Frank Schilling made his fortune in the aftermath of the dot-com bust, buying up thousands of domain names others didn't want. He kept at it, aggressively building a portfolio of more than 320,000 domains that, through a combination of ads and outright sales, have made Schilling a decamillionaire many times over.

Now the 43-year-old domainer is going after what he sees as a far bigger opportunity. He's put up $60 million of his own money to stake his claim on a giant, emerging piece of the Internet -- the opening up of so-called generic top-level domains, or gTLDs, to include pretty much anything. The king of all domain extensions -- .com -- is under attack as never before.

"This is absolutely the future," says Schilling, whose new venture, Uniregistry.com, has applied to run 54 new top-level-domains. "We're at this point where the dot-com name space -- the entire name space -- is exhausted."

Canon.com in favor of using .Canon. Google could use Movies.YouTube. And you, dear frustrated domain-buying consumer, could eventually find it a whole lot easier to register a domain name you want without having to pay fat prices that Schilling and his ilk demand on the aftermarket.

It's not just the hard-core denizens of the domain world that are going after new TLDs, which are also known as "strings." Others are jumping into the fray. The most intriguing is Google, which in late May revealed that it's applying for an undisclosed number of strings, including .Google, .YouTube, .docs, and .lol. ("Despite the great opportunities the Web has enabled for people around the world, there is still a lingering question about the diversity of the domain space," Google's chief Internet evangelist, Vint Cerf, wrote in a blog post).

Demand Media, whose business includes Go Daddy competitor eNom, has said it's spending $18 million to go after 26 strings. And a number of lesser-known companies are competing -- some of which, like Schilling's new business, have sprung up specifically to participate in this digital landgrab.

"We've made more than $100 million in bets," says Dan Schindler, a co-founder of Donuts.co, which raised venture capital money to go after 307 strings that it won't reveal before tomorrow. (Notice that the new company's name sits on a .co and not a .com. Why? Because Donuts.com is a parked site owned by a domainer who wanted far more than Shlinder and his team would pay).

Avoiding land mines
All told, these companies have applied for 1,900 strings. Yet even after tomorrow's big reveal, as it's known, a whole lot of messy work awaits. Brands such as Google will simply get their TLDs because of their trademarks. Other claimed brand names will surely lead to disputes, Evencountries can protest names.

"It's going to be a minefield fraught with delays," predicts Schindler.

Then there's the overlap problem. Here's an example: Both Schilling and Google want .lol, as might others. Schilling also wants .home, which happens to be on Go Daddy's shopping list as well. And that's just two. Collisions will doubtless occur on many of the best generic names: .music, .free, .cars, .game, and on and on to dot who-knows-what.

Go Daddy CEO Warren Adelman is skeptical of all the new domain extensions.

(Credit: James Martin)

This is hardly surprising. Choosing strings, like speculating on domain names, includes a bit of instinct, but it's far from random. Donuts.co., for instance, used proprietary software to help it come up with its list, examining 25 parameters that include popular search phrases on Google as well as keyword bidding trends.

All this will lead to months of backroom negotiations. ICANN is asking those involved to try to work out deals. Only when that fails will ICANN hold an auction for the names. Presumably, the big shots like Google will get what they want, but not necessarily. The smaller firms could, for instance, try to team up with a competitor or bring on more investors.

"We may have to fold on some of these," says Schilling, "but we'll try to take them all to auction."

Even after this all shakes out, with much of it stretching into 2013, these new registries will have a ton of work and deal-making to do. Think about it. Of the 22 gTLDs already out there, most are shadows of the giant that is .com, which now claims more than 100 million domain names. Who do you know who uses .pro or .museum?

"We've been living in a .com world since the dawn of the Internet," says Warren Adelman, the CEO of Go Daddy, which in addition to .home, also applied for .casa and .GoDaddy. "Whenever you're doing something other than .com, it's kind of swimming upstream."

Struggle for shelf space
Which is why all these new players will want Adelman's help making that arduous swim. Go Daddy, after all, sells more than half of the domain name registrations in the world. So while these new registries will be technically allowed to sell names directly to consumers, acting also as the registrar, they're going to need partnerships and marketing help to get any attention.