AskMen.com founder Ricardo Poupada on the set of a video shoot.

One of Canada's most successful web stories starts with a pair of white tube socks. Ricardo Poupada and Chris Rovny were 23- and 22-year-old marketing and finance graduates fresh out of Concordia University, sitting in a Montreal café in 1999 debating their future. The duo briefly thought about getting into real estate, but like most recent students, they were far too poor to front the capital needed for any realistic attempt at it.

Just then, a well-groomed man in an expensive suit and designer shoes wandered into the café, evidently for a date. Poupada and Rovny were impressed by the apparent player, but recoiled in shock when he sat down to reveal his Achilles heel — or Achilles sock, to be more accurate. Rather than an inconspicuous black, his socks were a glaring, blinding white.

"We knew that as soon as the girl saw the socks, the date was over. Sure enough, when she showed up she gave him one of those horror-movie types of looks and we knew the guy was done," Poupada says. "It just goes to show that even if you're the smartest guy, you sometimes forget the smallest details."

The incident set off a light bulb for the friends, who quickly cobbled together a website devoted to giving men dating and relationship advice. The message of the first article on AskMen.com, written by Rovny, was, of course, "don't wear white socks."

That was 10 years ago. Thousands of manly advice articles later, AskMen.com is about to celebrate its first decade as one of the most viewed websites among young men worldwide, attracting more than 12 million unique visitors a month.

Along the way, its founders struck it rich when the site was bought by IGN Entertainment in 2005 for $17 million. Rovney and Luis Rodrigues, a third original member of the team, left in 2006 shortly after the acquisition but Poupada stayed on board as general manager and vice-president. A decade at the helm of a successful site has given him a unique perspective on how the web — and doing business on it — has changed during a time in which the internet went fully mainstream.

More difficult market

The biggest difference now, he says, is how difficult it is to create a successful website. In the late nineties and early 2000s, the web was still fairly new and there wasn't much competition, so eyeballs came relatively easily. With the rise of social media, web entrepreneurs are now in for a tough time.

"I would be scared to start a site today. The barriers to entry are so low that literally anyone can jump online and there's so much competition for attention and resources," he says. "Now, if you don't have a Twitter strategy, you're dead. If you don't have Facebook Connect integrating the content with Facebook, you're dead in the water. The sophistication level of users and the customization they require … has completely changed."

That wasn't the case in the early days, when things were much simpler. The name "AskMen" was chosen, Poupada says, to take advantage of how the search engines of the day worked. At a time when Google and its algorithms were still in their infancy, search engines such as Yahoo and AltaVista were similar to phone books. Websites were often listed alphabetically in search directories, so a name that started with an "A" was imperative. That way, anyone looking for a men's site would come across AskMen first — and hopefully click through.

It was a primitive form of "search engine optimization," a phrase that can make or break a business today by forcing websites to tailor their keywords to Google's algorithms.

AskMen had 500 visitors on its second day and, by using its search strategy and word of mouth, saw daily traffic grow to 50,000 within a few months. In the heady days of 2000, before the technology bubble burst, that sort of growth made investors froth at the mouth. Poupada and Rovney got an infusion of $500,000 U.S. from some investors they knew, which helped them hire some writers and programmers to get the site off the ground.

Stinginess paid off

The founders were stingy with their money, which helped them survive while competitors failed. TheMan.com, one of those rivals that took aim at the same male, 18-to-34 demographic, landed a whopping $17 million US in funding in 2000. One of the first things that site's founders did was spend $3 million on a billboard ad in New York's Times Square. TheMan.com sputtered spectacularly on those kinds of expenditures — 10 months after launching, in November 2000, it went bankrupt.

The failure turned out to be a huge boon for AskMen, as TheMan had had a deal to provide content for a new men's channel on Microsoft's MSN portal. Microsoft had spent a good deal of resources building the technology to host the channel, but found itself with no content to feed it - so the software giant called up Poupada and his crew.

"We couldn't believe it. We thought it was one of our friends playing a joke," he says.

The deal was signed and AskMen content started appearing on MSN's site, with AOL picking it up soon thereafter. Before long, AskMen was topping rankings in its demographic with measurement agencies such as ComScore and Nielsen. By 2004, it was averaging about seven million unique visitors a month, which is when IGN came sniffing around.

The web entertainment behemoth had the top two sites — video games and entertainment — in the 18-to-34 male demographic, while AskMen ranked third. The Canadian site was outdoing its traditional rivals, or men's magazines such as Maxim, FHM and even Playboy. For the magazines, the situation was similar to one that newspapers find themselves in now — despite having a huge head start on the web with brand recognition, they were hobbled by an overreliance on their printed product. They took to the web reluctantly, dribbling out content rather than trying to build advertising-based businesses.

"They held onto the print magazine with dear life. They didn't realize the impact of opening up their site and selling advertising," Poupada says. "That really prevented the growth."

Small size surprising

IGN executives, expecting a big and busy operation, were shocked when they visited AskMen's Montreal offices and found only 12 people working there. The company had been profitable since 2001, largely through advertising sales, but it was stretched thin for expansion funds. Also, by 2004, the founders were getting worried that traditional media was finally getting wise to the web.

"We had people calling us saying we're either going to buy you out or we're going to take that money and crush you," Poupada says.

Like so many Canadian technology-based startups, the site's founders made the prudent play and sold out. It's a fact of life of doing business in Canada, Poupada says — Canadians can come up with great ideas and companies, but Americans tend to have much deeper pockets and they can catch up quickly.

'We're not as driven by ambition as our American counterparts but it doesn't mean we can't be as successful.'—Ricardo Poupada

Selling to IGN, which was soon after bought itself by Rupert Murdoch's News Corp., also gave the site the resources to expand internationally. AskMen has seen its staff grow to 25 and now has offices in several countries, with one recently opening in Australia.

Despite the business realities, Poupada still feels Canadians can compete with Americans. Canadians are generally more worldly and outward-thinking than Americans, he says, which gives us the right mindset — if not the means — to expand internationally.

"We're not as driven by ambition as our American counterparts but it doesn't mean we can't be as successful," he says. "We're in many ways better positioned than American companies to take advantage of the web." As for the unknown man in the café all those years ago, Poupada believes he owes him — and his white socks — a debt of gratitude for getting it all started.

"I should find this guy and write him a cheque," he says.