right? Those days are gone. We tend to think that we put time into them. That's the essential. When what we really need to put with them is we need to show them that we trust them and they can trust us. Think about wealth transfer. If you don't tell your kids about their financial arrangement, you're saying you don't trust them. I told my wife when the kids were young, I go, we're thought as parents to talk more about sex than we are about money. The reality is money will get you in a lot more trouble than sex will. I had three observations about wealth transfer. One is that there's a whole cottage industry around trust and the management of generational wealth transfer and there's big money in it. The system wants you to think you have to control wealth because that brings in the trustees, that brings in the law firms and the banking firms and all those necessary professionals to kind of skim away your wealth. Second of all, the Chinese have a saying, the son of a lion is a lamb. I think people that create a lot of wealth, particularly if it's entrepreneurial wealth, tend to have, they're lions and lions control things. Why not buy into the system where you control your children? This is why these trusts are set up. At 25 they get this, at 35 they get that, at 45 they get this. This is kind of a way to control from the grave or for the patriarch or matriarch or the wealth to still be influential even when they're not around because they don't want to be in charge. They want to be important. They don't want to lose their relevancy. And then finally, there's the most bizarre one to me is if we tell our kids, if we give our kids wealth and we tell them about wealth and they know about this, they'll become lazy. Well, man, does that say you must have been an awful parent. That was the one thing that flips the switch. You couldn't parent through that. So I decided, A, number one, most importantly, I love my children and I love watching them be happy. I want to watch them spend their money. I want to watch them be wealthy. But most importantly, I want to help them. I know a little bit about wealth. I knew a little bit about, now I'm accidentally wealthy. I didn't get here with some strategic, you know, some monetary plan, financial plan. Hold on, we're going to dive deeper on that. But give me some background. Did you grow up middle class, poor? Like, what was your childhood like? Oh, my father was a grade 12, worked for the U.S. government, he's actually a spy. He had a fascinating background. He came out of World War II, worked in the OSS, worked in naval intelligence, and then had a, in the 60s, early 60s, Bobby Kennedy set up the OCD, the Organized Crime Drive through the Treasury Department. My dad was a part of that group that investigated domestic, mostly mafia, mostly organized crime in that era. His undercover name was Richard Dill. He was investigating a lot of cases, Italian, he was Italian, they changed his name to Dill. Think of that, that's the government at work. I remember one time he, by the way, he only in 17 years of undercover work, he only worked on three cases. So, shows you the time it takes, right, to be an, to work. So his undercover name was Dick Dill. Richard Dill. Hey, Dick Dill. Richard's always short of names. Yeah, yeah. He was investigating the police chief of Lincoln, Nebraska. And for both ties to the organized crime. I'm seven years old at the time. He can't, and he can't tell you. I don't know much about it, but I knew that, I knew that we had to go live in Nebraska for two months, because he was there undercover as a family. This was the greatest time of my life. We stayed at a Holiday Inn, had a pool, I'd never been any place where they had like a pool outside. So that, that hits on, it's like middle class, somewhere around there, didn't have a pool. The reason I wanted to start on this, and I'm going to still pull on this thread if you don't mind, is because I have this other podcast called Founders, I read biographies of history's greatest entrepreneurs. People struggle with this all the time. It's in these books for going back 200 years. They're like, I was, essentially the problem is, I was the son of a poor man. My kids are the son of a rich man. What do I do here? And so I had the, the luck of a lifetime to be able to go and have dinner at Charlie Munger's house right before he died, probably six months before he died. And one of the questions I asked him was, because me and him had run, he read, you know, hundreds of biographies. I was doing the same. I was, the, the, my, my craft and the main, before I started this show, like all I was focused on. And I was just like, what's the answer to that? Like, you read the same books I do, what, what's your answer? You know, he grew up, he wasn't poor, but they were in a home all along, it was like a normal life. And he goes, you give them the money, because Munger's just no bullshit, straight to everything. And I go, why? He goes, because what, he goes, they'll hate you if you don't. And he goes, and what's the point of building a relationship and making all this money? And then at the end of your life, your kids hate you. And that was his very simple way of looking at this. Fantastic. Fantastic insight. Right. Like I said, I want to watch them enjoy their wealth. He did say one funny thing though, because somebody, I think I may have asked him a follow up. So either me or somebody else follow up and I go, yeah, but won't that make them a little less ambitious? He goes, yes. And in his case, I think he gave, he gave a couple hundred million to I think nine kids or something like that. And he's like, yeah. But they're not $250 million and they're not as ambitious. Like so what? They're different. Every kid is different. In fact, one of the things we have these family meetings once a year where we talk about wealth. And one of the things I start out with each project, because when I look at why families rip apart over wealth, right, it's really in two areas. One of them is that they feel somehow they're entitled to be equal, but they're not. I have a child that started inheriting wealth 12 years before the youngest one. You don't think his estate, you don't think what he has appreciated at different rates than the youngest one. So I start every meeting by going, look, guys, you're not equal. It doesn't mean I don't love you. Doesn't mean it's just, it's just how things are. And the sooner you get over that fact, the happier you'll be. It's just what it wasn't set out that way. So are you already given all the wealth you're going to give to them or that you keep, how do you like, how do you, well, well yes, pretty much so because we gifted shares of a family limited partnership when they were very young. Did you get this idea from Sam Walton? Uh, no. You know, that's how Sam Walton avoided a lot of, he, he didn't do it to avoid estate tax. He would wind up, he's like, well, if you want to avoid estate tax, you give your kids the asset before it appreciates. It's so logical. The crazy thing is he did this, his father-in-law gave him the idea. I've read every single book on Sam Walton and his father-in-law gave him the idea. They did this when the value of Sam Walton's company was like, I think the shares that he gave to his four kids were $5,000 each. Ditto. Okay. I started the family limited partnership in 1990, I had my first child in 1995. So I have the vision of what it's going to do five years before it happens, right? And as soon as I could, as soon as I could, I gifted shares when they were born, I gifted, it's a family limited partnership. So the general partner, which is me still can, you know, I have all the flexibility in the world to make distributions. It's a phenomenal vehicle. So Walton had it right. It's a great vehicle. So they're not created equal. I want to watch them happy. I want to watch them use them, but, but also I want to guide them. I want to be here alive when they're making stupid decisions with their money or making good decisions with their money. I've made stupid and I've made bad decisions with money too. But so, so why can't I be the one to guide him? Well, otherwise, assuming they, they still love me when I'm dead, they tend to love you more when you're dead. But in any case, assuming they still love me, well, I'm going to go, well, what would dad have done? Well, isn't it better to like be here alive when they ask you, what should I do, dad? You know, that's the foundation of it. So I think sometimes we want to rule from the grave. You have this trust environment that's there. And then if you're going to spoil, this is going to spoil your kids, then you really weren't that good of a parent. If that was the one thing that did it, they couldn't handle this. Or maybe the alternative is it's all the more reason to give it to them when they're alive so you can guide them through it. Right. As opposed to when they're dead and you can't do anything when you're dead and you can't do anything about it. I want to tell you about the presenting sponsor of this podcast, ramp. I have been reading a lot about SpaceX lately. SpaceX is one of the most valuable businesses in the world. And one of the main themes in the history of SpaceX is constantly attacking and questioning your cost. Ramp helps many of the most innovative businesses in the world do exactly that. The median company running on ramp cuts their expenses by 5%. And one thing SpaceX has demonstrated is that a religious dedication to controlling costs can help actually increase revenue because you can pursue opportunities you couldn't otherwise. And we see that in the ramp data too. The median company running on ramp also grows their revenue by 16%. 