Nick Kennedy: Making A Significant Rift In The Status Quo

BYW S4 18 | Status Quo


Ever since he was young, Nick Kennedy doesn’t believe in following the rules. His rebellious nature pushed him to challenge the status quo and escape the conventional. He wasn’t afraid to put anything to the test and be out of the ordinary. This mindset brought him success and transformed him into an influential leadership coach. But at some point, he has been seen as odd and is often misunderstood. Nick joins Dr. Gary Sanchez to open up about his WHY of being out of the ordinary, inviting everyone to look at life with a fresh set of eyes. He explains how successful leaders should use their unique characteristics as keys to profound self-transformation.

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Nick Kennedy: Making A Significant Rift In The Status Quo

If you’re a regular reader, you know that every week, we talk about one of the nine why’s and then bring on somebody with that why so you can see how their why has played out in their life. We’re going to be talking about the why of the challenge. 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, exciting and different. You rebel against the classic way of doing things. You typically have eclectic friends and tastes because after all, why would you want to be normal?

You love to be different and think differently. You aren’t afraid to challenge virtually anyone or anything that is too conventional or typical for your tastes. Pushing the envelope comes naturally to you. 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 twenty 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 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. As a coach with over 4,000 hours of experience for high-powered executives, he helps stuck executives become fully integrated spouses, parents and businesspeople.

Nick was named the 2017 EY Entrepreneur of the Year and awarded Dallas Business Journal’s 40 Under 40. He serves as a Capital Factory Mentor and is 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 show.

It’s great to be here. I feel seen as you were reading off the challenger. You’re spot on there.

Let’s talk about that for a moment. Take us back in your life. Where were you born? What were you like in high school? Where did you grow up? Take us back to those years. Let’s learn a little bit about you.

I was born in Colorado. I lived there until I was 10 or 11 years old and ended up moving out to San Diego, California where I spent from 11 to 12 years old until I was 18. I grew up in two of the most beautiful places in the world. I enjoyed exploring. I’m incredibly curious. I was always pushing the boundaries. My report cards when I was young were like, “Nick talks. He gets good grades but he talks too much. Tell him to be quiet.” It was the way I was born with. I had a lot of things I wanted to share. That turns out to be a great skillset for entrepreneurship.

What were you like? Give us an example of how you thought outside the box. How you didn’t follow the rules and how you were that kid that was “different?”

Honestly, during the time, I didn’t think about why I was doing it. I was annoyed that things weren’t a different way. When I would question them to the powers that be, I wasn’t satisfied with most of the answers. That led me down the path of exploring further why it couldn’t be different. 9 times out of 10, I found the answer. We’ve got thousands of years of human history that have gotten us pretty efficient with how we live our lives.

If you do that enough, you start to find these inefficiencies. That’s where goodness comes from and where entrepreneurs thrive. Entrepreneurship is building a business. It’s a French word. It means bearer of risk. Entrepreneurship is being annoyed with something and thinking about it all the time until you get it fixed. That’s what I was like as a kid. I was curious to understand why things couldn’t be different. It’s the things that particularly annoyed me.

I like that definition. I had not heard that before. Entrepreneurship is being annoyed with something long enough that you can’t stop thinking about it so you have to do something about it.

Entrepreneurship is just being annoyed with something and thinking about it all the time. Click To Tweet

That’s what it breaks it down to. Look at Elon Musk who’s the uber-entrepreneur with $200 billion in net worth. The guy is annoyed with things. I don’t think he’s a particularly healthy individual but that’s what you get when you get the extreme of, “I want something to be different. I’m going to find a way to go do it.” That is what’s so cool about that. 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. We have seen that over and over again.

In my book that came out, I posit that entrepreneurship started 80,000 years ago on the shores of Morocco where these snails live. The locals there on the shores of the beaches of Morocco would take these snail shells, paint them and put holes in them. They found them hundreds of miles inland. 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. The main reason they think Neanderthals died off is that they couldn’t share their resources.

They had bigger brains and bodies. They were stronger. They should have been the dominant race and yet here we are as Homo sapiens. What I’m putting forward is the reason we’re here and 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, talk or eat the same stuff like us. We said, “You’ve got a little something I need. I’ve got a little something you need. Let’s see if we can work this out.” The third invention of mankind behind the fire and stone tools is entrepreneurship. That’s what led to growth as the human species.

