Matthew Dicks is a best-selling author, columnist, blogger, podcaster, playwright, and teacher. He wrote my all-time favorite book on storytelling, Storyworthy. He is an elementary school teacher by day and by night teaches storytelling and public speaking to individuals, corporations, universities, religious institutions, and school districts around the world. He’s taught storytelling at Yale, MIT, Harvard, and Purdue, along with Amazon, Salesforce, Slack, Lego, and others. In this conversation, Matthew shares insights and techniques for effective storytelling, including:

• The benefits of good storytelling in business

• The five-second moment and why it’s so important

• Why you should start every story at the end

• How to build a vault of stories that can be deployed in business situations

• Tips on how to be funnier

• His life-changing “Homework for Life” practice

• Advice for dealing with nervousness in public speaking

• The power of saying yes

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Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-tell-better-stories-matthew

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Where to find Matthew Dicks:

• Website: https://matthewdicks.com/

• X: https://twitter.com/MatthewDicks

• LinkedIn: https://www.linkedin.com/in/matthew-dicks-84a95711/

• YouTube: https://www.youtube.com/channel/UC4K0fcEJkzJLso5h6CN00LQ

• Storyworthy: https://www.storyworthymd.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Matthew’s background

(04:27) The five-second moment

(10:29) Knowing the ending

(14:28) The importance of including a transformation

(15:59) The dinner test

(18:19) You can’t tell someone else’s story

(20:24) Vacation stories

(23:14) Adding stakes to the story

(25:12) The power of surprise

(29:20) The benefits of storytelling in business

(32:20) An example of adding stakes

(34:02) Storytelling in the workplace

(44:29) Using personal inventory to make stories relatable

(48:46) Four ways to keep people listening

(50:52) Using humor in business storytelling

(53:09) Advice for adding humor

(58:43) An example of how storytelling helped a biotech company sell product

(1:02:06) Advice for people who don’t want to become storytellers

(1:06:35) The power of “Homework for Life”

(01:15:26) Practical tips for starting Homework for Life

(01:19:28) Dealing with nervousness in public speaking

(01:24:42) Preparing for a talk or presentation

(01:25:24) The power of saying yes

(01:30:55) Lightning round

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Referenced:

• How ‘Star Wars’ answers our biggest religious questions: https://www.washingtonpost.com/posteverything/wp/2015/04/21/how-star-wars-answers-our-biggest-religious-questions/

• When Harry Met Sally on Prime Video: https://www.amazon.com/When-Harry-Sally-Billy-Crystal/dp/B001Q556QG

• Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennyspodcast.com/persuasive-communication-and-managing-up-wes-kao-maven-seth-godin-section4/

• Kurt Vonnegut’s 8 Tenets of Storytelling: https://www.themarginalian.org/2012/04/03/kurt-vonnegut-on-writing-stories/

• Vertigo on Prime Video: https://www.amazon.com/Vertigo-James-Stewart/dp/B000I9YLXU

• Ocean’s Eleven on Prime Video: https://www.amazon.com/Oceans-Eleven-George-Clooney/dp/B001EBV0JE

• David Mamet | JCCSF: https://www.youtube.com/watch?v=aZOT1jCHfhI

• Pulp Fiction on Prime Video: https://www.amazon.com/Pulp-Fiction-John-Travolta/dp/B005T3AX6E

• Charity Thief: Boston Moth StorySLAM: https://www.youtube.com/watch?v=YjrlGhAB4a4

• Boris Levin on LinkedIn: https://www.linkedin.com/in/boris-levin-ab95404/

• Masha Reutovski on LinkedIn: https://www.linkedin.com/in/masha-reutovski/

• Top Three Steve Jobs Speeches: https://www.pcworld.com/article/482269/top_three_steve_jobs_speeches.html

• The Javits Center: https://www.javitscenter.com/

• Stranger Things on Netflix: https://www.netflix.com/title/80057281

• 1989 (Taylor’s Version) on Spotify: https://open.spotify.com/album/64LU4c1nfjz1t4VnGhagcg

• Classic Sesame Street—one of these things is not like the other: https://www.youtube.com/watch?v=gCxrkl2igGY

• Homework for Life: https://matthewdicks.com/homework-for-life/

• Homework for Life | Matthew Dicks | TEDxBerkshires: https://www.youtube.com/watch?v=x7p329Z8MD0

• Seth Meyers: https://en.wikipedia.org/wiki/Seth_Meyers

• David Sedaris on MasterClass: https://www.masterclass.com/classes/david-sedaris-teaches-storytelling-and-humor

• Happy-Go-Lucky: https://www.amazon.com/Happy-Go-Lucky-David-Sedaris/dp/0316392456

• A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4

• New York Comedy Festival: https://nycomedyfestival.com/

• In the Heart of the Sea: The Tragedy of the Whaleship Essex: https://www.amazon.com/Heart-Sea-Tragedy-Whaleship-Essex/dp/0141001828

• The Tale of Despereaux: https://www.amazon.com/Tale-Despereaux-Being-Princess-Thread/dp/0763680893

• I’ll Show Myself Out: Essays on Midlife and Motherhood: https://www.amazon.com/Ill-Show-Myself-Out-Motherhood/dp/0062981595

• You’ll Grow Out of It: https://www.amazon.com/Youll-Grow-Out-Jessi-Klein/dp/1455531200

• David Sedaris books: https://www.amazon.com/stores/David-Sedaris/author/B000AQ3YUW

• Sure, I’ll Join Your Cult: A Memoir of Mental Illness and the Quest to Belong Anywhere: https://www.amazon.com/Sure-Ill-Join-Your-Cult/dp/1982168560

• The Last of Us on HBO: https://www.hbo.com/the-last-of-us

• Barbie: https://www.barbie-themovie.com/

• Krinner tree genie on Amazon: https://www.amazon.com/Krinner-Genie-Christmas-Stand-Small-Green/dp/B081D78FTP

• Power Pod: https://powerpodshop.com/

• Nostalgia hotdog toaster: https://www.amazon.com/Nostalgia-HDT600RETRORED-Pop-Up-Toaster-Retro/dp/B005Q8X6IO

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Rebel FM Episode 675 - 09/12/2025