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Naughty is Nice isn’t the only online dating game in town. Herb Vest’s is drawing more eyeballs and lonely hearts than ever.

By Joseph Guinto |
True CEO Herb Vest photography by Dan Sellers

Herb vest could have done a lot of things with the $128 million he got for selling H.D. Vest—a network of CPAs and tax professionals that Vest spent a career building—to Wells Fargo in 2001. He could have opened a restaurant. For that matter, he could have bought Deep Ellum. But, instead, Vest, now 63, took his windfall and sunk it into a dot-com. This, mind you, was after the tech bubble had burst. Makes you wonder. Why?

“After I sold H.D. Vest I became bored real quick,” Vest says. “I’m as much in favor of profit as the next guy, but I’ve always liked to have a social mission in business, to feel like I’m accomplishing something for people. So I looked at the divorce rate at 50 percent and decided we could do something about that.”

By “we,” he means, an online dating competitor to Match, eHarmony, Yahoo Personals, and others. True has drawn attention and users in part because it promises the safest online dating experience. True runs background criminal checks on its potential daters and takes pains to make sure that none of its paying members are surreptitiously two-timing husbands or wives. “The two things that separate us,” Vest says, “are our stance on criminals and married people being on our site, and the fact that we’re the only firm to do scientific compatibility testing. We actually have our tests validated and certified by an independent group.”

There’s something else that separates True from the pack—Vest. He’s a big guy with a big, Texas drawl and an outsize personality. When True ran into early financial troubles, which included layoffs in 2004 about the same time cut its own workforce, Vest came up with a new strategy: Attack the competition. He’s aggressively pursued state legislation that would require competitors to disclose whether they conduct the same expensive efforts to do criminal background checks on users. Vest once even paid for a full-page ad in The Wall Street Journal, wherein he attacked IAC/InterActiveCorp. Chairman Barry Diller—the big boss overseeing subsidiary

True has also sexed up its ads, something most other dating sites are reluctant to do. Vest says he’s spent some $50 million on a marketing push that’s plastered Web sites—including MySpace pages—with ads for True. The ads feature model-pretty women mostly, and some offer the come-on, “It’s nice to be naughty.”

The push is paying off. Vest claims 16 million users, a number higher than Match. One independent analysis shows True is drawing about 3.8 million unique viewers per month. That puts it near the top of the pack. (Yahoo Personals leads the industry with around 4.5 million unique visitors monthly.)

Says Vest, “We’re going like gangbusters.”

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