My girlfriend's mom and brother are terrible storytellers.Â
Her mom starts halfway through the story and leaves out all the context necessary to remotely know what she's talking about.
Her brother starts a mile before the story and tells you way too much context, and you're left wondering what the point of all that was.
Here's how they (and founders) should tell stories.
â Neal
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This week's tactics
Start with getting slapped by a baguette
Insight inspired by Storyworthy by Matt Dicks.
âThe waiter slapped me across the face with a baguette, and I didnât know why.â
This opening line to a story is significantly better than the more commonly used, âmy vacation to Paris was a disaster.â
But why?
They both induce curiosity and beg a follow-up question.
The problem with the second, more general one is that only someone who cares about the person speaking would bother to ask a follow up.
Itâs simply too risky.
You might be about to receive a banal story about waiting in lines at the Eiffel Tower or a French person being rude to you for speaking English.
The first, however, puts you right into the action of a specific moment
Your brain instantly paints the scene:
- You see the cute French café
- You see the waiterâs outfit
- You see his funny mustache.
- You see him swing a baguette across the personâs faceÂ
Itâs tangible. Itâs hilarious.
And then it leaves you with a mystery.
âWhat do you mean you didnât know why he slapped you with a baguette? What happened?â
Youâre hooked. Youâre invested.
Better yet, youâll be miserable if you donât hear the conclusion.
This is what Matt Dick calls âAnchor in a specific momentâ in his book Storyworthy.
And itâs precisely what you need to get people invested in your stories.
Why anchoring in a specific moment works
#1. Clarity for the listener/reader:
A specific moment helps your audience visualize whatâs happening immediately. It gives them something tangible to latch onto rather than vague descriptions.
It also removes the risk of asking a follow-up question to a generic opener. Theyâre already hearing the story and know that theyâre interested.Â
#2. Eliminates rambling
When you anchor your story in a moment, you avoid rambling on about random details that matter to you but donât matter to the storyâstarting with a clear "where and when" lets you get to the interesting bits faster.
This is what Wes Kao calls finding the âMinimum Viable Backstoryâ when she recommends, âStart right before you get eaten by the bear.

#3. Creates a sense of time and place:Â
Anchoring helps orient the audience. They immediately know where they are, when this is happening, and often whatâs at stakeâpulling them into the story.
How to anchor effectively
- Start in the middle of the action: Open your story by describing something happening right now rather than explaining what led up to it.
- Example (weak): "When I was in college, I used to do a lot of embarrassing things."
- Example (strong): "I was standing on a cafeteria table, pantsless, holding a loaf of bread over my head like a trophy."
- Use the five senses: Use sensory details to help the audience see, hear, or feel whatâs happening.
- "The cold metal of the handcuffs clicked shut around my wrists."
- Avoid broad generalizations: Sentences like âIt was a normal day, until....â or âLife was goodâ are too abstract (and clichĂ©). Be specific and drop us into the moment that matters.
- Don't make me wait: Every story is about a transformation. The opening anchors us as close to that moment of change as possible so we can follow the journey.
Letâs dissect a famous example
âNot for the first time, an argument had broken out over breakfast at number four, Privet Drive.â
Here's what's powerful about this opener to the Chamber of Secrets:
- Economical and direct: One sentence sets the scene, introduces conflict, hints about whoâs involved and perhaps what itâs about, and establishes a pattern (this happens often).
- Immediacy: Weâre thrown straight into the argument, bypassing unnecessary description.
- Colorful writing: Starting with ânot for the first timeâ makes the sentence stand out and frames it in a negative (leaning into the Negativity Bias)
- Specificity: âNumber four, Privet Driveâ anchors the story in a precise locationâthatâs well known to fans, so they instantly know who might be wondering and start wondering what theyâre arguing back this time.
 Itâs a powerful opener thatâs doing a lot of work in a short amount of time.
âBut Iâm a startup founder. What do I care about telling stories!??â
Because humans are obsessed with stories and narratives:
- Christmas is a story.
- The concept of what âThe United Statesâ is is a story.
- The rising popularity of personal branding is a story.
- Bitcoin, gold, and money are shared narratives and concepts that have value because we believe that story.
- The US dollar goes up because people start believing a story that people start spreading because of Trump getting elected who got elected because of stories he and others told about him and the future that would unfold if he was elected.Â
- Teslaâs stock shoots up because Elon tells a story of a future where people donât need to own cars because thereâs a fleet of autonomous cars driving everyone around for super cheap.
- He first told this story back when the tech wasn't remotely close to doing that, but he sold the dream, which helped keep the company afloat long enough to the moment when we were getting close.
Stories are powerful.
Use stories to your advantage to:
- Sell your product
- Get investors
- Convinces people to invest years of their career at your startup
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Something fun
Something fun
After incessant playings of Taylor Swift and Christmas songs during my last visit to Vancouver (during Taylorâs final weekend of the Eras tour), I can strong relate.
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â Neal &Â Justin, and the DC team.