Episode 33: Richie- Making the Best of How Things Work Out

This episode is unhinged in the best way. Jimmy and Breezy were OUT OF CONTROL, and Richie—well, Richie kept up like the seasoned vet he is. With 24 years sober, Richie brings us a rollercoaster of a story that starts with eviction on day three and somehow lands in grace, humility, and Pop-Tarts.

Richie got sober at 21, after years of burning every bridge—including the one with his mom, who finally said, “I hope you fall hard enough to bounce back.” And fall he did… onto a cat-hair-covered cot in someone’s hallway. What came next sounds like a movie: a chance encounter with a celebrity who showed him trust when he’d never trusted himself, a Pop-Tart that became a symbol of hope, and the slow, painful process of becoming a person who could show up.

From baking cakes for meetings with his mom (because he couldn’t afford one) to navigating heartbreak and trauma, Richie shares what it looked like to build a new life from nothing. He opens up about the relationship that changed him—and the devastating loss that nearly broke him. He talks about being a feral animal who learned how to clock in, clean toilets, and show up when it mattered. Working at Starbucks became spiritual—because for the first time, people countedon him.

Now, 24 years later, Richie reflects on getting back to basics, checking in with his trusted crew, and trying to live by one of his favorite quotes:

“Things work out best for people who make the best of how things work out.”

He’s still learning, still laughing, and still letting himself be human.
“I’m always me—but I’m not always one way. And I like the flow of that.”

🎧 Buckle up for a wild, hilarious, and deeply moving conversation with someone who’s done the work—and lived to tell the tale.