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Austin Hill, Montreal. Start-ups: CyberSpace Data Security, consulting, 1993; Infobahn Online Services, Internet service provider, 1994; TotalNet, ISP,1997; Zero-Knowledge Systems, online security, 1997; Synomos, corporate data protection, 2004

Currently: CEO, Akoha, social gaming; chairman, Standout Jobs, online recruiting tools; managing partner, Brudder Ventures, venture capital

Hamnett Hill, Montreal. Start-ups: Pegasus Multimedia, corporate presentation services, 1991; TotalNet, 1994; Zero-Knowledge Systems, 1997

Currently: CEO, RadialPoint, corporate data security, 2003

Hamnett Hill: Radialpoint is one company, but within it there've been at least 30 start-ups. It could be as simple as a new firewall service. We use the same model as starting an entire company: get a small team of entrepreneurial-minded people, come up with a plan, a design, experiment, and then roll it out.

Austin Hill: And to foster entrepreneurial spirit, what you need are two things: ideas and venture capital. There's a gap in Canada for entrepreneurs right now. Silicon Valley, New York, Israel: These are places where it's easy for people to find support. Density is also very important in fostering entrepreneurial spirit. For example, Montreal made a mark on visual effects and graphic arts in the early 1990s with companies like SoftImage, so there was a wave of students who acquired these skills. Now we've seen a recycling of that talent into the video-game industry. The result is that venture capitalists from around the world who are interested in video games will look to invest here. In the Valley, you can't help feeling that density. You might have an idea and decide to go for a cup of coffee. On your way to get that coffee you will run into six people who will help with your idea. In Canada, if you want that type of atmosphere you have to go to a conference. What makes a great entrepreneurial centre is talent, ideas, capital. And battle scars. And swagger. Cojones…

HH: …Cojones. A certain amount of hubris is required to be a successful entrepreneur. It's an almost irrational sense of ability and confidence. We've lost before. Think of 2000, when Zero Knowledge [Radialpoint's previous incarnation] was down from 250 to 40 people and losing millions. But then we turned it around.

AH: With a lot of successful businesses, everyone likes to only think of the [media] myth. For example, when talking about Google or Apple, people think it was easy…

HH: Most of them fail many times, some of them move sideways…

AH: …And the ones that are successful had to experiment. Google didn't have a proper plan for their first six years. We know those guys. But Google had the swagger of being able to meet constant rejection. And you can't just think like that when things are failing. It's when things are going well that you have to raise your sights. Most people don't have the fortitude or the curiosity…

HH: … the stubbornness!

AH: [At Zero Knowledge] were wrong about the timing, the market and the way we were using the technology. But two of the divisions that we shut down have since gone on the become successes elsewhere. So being entrepreneurial is also about luck, timing, vision, value. When all those things happen at once, you get a hit.

HH: It's the 10-year overnight success that Austin's talking about.

AH: At both venture capital funds I'm involved with, the first rule is that we will not fund a lone entrepreneur. Do you know why? Because we won't give money to anyone who can't convince a second person to quit their day job. I remember one venture capitalist who coached me years ago. He said, "You're looking for people who are equal parts intelligence and stupidity. Who possess a clear view of reality as well as the ability to ignore reality."

HH: Our dad was entrepreneurial as hell, even though he didn't have his own business.…

AH: …He'd say things like, "I'm investing in this company and if it works we'll go to Disneyland." Well, we'd watch that stock portfolio. Being an entrepreneur is not about getting a college degree in order to get a nine-to-five job.

HH: There's a CEO I admire who's been an entrepreneur all his life. He's in his late 70s. I look on his bookshelf and there are books on subjects from anthropology to [Internet economics]. He told me, "I need to imagine what business will look like 20 years from now based on these trends." I always loved business. Austin always loved technology. We had this desire to figure stuff out.

AH: One thing I've noticed is the speed at which great entrepreneurs learn. They walk into a restaurant and they can't help themselves: Could you franchise this model? How can we make the service better? We rip each other's businesses apart and learn. The minute an idea starts, you can't help but think what to do next. When we were running TotalNet, we'd sit by the whiteboard some days and file an idea. Well, six months later, we'd see somebody sell the same idea. And having sat on the other side of the table, I have to tell you, there's no rocket science to venture capitalism. It's like betting on horses…

HH: …That's a nice hind leg…

AH: … And you have to prune the losers and recycle quickly, because if you don't, there end up being a lot of zombies out there—companies that don't know they're dead. They live off tax subsidies. In the Valley, it's a different attitude. People start a company, crash, do it again, crash, now you're better at it. You have experience. That's something else that density gives us: It gives entrepreneurs experience.

HH: …And cojones!

J0E MIMRAN, Toronto. Start-ups: 7, including Alfred Sung and Club Monaco

Currently: president, Joseph Mimran & Associates (creator of the Joe Fresh clothing line for Loblaw)

How does one develop into a serial entrepreneur? Well, I started being very interested in business and design at a very young age. I had an art gallery in 1974 when I was in university and before that, my brother and I had started a loyalty program, just as Visa was coming out. It was a student-based program and I was 14 at the time. I think it was in our blood.

