The late ’90s and early 2000s were a roller-coaster ride of a time to work on the internet. (“Lived through the dot-com-bomb,” Askew would later blog, “although my 9–5 job did not.”) Askew taught himself to code websites, and manipulate and monetize invisible flows of web traffic using the new ad platforms deployed by Google, Yahoo, and MSN. When he encountered a blog post about domain investing in 2006, he immediately wanted in on the action.

By then, Askew was already years too late for the first domain rush, a period in the ’90s when far-sighted investors snapped up thousands of never-before-registered dot-coms. But 2006 was still what Allemann calls the “easy money” era of domain investing — a halcyon time, in hindsight, when even middling dot-coms and dot-nets turned profits via reams of display advertising. Domain names are bought and sold much like real estate, and investing inevitably gets more complex as the number of investors grows.

If the domain you want — GetRichDomaining.com, for example — has not yet been registered, you can do so for a nominal fee of $10, $15, or $20 per year, paid to domain registrars like Bluehost. But if GetRichDomaining.com is already registered by someone else, you must either negotiate its sale directly with the current owner or wait months or years for its current registration to expire and go back on the open market.

Few good domain names slip back onto the market without attracting the attention of multiple investors. Services like GoDaddy and Namejet compile daily lists of expiring domains and vie to “catch” them as they drop, allowing would-be buyers to bid prices up in frenetic, fixed-length auctions. Buyers then make money by “flipping,” “parking,” or “developing”: reselling the domain, running ads on it, or building content on it, respectively.

These first two techniques were most popular when Askew started in 2006 because they required little effort and could be quite profitable: Vodka.com sold for $3 million that year to a Russian distiller, and Diamond.com commanded a reported $7.5 million when it sold to an online jeweler. Askew couldn’t hope to land that quality of domain; instead, he set his sights on a third-tier domain, Arthistory.net, which he bid up using his Palm Treo 650 as he was driving back from a bachelor party in Key West. The auction price climbed as his faceless competitors trash-talked him. He was hooked on the whole process — and after Askew landed the property for $4,200, he set out to buy more domains.

He snagged the name of a picturesque lake in Banff National Park and the outdoorsy Appalachaintrail.com. He went through a brief Ole Miss phase, scavenging domain names from Vaughtemingway.com and Swayzefield.com to OleMissMotel.com. He got philosophical. “Expect to view the world as one un-registered domain name,” he wrote in a 2010 blog post. “Physical objects and banter on TV and radio will begin to transform into potential names to acquire. Don’t let this frighten you. This is normal.”

But by 2009, when Askew had entered a fugue state of acquisition, neither flipping nor parking worked as well as they once did. While the internet is nowhere near running out of dot-coms — there are, per the domain registry Verisign, 10^98 possible combinations, with 141 million registered now — competition for the best domains has grown fierce as massive, mainstream registration services like GoDaddy exposed more people to the market. Drop-catch sites, like the ones where Askew buys properties, battle for domains with automated software systems that borrow their tactics from high-frequency traders. According to a 2018 research paper, one in 10 domains is re-registered the second it expires.

Thies Lindenthal, a professor of finance at Cambridge University who has studied domain markets, says that it is likely that the rise of these systems has moved more and more domains into the portfolios of sophisticated, professional domain investors: both well-financed individuals and corporations, like GoDaddy, which has paid tens of millions of dollars to acquire top-shelf dot-coms. They have historically seen their holdings appreciate in lockstep with the NASDAQ 100, following the overall returns of the tech industry.

But marginal domainers like Askew face enormous challenges. “Parking” doesn’t return even a fraction of the profits that it used to. And flipping has grown risky because, among other reasons, new top-level domains, like .io and .ia, have depressed non-premium domain prices. “The majority of domains will see maybe one offer in 10 years,” said Lindenthal, who holds a small portfolio of domains himself. “It’s a massive, massive gamble that people take… It’s not a ‘get-rich-without-risk’ kind of market.”

Given that environment, it’s perhaps no wonder Askew’s model has become attractive. While flipping and parking domains was fun — and this is something Askew comes back to a lot, the bold-faced, Monopoly-board fun of it — he realized, roughly three years in, that he also had a knack for turning domains into quirky, miniature businesses that could withstand the whims of an increasingly turbulent market.

DudeRanch.com, his first full-fledged project in this vein, became an extensive, editorial directory of Western ranch vacations in 2009. Some ranches paid for feature listings, which began to justify his $18,000 investment. Building out the site also juiced its value as a domain.

In addition to DudeRanch and VidaliaOnions, Askew now also runs RanchWork.com, a job board for ranchers, and Brevard.com, a travel guide for the North Carolina mountain town. Askew went to summer camp there as a kid, and still takes his wife and eight-year-old daughter. They hike, mountain bike, and shoot short videos to compile listings for the site, which only accepts ads from locally owned hotels, restaurants, and tour operators.

“I sometimes say I prefer projects that focus on purpose over profit,” he wrote, in a recent blog post about his domain philosophy that hit the front page of Hacker News.

“I think people like the fact that he built the business based on passion and not just money,” Allemann says. “People [in the domain industry] are always looking for the easy money, versus building something that can potentially have a long-term future. It takes a lot of work… It’s aspirational.”

These days, Askew is selling onions, sure, but he’s also an unlikely testament to the belief that anyone can succeed on the internet with a little elbow grease and the right URL. Askew now makes enough money that he quit his last conventional 9-to-5, as a consultant to UPS, eight years ago. He says he’s not rich — his family still relies on his wife’s income, too — but his businesses generate combined revenues in the six figures. Askew hopes to cross the $1-million mark when BirthdayParties.com goes online this September.