Episode 41: The Comedy Grind - What It Really Takes

In this episode of Put Your Funny Where Your Mouth Is, Vince Carone walks us through one of the most humbling and revealing moments of his career: flying to Nashville for a Monday night new material show—just to audition at a club in the same chain he already headlines in Chicago. It’s a story of emails ignored, nerves rising, and the quiet power of networking that speaks louder than a setlist.

Joined by Dobie Maxwell, the two comics unpack the true cost of being funny for a living—why the grind never stops, what’s changed in comedy booking, and how professionalism, perseverance, and likability matter more than ever. From being vouched for in a greenroom to mentoring the next generation, this episode reminds us that the real climb in comedy isn’t always the one audiences see.

Key Points Discussed:

• Why Vince had to “audition” at Zanies Nashville despite headlining elsewhere
• How networking and humility created a cascade of support before he even stepped on stage
• Dobie’s origin story with Dale Jones—and why a small favor changed a comic’s life
• The evolution of the comedy business: then vs. now
• Why “funny enough” isn’t enough anymore—and what matters more
• The role of sales, social skills, and likability in the modern comedy scene
• How mentorship works in both directions—when a 24-year-old comic helps a 42-year-old vet