How do you transfer what you've learned from one business to the next? There's a certain amount of risk-taking in being an entrepreneur, so you have to be able to live with risk. And you need the ability to not be daunted by anything, to have the belief you can climb that mountain. And vision. You have to be able to visualize that perfect golf shot. The same is true in business: you have to be able to visualize where you see yourself, so you know how to get there.

What about dealing with failure? Failure tends so freeze people up, so you have to have the ability to work through it. How you deal with failure is as important as anything else, because there's always failure along the way. And that's the true test of an entrepreneur: how do you get through those difficult times.

What drives you to keep starting businesses? I think it's the adventure of creating, the pleasure of creating. It's like once you start a painting, you have to finish it—you can't leave it half done.

What differentiates a serial entrepreneur from someone who tries to build an empire? I don't believe there's a big difference between them. Being labelled a serial entrepreneur doesn't mean you necessarily want to sell everything you build. You look for [the right] time to sell it. We still own Alfred Sung. Actually, Club Monaco/Caban were the only two businesses we sold and that's because the offer was so good.

Who's your entrepreneurial role model? There are quite a few people in the U.K. market who've been able to blend the business side with the creative side. Like Terence Conran, for example. He has built himself as a brand, whether it's the various design businesses he's been involved in or book publishing or restaurants. They're all very design-driven and yet there's a real business side to him.

What was your dumbest business move? Not buying real estate. If I had bought all the spaces that I had leased along the way, I'd be sitting on some incredible gains. My smartest moves were my timing in selling my businesses.

What's been your most thrilling moment in business? When we succeeded with Club Monaco in the United States, and New York in particular. When you can make it there, you can make it anywhere, especially in fashion, especially retailing. There's very few Canadian companies that had at that time.

What words do you think most define a serial entrepreneur? Vision. An adventurous spirit—I think that's really, really important. And you have to be tenacious. And creative. You do really have to be creative, to find the seams, and find these new opportunities. And opportunistic—in the best sense of the word.

What's the biggest entrepreneurial pitfall? You convince yourself of a great idea, you fall in love with it. You've got to be very careful to separate your ego from an idea.

How do you maintain balance between being business and other aspects of your life? You're either in the game or you're not. I think the notion of balance is a lovely one, but it's not always attainable, it's not always realistic. The question is, what is worse? If you get out of the game, do you miss the game so badly that you're out of balance the other way? Balance is different for everybody.

LORNE ABONY, Los Angeles. Start-ups: 5, including Petopia.com and Fun Technologies (online gaming)

Currently: CEO, Fluid Media Networks (digital music distribution)

When did you first realize you were an entrepreneur?

My first entrepreneurial venture was when I was about 15. I started something called the High School Battle of the Bands. I realized that kids had $5 in their pocket and nowhere really to go, so I started to throw dance parties at local nightclubs—no liquor, obviously. I started to get my sense of self-worth [from that]. It's very hard to get your sense of self-worth from being a great employee at 15. So having an idea and seeing it through from start to finish kinda started then.

I'm very convinced that you cannot learn to be an entrepreneur. You either are or you're not. It's like jumping or dunking a basketball: You can teach me how to jump, but I just can't jump like Michael Jordan can jump. And I can learn all the techniques and go to school for 40 years on jumping and get a little better at jumping, but Michael Jordan's just a better jumper.

Are there unique, innate qualities that an entrepreneur, particularly a serial entrepreneur, has? I think it's in your DNA. You have to be relatively intelligent. You have to be able to see things that other people can't see. You have to be able to problem-solve. I find sometimes I'll be in a room with 10 women or men and nine of them will solve a problem one way and I'll solve a problem another way. It's seeing the world differently. You have to, to a certain extent, be an iconoclast, because you have to challenge traditional ideas or, by definition, you'll go the traditional route—which, by definition, isn't change-making or entrepreneurial. You have to have the courage of your convictions, because this is hard. Starting something from scratch is really darned tootin' hard. You're always told it'll fail. Conventional wisdom is against you. The whole inertia of an industry—because usually if you succeed, you're effectively trying to disrupt an industry—is going against you. You have to be able to hear, "You're wrong," "You're dumb, "You're completely wiped out," "You must be on a different planet," and have the courage of your convictions.

Now, it's sort of sexy to be an entrepreneur. It's like a cool buzzword: "Yeah, I'm an entrepreneur." My favourite is when people who work at huge companies say they're entrepreneurial and their company is entrepreneurial. Well, there's not much entrepreneurial about a guaranteed pay cheque.

If your family started the business 72 years ago and you're the businessperson, you ain't an entrepreneur. I don't care that you're starting new lines of business and I don't care that you changed the organization: you never went through what it took. And an entrepreneur is not a person who runs a business unit at Sears or IBM. Because Sears and IBM aren't going under any time soon. If the sweater department at Sears isn't going great, well, the fridge department is, so it doesn't really matter.

