Dec 15, 2023 · 1h 42m · lennys-podcast
How to tell better stories | Matthew Dicks (Storyworthy)
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Storytelling master Matthew Dicks shares actionable frameworks for crafting compelling personal and professional narratives centered on a five-second moment of transformation. He provides tactical methods for raising stakes, infusing business communication with vulnerability, capturing daily life stories, and overcoming stage fright.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 15.2% of the talking time here. How this is scored →
Lenny as informed peer 3.4 Guest teaching 6.7 Guest disagreement 1.3 Lenny pushing back 0.8
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:25:53 Pushing back on chasing crazy stunts for stories
Matthew directly challenges the popular writing trope endorsed by Sedaris and other authors, insisting that seeking out wild escapades to create stories is foolish because true realization occurs quietly in everyday moments.
Hardest push from Lenny ▶ 1:02:07 Pressing for practical on-demand storytellingLenny challenges Matthew's dismissal of the ad-hoc 'band-aid' approach, pressing him on how everyday business professionals who lack a pre-built story bank can still solve immediate workplace communication problems.
Biggest teaching moment ▶ 25:19 Systematic breakdown of narrative suspense toolsMatthew delivers a masterclass on engineering suspense, teaching the host five distinct mechanical tools (the elephant, backpack, breadcrumbs, hourglass, and crystal ball) for sustaining audience attention.
Lenny holds their own ▶ 29:11 Connecting dramatic theory and cinematic pacingLenny demonstrates deep narrative knowledge by connecting Matthew's stakes framework to David Mamet's dramatic theory of inevitable surprise and citing Tarantino's pacing in Pulp Fiction.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| The Core of Story: The Five-Second Moment | 3 | 6 | 1 | 1 | Lenny kicks off the interview by asking Matthew to unpack the central premise of Storyworthy: that every story hinges on a five-second moment of change. Matthew provides an extensive explanation of transformation versus realization. | |
| Realizing the Five-Second Moment: Eileen and Star Wars | 2 | 7 | 1 | 0 | Lenny invites concrete examples, and Matthew illustrates the concept using both a classroom interaction with his student Eileen and Luke Skywalker's climactic arc in Star Wars. | |
| Starting at the End and the Opposites Framework | 4 | 6 | 1 | 1 | Lenny points out how knowing the ending moment informs the beginning, citing When Harry Met Sally. Matthew elaborates on constructing opposites between a story's beginning and conclusion. | |
| The Universal Appeal of Emotional Change | 3 | 7 | 2 | 1 | Lenny asks why transformation is essential to storytelling. Matthew explains universal emotional resonance and details the 'dinner test' rule against artificial theatrical gimmicks like sound effects. | |
| Personal Storytelling and the Power of Vulnerability | 4 | 6 | 1 | 1 | Lenny brings up the rule that stories must be personal. Matthew explains why storytelling requires personal vulnerability, illustrating with how he trains descendants of Holocaust survivors. | |
| How to Tell Vacation Stories and Starting Late | 5 | 6 | 2 | 1 | Lenny asks about Matthew's rules for vacation stories and brings up Wes Kao's advice to start when the bear eats the tent. Matthew connects this to Kurt Vonnegut's principle of starting near the end. | |
| Generating Suspense and Raising Narrative Stakes | 3 | 8 | 1 | 1 | Lenny prompts Matthew on how to raise stakes in true stories. Matthew provides an in-depth breakdown of narrative stakes mechanisms: the elephant, backpack, breadcrumbs, hourglass, and crystal ball. | |
| Crafting Inevitable Surprises and Managing Stakes | 6 | 6 | 1 | 1 | Lenny introduces David Mamet's concept of inevitable surprises and uses Pulp Fiction to illustrate pacing techniques. Matthew explains how hidden information makes surprises feel inevitable. | |
| Deploying Stakes Effectively in True Stories | 4 | 6 | 1 | 1 | Lenny brings up the 'drop a dead body' rule and asks for recorded examples of stakes in action. Matthew analyzes his own performance in Charity Thief versus his McDonald's bachelorette story. | |
| Escaping Corporate Mediocrity with Storytelling | 3 | 7 | 2 | 1 | Lenny shifts to applying storytelling in business. Matthew critiques corporate communication for being 'round, white, and flavorless' due to professionals fearing standing out from the herd. | |
