Nick Kennedy: Making A Significant Rift In The Status Quo

Nick Kennedy built Rise, a private aviation marketplace that hit 97 NPS before selling to Surf Air around 2017. After the sale, personal breakdowns led him to executive coaching focused on vulnerability and principled leadership. He's now an author and coach working with executives on legacy and character.
Questions this video answers
March 2, 2022
Over 2 million airline miles
2014
Sold to Surf Air (California); sale around 2017–2018
2017 EY Entrepreneur of the Year; Dallas Business Journal 40 Under 40
Chapters
Welcome to beyond you'd why Podcast, where we go beyond just talking about your why and actually help you discover and then live your why. You see, we believe that knowing your why, that driving force behind every decision you make and every action you take, is the essential first step to really knowing yourself. It allows you to move forward faster and have a bigger impact. If you're already a fan of the show, then you know that every week we talk about one of the nine whys and then we introduce you to somebody with that why so you can see how their why has played out in their life. This show will be more powerful for you if you've already discovered your why. If you still need to do that, head over to whyinstitute.com and discover your why today. It'll only take you about five minutes. Now let's meet today's guest.
Welcome to beyond you'd why Podcast, where we go beyond just talking about your why and actually helping you discover and then live your why. So if you're a regular listener, you know that every week we talk about one of the nine whys and then we bring on somebody with that why so you can see how their why has played out in their why their life. So this week we're going to be talking about the why of challenge. So if this is your why, then you don't believe in following the rules or drawing inside the lines. You want things to be fun and exciting and different. You rebel against the classic way of doing things. You typically have eclectic friends and eclectic tastes because after all, why would you want to be normal? You love to be different, think different and you aren't afraid to challenge virtually or anyone or anything that is too conventional or typical for your taste. Pushing the envelope comes naturally to you. So today I've got a great guest for you. His name is Nick Kennedy. Nick is a serial entrepreneur and an executive life coach with over 20 years of experience building successful ventures. After accumulating over 2 million airline miles, traveling for work while losing hours of productivity and family time, Nick founded Rise in 2014, a private airline. Rise created a two sided marketplace that connected busy business executives with private plane operators to redefine travel and in order to regain control of wasted time. Prior to Rise, Nick began his career as a business development manager for eds. He then went on to build multiple healthcare centered businesses. Now as a coach with over 4000 hours of experience for high powered executives, he helped stuck executives become fully integrated spouses, parents and business people. Nick was named the 2017 EY Entrepreneur of the Year and awarded Dallas Business Journal's 40 under 40 and and serves as a Capital Factory mentor and on the boards of several companies. He has been featured in the New York Times, the Wall Street Journal, D Magazine, Texas Monthly, Dallas News, and the Dallas Business Journal. Nick splits his time between Texas and Colorado along with his wife Angela, and kids Will, Sam and Jane. Nick, welcome to the podcast.
It's great to be here. And I feel seen as you were, as you were reading off the challenge or I just was, I thought you must be talking to my wife because I feel very seen. You're spot on there.
Well, let's talk about that for a moment. So, Nick, take us back in your life. Where were you born? What were you, like, in high school? Where did you grow up? Kind of take us back to those years and let's learn a little bit about you.
Sure. I was born in Colorado and lived there until I was 10 or 11 years old and ended up moving out to California to San Diego, where I spent from 11, 12 years old until I was 18, and so grew up in two of the most beautiful places in the world. And, man, I really enjoyed exploring. And I incredibly curious and I was always kind of pushing the boundaries. My report cards when I was young was, you know, Nick will never, you know, Nick talks, he gets good grades, but he talks too much. Right. Like, tell him to be quiet. And I, I guess it was just what I was born with. I just, I had a lot of things I wanted to share, and that turns out to be a great skill set for entrepreneurship.
So what were you like, Give us an example of how you thought outside the box, how you didn't follow the rules, how you were that kid that was, quote, unquote, different.
Yeah. You know, honestly, during the time, I didn't really think about why I was doing it. I just.
I was annoyed. I was annoyed that things weren't a different way. And when I would question them to the powers that be, I wasn't satisfied with most of the answers. And so that led me down the path of exploring further why it couldn't be different. And nine times out of 10, I found the answer. We've got thousands and thousands of years of human history that has gotten us pretty efficient with how we live our lives. But if you do that enough, you start to find these inefficiencies. And that's where goodness comes from, and that's where entrepreneurs really thrive. I mean, entrepreneurship really is building a business. It's a French word. It means bearer of risk. But entrepreneurship is really just being annoyed with something and thinking about it all the time. Right. Until you get it fixed.
