Jared Klickstein joins the Perry Podcast.

He grew up with heroin-addicted parents, spent a decade homeless shooting dope on Skid Row and the streets of San Francisco, hustled and stole to survive, and eventually landed in LA County Jail. Inside, he navigated prison politics, racial rules, and even turned kosher meals into a small hustle.

After hitting rock bottom through blackouts, serious injury, and forced withdrawal behind bars, Jared got clean. He is now seven years sober, a law student in Chicago, and the author of Crooked Smile: What It Took to Escape a Decade of Homelessness, Addiction, and Crime.

Perry and Jared talk about why “harm reduction” often keeps people trapped, how jail actually works versus how it’s portrayed, what really pulls someone out of addiction, and why some cities collapse while others survive bad leadership. The conversation drifts into Chicago versus San Francisco, migrant policy, crime, prison hierarchy, and the difference between managed decay and real recovery.

Grab Crooked Smile on Amazon (or DM Jared for a free PDF if you're broke).