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Second Time Around

Oct 1, 2009  

We asked three serial entrepreneurs what they learned from their first startup and what they’re doing differently today

by Suzanne Wilton

It’s 4 a.m. and Evan Chrapko just arrived in the United Arab Emirates from Karachi, Pakistan, on a mission to raise $600 million for one of his latest business ventures. The 43-year-old partner in Four Brothers Energy, one of several Alberta clean energy companies he’s co-founded, still has phone calls to make before an early morning meeting. It’s unlikely he’ll have time in between for a few winks.

Chrapko laments that he’s been on the road now for 22 days, having bid a silent goodbye to his two little girls, aged five and two, as they slept at their Edmonton home. Such is the life of a serial entrepreneur, the rarefied breed who is driven by the thrill of the startup. They are the deal junkies in a workaday world, the successful business builders who bring their ideas to life and become all-consumed helping them grow –
over and over again. Inevitably, they learned a few things along the way that contribute to their continued success. No business plan ever comes off without a hitch, but the benefit of hindsight can ensure you don’t repeat the same mistakes over again. For Chrapko, that’s meant focusing more on the team.

“Something that has been made clearer over the years is that it matters greatly that you have the right people in the right seats on the bus at the right time,” says Chrapko, a chartered accountant and lawyer. And they have to have trust in your leadership. It was Chrapko behind the wheel and brother Shane as lead navigator when the pair, along with five other partners, launched their first startup in 1999, Internet software company DocSpace. Within two months, a potential buyer offered $24 million for the company, but the northern Alberta farm boy, who was then living in subsidized Toronto housing and surviving on Kraft Dinner and hot dogs, turned it down.

Despite his decision to hold out for more, Chrapko’s team, living as frugally as he was, stuck with him and, more than two years later, were handsomely rewarded when he negotiated the sale of the company for $811 million.

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Were it not for the trust between the entrepreneur and his staff, that deal might not have happened. “The team that you surround yourself with is probably the most critical factor [to success],” says Chrapko, adding it’s an entrepreneur’s “own persistence in being relentless, or resilient in the face of naysayers” that also counts.

The toughest part is knowing who that dream team is and succeeding in hiring them, says Chrapko, who has gone on to co-found nearly a dozen other businesses with his brother, and more recently partnered with lifelong family friends, too.

He and brother Shane learned the hard way after a falling out with a co-founder of DocSpace, who misappropriated funds from a subsequent software company the trio started together. The Chrapko brothers successfully sued their former partner but > learned to be more vigilant as to where they place their trust. “We’re not immune to making a bad call,” says Chrapko. “I’ve got the battle scars to prove what I’m saying.”

Today, Chrapko is involved in almost every hire his companies make, interviewing prospective team members to ensure they are the right match. The best employee isn’t always the one with the best resumé but is the one who acts in the company’s best interest – rather than his or her own – when the chips are down. “We demand and expect a very high degree of accountability and ethical practices, but for the greater good,” says Chrapko. “The best you can be is brutally honest with candidates. Then it’s up to them to weed themselves out.”

CLOSE TO 140,000 new businesses are started each year in Canada. About 70% of them will survive the first year while only half will make it to three years, according to Industry Canada. Even fewer, just 25%, are still operating after 10 years. To an entrepreneur, however, statistics are like craps – a game of odds with manageable risks.

Calgary inventor Tory Weber took his first business gamble when he was about 23, cashing in a life insurance policy to fund a trip to a Toronto trade show with a template to cut stairs. Weber’s E-Z Stair, inspired by customer complaints at the hardware store where he worked, won a national order from Home Depot. “It was in my blood after that. I knew I needed to do this forever,” says Weber, 45, whose resourcefulness was forged through acts of desperation like dumpster diving for food as a child from a poor family.

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