And so that's kind of what I was like as a kid. It's just really curious to understand why things couldn't be different. The things that particularly annoyed me.
Yeah. So I like that definition. I'd not heard that before. So entrepreneurship is just being annoyed with something long enough that you can't stop thinking about it, so you have to do something about it.
Yeah. I mean, that really what. That's what it breaks it down to. I mean, think about. I mean, just look at Elon Musk, right? Who's the uber entrepreneur, right. $200 billion in net worth. I mean, the guy is just like annoyed with things now. I don't think he's a particularly healthy individual, but that's what you get when you get the extreme of man. I just want. I want something to be different. I'm going to go find a way to go do it. And I think. And what's so cool about that and why I associate and identify as an entrepreneur is that's what moves society forward. Nothing changes until someone gets annoyed enough to go do something about it. And, and that. And we've seen that over and over and over again. Entrepreneurship. You know, my book that just came out, Entrepreneurship, I posit that it started 80,000 years ago on the shores of Morocco where these snails lives. And the locals there on the, on the shores of the beaches of Morocco, would take these snail shells, paint them, put holes in them, and they found them. They found them hundreds of miles inland. And the theory is that they were using these to trade with other goods that the tribes further in had. 80,000 years ago, Neanderthals and Homo sapiens roamed the Earth together. And the reason, the main reason they think Neanderthals died off is because they couldn't share their resources. When they had bigger brains, bigger bodies, they were stronger. They should have been the dominant race. And yet here we are as Homo sapiens. And what I'm putting forward is the reason we're here in Neanderthals have died off is because we learn to share and take risks to go to the tribe down the way that didn't look like us or talk like us or eat the same stuff with like us. And we said, hey, you've got a little something I need. I've got a little something you need. Let's see if we can't work this out. So I think it's the third invention of mankind behind the fire and Stone Tools is entrepreneurship and that's what's led to growth as a human species. I love that.
That's really. I hadn't thought of it that way. So tell. Okay, so you finished high school in San Diego. Take us on your journey now. You went off to. Did you go off to college or you started into business or. Tell us what happened with you.
Yeah. So still in high school just to stay there because I had kind of this seminal moment in my life. I grew up upper middle class, had a lot of privilege. And When I was 16, my dad was sentenced to 20 years in federal prison. So you want to put a shock in the system. You, you take a kid who's been given almost everything and then. And then tell them you got to go get two or three jobs to help your mom pay rent. Right. Like, it was a shock to like, wow. Lots of trauma, a lot of things I processed over the years and it really forced me to reckon with this new position in my life. And, you know, I realized everybody's starting line in life is completely different. Right? Some are. I was, I was started ahead of the starting line. Right. White man in America. Some are positioned at the starting line, some behind, some outside the stadium. But we've all got these different starting positions. My starting position changed drastically when that happened. But I'm incredibly thankful because I got to see these vastly different lives, which was that of someone who didn't really worry for much to man, I don't know where the next meal is coming from. And so by the grace of God, I got a baseball scholarship to go to a little school in Arkansas called Harding University. And I landed in Arkansas in August. It was 120 some degrees. I mean, everybody talked funny, the food was all fried, everybody had funny haircuts, and everybody had shotgun racks in their trucks. And I grew up in San Diego. I had this long blonde hair. They called me Sunshine. They made me go get my hair cut on the baseball team. I mean, you could have put me in Belgium and I would have been more at home than I was in Arkansas. But six months later, I met my wife in college and the rest is history. I love was a great experience there in Arkansas.
So what did you go into for your degree?
So I have a business management degree with a minor in finance. So I was always kind of driven towards. Towards business and that was my background. Although, you know, for all those out there who are wanting to get into business, I. Harding's a great school. I use about 3% of what I learned in college. Not because, you know, not because I just have to kind of go in there and figure out, figure out what your, how to navigate your, your life, if you will.
Okay, so playing baseball, met your wife, graduated, now you're off to start your career. Where did your career start?
