Here's the problem: There are four shots of tequila on the table in front of me and I need to choose one. Not just any one, but the right one. It's a rare rainy Friday night in Los Angeles and I'm three beers deep into dinner with millionaire playboy Harry Morton at his Century City Pink Taco Mexican restaurant, one of three he's opened in the U.S. The first, of course, is the flagship Pink Taco that sits just inside the lobby of the Hard Rock Hotel and Casino, the Las Vegas hotel that Morton and his father built up and then sold in 2006 for $770 million, the success coming in no small part from Harry's ability to shape the perfect party. Since then, the 28-year-old has returned to his hometown to do some under-the-radar investing in the city's nightlife. Most importantly, he bought the Viper Room, the legendary L.A. nightclub once owned by Johnny Depp. He also invested in DeLeon tequila, which is the cause of this impromptu taste test.

While Brent Hocking, his partner in DeLeon, pours a row of tequila shots, Morton leans over him, ogling the mock-up of the bottle. We're sitting in a massive leather booth near the back of the crowded restaurant, just across from a low-rider bicycle and a painting of a Mexican wrestler. Morton wears a plain white T-shirt, jeans, and Converse All Stars. As he talks about tequila, Vegas, and L.A. nightlife, he sips water, not tequila. He's currently on a no-booze kick. "I'm in work mode right now." Which isn't to say that he won't drink again in the future. "I get in waves and right now I'm on a work wave. You gotta be focused. When you're up there, people want to shoot you down or rip you down. They love to watch people fail. You have to really be on your game."

Morton talks like that a lot. It's a healthy mix of paranoia brought on by business sense and years of dealing with Hollywood bullshit. The combination pops up in his vocabulary: He peppers conversation with business school phrases such as "brand opportunities" and "integration," offsetting them with an occasional "dude" or "sick." When he's excited he throws all of the phrases together. For instance, DeLeon tequila will be heavily integrated with both of his brands and isn't this bottle design sick?

Which makes this impromptu tequila taste test that much more important. It is part drunken dare, part business research. Could Morton's tequila stand up to the others in a blind taste test? Fortunately, the entire experiment falls apart with the arrival of food and visitors, who stop to talk to Morton. I'm off the hook. Hocking and Morton discuss with one of the Pink Taco managers how the tequila is made, and Morton excitedly chomps his gum as he talks. "I like the creative process and coming up with an idea from the beginning and seeing it through the end."

One thing that has definitely ended for him is Vegas. "I avoid Vegas like the plague now," he says, holding up his hands. "It's like the scene of a crime to me: Don't go back! It's like the high school quarterback who leaves but still comes back to high school to try to hang out in the locker room. I went there, I did it, I learned a lot, I'm done. I've closed that chapter. I'm on to new avenues."

Yet when Hocking brings up a recent trip to Vegas for the opening of the new club XS at the Wynn Hotel's Encore resort, Morton can't resist asking about his old playground. "Really?" he blurts out. "How was it?"

Chances are you saw Morton if you visited the Hard Rock Hotel and Casino in the late '90s. He might have even carried your bags or dealt you blackjack. "I worked all the jobs in the hotel, from the front desk to bellman to engineering. I used to deal blackjack. I ran craps. I got in and learned the whole business."

Before his stint as bellboy, Morton grew up in L.A., where he attended the private Harvard-Westlake School with Jake Gyllenhaal and Jason Segel. His father, Peter Morton, created the Hard Rock Cafe restaurant chain, and his British mother, Paulene Stone, is a former model. His grandfather founded the Morton's steak house chain. The family lived just up the street from the Viper Room.

"I grew up above the Sunset Strip, so I was around it from as young as I can remember. Like, before the Keyclub or any of that stuff. I grew up in the early '80s, which I think was the coolest era. People will argue that maybe the '60s when The Doors were there and that whole movement was better, but to me it was early Guns N' Roses, W.A.S.P., Mötley Crüe. That was the best time. I grew up a one-minute drive from the Strip, just up the hill. Even as I kid going home at night I would see all the people out, the lights, the choppers. I grew up on rock 'n' roll music and the Strip."