Jason Tesauro just might be the most popular man in Richmond, Virginia. A 38-year-old gourmand, author, and boulevardier with a fondness for wearing red corduroy pants and paisley pocket squares, Tesauro can swan into just about any specialty shop here in the erstwhile capital of the Confederacy and be greeted with a round of handshakes. He's more than a mere customer. You notice it as he floats through the smoke-perfumed sanctuary of the Old Virginia Tobacco Company. "Look at the veining on the cigar," he says as he and a salesman, David Johnson, inspect a Zino Davidoff that sells for $45 a stick. "It almost has a leather appearance. You can really see the oiliness on the skin. Here, follow that seam. I love being able to see the definition of the leaf."

"This is a passionate guy!" Johnson says. "He knows his smokes."

More important, during this era of anxious austerity, Tesauro buys those smokes. In bulk. A few weeks back, he swung by the cigar shop and dropped $500. On any given day he might ring up Matt and Tim Gearhart and give the two young chocolatiers an order for 500 criollos, 500 Earl Greys, 500 Michigan cherries, 500 pistachio toffee oranges, and—hell, just about every chocolate the brothers have in stock. If Americans were supposed to stop consuming luxury items in the wake of the recent financial implosion, it seems that this Virginia gentleman never got the memo. Tesauro, a divorced father of two and a co-author of the 2002 book The Modern Gentleman: A Guide to Essential Manners, Savvy & Vice, is a not-so-secret agent on the front lines of what he calls the underground-decadence movement. While the conventional wisdom tells us that rich and powerful people reeled in their profligate spending habits around the same time that Bernie Madoff became a synonym for Satan, the reality is that a lot of American elites simply went into speakeasy mode: They kept living it up, but they carefully concealed that fact from the outside world. "The consumption is still taking place," Tesauro says. "The conspicuousness is what's getting played with." As he explains it, big shots from nearby Washington, D.C.—defense contractors, lobbyists, et al.—are in something of a bind. Their business model is based on the time-honored tradition of seducing others with extravagance, but these days guys like that need to be careful that the extravagance isn't so extravagant that it turns them into bull's-eyes for gossip columnists. "They want to entertain their clients, but they don't want to make a splash in the headlines," he says. To avoid that, a contractor might turn the dirty work over to Tesauro, pay him a hosting fee of $10,000 per event, then pass along a credit card and encourage him to buy to his heart's content. One client, Tesauro says, "gave me his black American Express to go in the wine shop, and instead of him running into the neighbor who's dealing with foreclosure, I'm loading up the car. He doesn't have to deal with walking out of the shop with teetering cases of first-growths and having someone pointing the finger and going, 'You aristocratic so-and-so . . . '"

Curiously, these are flush times for folks who specialize in what's alluringly under the radar. At Dehouche, a travel company that arranges "bespoke" trips to South America, business is abloom. "We've found it incredible, actually," says Paul Irvine, who cofounded the firm in 2003. "We started off last year, 2009, having our best month ever in January, which was absolutely ridiculous because it was the peak of the economic crisis. September 2008 was when Lehman went down. And then we continue in 2010 to have our best months ever. We've been scratching our heads, wondering why are we doing so well." As odd as it may sound given his company's premium offerings, Irvine believes that the old, reliable notion of value has something to do with it. A Dehouche-curated trip to Brazil or Argentina, he says, might involve transportation via speedboat or horseback and private off-the-grid dinners cooked by some of South America's finest chefs. "We try to spice it up, put interesting things in there to get you under the skin of the country," Irvine says. "It's not about visiting international hotels, sipping piņa coladas, and eating club sandwiches. People are being more intelligent about how they spend their money. They say, 'Okay, I can spend $20,000 on this villa, or I can spend $15,000 or $20,000 on this trip that takes in three locations across Argentina.'"

This is why you might hear Irvine gushing about a suckling-pig feast that his clients get to sample in Brazil—a repast that involves crisping the pig with a blowtorch so that "in front of your eyes, immediately, the skin just puffs up like a cauliflower. The cook cracks it with a spoon, and you've just had the best suckling-pig experience ever." And this is why you might hear John Yetman, a finance guy in Bethesda, Maryland, raving about the customized array of cigars and chocolates that Tesauro unveiled at a recent function. In the end, Yetman explains, Tesauro's approach makes budgetary sense. "You get a better experience for less money," he says.