In Part 2, we pick up where we left off in Part 1. Dregs shares the story of the day he started doing graffiti. It was also when he began experimenting with rapping.

Dregs talks about all the "cool shit in The City" back then, the early 2000s. From sports and music to the aforementioned underworld of San Francisco, SF was lit. It was a time when you could simply step outside your home and find something or someone or some people. You could take a random Muni ride and let stuff happen. And it happened all over town, with creativity pouring out of so many corners. For Dregs, tagging happened first.

He started hanging out more in The Sunset, which was quieter than his own hood. He and his buddies would tag, hang out in the park with their boomboxes, drink 40s, and freestyle. One of those buddies had a computer audio-editing program and a cheap mic (RIP Radio Shack). That friend sent him a track over AIM and it blew young Dregs away. Then he learned that two other guys wanted to battle. Dregs hopped on a bus to Lawton Park to join in. It was his first rap battle.

The crew that battled that day ended up uniting and making more and more music together. They formed a tagging crew called GMC (Gas Mask Colony), which didn't last long as as a tagging crew, but they kept the name for their rap group. But the group splintered. As mentioned, Dregs ended up at ISA in Potrero. He got into a DJ program and honed his skills. Soon, it was time to get into a studio to lay down some tracks.

They recorded their first song and people liked it. The crew of four included several different ethnicities and neighborhoods across San Francisco, so they had widespread reach.

We take a sidebar to discuss how Dregs got his name. It's a story that involves the movie Scarface.

Because of time, I ask Dregs to walk us quickly through the years between getting underway with hip-hop and starting his show, History of The Bay. He did music with his GMC posse as well as some solo projects. Days of hanging out and drinking 40s gave way to adult-life realities—jobs and such. They hadn't figured out a way to make money off their art. Dregs went to City College and then spent two years at UC Riverside. He came back and worked as a youth counselor in the Tenderloin.

At another job in TL, a woman in supportive housing where Dregs worked had a psychotic breakdown. He was the only employee around, and even though he was about to leave for the day, he helped her out. The next day, a boss type thanked Dregs, but told him he'd never get properly compensated for what he did until or unless he had a bachelor's degree. And so he enrolled at SF State.

He was in his late-twenties at this point, and did better in school than he had ever done. He was a straight-A student, in fact. He took a heavy courseload. It was the first time he'd had Black teachers. One of them advised Dregs to go to graduate school. He looked through the graduate-level programs available and decided that law was his best fit.

And so off he went, to law school in Davis. He did well at this level, also. He graduated, passed the California bar, and got hired by a firm. He was making good money and thought about saying good-bye to making music. But then the folks he worked with at the law firm convinced him not to.

One of the first cuts he did in that era was a collaboration with Andre Nikatina called "Fog Mode." When the song dropped, it was the pandemic. Dregs had been doing his law work from home. It "sucked," he tells me. But the track took on a life of its own. He realized amid it all that it was time to go for it with his art.

One of the first steps was to get his social media ramped up. Some people suggested TikTok, but Dregs wasn't sure what content to throw up on that app. Others said, "Talk about you, talk about your interests." He looked around and realized that no one out there was really talking about the SF/Bay hip-hop Dregs grew up on, or the prolific taggers he ran with. Around this time, in December 2021, his dad passed away. In the early stages of his grief, Dregs figured it was once again time to quit art and turn his energy and attention to taking care of his mom. But then something happened, something that some of us who've experienced loss can possibly relate to. In March 2022, Dregs launched History of The Bay on TikTok.

With his music and social media popping, his law work took a back seat. Folks in his firm took notice and laid Dregs off. It was for the best.

Find Dregs online at his website or on social media @dregs_one. Get History of The Bay on any podcast app.

We end the podcast with Dregs' take on our theme this season—keep it local.