What does hip-hop have to do with interactive marketing? Everything. At least that's how Russell Simmons sees it. See why.

Russell Simmons could have worn the Padres hat left for him by Rick Parkhill, CEO of iMedia Communications. But it just wasn't him, the hip-hop impresario turned business mogul told the crowd.

Instead, Simmons stuck with the crooked Yankees cap he brought with him. And his message, like his hat, combined elements of mainstream branding and hip hop style.

"The hip-hop community is the best branding community in the world," Simmons told the crowd, insisting that labels such as race, ethnicity and gender are all subsumed by the larger hip-hop umbrella. "Hip-hop builds brands. The hip-hop community is deciding if it's Tommy Hilfiger or if it's Ralph Lauren. They know if it's Coke or if it's Pepsi."

For Simmons, who has now jumped headlong into the interactive space with his GlobalGrind website, the power of hip-hop is ideally suited for the demands of the internet.

"This next generation is interested in a common thread and connection, that's what defines them," Simmons said. "Hip-hop is where you buy one ad that inspires everyone."

So how does Simmons plan to inspire everyone? The answer could be found at GlobalGrind, a portal he founded with the help of Jim Breyer of Accel Partners.

According to Simmons, the mission of GlobalGrind isn't to compete with any one hip-hop site. Instead, the portal aims to serve as a hub where users can find what matters to them.

"We call it web-filtered fresh," Simmons said, pointing out that the internet seems to mint new sites daily, but stumbles when it comes to organizing those publishers in such a way that users can find what they're looking for.

So what are hip-hop fans looking for from brands? According to Simmons, there's no one thing people look for from brands.

"If you have a fashion show, people won't take the whole line from one company, but they will tell you what they like and what they don't like," Simmons said. "And when they pick a brand, they believe in it because it's important to them and they want it to be cool because it's part of who they are."

But people are complicated, as Simmons pointed out when an advertiser for Volkswagen asked him a question.

"I have three Bugs at my Hamptons home," he said, adding a joke about doing an ad for the carmaker. "I love those cars, but not for the city -- you can't use them there. I could do a lifestyle ad for Volkswagen, but I could only do it in that section."

Such an ad -- if it were to materialize -- would no doubt carry with it the air of authenticity given Simmons' passion for the car. But when one marketer asked Simmons how brands -- many of which are viewed as outsiders -- could connect with the hip-hop community, Simmons only smiled.

"You need to be honest," he said. "Authenticity is about being honest. People will know if you're not honest, they'll tell you. What you need to do is figure out where exactly you connect and how to take advantage of that."

So where did the Padres fall short with their hat?

"It doesn't match," Simmons said.

By all measures -- color, style and fandom -- brand Padres simply made little impression on Simmons, a native New Yorker. But the Yankees cap, which has become something of a trademark for Simmons, proved to be a solid point of connection between the hip-hop icon and at least some of the digital professionals in attendance.

Michael Estrin is associate editor at iMediaConnection.