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AppLovin ads are full screen videos that are watched for an average of 35 seconds. That is retention that blows other ad platforms out of the water. And you can launch on AppLovin in minutes. You set the goal and AppLovin achieves it. No complex setup, no expertise needed. And AppLovin scales quickly. They can put your ads in front of over a billion potential customers. Other businesses have seen immediate results scale to hundreds of thousands of dollars of spend per day and increase their revenue by millions. So you want to get started quickly before all of your competitors are on AppLovin. And you can do that by going to AppLovin.com. That's AppLovin.com. Have you seen any downsides to this decision? Not one. Not one. In fact, I've seen many things I didn't really, I didn't think would happen. So for instance, I asked them, now remember, this is going back. When they're young, I started talking to them about money. Now at five years old, six years old, we're not talking about tax effective or compound in interest. But what I taught them early on was giving. So our early family meetings were all about who should we give money to and why. My daughter loved animals. My son loved Catholicism. And my youngest son, when I remember the first time we were giving, he was maybe six years old, he always wanted to give it to Disney. And I was like, well, Austin, Disney's not really a non-for-profit. They have their own methodology. So I taught them first to give. And then before we started really diving into the estate, and I really went into that when the youngest one was around 16, where we really started going through, like every year we go through a spreadsheet. Where's the money? How does it transfer? Who has control of it? Where's the bank? Like all the stuff you need to know, everything. But before we did that, we did a personality test and everybody reported on their personality because kids are different. Who thinks left brain? Who thinks right brain? So I wanted the kids to understand how they could get along. So I started with that. So then we started talking about money, how it transfers, like what we would do with it. Two surprising things. Number one is that it creates this trust. And I have this amazingly trusting group. Now the kids in the group of five, my wife and I and the three children, they report, they show us their estate and what they spent money on. And we share this. How old are the kids now? They're 37. 20, 31. They're 37. 20. One and 25. Okay. Yeah, okay. So it's been going on for a while. But the other thing, like I mentioned, I'm accidentally wealthy. You have to realize that even when we were talking about this, we weren't talking about it at the volume we're talking about today. I mean, my personal net worth has accelerated in the last six years, along with FlexJet, which is the asset I own and, you know, one of the largest assets I own and protect. One of? It's gotta be the largest asset you own. Well, it's the largest one, yes, but. What else you got that I don't know about? Well, I mean, I always say I'm an inch wide and a mile deep. I've made a lot of investments only in aviation. I probably know more about the area of aviation. I've invested in, I own SimCom, which I sold to CAE. I owned, I owned what is today Atlantic Aviation. Hold on, let's, so let's, this is exactly, so I want to start talking about the business, because I think I understand the, what you did with your kids and why you did it. And I think, again, anybody who's wealthy has to think through these things. I think discussing them openly is a service to other people. Oh, I'm sorry, let me finish what I learned. Okay, so number one, this amazing trust that they got amongst themselves, right? They started investigating and reading about biographies and families that blew it. And they came to realize that the third transfer of wealth, the third generation's the tough one. And so they've started to talk about- Sheer sleeves to sheer sleeves in three generations. This is something very durable through human history. So they've come together to talk about the next passing of wealth and generational, and two things that they've come up in the last year. One is they decided not to include spouses in these meetings. They decided that each one of them, two of them have spouses, one doesn't. They decided in these meetings that each one of them will decide how to share financial information in their own family. That this isn't a group share. This is us five, and we've been doing this for 10 years, 12 years. And it's not something, we're not gonna toss people into the middle of it, because we don't know their personalities. We didn't have 10, 12 years of grooming to get them to this point. So that was number one. Number two was when they look at generational wealth transfer and why families come apart. One of the things that happens, other than they all feel like they weren't treated equal, they're mad at the patriarch for not treating them all equal, which we've gotten over. But the other thing that happens is one of them does really well, takes the money and makes a great investment. And the other ones do less. And then there becomes a little jealousy amongst them. So they decided, they came to the idea that any investments they all make, they're gonna share. And the person who has the investment. The three kids. The three kids. The person that has the investment can put 60% of it in, but has to offer, but not required, 20% to each of the other siblings. And they can participate or not, thereby alleviating the opportunity for them to be jealous. Look, I gave you the opportunity to come in, you came in and you didn't, or we share the upside to get. That was their idea, not my idea. That's really interesting. So let's go to the source of the wealth. You were a pilot, okay. Take me back to like, well first of all, how old were you when you learned how to fly planes? You talked about my upbringing with my parents a little bit. My dad was a government employee and I went to a Jesuit high school, St. Ignatius, and they sent, at the time in the 70s, they sent 30 people to Notre Dame. They moved them right from there to Notre Dame and I loved it. I wanted to go there. And I was, I got admitted and then I'm going up for a visit. And I grew up in a, you know, houses have two by fours, ours has one by twos. So I could hear my parents, I'm an only child, and I could hear my parents talking the night before I'm going to Notre Dame and they say, you have to tell him we shouldn't let him go because what if he goes up there and he likes it and then he wants to go and we tell him we can't afford to send him. My mom was saying I wouldn't let him go and my dad would go, let him go, maybe he doesn't like it. And then he comes back and says I don't want to go anyhow and then we don't have to have this subject. But I knew going up for that class visit that didn't matter how much I liked it, I knew what was coming when I came home and said whether I wanted to go or not. So I was inclined not to go and put my parents in a bad position. When I get there, I ask them on campus, is there a, is there financial aid available? Well, you missed the deadline, this is March. But the Vietnam War, this is 1974, the Vietnam War was still very ripe, very raw and people did not like the military. And so they said, if you're willing to go into ROTC, they're always short of the candidates, they never fulfill in their quota. So for some reason, don't ask me why, I decided I wanted to be a Navy pilot. Maybe I like the double breasted suits, whatever. So I go down to the ROTC building and there's no cell phones and I'm looking through the glass window, I'm trying to read upside down on the phone what number to call on Monday morning to tell them they had a new naval aviator. Why'd you pick aviation? You'd never flown a plane or anything? No, I had to go in the military. I know I had to go ROTC, I figured if I got to go into the military, flying looks like a lot of fun there. I'm copying the number down and somebody taps me on the shoulder and they said, can I help you? And I said, yes sir, I'm an incoming freshman at Notre Dame and I would like to join the Navy because I want to fly. And he said, you've been admitted to Notre Dame? I said yes. He goes, I'm shocked because they usually admit smarter people than that. He said, the Navy has ships and the Air Force has planes. I'm Colonel Muller, I'm head of the Air Force Detachment and I'm enrolled in the Air Force. And I never heard, I never knew how