Episode 45: Olivia May

Main Street Moxie

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Olivia finds and expresses her moxie through stand-up comedy. In this episode, Olivia explores how she grew her comedy moxie, describes her comedic process, and reflects on the challenges of leaving a highly structured, results-oriented career to dive into the unpredictable world of stand-up comedy.
Olivia started her comic explorations by testing the waters at countless open mics in New York City before moving to Charlotte, NC, for her corporate job and continuing her comedy journey there. While in Charlotte, she founded Olivia’s Fun and Flirty Comedy Show, a monthly stand-up show at a trendy brewery, which she grew in popularity over the course of two years.
A standout performer, Olivia was also selected for 2023’s North Carolina Comedy Festival, showcasing her growing talent and dedication to the craft.
While planning shows and booking comics for that show, she also worked her day job assessing bank risk. Then, she took a risk of her own. In March of 2024, she took a considerable leap of faith. Quitting her bank role, she set out for Chicago to launch herself full-time in comedy–and has not looked back.
Olivia is now a Chicago-based comedian, building her comic material and show appearances. Known for her sharp wit and relatable humor, Olivia has graced stages at notable venues, including the Laugh Factory Comedy Club, Lincoln Lodge Comedy Club, and Red Room Comedy Club. She regularly attends open mics and has begun taking improv classes at Second City, expanding her repertoire and range.
She was recently selected from over 100 comedians who auditioned to perform at the Vouch Comedy Show at the Laugh Factory. In The Windy City, she continues to captivate audiences with her unique perspective and comedic flair.
This episode of Main Street Moxie was proudly sponsored by Main Street Magazine.

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