I hadn’t thought of it that way. You finished high school in San Diego. Take us on your journey. Did you go off to college? Did you start into business? Tell us what happened with you?

It’s still in high school. Let’s stay there because that’s the seminal moment in my life. I grew up upper-middle class and had a lot of privileges. When I was 16, my dad was sentenced to 20 years in Federal prison. If you want to put a shock in the system, you take a kid who has been given almost everything and then you tell them, “You got to go get 2 or 3 jobs to help your mom pay rent.” It was a shock. There were lots of trauma and things that I processed over the years. It forced me to reckon with this new position in my life.

I realized everybody’s starting line in life is completely different. I started ahead of the starting line as a White man in America. Some are positioned at the starting line, behind and outside the stadium but we’ve all got these different starting positions. My starting position changed drastically when that happened. I’m incredibly thankful because I got to see these vastly different lives, which was that of someone who didn’t worry for much to, “I don’t know where the next meal is coming from.”

By the grace of God, I got a baseball scholarship to go to a little school in Arkansas called Harding University. I landed in Arkansas in August. It was 120-some degrees. Everybody talked funny. The food is all fried. Everybody had funny haircuts and shotgun racks in their trucks. I grew up in San Diego. I had this long blonde hair. They called me Sunshine. They made me go get my haircut on the baseball team. You could have put me in Belgium and I would have been more at home than I was in Arkansas. Six months later, I met my wife in college. The rest is history. It was a great experience there in Arkansas.

What did you go into for your degree?

I have a Business Management degree with a minor in Finance. I was always driven towards business. That was my background. For all those out there who are wanting to get into business, Harding is a great school. I use about 3% of what I learned in college. You have to go in there and figure out how to navigate your life.

You were playing baseball, met your wife and graduated. You’re off to start your career. Where did your career start?

The only job I got out of college was a job at EDS. It was the famed company or the company that Ross Perot started. I learned two main things there. Number one, I got to witness the legacy of Ross Perot. He had left when I was joining the company but his legacy was large on that company. Few people know this. There’s a book that documented this called On Wings of Eagles. 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.

BYW S4 18 | Status Quo
Status Quo: You could have an idea that had never been done before. Given enough resources, opportunity, and luck, you can create a whole new category that didn’t exist before.


Jimmy Carter famously tried to negotiate their release and failed. Ross Perot was famous for hiring a lot of Vietnam veterans that had come back. He had put them through a two-year training program and made them computer programmers because he needed computer programmers. He wanted to employ these men and women that were coming back. If you didn’t want to do computer programming, you became part of the security detail.

He ended up hiring and giving a blank check to these commandos to go rescue his employees out of Iran. It’s all documented in On Wings of Eagles. He was that employer. It went beyond profits. It was never less than profits but he felt deeply about what he was doing and who his employees were. Number one, I learned about that from Ross Perot. I was a financial analyst. The second thing I learned was that, if I did that for more than eighteen months, I was going to jump off a tall building.

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. That was going to drive me nuts as a challenger. Those are the two things I learned from EDS. From there, a good friend said, “I’m going to start this business. Would you care to join?” I said, “Yes, anything to get out of here.” Everybody said, “You shouldn’t do that.” I was warned about it, “Startups are hard.” They were all right.

At the end of the day, I loved it because it opened my eyes to the idea that you could have an idea of something that had never been done before given enough resources, time, opportunity and luck. Any successful entrepreneur admits that they have had luck. You can go create a whole new category that didn’t exist before. I became addicted to the idea that I could go create new things. I got to see a lot of things I wanted to do and didn’t want to do. That became my journey of startups, which I’ve been doing for twenty-plus years.

It sounds like you weren’t a very good employee.

I’m a horrible employee, especially at this point. I’m unemployable. I say that proudly. I take that. I worked hard. I was diligent. I was always at the top but I questioned too much. These corporations thrive on processes. I get it. There are people that do that well. God bless them. We need that in a lot of ways but it’s not what I was designed or called to do. It’s not anywhere close to my why.

