Keep telling your brand story like that. See what happens.

_{Day 54/100}

Hey - It's Tim.

There are only two types of founder stories.

The ones people repeat at dinner.

And the ones nobody remembers.

Most land in the second group.

Not because the founder was boring.
But because they told the story like a LinkedIn post.

Polite.
Optimized.
Sanded down to nothing.

I’m not here for that.

Let me show you how to tell a story people actually talk about.

The Mistake Most Founders Make

They think they're telling a brand story.

But really?
They're writing customer fanfiction.

It's too safe.
Too polished.
Too generic to care about.

And so they swing too hard in either direction:

There’s a middle ground.
I call it: Protagonist Syndrome Done Right.

Rule #1: The Founder Is The Player Character — Not The Final Boss.

You're not Yoda.

You're not Gandalf.

You're Frodo with a broken flashlight and a map you drew on a napkin.

That's who people root for.

Nobody roots for someone who skipped the hard levels.

Action: Write Your Founder Origin Like A Save File

Here’s the prompt I use for myself and clients:

The smaller and more technical the better.
Show you're in the trenches.

Examples:

• Failed product launch stories nobody saw.

• Writing 100 blog posts nobody read.

• Losing money on a PPC experiment because you didn’t set exclusions.

Make it hurt. That’s where the trust lives.

Rule #2: Show The Cost Of The Win.

Most brand stories sound like this:

That's not a story. That's a press release.

A story is:
→ Here's what it cost us.
→ Here's what almost broke us.
→ Here's why we could’ve quit... but didn’t.

Action: Tell The Story Backwards.

Write your biggest "win" as a near-death experience.

Example:

That's way more compelling than:

Rule #3: Be A Bad Influence (In A Good Way)

Most founder stories try to teach.

Way cooler to corrupt.
Way cooler to tempt people into doing the thing you did - because it was messy, stupid, real.

Action: Plant Seeds Of Chaos In Your Content.

Little lines that dare the reader to copy your bad idea.

Example:

This is founder energy people remember.

Rule #4: Label The Lessons People Can Steal.

Nobody remembers generic advice.

People remember weird little phrases.

Because language sticks before logic does.

When you give something a name, you make it feel real.
Like you didn’t read it in a book - you bled for it.

Action: Brand Your Scars.

Look at the dumb stuff you’ve done building this thing.
Look at the patterns you’ve lived through.

Name them like inside jokes for your future customers.

Examples I’ve seen or used:

• "Ugly Growth" - When the early version of your product looks like garbage but works anyway.

• "The Quiet Stretch" - Those slow, awkward 6 months where nothing goes viral, but everything compounds.

• "Launch Fog" - The 3-day period post-launch where your brain is broken and Slack is chaos.

That’s the game.

Label it.
Make it yours.
Watch people repeat it back to you later.

Rule #5: Leave Crumbs For Your Future Biggest Fans.

Most people write content for who’s watching today.
That’s fine.
But the best brands? They leave little crumbs everywhere for the people who’ll show up years later.

A weird detail here.
An Easter egg there.
A phrase that sticks.
A blog post nobody read... until it mattered.

These things compound like crazy.

Because surface-level audiences come and go.
But people who find your crumbs?
They stick around forever.

Action: Bury Signals In Your Content.

Here’s what this looks like in practice:

• Give your community a name before it feels big enough.

• Mention your weird hobbies or obsessions regularly.

• Refer back to old stories without explaining them fully.

• Leave “if you know, you know” jokes in the footer.

This is slow growth magic.

It makes people feel like they joined a secret club.
It turns casual readers into career-long fans.

I didn’t realise this until I started writing every day...

But the people who care the most about your brand?
They’re the ones quietly reading everything.

Not the likes.
Not the comments.
Not the shares.

It’s the quiet ones in the back row saving every post.
Bookmarking. Forwarding.

Future superfans don’t announce themselves.
They binge your archive in 3 years and tell you they remember a random line from email #17.

So write like that person exists.

Because they do.

I’ve already had people reach out to tell me they are that person. They have made it their personal goal to read every newsletter.

_{I have one person who replies to every newsletter. Shout out Maria. You’re a real one.}

Final Thought:

If you feel like your founder story is boring...

Good.

It probably means you’re telling the truth.

Boring builds trust.
Mistakes build trust.
Process builds trust.

And every so often — a little main character energy doesn’t hurt either.

✌️ Tim "Main Character Energy" Hanson
CMO @Penfriend.ai

P.S. If you’ve been reading these emails for a while — you’re already part of the story I’m telling with Penfriend.ai 

The best stuff I’ve written?
Honestly... it’s probably buried in email #14. Or #32. Or tomorrow’s.

That’s how this works.

Slow compounding.
Bad ideas getting better.
Little crumbs turning into something bigger.

I’ve been thinking about setting up a little reward system.
Something fun. Stupid. Personal.

If you send this newsletter to a friend — or a few friends — I want to find a way to say thanks properly.

Maybe it’s private content.
Maybe it’s dumb merch.
Maybe it’s a handwritten letter from me trying to be funny on purpose (dangerous).

If that sounds like something you’d be into — hit reply. Tell me.

I’ll figure it out.

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