This week I’m joined by Jeff Arnold: five-time bestselling author, founder of RightSure (North America’s most awarded insurance firm), and a guy who somehow turned standing next to a serious CEO at a drink fountain into a leadership lesson. We talk about why self-deprecating humor is the best humor, why “yes, and” belongs in your boardroom and not just your improv class, how Jeff kills his own ego every time he writes a book, and the story behind the most expensive speeding-ticket photo in Arizona history. Bring tissues. You’ll need them for laughing.
About the Guest
Jeff Arnold is a five-time best-selling author whose writing cadence pulls readers in like a conversation with a trusted guide. His words aren’t just read, they’re experienced. With a style that blends vivid storytelling, sharp insight, and practical wisdom, Jeff takes each reader on a journey where ideas become images and lessons become lived moments.
He is also the founder of RIGHTSURE, North America’s Most Awarded Insurance Firm, blending technology with humanity. He loves to challenge audiences to think bigger, lead boldly, and embrace what’s possible. Whether exploring business, leadership, artificial intelligence, or the future of technology, his work makes the complex feel clear, the distant feel close, and the abstract feel unforgettable.
Key Topics
- Self-deprecating humor as a leadership trust-builder
- The “yes, and” philosophy from improv, applied to business
- Reframing failure as forward motion
- Using humor to deliver hard news without losing authenticity
- Writing 12 books and learning to kill your own ego on the page
- Humor and AI: deploying technology without losing the human side of leadership
- Rebranding insurance agents as “famously friendly humans”
- Knowing your audience: when to dial humor up, and when to dial it down
- The line between self-deprecating humor and “punching down”
Standout Quotes
- “The older I get, the more I believe that humor isn’t something we bring to work. It’s the thing that keeps us from leaving work.” Jeff Arnold
- “If we are the biggest joke in the room, no one else has to be nervous about being one.” Jeff Arnold
- “Humor reframes any failure as forward motion.” Jeff Arnold
- “My door is always open. Mostly because I keep forgetting to close it.” Jeff Arnold
- “It’s finding those little nuggets where you can truly be yourself.” Kate Davis
Guest Advice
Lead with self-deprecating humor before anyone else gets the chance to make you the joke. It signals confidence, not weakness, and it’s the fastest way to build trust with a team.
Resources Mentioned
- RightSure Insurance
- Jeff’s book, AI Forward Leadership
- Jeff has written 12 books total, 5 of them bestsellers https://jeffarnold.com/books/
Connect
- Jeff Arnold’s Website
- Want to be a guest on Humor in the C-Suite? Email kate@katedavis.ca or Contact Me here