You started doing a lot of traveling. In your bio, you mentioned you put in 2 million miles on the airlines. Tell us about that.

Over the course of 10 years building 2 different businesses, I accumulated 2 million miles on American Airlines. I have the Executive Platinum. I was up in the first class 9 out of 10 times. I got all the best that they could give me. For the first year, it was super cool. For the next nine years, it was a beating. Nobody wanted to be involved. The flight attendants, baggage people, check-in people and passengers were frustrated. We take what is one of man’s greatest inventions, the gift of flight and made it miserable. Give us enough time and we will ruin anything.

I’m looking at this situation and going, “This is driving me nuts. I’m gaining weight. I’m unhealthy. I’m not around my friends or family. I get home on Friday night exhausted. I just get enough rest to go back out on the road on Monday.” I don’t know how it is now but at the time, only healthcare and insurance rated lower on the scale of customer satisfaction than airlines. That’s what I was doing. One of the investors in one of the startup businesses had a private plane. I got to experience that.

My eyes were opened to this idea that you could take effectively the same technology, one is a little bit larger and one is a little bit smaller and have a ten-times different experience. When you fly private, you come to the security gate, hit the intercom and tell the tail number you’re flying on. The gate magically opens. You drive right up to the plane. The attendants come out, pop your trunk and get your bags. You get on board and the flight attendant says, “Here’s your almond milk cappuccino, Wall Street Journal and New York Times.”

The pilot briefs you on the weather. It’s this unbelievable experience. You land and there’s a car waiting for you. I got to experience that. I thought, “I want a plane. I floated up on the big boys.” That was my frustration. Now that I had experienced that, I couldn’t go back. There’s a joke in the private aviation industry that private planes and crack cocaine are very similar. The only difference is you have a shot of quitting crack cocaine in the future. You can’t quit once you’ve flown private. That was my problem. I was now addicted to flying private.

Give humans enough time and they can ruin just about anything. Click To Tweet

That led you to then start your own airline.

I looked at buying a plane. The reality is buying a plane is not easy. It’s the easier of the two, which is operating a plane. They were incredibly expensive. I thought, “What if I get a bunch of my friends together? We could do this.” I realized, “I had been doing market research for a decade.” I realized that there were lots of people like me who could afford more than the first class but couldn’t afford to fly private regularly because it’s so expensive to have your own.

I wondered, “What if we could somehow mend those two together?” Right at the time, Airbnb, Uber, Lyft and everything was taking off for this idea that you didn’t have to own the assets. You could sit in the middle and be the two-sided marketplace. I knew for a fact that anybody who flew private wanted to fly private. I knew for a fact that people who flew commercial airlines didn’t want to. The only thing I didn’t know is how did the aviation industry work. I had to figure out how that worked.

What I found out was at the time, the average private plane in America flew between 200 and 300 hours a year. People buy these assets. They sit around and cost a lot of money. 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. They do it because they love it. It’s a passion business for them. I said, “What would it be like for you if I could use your planes that are sitting around and your pilots? I’ll bring you more revenue.” Everybody hung up on me.

They’re like, “You’re insane. This doesn’t work.” Finally, a couple said, “Let’s try this out.” My theory was I would take that plane flying 200 hours, fly 2,000 hours and 10X the revenue on that plane. In exchange, you had to paint the planes with my livery, put your pilots in my uniforms and do all these different things. 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 access to this?”

We were driving the revenue for that. My clients on one side, customers and members called it a membership. We had a 97 NPS score. It was unbelievable the experience we were giving them. On the other side, when we would show up to a flight in a new city, we would show up and say, “We’re going to buy X amount of thousands of gallons of fuel. Give us the best price you got.” We created this marketplace immediately. It was crazy how quickly it all come together.

I could just call you. You took somebody’s private plane. How did they feel about you putting 1,800 hours on their plane? Did it matter? Did they value it?

It does a little bit. What’s interesting about planes, to get a little technical is every plane manufacturer designates certain things about the plane and what needs to be checked. It’s X amount of land deeds, hours and all these different things. Once you hit that, you have to do what’s called an overhaul. When you hit the major overhauls, you’re taking an engine apart and putting it back together. They’re several hundred-thousand-dollar operations.