How does background shape entrepreneurs like you? My parents are immigrants. Neither of them finished high school. I had a great and very loving upbringing, but we had not a cent. There are really only two drivers in the world: fire or passion. My wife's an artist and she's passionate about art. Whereas mine is fire. So [I thought], I'm sick of being embarrassed, and I'm sick of not being able to take a girl out when I'm 15. I don't know how you have fire if you come from a lot of money.

But doesn't growing up poor make it tougher to bear the risk when you're starting out? The concept of risk is actually an interesting one. Risk is inextricably linked to the courage of your convictions. People always say, "You must be prepared to take a lot of risk," and I don't feel like [what I'm doing is] risky at all. I'm convinced it will succeed.

What happens when you fail? I've had, obviously, setbacks in every part of my life, but so far, in business, I've been fortunate. But I'm very, very, very competitive, so I'm not really prepared to fail. And while I recognize that it's more socially acceptable to be self-deprecating and say I may fail, I don't really believe I will.

What drives you to keep starting new ventures? I think a sense of self-worth. Fun [Technologies] was a very successful business and we sold it to Liberty Media for $484 million. I took a little teeny bit of time off, but there's only so much sense of self-worth you can get from hitting a tennis ball. I really believe the music industry now is ripe for disruption. I think we've positioned ourselves well, with the right assets, and I think that's inextricably linked to your sense of self-worth: from dreaming about something that doesn't exist to seeing it through to exactly what you told people would change. If we are able to accomplish what I believe we're going to be able to accomplish, that will make me feel great.

The only time I wasn't entrepreneurial was a very short period of time when I practised law, and I was unbelievably unhappy. I've tried to analyze that and I think that comes from my immigrant background and being the first person to ever finish high school in my family. My parents got a lot of pride from their child doing well in school; they thought it was the panacea that I was a lawyer at a big firm. But I hated it. And it was funny, because the law firm said, "Oh, we're entrepreneurial," and I started all these initiatives at the law firm, but they all got turned down.

Where do you get your business ideas? I just think I'm intellectually curious. I love animals. I used to take my dog to law school and was always into pets, I understood the relationship between a pet and pet owner, so that was Petopia. The online games business was less from my knowledge of being a consumer and more from my view that the distribution of games—driving to Wal-Mart, buying a Bejeweled game, driving home, downloading it on your computer, that whole process—could be disintermediated by the Internet. And Fluid's because I love music. It's really a "long tail" story. It used to be that Madonna would sell 12 million CDs; now she sells one [million] and those other 11 million are spread over a large group of artists because the barrier to entry is much smaller.

How key is timing when starting or selling a business?

It's visited upon you. Sometimes I hear people talking about their exit strategy before they've even started. Our task at Fluid is to build a great online music company. If Universal or News Corp. comes along and buys us, so be it.

What have been your greatest challenges as a serial entrepreneur? Not having any money was really hard. Like, really, really, really, really hard. I almost have a chip on my shoulder about it—and I wish I didn't—but I sort of have contempt for people who've been given a whole tonne of money. I believe life should be a meritocracy and it isn't. It's not an Olympic race and some people start ahead of others. It's a little unfair when your dad gives you $50 million and, all of a sudden, you're allegedly an entrepreneur. Raising money is very hard. And being up against well-funded industries that want to crush you is very hard. As I mature as a businessperson and have more access to capital—intellectual capital as well as financial capital—it's a less formidable challenge, but it's a challenge always. The Universals and Sony Musics of the world want to crush me.

Do you think having this chip on your shoulder has given you the intestinal fortitude you need to take on those guys? Totally, totally bang on. I've always seen the world as "them" and "us," and "them" had money and I didn't. The good part is that this actually equips me well to take on and disrupt industries. I'm not the incumbent—I'm never the incumbent—which is why I'm pretty much unemployable. If somebody said to me, "Hey, great news, IBM would like you to be the CEO," I'm not wired well for that, because IBM's the incumbent, and my thoughts and ideas would not be well-suited for IBM.

Do you have an entrepreneurial role model? Nobody. I don't really believe in that whole mentor thing. It might work for some people, but it never worked for me. There's only so much you can imbue into somebody else. Michael Jordan could be my mentor in basketball and tell me, "Here's how you do it. You run up to the line and when you get to the line, you leap with your left foot, not with your right, and then up goes your knee and then you spin around three times and you put it through." Like, I just can't do that!

How do you learn and transfer what you've learned to each new business? Business is pretty much the same across sectors. While the businesses themselves are all tremendously different, the rules of success are very similar. Before we entered the music space, we probably spent five, six months learning absolutely everything, from margin to growth, return on investment. I mean, there's very little I now haven't learned about the music biz. But business is business. It's kind of like physics is tremendously different from biology, but go to every class and study really hard, and the same set of stuff will get you a good mark in biology as physics. Now, you may be a little better in physics because you kinda get it more, but it's really about being a good student.

What have been the most important lessons you've learned? Never ever give up, ever. And business is really, really hard. You have to be prepared to literally wake up every morning and feel like you're going to throw up from the pressure. Seriously. Like, every morning. You've got to be prepared to be sick, physically, from the amount of pressure that you face.