my parents reacted but I came home. And then they'll pay for school. Yeah, yeah. I don't know that I've ever told this story. It's the first time I learned how to defraud the government. It was, I'm a freshman at Notre Dame, I'm enrolled, I've got my hat, I've got my uniform and the sergeant who administered that said, now I know you're a plea here but here's how, you get $100 a month stipend for general expenses. He goes, but there's other income. He goes, here's what you do. You go to the bookstore, you buy all brand new books, you bring me the receipt, I'll reimburse you for the new books. You take them back to the bookstore and then you buy the used books. So like my first interaction with the military is I was taught like how to take advantage of the U.S. government. Did you take time off from Notre Dame to learn how to fly? No, no, no. You learn it concurrent. You, one day a week and this was the tough one. One day a week, you have to stay in uniform. And believe me, at that time, it posed, you know, that Vietnam War era, that was not an easy task because people did not like the military at all at that time. So, you know, you have all these courses around the Air Force. In the summer, you go to whatever your summer program was, your summer school and so on. And then, so that's where I learned to fly. So what kind of planes do you fly? The first thing you fly? Oh, you know, the Cessna 152, Cessna 172. They're not putting you in like the F-16s. No, that comes after grade. No. No, in fact, you know, when you graduate, what happens, then you go to general flight training, which is done like in T, that time was done in T-37s and T-38s. And then you get assigned, you know, it's a year and a half before you get control of a jet in the Air Force. There's the primary training, then there's the training you go into. Okay. So you mentioned, hey, I'm an inch wide, but I'm a mile deep. All my businesses focus on the, this, we've mentioned Buffett and Munger. I don't know if we said it on the show, if we were talking before, but like we both mentioned Buffett and Munger a bunch of times. And their whole thing is like, know your circle of competence and just stay inside that circle. So that sounds like what you did. Your first- I always say, my portfolio of investments is unbelievably diversified. It's cash and airplanes. That's my diversification strategy. So what's the first business you do in aviation? So first of all, I don't think of myself as a businessman. In fact, I'll often say there's two people that are very successful in business. One is a person that just gets business. They could run a yogurt store. They can run a steel manufacturing plant. They just get business. They understand how they're connected. They see market strategy and business is just very clear to them. And the other ones that are just passionate about what they do. You're passionate about your podcast. You're successful in business because this is what you love to do. I'm successful because I love to fly and I learned everything airplane. Right, that's what put me here. But I didn't, I never had a goal to become wealthy or to build a business. So- That's the accidental wealthy part you're talking about. Sure, of course. In many ways, right? Accidentally that I even formed a business. Accidentally that when I go into private aviation, there's only 5,000 jets in the world. And today there's 35,000 jets. So part of my luck- Wait, wait, wait. Say that part again. Yeah. When you started- So what is this? 1985, figure about- There's only 5,000 jets? 5,000 jets in the world. And today there's 35,000 private jets in the world. So part of my luck was just to be when this industry grew up. I entered an industry because I could have been an airline pilot. I could have gone into, I could have stayed in the military, but I was attracted to private aviation. It was more free to me. It was more spontaneous. It was more interesting. The people you would meet, that there's no cockpit door. I could have conversations with passengers and learn from them. So who knew in 1985 that private aviation would be this unbelievable growth industry in the next 40 years, right? Didn't know that. So that's part of it. But what I'm really doing is flying. I leave the military. I become a cargo pilot, flying air freight. Then I go to Northwest Orient. I'm at Northwest Orient a very brief period of time. They have a furlough, so I lose my job. So wait, Northwest Orient doesn't exist anymore? No. It was an airline. It was an airline, yeah. So you're an airline pilot. The airlines were Pan Am, TWA, Northwest. The airlines that flew all around the globe, they were the good airlines. They were the airlines that were the prestigious ones. Okay, so you're in Northwest Orient. You said you got furloughed, which is another name for fired. Yeah, it's a fancy term for I don't have a job. So I came back to Ohio. Ohio, birthplace of the Wright brothers. Yeah, well, that's in Southern Ohio. Yeah, but I think Dayton, right? Yeah, but my father was, he didn't see it as a very stable career. He said, I know a lot of pilots and they're all airport jockeys. They just kind of move from place to place and they end up taking whatever job they can. It's just not a stable industry. So it was at that time that I went to law school. So you love flying and pilots. Your dad's giving you, in hindsight, bad advice. Well, your life is turned out and you're going to do something you don't love. Correct, correct. For prestige or money, what was it? You needed something to fall back on in case this aviation thing doesn't work out. Well, the aviation thing worked out okay, but. Did he live long enough to see it? You know, he died in 1991. So, kind of, kind of. He saw me have a business. He saw me fly. He flew on one of my first Learjets, loved it. Okay, but he never, I mean, you know, he never saw this coming. The only job I can have in law school is a part-time pilot. So I'm a fill-in pilot for a company called J&J Aviation and J&J Aviation was a fraud. I mean, I'm just an employee there, but what they did was, in the early 80s, they had an investment tax credit of 10%. And if you bought an aircraft, you got an immediate 10% credit. So they would sell these Citation jets for $750,000. So they had about a fleet of about six airplanes and then they'd sell these Citation jets to investors on the West Coast, a long way from Cleveland. And they'd get the $75,000 investment tax credit and then they'd pay the $750,000 for the plane. And then the head of J&J was a guy named Jeff Tolk. And every month he would pretend that these aircraft were unleased, but they weren't. The aircraft didn't even exist. He would make up a dummy statement. He would say it flew 40 hours this month. The revenue was $90,000. The expenses were $78,000. Here's your $12,000 check. So he simply put the $1.5 million, the two aircraft, he put the $1.5 million in the bank and kind of dribbled out the interest in a fake statement. Well, finally, after about a year and a half, the owner said, we gotta see our jets. And they were never, they were always in the air. They were never around. But one day they caught him and he flew the coop. So this little company, J&J Aviation, had like three employees, a secretary, a dispatcher. And is this just charter? What's it like? Yeah, okay, it's just charter. It was using these managed airplanes or these phantom airplanes. But there were six of them. There were Navahos and these little tiny piston engine aircraft. And the dispatcher, dispatcher there, Rick Michaels, calls me up. And he says, he said, you know, nobody here wants to do this. And I don't have, I'm not smart enough to do it, but you seem to know a little about aviation. You should buy the company. So I call my dad. And you're how old at the time? 26. And you never thought you were gonna be an entrepreneur? No, in fact, I didn't even buy this company to be an entrepreneur. I bought it so I could still have a job. Like I needed to make sure these airplanes didn't go away so I could keep flying. I mean, that was the whole goal. And Rick said he could do it by himself. So I left, I kept, I knew I had to employ the dispatcher and run, it ended up two of the planes left. So I had four airplanes when I started. And I called my dad and I said, dad, I'm gonna, I wanna buy this company, J&J Aviation. I'm actually gonna name it Corporate Wings. And he goes, oh, he goes, I go, it's $27,500. And he said, well, how are you gonna pay for it? And I said, well, the company has 27,000 in the bank. So I think I can just use their own money to buy them. And he goes, oh, he goes, well, what are you doing for the other $500? I go, why do you think I called you? So that was really how I bought Corporate Wings. And that company's still here today. Explain how you went from Corporate Wings to Flush Jets. Right away, I decided, where's the niche for this Corporate Wings? Like, everybody has a charter plane. Like, but how do I get bigger niches and so on? And I, you know, life is timing. I met someone who worked for Chapman Freeborn. I don't know if you know this company. They move all the rock stars around. So