Yeah, so the only job I got out of college was a job at eds. EDS was the famed company or the company that Ross Perot started. And you know, I learned a lot. I learned two main things there. Number one, I got to witness the legacy of Ross Pro. He had left when I was joining the company, but man, his legacy was large on that company. Very few people know this, but there's a book that was documented, this called on the Wings of Eagle. But when the fall of the Shah of Iran happened, EDS employees were in Iran digitizing their health records. Back in the 70s, that's what EDS did. They took two EDS employees hostage. Jimmy Carter famously tried to negotiate their release and failed. Well, Ross Perot was famous for hiring a lot of Vietnam veterans. They would come back and he'd put them through a two year training program and make them computer programmers because he needed computer programmers. He wanted to employ these men and women that were coming back. And if you didn't want to do computer programming, he became part of the security detail. So he ended up hiring and giving basically a blank check to these commandos to go rescue his employees out of Iran. And it's all documented in, in on the Wings of Eagles. But he was that kind of employer. Like it went beyond profits. It was never less than profits, but he meant he really felt deeply about what he was doing and who his employees were. So I, so number one, I learned about that from Ross Pro. And the second thing I learned, I was a, I was a financial analyst and I learned that if I did that for more than 18 months, I was going to jump off a tall building. I mean, I just could not, I could not sit in a cube and know exactly what I was going to be doing on the 13th business day of next month. I mean, that was going to drive me nuts as a challenger. So those are the two things I learned from eds. And from there a good friend said, hey, I'm going to start this business. Would you care to join? And I said, yes, anything to get out of here. And everybody said, you shouldn't do that. And I was warned about it. And startups are hard and blah, blah, blah, and they were all right. And at the end of the day, I loved it because I got to it opened my eyes to this Idea that you could have an idea of something that had never been done before and given enough resources, time, opportunity, luck, any entrepreneurs had, any success will admit that they've had luck. You can go create a whole new category that didn't exist before. And I became addicted to this idea that.
I could, I could go create new things. And I got to see that up front and I got to see a lot of things I wanted to do, a lot of things I didn't want to do. And that became my journey of startups of which I'd been doing and I've been doing for 20 plus years.
So it sounds like you probably weren't a very good employee.
I'm a horrible employee. I'm basically, especially at this point, Gary, I'm basically unemployable. And I say that proudly. But no, I mean, I say take that. I worked hard, I was diligent, I was always the top. But yeah, I mean, I just, I question too much. I mean, these corporations, they thrive on processes and I get it. And there are people that do that really well and God bless them because we need that in a lot of ways. But it's just not what I was designed to do, what I was called to do. It's not anywhere close to my why.
So how did you get into. So then you started doing a lot of traveling because in your bio you mentioned. Yeah, you did a ton. You put in 2 million miles on the airlines.
Yeah, yeah. So over the course of 10 years, building two different businesses, I accumulated 2 million miles on American Airlines. And which meant I was, because I was the top of that was Executive Platinum and I was up in first class nine out of ten times. I mean, I got all the best that they could give me. And for the first year it was super cool, but man, the next nine years, it was just a beating. I mean, nobody wanted to be involved. The flight attendants were frustrated, the baggage people were frustrated, the check in people were frustrated, the passengers were frustrated. I mean, we took this, what is one of man's greatest inventions, the gift of flight. And we've made it miserable. I mean, give us enough time and we'll just ruin anything.
And I'm looking at the situation going like, this is driving me nuts. I'm gaining weight, I'm unhealthy, I'm not around my friends or family. I get home at Friday night just exhausted. Just get enough rest to go back out on the road on Monday. And at the time, I don't know how it is now, but at the time Only healthcare and insurance rated lower on the scale of, of customer satisfaction than airlines. And so that's what I was doing. And one of the investors in one of the startup businesses had a private plane. And I got to experience that. And my eyes were opened to this idea that you could take effectively the same technology.
One'S a little bit larger, one's a little bit smaller, and have a ten times different experience. When you fly private, you come to the gate, the security gate, you hit the intercom, you tell them what tail number you're flying on. The gate magically opens, you drive right up to the plane, the attendants come out, pop your trunk, they get your bags, you get on board. The flight attendant says, hey, you know, here's your almond milk cappuccino and your Wall Street Journal in New York Times. A pilot kind of briefs you on the weather and like it's, it's this unbelievable experience. You land, there's a car waiting for you. And I got to experience that. And I thought, wow, I want a plane. Like I've flown it up on the, on the big boys, I want a plane. And that my frustration of now that I had experienced that I couldn't go back. There's a joke in the, in the, in the private aviation industry that, you know, private planes and crack cocaine are very similar. The only difference is you have a shot of quitting crack cocaine in the future. I mean, you can't quit once you've flown private. And that's what I was, that was my problem. I was now addicted to flying private.