I think my biggest thing is, I try to find the smartest men and women I can and let them lead my organization. Like the woman who ran our investor relations department at Fun: I never second-guessed her decisions, because she knew more about it than me. I think knowledge and intelligence are very different. Intelligence is a function of one thing, and knowledge is a function of two things, it has a lot to do with experience. I like to hire intelligence as opposed to knowledge. I hire young people a lot. I hire young, smart people and give them tremendous ownership of their business unit.

All this stress you're talking about: How do you cope with it? I hate it. It's hard. I don't deal with stress well. Everything falls apart five, six times before it succeeds. Everything I've ever done has had four or five Black Mondays or Tuesdays or Wednesdays. I don't have a way of really dealing with pressure.

So do you have days when you think, "Why don't I just pack it in"? You'd still be really well off. Yeah, sure there are. There are times when I go, "Why am I doing this again?" I've done very fine financially. There are times when an investor is screaming at me and threatening, and you go, "Why on earth am I subjecting myself to this?" But you just keep marching along. If an investor yells at me, I can't really say, "Screw off. I quit as Fluid CEO. See ya." I just can't—I, of course, could—but I really can't.

What are the biggest highs that have made this worthwhile for you? Building the largest online games company in the world is pretty amazing, I thought. Going to bed and knowing that we had 35 million customers that registered on our site, that but for this business plan and the work and courage, 35 million would not have registered…. I've never been able to even visualize 35 million people, so I thought that was neat.

Even though it was much smaller in scale, I thought my early-stage businesses were really neat. I mean, the Battle of the Bands exists today. There were bands that, but for my concept, wouldn't have been heard by thousands of people and got record contracts. And there are still lawyers I know who have become heads of big law firms, litigators, corporate lawyers, who did hundreds of cases at Tickets.

What's your take on finding balance in life? I find that concept nonsense. Out-and-out, utter nonsense. If you love what you do, and you're always working with smart people, they by definition become your social group, they by definition are inextricably linked to everything you do. If you don't like what you do, then you need balance. There is nothing I would rather do than structure a deal, because I'm doing it with smart people. And no, I don't prefer a movie and, no, I don't prefer a walk in the park. For a short little while, I felt ashamed and thought, "I need more balance. I better start going to movies or watching baseball games." Well, I don't like that. It doesn't make sense to me that you can really love what you do, but balance is going to make your life better.

TERRY MATTHEWS, Ottawa. Start-ups: At least 9, including Newbridge Networks (telecom) and Celtic House Venture Partners (tech VC)

Currently: chairman, Mitel (telecom)

What drives you to keep starting businesses? Starting companies is something I know how to do. I have done it so many times and with so few losses—only two companies were total losses out of the 80—that I now have my own little formula about what works and how to get it right from the start.

Is being a serial entrepreneur a matter of personality or circumstances? I'm increasingly convinced that being an entrepreneur—the first time — is largely circumstantial. Which may partly account for the high rate of failure in start-up companies—well over 50%. But being a serial entrepreneur is something that I truly believe is deep-rooted in the individual.

I have been very vocal in my public advocacy for Canadian business leaders to give back to the industry: mentor young executives, sit on boards of directors, invest in new start-ups. Don't simply collect your wealth from your successful company and retire to the golf course. But it's sadly a very rare thing to find people willing to take the wealth they have earned and put it at risk again with a new investment, or put their personal reputation at risk by joining a new company.

What do you think differentiates a serial entrepreneur from someone who holds onto and grooms a single company or someone who buys other people's companies? Every business-school graduate will tell you that one of the important lessons drilled into them from day one was that many companies fail because the founder did not recognize when the time came to transition the leadership of the company. In the life of every company, a moment comes when the next major phase of growth requires a different skill set than what the founder possesses. Entrepreneurs are highly creative, aggressive and typically very reactive to the market—which are all great characteristics in a small, high-growth company. But as a company matures, it increasingly requires skills based around process and administration, or perhaps a more market-oriented focus versus product focus. If the leader fails to recognize the right moment to let go, then the company will often stagnate. Likewise, people who buy companies are typically financiers, not creators.

Who's your entrepreneurial role model? Among the great business leaders that I admire the most would be J.P. Morgan—a great Welsh industrialist—and Alexander Graham Bell.

What were your smartest and dumbest business moves? Smartest: founding my first company, Mitel. Certainly, Newbridge Networks grew to be my biggest company, and it yielded my biggest financial gains, but to this day I would still have to say that Mitel was the best move I ever made. Mitel was the company that captured the phenomenal technology transition that brought the first digital phone networks into existence.

My dumbest business move would be a tougher choice. It was more of a personal disappointment, where I made the mistake of deferring to pressure to sell promising young companies when I felt it was too early to sell. I've learned over my career that once a management team has conceded the fight and internal pressure has built up to sell the company, by then it's generally impossible as an investor or board member to influence people to reverse course, and the company will ultimately be sold. I now try to watch for signs of that pressure early and hopefully find ways to steer companies to continued growth.