they move the freight. You know, every rock star comes with a stage. And part of that stage can go on the land. Part of it has to go in big aircraft, depending upon, but it's a cargo moving system. And along with it, they had this ancillary business to move the star, to move the celebrity. I'm watching this documentary on The Eagles, the band The Eagles. And they have a bunch of success early on. And one of their favorite things about being in a band and being a rock star is that they have this private plane. Absolutely. It's like a little, like, turboprop plane. Yeah, the big groups went in those turboprops because they needed 15, 18 seats. It's the single performers that went in the Corporate Jets. I flew Elton John, Brian Adams, Bruce Springsteen, Tony Bennett, Barbara Streisand. Those were the ones. Those were my clients. So with Chapman Freeborn, whenever they would get a cargo movement and they needed to move the celebrity, I made a deal with them to do that. And that was how, that was really how- That was your initial niche. But it was really because I wanted to fly. And I've thought it'd be- Oh, you're piloting that? Yeah, of course I am. Of course I am. Sure. And you know what? It was a good gig because you, when you flew those celebrity tours, say a pilot at that time got 7,000 a month. If you flew a three month tour, you would get 20,000 a month. You had no work for that. And it was kind of perfect because I could fly the tour for three months and then have the rest of the time, I'd work on the business or- kind of learn the business and figure it out. So I'm building the business concurrently with doing these celebrities. Then I have these big planes, so I start to go more international. I fly, you know, I flew Richard Branson for a year and a half. I live in London. Best flying because I got to learn the world. Wait, wait, so you're flying Richard Branson. Now this is a corporate private jet. Correct. And you're just flying. Well, remember, to get the celebrities, I had to go to people that wanted to buy a large, like a Gulfstream, a Gulfstream II at the time. And I had to tell them, you use the aircraft, I'm gonna lease it out three months a year, which will pay for the aircraft for the whole year. And so I got people to give me airplanes on that financial agreement. They're putting up the money? Yes, correct. That's how, okay, so that's how you're doing this with very limited money? Correct, yeah, correct. I'm doing it without any, there's no Ken Capital at this point. I don't even have, I got the $500 from dad. So now, go into the 90s, and along concurrent with building this business, once you have the large cabin, filling in the rest of the fleets, it's kind of easy, because people think if you can do the big stuff, if you can travel the world handling my airplanes, so we, you must be qualified. So we start to build a managed fleet of aircraft till it gets to in the low 20s. And there's, when you build businesses, there's these steps, right? Like without any other help, I could run three airplanes myself. You know, but then if I want to run 15, that's kind of the next step. I need 17 people to run 15, and then I need 17 till I get to 30. And then when I get to 30, I need 35 people. There's these steps of infrastructure. So I'm about where I need to be, and early, and so in the early 90s, we don't even realize this today, but today, big manufacturers, Gulfstream, Bombardier, Cessna, they pre-sell their aircraft, and they don't build them if they're not sold. But going back, so going back to the 90s, they looked at it like the car industry. Cessna had a dealer network, where people, to be a dealer, the level of dealer, if you bought three single engines and one twin engine, you were this level. If you bought four twin engines, you got this commission structure, and you were a larger dealer. But when the business didn't sell, there were all these whitetails. And so- Wait, what's that? A whitetail. So a whitetail is a plane that doesn't have an N number on it, because they don't know who to title it to, because it's not sold. Okay. So it was like the auto industry. They kept the manufacturing run going, and if sales couldn't keep up, then they just parked them in a lot and called them whitetails. Well, the Gulf War I happens in 1991, and it goes ahead that these whitetails, Hawker has these whitetails, and Richard Santulli, who was the founder of NetJets, goes to Hawker and says, you can't sell the airplanes. I'll take 20 of them and sell them on consignment, fractionally. Is that the first- This is how fractional- That is the invention of- That's the invention of fractional ownership. Rich Santulli, brilliant, realized that the average company flies an airplane 300 hours a year. A plane wants to fly 1,200 hours a year, so why don't we get four people to share them? What does it mean a plane wants to fly 1,200 hours a year? Well, because if you look at a lot of things, number one is an airplane doesn't like to sit around. They break when they don't fly. The fluids leak out, so they want to fly, number one. Number two, they have the capacity to fly 1,000 to 1,200 hours a year. So an average corporate owner at that time was leaving the plane in the hangar five days a week. And so why not utilize that dead asset? That was his vision. And so he initially thought, well, if I get four people to each put 200 hours on the plane, that's kind of the perfect, so I'm gonna sell the planes in quarters, which is why if you see NetJets' end number today, it still ends in QS, quarter share. Because originally, they only sold 200 hours. Now, today, you can buy 100 hours, 75. But that was his vision, and he sold these whitetails, these consignment aircrafts. So he never put up any capital. He said, if I sell them, I'll give them back to you. So all of a sudden now, this becomes in vogue, and where is he stealing customers from? Me, the charter operator. Because in the charter business at that time, if you took my plane and went to Florida, I had to charge you to return the plane back to Cleveland, or otherwise, how did I get it home? He had the idea of this floating dispatch. I'll drop you in Florida, and then the next client, I'll figure out how to get them from here to there. Well, that was attractive to a lot of different companies, and so he was starting to steal business. I got a little nervous. So between 1993 and 1996, I'm watching this unfold, and I say, well, he's selling these brand-new assets because he's getting them from the manufacturers on consignment. I'm gonna go into the used market, and I'm gonna buy them used, pre-owned, previously enjoyed, I like to say, and I'm going to go ahead, and I'll have the exact same airplanes he did. So whatever NetJets had, if they bought brand-new hawkers, I had a used hawker program. If they brought brand-new citations, I'd just emulate them, had a used citation program. That was my vision. I would be buying them used at half price, so the service is the same. It's still, you can fly. You only pay for it when you're on board. It's just the buy-in is gonna be 50%. That was my vision. Unlike him, I couldn't buy these on consignment. I had to have capital to do it. So in 1996, I put together, this is my first time really starting to look at a business. It's the first time I kind of understand the depth that I have to present, the presentation, looking at cash flow and projections, and I go out to different banks, probably 35 or 40 of them, with this idea of funding me the amount of money I need to start the business. I think I needed 30 or $40 million. I wanted to borrow it. And they look at me and the banks are like, we don't get it. Like, where's our collateral? We have the tail of the airplane you're selling out. Like, how do I have a quarter of a plane? So none of them were a buyer. I think at the end of 12 months or 15 months of being on the road, I had maybe seven million of opportunities. If I put up assets equivalent to seven million, it was the worst financing ever. In June of 1998, Warren Buffett buys NetJets for $750 million, and he christens the industry. And I just happened to be the guy who saw the banks blast. And that summer, I got almost $300 million of debt financing. So again, accidentally wealthy. Because they're like, well, Warren is doing what we want. It's a good idea. Ken had a good idea. Yes. Yep, and all of a sudden, Bombardier Capital, Boeing Capital, Fleet Bank, all 50 million here, 50 million there, gave me these lines of credit. And that had allowed me to buy the initial fleet, which I went active October 13th, 1998. But what is the company? Is it still Corporate Wings? No, I branded that product Flight Options. 