Minor doesn’t appear to have grown any more adept at comprehending the feelings of those who inhabit his world. He takes a lot of credit for 8020 Publishing, which is owned by Minor Ventures and currently produces JPG and Everywhere, two glossy, user-generated magazines. (Everywhere, 8020 recently announced, is suspending publication.) But the concept for these came from Derek Powazek, a Web designer who began publishing JPG two years before being invited to meet Minor. When I ask about Powazek—who was pressured to leave 8020 within months of its being funded—Minor trivializes his contribution: “He had a little pamphlet of photos collected over the internet.”

Meanwhile, Powazek says of 8020, “That was my life’s work.”

On the day I arrive at Minor Ventures, which houses six startups that share human-resources and accounting staff, everyone looks conspicuously fresh-faced. Asked if youth is a prerequisite for receiving funding, Ron Palmeri, a former tech executive who runs Minor Ventures’ day-to-day operations, suggests that it often is. “People at the beginning of their career don’t have a lot of baggage,” he says. “We tend to like people who are early in their careers, because they haven’t developed bad habits.”

Minor’s firm operates like this: It brings the kernel of an idea to a potential company founder and offers a funding commitment of nine months to a year—about $1.5 million to $3 million. Then, three months later, Minor Ventures starts talking about the second round of funding, offering an “expediency premium” to stay with him instead of seeking outside money. This proposal expires after one week. Five of Minor’s seven startups have sought outside funding; only one received a better offer from another V.C. firm, which Minor successfully countered. Says Minor, “I tell them, you can take this deal right now, or you can go out, see all the V.C.’s on Sand Hill Road, get their best deal, whatever. But when you come back to me, I’m going to pay market. And they go out and talk to the V.C.’s, and they get a price, and it’s lower than what we’ve offered them. And we take more of their company.”

Craig Walker of GrandCentral, one of the companies in Minor Ventures’ stable, is among those who sought outside funding but says Minor’s contributions were crucial. Minor sent the startup back to the drawing board twice before allowing it to release its first product. “Other V.C.’s focus on five-year financial projections,” Walker says. “Halsey is more, ‘Hey, run the business, but when it comes to the product, let me get involved. I’m going to tell you what I think.’ And Halsey knows consumer services on the internet better than anyone.” In 2007, Google bought GrandCentral for $50 million.

Back at his Virginia estate, Minor speaks excitedly about a venture that risks no backtalk: his racehorses. Last year, he spent $3.3 million on a filly named Dream Rush; more recently, he paid $3 million for Fierce Wind, a “puny” horse that, he says, everyone, including his mother, told him not to buy. He bought the Thoroughbred anyway, seeing in the animal “a rare desire to win that allows him to rise above and exceed his physical capabilities.”

Minor is so confident of Fierce Wind’s potential that he urges me to watch the Florida Derby, calling it “a chance to see the product of my style in action, for better or worse.” On race day, Fierce Wind suffers an injury and is outrun after the first turn by the winner, Big Brown, the horse that would go on to win the Kentucky Derby and the Preakness.

Minor’s family has deep roots in Charlottesville. His great-grandfather Colston Minor and his great-great-grandfather John Barbee Minor were both law professors at the University of Virginia, and there’s a Halsey Hall at the school, named for his mother’s family.

When Minor was young, he found Charlottesville a little too quaint for his tastes. “Halsey was part of a group of us who were kind of jocks and the wild crowd, and sort of ran our sequestered school,” says Kellam Ames, one of Minor’s boarding-school friends. He and Minor had to spend the week before graduation tearing down a school barn to work off demerits. “That involved bringing a cow upstairs into the main building,” Minor says.

Though CNET brought Minor to the West Coast, where he still owns homes, his love for Virginia remains so strong that in 2007, he told a local paper that he was interested in becoming governor. Asked about it again, he nods. “I’ve been saying that for a long time, and I get more serious every time. I always have plenty of things I want to see, do, change.”

Minor—a Republican who admits to voting twice for George W. Bush—is surprisingly humble about his chances of winning. “I don’t spend enough time right now in Virginia to understand the complexity of the issues,” he says. “And I think I’m too blunt, ultimately.”

A moment later, humility goes out the window. “Why I think I’d be good, even though I’d be blunt, is that I think I’m very creative. I think I’m a good problem solver. And, you know, I have faith in my own decisionmaking process.” He adds, “Thomas Jefferson had James Madison to kind of make things happen. And maybe I’ll find a James Madison, and he can take my idealistic visions and get them implemented. ”

No one doubts that Minor would spend what it takes to get into office, though there is some speculation about how much money he has left to blow. While he made $300 million from Salesforce.com, he says he had to split his assets with his ex-wife, Deborah, after they divorced. Deborah and their three children still live in the home she and Minor bought 10 years ago, he tells me, a Mediterranean-style mansion in San Francisco’s ritzy Sea Cliff neighborhood that’s now worth $20 million.