How do you deal with the constant cycle of risk, failure and success? I have seen most of the ups and downs in the life cycle of a company many times over. I work with good people, patient investors and in markets that I know well. In the end, if you get the formula right, then the risk is minimized and the failures are rare. If you don't learn from both your successes and your failures, then you are ultimately doomed as an entrepreneur.

What qualities do you think define a successful serial entrepreneur? Persistence, dogged persistence and uncompromising persistence.

If there is any one piece of advice you could give an aspiring entrepreneur, what would it be? Don't be afraid to take an educated risk. I would never encourage anyone to invest in a silly idea or an "overnight success," but if you do your homework, understand your market and know what needs to be done to win, then go for it.

SUSUR LEE, Toronto and New York. Start-ups: 5 restaurants, including Lotus and Susur

Currently: owner and operator of Lee and Madeline's in Toronto; preparing to open a New York restaurant in October

What made you turn from a hired chef to a self-employed entrepreneur? I've been on my own for so many years—since I was, like, 14. Wanting to be independent comes from your nature and from coming to another country from Asia. I had the view that I had to survive. And I wanted to follow my instinct, to be free. Because when you work for people, [there are] certain things they require you to do. You have to cook the same thing all the time because it sells. Having your own business is a form of freedom.

How do you balance the creative and business sides?

My friends always ask me, "Oh, Susur, when are you going to stop? What are you trying to achieve?" And I say, "I'm not trying to achieve." Every day I wake up: "OK, I want to make some new recipes. I want to create some things." I even tell my children, "You have to go with something you love to do. The money will come. And you can't always think of numbers; then you'll be restricting your creativity." Then again, you can't say, "I'm an artist, I want to just spend money without thinking about it." It has to be the instinct of surviving, the instinct of understanding business.

How did you learn business? I didn't go to school very much, but I learned from experience. You can smell it; you can listen to it; you can see it; you can hear it. The restaurant requires all of those senses. So I learn, absorb, and over all these years it becomes natural to me if I decide to open a restaurant.

Hong Kong is known as one of the most entrepreneurial places on the planet. Was that a factor? Funny you should say that. I was just back in Hong Kong. I was sitting in a café, and I recognized the energy as people sat around me. Just the motivation of people wanting to get things done. And I realized the city is so business-oriented and everybody's motivated, so it becomes a very competitive environment. [Starting a business] just came naturally to me after growing up in Hong Kong, but it took me many years to recognize it.

What's the most important lesson or skill you've acquired as a serial entrepreneur? People skills. You want them to understand what your needs are—or your ideas, or your passion—so they follow through. So I have learned that you have to love people, you have to understand people, you have to understand culture.

What do you find is your biggest challenge? The motivation. When you are the owner and you are the leader, they always look at you: Oh, why is he successful? Daily things: what I do, the respect and the motivation, the care and the discipline, I have to show all that. Doesn't matter how bad a mood I'm in; I have to put on another face to continue. Because I'm leading the front.

Have you experienced failure? You know what—touch wood—so far I haven't failed. At the same time, the fear is always there. What if your chef's suddenly sick or decides to go somewhere else? The retraining process is very long.

Why did you decide to start a restaurant in New York? One of my dreams is going to New York City. When my first wife said we were coming to North America, there are so many movies and shows in Hong Kong showing New York—not very many about Canada—so I thought I was going to New York. I like the progressiveness. I like the challenge of people that love being open-minded. I love the big city. It's inspirational. People were trying to introduce me to New York, to go there, but I wasn't ready. I wasn't mature enough. But now I have more experience. I've learned more about business. So I'm ready.

Did you have a mentor in business? No, I didn't have any. I don't study; I don't read. I just go with my instincts. My greatest inspiration is my mother. She's very frugal and very smart at not spending money. And [while] she's not extravagant, she always [said], "When you buy a pair of shoes, you always buy the best one, because it will last you forever." I understand that philosophy.

Are there other chefs you view as successful serial entrepreneurs? No, because you see a lot of great chefs, really good at cooking, but then they're not very strong with business. They will have good partners. The partners will always be behind them, telling them, "Oh, you have to cut costs." My philosophy is, when you know what you buy and you know what you sell, then you will never go wrong. How would that fail: If the food is good, and if you know how to buy and you know how to sell? It's simple, very simple. I do sometimes [have] partnerships, but [the partners are] very silent. Basically, I run the whole show. Because a restaurant is a very flamboyant business, everybody wants to have a little bit of that stardom.

How will you manage having restaurants in two different cities? You have to trust the people you work with, and you have to give them opportunities to grow in order to help you grow. I have learned not to be so controlling, that they will not necessarily all cook the same way that I cook. It's not like selling jewellery; a restaurant has so much emotion.

What would you ask other serial entrepreneurs? I would ask, Do you have a life? [Laughs] Do you have a real life? Sometimes, no matter how successful you are, you have to own your time.

MARK AITKEN Toronto. Start-ups: 5, including courier company Pronto Toronto and Renaissance Securities. Currently: CEO, Veritprop (owner of the Verity Women's Club)

What drives you?