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He said, we built 11 Labs to break down language and communication barriers, with Deal enabling us to hire and support exceptional talent anywhere. We can accelerate our innovation and bring more voices, stories, and ideas to every corner of the world. Deal is trusted by over 40,000 companies and growing fast. Learn how they can help your business by going to deal.com forward slash senra. That is deal.com forward slash senra. So that's flight options. So you start with how many planes with flight options? Well, once I get the financing, probably 25. Okay, why'd you pick a number like that? There were three different fleets, okay? Two light jets and a medium jet. And you need about eight aircraft to be your core fleet. In other words, if you and me are both gonna buy a share of an aircraft, we recognize there can only be one. Because if you and I wanna fly the same day, who gets the plane? So you had to show the potential prospect that you had a fleet. And eight was about the number that people, you have eight citations, I'll buy one. And then you have, you can service us. So if you had 25 planes to start out, how many customers, when do you hit your limit? We had 100 people is too much? Like, what's the? No, because remember, these are core fleet. These planes never get sold. What I do from this point on is if four people buy the citation, I buy another citation. So these 24 aircraft were all. So you don't stay with 24, 25 for going on? Yeah, and you know what, that's still a model we use today. If you look at our fleet of 365 aircraft, we would tell you that about 70 of them are core fleet. They don't get sold. They're just there to support your, our customer's ownership and a share of a jet. Okay. Yeah, because we need that because on peak travel days, we're gonna have more demand than, there's just not enough airplanes to go around. So we still have that core fleet model. Okay, so but this is called flight options. Yes. How do we get from flight options to flex ships? Okay, so it's a little longer than you probably hope. But a hundred million dollars in sales between October and December. Four hundred. First three months of. David, this was the most amazing thing I've ever seen in my life. People thought it was such a great bargain that they would send me a check. I think the buy-in at that time was like $800,000. People would send a check for $800,000 and say, send me the paperwork, I wanna fly tomorrow. In other words, they loved it so much. They knew they couldn't fly until I had the money. They'd send me the checks and they'd go, send me the paperwork, we'll get to that stuff later. Just let me fly. Yeah. A hundred million in the first three months, 400 million in the next year, and now all of a sudden, I've got a tiger by the tail and no clue, right? Because a business that grows that fast is immensely complicated, particularly for cash flow. And I think at that time, I didn't really realize that in capital-intensive industries, particularly like aviation, the balance sheet is the whole game. It's not the income statement, it's the balance sheet. Forget income, forget EBITDA, it's free cash flow and how strong is your balance sheet? That's what drives that. I didn't know that in 1998. I hadn't figured that all out yet. I'm in my early 40s when this is happening. And so then I bring in an equity partner. So now I have some equity partners around the table. 2000, we have the dot-com bomb. So I've been through four recessions. That was number three. So now the business is struggling a little bit, cash flow's struggling, not volume's struggling. And we decide, you know, when a business is in trouble, there's two things you can really do. Three things, I guess you could close it down. Two is that you can sell it for a song. Or three, you strategically change direction. So you go to the bankers, because your problem is always the credit markets. It's always who's out there for you. And you say, oh, I have a new strategy. I'm going to merge with this company. Here's the projections. And you buy yourself time to see if you can put these companies together. Acquisitions mergers are incredibly difficult. I hate them, I don't do them very often. I think they're immensely culturally, they're damaging. Why do you hate mergers? I hate them for me, because for me, I think they're a sign of weakness. Because you can't build your business on your own. You can't, whatever this company is offering you in terms of, let's say it's market share. Let's say they have a part of the market and you have a part of the market. And you say, gosh, we'll capture the market. Well, do you really need to spend 12, 10 times cash flow to gab the market? Would you invest that money yourself and grab the market share? Or do you not have a good enough product to do it? So I think we don't analyze enough what it costs for whatever your logic is for bringing that in. Give me the logic for why you're doing that. And I would tell you 90% of the time, you could probably do this yourself without the acquisition. Now, once you do the acquisition culturally, if you have a business built on culture, which is essential for me, it's essential for us, it's impossible. You could integrate a culture if 10% of the workforce is being added, adding 30%, 40% culturally impossible. And then you're going to destroy your culture. So you probably overpaid. I don't know if the business reasoning is sound. And you really put your culture at risk. So that's why I don't like them. Okay. So, but you were, this was the- I'm in trouble. I'm in trouble financially. So you have to. Yeah, I haven't figured this out yet. You're asking me, this was 26 years ago. I have knowledge that's accumulated since then. So we merged with a company that's also in trouble called Traveler. It's a division of Raytheon. And we do the, we slap it together 50-50. Are they in the same business? What are they doing? Yes, they have a company called Traveler that has a brand new product line, but also fractional ownership. Okay. And Raytheon owned Beach Jet at the time, Beachcraft, Beach Aircraft. And they had merged it with Hawker Beach. It became Hawker Beach. And so they were trying to see, they had Traveler as a distribution channel for their aircraft. So they, it's not making money. It's losing $30 million a year. They slap it together with Flight Options, which was marginally breaking even. We were making money, but not free cashflow. So we put these two companies, consolidate, get rid of the back office. Raytheon wants to focus on missiles and submarines. And in the concept of putting these two together 50-50, we come up with shareholders for a letter. Familiar with that term? Yeah, where you have to- You have to make an offer to buy- Where you buy or sell at the same price. Yes. So I had 18 months to underwrite the transaction. I go to Warburg Pincus. I need an outside, I need an investment partner to do this. They see the model. They value the business at 360 million. I go running up to Lexington, Massachusetts to go into Raytheon to tell them, I'm here with your $180 million. This company was a piece of shit. And now I'm here. I figure, where are you putting the Ken Rickey statue that I found, like, I found all this money for you. And they looked at me and they thought I was stealing the business and they bought me out. Oh. And I'm gone. 2002, I've lost my throne. It was the worst day of my life. I was passionate. I love this business. My friends were in the business. Hold on, we got to pause here because this is very interesting. How much of the 180 goes to you personally? You hit the nail on the head. You have a knack for asking the exact right question. I own 16% of the company. Okay. Fast forward today, the punchline is going to be, I bought this company back and now I have a controlling interest. Who thought the worst day of my life? But still, like you thought, let's go back to like you were. You learned how to be a pilot when you were in college. You grew up middle class in Ohio. Now you have millions of dollars and you just said it's the worst day of your life. This is really, really important because the whole point of this show is like I usually talk to people that do things for a very long time and there's like this new industrial like entrepreneur ecosystem and it's driven by investors and they tell, they give the worst advice to founders ever. They're like start, scale, sell. It's like I've talked to all these investors, or excuse me, these entrepreneurs that sold. They all talk about like this. If you sold something you loved, they're like yeah, but Travis from Uber was in that chair and he made billions of dollars and lost Uber. Ask him how he felt when he had four or five billion dollars dropped in his head. He didn't give a shit. He didn't give a shit about it. Absolutely didn't give a shit about it. Start, scale, get a new investor. It's crazy. So okay, so worst day of your life. Let's take me to that. You were like I thought I was going to have this company. They bought you out. First of all, no one was going to be more passionate about building that business than me. I don't care who Raytheon put in there. It was never going to, you know, these businesses are small margins. They're highly technical. There's not an MBA program at Harvard on how to run private aviation. At least there wasn't at that time. It's become a lot more popular now. You're in your 40s at this point? Yeah, 42. Are you married with children? Yes, at the time. How many kids? Two children at the time. Okay, so you got a couple, you know, tens of millions