Popular notions aside, most startups aren't founded by twenty-something year-old college dropouts. According to the Kaufman Foundation, only 24 percent of new entrepreneurs fall between the ages of twenty and thirty-four. 

That means the average entrepreneur must make a major change, both professionally and personally, in order to start a business -- leaving behind the relative security of skills, experience, and connections to start all over again. 

Clearly that's not easy. But it can be done.

One example that might surprise you: Jeff Gordon.

Think of Jeff and you probably think of his four NASCAR championships and his 93 career wins (the most in the sport's modern era.)

But he also owns a Chevrolet dealership and a winery, is an equity owner and executive at Hendrick Motorsports, founded a charitable foundation... and when he retired from driving, became a race analyst for NASCAR on FOX. (You can see him during Sunday's Daytona 500.) 

So yeah: He knows a little about launching successful businesses, achieving success in a variety of pursuits... and about taking risks and starting all over again. (And as for the idea that he can do five things better than I can do one... it's probably more like fifty.)

You retired as a driver and rolled right into the NASCAR on FOX booth, of the top jobs in race broadcasting. Pulling off that kind of transition have been the culmination of a long-term master plan.

You're giving me way too much credit. (Laughs.)

It was and it wasn't. In a way, preparing to be a broadcaster does go all the way back to when I was a kid racing quarter-midgets, etc. My stepfather, John Bickford, recognized that getting me in front of a camera and getting some publicity could help us get sponsors and maybe introduce me to the next levels of racing. 

I was shy, though, and wasn't good at speaking on camera, but enough opportunities came along that I started to get more comfortable.

And he was right: That exposure helped me get to NASCAR. By then I definitely knew how important sponsors are, how important it is to be able to speak to customers, fans, businesspeople -- on camera or off camera -- and all that experience helped me get even more comfortable doing TV. 

When did your thinking shift from "This is fun" to "This could be another career for me"? When you started doing things like guest hosting Live! with Kelly Ripa?

A few years before I retired from driving, I knew approximately when that time would come. And TV was a big part of what I wanted to pursue. I thought it would be a fun challenge --and I was right. Luckily the timing worked out for me.

I'd like to say it was part of a grand plan but Live was an opportunity that came my way.  I had been on several times as a guest and became friends with Art Moore, the producer. He's a big NASCAR fan. When there were guest host openings my name was somehow on the list and was able to do it -- and I had a blast. I enjoyed doing live TV.

Plus, they put it together so well that you can't help but feel comfortable... if you can carry a conversation in front of an audience, you can do well on that show. The team is that good.

Ultimately I was just grabbing a good opportunity: A chance to learn, to build a skill, to enjoy a different experience, to get my name and face out there more, to have fun... when you can get all that from an opportunity, it doesn't need to be part of a master plan.

The skill side is a critical piece. Lots of people want to explore new interests and even careers, but gaining the new skills required is really hard.

That's definitely true for me, too. There are certain aspects of a broadcast I have to work harder on. There are segments we do before the race and after the race that I have to put a lot of effort into in order to do well.

When the green flag drops, my experience from behind the wheel makes me feel really comfortable about what I'm seeing and doing. While that part is easier, what's hard is maintaining that edge after you're no longer driving and a constant presence in the garage area. 

That's where I need to rely on my connections, and to constantly communicate with drivers and teams, so I can stay on top of a sport that is constantly changing.

You wear a number of hats: broadcaster, car dealership owner, race team owner, wine entrepreneur, charitable foundation, family... How do you balance your time?

I do get to wear a lot of different hats, and it's fun. I get to see the sport from different perspective and that helps me do a better job at every level.

At the team owner council meetings, I get to see what NASCAR is doing to help the sport. That helps me do a better job as an equity owner at Hendrick Motorsports. That helps me do a better job with my partnerships with companies like Axalta and Pepsi. All those things give me knowledge about the sport that helps me as a broadcaster.

Everything works together to help me be better.

But you're right, the toughest thing is finding a balance. In January I start focusing on getting ready for TV. February through June I'm far more focused on TV and less on the HMS side -- even though I still want to be involved when important things are happening.  

Like last year when Dale announced he was retiring: We had seats to fill, sponsorships to fill, two new drivers coming in... more of my time was needed.

So I put in the extra time.

Speaking of extra time: Why wine?

Me being in the wine business makes better sense than you're implying. (Laughs.)

That all started from after I won my first championship in 1995. I was in Europe and wanted to celebrate the championship, so I went out to dinner and ordered an expensive bottle of wine. I took a sip and thought, "Okay, so this is how it's possible for wine to taste." 

At the time, Ron Miller worked in marketing for DuPont Performance Coatings (now Axalta) and he and I were pretty close. He said, "You should do your own wine. I'll set you up with some wine makers and help you distribute it." 

It was never a dream to turn into a big business; it was more of a passion that turned into a great business -- and a great branding opportunity.

For a long time I was thought of as a California guy who came from open wheel and had success in NASCAR. In some ways that made things tougher, but it also helped give me a bit of separation from the typical NASCAR driver... which led to some unique opportunities.

What could have been a barrier actually turned out to be an advantage when I wanted to branch out into other things. 

That also sounds like you had a plan.

No, that's just the race car driver in me. Drivers seize opportunities. You try to win races and figure out where that can take you: Win a race and you hope to get a call from someone who wants to sponsor you. Or wants to put you in a better car, or in a higher-level series. 

That's basically the way my businesses have worked. There are certain times we pursue opportunities, but most of the time opportunities come from people who reach out and say, "What do you think about this...?"

Starting your foundation was purposeful, though.

Later, yes, but not at first. 

When I first came to North Carolina, the team said it would be great if I visited some of the kids at Brenner Children's Hospital. I had no idea what I could do to help them... so I brought some autograph cards and walked in the room feeling totally out of place. Then I saw the reaction to my racing suit, to the race car photos I handed out... for a few minutes it seemed to take their minds off what they were going through.

That led me to do more things along those lines, and when I got the Cup level I saw drivers like Bill Elliott, Richard Petty, and Dale Earnhardt doing great things for charity. I realized beyond driving a car and looking after my sponsors, it was my responsibility to give back. 

I've been very fortunate and that means I need to do more for the sport... and also for the community and those in need.

As for the focus on pediatric cancer, my then-crew chief Ray Evernham's son was diagnosed with leukemia, I had met a number of Make a Wish kids who had cancer... I just decided I wanted to help do something about it.

Many people who change careers find that they miss their "old" careers to some degree. I saw you in the media center at the Rolex 24 and my first thought was, "Does he miss racing?"

Once in a while. When I watch the cars go around I do sometimes think, "Boy, it would be fun to be out there competing..." but driving in the Rolex 24 in 2017 was a great reminder of two things. One, I like driving race cars, but the amount of effort you have to put into it to be successful is a massive. I don't take that for granted and don't want to just get behind the wheel for fun.

In fact, I honestly don't know what it would be like to get behind the wheel for "fun." Every time I got in the car I was pushing myself harder, other people were pushing me... whatever you're doing is never, ever enough. You can never be too fast. If you're fast, you're pushing to get faster.  You can never win enough. Win one championship and you're pushing to win another.

And the sport keeps you humble because you will always lose way more races than you win.

That doesn't mean racing wasn't fun, but I never got behind the wheel just for fun. 

Two... let's be honest. Even a guy like Jimmie Johnson will go through this. One day you realize you're not as competitive as you once were. Is it me? Is it my passion? Is it my desire? Is it my talent, my eyesight, my instincts, my hand-eye coordination, my reflexes...? 

Eventually you know you have to walk away, and if you're lucky, you get to decide the right time to walk away.

It's definitely possible to miss certain aspects of something without wanting to go back to doing it again. (Laughs.)

Then let's look forward. What do you want to do in the future?

I'm in a good position. I know who I am, I know my limitations, and I know the things that inspire me and motivate me to push myself.

I really enjoy TV. It's fun and exciting and challenging, so I might like to do more with TV. I don't know if I want that to get too far removed from racing, though, because racing is what I know the most about.

I also want to see NASCAR reach the level it's capable of reaching. The racing is great. There is tremendous talent on the track, although some of the drivers do need to bring out a little more of their personality. 

So for me it's TV, and the business side of the sport... and maybe a little more focus on speaking. Axalta uses me for leadership conferences, annual meetings, internal groups, big customers... and I've done engagements for companies like PayPal.

I really enjoy those events because racing is a lot like business: You set goals, work as a team, know your strengths and weaknesses, know how to rely on other people, know when to take smart risks and when to be patient...

That's the cool thing about how all of this has come together. Ultimately racing is about making and seizing opportunities, and so is business. A lot of what I learned in racing helps me with TV, helps me with the business of racing and business in general... while I do pursue a variety of things, they actually fit together really well.

Even if I didn't plan it that way. (Laughs.)

Published on: Feb 15, 2018