Age and hours on planes are less an issue. The engines we were flying were PT6 engines. Millions of hours are on these things across the world. As long as they’re maintained well, it devalues its sum but it’s like a Land Cruiser. You buy it for $100,000. It decreases to $60,000 but it’s going to stay at $60,000 forever there on out as long as you’re selling in Colorado or wherever you are. That’s what a plane was. I should clarify for the membership, we were selling a flat fee to our members. We were an unscheduled service. It was like an airline. You couldn’t take it whenever or wherever you want it.

We scheduled tourists to specific cities but on our private plane, it was this hybrid between having your own plane wherever. They paid us regardless. They pay us a monthly fee. If they flew one time, they paid us the same thing. If it was ten times, they paid the same thing. We had this recurring revenue. Revenue is gold. Recurring revenue is diamonds. It’s mailbox money that you’ve got coming in regardless. That was a key. It was a huge part of our success to have that consistent revenue.

It was called RISE. What happened to RISE?

BYW S4 18 | Status Quo
Status Quo: Many people could afford more than first-class flying but couldn’t afford to fly private regularly because it’s just too expensive on your own.


We ended up selling RISE to a company out in California called Surf Air. It was a similar type of company. The two biggest markets in the country were California and Texas. We were in Texas and they were in California, either we were going to go get them or they’re going to come get us. We had to go through those two areas. I worked out that we sold RISE to them in California.

What happened to you? How long ago was this?

That was the 2017 to 2018 timeframe.

What happened to it?

You take a kid whose dad goes to prison and hang a bunch of shame around his neck. He has opted to do what I did, which is, “I’m going to ensure that you never get an edge on me.” I felt like I couldn’t trust anybody. There was a kid in my high school. He was a nice kid. It’s not his fault. I’m not going to mention his name. I remember getting into a fight with him in the locker room after football practice one day. After I thought I got the best of him, he looked at me and said, “At least my dad is going to be there. Your dad is not going to be there for the next two decades.”

At the time, I wondered what everybody thought. No one said that to my face. It was the first time somebody had the courage to say to my face what I thought everybody was saying behind my back. I didn’t know it then. It took me about twenty years to figure it out. I ingested those words as my identity as, “I am a child of a prisoner.” I know that now to not be true. I don’t think I had ever said that. 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, broken, sad and those things that are inside of me. Look at me. I’m the guy who started, built and sold an airline. Few people can say that. Looking back, I don’t even like planes. Everybody I hired loves planes and what I realized was I was building this thing because it was a killer business in the sense that it brought a ton of accolades.

I sell the business. I’m supposed to be on top of the world. My marriage is in shambles and I’m drinking too much. My kids don’t know me. Quite frankly, I was not the best person. I had to take account of how I treated people. Honestly at that time, in my mind’s eye, there was this giant chessboard, 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. I had to recognize that number one, no one is mine to manipulate. We’re all individuals. We have our own agency.

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. I had to realize that the greatest thing God did is make us in his image. The worst thing he did was make us in his image because we all think we’re mini gods. I had to come to this place where I was proud to say, “I picked myself up by my bootstraps, rubbed my dirt on it and made something of it. I’m the American dream.” It’s all the stuff and clichés that you say or hear and then you start to ingest. I had to do some hard work.

I spent a lot of time with people who love me and told me, “You’re a jerk sometimes. You’re not kind. You manipulate and do these things.” Talk about a hangover. You go from up here to down here. You would have to take an account of what are you going to do. The journey I’ve been on the last several years is recognizing that. This book I wrote, The Good Entrepreneur is all about this. The first ten chapters are building the businesses. The last two chapters are what I’m talking about now, which is what happens when you sell away your identity.

There’s no worse deal in the world than to build your identity into your business and then sell it. You wake up the next morning with a bunch of cash and nobody asking for your opinion anymore. That’s a hit to the ego. You’re talking about a why, “What do I do now?” As I started to tell this story that I’m telling you and to my close friends became safe to me and I would tell it to more people. The reaction was almost universally the same. They look over their shoulders a little bit and say, “If you only knew that the headlines do not match what’s going on inside of me. There’s the brokenness, the things I’ve had to do to get to where I am, the relationships and all the things that we all hide.”

