The doormat outside Flom's apartment on the 67th floor of a Midtown Manhattan highrise stands out with big, black letters: "OH SHIT NOT YOU AGAIN."

Inside, floor-to-ceiling windows let the natural light flood in, even on a foggy Friday afternoon, with views of the Hudson River to the west and Central Park to the north. Colorful art hangs on the walls: a framed poster of Darth Vader standing in the ocean, filling a Brita filter; an enlarged version of an iconic Marilyn Monroe photo in pink hues; a series of newspaper clippings about LGBTQ rights, set behind dozens of repurposed eyeglass lenses. Kitschy art featuring Lifesavers and Brillo flanks each end of the living room couch, where Flom sits beneath a large painting that says, "EVERYTHING IS GOING TO BE AMAZING."

Lulu, Flom's four-year-old English bulldog, barks and walks around the apartment like she owns it.

"When I was a kid, I wanted to be a rock star, if you want to go back that far," Flom says after I ask him about how he entered the music industry. He peers at me behind dark tortoise glasses, wearing a black Guns N' Roses T-shirt with strategically cut holes underneath a black blazer.

"My dad was legendary corporate lawyer Joe Flom, and my mother graduated Cornell when she was 18," he says. "So, the idea that I wanted to go to college wasn't big. I was basically wearing my guitar around all day, every day, and just practicing a lot and performing a little."

Flom's late father, a partner at what is now Skadden, Arps, Slate, Meagher & Flom (one of the country's largest law firms), had made a deal with him: become a rockstar within one year, or go to college. His mom vetoed the deal immediately, saying he either needed to go to school or get a job. So his dad made a few phone calls and got him a job interview at Warner Communications.