Which led you to then start your own airline.
So I looked at buying a plane. And the reality is buying a plane is the, it's not, while not easy, is the easier of the two, which is operating a plane planet. They're just incredibly expensive. And so I thought, well, what if I get a bunch of my friends together? We could do this. And then I realized, man, I had been doing market research for a decade and I realized that there were lots of people like me who could afford more than first class, but couldn't afford to fly private regularly because it's just so expensive to have your own. And I wondered, what if we could somehow mend those two together? And right at the time, Airbnb and Uber and Lyft, everything was taking off where this idea that you didn't have to own the assets, you could sit in the middle and you could be the two sided marketplace. So I knew for a fact that anybody who flew private wanted to fly private. I knew for A fact people who flew commercial airlines didn't want to. And the only thing I didn't know was how did the aviation industry work? And so I had to figure out how that worked. And what I found out was at the time, the average private plane in America flew just over 200 hours, between 2 and 300 hours a year. So people buy these assets and they sit around and they cost a lot of money.
And I also realized it's an incredibly low margin business because it's mainly airline guys or military guys who come out and want to be in the plane business, and they kind of just do it because they love it. It's a passion business for them. And so I said, hey, what would it be like for you if I could use your planes that are sitting around, use your pilots, et cetera, and I'll bring you more revenue? And everybody hung up on me, and they're like, you're insane. This doesn't work. And finally, a couple said, yeah, let's try this out. And my theory was I would take that plane flying 200 hours, and I would fly at 2000 hours, 10x the revenue on that plane. In exchange, you had to paint the planes in my livery, you had to put your pilots in my uniforms, you had to do all these different things. And it turned out to be a home run, because shortly thereafter, all the people that hung up on me started calling me back and saying, how do I get, you know, access to this? Because we were driving the revenue for them. So my clients on one side, my. My. My customers, my members, we were. We called it a membership man. We had a 97 NPS score. I mean, it was just unbelievable, the experience we were giving them. And then on the other side, when we'd show up to fly to a new city, we'd show up and say, hey, we're gonna buy X amount of thousands of gallons of fuel. Give us the best price you got. I mean, we created this marketplace immediately. It was crazy how. How quickly it kind of all kind of came together. Wow.
So basically, I could just call you. You took somebody's private plane, and how did they feel about you putting eight, whatever that was, 1800 hours on their plane? Did it matter?
Yeah. Well, so. So value it or it does a little bit. But what's interesting about the planes to get just a little technical is every. Every plane manufacturer designates certain things about the plane what needs to be checked. So it's X amount of landings, X amount of hours, all these different things. So once you hit that, you have to do what'? Overhaul and which is, you know, when you hit the major overhauls, you're basically taking the engine apart and putting it back together. I mean they're several hundred thousand dollars kind of operations. And so age on plane and hours on planes are less an issue. The engines we were flying were PT6 engine and yes, rock. Millions of hours are on these things, you know, across, across the world. So it's as long as they're maintained really well. Yeah, devalues at some. But basically it's kind of like a. It's like a Land Cruiser, right? You buy it for $100,000, it decreases to 60, but it's going to stay at 60 forever. They're on out, you know, as long as you're selling them in Colorado or wherever you are. That's kind of what a plane was. And I should clarify the membership. We were selling a flat fee to our members. We were unscheduled service. So it's like an airline. You couldn't just take it whenever you wanted, wherever you wanted. Scheduled service to specific cities, but on a private plane. It was this hybrid between having your own plane wherever and so they paid us regardless. Like they'd pay us a monthly fee if they flew us one time. They paid us the same thing. They flew us 10 times. They paid the same thing. And so we had this recurring revenue. Revenue is gold, recurring revenue is diamonds. I mean it's because it's just mailbox money, right, that you've got coming in regardless. And that was the key was huge, a huge part of our, our success to have that consistent revenue.
Okay. And so it was called Rise.
It's called Rise.
And then what happened to Rise?
So we ended up selling Rise to a company out in California called Surfair. There was a similar type company. The two biggest markets in the country were California and Colorado. I'm sorry, California and Texas. We were talking about Colorado earlier and we were in Texas and they were in California. And either we were going to go get them or they're going to come get us. You had to go through those, those two areas and it worked out that we sold Rise to, to them in California.
Wow. Okay, so then what happened to you? And how long ago was this?
That was 20, 18, 1718 timeframe.
But now what's happened to you?