| Business Applications: Boris Levin's Little League Story | 3 | 7 | 1 | 1 | Lenny asks how business storytelling can avoid feeling preachy or annoying. Matthew shares how Boris Levin used his son's Little League strikeout to reset sales team morale and contrasts bricks with band-aids. | |
| Humanizing Corporate Messaging: The Slack Origin Narrative | 2 | 7 | 1 | 0 | Matthew details coaching Slack's corporate comms leader Masha Ratovsky to include a vulnerable personal anecdote about formulating Slack's anti-Teams positioning over wine during the pandemic. | |
| Building Relatability with Personal Interest Inventories | 3 | 7 | 1 | 1 | Lenny asks whether business presenters should always insert personal details. Matthew introduces the Personal Interest Inventory framework for establishing quick audience rapport. | |
| The Four Engagement Pillars and Taking Humor Risks | 3 | 7 | 2 | 1 | Matthew outlines the four pillars for holding attention—stakes, surprise, suspense, humor—and recounts coaching an executive who panicked and cut his jokes at the Javits Center. | |
| Sponsor Break: Vanta Compliance Automation | 2 | 7 | 2 | 0 | After an ad break, Lenny asks how to be funnier. Matthew teaches two practical humor techniques: nostalgia (contrasting 1983 job searches with today) and the Sesame Street rule of three. | |
| Storytelling in Sales: The Apple Analogy for Biotech | 3 | 7 | 1 | 1 | Lenny asks for unconventional business use cases. Matthew recounts coaching biotech scientists where an apple-shopping analogy dramatically outperformed dry data slides. | |
| Speaking with Adjacency: Thematic Story Alignment | 5 | 7 | 1 | 1 | Lenny presses Matthew on how practitioners with immediate problems can generate stories on demand. Matthew teaches 'speaking with adjacency' by matching theme, meaning, or message rather than literal content. | |
| Homework for Life: Discovering Everyday Stories | 3 | 8 | 1 | 1 | Matthew explains his cornerstone practice, 'Homework for Life,' describing how logging daily moments in a spreadsheet expanded his story discovery rate from 1.8 to 7.6 moments per day. | |
| Therapeutic Insights and Uncovering Life Patterns | 3 | 7 | 1 | 0 | Matthew details the therapeutic benefits of Homework for Life, explaining how it reveals subconscious behavioral patterns (like chore-based arguments) and uncovers hidden narrative arcs. | |
| Implementing Homework for Life in Daily Practice | 3 | 7 | 1 | 1 | Lenny asks how listeners can implement Homework for Life tonight. Matthew gives tactical advice on daily time-stamping, spreadsheet logging, and practicing decision-making over oratorical polish. | |
| Conquering Stage Fright and Internalizing Presentations | 4 | 7 | 1 | 1 | Lenny asks for advice on stage fright. Matthew explains that 98% of anxiety precedes speaking, advocating for passive auditory review and internalizing scene transitions over rote memorization. | |
| Embracing Fear and the Transformative Power of Yes | 4 | 7 | 3 | 1 | Lenny references David Sedaris's philosophy of saying yes to everything to get stories. Matthew offers a nuanced pushback, arguing yes is about overcoming hubris and fear rather than chasing extreme stunts. | |
| Lightning Round: Recommendations, Products, and Philosophy | 3 | 4 | 1 | 1 | In the lightning round, Matthew shares his top book recommendations, praise for The Last of Us and Barbie, preferred hiring questions, unique gadget finds, and fourth-grade life motto. | |
| Essential Story Starters: Grounding in Location and Action | 3 | 7 | 1 | 0 | Lenny asks for one final actionable tip. Matthew advises beginning every story with immediate physical location and action to activate listener imagination and establish conversational authority. |
Statements from this episode (38)
Dicks: Every compelling story centers on a five-second moment of transformation
“Essentially every story is about a singular moment. I call it five seconds. It can be 1:02. Honestly, it's a moment of either transformation, meaning sort of, I'm telling you a story about how I once used to be one kind of person and now I'm a new kind of pers…”
Dicks: The original Star Wars is fundamentally a movie about religion
“You know, if you think about a movie like Star Wars, the first Star Wars that came out, right, that is a movie essentially about religion, which people sort of don't always see, but it is true.”