I'm curious, and I get dragged into industries that interest me at the time. I felt there was a demand for a courier business back in the '70s, then sold it because there was an opportunity to get out when one could maximize profit. I started this business because all those other experiences showed me that there aren't enough women in senior positions. But this is different because I'm at the back end of my career now. It's certainly a commercial business, but there's another aspect, which is giving back to the community.

Who's your entrepreneurial role model?

Richard Branson. He seems to have fun in everything he does. He's got a balance in his life. He's doing what he wants to do.

How do you transfer what you've learned from one business to the next? I think the key to success is an ability to read and persuade people.

What was your dumbest business move? I wound up a hedge fund. It had done OK, but it wasn't growing fast enough. I had a securities firm and that investment council, which managed the hedge fund, and one business was doing really well and making all the money, and the other was just sucking up the money, which was the hedge fund. So I wound it down, but those hedge funds did hugely well for their owners in the '90s. So, somewhere along the line, I forgot my own advice to persevere whatever obstacles you meet.

What's the most you've made in a year, and the least? I don't really measure money made in a yearly cycle. If you're an entrepreneur, it takes about five years before you have a substantial business.

What has been your most thrilling moment in business? Every time I start something, I get an enormous high. And then, of course, the reality sets in and the long road to make something work looms in front of me.

Do you feel any added pressure to succeed, being one of the few female serial entrepreneurs? And why are there so few? I think women aren't wired for being comfortable with taking a lot of risk, and it might be because of our nurturing DNA. We tend to over-prepare and over-analyze before we do something. Sometimes, you just have to plunge in there, roll up your sleeves and get going. You're never going to be totally ready. But sometimes, as a gender, we're not comfortable enough just plunging in.

What three words do you think most define a serial entrepreneur? Curiosity, passion, leadership.

What's the best advice you can pass along to would-be entrepreneurs? You don't start out thinking you want to start a bunch of businesses. That just kind of happens. I didn't set out to start a courier business and sell it. I just went down that track, then something out of the blue happened called a postal strike, and that meant this huge bump of business volume that could be executed at a lower cost. That was a really good time to sell if you were ever going to do that. So I think one has to be an opportunist. An opportunist has a negative sound to it, but actually, it's what entrepreneurs are: They take an opportunity and execute and capitalize on it. And don't go into a business that doesn't turn you on. You've got to get up in the morning and say, "God, I really want to get down there," and, "Gee, overnight I had a new idea, I can't wait to see if it works." That enthusiasm, that's all part of the drive.

If there's any one question you could ask other serial entrepreneurs, what would it be? How women work out the balance between being an entrepreneur and being the central figure in the household, balancing work and home and children and elder care. That's always a bit of a trick.

How would you answer that question? Gender-wise, we're too focused on having balance in every moment and every year of our life. If I look back, I feel my life has been in balance. But if you looked at it, you'd say, "Are you crazy? Do you realize you didn't do this and this during that year?" But you have to take a longer-term view. When your kids are really tiny and all you do is work [and go] home, and there's no texture in your life, no culture, no friends, no fun, all those necessary ingredients to have a balanced life, it doesn't mean your life isn't balanced. It means that when your kids are tiny, you have to deal with that, and over a longer period there's balance. Hopefully.

HARRY STINSON, Hamilton. Start-ups: "Probably a couple of dozen," mainly in real estate and hospitality

Currently: CEO, Downtown Hamilton Partners (real-estate developer)

What was the first business you started? The Groaning Board Restaurant. That was a job I thought I'd do in the summer during my first year of university, and I never went back. I was creating my own summer job. Because I had no clue what I was getting into, I didn't realize the concept of opening a restaurant and going back to school was completely idiotic. So I opened it and then realized that I was there—stuck.

What drives you to keep starting businesses? You decide that something can be done and that you want to do it. It's not that you want to do it just to have notches on your belt. It crosses your mind—perhaps in one blinding revelation or gradually over time—that there's an opportunity to do something, and some people go out and do it, and other people talk about it. And the entrepreneur is more motivated by the fact that they think it can be done than a business plan. Being passive is not something an entrepreneur metabolically does. Just sitting there and watching the clock is not something an entrepreneur can do. They're not conscious of clocks.

How do you transfer what you've learned from one business to the next? It's just cumulative. Problems are relatively similar business to business in their fundamentals: It's usually financing or legal issues. But there isn't one answer. The entrepreneur just tends to assume they can solve it. I don't want to sound condescending or cranky-old, but I haven't got a lot of respect for university courses in entrepreneurship. The sort of people who take them are not entrepreneurs. It's like writing a book on spontaneity. You can't tell a person how to be an entrepreneur. They either are or they aren't. You can help them with some experience and how you'd deal with the problem. Over time, you're able to solve problems better because you've run across them before, but you don't suddenly become an entrepreneur because of something you read or do. It's there: You just become better at it or you don't survive and decide you're not interested anymore.