Well, so you know, you know, you take a kid, you take a kid whose dad goes to prison and you hang a bunch of shame around his neck and he is ought to do what I did, which is I'm going to. I'm going to ensure that you never get an edge on me. I'm going to. I didn't. I feel like I couldn't trust anybody. There was a. There was a kid in my high school, really nice kid. It's not his fault. I'm not going to mention his name, but I remember getting into a fight with him in the locker room after. After football practice one day, and he said to me, you know, after I thought I got the best of him, he. He looked at me and said, yeah, well, at least when I get home, my dad's going to be there. Your dad's not going to be there for the next two decades or whatever. And, you know, at the time, I wondered what everybody thought. No one actually said that to my face. It was the first time somebody had the courage to say it to my face, what I thought everybody was saying behind my back. And I didn't know it then. In fact, it took me about 20 years to figure it out. But I ingested those words as my identity, as I am a child of a prisoner. And I know that now to not be true. And I don't think I had ever said that. But everything in my body was driven towards making sure no one ever knew that about me. I was going to create a trophy room so big and grand that if we ever spent time together, we would never get to my most endearing part, which is.
My side that's hurt, that's broken, that's sad. Those things that are inside of me, because look at me. I'm the guy who started, built, and sold an airline like nobody can. Very few people can say that. And looking back, I don't even really like planes. Like, I'm not in. Everybody I hired loved planes, and I never. And I realized was I was building this thing because it was a killer business, like, in the sense that it brought a ton of accolades. And so I sell the business, and, man, I'm supposed to be on top of the world. And my marriage is in shambles and I'm drinking too much and my kids don't know me. And quite frankly, I took. I was not the best person. And I had to take account of how I treated people. I mean, honestly, at that time, in my mind's eye, there was this giant chessboard of which I placed people according to how I wanted them. I manipulated them in such a way that I needed them to be on my chessboard. And I had to recognize that, number one, no one is mine to manipulate. We're all individual. We have our own agency. And I can't manipulate anybody. I don't have the right to do that. Number two, there isn't some giant cosmic chessboard of which I'm king. And I had to realize that there. You know, the greatest thing God did is make us in his image. And the worst thing he did is make us in his image, because we all think we're mini gods. And. And I had to come to this place where when you pick yourself, you know, I was proud to say I picked myself up my bootstraps, I rubbed my dirt on it, made something of it. I'm the American dream, whatever, right? All the stuff that. Like the cliches that you. You say or hear and then you start to ingest. And I had to do some hard work, and I spent a lot of time with people who love me, who told me, you know, you're a jerk sometimes and you're not kind. And many, you manipulate and you do these things. And man, talk about like a hangover. I mean, you go from up here to down here, and you have to take an account of what are you going to do? And the journey I've been on the last several years is just recognizing that. This book I wrote, the Good Entrepreneur, is all about.
The first 10 chapters of building the businesses. The last two chapters are what I'm talking about now, which is what happens when you sell away your identity. I mean, there's no worse deal in the world than to build your identity into your business and then sell it because you wake up the next morning with a bunch of cash and nobody asking for your opinion anymore. Like, that's a hit to the ego. You talk about a why, right? When you're like, what do you do? What do I do now?
And as I started to tell this story that I'm telling you now to my close friends, and they became safe to me, and I would tell it to more people, the reaction was almost universally the same. They would say. They kind of look over their shoulders a little bit, and they'd say, if you only knew.
As in, if you only knew that the headlines do not match what's going on inside of me. The brokenness that the things I've had to do to get to where I am, the relationship, right? All the things that we all hide. And I started to recognize that my vulnerability allowed people to be vulnerable. And now, I mean, that seems like that was a deep epiphany for us. I mean, for me, Brene Brown, right, is famous for making this known that, you know, if you want to be vulnerable to somebody, if you want somebody to be vulnerable with you, you have to be vulnerable with them. And so I've just been on this mission of I've recognized how isolated I was as a leader. People said, you should go get a coach. You should do this. And I was like, man, I looked at coaches and I was like, man, like, none of them had ever built a business. Like, what are you going to tell me? So egotistical. I mean, really prideful. That was my, it's my sin of choice is pride. And.
I realized I was just isolated, as most leaders are. And so now I come alongside leaders in my, in my life, my vocation now. And I spend time with them, I spend sacred moments with them. And we laugh and we cry and we strategize and we focus and we create clarity and remove static and we get to. What are you going to go do with your life? Because we've only got so many days, 30,000 days if you're lucky. And at our, at our, at our funeral and our obituary, we're going to name 10 of them. And what are you doing spending your time now? And who are you affecting regarding that?
