Homeless Yale Grad Whose Story Made News Is Off the Streets with the Help of an Old Acquaintance

Shawn Pleasants says he wants to use his raised profile to advocate for a resource center for L.A.’s unhoused

After graduating from Yale, banking on Wall Street, and amassing a small fortune as an entrepreneur in the 1990s porn DVD boom, Shawn Pleasants had spent ten years living on the streets of Koreatown due to depression and a meth habit when CNN did a feature on him in September.

One of the millions of people who saw the story was Kim Hershman, a Hollywood entertainment lawyer and fellow Yalie who sought out Pleasants’ Koreatown encampment to see is she could help him get a new lease on life.

“My big thing was: ‘What do you want? And based on what you want, I’m going to do whatever I can to help you,'” she recalls telling Pleasants when they first met.

“I want to make a difference,” Pleasants replied. “I’m in this situation, and there has to be a reason for it all, and I want to help others.”

Pleasants envisioned starting a resource center for the neighborhood’s homeless where they could meet basic needs like charging phones, bathing, and cleaning their clothes, free from the strident rules and physical danger found in traditional shelters. He expressed the same sentiment in September, when Donald Trump was in L.A. proposing a “crackdown” on homelessness that would include herding people into massive government facilities.

“We need places to shower, if you don’t want us to have hygiene issues. And in order to get a job, we need to have clean clothes. Where do I iron? How do I keep them pressed?” he said at the time. “The idea that we’re going to force people into a facility that’s probably located in a very remote area is not a solution. That’s not going to connect people to jobs, to housing, to services (like) mental health and addiction treatment.”

Now, with Hershman footing a bill that could run over $10,000, Pleasants is going to get addiction treatment himself to deal with a meth problem that predates his homelessness. Hershman arranged for Pleasants and his husband to move into the guesthouse of an L.A. estate, and as part of the bargain he’s agreed to check himself into a rehab facility in Tarzana.

“I’m ready,” Pleasants says, while admitting that he feels “felt somewhat anxious” but adds that, “it feels like the responsible thing to do.”

Though Hershman—who’s been taping her journey with Pleasants with an eye toward developing a docuseries—says she’s received many offers of financial assistance through Yale alumni groups on social media, nothing has been formalized so far.

Pleasants recently obtained a Section 8 voucher for federal housing assistance and Hershman is helping him and his husband search out more permanent accommodations than that of guests in someone else’s home.

Pleasants says that while he and Hershman are discussing ways that they might bring his dreams of a resource center to fruition, he’s still having trouble acclimating himself to his new life, and that he knows people are watching to see if he’ll blow this second chance.

“I hope the hell not,” he says. “And I hope for their sake that they don’t lose their footing because they’ll experience some of the worst times that I experienced. And it doesn’t matter who you are, it’s a possibility.”

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