of dollars, whatever the number is. What's your thought process like? Well, first of all, I always say it was the worst day of my life. I lost my throne. I lost my passion for living. I lost the vision. I didn't have any vision. Like what am I doing now? And then, you know, when you do this, it's horribly conflicting because you don't want the company to succeed without you, right? You had to be the binding force. So you really don't want it to succeed. But on the other hand, you don't want it, you don't want it not to succeed. You've built this baby. Your friends are there. If it doesn't succeed, then your whole idea was for shit. So it's very conflicting. And I got so tired of being in Cleveland and at a restaurant. What happened? People wanted to hear this story because at the time, you know, there's 800 employees. So all, mostly in Cleveland. So I decided I was going to move. This is what we were talking about before. I was like, where do you live? You're like, Arizona. I was like, how the hell did you wind up in Arizona? I just decided I was going to go west of the Mississippi. I was going to be in a big town. It was Denver, LA, or Phoenix. And LA was a red eye to get back east. So I decided, and Denver was a little cold, so I ended up in Phoenix and been there since 2003. So now, nothing to do. I'm in Phoenix. At least I'm not being asked what the hell happened. And Warburg Pincus obviously took a liking to me. That's why they backed me. They said, we want to get more into this space. We'd like to give you $250,000 a year. You'll be our executive in residence. You'll find deals for us, and we'll give you a little piece of the action on whatever you do in private aviation. And I was like, well, wait a second. Why would I do that first? Why don't I go find the deals and then decide who I want to bring in? Why would I just line up with Warburg? Because then they get to say yes or no on a deal. In other words, I come to buy your company, and I have to call Warburg and go, can I buy them? Whereas if I just do this myself, I could come in, make the deal, and then go find the capital. So that's when I started Directional Capital, which was a company, again, an inch wide and a mile deep. We put our website went out. We only invest in an area we know a lot about. I knew people in the industry who needed capital at the time, and they came to me because they knew they didn't have to explain to me what was our cost per hour, what was dispatch availability, what was occupied rate. You knew the ins and outs of the business already. And they trusted me, and then. And you're getting equity in return for cash? Is that what you're doing? Well, you mean when I? Yeah, absolutely, absolutely. It's venture, it's private equity, right? And then they always liked my story. Well, Ken, what mistake did you make that helped me finance my company and don't make that mistake? I played on that. Look, I can tell you where the bodies are buried. And lo and behold, I was working two or three different deals. My partner, Mike Rossi, who came in with me in the early 90s, when I kind of transitioned out of pilot into starting to work more on the businesses. We get approached by Allied Capital, who there was a company called Mercury Air Centers, based mainly on the West Coast. They're in default on their debt with Foothill Capital, a division of Wells Fargo. And we buy this company for $80 million in concert with Allied Capital. What does Mercury do? They're FBOs. They own only FBOs. Fuel, you know, private fuel facilities for private jets. A lot of people are buying up FBOs right now, is what I hear. It's horrible. Why? Well, here's the problem. I started the industry. So I, in many ways, I created this monster. Well, because they're only going to private equity and that we could get into my whole philosophy on private equity, I don't think it's really good. Sorbane's Oxley changed in 2000, right? Those Sorbane's Oxley rules made it so hard to be a public company. But even those companies that are public, still, if you read their annual reports, they have some master besides greed. They have environmental policies. They have social policies. They have policies regarding their employees and their leadership. Private equity has to disclose none of that. They are slowly based upon a return to investors. So they're solely about greed. And so they've taken an industry and just tried to monopolize it. It's a duopoly now in the FBO industry. Again, I started it because I sold the business to Atlantic Aviation, which is one of the duopolists. They're just pushing the envelope and what's the most amount of money we can abscond with from these wealthy people that buy jets? And they'd have this new thing called event fees, which they make up in the morning. A lunar eclipse, let's charge an event fee. You know, I mean, it's just horrible. And I think there's been a real repercussion into the industry now, but we digressed. But you buy it in early 2000. I buy this Mercury Air Center, these FBO chain, the 18 or 19. What did you like about their business that you wanted to buy it? Well, first of all, it was in the vertical I knew. So I knew how to market to corporate pilots. I knew why people wanted an FBO. The business made money on the spread between what they bought fuel for and what they sold it for. So relatively easy business to understand. I had a non-compete. I couldn't necessarily compete in the operating side of the business, so it was available. The non-compete didn't cover fuel distribution or hangar and so on. I can see where it was a very fragmented industry. We had 18 FBOs. It was one of the second largest at the time. And so going out and buying these little mom and pops and giving them four million, three million, we were buying it six times EBITDA at the time. Today, these businesses, an FBO business will trade it 15 to 20 times today. Bought it for $80 million in 2005, and then sold it in 2007 to Macquarie, which now is called Atlantic Aviation. So we built it, about doubled the size of it, and sold it for $615 million. Oh, so that's where you have a, you're getting a huge chunk of cash now. Great, I own 20%. Allied Capital had 80. Okay, so Mike and I. That's really good in two years, considering you had to do something and you couldn't do what you really wanted to do. Great, great. So again, the worst day of my life, I don't, you know, let's just have faith in the future. I've seen none of this coming, right? I've seen none of this coming. But that's where I get the capital, and what do you think happens next? Raytheon's had enough fun with flight options. They've lost $600 million in the years they've owned it. The company's become unionized, and it's a problem, and it's going to crap. So who do they call, Ken, you want to take this piece of shit off our hands? And what do I say? Of course I do. I want my company back. I don't care what shitty position it's in, I want my company back. Think about this one. Financial crisis happens in September, I buy it in December. So how dumb am I? I'm the dumbest guy in the world. I buy this company back in the year of the financial crisis. And what do you have to pay for it? 135 million. Okay. Okay, of which the reality is, because there's payables, there's liabilities we're assuming, the reality is it was around 42 million, and I gave a $27 million personal note, and 15 million in cash. Where'd you back up that personal note with? Just me. How'd you do that? The seller took a note for 27 million. Not a long note, I think three year, a three year note. But I had invested in a couple other small businesses at the time. I had assets, I had a home, I hadn't. Did you have to pledge the home, or no? Oh yeah. Okay, that's what I was getting to. It was a personal guarantee of everything. That's what I thought. Okay, that's what I was getting to. And I did have the $100 million, I used some of that, but I had some net worth out there that was viable. Is this the company that becomes Fleck Jets? Yes, one more step and we're done. Okay. So I inherit flight options back, I decide no capital's been invested, I need a new fleet of planes. So I look around the industry, who's got the best fleet, it's Bombardier. They have these Challenger 300s, which are super mid, this is where the market is going, there's these eight passengers, transcontinental, kind of the perfect fit for the shitty planes I have at the time. Can I pause there? Yeah. Because you said earlier there was 5,000 private jets when you started in the industry in the 80s or whatever that was, then there's 35,000 today. I think I read almost all of them are in America. What is America's share of that? 85% of the market. That's incredible. Yeah, people always ask me, what's your strategy for Asia? Don't need one. Don't need an Asian strategy. There's three flights a day over there. I'm doing 800 flights in the US. Like, what am I strategy to get those last three flights? I mean, what are you thinking? Okay, so you need a new flight or you need new planes and you go to Bombardier. Right. So what I really want is the Challenger 300, but they have a company called Flexjet and they have