What brought you to that? Take us into that moment when you realized something wasn't right. You'd sold your business, you got all this cash, you're on top of the world. What, what told you. What was that moment where you said, man, I'm not right? What I. This is not right?
Yeah, I mean, if there's one thing we know for sure, we have 2,000 years of empirical evidence that says we can be our own worst deceivers, right as humans. And.
I've seen a lot of success in my own life and building businesses. Aside from the first 30 days, not much of it was fun for me. And I'm really careful to ask the question, not what can you do with your life, but what should you be doing with your life? And should's a very dangerous word. And people use it to, to manipulate people all day long. But.
I can start building, sell an airline like that's pretty impressive in a lot of people's books. That doesn't mean I should necessarily do that. And so none of this was easy. It was a white knuckled grip that my kingdom needed in order for me to maintain my position. And my wife, we've been married now for 24 years. And my, my wife and some friends said, hey, you guys need to go get some counseling. We went to marriage counseling. And, you know, our therapist said something I think is incredibly wise. She said, you know, everybody gets married two to three times in their lifetime, and if you're lucky, it's the same person. And what she was saying is, you guys got married when you were babies. What are the chances that each of you are the same and that the negotiations you made early on are the same that you want right now? And she gave us permission to renegotiate the terms of our own marriage. And we did so successfully. Painfully, but successfully. And after that marriage counsel, I went and I was part of a group at our church called Celebrate Recovery, which is a 12 step based recovery program. It's not specifically for narcotics or alcoholics, not A or na, but it can be. It's just for sin in general. And I was addicted to pride. I mean, pride was my everything. And I spent time with these group of men and we confessed things to each other and we shared things and we did, we got really deep. And there was a man who was my leader. His name was Richard Hoffman. And Richard has since passed away. And he's one of these guys, he was kind of like me. He used to always say, you remind me of myself. Never in doubt, sometimes wrong. And he was a couple of decades older than me, and man, he punched me in the mouth a few times, not literally, but figuratively. And he was one of the first people that I respected enough that I could take his punches and learn from him. And basically, he shared with me 20 years earlier, he. And it's his story, and I, you know, I won't go into it, but he wrecked his life and he spent 20 years trying to fix that. And what he said was, when I wrecked my life 20 years ago, I looked around and there was no one I could talk to because everybody in my business, in my church, in my neighborhood, everywhere, had their lives all put together as he saw it. And he effectively the same journey was he was started to tell his story. And men and women would say, man, if you only knew. So he spent 20 years of his life just being this. He's incredibly successful businessman, incredibly wealthy. He and his wife built a very successful business. But he spent his time walking with people in their lives and creating these sacred moments. And I, by the grace of God, spent the last 18 months of his life on this earth in his presence, where he simultaneously punched me and hugged me and simultaneously wrestled with me and lifted me up. And as he was.
About a week before his death, I went down to his lake house and, you know, I just said, richard, for all you've Done over the course of, you know, 18 months. How can I ever thank you? Like, like I, I finally found peace. I finally found that thing I was looking for that when I, when my life 60, when I was 16, was irreparably, irreparably changed, altered. And he said man, just go forth and do this to other people. Like just be with other people. And I was like, I don't even, I don't know how to do that. And shortly thereafter I got involved in a, with a guy named John Townsend. He wrote the book Boundaries, has since become a good friend. And I was, went through his Townsend leadership program with a group of 10 leaders and so, you know, celebrate Recovery was removing my foundation and tearing down all my preconceived notions TLP or TOWNS and leadership program was my framing and building out my house and putting the roof on. And then I met a guy named Pete Richardson who's in Boulder, Colorado, who walked me through. My wife and I sat down and said help us create a 20 year strategic plan for our lives.
And we did. And he, and we documented it. It was a three day, 72 hour process. It was beautiful. And that was kind of the decorations of the house. And it was a complete tear down. Not like rehab, not like remove everything and start fresh. And that was the process I went through to go from man, not much hope at all. Even though externally everything was going my way.
To man. I don't feel like, I mean I do these deep, deep intense moments with my clients and I come home exhausted and I'm completely.
Engulfed in energy with regards to. And I don't feel like I work a day in my, in my life.
Wow. So question for you, and I'm sure a lot of the listeners are thinking this as well.
Would you have been able to do what you did.
