So you'd rather not spend your startup's precious cash on a million-dollar single-word domain--but still need to crack the URL puzzle?

Stakes are high and your timing is crucial when you're securing an address for your new company, says Jessica Scorpio, the founder of car-sharing service company Getaround.

"Your domain is really your brand, in a lot of ways. Like phone numbers, you don't want to be changing URLs unless you really have to," she says. And, she adds, you no longer can get away with simply procuring YourName.com: "As soon as you launch, squatters will buy every site related to your name around the planet, so you need to be ahead of them."

No sweat, right? Well, turns out the ecosystem has become slightly less painful for would-be website moguls in recent years.

For starters, remember that "no one inputs URLs directly anymore. A magic search bar takes care of that for you," says Eli Altman, creative director of A Hundred Monkeys, a branding and naming firm. He suggests putting an industry phrase in your URL--recall that Elon Musk's Tesla is still online at TeslaMotors.com. Or a customer prompt: Dropbox.com was originally GetDropbox.com. These days, the ubiquity of mobile computing has put far more emphasis on the app name--and its rank in the Apple Store--than on the URL.

Another option Altman likes: Find a top-level domain--or TLD--such as .beer or .NYC. Increasingly popular country-code TLDs "are still really effective," Altman says.

Before Hil Davis, the founder of BeautyKind, launched the online cosmetics retailer this past year, he sought out BeautyKind.com, but the price was too high--even after he hired a third party (called Name Ninja) to do the negotiating for him. Ultimately Davis combined Altman's strategies and bought BeautyKind.us--to be pronounced as in the first-person plural pronoun, and not the acronym for United States. "It sounds and feels inclusive," Davis says. "It implies everyone is part of the movement."

Not all TLDs are so warm and fuzzy. Experts even advise taking warning on some of the cuter-looking country-code TLDs, because occasional political complications can arise. Libya seized some startups' .ly domains in 2011. And .io is darling, but it's also the Indian Ocean, which has likely nothing to do with your startup, and is the most pirate-infested body of water on the planet.

There may be a more subtle reason to sidestep the cutesy TLDs, though, says Alexandra Watkins of the branding firm Eat My Words. "It may be clever. But just because it's clever, doesn't mean it's good."

"As soon as you launch, squatters will buy every site related to your name around the planet, so you need to be ahead of them."

Perhaps the best advice is to not get wedded to one name. Says Parker Conrad, the founder of Zenefits (he procured the URL for a mere $650): "It's best to have a whole bunch of names that you are considering, so that it is not a market of one. If there are 15 different options you're open to, you have a little more leverage to negotiate price--and won't be crushed if one doesn't work out."

Above all, avoid URLs that hamper pronunciation or comprehension, like that of bookmarking service formerly at Del.icio.us, advises Watkins. Using this approach can lead to headaches with spell checker, she says. And, she warns, it "also means Siri can't find you."

Published on: Dec 8, 2014