See Golden State Warriors coach Steve Kerr as an exception to the rule. He won five NBA championships as a player and two as a coach. See Larry Bird, the only person in the history of the NBA to be named Most Valuable Player, Coach of the Year, and Executive of the Year, as an uber exception.

For the most part, history is littered with great athletes who try and fail to become great coaches. The same is true for great athletes who try, and fail, to become successful executives or team owners. The perspective shift required is massive. The skills required are too different.

Leading from the playing field is much different than leading from the locker room or board room. 

Unless you're Tony Stewart

As a driver, Tony won three NASCAR season titles and an IndyCar championship, making him the only driver to win a championship in both series. He's also won multiple driving titles in a number of other racing series. 

As a team owner he's won NASCAR championships -- one as a driver/owner, and one with Kevin Harvick. (And so far this year, Stewart-Haas Racing drivers hold four of the top eleven spots in the NASCAR point standings.) His teams have won more than 20 championships in USAC and World of Outlaws.

He owns Eldora Speedway, is a part owner of Paducah International Raceway and Macon Speedway, and founded TrueSpeed Communications, a marketing and public relations firm. 

Along with just a handful of other athletes, Tony Stewart has successfully bridged the gap between athlete and entrepreneur. 

How? I asked him.

Let's go way back. You're an incredibly successful -- and incredibly busy -- driver. What made you decide you wanted to own a team?

None of it was part of a master plan. That's the thing: Even before I owned my first team, my entire career has been about grabbing opportunities that present themselves.

I can remember thinking, "If I can race sprint cars and midgets for a living, and get paid, and not have to have a 'real job,' that would be awesome." That's all I wanted. And my driving career grew from there.

Then I ran into a buddy, Danny Lasoski, at the Chili Bowl in 2000. He had just lost his ride. He was all bummed out, standing there with his helmet bag in one hand and his seat in the other. On the spur of the moment I said, "If I can put together a team, you won't have to worry about who you'll drive for every year."

He said, "Man, that would be awesome."

And that's how my first team started.

You had been around racing all your life, but how did you figure out how to put together a team?
At that time NASCAR was growing at such a rapid rate that companies were almost begging to be sponsors. And that also applied if you were a NASCAR driver doing something in a different series. The shine of your name was enough. That's what helped us get the sponsorships to start that team. Of course I put some money in, too, but for the most part, sponsorships helped carry the team.

From there I just figured it out. To be honest, it's really not rocket science. You estimate what the cars can bring in during the year, and project what it will cost. Plus Danny had run in the World of Outlaws for quite a while and had a great feel for the financial side, so it was really just saying, "OK, this is literally about dollars and cents. Can we raise enough money to do it?" And we could.

Money is one thing. Building a team is another.

That also wasn't hard. Danny knew exactly who we wanted as a crew chief. The crew chief hired the other two guys that work on the car, and that was it. It was that simple, and that's how we could do it.

Of course there's a huge difference between having three people in your shop to having 300 people in your shop.

That raises a good point. How did you decide you wanted to make the leap from owning one small team to owning multiple larger teams?

Again, I didn't plan that out. Mopar was our engine supplier at the time for the sprint car. We won a championship with Mopar and they said, "Would you be interested in putting together a youth program?" They wanted to do a Silver Crown and sprint car. 

So we did that the first year, and then they wanted to add a midget program.

In terms of personnel it didn't require a much bigger operation, but in terms of cars it was a big commitment: We had Silver Crown cars, pavement, dirt, sprint cars, midgets... there were a lot of cars in the race shop.

Again, it came down to, "Can we make number A match number B?" 

Looking back, it was a great way to learn how to build a racing organization. But it wasn't part of some master plan. We just reacted to opportunities that came our way.

Buying Eldora Speedway was another opportunity that you didn't go looking for; it came to you.
Earl Baltes built Eldora in 1954. He had been the only owner since day one. He asked me to come to his house, and when I got there he said, "My health isn't great, and Berneice (Earl's wife) and I think you're the right guy to take over the speedway."

So we went back about a week later, met with Earl and started looking at the numbers to see if we could make it work. 

So it's like a tree: It starts here, then something branches off, and that branches off, and suddenly you have this big awesome mess.

(Laughs.) I wouldn't put it quite like that, but OK.

We get opportunities presented to us all the time. But opportunities pop up for everyone. Maybe the difference is I don't have that risk averse gene that automatically makes me think, "Oh, I can't," or, "Oh, that will never work."  

But there are two major advantages I also have going for me: Eddie Jarvis, my business manager, and Brett Frood (the President of Stewart-Haas Racing who also oversees True Speed Enterprises, the company under which all of Tony's business interests fall). Eddie and Brett and I make up three sides of a triangle.

Say someone has an opportunity they think is right for us. Brett looks at it from the business side. I consider the financial investment. Eddie considers whether it's right for our brand. Of course those roles overlap as well, but that triangle lets us look at every opportunity from three different perspectives.

And since we all trust each other, we have a policy that the three of us all have to agree, or we don't do it.

Of course that means there have been a lot of projects I thought were awesome, and Eddie was on board, and Brett didn't think it made good financial sense. Or Brett and I loved a project, and Eddie felt it wasn't right for our brand. 

That means even though you're the owner, you have to step back and be OK with other people overriding your opinion. 

Absolutely. But I can confidently say I don't think we've made too many bad decisions. So I feel like the system works. We have people that I know have my back, and that know I have their backs, and by now we have a really good sense of what works for us and what doesn't.  

It's basically proof that we're all on the same page. Like at Stewart-Haas, when we switched from Chevrolet to Ford. The three of us just sat down and said, "Does this make sense?" And we decided that even though it was going to be a massive undertaking for our folks, we felt it did.

Did you intuitively know that creating a decision-making triangle was the right thing for you, or...?

I didn't go to college. I went racing. I don't have a business background. I didn't even take any business classes in high school.

But I did drive for some really smart people that were good in business and in professional sports, and if you're smart enough to shut your mouth and listen, you can learn a lot.

I was in my second year of driving for Joe Gibbs when I decided to start the World of Outlaws team. I learned an incredible amount in a very short amount of time from hanging around that man.

Probably the biggest thing I learned from Joe -- and really the most valuable thing anyone in my position can learn -- is that I don't have to know how to run everything. I just have to know how to hire the right people to make the right decisions.

What do you look for in people? 

Clearly, skills are a given. But there's more involved.

Take Brett. He's a Harvard Business School guy who also loves sports. But I was also comfortable with him from the very first day we met. He's a huge asset to me and to our organization. 

Once you get people like Brett and Eddie on board, then that three-person system helps you choose more great people. 

It all starts with building that foundation. Then you can take advantage of each other's opinions about the key people you hire. We don't always agree initially, but by the end of our conversation, we do. 

The best part about building a strong foundation is that it creates a multiplier: Every year your organizations can get better because the strength of your foundation keeps growing as you keep adding great people.

That probably means that sometimes you don't even run an idea by the other two because you know what they'll say.

(Laughs.) Absolutely. There are opportunities that don't get to me anymore. There are opportunities that get presented to me that I don't take any farther. I'll think, "I want to do this, but I know Brett won't."

But sometimes I will say, "I'm only bringing this up because I really like the idea of it. I'm pretty certain it doesn't make sense. I just want you to validate what I'm thinking."

And sometimes they'll say, "That's actually not as bad an idea as you think." And we'll move forward.

But what it really comes down to is that we're open and honest with each other. If we don't like an idea, we explain why. We talk about it. We don't hold back.

That's incredibly important if you want to build a strong team.

A lot of people start businesses because they love something, but soon they find that a very small percentage of their day is spent doing the thing they love. 

That definitely happened to me. At first being an owner/driver sounded like a lot of fun. But I had to focus on driving my car, then get out and worry about our other cars. It was extremely hard to do everything I needed to do.

That was one of the factors that led to me getting out of a Cup car. The level of competition is so high that it's really not possible. 

Forgive me for playing armchair psychologist, but when I came in, someone had just asked you how many championships your various teams had won and you didn't know the answer. To me, that means you're more focused on the success of your people than on your own success.

Trophies are fun, but the cool part of winning a championship is doing it with the people you work with. When you do it as a group, alongside people you enjoy working with, the satisfaction of being part of a team and sharing the good times and the bad times is something I've always enjoyed.

So as an owner, seeing the team win -- seeing that group of people win -- that's really cool. That's why I keep doing this. Of course you have to make the dollars work, but getting to see people enjoy success? That's the real fun of this business.

The very first race we won as Stewart-Haas was an all-star race. Gene Haas (co-owner of Stewart-Haas racing) was there. To get him his first Cup win, to get the team that had worked on his race team for all those years their first win...

I know how much I like winning (laughs) and what surprised me was seeing grown men cry that had never been in Victory Lane before. That meant more to me than winning the race.

Forget the trophy. Forget the money. Seeing how they felt? That was awesome.

With all your different business ventures, how do you manage your time?

I don't manage my time. Someone else manages my time. (Laughs.)

Seriously, though, it just depends on where I am. I'm still racing sprint cars. This year I'm going to shoot for running between 90 and 100 races. Sounds like a big number, but it's realistic.

That's because we have really good people in the right places. Roger Slack runs Eldora. We're just a phone call away from each other. Same with Brett at Stewart-Haas. Same with Kenny Schrader; he and I co-own two tracks. Same with all the other folks. When I want to know what's going on, I call them. When they want to know what's going on, they call me. 

It really is that simple. A lot of people put systems in place that make it more complicated than it needs to be.

Many aspiring entrepreneurs hesitate because they're concerned about risk. How do you deal with risk?

Some of my friends have small businesses and it scares them to death to do anything. They're afraid to make decisions. They're definitely afraid to make big decisions. They're afraid of change. They're scared to get outside the box. My whole life has been outside the box.

So I'm used to risk. Risk doesn't scare me, especially since I have two other guys to bounce ideas off of. 

But keep in mind, we work really hard to evaluate risks. We look at every angle of every major decision and every opportunity. We've very patient.

Plus, what's the worst that can happen? If it doesn't work, you do something else. For a lot of people, their ego is tied up in there as well.

I don't care about the ego side. When I am driving a car, sure, I have an ego. (Laughs.)

But on the business side, having people come to Eldora and say, "We really love what you've done here. Keep up the good work." That's the part I love.

It's not about ego. It's the validation of all the work you put in. It's the gratification of seeing other people enjoy what you do, and seeing other people succeed.

Published on: Apr 26, 2018
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