How do you deal with risk being such a constant? You don't think of it that way. You wouldn't be doing it if you didn't think that it would work. When someone says, "You're taking a big risk," you say, "Well, OK, it's not going to be easy, but I think I can get there." It's [about] comfort zone. Brain surgery—to me, that's risky because I have no comfort zone; I don't understand it at all. To a brain surgeon, it's not risky, because that's their comfort zone. A lot of entrepreneurs go into business because they grew up in that field—if their parents were entrepreneurs, they're more likely to be entrepreneurs—and they're likely to become entrepreneurs in a field that they have some experience and confidence in.

Does the prospect of failure freak you out? Oh, it's a stress. But it's not stress that causes you to say, "I'm not even going to try." Sometimes, if you hit one giant home run, you can gamble in a lot of other things because you have the resources to do it, but if you don't succeed at something, it doesn't mean that takes the entrepreneurialism out of your psyche. The ultimate entrepreneurs are the ones who just keep trying. A lot of people would like to be entrepreneurs, but they don't really understand what entrepreneurship means. To them, it means, "I own the business. I have all the money. I get to make all the decisions. Boy, that sounds cool." They don't understand that it also means you're taking all the risk and all the stress. So there are two edges to that sword. The serial entrepreneur just accepts that and carries on. The non-serial entrepreneur is probably one who didn't realize that there was another side to it. They just saw the fun side, the upside. And when they encounter the downside, they say, "Oh, well, this isn't for me," and they go back to being an employee.

Who is your entrepreneurial role model? Walt Disney, and to some extent, Trump. Not in his garishness, but he's a very clever, persistent man. I read a lot of biographies of people who have gone through it, because you learn from them. [Robert] Campeau, in the sense that he was obsessed with building great properties. Same with Disney, he was obsessed with his product. You generally find the person who really is passionately into what they're creating or providing is more likely to hit the big time, and they're usually regarded—in fact, they're pretty much consistently regarded—as fanatical, as unreasonable, as difficult, as unrealistic. Because if you're going for a high goal, it takes enormous focus and persistence. When you're so focused, you can't be as smooth and polished and relaxed and understanding and pleasant and patient as people would like you to be. That's just the nature of shooting for the stars. If you look at an accomplishment, whether it's business or medicine or politics, people have had to rock the boat, break eggs. And in so doing, they've annoyed people, there's no question.

What's the dumbest move you've made and the smartest move you've made? Being persuaded to be reasonable when someone who is clearly not entrepreneurial talks you out of going full-tilt. Because it's not reasonable. When they tell you to slow down and you aren't there yet, it's a bad thing. And it's so common. The lawyer, the accountant, the banker: They sort of pat you on the head and say, "Really, you should be reasonable." And they don't understand that if you let up, the whole thing just falls apart. I think going into real estate as opposed to restaurants, that would be the smartest thing.

What's the most and least you've made in a year? I don't think any entrepreneur has any clue. Entrepreneurs don't draw a salary, because you're building businesses. If the business didn't work, well, you made zero, or a lot less. If the business did work, well, how much is it worth? It depends on who's valuing it.

What's been your most thrilling moment in business? To see 1 King West [condo and hotel project in downtown Toronto] physically completed and operational.

What words do you think best define a serial entrepreneur?

Persistence, imagination. A sense of humour. Possibly cynicism as well, in the sense that you don't take at face value what experts tell you.

What's the biggest misconception that people have about serial entrepreneurs? The misconception that annoys me the most is that entrepreneurs are not good businesspeople. That's so totally unfair, because the entrepreneur, generally speaking, is doing something that hasn't been done before. There is no rulebook. And then you've got the know-it-alls on the sidelines who have no skin in the game and have never dealt with this themselves making condescending comments about how you're just not a good businessperson. To them, a good businessperson is somebody who has no problems. Which isn't a businessperson in my mind. I don't consider bankers businesspeople. Not that they aren't smart—some of them are—but they exist in an environment where it's not their money. They don't experience the repercussions of a mistake, so their preference is to not do something than to do something and have it fail. Whereas the entrepreneur is constantly having to do things that are difficult, unprecedented, often under pressure, and the very fact that he survives says a lot. The best businesspeople in history, if you look at their whole evolution, the number of times they had setbacks and made mistakes is enormous. But they just keep doing it. Babe Ruth struck out more often than any other batter, but he also got up and tried more often. If you don't try, if you don't show up, it's not going to happen, and entrepreneurs tend to keep trying, often in the public eye, and then they're criticized for failures. Well, that's all very fine, except the people who are drawing a salary are usually drawing a salary because some entrepreneur has kept trying.

What's the best advice you could give an aspiring serial entrepreneur? Don't bother looking for a magic answer. I don't know how many phone calls and e-mails I get from people who think that we can get together for a coffee and I can somehow tell them how to be an entrepreneur. It's just so naive. There is no secret.

Despite all this pressure you've talked about, it sounds like you really love what you do. I do. I find parts of it very frustrating. But it's something I understand and I like being able to create something that people can admire and is permanent. Whereas I don't know that anybody's going to go down in history as the guy who created excellent PowerPoint presentations or developed a piece of software, because it's eclipsed and it's so transient. Whereas people will look at a building like the Eiffel Tower or the Empire State building—they're iconic.

