March 9, 2023
Money, Jokes, and Real Talk: A Comedic Spin on Our Relationship with Money

In this special episode, Darrin flips the script and invites not one but two guests — up-and-coming comedians Don Sombra and JK the Laughing Stoic — for a hilarious, thought-provoking conversation about our relationship with money.
This episode is packed with laughs, jokes, and real talk as the trio dive into money topics like:
H
ow upbringing shapes financial habits
Gender roles and money dynamics
The crazy things people might do for a big payday
It’s an episode that proves financial conversations don’t have to be boring — they can be funny, relatable, and still hit home.
In this episode, you’ll hear:
- Don and JK share their personal (and comedic) outlooks on money
- How humor can shine a light on serious financial topics
- The impact of upbringing on money habits and mindset
- Money and gender roles — with a comedic twist
- A fun debate: “Would you do something wild for a big stack of cash?”
- Why laughter is one of the best ways to talk about money
💡 Key Takeaways
- Money is personal. Everyone’s relationship with it is shaped by background and experience.
- Humor opens doors. Laughing about money makes it easier to talk honestly.
- Gender roles play a role. Different expectations often influence money dynamics.
- Values matter more than cash. Not every opportunity is worth the money.
- Finance doesn’t have to be boring. Sometimes the best money lessons come wrapped in a joke.