Welcome to Strategy + Action
Oct. 18, 2023

Ep90 Nick Kennedy - The Audacity to be Successful

Welcome to Episode 90 of "Strategy + Action" with your host, Jason Croft. In this captivating interview, we dive deep into the incredible entrepreneurial journey of the remarkable Nick Kennedy.

 

In the first half of this power-packed podcast, Nick shares his awe-inspiring journey, starting very simply as a college student selling pancakes out of his dorm room. A keen problem solver from the outset, Nick realized he could create solutions and help others along the way. He takes us through his remarkable trajectory, from being part of a company that sold a check-in kiosk business for eight figures to launching and selling a thriving private plane subscription service company, Rise.

 

However, Nick's journey doesn't stop at entrepreneurship; it's just the beginning. Discover how he transitioned into executive coaching for CEOs, where he helps leaders not only confront their emotions but also focus on personal and professional growth. Nick's insightful take on leadership is that it's not just about external strategies but, even more importantly, about understanding one's own emotions and being introspective to make a positive impact on the world.

 

In the second part of this engaging interview, Nick delves into the critical role of a coach and the profound value of having someone guide you through your challenges. He differentiates between offering advice to friends and coaching clients, highlighting how clients are more likely to heed advice due to the financial investment they've made.

 

Nick shares a personal anecdote about his collaboration with Jason to create the transformative "Seven-day Audacity Challenge." This challenge revolves around making audacious decisions to drive personal growth. It's a journey of empowerment and self-discovery that Nick believes is essential to unlocking one's full potential.

 

The interview further emphasizes the pivotal importance of having a coach or mentor who can challenge you, helping you navigate both your personal life and your career. Nick's firm belief in the power of audacity and taking calculated risks is evident throughout the discussion as he draws on his own life experiences.

 

Nick Kennedy goes on to describe his coaching practice, focusing primarily on "tip-of-the-spear" leaders, individuals who are responsible for their organization's payroll. His services extend to one-on-one coaching and a remarkable group coaching program, the "Kennedy Leadership Program."

 

In addition to his coaching services, Nick generously offers a treasure trove of free resources, including his informative newsletter, transformative courses, and a valuable book he authored, "The Good Entrepreneur." The book not only provides valuable insights and a deeper look at his story but also offers actionable tasks to guide you on your journey to becoming a better entrepreneur.

 

Don't miss this extraordinary episode and make sure to check out Nick's newsletter, courses, and book, "The Good Entrepreneur," to ignite your own path to success.

Transcript

00:00:00:00 - 00:00:16:23
Nick Kennedy
Jason. It's been too long, man. Did I say something to offend you last time I was on? Because it's been like. Feels like a decade since I was on your show last night. I'll try not to say anything bad. If that was the case.

00:00:17:01 - 00:00:26:21
Jason Croft
Yeah, well, there's a let's.

00:00:26:22 - 00:00:35:19
Nick Kennedy
Hey, man, we can do. We can do this live if you want. You know, we can just work it out. If I need to say I'm sorry.

00:00:35:21 - 00:00:51:19
Nick Kennedy
Oh, is this. Wait, is this an intervention? And we just. Hold on. Why is my. Why is my mom here? Jason, what's going on? Well, it's my third grade teacher, Jason.

00:00:51:21 - 00:00:55:00
Jason Croft
What?

00:00:55:02 - 00:00:58:13
Jason Croft
Oh, gosh.

00:00:58:15 - 00:01:24:19
Nick Kennedy
The idea that we did okay with Jason and Nic confronting you on your best. Steven's everything you've always feared coming to you live. Yeah, I'm on the show, Ellis. About who you want us to confront. That's a perfect that's a perfect intro. Tell us about who you wanted us to confront. And then we go to them, be like, Hey, we're actually going to actually get to confront your friend who who called you out.

00:01:24:19 - 00:01:32:06
Nick Kennedy
And they're like, Oh, good, I got some. I got some good stuff.

00:01:32:08 - 00:01:39:14
Jason Croft
All right. Is that they said.

00:01:39:16 - 00:01:49:13
Nick Kennedy
You're welcome. It's great to be here. Great to be here.

00:01:49:15 - 00:01:59:04
Jason Croft
Yeah, I like Well.

00:01:59:05 - 00:02:06:06
Nick Kennedy
Well, your Dallas Peeps are coming to you in Colorado, so we're we're following you. So it will all be up there it off, Jason.

00:02:06:08 - 00:02:13:09
Jason Croft
About. I'm coming. Oh, yeah.

00:02:13:09 - 00:03:06:16
Jason Croft
have had.

00:03:06:18 - 00:03:30:22
Nick Kennedy
Yeah, yeah. It's so my career is it's mainly around entrepreneurship. I've had jobs all my life, do entrepreneurial things. There's a kid in college selling pancakes out my dorm room, and it was just kind of this idea that if you could create something, if I had a problem that other people had problems most likely in so I could figure out how to fix my problem, I could fix other people's problems.

00:03:30:22 - 00:03:50:14
Nick Kennedy
And that's all really a great entrepreneur does, right? A great entrepreneur just fix people's problems, great salespeople fix people's problems, and my first job out of college was with Ross Perot's company. It's great company, but I'm just not really a good employee. And I didn't like being in a cube. And that led me to a couple different ventures.

00:03:50:15 - 00:04:09:12
Nick Kennedy
One was a check-in kiosk company that we were checking in people at hospitals that we sold to National Cash Register. And I was young at the time. A friend of mine brought me along who was the founder of the business and said, Hey, come, come do this business with me. And it was just an idea. And three or four years later we sold for eight figures to National Cash Register.

00:04:09:12 - 00:04:29:12
Nick Kennedy
And it blew my mind, like I knew how you could take pancakes and make money. But I didn't realize you could go make tens of millions of dollars. Just an idea. And I got to see this right in front of me. You got to participate a little bit in that. And that kind of led me down this path of I stayed in health care for a while, did some work around oncology, decision support and helped to build that business.

00:04:29:12 - 00:04:49:02
Nick Kennedy
And then the guy who funded that business had a private jet. And in the course of me building businesses, I had spent 2 million miles flying on American Airlines in the course of the decade. So I was one of those those warriors just on a plane all the time. And I hated it. I mean, it was just, you know, at first, you know, the first time you get it, go on a business trip.

00:04:49:02 - 00:05:13:13
Nick Kennedy
It was cool because they were paying for your meals and your hotel and everything. And then about the I don't know when, but somehow it came out. I fell out of favor with it and hated it. And I got to ride on this gentleman's private plane. And I thought, Oh, my gosh, this this is the life. But as I looks into private planes and using them myself, the super expensive, luckily for me, being born at the right time, Uber and Airbnb's were starting to come around, right?

00:05:13:13 - 00:05:35:19
Nick Kennedy
It was the largest transportation company companies, no cars there being these the largest hotel with no rooms. And I thought, why can't we be the largest airline? Where can I create the largest airline with no planes? Right. And it turns out there's a lot of planes that were sitting around being underutilized. And so we built this model where people could pay a subscription, a flat monthly fee to fly on scheduled service on private planes throughout the state of Texas.

00:05:35:21 - 00:05:54:12
Nick Kennedy
And it grew rapidly. And it was just an idea. And I didn't know anything about planes, but I had a great team that that didn't know a lot of things about planes. And we grew really rapidly and ended up selling that business. And so I've kind of been all over the place. I've been on ecology, I've been in planes, I've been in technology most of my life, but really around entrepreneurship.

00:05:54:16 - 00:06:17:05
Nick Kennedy
And after that business, I took a lot of time off and started doing what I do now, which is executive coaching for CEOs. So I get to spend time with CEOs and create these sacred moments with them so they can make the proper decision both in their personal and in their business life. So I've built businesses, I've sold businesses, I've screwed up a thousand times.

00:06:17:05 - 00:06:22:02
Nick Kennedy
I've been part of corporations. So my business background is there's a lot of different things

00:06:22:02 - 00:07:29:18
Nick Kennedy
and yeah, yes, there's this old saying, if you ever find a turtle on a fencepost that didn't get there by itself. Right. And, and I kind of feel like a turtle on the fence posts in a lot of ways. And and as you know so so let me back up a little bit.

00:07:29:20 - 00:07:47:01
Nick Kennedy
I grew up upper middle class. When I was 16, my dad was sent to 20 years in federal prison. So I went from this upper middle class life to this angel tree kid life. And with that, I took on a chip on my shoulder, and the chip on my shoulder was a lot of kids made fun of me because of that when I was in high school.

00:07:47:01 - 00:08:05:12
Nick Kennedy
And and I just thought, I'm never really be made fun of again. And I'm going to do that two ways. I'm going to become a very successful and wealthy, number one. And therefore, I'll be so busy telling you about my high about all my trophies that we'll never even get to like what's inside of me. And secondarily, I'm never gonna talk about my dad because why would I ever bring that that skeleton out of the closet?

00:08:05:12 - 00:08:24:20
Nick Kennedy
Right? And I'm realizing when I after I sold the business and I did some I did a lot of work, my marriage of 18 years at the time. We're still married, been married for 25 years now, I need a lot of work. We did marriage counseling and therapy and I had to do a lot of work on myself, and my wife had a lot to do, a lot of work on herself.

00:08:24:20 - 00:08:44:13
Nick Kennedy
And we did do a lot of work on our relationship. And then I went through a leadership program under John Townsend, who's a great coach himself, probably one of the best there is. I did a Townsend leadership program where I got to spend a year with ten, nine other individuals and a leader learning different kind of skills. So it was like I had a house right prior to this.

00:08:44:13 - 00:09:04:10
Nick Kennedy
We we went through and I decimated that house. I mean, I reconstructed it from from the ground up. And in that process, I started telling my story to other buddies who most of whom were entrepreneurs. We all just kind of, you know, are like coyote who run around parks. Right. You got to see someone who looks like you and you become them.

00:09:04:10 - 00:09:21:21
Nick Kennedy
And and and nine out of ten times, I would say, hey, I'm really you know, let me tell you what I'm dealing with. Let me tell you about my shame and how that manifested itself into me firing this person. Or let me tell you about how I when I should have been dealing with confrontation with certain people, I instead drank lots of Manhattans.

00:09:21:21 - 00:09:39:02
Nick Kennedy
Right. Or, you know, all the things I was doing to mute the emotions that were coming out of me. These these other CEOs would look at me. Nine out of ten would look over their shoulder and kind of like you two like, you're dealing with that, too. And I realized we were all dealing with it in our own way.

00:09:39:02 - 00:10:12:10
Nick Kennedy
We were all separately suffering. And what I know about human beings now is that when you can tell the truth in a safe setting, with a safe person, you can get it out of your mind and out into the ether and then the healing can begin. But it's really, really, really scary to do that and to say the things that you you've been saying in your head that you don't know how to get it out and to trust somebody, that they're not going to run off and tell somebody else.

00:10:12:12 - 00:10:32:01
Nick Kennedy
And what turned into a kind of what I thought was just me doing my own process has turned into a my my second career. And and it's a vocation. And it's one, quite frankly, just I think I'll be doing it for the rest of my life because I, I get to spend time with just people who are at the tip of the spear.

00:10:32:03 - 00:10:58:16
Nick Kennedy
They own sports teams, their Hall of Fame athletes. They're they're they're they're different, really successful people that seem to have it all together, but they're harboring these things inside of them that's ultimately hindering their growth. It's ultimately plateauing them. And so we spend time together and we work through what that looks like. And and I have the coolest job in the world because I get to I love reading.

00:10:58:16 - 00:11:13:11
Nick Kennedy
I'm curious. I like to write. And so I get to read and write and do research and talk to really cool people. And I got to put that on my library. And then in the middle of a conversation, my job is to be able to understand what tools to take down off the shelf and apply to that particular situation.

00:11:13:13 - 00:11:33:13
Nick Kennedy
And, and I guess and so consequently I get to work on myself like I feel like I'm Schine in some respects because as I think about how do I help so-and-so go through this problem, I'm also like, Oh, I'm still deal with that in my life. I should probably apply that to my own life. Let me go have this conversation with this old friend or with my wife or with my child and mad.

00:11:33:15 - 00:11:50:22
Nick Kennedy
It's it's exhausting and it's life giving at the same same time. It's this really weird paradox that I just love.

00:11:51:00 - 00:12:43:13
Jason Croft
Yeah, Yeah. It can't. Yeah, yeah, yeah.

00:12:43:15 - 00:13:06:14
Nick Kennedy
To learn. Yeah. I mean, here's the coolest thing. Like, I dunno if you can see this, Jason, but this is the a, this is a card of emotions, different types of emotions. Right. Here's what's fascinating are about our bodies. There's a book, a great book called The Body Keeps a Score and our body has a physiological reaction to particular situations before we even know what the emotion is we're feeling.

00:13:06:16 - 00:13:28:09
Nick Kennedy
So as an example, when I feel shame, my cheeks get red, my ears get warm and my chest tightens. And I've done enough work on myself and enough therapy and I've studied this enough and then I've got that. I will feel my chest tighten my cheeks, get warm in my ear or my red in my arm, my ears get warm, and I'll think to myself, Why am I feeling shame before I even think I'm feeling shame?

00:13:28:11 - 00:13:57:20
Nick Kennedy
And then I'll go, Oh, it's because so-and-so just said someone's a better coach than you, right? Or you know, you're not as good as you think you are, or you had a or you misspelled something in your email newsletter, right? It could be little, it could be spy. Does it matter? It manifests itself. And I think that's what's fascinating about us as humans is that we actually have these triggers in us, whether it be passion or joy or love or shame or guilt or anger, which often comes out as either rage or annoyance.

00:13:57:20 - 00:14:17:20
Nick Kennedy
Right? Annoyance is a form of anger. But when you can stop long enough to know what you're feeling. And before I went through before I went through this thing called cellular recovery, which is a 12 step program, not for alcohol or drugs specifically, but just in general, like any particular sin in general. My favorite sin was pride is still pride, right?

00:14:17:20 - 00:14:36:09
Nick Kennedy
So I had to deal with that. But before I went through that process, I don't even know there were eight basic emotions, much less what I was stealing at any given moment. I was so reactive and my definition of adulting is being fully aware of your emotions while not letting them control you because you can't control your emotions.

00:14:36:09 - 00:14:59:11
Nick Kennedy
They happen to you. You can control your reactions to your emotions. So when you think about as a CEO, as someone who is on television, as someone who's leading groups of people, right, you're under a microscope. You might say something. We all can think of examples. We don't need to bring them up here. But you can all think of examples where someone goes, they've done something and that forever marks them as who they are.

00:14:59:11 - 00:15:14:12
Nick Kennedy
And the truth is, it's not where they are. It's just a decision they made in that moment. And so when you think about leaders, I think you can I mean, this is going to sound so Pollyannish, but but I think if you change the hearts of leaders, you change the world because we spend more awake time at work than we do anywhere else.

00:15:14:14 - 00:15:30:03
Nick Kennedy
And so if you have a leader leading you who wants to make money, make a ton of money, go for it nevertheless, and profit so much more, but also looks at you as a human and says, Hey, is this the best job for you? Is there a better job for you? How can I help you? Lean into your strengths.

00:15:30:03 - 00:15:48:16
Nick Kennedy
How can I help help you strengthen your weaknesses? How can I tell you some vulnerability about me? So you might be be able to see that in your own self, right? If you have leaders do that across the globe instead of I'm going to milk you for every last drop of energy you have out of you and then I'm going to kick you to the wayside.

00:15:48:18 - 00:16:11:14
Nick Kennedy
That's not capitalism, right? That is at best, that's crony capitalism. And at worst, that's just just pure meanness. And and and so I think I think there's a really big thing at stake here, which is making change the hearts of the leaders. And you change the world because then leaders start to and in a way, you change the heart of the leaders by hand to know himself to actually do a deep dive.

00:16:11:14 - 00:16:26:19
Nick Kennedy
So I do 360 reviews and I have them journal and we talk through a lot of different stuff. And I have all sorts of skills and exercises and tools we go through and it's it's pulling out what's inside of them and it's putting on the table and it's examining that and going not it's good or bad. It just is what it is.

00:16:26:19 - 00:17:26:02
Nick Kennedy
Let's acknowledge it so that we can understand why we do certain things that we do in our life. That becomes a whole level of freedom, right? Money's not freedom. Money is just another prism. Freedom is knowing who you are and being able to do what you love. That's what freedom is really?

00:17:26:04 - 00:18:43:02
Jason Croft
Yeah. Yeah, yeah, yeah, yeah, yeah.

00:18:43:04 - 00:19:04:14
Nick Kennedy
I mean, I'm a great example of that. Jason. I did a lot. I was very successful in business with the help of a lot of people, but it was very successful in business having not done this work. But I'm, but, but I was going to plateau. I was going to plateau because I was turning to, I was turning to crutches in order to mask what was really inside of me.

00:19:04:16 - 00:19:18:05
Nick Kennedy
And so there's these there's these three levels of hierarchy of of leaders. And, you know, the first the first level is, hey, I just do the job really well, right? You give me a job, I do it, I show up early, I stay late and I do the tasks better than you, than you expect. That's kind of the first level.

00:19:18:05 - 00:19:35:18
Nick Kennedy
The second level is you get to lead other leaders and you're you're reacting to problems, right? You're like waiting for the problem to happen and then you're you're reacting to it. That's what I was really good at. That's where 99% of leaders stop that. The metal leaders, like the leaders who become great, they go to the next level.

00:19:35:18 - 00:19:51:18
Nick Kennedy
And what they do is they actually become they go look for problems before they exist. So they are they put their house in order in such a way that they don't have to be reactive. And they go out and they're thinking about what's the problem that's going to exist next week, next month, a year from now, ten years from now.

00:19:51:18 - 00:20:21:02
Nick Kennedy
And then they apply their they their expertise towards that. But when you're so busy reacting to the emotion all the time or you're so busy reacting to to, to to chaos, you can't move forward. And that's the, you know, the yin yang symbol, right? One side is white that symbolizes order, one side is black, that symbolizes chaos. But inside of whites, there's a black dot that symbolizes even in order, there can be chaos.

00:20:21:04 - 00:20:42:22
Nick Kennedy
So you can have a great life, but there still lives this thing inside that can turn into chaos pretty quickly. And here's what's super cool In the chaotic side and the black side, there's a lot of white that's that symbolizes that, hey, there is a chance of rebirth. And in fact, you probably going be much better if you're living in the chaotic life and you reach out into that that order and you think, oh, I want a better way of living.

00:20:42:22 - 00:20:59:23
Nick Kennedy
Right. And and you can't lead other people until you know what's going on. You can't properly lead people until you know what's going on. So, yeah, you can read the books and yeah, you can see all the things and yeah, you can kind of check the boxes, but you can't really be transformational. You can't be the person that they'll that long after you're gone, they'll say, Hey, let me tell you about this mentor.

00:20:59:23 - 00:21:20:13
Nick Kennedy
I had this boss, I had this friend, I had this leader I had. And what they did right, we all had those people in our lives. You can't be that person until you done the work on yourself. And and I think that that's a really important aspect for people, is they're thinking through, you know, when I get an opportunity to sit with someone and coach them and there's a difference between coaching and consulting, right?

00:21:20:16 - 00:21:39:12
Nick Kennedy
And tilting helps them go build their business, that coaching is helping them build their lives both professionally and personally. But when I get to sit with them in those moments, I get to bring to bear how I dealt with my board and how I dealt with my investors and how I dealt with my employees both properly and improperly and give them advice.

00:21:39:12 - 00:22:03:06
Nick Kennedy
I literally had a client yesterday call me and he's having a board is they're done. They're done. The bottom is fallen out. They don't trust them anymore. And they're basically saying, hey, we need to move on. Right. He's just completely tormented because this is his entire identity. And it's easy for me who's not in his shoes to say, hey, man, there is a future ahead of you.

00:22:03:07 - 00:22:20:15
Nick Kennedy
This is the thing before the thing, this is it. Your entire life. And coach him through that process. It's hard for him to believe me. But. But because I've got some skins on the wall, because I had the audacity with a couple of other people to start an airline, he goes, I think maybe I can trust Nick. Right?

00:22:20:15 - 00:22:36:11
Nick Kennedy
And my wife had breast cancer this year. She had a couple major surgeries. The doctor, the surgeon, right before we went in, like we knew he had hundreds and hundreds of surgery surgeon surgeries under his belt. Right. We knew we trusted him. We put our trust in him. That's what a coach does. They go, look, this is my problem.

00:22:36:11 - 00:22:52:08
Nick Kennedy
Help me. And then you guide them on the process and they can choose to listen or not to listen about that. But, man, how great is that to have that, too? And what's cool is they pay me to do it. Jason Therefore, they're going to listen. Like my friends will ask me advice on stuff and I hate to do it because I want to be their friend, not their coach.

00:22:52:14 - 00:23:06:13
Nick Kennedy
But they'll still ask me advice and you know, it's like 5050 whether they take my advice, you're not. But people who pay me, it's like 90% take my advice because they're like, Well, hell, I'm paying this guy. I might as well get my money's worth. And so there's this kind of there's a value exchange that goes on there.

00:23:06:13 - 00:23:22:19
Nick Kennedy
And it's the same thing with you, Jason. Like this last thing that we built together, right? We created this. So, so I sponsored this newsletter. Justin Walsh's newsletter, 70,000 subscribers. And I didn't know I sponsored it. I paid for it. I didn't know what I was going to go to do. And I called Jason. I said, Jason, help your marketing genius help.

00:23:22:19 - 00:23:39:01
Nick Kennedy
And he's like, And we were kind of going back and forth. And he said, What's one word that describes you? And I asked my wife and my son separately, and they both said the exact same thing. They said, You're audacious, dad. And then you came up with, Well, let's create the seven day audacity challenge, which turned in this beat I'm really proud of.

00:23:39:01 - 00:24:02:03
Nick Kennedy
It's this beautiful product. You can go take it. It's free. It's on my website. I'm sure it'll be in the links below or however Jason wants to do it, but it's a seven day odyssey, charted five minute lessons over the course of seven days that says, Hey, everything good in my life happened after I made an audacious decision whether it was asking my wife out and I had no business asking her out, jumping on a plane, going to a college that I had never even been to.

00:24:02:05 - 00:24:16:15
Nick Kennedy
Right. Starting this airline like these audacious moments define my life. And and it's the same thing you did for me. But I had I was I was like a deer in the headlights until you were like, oh, yeah, I got this. Yeah, this is what we should do. And here's the structure and here's our scope. And I probably drove you nuts.

00:24:16:15 - 00:24:33:23
Nick Kennedy
You can tell. You can tell me now or not, but I was like, What about this? What about this? I went back and forth and every time I sent you something, you would say, Yes. And and he would make it better, Right? That's the role of the the coach consultant to you or to me and and yeah, it was almost like you.

00:24:34:00 - 00:24:56:00
Nick Kennedy
I'm sure you and it's 20 years of experience of you doing that but and also I'm sure felt somewhat easy in some respects because you were able to look at me and be like, Oh yeah, yeah, here's our here's our way I do it. But to me, I was completely blind. And you brought me, you brought me clarity, you brought me wisdom and you brought me structure and you did all the things that I needed to have in my life.

00:24:56:00 - 00:25:38:02
Nick Kennedy
And that's the role that of a great coach. Consultant, which you were to me just recently as we built that product out.

00:25:38:04 - 00:25:58:17
Jason Croft
Yeah, Yeah, yeah, yeah.

00:25:58:19 - 00:26:16:00
Nick Kennedy
But the but, but however you do it, you're right. There's a, there's a, there's an easy way to do it, our way to do it. But regardless, just asking for help. I mean I think I lives, I'm, I'm embarrassed to acknowledge how many years in my life Jason I live thinking I didn't need help or I knew I needed help, but I was too scared to ask for help because I went back to my shame narrative.

00:26:16:01 - 00:26:31:15
Nick Kennedy
Oh yeah, you need help because you're the prisoner's kid. Like that was what was going on. I don't want to thinking that about me, but in my mind, that's what I thought was going to convey. Like, Oh, of course you need help. And, you know, that's my pride, right? That was that. That's the thing I still have to deal with is like, not unlike you.

00:26:31:17 - 00:26:56:01
Nick Kennedy
That's something inside of you, Nick, that you need to deal with. You know.

00:26:56:03 - 00:27:53:05
Jason Croft
That can kind of our. Yeah, that. Yeah, yeah, yeah. You know. Yeah, it is.

00:27:53:07 - 00:28:20:00
Nick Kennedy
And here's and here's the, here's the antidote to Jason. If you have a coach, they're going to meet with you regularly and their job is to challenge you on these things. And if you don't have a coach or can't afford a coach, then you've got to find friends who will challenge you on these things, right? Because if you say, Hey, we're going to meet monthly or quarterly or or, you know, whenever we're going to meet, then and here's the purpose of it, I'm going to challenge you on it.

00:28:20:01 - 00:28:42:23
Nick Kennedy
You want you to ask me these questions, We're going to go through like that's that's a regular thing. It doesn't have to get to the breaking point because, you know, I've got a monthly meeting coming up. I have a conversation about that. I had just I had been searching for a coach for years for myself. And candidly, I there was there was I yeah, I kind of halfheartedly did because I was still prideful.

00:28:42:23 - 00:28:58:17
Nick Kennedy
Like, do I really need a coach or I need a coach? Right? But like, there was also like every time I came across someone, I was like, they haven't done Jack, How am I going to like, I don't trust them. I don't trust them. They seem like they. And so I had some friends. We were together on a ski trip and one of they're all very strong people.

00:28:58:17 - 00:29:21:19
Nick Kennedy
And they said, Hey, where's who's coaching you? And I said, Well, and he goes, And one of the guys says, What? You can't find anybody good enough for you? And I started chuckling. He goes, Yeah, I get it. Like, Cause he's the same personality. And they all kind of they I said, Yeah, I need help around this. And they are we since we spend time together and kind of brainstormed about someone and they all agreed like there was this one person, this man that we all know, and they were like, He's a guy.

00:29:21:21 - 00:29:39:17
Nick Kennedy
And I called him up and he said, Yeah, I'd be like, Let's do this right. But like even me as a coach, he was like, You've got to have a coach is hard for me to go hire a coach, partly because I just am not going to, first of all, coaching, to be clear, like it's like real estate agents like it, the bar to bar to call yourself a coach is so low.

00:29:39:17 - 00:30:05:12
Nick Kennedy
I mean, everybody calls themselves coaches and I'm desperately please help me rebrand. I need a different word because I'm just I hate calling myself a coach compared to a lot of people that call themselves coaches. My pride again. But if you look at the coaching revenue, I think I saw something recently and they said like the top three or 5% of all coaches generate like 85% of all revenue and the majority of coaches make below minimum wage.

00:30:05:17 - 00:30:25:16
Nick Kennedy
At the end of the day, when you look at their actual work, but you've got a ton of people that are right around there but might have a good website or might have, you know, or so it's a hard it's on its face but yeah you set up the antidote to all that is have a regular cadence of people who you've given them authority and have the courage to challenge.

00:30:25:16 - 00:30:47:09
Nick Kennedy
You have the audacity. A challenging audacity is a bad word for a lot of people. You know, we usually use it and they had the audacity to do that. Man Audacity is another form of courage. And all courage is, is, is what you come to when you're when you move past fear. Fear doesn't cease to exist when you when you when you get to courage, it's what you get to when you move past fear.

00:30:47:09 - 00:31:06:07
Nick Kennedy
And that's what audacity is. It's like, man, all these things, bad things can happen, but if you have nothing to lose, you're going to go ask the question to the person that you had no business. Ask it out. You're going to go to the play because what else are you going to do? Right? And then that becomes that sometimes turns into really great things.

00:31:06:07 - 00:31:28:11
Nick Kennedy
So my encouragement is like, Man, don't be down if you don't have a life you like, you were given was not the like you want. Have the audacity to go create a new life for yourself. Make people think you're crazy by doing things that people would never do. And and because why? Because people are drawn to that. People want to be like, You're the guy who did what.

00:31:28:13 - 00:31:33:00
Nick Kennedy
Tell me more about that. I like what? Even if it's like.

00:31:33:00 - 00:31:33:23
Jason Croft
The.

00:31:34:01 - 00:31:53:16
Nick Kennedy
And that's the thing that people want to be drawn to. And then you have an opportunity to have a conversation with them about what you're doing.

00:31:53:18 - 00:32:24:07
Jason Croft
Okay, we're yeah, Yeah, yeah, yeah.

00:32:24:09 - 00:32:37:23
Nick Kennedy
Well, I think I think I, I don't know if I told the story in the 78 varsity challenge or not, but I remember my first job at EADS right after I started EADS to stay at a new CEO that came in there. And it was, you know, his first thing you want to do was fire a bunch of people.

00:32:38:01 - 00:32:54:13
Nick Kennedy
And I think I misheard my boss. But during one of our management meetings or one of our meetings, I was a manager. I thought he I heard him say, hey, there's going to be an early morning meeting next Wednesday. You know, 7 a.m. at this room. And I thought we were all invited to come to this meeting. So I showed up dutifully.

00:32:54:13 - 00:33:10:23
Nick Kennedy
I was going to meet and I showed up at 7 a.m. in this room, and I looked around and none of my colleagues were there. It was my boss and all of his bosses. And he looked at me like, What are you doing here and there? And he was like, Who is this guy? And I just sat there.

00:33:11:01 - 00:33:12:08
Jason Croft
And I and I literally.

00:33:12:08 - 00:33:29:17
Nick Kennedy
Was not invited. I later on figured out I wasn't invited to this meeting, but the meeting, Jason, the meeting was about not specific names, but it was about who are we going to let go in this organization? Like by what percentage of the people were going like up? I mean, I'm brand new, like I'm fresh out of college and I'm sitting in this meeting about letting go people.

00:33:29:19 - 00:33:40:19
Nick Kennedy
And I swear to you, Jason, had I not shown up for that meeting, had I not had the audacity or stupidity, I don't know how you look at it. In that particular case, I think I would have been one of the first to go because no one knew I was I was one of the first hires like, well, I didn't do any.

00:33:40:19 - 00:33:54:05
Nick Kennedy
I was not right. I promise I was not providing the value of the salary they were paying me at that point in time. But I showed up and guess what? My boss walked out and he's like, he wanted to compare notes with me and he asked me about a couple clarifying questions. And then he started calling me into his office to talk about him things.

00:33:54:10 - 00:34:22:05
Nick Kennedy
And then I got called into his boss's office to talk about other things. And like before he knew it, I did all these meetings and I just happened to show up in the room. And and and I realized that, you know, I had the opportunity. I've got I count several billionaires as friends and as clients. And I'm telling you, these people who are the masters of the universe, man, they all deal with the same stuff and they're invited to the room because of their net worth.

00:34:22:05 - 00:34:38:16
Nick Kennedy
But at the end of the day, they're like, okay, so how should I frame this conversation with Jamie Dimon? Ask, How should I have this conversation with Elon Musk? Or how should I write? Like to still like going back to their sixth grade moment in which that girl said, No, I don't want to be your you know, no, I don't want to be your go steady with you.

00:34:38:16 - 00:34:54:16
Nick Kennedy
Right. That's still plaguing them. It sounds silly, but it is. He sees these marks in their lives. And and so the whole idea of being in the room is like, if you want to be in the room, you belong in the room. And the invitation is for me to invite you to the room with someone who's in the room.

00:34:54:16 - 00:35:11:07
Nick Kennedy
Now. But like, you really don't need an invitation. You bring your own invitation because there's nobody, nobody who gets in that room. There are some people who get invited, but the majority of people in that room show up in that room unannounced, uninvited. And guess what? Everybody else in the room is almost too feckless to kick you out.

00:35:11:08 - 00:35:25:13
Nick Kennedy
And and that's the that's the that's what you have to do when you plant a flag and you go, this is what I'm going to go do. People are like, man, I'm going to get my popcorn ready because he or she is going to pull that off or he's going to fail miserably. But I'm going to be here to watch it.

00:35:25:14 - 00:35:40:07
Nick Kennedy
And then it's great because and then has to be great because you have to be successful. I did an Ironman triathlon years ago, many pounds ago, and it's like I just remember I had a particular voice person in my head. He's like, You're never going to finish that. And honestly, had he not said that to me, I probably wouldn't have finished it.

00:35:40:10 - 00:35:56:12
Nick Kennedy
But I was like, Damn it, I'm going to finish it because I'm not going to let that guy tell me. I'm not going to finish this. And I hurt myself getting across the finish line, right? Like you belong in the room. This is my invitation to you as someone who's in the room to come into the room, because that's where decisions are made.

00:35:56:13 - 00:37:00:02
Nick Kennedy
And you can get in there and be part of the dialog. Yeah, yeah. I mean, we talk about it in that actually challenge, this idea that to live a fully integrated life, your calling, which is the highest level of framework of your life, has to match, is what you do on a daily basis. There's your calling is your strategy, there's your planning that are tactics.

00:37:00:02 - 00:37:14:06
Nick Kennedy
There's all these things that go into like, what do I do on a random Tuesday morning? Well, my calling in my life is to create experiences to lead a truth telling, a life change for billionaires and prisoners and everyone in between. So that's kind of this big like, wow, how do you how do you even go about doing that?

00:37:14:06 - 00:37:28:23
Nick Kennedy
Well, it means when I don't want to get out of bed, I get out of bed because I'm going to write, because I when I when I write, I know what I think. I don't know what I think until I actually write it out. Right? It clarifies it for me. Why does End Point for me? Because I've got big meetings coming up and I need to help provide good advice to people.

00:37:28:23 - 00:37:43:04
Nick Kennedy
So I need to clarify what I think so I can be clear with them about where I think they should go do because it's what they're paying me to do. Right. So that leads across the board. Well, it's the tack to back then. So I publish a newsletter regularly, so I am planning on I continue to build these courses, right?

00:37:43:04 - 00:37:57:20
Nick Kennedy
I'm like, There are these things I do to get better and better and better. That serves a higher purpose that I can drive down to on a daily basis. It's never about you. It's never about you. It's about something higher, it's something bigger, it's something better. And there's a combination of your God given talents and your and your story.

00:37:57:20 - 00:38:12:23
Nick Kennedy
And I believe every single day of ours was numbered. I believe before you were born and I was born, I, God knew that we'd be having this. I would be on your podcast on this day on on March 21st. Right. I, I believe that. And if that's true, then every one of your days matters. There wasn't a mistake.

00:38:13:04 - 00:38:31:14
Nick Kennedy
Not one of the days of mistake. It's a story that goes along with that. I have credibility because I've spent hundreds of hours in private planes. I've spent hundreds of hours in a prison visiting room. I can talk to a an athlete who grew up in the hood, but also flies around in private planes. I talk to a billionaire who's never known anything but private planes.

00:38:31:14 - 00:38:48:01
Nick Kennedy
Right. I can talk to kids who are like, I have no hope to. My friends died last year and gang shootings and I don't know what to go do. Right. I have this. That's my story. I hated it for a long period of time. I hated it. I was embarrassed by it. I had shame about it. And now I'm like, this is amazing because I get this.

00:38:48:03 - 00:39:07:18
Nick Kennedy
I have this credibility to be able to have these conversations and sit in these moments where I create experiences and sacred moments that hopefully lead to life change for people. And how did I come about this? Jason I had a guy in my life named Richard Hoffman, who's no longer with us, God rest his soul. And he he died of pancreatic cancer.

00:39:07:18 - 00:39:23:12
Nick Kennedy
And as he's as I was sitting with him right before he passed away, I said, how can I ever thank you for metaphorically punching me in the face? He was abused. He's audacious like I am. And he slapped me around a few times and said, You better get your shit together, because if you don't, it's going to be hell.

00:39:23:12 - 00:39:37:18
Nick Kennedy
Let me tell you. Let me point to my life and tell you what happens when you don't get it together. And I said, How can I ever thank you? And he said, Man, just go. Just go do it. Go do the same thing for other people. And, and, and it was like he gave me my calling in some respects to go do that.

00:39:37:20 - 00:39:58:02
Nick Kennedy
And and we all have these moments or we should be looking for these moments with these people that know us and see us because we've asked for help, because we've shown them ourselves, because we've become vulnerable, that they can then say, Hey, Jason. Hey, Nick. Hey, Lisa. Hey, Sam. This is what I see in you. This is where I think might be something to go work on.

00:39:58:02 - 00:40:49:01
Nick Kennedy
And then, man, you never work for a day in your life. And no matter what you get paid, it's exactly what you should get paid. Because that's a calling, not a job. That's a vocation not a career. That's much better than anything else you can be doing, you know? So I my my practice is so I limit my practice severely about who I spend time with.

