239: Mastering The Business of Storytelling: Stop Being Boring. Start Being Remembered | Matthew Dicks

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Written By damon lembi

Matthew Dicks, bestselling author, teacher, and nine-time Moth Grand Slam champion, joins Damon Lembi for a masterclass on storytelling that wins hearts, minds, and deals. Drawing on decades of experience as a performer and coach to Fortune 500 leaders, Matthew breaks down the art and science of great storytelling—why vulnerability beats data, how to hook your audience instantly, and the biggest mistakes boring storytellers make. Plus, he shares his signature Homework for Life tool to help you uncover story-worthy moments hiding in your everyday life.

Read the full breakdown of Matthew Dicks’ episode on Learnit.

Key Leadership Lessons from Matthew Dicks’ Journey:

  • Stories beat stats: The most persuasive leaders use emotion and narrative—not just information—to connect.

  • Open strong: Great stories hook in seconds with tension, curiosity, or surprise.

  • Vulnerability builds trust: Sharing real, imperfect moments makes you memorable and human.

  • Learn from bad storytellers: Spotting what doesn’t work teaches clarity, pacing, and empathy.

  • Capture meaning daily: Matthew’s Homework for Life helps leaders transform everyday experiences into teachable stories.

Connect with Matthew Dicks:

Matthew is a celebrated storyteller, novelist, and educator whose workshops have helped leaders at Google, Microsoft, and Slack craft messages that inspire action. His work blends humor, empathy, and strategy—showing that the best stories aren’t told, they’re lived.

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238: The Hidden Cost of Leading Without Laughter | Greg Kettner