Crying in Chili's – Details, episodes & analysis

Podcast details

Technical and general information from the podcast's RSS feed.

Crying in Chili's

Courtney Hill

Business

Comedy

Frequency: 1 episode/7d. Total Eps: 5

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 way, Crying in Chili’s feels like debriefing life with your smartest and funniest friends over chips, salsa, and a Presidente Margarita. Expect honest conversations, plot twists, guest interviews, emotional support disguised as comedy, and reminders that nobody really has it figured out.

Because sometimes rock bottom looks like a single tear falling into your Presidente Margarita.

Read moreCollapse

Site

RSS

Apple

Recent rankings

Latest chart positions across Apple Podcasts and Spotify rankings.

Apple Podcasts

🇬🇧 Great Britain - careers
22/06/2026
#87

Spotify

No recent rankings available

Shared links between episodes and podcasts

Links found in episode descriptions and other podcasts that share them.

See all

https://www.instagram.com/anthonycusumanocomedy
1 share
https://www.instagram.com/thepatiofarmer
1 share

RSS feed quality and score

Technical evaluation of the podcast's RSS feed quality and structure.

See all

RSS feed quality

To improve

Score global : 69%

Publication history

Monthly episode publishing history over the past years.

Year

Latest published episodes

Recent episodes with titles, durations, and descriptions.

See all

The Bees Left Me

Episode 5

Friday, June 19, 2026 • Duration 01:06:02

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 a business helping people grow their own food, spent time farming in Iceland and Pennsylvania, managed an urban farm, taught gardening classes, launched a podcast, and somehow still finds time to dream about writing books.

Together, they talk about entrepreneurship, side hustles, social media, following unconventional career paths, and why sometimes the best thing you can do is start before you're ready. They also discuss the power of kindness, the reality of running your own business, crying in yoga classes, and the surprisingly emotional journey of trying to keep bees.

If you've been waiting for a sign to start the thing you've been dreaming about, this might be it.

Connect with Erin:

Website: thepatiofarmer.com

Instagram: @thepatiofarmer

Read moreCollapse

Episode 4: Kindness Is a Career Strategy

Episode 4

Friday, June 12, 2026 • Duration 50:39

After layoffs, rejection emails, and sending resumes into the void, sometimes the most valuable thing you have isn't your resume—it's your reputation.

This week, Courtney sits down with former coworker and creative leader Jay Peine to talk about navigating today's job market, building confidence during uncertain seasons, and launching something new when the traditional path isn't working.

Together, they discuss the realities of job hunting in an AI-driven world, the importance of networking, and why genuine relationships still open more doors than any algorithm ever will. Jay shares the story behind launching Open Mind Creative, while Courtney reflects on career pivots, personal branding, and what it means to bet on yourself when the future feels uncertain.

They also somehow end up talking about shark teeth, Amelia Island, remote work cats, and main-character energy in airport terminals.

If you've ever felt stuck, discouraged, or unsure of what's next, this episode is a reminder that kindness isn't just a personality trait—it's a career strategy.

Connect with Jay Peine:

Read moreCollapse

Episode 3: Rejection, Redirection & Buff Jesus

Episode 3

Friday, June 5, 2026 • Duration 55:43

Episode 3: Rejection, Redirection & Buff Jesus

What do layoffs, comedy, job searching, and a ripped version of Jesus have in common?

This week on Crying in Chili's, Courtney sits down with comedian, writer, and former coworker Anthony Cusumano to talk about rejection, redirection, and what happens when life forces you to rethink the path you thought you were on.

From navigating layoffs and today's chaotic job market to pursuing creative dreams outside of corporate America, Anthony shares how he's balancing freelance work, comedy, and his latest creative project: Buff Jesus—a comedy short film about a conservative priest, a queer graffiti artist, and an unexpectedly effective piece of church marketing.

Along the way, Courtney and Anthony swap interview horror stories, discuss why personality still matters in hiring, debate whether anyone actually enjoys Applebee's, and explore the idea that sometimes rejection isn't a dead end—it's simply redirection toward something better.

Whether you're job hunting, chasing a creative dream, questioning your career path, or just here to find out why Buff Jesus exists, this episode is for you.

In this episode:

Navigating layoffs and career uncertainty
The realities of today's job market
Why rejection isn't always a bad thing
Recruiter and interview horror stories
Anthony's original musical
The story behind Buff Jesus
Why Chili's will always beat Applebee's

Guest: Anthony Cusumano
Comedian, writer, performer, and creator based in Chicago.

Follow Anthony on Instagram

Episode 2: Do The Damn Thing

Episode 2

Friday, May 29, 2026 • Duration 01:09:45

Episode 2: Do The Damn Thing

Courtney is joined by former coworker and creative powerhouse Amanda Duncan for a conversation about layoffs, burnout, freelancing, music, and figuring out who you are when your job title disappears.

From corporate chaos to creative dreams, they discuss perfectionism, trusting your instincts, crying in public, and why sometimes the best plan is to stop waiting and just do the damn thing.

Grab your chips and salsa. The emotional debrief is now in session.

Connect with Amanda:

Read moreCollapse

Episode 1: Q2 Chaos

Episode 1

Friday, May 22, 2026 • Duration 55:37

Most of us are just trying to survive the chaos — whether it’s a breakup, a layoff, or a broken foot — and somehow laugh through the mess. In the very first episode of Crying in Chili’s, Courtney and her forever bestie Vickie unpack the absolute rollercoaster that has been Courtney’s Q2 of 2026: losing her job, breaking her foot, moving apartments, spiraling over health insurance, and questioning if the universe has personally put her on a character-building subscription plan.

Through laughter, emotional damage, and a few too many “you genuinely cannot make this up” moments, they talk about the reality of layoffs, the chaos of adulthood, Sabrina Carpenter, friendship, vulnerability, and why sometimes the only thing you can do is laugh before you cry again.

If you’re tired of the polished version of adulthood and craving honest conversations with a side of humor, this episode is for you. Because sometimes rock bottom looks like a single tear falling into your Presidente Margarita.

Read moreCollapse

Crying in Chili's – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

RSS feed quality and score

Publication history

Latest published episodes

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Crying in Chili's – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other4

Instagram4

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Other4

Instagram4

Youtube1