Capital Allocators – Inside the Institutional Investment Industry
Episode 477: Matthew Dicks – Storytelling Mastery
Host: Ted Seides
Guest: Matthew Dicks
Release Date: December 15, 2025
Episode Overview
In this engaging and practical episode, Ted Seides is joined by master storyteller and bestselling author Matthew Dicks. The conversation dives into the art and science of storytelling—what makes an impactful story, how anyone (even business executives and investors) can harness its power, and why storytelling is an essential, learnable skill for communication, persuasion, and leadership. Matthew walks listeners through his process of unearthing, constructing, and delivering memorable stories, emphasizing tools, structure, and performance techniques that transcend traditional business “presentations.”
Key Discussion Points & Insights
1. The Power of Storytelling vs. Presentations
- Storytelling ≠ Presenting:
Matthew opens with a provocative claim: stop calling it a "presentation."“No one ever wakes up in the morning hoping to see a presentation, but they do wake up every morning hoping to see a performance. So get rid of that word.” — Matthew Dicks (00:00)
- Performance Mindset:
Embracing "performance" increases preparation, focus on the audience, and entertainment value. A presentation can be read by a monkey with a slide deck; a performance requires human engagement.
2. Demonstration: Telling an Original Story
- Live Example:
Matthew shares a never-before-recorded personal story from his teaching life (06:29–15:25). The story follows the arc of a supposedly routine day disrupted by a truly unique, once-in-a-lifetime incident involving his wife and a fifth-grade student.- Insight:
The story highlights the search for "singular moments" and the beauty in recognizing extraordinary experiences amid the mundane.
- Insight:
3. Matthew’s Storytelling Genesis & Philosophy
- Origins:
- Began storytelling at The Moth in 2011 on a dare (15:50).
- Realized early obsessions were always about dissecting stories—e.g., critiquing Spielberg as a child (17:30).
- Teaching Others:
- Transitioned from instinctual storytelling to teaching others by breaking down his process into steps.
- Developed his signature curriculum, leading to his book Storyworthy (19:03).
4. Where Stories Come From: Homework for Life
- Exercise:
“Homework for Life” – every day, reflect and record a story-worthy moment (25:38).“All you have to do is start paying attention to your life, finding a way to hold onto it, and you’ll have more stories to tell than you have time to tell them.” — Matthew Dicks (26:51)
- Lost Memories:
Most of what happens is forgotten—deliberate reflection is essential to stock storytelling “inventory.”
5. Story Construction: Structure, Openings, and Endings
- Where to Start:
- Spend most time deciding where to begin.
- Classic structures: Chronological vs. non-chronological (Forrest Gump as example) (27:28).
- For personal stories that span time, alternate between time periods for enhanced engagement (C, A, B, C structure).
- What Makes a Good Start:
“Start with location in action. Every story you tell for the rest of your life, you should start with ‘Where was I?’ and ‘What was I doing?’” (30:40)
- Triggers attention, releases brain chemicals associated with learning and memory.
- Essential Elements for Engagement:
- Stakes: What’s at risk/what are we curious about?
- Suspense: Strategic withholding and sharing of information.
- Surprise: Create moments of genuine, unexpected realization.
- Humor: Lightens tension, establishes intelligence, and fosters connection (34:07).
6. Humor: Unlocking Laughter in Stories
- Humor as a Learned Skill:
List of 27 humor strategies; top 10 are highly reliable (37:31). - Accessible Humor Tools:
- Nostalgia: Remind people of “the way things were”—effective and safe in business (38:33).
- “One of These Things is Not Like the Other”: List three things, with the last as the outlier for comedic effect (40:38).
- Definitions: Define something in simplest form, then riff on it for punchlines (41:40).
7. Speech Patterns and Story Flow
- Avoid Linear “And-And-And” Stories:
Instead, use “but,” “therefore,” and “because” for a dynamic, up-and-down narrative (43:01). - Eliminate Weak Storytelling Phrases:
Words/phrases like “suddenly,” “little did I know,” and “guess what?” are counterproductive—strip them out for stronger stories (44:49).
