Four years ago, Gary Vaynerchuk was a virtual unknown—that kid from Belarus who moved to Queens in 1978 and emphatically embraced capitalism, nimbly shifting from lemonade stands to a lucrative baseball card business to his dad's discount liquor store in Springfield, New Jersey. All that changed on February 21, 2006 when the energetic pitchman launched a video podcast called Wine Library TV. With his whimsically frank reviews—he's been known to compare certain vintages to Starburst candies and Big League chewing gum—Vaynerchuk quickly became a new media star, fielding interview offers from Late Night with Conan O'Brien, Ellen Degeneres, and Nightline. Today, at the age of 34, he's making yet another bold career move. As author of the best-selling Crush It!: Why Now Is the Time to Cash in on Your Passion, Vaynerchuk hopes to do for social media what he once did for Rioja. CEOs are lining up to hear what he has to say—shouldn't you?

Details: How does a kid from Belarus come to America and build a $60 million-a-year business selling wine?
Gary Vaynerchuk: Well, it has a lot to do with my parents. Sasha and Tamara Vaynerchuk—two classic Russian names—deserve a lot of credit. They not only instilled great DNA but also raised me in a great environment. More importantly, my dad started the business. So I walked into a business that was doing 3 million to 4 million dollars a year. It's not like I started from scratch.

Details: You seem to take a great deal of pride in the fact that you made your fortune in a family business as opposed to, say, a Proctor & Gamble or a General Motors. Why is that distinction so important?
Gary Vaynerchuk: You know, family is the single most important thing to me. I don't think that anyone loves corporations more than they love their family.

Details: But do you think it's made you more savvy in a way?
Gary Vaynerchuk: Yeah, I think that entrepreneurial spirit is always going to beat a PowerPoint presentation. You know that great saying: "He's got it" or "She's got it." That's not taught at Stanford. People who build family businesses are not classically trained. They have to deal with an enormous amount of politics. You think corporate politics are tough? Go work for your dad or your mom. The training you get in that type of environment is a good blueprint for success. I think a lot of corporations—now that we're moving more toward customer service—are going to have to implement more family-business tactics.

Details: Most guys think that the appeal of being the boss it that you get to call the shots. But you're all about the hustle. "What can I do for you?" Why is that?
Gary Vaynerchuk: Because I want to win bigger. Really. I'd love to say I'm Mother Teresa, but the fact of the matter is that I want to buy a billion-dollar sports franchise and the only way to do that is to make it about the employees and the customer. The second you turn on "It's about me" is the second you stop growing.

Details: In 2008, on the Late Show with Conan O'Brien, you compared a Pinot Noir to "the smell of a sheep's butt." I'm guessing you still have a few thousand cases of that wine stacked in the Wine Library storeroom.
Gary Vaynerchuk: Yeah, that might not have been the greatest call in my career. The thing that's most shocking to me is that America does not want to smell sheep's butt. I think it's a mistake, but, you know, there's only so much you can do.