​

Hey y’all,
 

I wanted to take a second to lay out what Pearl St Comedy is all about and why I’m doing this.

Comedy has been a part of my life for over 15 years. But until now, it’s always been something I had to fit in between work and raising my sons. Now? I’m all in. And I’m not just here to produce shows—I’m here to build something that actually makes a difference in Richmond’s comedy scene.

​

For too long, there hasn’t been a real hub for comics in this city. When I was coming up, there was no clear path—no writing sessions, no workshops, no resources on how to get booked, how much to charge, or how to navigate this industry. It was just go figure it out. I don’t want the next generation of comedians to have to stumble through that.
I want to change the game.

​

What Pearl St Comedy Stands For

​

• A Place for ALL Comedians – Whether you’re just getting started, grinding in the local scene, or a seasoned pro, Pearl St Comedy is here for you. Performers, producers, writers—if you're serious about comedy, I want to create opportunities for you.
   

• Building a Stronger Comedy Scene – I want to make Richmond a city where comedians aren’t just performing—they’re thriving. That means more stage time, more mentorship, and more collaboration.
   

• Fairness & Professionalism – Comedy should be fun, but it should also be fair and professional. I believe in fair pay for comedians, making sure entertainers are treated right, and creating a great experience for both the comics and the audience.
   

• Growth & Support – If you want to get better, Pearl St Comedy is here to help. From learning how to run a show to understanding the business side of comedy, I want to shorten the learning curve for comedians who are serious about this craft.
  ​

This Isn’t My First Rodeo
 

I’ve been making things happen in this scene for years. In 2009, I produced Richmond’s first known comedy festival, the F*Bomb Comedy Festival, featuring Whitney Cummings, Jon Reep, and Doug Stanhope—with Jim Beam as a sponsor. I’ve produced Buckin’ Comedy Throwdown since 2009, the ROFL Comedy Series at Atlas 42, Comedy at The Perk in partnership with the Perkinson Center, and shows at venues across Richmond, Charlottesville, and beyond. Pearl St Comedy even has a dedicated seat in the Jimmy Dean Theater—that’s how deep this goes.
 

I’ve worked with and booked incredible comics like Lynne Koplitz, Carmen Lynch, Louis Katz, Jared Logan, Nick Vatterott, Erin Jackson, Hampton Yount, and Big Al Goodwin. I’ve also had the privilege of opening for Guy Torry, Tony Rock, Chris Porter, Josh Blue, Bill Bellamy, Nikki Glaser, Godfrey, Dave Landau, and a ton of others.
 

I understand both the business and creative sides of this industry. Thanks to my background in corporate sales and marketing, I know how to negotiate, set terms, create opportunities, and develop processes that actually work. This isn’t just about putting on shows—it’s about building something real that benefits comics, venues, and audiences alike.

​

Why This Matters to Me
 

This isn’t just about comedy—it’s about chasing dreams. I lost my corporate job after 10 years, and instead of letting that define me, I saw it as a sign to bet on myself. I want to build something that lasts—something that actually makes a difference for comedians in Richmond.

I also want my two sons to see what it looks like when you go all in on something you love.
You don’t wait. You build. You create. You make it happen.
 

Join Me in This Mission
 

This isn’t just about me—it’s about all of us. I want Richmond to be known as a city where comedians aren’t just performing—they’re growing, connecting, and thriving. If you’re a comedian looking to get better, get booked, or just be part of something bigger, I want you to know: Pearl St Comedy is here for you.
 

Let’s make something great. Together.
 

Kenny Wingle
Founder, Pearl St Comedy

PearlStComedy@gmail.com
www.PearlStComedy.com