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.

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.

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

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

Expanded Reality TV is a podcast where improv comedians create absurd audio performances based on behind-the-scenes stories of real reality television stars, building new weird worlds from the things that people don't see when watching their favorite reality tv shows.

Episode #1 features an interview with Ed Popil aka Mrs. Kasha Davis, a professional drag queen and two-time contestant on the reality television show RuPaul's Drag Race! Inspired by Mrs. Kasha Davis' interview, our ensemble took us into a deep dive into telecom romance, a movement of 55 year old men performing in children's musicals, hotel staff tackling quarantined reality tv stars, emotionally moving weather women, extreme office gossip gangs, producer overreach and so much more.

Host: Angela Washko
Special Guest: Mrs. Kasha Davis
Improv Comedy Ensemble: Luke Bovard, Jim Tripp, Katya Vasilaky, Angela Washko

Theme Song Composer: Jesse Stiles

Bit Comedy Network Director & Founder: Billy Merritt
Bit Comedy Network Producer: Hill Kane

(c) 2026 Billy Merritt | All Rights Reserved

What happens when a reverend starts a podcast dedicated to listening to "sinful music" so you don't have to?

Complications.

In this episode, Gail sits down with the very reverend Justice Smythe, chairman of the River Creek Family Values Coalition, minister, moral watchdog, and host of the short-lived podcast Samples of Sin, where he reviewed music he believed decent people should avoid.

Justice's philosophy?

👉 Sometimes you must confront temptation… for research purposes.

Also:

👉 Apparently six episodes were enough.

Together, Gail and Justice unpack the mysterious end of Samples of Sin, the emotional hazards of "investigating" sinful artists, and why some music started raising questions Justice may not have been prepared to answer.

There are conversations about marriage. There are discussions about performance, honesty, suspiciously fashionable clothing, and the dangers of spending too much time reflecting at "the manhole."

There is a rapid-fire round that becomes increasingly concerning.

👀 What You'll Definitely Not See Coming:
A personal trainer named Pete.
A conversation that gets unexpectedly personal.
And a moment where Gail may or may not push things… too far.

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
Justice Smythe: Konrad Andrew
Billy Merritt: Himself

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