There’s no worst deal in the world than building your identity into your business then selling it. You may get a bunch of cash but nobody will ask for your opinion anymore. Click To Tweet

I started to recognize that my vulnerability allowed people to be vulnerable. That seems like it was a deep epiphany for us. For me, Brené Brown is famous for making us know that, “If you want to be vulnerable with somebody and you want someone to be vulnerable with you, you have to be vulnerable with them.” I’ve been on this mission. I’ve recognized how isolated I was as a leader. People said, “You should go get a coach and do this.” I looked at coaches and I was like, “None of them had ever built a business. What are you going to tell me?”

It was so egotistical and prideful. My sin of choice was pride. I realized I was isolated as most leaders are. I come alongside leaders in my vocation now and spend time and sacred moments with them. We laugh, cry, strategize, focus, create clarity and remove static. We get to, “What are you going to go do with your life?” We’ve only got so many days. There are 30,000 days if you’re lucky. At our funeral and obituary, we’re going to name ten of them. What are you doing spending your time now? Who are you affecting regarding that?

What brought you to that? Take us into that moment when you realized something wasn’t right. You sold your business and got all this cash. You’re on top of the world. What was that moment where you said, “I’m not right. This is not right?”

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 as humans. I’ve seen a lot of success in my own life and in building businesses. Aside from the first 30 days, not much of it was fun for me. I’m careful to ask the question not, “What can you do with your life?” but, “What should you be doing with your life?” Should is a very dangerous word. People use it to manipulate people all day long. I can start building and selling an airline.

That’s pretty impressive in a lot of people’s books. That doesn’t mean I should necessarily do that. None of this was easy. It was a white-knuckled grip that my kingdom needed for me to maintain my position. My wife and I have been married for years. My wife and some friends said, “You need to go get some counseling.” We went to marriage counseling. Our therapist said something incredibly wise. She said, “Everybody gets married 2 to 3 times in their lifetime. If you’re lucky, it’s the same person.”

What she was saying is, “You got married when you were babies. What are the chances that each of you is the same and that the negotiations you made early on are the same that you want now?” She gave us permission to renegotiate the terms of our marriage. We did so painfully but successfully. After that marriage counseling, I was part of a group at our church called Celebrate Recovery, which is a twelve-step based recovery program. It’s not specifically for narcotics or alcohol. It’s not AA or NA but it can be. It’s for sin in general.

I was addicted to pride. Pride was my everything. I spent time with this group of men. We confessed things to each other, shared things and got deep. There was a man who was my leader. His name was Richard Hoffman. Richard has since passed away. He’s one of these guys. He was like me. He used to always say, “You remind me of myself, never in doubt and sometimes wrong.” He was a couple of decades older than me. He punched me in the mouth a few times, not literally but figuratively.

He was one of the first people that I respected enough that I could take his punches and learn from them. He shared with me years earlier his story. I won’t go into it. He wrecked his life and spent twenty years trying to fix that. What he said was, “When I wrecked my life many years ago, I looked around and there was no one that I could talk to because everybody in my business, church and neighborhood, everywhere had their lives all put together.” As he saw it, he effectively in the same journey would start to tell his story. Men and women would say, “If you only knew.”

He spent twenty years of his life being this incredibly successful businessman. He was incredibly wealthy. He and his wife built a very successful business. He spent his time walking with people in their lives and creating these sacred moments. I, by the grace of God, spent the last eighteen months of his life on this Earth in his presence where he simultaneously punched me, hugged me, wrestled with me and lifted me up. About a week before his death, I went down to his lakehouse.

I said, “Richard, for all you’ve done over the course of eighteen months, how can I ever thank you? I finally found that thing I was looking for. My life when I was sixteen was irreparably changed or altered.” He said, “Go forth and do this with other people. Be with other people.” I was like, “I don’t know how to do that.” Shortly thereafter, I got involved with a guy named John Townsend. He wrote the book, Boundaries. He has since become a good friend.