exclusivity. They only have Challenger 300s. Okay, but Flexjet is also a fractional ownership at this time? It's a fractional ownership owned by Bombardier. Okay. Based in Dallas. But I caught a good sales guy. I caught a guy who was head of sales that when I told him I wanted to buy 20 Challengers, and at the time they were about 15 million a piece, so when I came up with $300 million order, he scratched his head and was like, am I really gonna lose a $300 million order because there's this non-compete with a company we own? So he goes to Pierre Baudouin, who was run, the head of Bombardier, the family's owned Bombardier, the Baudouin family's owned that company for years, still does control it, and I had known Pierre through YPO. He liked me and he said, well, Ken knows aviation and why don't you, he tells Steve, the head sales guy, why don't you see if he'd buy Flexjet? So I went to buy planes and they sold me Flexjet in 2014. Why did they wanna get rid of it? Well, because again, they're in the manufacturing business. To be honest with you, they were financially struggling after the crisis, so picking up, I paid 180 million for Flexjet. Picking that up was 180 million they probably needed at the time. With the 180 million came an order to buy 20 more aircraft. By the way, with the deal, they made me expand the order to have Globals, which I had no idea how I was gonna pay for. I had to buy 15 Globals and they were 40 million a piece and I did not have that $600 million. So where'd you come up with that $600 million? Well, that's again, life is funny. So we signed the deal, we're gonna buy Flexjet. Signing the deal, not knowing how you're gonna pay for the Globals? Well, I knew how to pay the 180, no. I did not know how I was gonna pay for the Globals. I did not know how to do it. So with the buying of 180 million, I placed a billion dollar order for Challenger 300s and Globals, and actually some Learjets, which they owned at the time too. So I placed the order, fingers crossed that we'll ever be able, we'll figure out how to pay for those airplanes later. I gotta get Flexjet in here. They call me up, we're gonna close like in October, they call me up in September and I get the, by the way, I need to come see you. And I'm like, I'm toasted, I'm fucked on this deal because they're coming to tell me NetJets has beaten my offer. Because there's only three companies left at the time. There's Flexjet, Flight Options, and NetJets. These are the, or the Citation shares too. But there's three big companies, and the number two and number three are about to merge, and I figure Warren Buffett isn't gonna let this happen. He's in there, he's coming in to take my bid. So I know they're coming to tell me, and sure enough they sit down and they go, we have a problem with NetJets. And I'm like, oh no. They had Globals there also. And they were not, and Bombardier claims they were not aware that in the contract when they sold the Globals to NetJets, it prohibited them selling them to me. So the message they had to convey was, we can't sell you the Globals. That's not a bad. Whoa, 600 million, I didn't have to worry about that. And of course I went, oh, fuck, are you kidding me? This destroys everything I've been in the vision of. And now fast forward, right, two years later we do the Gulfstream, and part of that deal, we get exclusivity, so now we're the only people that can operate Gulfstreams. Oh, I didn't know this. So NetJets uses Globals to this day? Well, see, what would have happened if they didn't pull that card on me, I would have had to be committed in each category, light jet, mid jet, and heavy jet, to buying the Bombardier product. That was the deal. They didn't want to lose their distribution channel. But they took heavy off the Permac, they took that away because they couldn't sell me the Globals. That opened me the opportunity to go ahead and buy the Gulfstreams, which I did in 2017. Awesome. And now we still buy them today. I mean, we're the largest Gulfstream operator in the world. We have 85 of them. Wow. Yeah, we have more than the U.S. government. Yeah. That's a great start. So now I own Flexjet. Yeah, and then why do you decide, okay, I'm gonna use that name instead of? Well, because flight options were for shit, okay? Flexjet is a better name. The seat had a bad reputation. It wasn't paying its bills. I bought the. Flight options. Yeah. Because they had fucked it up. Yeah. They had lost half their customer base because they gave shitty service. The planes lost cap. They never invested in the planes, so the seats were torn. I mean, it just, the name had a bad reputation. And they were unionized. Yeah. And it's like this bad union reputation, and so Flexjet was the much better way to go forward. Okay, what year are you buying Flexjet? 2014. 2014. Yeah, okay. It takes me the next four years to integrate the two companies, including getting rid of the union. Why four years? Well, culturally, the companies were different. They're exactly the same size about, like 300 pilots each, 600 pilots total between the two customers. Remember, you got the shitty hawkers over at Flexjet, and you have the nice challengers at, I mean, the shitty flight options. Yeah. And the challengers at Flexjet, and the Flexjet customer doesn't wanna be on the shitty hawker. So the integration of trying to get the systems, the economics of putting the systems together weren't that easy. Yeah, a lot harder. Culturally, Flexjet was like, we hate the union, and everybody identified themselves. Well, I'm a flight options pilot. Just think about how do you get uniforms to 600 pilots? You have to pick uniform crossover day. So for a while, you got two different colored pilots flying and you got the blue pilots and the brown pilots. I mean, it just was very complicated, unfortunately. But even though you're going through this difficult four-year period, and this makes more sense now, I've got the whole history of why you hate mergers and acquisitions, and you have a couple experiences that are bad. I have good ones, too. But you still really, you strike me as a supremely optimistic guy. You're just like, yeah, I'm gonna sell this contract. I'll figure out where the 600 million's coming later, right? Do you still have a lot of faith in the fractional ownership business? Absolutely. So you're like, do you know this is what you're gonna do for, this is like your life's work? Yeah, not for this program, but if I showed you the economics of how a charter operator works, how a management company works, and how a fractional company works, and showed you top line, bottom line, and margin, it's the only operationally dynamic model. It's the best model. Rich Santulli, he invented this model, and it was brilliant. Okay, so the four-year period, now we're in 2018. Now you're under Flex Jets. You have the Uniform Pilots. The union's gone. The union's gone, you get the plane. Only time a union's ever voted to for self-representation in the history of pilots. Oh, wow, okay. Only time, yeah. Now you have the planes that you want, the kind of planes that you want, okay? The state of the business there, though, I feel from, let's say that's eight years ago. Has the business doubled in size, tripled? Well, quadrupled. Quadrupled, okay. It's a private company. We're not even going to get into the fact that you almost took it public. Yeah, fuck that. Shoot me, but go on. Yeah, and then you paid, I think, $30 million to get out of the deal. $30 million to get out of it. Yeah, to get out of the deal. $30 million mistake. Well, first of all, why is this so important to you? Because I'm obsessed with family-owned businesses, private companies. It's just, to me, the ideal situation, I have a bunch of friends that are public company CEOs, and they all secretly hate it, by the way. But why was it so important to, in addition to, let's take away the reporting and how difficult it is running a public company, but why did you want to keep your company private? Because I believe in a higher being. I think there's a purpose we have beyond wealth accumulation, okay? There has to be. I've always struggled, and of course, I went to Jesuit high school, so of course I'd have the guilt gene. But I've always struggled with the question, why am I here? It took me till 2018 to really find who I am, why I'm here, to all come into alignment. And it's crystal clear in my life today. I always struggled with it. I could go back to conversations in the late 80s and late 90s when I was starting the business, and I'm asking, how does this business serve others? And I think, fundamentally, I always knew my life had to be about serving others, but always shied away from wealth because that didn't seem like, wealth doesn't serve others, it serves me, right? There's very, you know, wealth seems to be very tempting. So, it took me a long time to find my life. Before we get to 2018 and figuring this out, take me to some of these conversations where you're like, questioning this with your, like, what's your inner monologue? Are you sharing these thoughts with other people? Yeah, in fact, probably, you know, if you were to ask me, like, some