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239: Mastering The Business of Storytelling: Stop Being Boring. Start Being Remembered. | Matthew Dicks
Episode 239
This episode is part of Mastering the Business of Storytelling, a Learn-It-All™ Mini-Series exploring how great leaders move people to action through story.
Level up your storytelling—and your leadership—in this must-listen episode of the Learn-It-All™ podcast. Host Damon Lembi welcomes Matthew Dicks, acclaimed storyteller, author, teacher, and nine-time Moth Grand Slam champion, to unpack the “why” and “how” 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 “work.” Plus: the secrets to a killer opening, why vulnerability trumps data, and Matthew’s acclaimed “Homework 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.
In this episode, 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 memorable—and trustworthy
- The biggest mistakes boring storytellers make (and how to learn from them)
- Why personal connection outsells products, and how to “story sell” in every meeting
- How “Homework 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 bios—and start with stories
Timestamps:
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 “trigger” 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 “how” 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 turnaround—a masterclass in crisis storytelling
40:17 – The “pickle 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 “Homework 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. Learn more at MatthewDicks.com and connect on
Published on 1 month, 1 week ago