I went through his Townsend Leadership Program with a group of ten leaders. Celebrate Recovery was removing my foundation and tearing down all my preconceived notions. TLP or Townsend Leadership Program was framing, building out my house and putting the roof on. I met a guy named Pete Richardson who’s in Boulder, Colorado. My wife and I sat down and said, “Help us create a twenty-year strategic plan for our lives.” We did and documented it. It was a 3-day 72-hour process.

BYW S4 18 | Status Quo
Status Quo: It is not enough to be successful. You have to know how to use your influence to make a difference in the world after achieving that.


It was beautiful. That was the decorations of the house. It was a complete teardown. It’s not like rehab or removing everything and starting fresh. That was the process I went through to go from not much hope at all even though externally everything was going my way to, “I don’t feel like I do these deep and intense moments with my clients.” I come home exhausted. I’m completely engulfed in energy with regards to, “I don’t feel like I work a day in my life.”

Here’s a question for you. I’m sure a lot of the readers 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 and achievements addiction without pride? If you had the same perspective you have now, would you have created the so-called external success that you did?

The reason that is 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 they had to change. They changed themselves, tore themselves down and became something that they wanted to be after all. That was after the fact of reaching the levels they got to. Will you ever be an Olympic athlete without complete addiction to that sport?

This is the quest I’m on because there’s a lot of evidence that says, “You can.” I’m doing this in my own way. The work and vocation I do, I feel incredibly successful with. I’m proud of the work I’m doing. I don’t know if 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.” 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. This idea is never less than profits but so much more. Make your money. That’s oxygen-free business.

You’ve got to make a ton of money and go for it. Recognize that there are five different stakeholders in a business. There are employees, customers, investors, communities and vendors. If any one of those gets out of whack in a business then the whole wheel goes off the track. When you can make that work well, you get things like Costco southwest Airlines and The Container Store. They have done studies and said, “It’s 10X certain companies and their 10X growth at S&P 500 over the course of several years.” You can do that.

However, the people we pull up and say the great entrepreneurs like the Elon Musks, Steve Jobs, Larry Ellisons, Travis Kalanicks and Adam Neumanns are unhealthy on a different spectrum with regards to relationships. I appreciate the work. I enjoy WeWork. I love Tesla and my iPhone. I appreciate the work they do. We put these uber-entrepreneurs up into this space and say, “This is who you should be.” We do an injustice because what we say is they are the ones who are doing it.

The reality is Steve Jobs had 20,000 workers. Twenty thousand people were behind him. He was onstage. He had the ideas. We hear all these different stories and they’re all true. Henry Ford had 50,000 people working for him. Larry Ellison has 100,000. The reality is that no one is an island by themselves. To answer your question, it’s real. It’s easier to be a jerk than it is to be good. We often take the shortcut to get to what we want to. That saves time initially and ends up corrupting our legacy long after we’re gone.

I don’t know if you can answer the question. That may not be an answerable question. We have examples of people who have hit the highest level that did it the way they did it and that they thought they had 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 they created the most amazing whatever?

Herb Kelleher, one of the Founders of Southwest Airlines, did that. Herb was this rogue, “I’m crazy. I’m going to start an airline in Texas.” He was a hero of mine in a lot of ways. I met him several times.

He has the same why.

Herb was this way. 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. They created a culture around an airline or a commodity. An airline is a commodity at the end of the day. They created a culture that makes a difference. Herb Kelleher absolutely did that. You could pull a lot of people. You look at people like William Wilberforce who was in legislation in the UK. He ended slavery and used his power for good.

People often take shortcuts to get what they want. Though it may save time initially, it can corrupt your legacy. Click To Tweet

You can look across the board and see people who did good and successful things, reached the peak of success in their own right and didn’t use other humans. To answer your question like, “Could I go do it again?” I don’t know. Honestly, that’s one of my fears. The question is, “Could you go do that again?” Every entrepreneur who will tell you the truth will say their fear is, “Am I a 1-hit wonder or a 2-hit wonder? Can I go do it again?” We know how much it took from us and how much luck played into our success. I would like to believe that. My vocation is to come around these leaders and say, “Let’s find a different way to do it and go on this journey together.”

I’m seeing your next book coming to life.

What do you see in the journey?

