He’s a bike messenger-turned-millionaire. He’s also a philanthropist and founder of the Better Government Party. Mike Mann is many things, but above all he’s a dot-com pioneer.

Mann, a native of D.C. — born “on M Street,” he said — had the occasion to watch the capital at work when he cycled through Capitol Hill as a bike messenger, founding his first startup, Marathon Delivery Service, at age 19.

When electronic means of communication began edging out the industry, Mann caught of whiff of what was coming. “I entered the Internet space around 1994,” he said, “literally before anyone knew what the Internet was.”

Mann's secret is that he is a 'human robot.' He once bought 14,962 domain names in 24 hours.

He got in the habit of buying domain names on the back-end for his website-building company. Then came the revelation: a $25,000 offer for (the now defunct) Menus.com, a URL that had cost him about $70. He took the deal, but the following day he was offered $75,000 by another buyer. “That was the day I decided, there’s no better profit margin in the world,” he said.

Before him, there was cybersquatting. Now, there is domain speculation.

When the business went mainstream, driving up the competition, he developed a new technology to make domain searches more efficient called WhoisPlus/NameFind. After a lot of hard labor and luck, he sold off BuyDomains.com in 2005 for $80 million, from an initial investment of $200,000. “I practically started the industry,” he said. “Whether I like it or not that’s my specialty.”

Mann’s secret is that he is a “human robot.”

He can browse through tens of thousands of domain names and buy hundreds every day, he says. “Usually I hit some threshold on Google — it cuts me off and makes me prove I’m human,” Mann said. With these superhuman powers, he broke a world record selling Sex.com (NSFW) for $13 million and once bought 14,962 domain names in 24 hours.

Funneling cybersquatting riches into the nonprofit world.

But Mann has higher aspirations for the fortune he’s amassed: leveraging his dot-com successes to benefit the dot-org world.

Among other initiatives, he runs Grassroots.org, a website that gives free technical advice to charity organizations, and gives out grants to technologically-inclined nonprofits through the Make Change! Trust. And through the Better Government Party, he wishes to tackle this “oversubsidized nation of corporations.”

Still, “the business gets harder and harder every day,” he concedes, what with the appearance of a new generation of pioneers in the alternative domain extensions space. But for Mann, they’re only cycling backwards to catch up with him: if a domain name with a novel extension abruptly rises in value, that will only make its dot-com alternative’s value shoot up as well. In short, said Mann, “dot-com will last for ever.”