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.

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”

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/
• Jeff Arnold's Website

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow.

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

Imagine a trolley hurtling down the tracks toward five people. You can pull a lever and divert it — but there's one person on the side track too. Most people pull the lever. And according to Ron Sosa, that's exactly how most workplaces are built: systems designed for the majority, with everyone else quietly getting run over. In this episode of Humor in the C Suite, Kate Davis sits down with Ron to talk about what it really costs to lead while masking, why humor is one of the most powerful tools for self-advocacy, and what becomes possible when leaders are finally given permission to lead as themselves.

Key Topics Covered

Ron and Kate explore the Trolley Scenario as a framework for understanding how workplace systems are designed — and who they leave behind. They dig into what masking actually costs neurodivergent leaders: the identity erosion, the accelerated burnout, the exhaustion of contorting yourself to meet an expectation that was never built with you in mind. Ron talks about how humor functions as a genuine tool for self-advocacy — not self-deprecation, but the ability to laugh at yourself in a way that makes the hard stuff lighter and the conversations easier. They cover the RISE framework, values-based leadership, and why Ron always starts coaching with personal values rather than professional ones. Kate shares her own experience with ADHD and anxiety, and Ron drops a stat that stops her mid-conversation: neurodivergent children receive an average of 20,000 more corrective comments than their neurotypical peers before the age of ten — and what that does to a person's relationship with humor, validation, and people-pleasing

Standout Quotes

"The ability to laugh at yourself makes the ability to advocate for yourself less heavy." — Ron Sosa

"Nobody is truly toxic. People just have unmet needs they don't know how to express — or needs we don't know how to meet." — Ron Sosa

"You conform to society, put on the leadership mask, and everything becomes heavier. You erode your own identity — and then you burn out faster." — Ron Sosa

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow.

Hosted by Kate Davis
Edited by Chris @ Wider View Studios

What does it look like when a shy kid who hated networking accidentally builds a game with 200 million players, survives corporate lawsuits, charms tax inspectors into forgetting why they came, and learns to lead by doing? That's Jeroen Derwort's story. In this episode of Humor in the C Suite, Kate Davis sits down with the former CEO of Gamebasics to explore how humor, humility, and a very healthy relationship with imperfection built one of the most unlikely success stories in gaming history — and what every leader can take from it.

Key Topics Covered
Jeroen and Kate explore how humor functioned as a genuine survival mechanism through the most stressful periods of building and scaling two tech companies simultaneously. They talk about the culture Jeroen created at Gamebasics — informal, creative, and rooted in shared laughter — and how that culture attracted people who genuinely wanted to be there. Jeroen shares how he handled the legal battles and corporate pressure that threatened to end the game entirely, and why having a light-hearted lawyer was one of the best leadership decisions he ever made. They dig into what it felt like when employees left and why Jeroen was genuinely hurt every time — a vulnerability Kate notes in 55+ episodes of the podcast she has never heard a leader admit before. And they cover Jeroen's philosophy on perfection: that doing something and seeing what happens will always beat waiting until everything is right.

Additional Links & Resources:

• Interested in being a guest on Humor in the C-Suite? Reach out to book a call with Kate!
• Learn more about me and my work at katedavis.ca

Thank you for tuning in to this episode of Humor in the C-Suite! If you enjoyed this episode, be sure to follow the podcast, share it with your friends, and leave a rating or review. Your support helps the podcast continue to grow.

Hosted by Kate Davis
Edited by Chris @ Wider View Studios