Following on the heels of a wildly successful technology company he’d launched while in university, Brick Eksten’s first full-time entree into entrepreneurship didn’t turn out quite the way he’d hoped. At the ripe old age of 23 and fresh out of school, he and his partners took on an angel investor to help bring a promising flight simulator to market. “We were young, and he had all the right moves: a nice car, lots of money, dressed well and wrote us a cheque for a large sum,” recalls Eksten. But shortly after the business was underway, the assets of the so-called angel were seized by the Swiss government as part of a money-laundering investigation. Eksten’s business was shut down.
What might have left the young entrepreneur clamouring for a risk-free day job only fuelled his fire. Eksten dusted himself off and got to work on a new firm — a developer of cutting-edge geo-spatial imaging software that gave users a first-person view of flying through Yosemite National Park, Mars or any other interesting landscape. It was a hit. Customers ranged from governments to land developers. But after a couple of years, Eksten found himself restless and bored, craving the excitement and vision that came with the early years of the business. “Once we had created the product, my role just became about fulfilling orders rather than really building something,” he says. “So, I sold off all my rights in return for a royalty and moved on.” Now 44, Eksten has owned seven businesses, and for the past seven years, he’s been at the helm of Markham, Ont.-based Digital Rapids Corp. (No. 4 on the 2007 PROFIT 100), which helps TV and film producers put video on the Web.
Resilient and passionate, Eksten typifies the 62 CEOs of the 2007 PROFIT 100 who have founded two or more companies during their business careers. Where others see potential failure, they see only potential. Where many are content running the same company for decades, they crave new opportunities and are willing to endure the high-stakes pins and needles of the startup phase. They get right back up after failures that would leave others down for the count, and they discover tons about themselves along the way. All business owners can learn a thing or two from these “serial entrepreneurs” about survival in the business world, resilience in the face of disaster and how to recognize and make the most of your strengths.
What drives serial entrepreneurs? Many are addicted to the rush of the startup. Indeed, the energy and raw potential of launching a firm can be intoxicating. “[The startup] is where I am in my element — all excitement, everything is positive, and the opportunities are there for you to take at will,” says Eksten. Serial entrepreneurs bear the stress of the startup, typically the most difficult and risky stage of a company’s life cycle, because most prefer it to the day-to-day humdrum of running an established, stable firm. “It’s always been hard for me to make the transition from a startup to a longer-running company,” says Eksten. “I’m just better at the early, vision stage.”
Most repeat CEOs are creatures of habit, getting into businesses in industries they know and understand. Take Hamnett Hill, co-founder and CEO of Montreal-based Radialpoint Inc. (No. 32). At 35, Hill has owned five businesses, all of them in the technology sector. To help pay the bills while at university in the early 1990s, Hill started a multimedia consulting firm that designed PowerPoint presentations for executives and corporate-training programs. At 21, he and his brother Austin launched an Internet provider in the early dot-com days of 1994, which grew to be the third-largest in Canada. When Hill realized how hard it would be to turn a profit — especially as big telcos entered the business — he sold the company to a firm that eventually became BCE Emergis. Hill then set his sights on the Next Big Thing on the Web: privacy. He and Austin started Zero-Knowledge Systems, an encryption company. When the tech bubble burst in 2001, Hill put the brakes on the privacy service, restructured the company and created Radialpoint, which provides managed Internet services for the world’s largest broadband ISPs.
There are those few, however, who are opportunistic, pursuing anything that appears lucrative, whether or not they have experience in that area. Craig Nadeau owned four radically different companies before he founded Maxim Group Inc. (No. 58). His CV of business ownership is an eclectic mix that maps out the path of an entrepreneur on the hunt. “I’m the type of entrepreneur who looks at what exists, where the market shares are, and I try to find angles that would make some business or service better,” he says. Nadeau has owned a travel agency, a home-building business, a sales consulting and training business, and a cellphone and pager company — all of which he sold or wound up. He chose his current industry — staffing — because he saw it as a “massive money-maker. There were only four or five companies in Calgary doing it,” says Nadeau. “I knew there was a huge opportunity.”
Spotting opportunity is Nadeau’s strength, but one of the benefits of being a serial entrepreneur is the chance to recognize and improve upon your weaknesses. In his early businesses, Nadeau had to face the fact that he was a poor delegator who would get bogged down in details and forget about planning for the future. “I would do everything myself,” he says, “and that’s never a good business model.” He forced himself to change when he founded Maxim in 2000. “I thought from a much bigger perspective from the start, mapping out what I wanted to do, what people I needed to have in place to do that and what kind of money would be needed to do it,” he says. “From the very beginning, I have never had a client. I brought in exceptional people to work with clients, leaving me free to plan the big picture.”
Coupled with their love of turning a profit and the knowledge that no one should put all their eggs in one basket, serial entrepreneurs have an insatiable desire to bring ideas to fruition. This means many of them are involved in multiple businesses at once, even if just as an investor. Hill, for example, has invested in his brother’s Segway business. Grant Robertson, president and CEO of MediaWave Communications Corp. (No. 49), whose past firms included an accounting and tax-consulting practice and an investment-conference company, uses his spare time to flip homes. Another sequential CEO from this year’s PROFIT 100, Roger Hardy of Coastalcontacts.com (No. 18), a Vancouver-based e-tailer of contact lenses, is still part owner of and a passive advisor to an online marketing company he started years ago.
Although some never completely leave a company they founded, staying on as an investor or advisor, selling a business is something most serial CEOs experience. At 37, Hardy has owned six businesses, and he learned a powerful lesson about selling very early on. His first formal business endeavour in 1999 was in the same line of business he’s in now — selling contacts online. With a modest investment of $2,500, the company garnered $70,000 in sales its first month. Not surprising, the competition was hungry to gobble up this successful newcomer, and although the firm had huge potential, Hardy couldn’t resist one particularly lucrative offer. But he soon regretted the decision. “It’s an exciting day when you sell a company, but the next day is a different experience,” says Hardy. “Once the business is sold, there’s a sense of loss. I put all this energy and effort into it, and I’d only had it for nine months. I was left wondering what I was going to do now — I mean, you can only go to Starbucks in Vancouver for so many days in a row.” As fate would have it, his just-sold business began to fail miserably, and he was able to buy it back in 2000, a move that was the genesis for his current company, Coastalcontacts.com.
Resilience could be the greatest gift of serial entrepreneurship. After getting through so much adversity, most begin to believe that, no matter what happens, they will land on their feet. “In the beginning, every single time bad things would happen I would think, ‘This is it, I have to kill myself, this is horrible’,” says Nadeau. “But as it happens, each time was tempering me, like when you put steel through a furnace. I look back at those experiences and know I could handle them now. I handle things like that all the time.”
Hardy was also more stressed in his earlier businesses than he is today. “I would be up at night sending e-mails to my team. They said I worried too much, but I would tell them that only the worried survive,” he says. But his worrying days are gone, replaced by a well-earned sense of peace. “These days, there’s the resilience of knowing that you will get back up, that there will always be setbacks. Eventually, you become accustomed to a certain level of bombardment.”
Regardless of their pasts, today these serial entrepreneurs own the country’s fastest-growing companies, which begs the question: for how long? Hardy says he’s home to stay: “The business has so much potential and a great group of people. I don’t see myself leaving.”
Others, however, are still peeking around the bend. “I’m really content, because I don’t think we’ll be out of this exciting stage for quite some time,” says Eksten. “But I know for sure I’ll want to eventually start doing something else.”
Hill concurs: “There’s still a lot we haven’t done yet in this company, but I don’t see myself doing it forever. You never know what’s around the corner.”