8. Detail Management: What to Keep and Discard
- Relevance Rules:
Only keep details that advance the story, provide clarity, or enhance entertainment. Ruthlessly cut anything else (46:48).“If the detail does not serve the story, if it does not help me get to the end, if it does not bring something to clarity or entertain, then it goes away.” — Matthew Dicks (46:48)
9. Endings: Landing the Plane
- Know the End Before You Start:
Start with the ending in mind to avoid losing direction (51:14).- Endings are typically realizations, transformations, or a changed perspective.
“The end of every story is always a realization or transformation of some kind...That’s the most important part of the story. It’s the most important thing you have to say.” — Matthew Dicks (51:44)
10. Business Application: Presenting as Performance
- The “Presentation” Trap:
Most business “presentations” are slide-driven and unimaginative.- Prepare and perform instead; ditch over-reliance on slides.
- Use storytelling strategies in business: stakes, suspense, surprise, and humor (54:42).
- “Speaking through adjacency”:
Use personal anecdotes as analogies for business concepts (56:25).
Example: Executive uses a dishwasher anecdote to reframe sales about equipment upgrades. - Case Study:
Biotech company—scientists present findings as stories (apples at the grocery store as a metaphor for tailored scientific equipment). Results: more engagement and sales leads (70:51).
11. Common Business Pitfalls
- PowerPoint Dependency:
Slides should aid, not drive, the story (60:46). - Preparation Gap:
Practice and performance are key—know your material so well that you can adapt if you forget a part (64:56).
12. Practice & Memorization
- Best Practice:
Record and re-listen to your story repeatedly (like internalizing song lyrics) (64:54). - Remember, Don’t Memorize:
Don’t lock yourself into a strict script—memorize openings and key transitions, but allow for improvisational flow (66:26).
13. Feedback & Shifting Culture
- Feedback Shift:
Positive feedback increases consistency and frequency of good habits (69:04). - Organizational Buy-In:
Companies are convinced only when they see measurable impact (storytelling leads to more opportunities—apples anecdote case).
Memorable Quotes
-
"No one ever wakes up in the morning hoping to see a presentation, but they do wake up every morning hoping to see a performance." — Matthew Dicks (00:00)
-
"All you have to do is start paying attention to your life, finding a way to hold onto it, and you’ll have more stories to tell than you have time to tell them." — Matthew Dicks (26:51)
-
“If the detail does not serve the story, if it does not help me get to the end, if it does not bring something to clarity or entertain, then it goes away.” — Matthew Dicks (46:48)
-
“The end of every story is always a realization or transformation of some kind...That’s the most important part of the story. It’s the most important thing you have to say.” — Matthew Dicks (51:44)
-
“Slides should be used to support a story only when necessary. They should not be the story...If you need a slide deck and you’re competing against me, all I will do is I’ll cut the power to the building.” — Matthew Dicks (60:46)
Notable Moments & Timestamps
- Opening: Get rid of ‘presentation,’ think ‘performance’ (00:00)
- Live Story Demonstration (06:29–15:25)
- Origins of Storytelling Passion (15:50–18:56)
- Homework for Life Explained (25:38–27:17)
- Story Structure Deep Dive (27:28–30:37)
- Humor Techniques (38:33–41:40)
- How to Cut Details & Serve the Audience (46:48–51:10)
- Business Storytelling Translation & Steve Jobs Example (56:25–60:39)
- Why Slide Decks Kill Performance (60:46–63:16)
- Practice & Memorization Methods (64:54–68:58)
- Case Study: Biotech “apple” story outsells all (70:51)
- “What did JP say?”—Story behind the story pay-off (76:37)
- Legacy, Closing Reflections & Personal Lessons (77:38–89:58)
Practical Takeaways
- Start stories with location and action—it triggers engagement and memory.
- Prepare like a performer, not a presenter.
- Use “Homework for Life” to never run out of material.
- In presentations, ditch the slides. Tell human stories that connect.
- Apply four essential entertainment strategies: stakes, suspense, surprise, humor.
- In business, use personal stories as analogies for complex points or to foster connection.
- Practice by listening to recordings of your talk; strive to “remember, not memorize.”
- Ruthlessly cut details and focus on the story the audience wants to hear, not just what you want to tell.
For New Listeners or Business Leaders
If you’re new to storytelling or want to drastically improve your public speaking, this episode offers clear, actionable guidance—whether you aim to inspire troops, pitch investors, or simply make your meeting memorable.
For more information on Matthew Dicks’ work: