Robert Herjavec seems way too busy to be having fun. Not content to settle down with the tens of millions of dollars he made on the sale of his two previous computer-security companies, in 2003 the Toronto-based entrepreneur launched The Herjavec Group Inc., which ranks among Canada’s Fastest-Growing Companies and did sales of $64 million last year. When Herjavec is not playing CEO of a high-pressure business with big-name clients, he’s jousting with such business luminaries as Kevin O’Leary and Mark Cuban for the weeks-long tapings of two TV shows: CBC’s Dragons’ Den and ABC’s Shark Tank. Or writing a followup to his bestselling business book, Driven. Or racing his new Ferrari 458 Challenge car in the Montreal Grand Prix and other high-profile auto-racing events around North America, requiring the same lightning-quick reflexes, intense focus and—ahem—balls as the pros.

But for Herjavec, such exhausting work seems to be its own reward—and it produces many others. PROFIT editor Ian Portsmouth interviewed Herjavec in mid-July, a few days after the pair zipped around the Honda Indy Toronto track at speeds of more than 230 km/h.

How did you get into auto racing?
I started in the mid-1990s, just two or three years before selling BRAK [his first company]. I owned a Ferrari street car. And you realize very quickly there’s a difference between driving fast on the road and really learning to take a machine to its limits. I just wanted to see how it worked.

So, I took my car to the track. The first day I was there, one of the drivers, a guy like me, went around a corner and wrecked his Ferrari. At the time, they were selling for $1 million. Whoa!

A friend of mine told me that you should never race in anything you can’t afford to walk away from. I couldn’t afford to walk away from a Ferrari, so I got into a series called Formula Ford for three years. But from one perspective, racing is three days of standing around for about an hour’s worth of sheer exhilaration. I just didn’t have the time anymore, my kids were little and I had a pretty serious accident.

What made you return this year?
A friend of mine told me Lamborghini was bringing its racing series to North America. I thought of what a fabulous and unique experience I could give my customers. It didn’t work out, but I’d been bitten by the racing bug. I looked into the Ferrari 458 series, and I took the plunge.

You’ve on top of the business world, but you’re Joe Average among Ferrari 458 drivers. Are you racing because you need something new to master?
When I started, my goal was simply not to finish last. I finished in the middle of the pack, and then sixth out of 34 drivers in Toronto. My wife knows me so well. She predicted that I’d take it much more seriously if I had even a glimmer of a hope of becoming one of the top guys. Now, I think I have the ability to close in quickly and get there.

You’re penning another book. What do you hope to achieve with it?
The first book was about getting on the road to business success, with any amount of money. People always say to me that the first million is the hardest. Absolutely. The first million is very hard. But the next few million are even harder in some ways. Because once you’ve achieved that level of comfort, you lose the hunger and raw drive that got you there. The new book is going to explore some of those themes.

So, how do you stay hungry?
People who know me well know that I’ve never really been money-driven. I’ve always been success-driven. It’s about constantly setting new goals and never settling for where you are in life.

How might your life have turned out differently if your father hadn’t tried to escape communism in Yugoslavia and brought you to Canada when you were eight?
I think I would have found my way, no matter what. I’m certainly not the smartest guy or the guy with the best education or anything like that. But I think I’m really good at being dropped into a situation and finding out how the game works and how to get ahead in it.

Being a successful entrepreneur has opened doors to some amazing opportunities, such as auto racing and Dragons’ Den. How important are those things to you?
All of those things are important to me. But when my mom [who died in 2008] had ovarian cancer, it was great to be able to help the hospital and the folks who took care of her. It’s great to be able to give back, and that’s important to me, too. Being a successful entrepreneur allows you to explore all the things that are important to you.

During the Ferrari 458 Challenge weekend in Toronto, you took a very ill teenager on a “hot lap” around the track. What did that experience teach you?
A customer cancelled their hot lap, so I called a friend of mine who works with sick kids. He found a young man battling cancer whose lifelong dream had been to ride in a Ferrari. And I thought, “OK, how cool would it be for him to ride around a racetrack?” He’s 15 years old, his name is Adam and he has been in hospital for something like four years. He came to the track in an ambulance. And he needed to be put into the car very gingerly, because in the middle of his chest he has a big hole where they put in drugs and all kinds of stuff. It’s awful.

As soon as the door closes and everybody leaves, he leans over to me and says, “I just want to go really fast.” And off we went—boom!

How did that make you feel?
Very humbled. And at the end of my time with him, I was on such a high. I felt that I have absolutely freaking nothing to complain about. It taught me that you have to be happy.

His mom and dad were there, and his mom said to me, “I really want to thank you for doing this. We’re huge fans. What’s the key to your success?”

I said, “My key to success is that you just have to keep going. Shit happens in life. You just have to get up the next day and carry on.” And she looks at me and says, “I know.”

I felt an inch high. One day, this woman woke up and her son had cancer. And here I am, telling her how great I am at being resilient. Shame on me. I didn’t mean it that way, and she knew I didn’t mean it that way. But, man, I have to tell you, there’s a whole other level of resilience.

In your public-speaking gigs, you stress the importance of dreaming big. Why?
Our only limitation is what we can imagine. A mind, once expanded, can never return to its original size. I think we can get Herjavec Group to $200 million in sales within the next three or four years. Today, I have the ability to look at that number and it doesn’t scare me; it motivates me. But 15 years ago, I didn’t have the experience to know that it’s achievable.

Do you now apply that philosophy to other parts of your life?
I always think, “Why can’t that be me?” After finishing sixth, I told my wife I can finish first. Not today. Maybe not this year. But I ran with the guys at the front of the pack for a while. And for me, it’s always about that. You feed off every little bit of success until it becomes more and more.

A sticker on your car reads “Ferrari Certified Pre-owned.” You don’t seem like a guy who’d buy a used car.
It means Ferrari-certified pre-owned parts! This is the first year for the Ferrari 458 Challenge car, and there’s no real market for used ones. When I entered the series, a lot of the other guys were thinking, “Here’s a guy with lots of money who probably can’t drive and is going to get bored by this, and then we’ll buy his car cheap.”

But much to their chagrin, they’ve now realized, “He’s probably going to stay with this. And, yes, he can kind of drive. So, we’re not going to get a cheap 458.”

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