Never Tell, Always Storytell

September 20, 2025

Hello friend,


Why you're getting this: This is my Friends Newsletter; a weekly signal flare from the trenches of business, creativity, and weird founder psychology. Some weeks it’s a framework, other weeks it’s a confession. This one’s both. Unsubscribe anytime (just don’t tell me why).

Here’s what I’m thinking about…

Never Tell, Always Storytell

This is the mantra I repeated; over and over, at my Interesting People event this year:

Never tell. Always storytell.

Whether you’re:

  • Pitching an investor
  • Leading a team
  • Selling a product
  • Writing a newsletter
  • Convincing your kid to brush their teeth...

The story wins. Every time.

Nobody Cares About Your Slide Deck

I’ve sat through hundreds of startup pitches.
You know the ones:

  • Slide 1: TAM is $84 billion
  • Slide 2: “Uber for goats”
  • Slide 3: Hockey stick
  • Slide 4: Team of ex-Google ex-Meta MBAs
  • Slide 5: “Just need $5M to scale”

I forget all of them.

But I still remember the founder who said:

“I was a single mom who got screwed by payday lenders. So I built an app to destroy them.”

I was in.
Before the spreadsheet.
Before the deck.
Before the demo.

Because the story made me care.

The Numbers Don’t Stick. The Narrative Does.

This applies everywhere in business.

  • Fundraising
  • Internal memos
  • Onboarding
  • Sales calls
  • Vision decks
  • Culture docs
  • Launch emails
  • Hiring pages
  • Press releases

If you lead with facts, you’ll bore them.
If you lead with story, you’ll move them.

People remember beginnings, turning points, and endings.
They remember tension and triumph.
They remember people, not percentages.

Steve Jobs Didn’t Launch the iPod With Specs

He didn’t say:

“This is a 5GB MP3 player with FireWire sync.”

He said:

“1,000 songs in your pocket.”

That’s story.
That’s human.
That’s sticky.

Elon Musk Is a Walking Sci-Fi Plotline

You might love him or hate him; but you remember him.

Why?

Because everything he does has narrative baked in:

  • Colonizing Mars
  • Freeing Twitter from tyranny
  • Saving humanity from AI
  • Launching cyberpunk trucks with sledgehammers

He doesn’t market features.
He markets myths.

The Memo That Changed Everything

A few years ago, I wrote a memo to a struggling team at one of our companies.

Normally I’d open with “metrics are down,” “we need to refocus,” “Q4 targets,” etc.

This time, I told them a story:

About a small group of misfits who built something people loved.
Then lost the spark.
Then found it again by going back to the customer.
About why what they were building actually mattered.
And what it could still become.

The response?

More engagement than any town hall I’ve ever done.
One guy emailed: “I cried at my desk. I needed this.”
The team turned it around.

Not because of data.
But because the story lit the fire again.

I Write Everything As a Story Now

  • Investor updates
  • Founder onboarding docs
  • Sales pages
  • Job listings
  • This newsletter

If you’ve ever wondered, “why does this feel different?”—it’s because I treat it like storytelling.

Not a broadcast.
Not an essay.
Not a report.

A story.

Want to Be a Better Leader? Learn to Tell Stories

Seriously.

Learn how to:

  • Create tension
  • Share vulnerability
  • Make people care
  • Show the stakes
  • Give a satisfying arc

No one remembers the founder who said “our NRR is 112%.”
They remember the one who said “I almost shut it down; and then this happened…”

Other Updates

Still writing Never Enough 2.
More stories. Fewer diagrams.

Just joking!

Still evaluating deals.
If you can tell me why your business matters in 3 sentences, I’ll probably keep reading.

Still hiring storytellers.
Not marketers. Not MBAs. Just humans who can make other humans feel something on the page.

FAQs

1. Isn’t this manipulative?
No. It’s called being human.

2. Should I just skip the data?
No. Back up your story with truth. But lead with heart.

3. What if I’m not a writer?
Learn. Or partner with someone who is.

4. Do you still use decks?
Yes—but only after the hook has landed.

5. Isn’t storytelling just branding?
Branding is the wrapper. Storytelling is the soul.

6. Where should I start?
Tell the story of why you started. It’s always the best one.

7. Should I tell the same story over and over?
Yes. Especially if it’s true.

8. What about investor updates?
Make them a story arc. Hero’s journey. Even if the hero gets punched in the face.

9. How do I practice this?
Write your pitch like it’s a movie. Edit ruthlessly.

10. What’s the most powerful story you’ve told?
This one: “I thought money would make me happy. It didn’t.”
For that one, read this.

That’s all for now…
You don’t need better metrics.
You need a better story.

Get Your Copy of Never Enough at https://www.neverenough.com

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