I didn’t finish them the first time. I failed twice in my pursuit of seeing if I could run 100 miles. I learned so many different lessons along the way that I’m now able to take from that experience of running 100 miles. It helped me become a better coach, a better podcaster, a better husband and father, a better person in life, and a leader. 

2020 is again, a great example of just when you think life is going great. You thought that things are going to stay that way forever. You’re kind of done getting through those pitfalls. 2020 slapped us pretty hard instead. I said, “Hey, hold on a second.” It changed in an instant. 

Those that have a 100 mile mindset are going to be able to navigate those times and those waters much more efficiently and effectively. You can come out on top through those times. Those times are pretty much guaranteed to happen.

I think the moment we can know that and realize it, then you can plan for it and just expect it. You can expect 2020 to happen. When it does, you can be ready for it. It doesn’t mean that you’re excited that it happened, but you’re equipped to be able to get through it.

The 100-mile mindset was me just taking those experiences and putting them into the book. I’m hoping that someone will read it, and help them inside of their life.

Sean Murray  3:23  

I love this concept of “The 100 Mile Mindset.” I think you’re absolutely right. There’s going to be events in our lives that are going to throw up huge challenges. It’s going to feel like the 100 mile, 24 hour run. If we’re ready for them, we’re going to be that much better prepared.

Talk a little bit about the first few times. I don’t know how many times you tried before you completed it. What was it that sort of prevented you from achieving the 100 miles at first? And then, what got you there eventually?

Nate Bailey  3:55  

Just a little bit of a timeline. I decided in March 2018. I said, “I wonder if I can run 100 miles.” I signed up for a race three months away. I give myself a lot of time to prepare. I wasn’t coming from a background such as putting in lots of miles. I was kind of coming off the couch.

I was taking care of myself. I was working out but I was not running consistently. I technically ran a marathon in 2008 as part of an Iron Man. But I wouldn’t call what I did to finish that Iron Man, running. 

The first one was the Kettle Moraine 100 in Wisconsin. That was in June of 2018. The biggest thing that kept me from finishing that was lack of preparation. I’ve only given myself three months, so there’s only so much preparation I can do. I was preparing. I was running but I just hadn’t had enough time to really prepare the way I needed to. 

There was a piece of the lack of preparation. The details matter. I missed the cut-off. That’s how I kicked off the course in that first experience. I made it 100k, which is about 62 miles. I needed to get to that checkpoint by 18 hours. I got there at 18:10.

We didn’t realize that we missed the cut off. I took a little bit of time. I changed some clothes. It just rained. At about 18 hours and 30 minutes, I was there for about 20 minutes. We took off. We attempted to take off and keep going. I was feeling okay, which was reasonable after going 62 miles. I was feeling good. I was going to continue. 

I’ll finish and yell out my number like, “Hey 65. Where the heck are you? What are you doing?” I’m like, “What are you talking about?” [Someone said], “You missed the cut-off.” I’m like, “No way.” 

We thought we had time. We were kind of doing the math. If we stay on this pace, we’ll be alright. The cut-off times weren’t a secret. They were in the race packet. Again, it was my responsibility as the runner to know what those were. I didn’t. 

And so again, I wasn’t prepared. I did not only from a physical standpoint, but from the mental or just a preparation piece of it. That was one. And then, the second one was the burning river in July. About a month and a half later, I’m going to go do this thing. I’m committed. I’m going to hit this. I’m going to finish it. I went all by myself. 

Most people have a team of people that will support them. The first one, I had four people there that kind of helped me at the checkpoints and helped me along the way. It was pacers. 

This one, I went by myself. I made it about 75.6 miles this time. I improved, but I just kind of got to the point where I was moving so slow that there’s no way I was going to finish. 

Again, there’s this cut-off time. You got to stay at a certain pace to keep going. The biggest one for me, and what I really learned, there’s so many. I don’t listen to the book or read it. When your emotions are high, like they were at that moment when I decided that, “Hey, I can’t go anymore. I’m done for the day.” 

There’s a lot that goes into those decisions. There’s a lot of conversations you have with yourself and your head around that. When your emotions are high and the clarity is low, just don’t make decisions in those moments.

At that moment, it’s like, “Why am I doing this? What am I doing this for?” 75 miles is awesome. “Hey, it’s not 100, but it’s way more than anyone else. You don’t need to keep doing this.” That’s the conversations I was having with myself. 

Clarity was low. I was just thinking about the pain. I was thinking about not having to do this again. Leaving, traveling, and everything that’s around that. I knew not to make a decision. I would never attempt this again, and to give myself a little time so that the emotions can kind of settle down a little bit. 

I can be a little bit more clear about what it is that I really truly wanted. I was sick of being a person in my life where I would say it was going to go do something. Maybe go three quarters of the way. It’s kind of like playing football. You don’t take to the one yard line and then take a knee. You put it in the end zone. 

I know the power of if you are your word, you stick to the things that you’re committed to, that overflows to everything you do. It becomes very powerful when people start to see you. Now you ask that person, “Hey, Nate says he’s going to do something.” 

They just know before it happens that it’s going to happen. It’s really powerful. I was kind of done being the guy who said that he was going to do something and then not following through. 

On the third attempt, it was Pony Express 100 in Utah in October of that year. It was about all over the time span of about seven months. I completed 100 miles. All of that culminated into the book.

Sean Murray  8:22  

Wow, that’s a great journey. Listeners know that I run, I’ve talked about it on the podcast. It’s a time of reflection. It’s a great way for me personally to get exercise. I feel at one when I’m running. But I’ve never attempted 100 miles or anything close to it. 

What I have read about when people do compete at this level is that athletes that are a little older, I want to say over 35 years old, maybe 40, even into their mid-40s can’t compete, win and beat athletes that are 18 to 24 years old. These are those who are in the peak and prime of their physical life.

I would be interested to hear your thoughts on why that is. If we were going to go out and do the 100-meter sprint, a 45 year old person is not going to win. We know that. But when it comes to 100 miles, they just might, so why? What’s going on there?

Nate Bailey  9:15  

I think there’s a lot of factors in that, but I think you’re right. I’ve heard many very competitive elite ultra runners talk about kind of being in their prime in those mid to late 30s, even into mid-40s. They were kind of at their peak. I think because it is 100 miles, the best of the best are cruising. 

They go on incredibly fast over a long period of time. But just from a physiological standpoint, you’re not sprinting for 100 miles. You’re just not. I think just the ability level that’s required allows you to be able to perform at a high level for an older age period. 

When we come back to the mindset piece of things, I think that’s huge. Somebody who is 18 to 20 years old, or even early 30s, depending on their experiences, may have not developed that mindset yet. They haven’t had a lot of time on this earth to have those experiences, to go through some failures, and to learn how to persevere.

I just had my 44th birthday. I’ve made some poor choices and decisions. I’ve had some hard things happen to me. Luckily, I’ve been able to lean on those, learn from them, and help me when similar situations arise.

When you’re on a 100-mile rise, there’s a lot of conversations going on with yourself. There’s a lot of adversity. There’s a lot of points where it hurts. One way to stop that would be to just ease up or to quit. Somebody that’s seasoned, I guess we’ll say that they’ve been there before. And they know that, “Hey, I just need to push into this and keep going.” 

Having said that, in the ultra world, there are a number of younger folks that are doing really well. But there’s also like you said, there’s a number of people my age that are also continuing to crush it. They’re maybe even having some of the best times I’ve ever had.

Sean Murray  11:03  

When you think about the 100-mile mindset as an analogy to other obstacles in our life, I think you’re absolutely right. The mindset to get to the 100 miles is the most important part. The physical part is not as important as the mindset part. That’s going to be the case in the other challenges we face in life. 

If you can get the mindset right for that challenge, it can help you with other challenges. I think how we talk to ourselves, how we overcome negative thoughts and emotions during times of stress like that is really important. 

Someone with more experience and with that ability to control that mindset, I think has an advantage. In the ultra world, you can see that they might be in a disadvantage physically but the mindset advantage can be overcome. 

Talk a little bit about the work you do with executives and leaders as far as building leadership skills, and especially using kind of physical challenges to help people build up resilience.

Nate Bailey  12:11  

I have a program called “Championship Leadership 24 hour.” It is just a 24-hour physical experience. I have a military background. I really do want to impact and help other executives, business owners, entrepreneurs to become better leaders. Not just in their business, but in all aspects of their life.

I know you get the podcast, The Good Life that we’re talking about right now. It’s all about that, right? I don’t just want to crush it in business, or I don’t want to just crush it in one area of life. I want to have a great life, a life that I’m proud of in all areas. 

In order to do that, first you got to lead yourself in a podcast called “Championship Leadership.” What’s required to become a championship leader? My strongest skill set is in face-to-face experiences like this, where through the physical piece, you’re able to learn so many lessons.

Again, that’s how that book came about. It’s such a great environment to be physically maxed out – stresses of the physical experience, lack of sleep, lack of focus and clarity. All of those things happen in real life in different ways, but we can kind of create that in the physical piece or through the physical evolutions that wear them down. And then, see how they lead in those moments. 

That’s what life is all about. It’s about how do you lead when you’re in adversity. It’s easy to lead when everything’s going well. I talked about Winston Churchill in World War II, and of that time that allowed him to step up as the leader that he was born to be. Had there not been a World War II, those skill sets may not have ever come to be known. 

He was born to lead in those moments. I love the physical piece and experiences. I love how that can help to bring out the best in others, and push them to become championship leaders.

Sean Murray  13:59  

You have a very interesting background. You have a lot of success as a real estate investor. You’ve written about that as well. Talk a little bit about your career.

Nate Bailey  14:10  

I still do invest in real estate. I have some properties across the country. I have properties in multiple states. I’ll continue to do that. I’ll continue to build that. The thing that I love about real estate is the fact that you can have it and build that.

It really can be something that’s on the side. It doesn’t require a lot of time and energy if it’s structured the right way. You have other people to help manage it and take care of it. You get into the right investments. 

That’s always kind of been there. At the same time, I had an insurance brokerage. I own a CrossFit gym. I wouldn’t wake up in the morning and be lit on fire to go build an insurance brokerage. But it did afford me the opportunity to learn a lot of things and to have a lot of experiences. 

I look back and now it all makes sense to me. Sometimes as you go through certain experiences, it doesn’t necessarily make sense why you might be doing something at a certain point in time. And then you look back, and you’re like, “Oh, now it makes sense.”

I always gravitated towards being a leader. I’ve always wanted to be an entrepreneur and a business owner to lead myself and the lifestyle that I really want for myself. I guess I look back on those. There’s just time spent or dues that I had to pay to do what I do today. That’s the best way to explain it.

Sean Murray  15:27  

I like how you describe some of the benefits of real estate investing and giving your time. I think time is something that we seriously undervalue. It’s one of the reasons why if you do financial investing, or just investing in say, the S&P 500. If you do invest in the S&P 500, you’re going to get the market return. 

You can free yourself up from chasing every other stock out there. You can try to get a little bit more advantage over other investors to get that alpha, which is that return above the market. It can take a lot of time. It’s completely reasonable to take a step back and say, “Well, what do I want to do to get a return that’s good enough to afford me to do what I really want to do and light up my passion?” 

I think that’s a great frame to look at that decision. I can see how you applied it and ended up where you did today. Talk a little bit about your podcast and this idea of championship leaders. What are you trying to achieve in the podcast? What is a championship leader?

Nate Bailey  16:24  

“Championship Leadership” and the podcast came as a way to reach other people. A big part of who I want to be is to impact as many people as I can. The podcast is a great way to do that. But also more selfishly, I love bringing people in while having conversations and connecting. 

Selfishly, it’s a great way for me to connect with people like yourself and many other people that I’ve had on the show that I never would have connected with had it not been because of the podcast. 

“Championship Leadership”, the name is actually a good friend of mine, Joe Williams who threw that name out there. At first, I wasn’t sure about that. I love it now, of course. It is different and unique. I think “Championship Leadership” is again, number one. 

You get to lead yourself first before you can lead anyone else. Just having the courage to live the life that you want. You can go and actually make a difference, and not focus on yourself but on others. I think that’s the ultimate.

Sean Murray  17:23  

I always think great leadership shines through in times of adversity when a leader is called to rise above. We’ve had Andrew Roberts on the podcast recently to talk about Winston Churchill, and how he rose to the occasion during World War II. 

We’ve also had Elizabeth Samet talk about Ulysses S. Grant, and how he was able to remain calm under pressure during the Civil War. He never blamed others when things didn’t go his way. How do you define great leadership?

Nate Bailey  17:54  

Great leaders take 100% responsibility when times are tough, or when one that losses are coming. They deflect and give 100% of the accolades in the good times in the winds. They celebrate the team and the individuals that helped get those wins. 

One example would be Jocko Willink, if you’re familiar with him. I think another way of saying extreme ownership is when things don’t go the right way, even if it wasn’t directly your fault, as the leader, you are 100% responsible for everything that happens under your command, if you want to say. 

It’s being willing to be really selfless. There’s a lot of leaders out there that aren’t. They do want the accolades. It’s very clear who those leaders are. It’s very clear who are selflessly putting themselves aside for the benefit of the team. That to me is the championship leaders.

Sean Murray  18:48  

That piece about accountability and taking ownership of when things aren’t going well, or when decisions were made, or when the outcome didn’t work out the way you had hoped, I think that’s one of the more difficult and challenging pieces of leadership. 

For me personally, it’s not fun to be associated with something that’s not working out, or to feel responsible for failures in some way in an organization or as a leader leading a team. Do you have any advice? What do you tell people? How do you help people face up to that and deal with that in a way that lives up to their values of being a championship leader?

Nate Bailey  19:28  

It’s tough. It sucks when things aren’t going right. You’re not on the path or the trajectory that you would like to be. It’s also a part of life. I would just say that in championship leadership, it’s okay to go through those times and experiences. I would almost again say that you’re required to have to go through some of those times and those experiences. 

But really again, it’s in those moments where the championship leaders are made or built. It’s how you are deciding to respond and react in those moments. I can give you a personal experience. 

When I was getting deployed to Kuwait, I was a platoon leader. I got attached to a unit that was not the unit I was a part of. I was in the Wisconsin Army National Guard. And so especially National Guard units get deployed a lot of times. They have a certain amount of slots, but they might not have all of them filled. 

I was attached to this unit. The first day I met everyone was on the first day of deployment. It was a very interesting experience to come into. It was like, “Hey, I’m the leader, but I don’t know any of you guys. You got to follow me.” 

Through that, we went through three months of train up pre-deployment training in Gulfport, Mississippi, or Camp Shelby. It was just outside of Hattiesburg. There was an evolution or an exercise that we did that we trained up for. It was kind of a simulation of what we’d be doing in Koi.

They were simulating probably the worst case scenarios that could happen. That is to see how you would respond. It didn’t go well. I had to eat a ton of crow. Of course, that was a bad reflection on me as a platoon leader. 

It was a defining moment. It is one that shows how you are going to respond. At that moment, it was just to gather everyone around and to own it. It was to take responsibility for that. But also in that moment to be like, “Hey, this will never happen again.” 

We’re going to learn from this. We’re going to move forward. We will be prepared. You can count on me to know that we will not repeat this ever again. It was hard to have that conversation and to own that group of men who were looking at me like, “Well, man. This is our leader. We were doing what we trained. We weren’t prepared. That’s on him.” 

Many of them were probably waiting to see how I was going to respond. I could have just pretended it didn’t happen. I could have not said anything about the experience that I had. The results that we had in our deployment moving forward from that would not have been the same had I not had that conversation, owned up to that, taken in that responsibility, and had that accountability for myself. 

As hard as it really was in that moment to stand in front of those guys, 42 men, and I really just got to know and to own it in that situation.

Sean Murray  22:10  

That’s a powerful story. You turned it into a learning experience. You used it as a kind of a foundation to build on to say, “This isn’t going to happen again. I’ve learned from this. I’m going to move on.” 

If you can make that turn, I think it gives you a little momentum to build on something positive out of those moments, which can be really challenging. You mentioned Winston Churchill earlier. I had Andrew Roberts on the podcast a few episodes ago. He wrote a biography of Churchill called “Walking with Destiny.” 

One of the things that Roberts talked about in learning about Churchill was the many mistakes that he made. He talked about how Churchill learned from each one and turned each setback into something positive. I think that’s something that’s helped me in moments like that to know that it’s part of life. Like you said, it’s part of the human experience. 

No leader becomes a great leader without dealing with setbacks and learning how to deal with setbacks. You just wouldn’t get to where you are. You wouldn’t be a great leader without figuring that one out. This is just my fate and my path to figure it out. I’m taking it head on. That’s a really impactful story.

This has just been a wonderful conversation. Tell my listeners where people can learn more about you, the work that you do, and some of these 100-mile challenges.

Nate Bailey  23:36  

The best place for everything is to go to my website, natebailey.org. You can find all my social media contacts there. You can find out how to get access to my book, and to our 24-hour experience. 

We also have a free Championship Leadership Facebook group for entrepreneurs and business owners. It’s a place for us to come together, do some training, have some expert interviews, and things like that. The natebailey.org is the best spot.

Sean Murray  23:59  

Great. Well, Nate, thanks for being on The Good Life.

Nate Bailey  24:03  

Thank you.

Outro  24:05 

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