How do you maintain a balance between being a serial entrepreneur and the other aspects of your life? There is no balance. It drives me nuts listening to people at seminars, experts and consultants, talking about achieving balance. That's BS. No serial entrepreneur has balance in their lives. They can maybe achieve balance after they become very wealthy and back off from their business. But I doubt it. They'll just open another business. It's a mythical word—I don't know what balance in your life means.

BRICK EKSTEN, Markham, Ontario Start-ups: 7, all in software and TV technology

Currently: CEO, Digital Rapids (broadcast tech)

What drives you to keep starting businesses?

I think it's that whenever I've had the time to contemplate what I'm going to do next, something has always been there—an opportunity or an idea presented itself, multiple ones usually. There's something I can really get behind, and it's typically in the vision stage, where feel that I can come up with a better way.

How do you transfer what you've learned from one business to the next?

Because I started young [at 17] and I didn't go to business school, everything I've learned on the business side, I learned as I went along. What you get really good at is prioritizing: what's the next right step. For instance, when you first start a company, you may not need marketing right away. You know it would be helpful to have marketing working right alongside development, but there's a right time to bring that on board as a business process. I get better at it. And every time I have a meeting with someone, I try to learn something.

Are you done starting businesses or are there more in you?

I never set out to start a business. It's always been because an opportunity's presented itself—either an opportunity to sell or something new happens [that interests me]. What drives me most is that I want to work in the best company possible, and I figure the best way to work at a great company is to be that great company.

What differentiates a serial entrepreneur from someone who tries to build an empire?

Of the people I've met who've had multiple businesses, the one thing they had in common was agility. They never lack ideas. There are lots of ways to hold onto a business, but there's also timing and opportunity that you should take advantage of in the best interest of the business. I've never understood riding a business into the ground. At some point, it made more sense to do something else. And what I recognize in other [serial entrepreneurs] is their agility and ability to make those tough decisions.

Who's your entrepreneurial role model?

Steve Jobs. I met Steve when I was very young and actually worked in one of his companies. While I personally don't like the guy—I don't even think he's that good a businessman—I recognize in him a drive that sort of overwhelms the traditional process and allows him to exercise his particular vision. And also the fact that he recognizes vision in others and empowers them to fulfill it. He seems to be singularly good at that. As somebody who grew up doing everything myself, my aspiration has always been to find that balance between the inner drive and empowering others.

What was your dumbest business move?

It happened very early on. I was swayed by an investor who was very flashy, had a lot of money, and talked me away from my core focus. He convinced me that I could make something happen, and maybe that's true, but it wasn't what I wanted to do. What I didn't recognize was that this guy wanted too much from the company and too much his way, so it wasn't a partnership. Not recognizing that upfront led me through years of pain, having to deal with somebody who was a terrible partner. And the one lesson that taught me was that culture is everything. If you don't share similar values, you're dead.

What's the most you've made in a year and the least you've made in a year?

I've held as much as $5 million in my hand, but I put it into something else five minutes later. It's never been about the money. To me, it's been more about the culture and the workplace and the vision and having control and driving it forward rather than trying to build the best financial outcome. The least I've ever made was probably $50,000 in a year and I think the most I've actually taken home as a pay cheque is close to $400,000. I haven't had a net loss yet.

What's been your most thrilling moment in business?

Meeting and working with Arthur C. Clarke. I had written a piece of software and his publicist got a hold of me and said, "Arthur's been playing around with your program, he really likes it and he wants to talk to you." I'm a huge science-fiction fan, so it's kind of like God wants to talk to me. He ended up writing a book around it.

What's the biggest misconception that people have about serial entrepreneurs?

Everybody thinks you're rich and I don't know where that comes from, because most businesses fail. I've been lucky enough to avoid that, but people think—especially if your business is known—that you're automatically successful. People also vastly underestimate the amount of work that goes into starting a company. A lot of people look at me and go, "Oh, you're working of yourself. Must be nice." And I go, "Well, I'm my own worst boss and I push myself to my absolute limits every single day."

What words do you think most define a serial entrepreneur?

Drive. Persistence. I think that's two different things. Persistence, you've just got to keep going, but drive means that you've got to run something down. You can't let it go.

If there is one question you could ask other serial entrepreneurs, what would it be?

I'd be interested to know how they find their life balance. For me, that's one of the big struggles: how do you balance your commitment to family [and your business]. A lot of people would come back with organizational answers, but I don't think that's quite the same. I think those days when the old mantra of "Dad's at work 14 hours a day, he's the breadwinner" is just not realistic anymore. We've got much bigger commitments to kids than we've ever had, so how do you do include your family in your life?

How would you answer the question you just asked?

I just force myself to set aside time every day. And this is a hard thing for my wife, A typical question, "How was your day?" is a question I refuse to answer. She's a stay-at-home person, she's got a full-time job raising the kids, and she wants to know how my day is, but I won't get into it because I have a hard time separating the emotion of work from the emotion of home.