A Note from James

I’m honored to have today’s guest: Tristan de Montebello, a finalist in the World Championship of Public Speaking. He also co-founded UltraSpeaking (ultraspeaking.com/james), where he teaches techniques to improve communication through games and real-world practice. We even played some of those games during this episode, and they surprised me with how much they revealed about my own speaking.

Public speaking isn’t just about giving a good talk—it’s about understanding who you are, what you stand for, and how you connect with others. I’ve been speaking for more than 25 years, but I’m still always looking for ways to improve. At the end of the day, sharing ideas—through writing, storytelling, or speaking—is how you can change the world.

This conversation with Tristan is fascinating because he’s gone from zero experience to becoming one of the best in the world, all while reverse-engineering what it takes to truly connect with an audience.

Episode Description

How does someone go from a complete beginner to a world-class speaker in less than a year? Tristan de Montebello did exactly that—and in the process, he uncovered the strategies, mindsets, and training methods that make communication powerful.

In this episode, James and Tristan break down the mechanics of storytelling, humor, vulnerability, and flow in speaking. They explore why audiences respond the way they do, how to use analogies to create connection, and why mindset is the foundation of every great communicator.

Whether you’re on a stage, in a meeting, or simply trying to share an idea with friends, these lessons will change the way you approach communication.

What You’ll Learn

• How Tristan went from novice to World Championship finalist in under a year.
• Why humor and vulnerability are essential ingredients for authentic connection.
• Practical ways to use storytelling and analogies to make ideas stick.
• How to handle insecurity, fumbles, and “tough audiences” without breaking flow.
• Why mindset—not technique—is the foundation of great communication.

Timestamped Chapters

• [01:00] A Note from James and introducing Tristan de Montebello
• [04:15] Inside the World Championship of Public Speaking
• [07:45] Humor, storytelling, and why connection matters
• [11:10] The Fear Olympics: lessons from Tristan’s grandmother
• [16:30] “Never be the hero of your own story”
• [20:15] Breaking down stories like Finding Nemo
• [24:45] How Tristan trained humor like a stand-up comic
• [28:30] What great speakers and clowns have in common 
• [33:20] Managing insecurities and staying in character
• [41:40] From finalist to struggling in an online mastermind
• [50:20] Slacklining as a metaphor for learning
• [54:10] Building analogies as a core communication skill 
• [60:30] Reading tough or quiet audiences
• [67:15] Handling bias and building trust with skeptical crowds
• [69:45] Flow state in public speaking

Additional Resources

• UltraSpeaking – ultraspeaking.com/james
• Toastmasters International – toastmasters.org
• Rich Dad Poor Dad by Robert Kiyosaki – Amazon link
• Eight Mile (film referenced by James & Tristan) – IMDb

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