The Holy Grail for Internet advertising is the viral video. And while many an executive has uttered the words "we think this thing can go viral"—few actually know how to tweak Web weather patterns to create a "Sharknado."

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Well, the guy who rose to online stardom during the recession by starting a business as a professional T-shirt wearer thinks he knows. It's something he calls "an Internet advertising flash mob."

The idea is that, instead of just one guy wearing a company's shirt and generating buzz about the brand on Facebook, Twitter, YouTube and other social media sites, you get 500 or more people putting on a shirt and hitting the social media circuit—multiplying the buzz.

"Thousands of people were emailing me saying they want to be shirt wearers," said founder Jason HeadsetsDotCom. (And yes, that's his legal name—at least until the sponsorship runs out! He was known as Jason Sadler.)

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So, he thought—why not? Why not offer companies an opportunity to have not one, not two, not five, but 500 people wear their shirt at the same time?

"It's turnkey. We get the shirts. We get everyone to do it. We'll call it an Internet flash mob!" HeadsetsDotCom said. "It's something you can't get anywhere else."

It was actually tried last year when Pepperidge Farm came out with a new cracker called Jingos. T-shirts and samples of the product went to 500 people, who were sent them off into the Internet wilderness.

Five hundred people? How do you coordinate 500 people? If you've ever thrown a dinner party for 15 or more, you know that is like herding cats.

HeadsetsDotCom said that initially it took, on average, 20 minutes to send one email to 500 people, but after that he used Google forms to share answers to frequently asked questions.

Surprisingly, the disastrous part wasn't communications but shipping.

"Many of the boxes of crackers didn't survive the shipping!" HeadsetsDotCom said. "We learned afterward that we're going to have to ship things much better."

Still, he said, people who got crushed crackers rolled with it. They just washed their shirts and kept going.

The wearers came from all walks of life, according to HeadsetsDotCom, from college students to 9-to-5ers, small business owners, part-time actors "and everything in between." Even a few dogs got in on the action.

As for the training, "We just told people to have fun, be yourselves, and put the shirt on the right way! Our shirt wearers did the rest. … They didn't need much help being creative."

Geri Allen, the corporate and brand communications manager at Pepperidge Farm, said that though the company had some reservations at first about the effectiveness of such a campaign, it was "definitely worth the money."

"I was surprised how much people got into it and how clever they were. People posed with a box of crackers in some unusual places—bathtubs, kayaks and cars, with horses, dogs and even a bear!"

HeadsetsDotCom said that he estimates 500 people would have 100,000 followers total on social media (say 200 per person), which works out to 5 million impressions for the brand.

Allen said Pepperidge Farm was so pleased with the stunt that it would "most definitely" do it again.

But brand expert Rob Frankel said he's not so sure about the flash mob idea.

"It's a novelty, and novelties are almost never sustainable," he said.

Frankel's concern is revenue, the Achilles heel for many companies, from Facebook to The New York Times.

"After the top-line hype on the deal, you have to look at the bottom line. Is any of that linked to revenue?" Frankel said.

Of course, there's also the question of how you pay 500 people to wear a shirt—or do you?

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HeadsetsDotCom wouldn't disclose how much Pepperidge Farm paid for the stunt but said it was "less than $20,000."

He didn't pay the T-shirt wearers but is looking into some type of reward structure in which whoever has the most-shared photo or has made a really great YouTube video would get a gift card or some other giveaway.

And of course, the one question you have to ask is: After five years, isn't HeadsetsDotCom sick of wearing T-shirts?

In fact, no.

The T-shirt business brought him not only a six-figure job, but love.

He met his girlfriend, Caroline Winegeart, in 2010, when she invited him to come and speak at the University of Florida's advertising club. (She was its president.)

A year and a half ago, she joined the company, bringing her artistic and organizational skills. Just a few days ago, they launched their own online T-shirt store, featuring some of HeadsetsDotCom's favorite sayings for entrepreneurs, including "Innovate or Die" and "Fail Fast, Learn Faster," with designs by Winegeart.

"For five years, I got paid to wear shirts. Now I want people to wear shirts I design," he said. "The irony!"

Technically, he retired from professional shirt-wearing earlier this year to focus on other projects. Like being a pro athlete or dancer, being a T-shirt wearer takes a toll, he said.

"Five years was all my body could handle—my shoulders are gone!" HeadsetsDotCom said.

The real irony, perhaps, is that in an age of big data, where machines do everything from order us dinner to trade stocks, this big idea is all about the humans.

Until you can coordinate a flash mob of monkeys to wear shirts and tweet, there's some job security for us humans!