Dicks: Stories resonate because audiences universally relate to finding belief
“And that's why a story like that resonates with us in a way that another story might not, because we all understand what it's like to not believe in something, And then find belief in something, whether that is religious belief, or I used to think cheeseburger…”
Dicks: Compelling stories begin and end in opposition
“Every story should be essentially a beginning and an end in opposition to each other, and you should start at the end. That guarantees that you have something important to say, rather than what most people do, which is they simply report on their lives. They j…”
Dicks: Stories in formal pitches should sound like natural dinner conversations
“When you're telling a story in a formal way, if you're performing on a stage or delivering a keynote, or even delivering sort of a pitch to entrepreneurs or a sales pitch, essentially the story that you're telling should be very closely related to the story yo…”
Dicks: Storytellers should never open a story with unattributed dialogue
“Weird things that people do should not be done, like opening a story with unattributed dialogue. You know, so you're standing on stage and you open your story with, Jim, it's time to come in for dinner, my wife said. Like, that's just weird. We don't talk like…”
Dicks: Stories Must Be About the Speaker to Convey True Vulnerability
“If you're telling a story about someone else, essentially you might as well be telling fiction because that person's not in the room and to the audience, they don't really exist unless they're, you know, if they can't see them, that person is just another huma…”
Matthew Dicks: Shortest version of every story is the best version
“The shortest version of every story is the best version of every story.”
Dicks: Stories should always begin as close to the end as possible
“Starting as close to the end of a story is always the best place to begin.”
Dicks: Audiences stop listening when not wondering what comes next
“If your audience isn't wondering what you're about to say, They're no longer listening to you.”
Dicks: Business leaders mistakenly assume job titles grant audience attention
“When I work with people in business, they are constantly under this misconception that people want to hear what they have to say. You know, some vice president of marketing thinks that because they're a vice president of marketing and everyone is sitting in a …”
Dicks assumes nobody in the audience wants to hear him speak
“I assume all the time, 100% of the time, that no one wants to hear anything I have to say.”
Dicks: The best story surprises feel inevitable yet completely unexpected
“You build information into the audience's mind that will allow the surprise to land in an inevitable and yet surprising way. That is the best surprise you can offer someone.”
Dicks: Storytellers should spread stakes across the first half, not front-load them
“So often people load the front end of a story with all of the stakes because they're worried that the audience will not pay attention to them. So they think I'm going to throw everything right in front and that'll hold an audience for the rest of the story. An…”
Dicks: Most Business Communication Is Bland Because Workers Fear Standing Out
“Most communication in business is round, white, and flavorless, right? Intentionally so, because a lot of people are afraid to stand out.”
Dicks: Communicators Who Rely on Data Without Storytelling Are Inevitably Forgotten
“Our minds are not designed to remember a pie chart. Or facts, or statistics, or, you know, platitudes, or ideas that are not attached to imagery. So the risk you take if you're not telling stories is that you will be forgotten. 100% you will be forgotten.”
Dicks: Leaders should build a story vault rather than use one-off fixes
“If you're building bricks, you're a storyteller that's capturing stories and building bricks that you can eventually deploy into business. If you're a band-aid person, which is fine, that happens. I have a problem, Matt, and I need a story to solve it. Essenti…”
Dicks: Married men in business should disclose marriage to project safety
“If you're married, you should always make it clear to people you're married, especially if you're a man, because if you're a man and you're married, you're safer in the world because men are inherently just dangerous human beings.”
Dicks: Answering 'how are you doing' with 'great' is a wasted opportunity
“You know, if someone asks you, how are you doing today? If you say I'm doing great, you've just really screwed it up. That's the stupidest answer you can offer, right?”
