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

Release Date:Β 

November 4, 2025

Release Date: Nov 4

Level up your storytellingβ€”and your leadershipβ€”in this must-listen episode of the Learn-It-Allβ„’ podcast. Host Damon Lembi welcomes Matthew Dicks, acclaimed storyteller, author, teacher, and nine-time Moth Grand Slam champion, to unpack the β€œwhy” and β€œhow” behind memorable stories that win hearts, minds, and deals. From actionable strategies for business leaders to the surprising lessons bad storytellers offer, this episode busts myths about what makes a story β€œwork.” Plus: the secrets to a killer opening, why vulnerability trumps data, and Matthew’s acclaimed β€œHomework for Life” tool to help you capture story-worthy moments in everyday life. If you want to boost your impact as a business leader, sales pro, or communicator, this conversation is packed with practical wisdom and real-world examples.

What You’ll Learn:

  • The 3 essential elements every great story needs (and why they matter in business)
  • Strategic ways to open a talk and instantly hook your audience
  • How sharing failures and vulnerability make you memorableβ€”and trustworthy
  • The biggest mistakes boring storytellers make (and how to learn from them)
  • Why personal connection outsells products, and how to β€œstory sell” in every meeting
  • How β€œHomework for Life” helps capture meaning from everyday moments
  • Smart tips for creating suspense, surprise, and credibility in any setting
  • Why leaders need to stop relying on biosβ€”and start with stories

In This Episode:

  • 00:00 – The power of leveling up your storytelling skills quickly
  • 02:06 – Matthew’s aha moment on why leaders need stories
  • 03:24 – 3 main building blocks of memorable stories
  • 06:38 – The value of competition, Moth victories, and peer recognition
  • 09:00 – Learning from bad storytellers: watching, flipping, and avoiding mistakes
  • 11:35 – Why your opening matters more than your ending
  • 13:36 – How to instantly β€œtrigger” story mode in your audience’s brain
  • 17:26 – Why most storytellers start too soon (and how to find the right beginning)
  • 19:24 – Getting technical people and scientists out of the β€œhow” trap
  • 22:04 – Why people buy humans, not products: Trevor Devine’s windows story
  • 26:53 – How to demonstrate empathy and listen deeper than content matching
  • 27:23 – Matthew’s 100% close rate as a wedding DJ (and the storytelling secret)
  • 33:25 – Vulnerability in sales: sharing your mistakes builds trust
  • 35:32 – Domino’s Pizza turnaroundβ€”a masterclass in crisis storytelling
  • 40:17 – The β€œpickle story”: specificity and context in storytelling
  • 44:30 – Creating surprise and suspense in everyday presentations
  • 46:59 – Tips for using information exclusion to hook audiences (the suspense formula)
  • 50:31 – Storyworthy’s β€œHomework for Life”: capturing stories from your everyday
  • 56:23 – The single biggest lesson Matthew learned from decades as a teacher

About Matthew Dicks

Matthew Dicks is an award-winning storyteller, novelist, elementary school teacher, and renowned coach to leaders across Fortune 500 companies. He’s the bestselling author of Storyworthy and Story Sell and has won the Moth Grand Slam nine times, making him a legend in the world of competitive storytelling. Matthew teaches storytelling workshops and gives keynotes for clients including Google, Microsoft, and Slack, helping people turn ordinary moments into extraordinary connections and results.

Resources Referenced:

  • Matthew Dicks on
  • (Matthew’s book on personal storytelling)
  • (Matthew’s book on business storytelling)
  • Jolt Effect” by Matt Dixon ()

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