Without being who you were? Would you have reached the heights, the achievement, addiction, the pride, whatever you want to, you know, without the pride. If you had the same perspective you have now, would you have created the so called external success that you did?
Wow. Boy, we're not, we're not playing around here, are we?
Because the reason I say that is you hear often, or I hear often from people that have achieved a certain level of success in their lives that what they achieved wasn't what they thought it was going to be. And then they had to change and they changed themselves. They tore themselves down and became something that they wanted to be after all, but that was after the fact of reaching the levels they got to, you know, will you ever be An Olympic athlete without complete addiction to that sport.
You know, I think this is probably the quest I'm on right now because I think there's a lot of evidence that says you can.
I think I'm doing this in my own way. Like, like the work I do now, the vocation I do now, I feel incredibly successful with and have a lot of.
I'm proud of the work I'm doing. I don't know that it's ever going to be like the New York Times is never going to write another article on me because of the work I'm doing. But I think there's a lot of evidence that shows that you can. Conscious capitalism is an organization I'm a huge fan of and part of. And this idea is never less than profits, but so much more. And they've done it, which is like, yeah, make your money. That's oxygen free business. You've got to make money, make a ton of money. Go for it. Recognize that there are five different stakeholders in a business. There's employees, there's customers, there's investors, there's community and there's vendors. And if any one of those gets out of whack in a business, then the whole will goes off the track. And so when you can make that work really well, you get things like Costco and Southwest Airlines and the Container Store. And they've done studies and said like, you know, it's a. I think it's a 10x certain companies, right? They're 10x growth over an S&P 500 over the course of several years or whatever. So you can do that. However, the people we pull up and say are the great entrepreneurs, the Elon Musk, the Steve Jobs, the Larry Ellisons, the Travis Kalanicks, the Adam Newmans, they are like unhealthy on a different spectrum with regards to relationships. I mean.
I appreciate the work. I enjoy wework. I love Tesla, I love my iPhone. I mean, I really appreciate the work they do. And I think we put these uber entrepreneurs up into this space and say, this is who you should be. And I think we really do it injustice because what we say is they are the ones who are doing it. And the reality is Steve Jobs had 20,000 workers. 20,000 people were behind him. Yeah, he was on stage and yeah, he had the ideas. And we hear all these different stories and they're all very true. 20,000 people worked for him. Henry Ford had 50,000 people working for him. I mean, Larry Allison has 100. I mean, like, the reality is that no one is an island by themselves. And so to answer your question, I think it's. Look, it's real. It's easier to be a jerk than it is to be good. And so I think we often take the shortcut to get to what we want to that saves time initially and ends up really corrupting our legacy long after we're gone. Does that make sense?
Yeah, it does, but I'm not sure if it's. I don't know if you can answer the question right. That may not be an answerable question. We have examples of people that have hit the highest level that did it the way they did it, that they thought they had to to get there. I wonder if you have any examples in your mind of people that did it the way you would do it. Now. Is there somebody you can think of that. Yeah, they created the most amazing. Whatever they.
Herb Kelleher. Herb Kelleher. I mean, the founder of Southwest Airlines, one of the founders. He did that, right? I mean, Herb was this. This rogue. I'm gonna, you know, crazy guy. I'm gonna go start an airline in Texas. Right. I mean, he was a hero of mine in a lot of ways. I met him several times.
And here's your why, by the way.
What's that?
He has your same why.
Yeah. Does he really make sense? Her was this way? I mean, you go talk to the employees of Southwest Airlines. They are loyal beyond reason.
You go to their Halloween party, and it's out of control. I mean, they created a culture around an airline.
A commodity. I mean, airline's a commodity. At the end of the day, they created a culture that makes a difference. Herb Kelleher absolutely can do that. Did that. So I think you could pull a lot of people. I think you look at people like William Wilberforce, who is in. Was a legislative legislation in. In the UK he ended slavery. He used his power for good. Right. I think you can look across the board and see people who. Who did really good things, really successful things, reached the peak of success in their own right, and didn't.
Use other humans. And so to answer your question, like, could I go do it again? Man, I think I don't know. And honestly, that's one of my fears. Like, the question is, like, could you go do that again? Every entrepreneur who will tell you the truth will say, man, their fear is, am I a one hit wonder or two hit wonder or whatever? Like, can I go do it again? Because we know how much it took from us and how much luck played into our success. Mm. So.
I'd like to, I'd like to believe that, Gary, and that's really my vocation now is to come around these leaders and go, hey, let's find a different way to do it and let's go on this journey together.