Dicks: Corporate leaders want to have been funny without taking humor risks
“Everyone wants to be funny. Every person I've ever met who I've worked with every business person in some way wanted to be funny, but that's really not actually what they want. They want to have been funny. Because being funny means you must take a risk.”
Dicks: Speakers must use stakes, surprise, suspense, or humor to keep attention
“It's stakes, it's surprise, it's suspense, and it's humor. Those are the ways that you're going to hold people and keep them listening, and if you're not engaged in one of those four things while you're speaking, people are not listening to you anymore.”
Dicks: Using nostalgia demonstrates company expertise and reliably adds humor
“It's relevant to talk about the past as a company to demonstrate your expertise in your field. To understand that we know the market backwards and forwards for the last 50 years. We have expertise, and we can demonstrate it by telling a story, right? So that's…”
Dicks: Listing two expected items then one unexpected item creates humor
“Essentially, it's three things. Two of them are expected, and one is unexpected, and the unexpected one will be funny.”
Dicks: Story-based humor prevents awkwardness when jokes fail to land
“We're telling humor in the confines of a story, so that if this joke doesn't land, we're still telling a story, and oftentimes people don't even realize we're trying to be funny.”
Dicks: Biotech scientist telling pure story won more conference leads than peers
“He got more leads at the conference than the other scientists combined. All the other four scientists combined.”
Dicks: Storytelling embeds subconscious advertising into everyday objects
“We create positive connections with items in the world related to our company by telling stories, and that means we've, like, built advertising into people's lives Without them even being aware that we've done it.”
Dicks: Removing yourself from personal stories yields effective business metaphors
“And if you take yourself out of a story, often what's left is a metaphor, a simile. An example.”
Dicks: Match stories to business ideas by theme, not literal content
“The best way to sort of tell a story about something that you want people to understand is to do what I call speaking with adjacency, which means we're not going to match content to content. Instead, we're going to match theme, meaning, or message.”
Dicks: Time feels fast because people fail to account for daily memories
“You know, people say that time flies and it doesn't. What happens is it goes by unaccounted. If you can only remember 89 days of 365 in a year, of course time flies, because you had three 65 and you only remember 89. It's gonna feel like it went by quickly. It…”
Dicks: Storytellers are positively self-centered by taking time for self-reflection
“Storytellers tend to be Slightly self-centered in a positive way, meaning we afford ourselves time to think about ourselves.”
Dicks: Storytelling is about decision-making, not vocabulary or language facility
“Storytelling is not about facility with the language or your vocabulary. It's all about decision making. That's all it is. Storytellers are people who think before they speak. They make strategical, tactical decisions before they speak.”
Dicks: Being entertaining is the most important requirement in any communication
“Ultimately, no matter what you're doing, whether I am teaching a fifth grader how to behave better, or presenting a new product for a large company, or helping someone deliver in all hands, the first and most important thing you have to be is entertaining. You…”
Matthew Dicks: 98% of stage nervousness occurs before speaking starts
“98% of your nervousness is actually before you begin speaking. Once you begin speaking, almost all of your nervousness falls away.”
Matthew Dicks: Speakers forget presentation transitions, not core content
“Most people don't forget their talk. They forget the transitions in their talk.”
Matthew Dicks: Speakers should avoid rote memorization of presentations
“If you can avoid memorizing, that'll save you. A ton of suffering because memorizers, they're the most tortured souls in the world. So avoid that if all possible. Remember your talk without memorizing your talk.”
Dicks: How people land jobs is more interesting than their actual work
“Most of the time, how you get a job is more interesting than the actual job you're doing.”
Matthew Dicks: Every story should open with location and immediate action
“So two things should start every story you ever tell for the rest of your life. So you start with location. Where are you? Location activates imagination, right? If I say I'm standing in the kitchen, You've already automatically applied a thousand adjectives t…”
Dicks: People mentioning past experiences secretly want to be asked about them
“Listen for people who say things like, oh, something like that happened to me once. What they're really saying is, I wish someone would want to hear what happened to me once, and so I am always someone who's willing to say, Oh, tell me that story. Offer someon…”