Jordan Holmes, aka Dxtr Spits, is a modern day Renaissance man. Prospering as an engineer, musician, entrepreneur, and spoken word artist, Jordan's relationship with failure and success is spread amongst his many crafts. He offers some real insight on how to manage multiple projects from different industries, the beauty of the overlap of science and the arts, and building up a sense of humor around your mistakes. 

Jonah Saesan is an actor, improviser, teacher at the Second City, father, husband, and veteran. In this episode, we talk about TikTok fame, improv, and Jonah's unique journey through the Marine Corps to a career in the arts. 

For two decades, LaVonda Wagner was living her dream as a women’s basketball coach. When that dream came to a screeching halt, she turned to what many people turn to when the going gets tough: wine (but not in the way you may think.) Now a certified level two sommelier, LaVonda joined me on the pod to share her story of loss, perseverance, and redemption from the basketball courts all the way to the vineyards of Italy. 

In the season one FINALE of Flirting With Failure, I had the pleasure of interviewing Chicago-based opera artist Will Liverman. On top of having a voice that sounds like liquid gold, Will is also a complete delight to chat with and learn from. He was kind enough to share with me his journey through the opera world: where his interest in the art form began, what it was like attending arguably the most famous performing arts college in the world, the ups and downs of transitioning into being a...

Todd McNerney is a Professor of Theatre and Associate Dean at the College of Charleston. He is also a director, a certified goofball, and  responsible for giving some of the best and most memorable inspirational speeches and pep talks I've ever witnessed. I knew I had to get Todd on the podcast to share some of his famous infinite wisdom that anyone who has been taught or directed by him is familiar with. Todd shares stories of himself as a young theater student, his time as a tour manager...

Mighty Mike McGee is a poet, a humorist, an exceptional friend, and the former Poet Laureate of Santa Clara County (among other things.) His profound love of words, art, and human connection pours out of him and fills up every crevice in every conversation you have with him. In this particular conversation, Mike tells us what it's like to be the Poet Laureate, how achieving a lifelong dream of touring changed his life in surprising ways, and reminds us that we are simply doing the best we...

Alexis Nido-Russo, CEO and Founder of Local Eclectic Jewelry, refers to herself a creative person who also happens to be great at business. She went from a degree in Fine Arts, to a temp job, to touring with Miley Cyrus (yes, you read that right), to a booming online jewelry shop with almost 800k Instagram followers. Every step on the way to where she is now was more surprising than the last, but one thing never changed- she was willing to put in the work. Truly delightful and inspiring,...

This week, I had the pleasure of listening to comedian Allison Reese-Shapiro tell me about some of her blunders in the comedy world, both on and offstage. From working at a Starbucks in West Hollywood, to understudying on The Second City ETC Stage in Chicago with only a few hours notice, to touring across the country and staying in questionable hotels, Allison has been around the block in the not-so-extravagant world of comedy and her tales of the mishaps along the way provided a much-needed...

Hannah Wicklund graduated from our small town high school two years early to pursue her dreams of becoming a musician and BOY OH BOY did she do the damn thing. Hannah has toured both nationally and internationally, performing among the likes of such legends as Tom Petty, The Red Hot Chili Peppers, Jackson Brown, and more. She talks with me about what it's like to thrust yourself into being a full-time rockstar at such a young age, the drawbacks behind being a young woman playing music venues...

Ishaan Pakrasi is a consultant at Ernst & Young by day.... but a dancing robot engineer by night. In this episode, Ishaan fills me in on a unique world that combines art + engineering, tells me all about the time he recorded a podcast with some of the most famous people in India and decided not to release it (!!!), and shares his perspective on what it's like to want the liberty to keep failing in a country that won't let you. 

Arlene Malinowski, storyteller extraordinaire and certified queen of the solo show, talks with me about growing up as a hearing child in a deaf household, a mid-life career change, and the agony of reading your first bad review. 

This week I talk with start-up guru Jim Phillips (Co-Founder of Fooda and former head of the Ritual App in Chicago) about risking it all in the start-up world, picking yourself back up from job loss in the pandemic, and where you go when you find out that your business idea already exists. Disclaimer: I still don't know what Jim's job actually is, but boy did we have fun talking about it. 

Caleb Hiltunen, lead singer of alt rock band 'Friday Pilots Club' tells us what it's like to be a young, successful, and impressionable rockstar with Type 1 Diabetes. Oh, and incase you hadn't heard, we went to middle school together.