What do improv comedy, standup, and high-performing salespeople have in common? More than you think.

In this episode of Sales & Cigars, Walter Crosby sits down with Kevin Hubschmann to explore how comedy skills like active listening, adaptability, brevity, and comfort with failure directly translate to better sales conversations.

Kevin shares how doing improv in a cramped New York apartment sharpened his instincts on sales calls, why scripts often fail in real-world selling, and how learning to bomb—on stage and in sales—became a competitive advantage. This is a practical, mindset-shifting conversation for sellers who want to think differently about discovery, messaging, and growth.

In This Episode:

Falling into sales while trying to survive in New York City
How improv immediately improved Kevin's sales calls
Why listening is the most underrated sales skill
The danger of rigid scripts when buyers "take a left turn"
What standup comedy teaches about clarity and concise messaging
Why losing deals is essential to becoming a better salesperson
Using low-stakes reps to test ideas and improve performance
How comedy training is now being used to develop sales teams

Key Takeaways:

Great sales conversations are collaborative, not scripted
Listening beats pitching every time
Clear, concise messaging travels further inside an organization
Failure is data—not a verdict
Reps, reflection, and refinement matter more than talent

Connect with Kevin:

LinkedIn: https://www.linkedin.com/in/kevin-hubschmannn/
Instagram: https://www.instagram.com/laughdotkevin/
Laugh.Events: https://www.laugh.events/

Connect with Walter Crosby and Sales & Cigars:

Website: Helix Sales Development

LinkedIn: Walter Crosby

Instagram: @wcrosby248

Facebook: Helix Sales Development

Share Your Thoughts:

We'd love to hear your feedback and experiences! Drop us a line and join the conversation on social media using #SalesAndCigars.

Never Miss an Episode!

Join the Sales & Cigars community by subscribing to our podcast and YouTube channel:

Subscribe to the Podcast:

Apple Podcasts: Subscribe on Apple Podcasts

Spotify: Follow on Spotify

...and wherever you listen to podcasts!

Subscribe to Us on YouTube:

Stay updated with our latest video content by subscribing to our YouTube channel. Hit the bell icon for notifications on new uploads!

YouTube: Sales & Cigars Channel

Stay in the loop: By subscribing, you'll get instant access to new episodes, insightful conversations, and bonus content designed to elevate your sales skills and more.

Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.