00:40:49:01 - 00:41:10:21
Nick Kennedy
Just because I being a coach is incredibly inefficient because humans are inefficient. And I'm like, I love that, but there's no way to scale and I don't. I have zero desire to create a bunch of Nick Kennedy certified coaches. Like I just think don't get that model works very well. I don't think anybody has shown it can work very well and so I limit my my practice pretty severely about who I work with in person.

00:41:10:23 - 00:41:29:04
Nick Kennedy
I do one or two things. I either work with people one on one, or I do a group coaching session where I take ten leaders through a 12 month called the Kennedy Leadership Program. And we meet in Dallas and we meet once a month for a full day. And that's a super cool experience because normally you get time with me, but you get more importantly time with nine other CEOs.

00:41:29:06 - 00:41:50:11
Nick Kennedy
Tip of the spear leader. So I limit my practice to tip of the spear leaders, which are they're the people who are responsible for payroll because it's a whole different world moving from a VP or senior VP or even CEO or CFO to CEO. It's just a whole different world. You know, anybody who's ever had to deal with the day to day really hard stuff, it's a different one.

00:41:50:11 - 00:42:05:19
Nick Kennedy
So I spend time with those folks and then my goal is to take all the same information that I share. One on one, I charge a lot of money for 1 to 1 coach and charge a lot of money for my group coaching. My goal is to take that same information and make it available to be in my newsletter and via these courses for free.

00:42:05:21 - 00:42:36:14
Nick Kennedy
So the idea is go consume the stuff as much as you can. And my my preferred hope is that you become so successful through learning some of these things that we get to work together in the future. And when I, when I first opened my practice, Jason, my wife and I spent about three weeks just praying over a list of people, Hey, here's someone I think he's put on the list, came up with like 30 names and I call all of them like 15 of them said yes and was crazy like and over the course of a week, like 15 of them said, say yes, let's do it.

00:42:36:14 - 00:42:55:02
Nick Kennedy
And and now it's it's all referral based. It's great because people will call me and say, Hey, so-and-so said, I need to talk to you about something. And so if you're looking for a coach, like go find a coach, I'm happy to chat with you and either one of those group coaching or one on one coaching. I've got a waitlist for both of them, but let's Shachtman and and figure it out.

00:42:55:03 - 00:43:14:06
Nick Kennedy
Not not I've got a ton of free stuff I've got a great newsletter of a that that I love that Jason doesn't like the name of the zippy turtle and and it's a contradiction of it's a contradiction of terms and memorable and then I write a lot of stuff in and I create these courses as well at Nick Kennedy Coaching Scholars.

00:43:14:06 - 00:43:31:08
Nick Kennedy
Or you can find all that information. Oh yeah, I wrote a book to.

00:43:31:10 - 00:43:32:06
Jason Croft
A.

00:43:32:08 - 00:43:46:01
Nick Kennedy
I wrote a book as well. The Good Entrepreneur. That's a great that, hey, there's better written books, but it's a good book. I'm proud of it. I spent a lot of time on that and I wrote it. I didn't have a ghostwriter. Like, everything I write is mine. Like, I don't. I don't. No one writes for me. I write it myself, which is sometimes bad for some people.

00:43:46:01 - 00:44:03:10
Nick Kennedy
But it but it's like the truth. It's like the true experience. And it's about how to go build businesses, but it's also about the emotional effect it takes on you as you're building the business. And each one of these, every time I work with a client or even at the end of my chapters, I'm always giving homework because I don't want you just to read it and walk away or listen and walk away.

00:44:03:10 - 00:44:20:12
Nick Kennedy
What I want you to do is listen and then have a task that you can give yourself that I'll give you that will ingrain that in you, because that gets to a deeper level. And so the book has 12 chapters, 12 principles, and each one there's a there's a some homework for you to do, and I'll give you fair warning.

00:44:20:12 - 00:44:39:05
Nick Kennedy
One of them is go write your own obituary like I don't mess around. There's no patty cake around here. Like it's like the real deal, because I just I like who knows when I'm going to die, right? And I just. I don't want to spend one day, just not given everything I have. But there are hard things and this is what you have to do if you want to be a great leader.

00:44:39:05 - 00:44:55:04
Nick Kennedy
In my opinion. Jason, thank you and thank you for for helping to address the challenge. You made it so much better. In fact, I don't think I would have done anything if you hadn't been involved. So thank you very much.

00:44:55:04 - 00:45:00:06
Nick Kennedy
Go hire, Jason, everyone. He's great at what he does.

00:45:00:06 - 00:45:06:05
Jason Croft
We'll see you all next time.

 

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Nick Kennedy

Entrepreneur/Author/Business Coach

Take Nick's Audacity Challenge: https://www.nickkennedycoaching.com/audacity

Nick Kennedy is a serial entrepreneur and an executive life coach with over twenty 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. By its acquisition by Surf Air in 2017, RISE had served thousands of travelers with private flying services.

Prior to RISE, Nick began his career as a business development manager for EDS. After serving He then to building multiple healthcare-centered businesses, including Galvanon (acquired by NCR), Global Health Grid and eviti, Inc. (both acquired by NantHealth, Inc. Now as a coach for high-power executives with over four thousand hours of experience, he helps stuck executives become fully integrated spouses, parents, and business people.

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 and three kids. Learn more at www.nickkennedycoaching.com.

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