Leonard Cohen: La Esquina, Free Parking & the Future of Downtown SLO | Up+Adam

Sponsored by The Mountain Air | Sponsored by Benny’s Pizza | SLOFreeParking 

Downtown San Luis Obispo has its characters. Its storytellers. Its lifers. And then there’s Leonard Cohen.

On this episode of Up+Adam, Adam sits down with the longtime restaurateur behindLa Esquina Taqueria, Cioppino’s, and the legendary Old Port Inn for one of those conversations that only happens when two people genuinely love where they live.

This episode starts with tacos and free parking… then spirals beautifully into the history of Port San Luis, the psychology of hospitality, modern tipping culture, World War II storytelling, hidden Central Coast history, and the surprisingly emotional origin story behind those iconic glass tables over the water at Old Port Inn.

Leonard opens up about the brutal impact downtown parking issues had on local businesses over the last few years and why he decided to offer free parking at La Esquina to help bring people back downtown. He also talks about the upcoming release of his new memoir and recipe collection, By The Glass, which blends family stories, restaurant history, recipes, local lore, and the experiences that shaped his life as a businessman, father, community advocate, and accidental historian.

You’ll also hear:

• Why Leonard believes hospitality should feel generous, not restrictive

• His brutally honest take on modern tipping culture

• The return of beloved Cioppino Nights

• How a childhood memory with his dad inspired a dining experience locals still talk about decades later

• The behind-the-scenes role he quietly played during the Unocal years in Avila Beach

• The unbelievable true story inspiring his next World War II-based novel

• What happened when the real Leonard Cohen called the restaurant from Australia

This is one of those deeply local conversations that somehow becomes universal. Funny, opinionated, nostalgic, thoughtful, and wildly SLO CAL.

 • Check out Restaurant:La Esquina Taqueria

• Cioppino Nights return regularly at La Esquina (5/31 next one)

• Free parking available in the new downtown parking structure when dining at La Esquina

 • Follow on Instagram: @laesquinaslo

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