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- Most founders are terrible storytellers (are you?)
Most founders are terrible storytellers (are you?)
I audited my old content and cringed
Stephen Stanberry
July 31st, 2025
In partnership with
friend, friend, friend
I thought I was a decent storyteller.
I was dead wrong.
Last month, I went back and read my old content from 2021.
Holy crap, it was terrible.
I was sharing random stories about my radio days, and my freelance struggles.
No point. No lesson. No reason for anyone to actually care.
Just me word-vomiting my life onto the internet (yikes).
That's when I created The Storytelling Audit (the prompt is at the end) - 4 questions that exposed why my stories were getting zero replies:
→ Are you connecting or confusing?
Old me: Dumped my entire career story in one post.
New me: One specific moment that mirrors my audience's struggle.
Your story should make people think "That's exactly how I feel" - not "Cool story, friend."
→ Are you teaching or therapy-ing?
Old me: Just vented about getting fired without any lesson.
New me: Every struggle comes with a takeaway.
If your story doesn't teach something, you're just processing trauma in public (expensive therapy).
→ Are you the hero or the guide?
Old me: Made myself the success story.
New me: Made my audience the hero of their own journey.
Your story should be the bridge that gets them from struggle to success.
→ Are you closing loops or leaving gaps?
Old me: "Anyway, that's my story. What do you think?"
New me: Every story ends with something they can actually use.
I know, I know. You're thinking: "Stephen, this sounds obvious."
It is.
But most people still get it wrong.
Here's what happened when I fixed this:
My engagement went from crickets to conversations.
Same stories. Better structure.
People started replying with their stories instead of just scrolling past.
Big difference.
Your turn:
Grab your last 3 posts.
Run them through this audit.
Be brutally honest.
(I failed 3 out of 4 questions on most of my old content.)
Most people's stories are just therapy sessions without the lesson.
But you? You're about to start telling stories that actually matter.
Look, your stories don't suck.
Your structure does.
And if you want the exact frameworks that turned my random life updates into stories people actually engage with...
"Love, Learn, and Live Storytelling" has all the templates I wish I'd had in 2021.
For $7
(Way cheaper than the therapy I was accidentally doing in public.)
Simple, right?
From my much-improved storytelling journey,
Stephen
P.S. The difference between a story that works and one that doesn't? Structure beats everything. Fix the framework, fix the engagement.
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