of the most influential people in my life, one of the most influential was Father Ted Hesper, who led the University of Notre Dame for 35 years. You know, he ran this amazing institution. He grew it from going broke during World War II because they had no students, to becoming one of the most prominent universities in the world today, right? And he did that over a 35 year tenure as president. And he had an amazing business sense, as well as being a priest. So, you know, he was an amazing resource and had amazing insights. And I remember going to him at a time, he retired from president, so he was very available. I ran the student government when I was there, so I knew him from my days at Notre Dame. And so you go to him. And I ask him a question. And I asked him, I said, you know, I'm pretty sure that Jesus was not a capitalist. I'm pretty sure he had to be a socialist because I don't recognize anything in what I was taught about why we are here in the life of capitalism. I don't see that. I'm not finding that. And I said that to him and he looked at me and he said, I have two thoughts for you. Number one, it can be if it consumes you. I actually said to him, I said, you know, I got a shitty gift. You know, if I could cure cancer, that would be a great gift. If I could like heal the poor. I mean, there's a lot of good gifts. There's a lot of very altruistic gifts. I don't have that gift. I got the gift for looking at a balance sheet and understanding how the business could translate to the balance sheet. I understand that that's my special gift. And he said to me, yeah, you can, God thought enough of you to give you that gift. You're going to be tempted your whole life with being selfish with this gift or thinking about how to continuously use this gift for others. But God had enough confidence in you to give you that gift. And so run with it. And number two, he told me, don't overthink this. He goes, life is really simple. We want to make it, we want to make it so complicated. To have a life of significance, you only have to do three things. Be true to your God, be as good as your parents and champion the causes of underdogs. He didn't say be a Catholic. He didn't say be a Christian. He said, be true to whatever you think is why you're here in existence. Be as good as your parents. Our parents are flawed in so many ways. He didn't say be the perfect parent, but parents come with a genuine acceptance that they want to give life, right? So he said, be as good and then champion the cause of underdogs. Always look around the room, find the underdog and go to them. Okay, so you're having these conversations with people you trust and yourself for several years. And then you said you didn't really figure out why you're here until 2018. What was the answer that arrived in 2018? I want to know my immediate reaction. So remember, I'm still doing a little bit of flying. I'm flying these rock stars. I'm flying Bill Clinton at the time, actually. And I'm reading, because when you're a pilot, you have a lot of time to read. You're waiting a lot. And I read a biography about an Indian chief. And in order to become head of his tribe, to become chief, he had to prove that he was worthy of the tribe. And that meant giving away all his worldly possessions. Somehow this sticks with me. I have the conversation. And in 1992, I decided to give away everything. To prove to myself. I saw one of your guests talk about, I think it was about having a tooth procedure without Novocaine to prove he had courage. Everybody's seen this. That clip got tens of millions of views. That's how I know it. That wasn't my courage. My courage was to give away all of my assets. And then to build them back up? Well, it didn't matter. I had to prove to myself that that wasn't what ran my life. That the accumulation of wealth wasn't going to be what ran my life. That I had the courage to use the talent I had, not for self-accumulation. Okay, so this is kind of what we were talking about before we were recording. I told you this fantastic lunch I had with Sam Zell. And his whole thing was just like, he's like, I know all the rich guys. You'd be surprised how miserable most of them are. They have more money than they'll ever spend. They trade time, which they can't get more of, doing things they don't like for more money they can never spend. He's like, there's only one true luxury in life, and that's like, get your private jet money. That's what, that's the advice that he gave me. Because he's like, he's bought everything in the world, and he's just like, it doesn't matter. He's just like, the thing that made him the happiest wasn't his compound in Malibu or his place in Chicago. It was every year, I think, between Thanksgiving and Christmas, he took his entire family, his extended family and everything, and he was able, it was like 35 people, and he would take them to this little village in France for a few weeks, and be able to pay and provide that experience for every single person, right? And his whole thing was just like, you're not going to be happy on the things that you consume. It's the things you do for other, exactly, what you do for other people. You're happy in what you give away, not what you take in. So, but bring me to this realization, so you did that in 92, but bring me to this realization in 2018, where it's just like, now I know for sure. Well, let's say two things, right? In 92, even though, you know, now I'm giving away everything, so I have not, you know, that was a proof again. But again, I didn't have a lot of wealth. I had that nice event, I had the nice event in the middle. I mean, don't get me wrong, I'm wealthy, but I'm not this wealthy, okay? You know, today, I mean, it's a factor of 40 compared to what it was in 2006, right? So, but, well, I don't, you know, that just means the temptation gets greater. No, no, it's not the temptation, it's just like, one of my favorite lines in the history of entrepreneurship is that, it comes from Henry Ford, he says, money comes naturally as a result of service. And so his whole point is like, if you want to make more wealth, that's fine. Find a way to make somebody else's life better, and then the way you make more wealth is increase the amount of people's lives that you get better. And if you just focus on service, the money will come back to you. All right, interview's over, you just captured everything, right? I mean, I will tell you, I mean, if you asked me, I would say, look, six things. Be passionate about what you do, compassionate about how you do it. Memories are worth whatever they cost to create. Friendship is a one-way street. It's only what you do for your friends, it's not what they do for you. Don't miss the best five days of your life. These are, you never know what they're going to be. So wake up every day with the idea that what a wonderful day this could be, right? So those are the things that cross my mind. And by the way, there's no downside in doing something for somebody you don't like. Doing something good for somebody you don't like. No downside in that. I think it's excellent advice. That's a perfect place to close our first conversation. I really enjoyed meeting you. I was looking forward, I've heard nothing but great things about you. I will end a little different than I normally do. What I will say about your business is a lot of my friends use FlexJets and they all talk about the same thing. It's like you have remarkable customer service. And these are highly disagreeable, high-powered entrepreneurs that are not easy to please. So you should be very proud of the business that you've built and one that's growing rapidly right now. And I hope you hold onto it. I know you just sold about 20% of it, whatever the case is. But I think there's good things in the future of FlexJets. Let me say one thing about customer service because you brought it up. One of the keys to customer service is, you know, if there's a problem, because customer service is about what you do when things go to hell. It's not about what you do when things are going well. Within our organization, there is no approval process. The person you talk to on the phone when you call and schedule your trip and you say, we had a breakdown, I gotta get this, that person has all the authority to comp your trip, to give you whatever money they need. They don't have to call a supervisor to say, David needs help. So I empower everyone in the organization at whatever level. First of all, it says trust, which is the foundation. It says that I trust this throughout the organization. That carries trust to that person. But this is a person making $80,000 a year that can comp you a $300,000 trip. So that's how we think about customer service. I love it, thanks. Great, great. I hope you enjoyed this episode. Please remember to subscribe wherever you're listening and leave a review. And make sure you listen to my other podcast founders. For almost a decade, I've obsessively read over 400 biographies of history's greatest entrepreneurs, searching for ideas that you can use in your work. Most of the guests you hear on this show first found me through founders.