SITB 251 - Connection Beats Perfection w/ Wes Berger

What this episode covers

He built a 10,000-person Santa-themed party… and that’s not even the craziest thing he’s done in the music industry. Today on SITB, Wes Berger—San Diego entrepreneur, event producer, and all-around legend—shares how he went from Chicagoland kid to running some of the wildest events in SoCal… and the insane stories that came with it.This San Diego-based entrepreneur, talent buyer, label manager, event producer—and all-around solid dude— is a true legend. This guy’s done it all behind the scenes: from Santacon to Freedom Fest to Daisy Chain and Subsessions, Wes has built brands that pull serious crowds.He’s originally from Chicagoland, and in this episode he shares how he took a massive leap to the West Coast, the wins, the struggles, and some crazy industry stories along the way.You’ll also catch the dynamic between us—we’re longtime friends, which means plenty of roasting, plenty of laughs, and a lot of genuine insight into what it takes to thrive in this business.

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Frequently Asked Questions

How long is this episode of Sherm In The Booth?

This episode is 2 hours and 20 minutes long.

When was this Sherm In The Booth episode published?

This episode was published on August 20, 2025.

What is this episode about?

He built a 10,000-person Santa-themed party… and that’s not even the craziest thing he’s done in the music industry. Today on SITB, Wes Berger—San Diego entrepreneur, event producer, and all-around legend—shares how he went from Chicagoland kid to...

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