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.
Social Media
Instagram @oliviahmay_
TikTok @oliviahmay_
Popular Podcasts
Bookmarked by Reese's Book Club
Welcome to Bookmarked by Reese’s Book Club — the podcast where great stories, bold women, and irresistible conversations collide! Hosted by award-winning journalist Danielle Robay, each week new episodes balance thoughtful literary insight with the fervor of buzzy book trends, pop culture and more. Bookmarked brings together celebrities, tastemakers, influencers and authors from Reese's Book Club and beyond to share stories that transcend the page. Pull up a chair. You’re not just listening — you’re part of the conversation.
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com