Bobby Smith | Upstage Comedy Lounge What do stand-up comedy, defensive driving school, Taco Bell, tax anxiety, and cheap hiking dates have in common? Bobby Smith, apparently. In this episode, Gail sits down with Bobby Smith, stand-up comic, comedy instructor, driving-school owner, and owner of San Antonio's Upstage Comedy Lounge, to talk about the strange collection of turns that built his career and the community that ultimately helped keep his comedy club alive. Bobby reveals that one of his earliest comedy training grounds was defensive driving school, where people with traffic tickets provided every comedian's dream: a captive audience that was legally required to stay. He also gets candid about the much less funny side of owning an independent comedy club: inventory, taxes, operating a bar, learning things the hard way, and the moment he was ready to close Upstage for good. Then something happened: the comedy community showed up. From there, Bobby and Gail tackle whether funny can actually be taught, why authenticity matters more than forcing a punchline, and what stand-ups and improvisers might learn from each other. Naturally, this eventually leads to hiking, dating economics, sparkling water, Taco Bell, Hawaiian escape plans, restaurant discoveries, wrinkled clothing... and Gail briefly comparing dating to buying real estate. As one does. 👀 What You'll Definitely Not See Coming: A comedy career launched with speeding tickets. Bobby's father employing an unconventional job-placement strategy. The financial realities of making people laugh while simultaneously selling them drinks. A surprisingly thoughtful stand-up vs. improv summit. The phrase "cheap date" taking Gail somewhere completely different. And rapid-fire questions that, once again, prove Gail does not fully understand the meaning of rapid-fire. About Bobby Smith Bobby Smith is a stand-up comedian, instructor, entrepreneur, and owner of Upstage Comedy Lounge in San Antonio, Texas. Through performing, teaching, producing, and running Upstage, Bobby has helped create a home for comedians while building connections across San Antonio's stand-up and improv communities. His approach to teaching focuses less on teaching people to be funny and more on helping performers become comfortable, authentic, and able to recognize the comedy already hiding inside their own stories. His philosophy? 👉 You can't teach somebody to be funny. But apparently, you can teach comedy to a room full of people who got speeding tickets. And sometimes, when running a comedy club becomes overwhelming and you're ready to lock the doors for good, your community reminds you why you opened them in the first place. If you want to yell at Gail, please email us at TheBITComedyNetwork@gmail.com "Billy Merritt's Improv Spotlight" is part of The BIT (Improv) Comedy Network. Visit www.BITComedyNetwork.com to listen to our other podcasts or apply to join the ensemble. CAST Gail: Hill Kane Bobby Smith: Himself MUSIC: "Shut Up Gail Theme" lyrics by Hill Kane, musical composition generated by Suno AI. "Zombie Clambake" performed by Little Kahunas | Produced by Peter Miller © | RIP buddy CREW Host, Producer, Director, Editor, Art, Co-Creator: Hill Kane Show Runner, Co-Creator: Billy Merritt Co-Creator: Paul Vato Production Assistance, Audio Production, & Graphic Art by Raising Kane Media + Marketing. Hosting Platform: Libsyn.com "The BIT," "The BIT (Improv) Comedy Network," "Billy Merritt's Improv Spotlight," and "Shut Up Gail" are Trademarks owned by Billy Merritt. ©2025-2026 Billy Merritt - All Rights Reserved Send inquiries + notices + requests: TheBitComedyNetwork@gmail.com