I think I'm seeing your next book coming to life.
Oh, what is that? What do you, what do you, what are you seeing? The journey.
Exactly what we just talked about. Go do a book on leaders that did it. Right.
I like that.
Right. Ones that you would love to have patterned your life after. Ones that you would be proud to go to dinner with. Ones you would be proud to introduce to your kids.
I like that, Gary. Do I, do I have to put you on as a co writer?
No. Call you man. I'm just taking what you said and putting it back to you. But I could see that as being something very valuable for people that want to do it. Right.
Yeah. Right. Yeah, I like that idea. We need to amplify those voices. Unfortunately, we amplify the, you know, I gotta unpack that some. I don't know exactly why, but we amplify the voices.
We over index and the voices that don't do it the quote unquote right way. That's the, that's the point. That's what I was trying to put forward in this book. The Good Entrepreneur. Right. It's not good as in successful. The understanding is you're going to be successful. Hard stop. That's the bare minimum. What are you doing with your influence after that that's going to make a difference in the world and other people's lives. I like that though. Gary.
Yeah. Okay, last, last question for you. What's the best piece of advice you've ever been given or the best piece of advice you've ever given?
I'll tell you the one that, huh, I'd say the first one that comes to mind and, and I think about it regularly and it's probably allowed me to do what I'm doing right now. So maybe this, maybe my third book is a book I want to write after that one called Micro Retirement. And it's something my wife and I practice where we, we, we do two weeks of. Okay. My wife's an ER physician, so she, she does two weeks of, of work or you know, half, half time shifts and I spend the vocation, I do, I spend doing two weeks out of the month and then we take two weeks off to do non revenue generating work. So my wife, who's been a doctor for a long period of time is now learning to play guitar and write songs. She's got 20 some songs she's written and she wants to go on that path. The book that I just published was my output from that time of non revenue generation. The reason we're able to do that is a guy named Calvin Howe who was a mentor of mine who since passed away.
He.
And his wife came up with this idea that my wife and I have followed, which is create a number. He told me this when I was to college. He said pick a number, make it big, make it outlandish, but pick a number and when you get there, give everything else away. And in college the number I picked was astronomical. I never thought I'd reach there and now it seems.
It'S unbelievable by a lot of standards. But you know.
If I had to pick it today, it'd be a completely different number. But because we have that number, we're able to stop and go, huh, More is not necessarily better and we're able to take a pause and create a more healthy life for ourselves and for our children and for our community. And for two type A go get them personalities like my wife and I, it's the appropriate governor we needed. So the best advice I've ever received is pick a number, make it big and outlandish, but when you get there, give everything else out away and that way you don't become a hostage to it. I know several billionaires and I'll ask them what their number is and the answer is almost universally more. And they don't even know why it's more, it's just more. And it's the American way. And the reality is like we consume things we don't need and we want more and we don't even know why we want more. And so I think that's the best advice I've ever received.
I love it. Well Nick, if there's people listening and there are people listening that would love to connect with you, follow you, maybe be coached by you, spend some time with you, create like you said, sacred moments with you, how can they get a hold of you?
The easiest way is my website, Nick Kennedy coaching. That's N I C K E N N E D Y coaching. I'm on Instagram, Twitter and TikTok now my, my 11 year old daughter's got me on TikTok so I'm trying to reach a whole different generation that way. And it's all Nick Kennedy underscore either IG for Instagram, TT for Twitter or T or TT for TikTok or TW for Twitter. So, you know, if you can follow me out there, I'd love to. I'd love to chat with you guys and, and, and you know, you get a lot of this stuff too in the book and I read the book myself on audio. So if you like the sound of my voice, you can have me read the book to you personally.
Will you tell us again the name of your book title?
Your book, it's called the Good Entrepreneur and the Subtitles and Insider An Insider's Guide to Building a.
Principled Business and a Powerful Personal Legacy.
Love it. Nick, thank you so much for being here. I totally enjoyed our conversation and gave me a lot to think about, so I appreciate that.
Gary, thanks for asking people to figure out their why. If we can do this, man, the world can be a better place.
I love it. Thanks, man.
I really hope you enjoyed today's episode and that through today's guest, you heard how important it is to know your why and how impactful it can be in your life and the lives of those around you. Be sure to head over to why institute.com and discover your why today. Remember, the more you know about yourself, the more you'll know about others. I'm Dr. Gary Sanchez, and I'll see you on the next episode.
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