It’s exactly what we talked about. Go do a book on leaders that did it right. They’re ones that you would love to have patterned your life after and ones that you would be proud to go to dinner with and introduce to your kids.

Do I have to put you as a cowriter?

No. It’s all you. I’m just taking what you said and putting it back to you. I could see that as being something very valuable for people that want to do it right.

I like that idea. We need to amplify those voices. Unfortunately, I got to unpack that. I don’t know exactly why but we over-index the voices that don’t do it the “right” way. What I was trying to put forward in this book, The Good Entrepreneur is it’s not good as in successful. The understanding is you’re going to be successful at the hard stop. That’s the bare minimum. What are you doing with your influence after that’s going to make a difference in the world and other people’s lives?

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 first one that comes to mind. I think about it regularly. It has allowed me to do what I’m doing. My third book is a book I want to write after that one called Micro-retirement. It’s something my wife and I practice. My wife’s an ER physician. She does two weeks of work. They don’t have time shifts. For the vocation I do, I spend two weeks out of the month. We take two weeks off to do non-revenue-generating work. My wife, who has been a doctor for a long time is learning to play guitar and write songs. She’s got twenty-some songs she’s written. She wants to go on that path.

The book that I published was my output from the time of non-revenue generation. The reason we’re able to do that is a guy named Calvin Howell, who was a mentor of mine who has since passed away and his wife came up with this idea that my wife and I have followed, which is to create a number. He told me this when I was in college, “Pick a number. Make it big and outlandish. When you get there, give everything else away.”

In college, the number I picked was astronomical. I never thought I would reach there. Now, it seems unbelievable by a lot of standards. If I had to pick it now, it would be a completely different number. It’s because we have that number, we’re able to stop and go, “More is not necessarily better.” We’re able to take a pause and create a healthier life for ourselves, our children and our community. For two type-A go-get-them personalities like my wife and I, it’s the appropriate governor we needed.

BYW S4 18 | Status Quo
The Good Entrepreneur: An Insider’s Guide to Building a Principled Business and a Powerful Personal Legacy

The best advice I’ve ever received is, “Pick a number. Make it big and outlandish. When you get there, give everything else out away.” That way, you don’t become a hostage to it. I know several billionaires. I’ll ask them what their number is and the answer is almost universally more. They don’t even know why it’s more. It’s just more. It’s the American way. The reality is we consume things we don’t need. We want more and we don’t even know why we want more. That’s the best advice I’ve ever received.

Nick, if there are people reading and there are people reading that would love to connect with you, follow you, be coached by you, spend some time with you and create sacred moments with you, how can they get ahold of you?

The easiest way is my website I’m on Instagram, Twitter and TikTok. My daughter has got me on TikTok. I’m trying to reach a whole different generation that way. It’s @NickKennedy_IG for Instagram, @NickKennedy_TT for TikTok or @NickKennedy_TW for Twitter. You can follow me out there. I would love to chat with you. You get a lot of this stuff too in the book. I read the book myself on audio. If you like the sound of my voice, you can have me read the book to you personally.

Tell us again the title of your book.

It’s called The Good Entrepreneur: An Insider’s Guide to Building a Principled Business and a Powerful Personal Legacy.

Nick, thank you so much for being here. I enjoyed our conversation. It gave me a lot to think about. I appreciate that.

Gary, thanks for asking people to figure out their why. If we can do this, the world is going to be a better place.


Thank you.

Thank you so much for reading. If you’ve not yet discovered your why, you could do so at You can use the code PODCAST50 and discover it at half price. If you loved the Beyond Your WHY show, please don’t forget to subscribe and leave us a review and a rating on whatever platform you’re using. I will see you all.

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About Nick Kennedy

BYW S4 18 | Status QuoNick Kennedy is a serial entrepreneur and an executive life coach with over 20 years of experience building successful ventures. After accumulating over two 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 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 health care–centered businesses. Now as a coach with over four thousand hours of experience for high-powered executives, he helps stuck executives become fully integrated spouses, parents, and businesspeople.

Nick was named a 2017 EY Entrepreneur of the Year, awarded Dallas Business Journal’s 40 Under 40 and serves as a Capital Factory mentor and on the boards of several companies. He has been featured in NY 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.

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