Like most young men, Wayne Rollins frequently changes his mind about things. For instance, eight years ago he left the comforts of his hometown, Atlanta, for the excitement of Los Angeles. “I like change,” says the 34-year-old, while conducting a tour of his home, a modern aerie not far from the Hollywood Bowl. “I wanted to learn new things and know a new city. I came here hoping to evolve as a person.”

“Evolution” is a word that can also be used for the growth of his rather eclectic art collection. The first piece he ever bought, shortly after turning 21, was by Atlanta-based artist Radcliffe Bailey. “It spoke to me,” he says. “It wasn’t terribly expensive—maybe a couple thousand dollars—but because I was young and it was the first piece of art I’d ever bought, it seemed like a big deal. But there was another piece that went with it, and my sister said, ‘If you don’t buy that one as well, I’m going to buy it.’ So I bought the second one. I’m glad I did because they belong together.”

The Bailey was an introduction to his collecting philosophy: Trust your instincts and buy what you love, even if you think you can’t afford it. This realization did not fully crystallize, however, until he let a Jean-Michel Basquiat slip away—a decision he regretted for years. “The painting was a bit unusual for Basquiat,” Wayne recalls of the piece from 1984 he decided not to purchase because he thought it was too expensive. “Very simple, very plain. Just a few ovals, including one labeled ‘EGG.’ I liked it because the imagery felt raw, like he just felt it and didn’t worry about where everything was in the painting. I never forgot about it and I beat myself up because I hadn’t bought it.”

But then serendipity: Three years later when the woman who had bought the Basquiat decided to sell, Wayne decided to go for it, hang the cost. “I was just so happy to get that Basquiat,” he says. “Not because it was a Basquiat but because it was the one I had been thinking about all this time. And now it had come back to me. It was as if I’d messed up a relationship with a girlfriend who’d gone on to marry someone else, but now she was available again. I wasn’t going to let her get away twice.”

When Wayne considers adding to the collection, his most important consideration is not the artist or the work’s possible resale value but rather: Am I in love with this work? “If you can’t stop thinking about it,” he says, “and it haunts your dreams, then you need to do whatever it takes to make it happen.”