Skip to content
Flirting With Failure podcast artwork

PODCAST · comedy

Flirting With Failure

by Addison Brown

My name is Addison Brown and I think your mistakes are sexy. In each 30-minute episode, I interview a different sensational person about their stories of success through a lens of past faults. From careers to relationships to family to introspection, we all screw up once in a while. The question is, are you ready to give in and flirt with your failure?www.patreon.com/flirtingwithfailurepod

Publisher-supplied feed metadata · PodParley refreshed May 31, 2025 · Source feed

Episodes

  1. The Skill of Acquiring Skills

    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…

    more
  2. Djibouti ---> Chicago

    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.

  3. Season 2 Premiere- The Wine Coach w/ LaVonda Wagner

    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…

    more
  4. The Opera Came First

    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…

    more
  5. Make The Ice Man Cry

    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...

  6. The Mayor of Poetry Town

    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...

  7. Little Failures Every Day

    Alexis Nido-Russo, CEO and Founder of Local Eclectic Jewelry, refers to herself a creative person who also happens to be great at business and I couldn't agree with that more. 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...

  8. Where Do The Girls Go At Night?

    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…

    more
  9. Fuck That Guy

    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…

    more
  10. Dancing Robots

    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…

    more
  11. Waiting For Yes

    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.

  12. Filling Out The TPS Report

    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....

Type above to search every episode's transcript for a word or phrase. Matches are scoped to this podcast.

Searching…

We're indexing this podcast's transcripts for the first time — this can take a minute or two. We'll show results as soon as they're ready.

No matches for "" in this podcast's transcripts.

Showing of matches

No topics indexed yet for this podcast.

Loading reviews...

ABOUT THIS SHOW

My name is Addison Brown and I think your mistakes are sexy. In each 30-minute episode, I interview a different sensational person about their stories of success through a lens of past faults. From careers to relationships to family to introspection, we all screw up once in a while. The question is, are you ready to give in and flirt with your failure?www.patreon.com/flirtingwithfailurepod

HOSTED BY

Addison Brown

CATEGORIES

Frequently Asked Questions

How many episodes does Flirting With Failure have?

Flirting With Failure currently has 12 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Flirting With Failure about?

My name is Addison Brown and I think your mistakes are sexy. In each 30-minute episode, I interview a different sensational person about their stories of success through a lens of past faults. From careers to relationships to family to introspection, we all screw up once in a while. The question...

How often does Flirting With Failure release new episodes?

Flirting With Failure has 12 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Flirting With Failure?

You can listen to Flirting With Failure on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Flirting With Failure?

Flirting With Failure is created and hosted by Addison Brown.
URL copied to clipboard!