
Welcome to Crying in Chili’s — the podcast for anyone currently experiencing a character-building season against their will.
Hosted by Courtney Hill, this show dives into career chaos, layoffs, relationship drama, life pivots, bad decisions, quarter-life crises, and all the messy in-between moments that somehow become funny later.
Equal parts vulnerable, witty, and unhinged in the most relatable... more
| Publishes | Weekly | Episodes | 12 | Founded | 3 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | CareersBusinessComedy | |||

Episode 12: Side Hustle or Cry for Help?
This week, Kate Clark is back, and we're asking the question every underemployed millennial has secretly asked themselves:
"Could this be a business?"
From Rover, DoorDash, and Facebook Marketplace to becom... more
Episode 11: Please Perceive Me Being Whimsical
What if the cure for adulthood is letting yourself be a little weirder?
This week, Sarah Weygandt returns to Crying in Chili's for a conversation about whimsical hobbies, emotional support deer, shark ... more
Episode 10: The Shed, the Bullfrog, & the Margaritas
This week I'm recording from what might be the greatest podcast studio we've ever had...my friend Colin's Chili's-themed shed.
Yes, you read that correctly.
What starts as a conversation about o... more
Episode 9: Unfuckwithable: Turning Pain Into Purpose
What happens when life forces you to stop, rebuild from the ground up, and figure out who you are on the other side?
This week, Courtney sits down with her former coworker and friend Sarah Weygan... more
Episode 8: The Story Behind Crying in Chili's
This week, you're getting something a little different.
When a last-minute guest cancellation left an unexpected opening in the schedule, Courtney decided it was finally time to answer one of the questi... more
Episode 7: You Can Always Change Your Mind
This week, Courtney sits down with spin instructor, fitness coach, and "curator of experiences", Kate Clark.
Kate shares the unexpected story of walking away from law school to pursue a career in fitness, ... more
Episode 6: Approach Life With A Plum
Bonus episode alert! We've been recording so many great conversations lately that I couldn't wait until next week to share this one.
This week, Courtney is joined by longtime friend Caroline Pearson for a conver... more
Episode 5: The Bees Left Me
This week, Courtney sits down with longtime family friend and entrepreneur Erin Hostetler, founder of The Patio Farmer.
Unlike many recent Crying in Chili's guests, Erin never took the corporate route. Instead, she built... more
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Recent interactions between the hosts and their guests.
Listeners, social reach, demographics and more for this podcast.
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The show centers on personal growth through career pivots, layoffs, entrepreneurship, and life's chaotic moments, anchored by candid storytelling and humor from two longtime friends. Across recent episodes, listeners hear practical resilience tips, behind-the-scenes of building brands and creative projects, and relatable chronicles of navigating professional setbacks with curiosity, empathy, and humor. A notable angle is the emphasis on culture, community, and authentic self-trust—often with personal anecdotes about studio life, side ventures, and pivoting toward meaningful work—making it appealing to anyone facing changes in work or life and seeking encouragement with a light, witty touch.
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Crying in Chili's launched 3 months ago and published 12 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on Crying in Chili's include:
1. Kate Clark
2. Sarah Weygandt
3. Erin Hostetler
4. Jay Peine
5. Anthony Cusumano
6. Amanda Duncan
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