Skip to content
Lenny's PodcastLenny's Podcast

How to tell better stories | Matthew Dicks (Storyworthy)

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 — Brought to you by OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny | Maui Nui Venison—The healthiest red meat on the planet delivered directly to your door: https://mauinuivenison.com/discount/LENNY?utm_medium=podcast&utm_source=show_notes&utm_campaign=lenny | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-tell-better-stories-matthew 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/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Matthew DicksguestLenny Rachitskyhost
Dec 15, 20231h 42mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
December 15, 2023
Duration
1h 42m
Channel
Lenny's Podcast
Watch on YouTube
▶ Open ↗

EPISODE DESCRIPTION

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

— Brought to you by OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny | Maui Nui Venison—The healthiest red meat on the planet delivered directly to your door: https://mauinuivenison.com/discount/LENNY?utm_medium=podcast&utm_source=show_notes&utm_campaign=lenny | Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-tell-better-stories-matthew Where to find Matthew Dicks:

Where to find Lenny:

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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

SPEAKERS

  • Matthew Dicks

    guest

  • Lenny Rachitsky

    host

EPISODE SUMMARY

In this episode of Lenny's Podcast, featuring Matthew Dicks and Lenny Rachitsky, How to tell better stories | Matthew Dicks (Storyworthy) explores mastering Business Storytelling: Five-Second Moments, Stakes, and Yes Matthew Dicks, champion storyteller and author of *Storyworthy*, explains how to craft powerful stories for both life and business, centering everything on a single "five-second moment" of transformation or realization.

RELATED EPISODES

How to build a company that withstands any era | Eric Ries, Lean Startup author

How to build a company that withstands any era | Eric Ries, Lean Startup author

Head of Claude Code: What happens after coding is solved | Boris Cherny

Head of Claude Code: What happens after coding is solved | Boris Cherny

Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead)

Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead)

Building a world-class data org | Jessica Lachs (VP of Analytics and Data Science at DoorDash)

Building a world-class data org | Jessica Lachs (VP of Analytics and Data Science at DoorDash)

What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author)

What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author)

5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker)

5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker)

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome