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NEW YORK (MainStreet) – Finding a good name for your company is hard enough, but switching to a new name after years in operation can be a monumentally difficult task to properly execute.

Online retailer became the latest company to learn this tough lesson when it attempted to rebrand itself as “” Although the company announced the name change in June, it began restoring the original Overstock name to its website and social media channels this month.

“We have been listening to our customers and have learned that we’ve moved too quickly in the transition,” the company said in a statement. “So we are going to down shift one gear by re-emphasizing and noting that continues to be a shortcut to our site.”

While (which used the domain suffix for Columbia rather than the traditional .com) was certainly an easy shortcut to the site, it turns out brevity isn’t always the soul of wit – and sometimes it can be downright confusing. In this case, it seems many people simply visited, which the company does not own, as they were unfamiliar with the non-traditional domain suffix.

“It’s a new concept, and it takes time for people to correct past behavior,” says Helen Gould, director of verbal identity for Interbrand, a brand consultancy. “And it’s so close to something that’s familiar: You see, your brain sees”

Gould says that she likes the basic idea behind the rebranding, which sought to expand Overstock’s brand beyond its original business model of selling only excess inventory; she compares it to 3M, which shortened its name from the wordy and restrictive Minnesota Mining and Manufacturing. But the failure of the name to take hold points to the fact that the already-challenging prospect of rebranding becomes even more difficult in the Internet age. Here are a few things that Web companies going through an identity crisis need to keep in mind before they pull the trigger.

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Consider your audience. Overstock is by no means the first company to use an alternative domain suffix for its Web address. Twitter uses the same suffix for its link shortener, and another link shortening service,, uses the Libyan domain extension. But those sites and services are geared more toward an educated and Web-savvy audience. Overstock’s customer base is likely much broader, and includes elements that wouldn’t be up on the latest trends in domain naming. “Customers who aren’t educated won’t pick up on those subtleties,” says William Lozito, chief branding officer of brand naming company Strategic Name Development.

Don’t get caught up in your online identity. This isn’t the 1990s, when dot-coms were a separate breed of business that could be neatly divided from offline operations. These days every major company has an online presence, and those who conduct most of their business via the Web no longer seek to emphasize their online nature. Take one of Overstock’s big competitors, – while that may be the official name, the company frequently refers to itself and its services as simply “Amazon” (as in, “Amazon Prime”). Given that, Overstock’s decision to rebuild its brand around a shortened URL seems ill-advised.

“In a world where everything is online, I thought it was odd that they would want to emphasize online-ness,” says Gould.

But watch out for that URL. While the Web address shouldn’t be the focus of your brand, it’s still something companies need to consider carefully when choosing a name. Lozito points to the pen company Pen Island, whose name resulted in an unfortunate Web address when it built a website (though we can’t tell if it’s an actual company or a joke site). There’s also, which is intended as a directory of agents and PR representatives but initially appears to be a different kind of site altogether.

Consider all channels. Netflix’s short-lived attempt to spin off its DVDs-by-mail service into a separate company called Qwikster was slammed by critics. Among the many issues with the poorly executed rebranding: The company failed to secure the rights to the @Qwikster Twitter feed, which turned out to be operated by a foul-mouthed user who frequently tweeted about his affinity for marijuana.

“I don’t think it’s an issue specifically for online companies, but companies in general,” says Gould. “There are so many new ways to be confused with someone else.”

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