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If Evan Chrapko doesn't understand a company, he won't invest in it.

Mr. Chrapko, who became a multimillionaire after San Francisco-based Critical Path bought a private Internet company he co-founded in Toronto, has definite ideas of what holds promise and what smells like, well, manure.

Raised on an Alberta farm, he went on to earn a Bachelor of Commerce in 1988 from the University of Alberta, a chartered accountant designation in 1991 in Toronto and a law degree from Columbia University in 1995.

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While he likes to keep details about his current investments to himself and his business partners, he's more than willing to share his views on the ups and downs of the New Economy.

"Everything can change in the tech sector. One day it's going to collapse, the next day it's going to go back up," he said over his cellphone during a business trip to New York.

"You have to weather the storm, ride the bucking bronco. You have to work hard with a lot of ethics and integrity. That'll carry you a long way when everyone else is losing their head all around you."

For Mr. Chrapko, 35, working in the New Economy has been a thrilling and happy ride up so far. In March, Critical Path paid $568-million (U.S.) in cash and stock to buy Toronto-based DocSpace, a leading-edge Internet document management company whose founders included Mr. Chrapko and his 32-year-old brother, Shane.

DocSpace's technology allows users to securely send, store and share large files over the Internet.

The Chrapko brothers and three founding partners, who owned roughly 60 per cent of DocSpace, walked away with nearly $340-million. About 45 employees and private investors also struck it big with their own stakes in two-year-old DocSpace.

Although Critical Path's stock price has plunged 68 per cent since March, DocSpace's founders managed to protect most of their windfall because they didn't keep many of their Critical Path shares long.

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By putting cash in the bank, Mr. Chrapko has stayed in charge of his own destiny and won the freedom to make investments where he sees fit.

The Chrapko brothers and Val Pappes -- their friend and business partner -- worked for several months under Critical Path's ownership, but they severed their ties on the fourth of July by resigning their jobs in Toronto. "We picked that date for its American symbolism -- Independence Day," Evan Chrapko laughs.

The three University of Alberta graduates are now partners in a private entity in Toronto called A-Live Holdings II.

"A-Live makes investments in companies at the startup stage that have something to do with the Internet. That's the gist of it," said Mr. Chrapko, who stands out in Bay and Wall Street crowds in his jeans and black cowboy hat.

"We're going to be smart money and not get into something we don't understand. We want to be value-added investors on the scene and not jokers.

Even while visiting New York this week, he still thought about the farm back in Alberta. "I wasn't born with a silver spoon in my mouth," he said, recalling his chores on the family's hog, grain and cattle farm in Brosseau, 120 kilometres northeast of Edmonton.

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His parents, Victor and Elizabeth, instilled the Prairie work ethic in their two sons and two daughters. Mom and Dad encouraged their first child, Evan, to feed the chickens at age four. While other seven-year-olds were playing with their toys, little Evan was castrating piglets.

"You have to respect and honour your roots," insists Evan's father, Victor.

With their hardworking farming roots, Evan and Shane Chrapko weren't fazed by living and working in DocSpace's cramped Toronto quarters, where they slept on the floor and ate wieners and beans out of a can.

But dreams have come true with their new riches. The Chrapko boys bought an upscale penthouse condo in Toronto with Mr. Pappes. The brothers also treated themselves to new, $500,000 Lamborghini Diablo VTs: silver for Evan and yellow for Shane. Mr. Pappes has his eye on a new Ferrari.

Life in the fast lane has its drawbacks, though, Evan Chrapko points out. "People's expectations are hard to manage. They think that if they get hold of you and you give them some free advice, that means you're automatically supposed to be involved with your money as an investor."

While steering clear of "some silly ideas," he remains on the lookout for good high-tech concepts. "We're sticking as close as we can to things that have proprietary, protectable technology and trustworthy management."

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The farm boy hasn't been blinded by the bright lights of the big city.

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