Preston Oshita (a.k.a. Towkio) may be on the fast track to rap stardom, but even rising stars can hit a stray bump. On the night before we were to meet near his West Town apartment, the 24-year-old—whose major-label debut, WWW., drops on Rick Rubin’s American Recordings this fall—found himself on the side of Sunset Boulevard in Hollywood, suitcase in hand. He’d hopped out of his girlfriend’s car after she’d found incriminating texts on his phone. “I just had to laugh,” says Oshita. “Here I am, putting in all this energy, and I’m left in the street with my fucking bag.”

Oshita is no stranger to forging his own path. By the time he was a senior at Lane Tech, he had a tidy nest egg from selling weed to the high school’s 4,000-some students—enough that when, at 19, he got serious about rapping, he could spend $6,000 on a management team.

The investment paid off. On the strength of Oshita’s 2015 single “Heaven Only Knows,” Rubin invited him to his Malibu studio Shangri-La, where Bob Dylan and Eric Clapton famously sought inspiration. The setting, which Oshita calls “magical,” made for a spiritual, sprawling album, teetering between jagged club bangers and trippy Auto-Tuned ballads. Rubin pulled out some stops, too. “One night at, like, 11 o’clock, he just drove up in a big-ass Tesla with [R&B singer] SZA,” says Oshita. “We hung out until 2 a.m. and cut the song ‘Morning View’ for the record.”

But such intoxicating L.A. adventures won’t pull Oshita from his hometown. “I’m a product of Chicago. My dad’s parents met in [a Japanese] internment camp, then moved here. My mom came to 18th and Western from Mexico. I’m going to build a skyscraper here, and people will love me for the rest of Chicago’s history.”