- Tim at Penfriend
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- Boring dies quietly. You're not boring are you?
Boring dies quietly. You're not boring are you?
Cheeky tooltips, voice-note support, bug-hunt swag. Start tonight, magnetise tomorrow.

Day 148/100
Hey—It's Tim.
“Holy sh*t, that brand follow the best practices so hard”.
You product isn’t boring. You are. Well, maybe not. But your outputs are.
You’re being far too reasonable. And therefore, you’re boring.
Before you gather the pitchforks. Lemme explain.
I spent last night doom-scrolling product launches.
Same slick mock-ups.
Same AI-generated smiles.
Same beige “innovation.”
Carl Jung wouldn’t have clicked any of it. His rule:
“Know every theory, master every technique—but, as you touch a human soul, be just another human soul.”
I’m guilty of this a hundred times over.
And it’s something I’ve been thinking about a lot.
“People don’t fuck with perfection”
We pretend polish equals trust.
Wrong.
Trust is the ding in your watch that reminds you of the night you almost lost it.
Trust is the chipped mug you refuse to replace.
Perfection is sterile. Connection is sticky.
Want a sticky product? Leave a fingerprint - and sign it in Sharpie.
Personal proof: When we shipped Penfriend’s earliest beta, we did a livestream to introduce it. The video stuttered like my old dial-up modem. Users emailed… praise.
Why? Because the glitch proved there were real humans behind the curtain - humans who cared enough to ship before they were “ready.”
Glitch > gloss. Every. Single. Time.
Give it a pulse
Talk human first, tech later. Ask users what keeps them up, not which feature they want.
Ship the draft, not the dissertation. Let the crowd throw tomatoes, then tighten the show.
Swap KPI for KFI—Killer Feeling Index. If no one screenshots it for their group chat, iterate.
Spark the trust loop
Trust isn’t built in a funnel; it’s built in a heartbeat. Each “wow” moment sparks a micro-loop that looks like this:
1️⃣ You surprise me → I feel seen → I brag about you → My friends show up → You surprise them.
Repeat until your server chokes on referrals.
How to spark your own loop tonight:
Hide a human in the machine.
A cheeky tooltip, a self-deprecating Easter egg, a “call the CEO” button that actually rings your phone at 3 a.m. (ask me how I know).Answer DMs like voice notes.
Text is cold; voice is warmth bottled. Ten seconds of raspy authenticity beats a thousand-word FAQ.Ship a bug with a wink.
Deliberately mis-color one icon, then add a “Report the oddball, win swag” prompt. Bugs become bonds.
If you’re boring, you’re invisible. If you’re memorable, you’re magnetic.
Start ugly, iterate louder
If I were launching today (and remember, we are very soon…)
I’d do three things and nothing else:
Ship a half-baked demo by Friday. Not a landing page-an interactive toy users can break. Put a giant “Roast Me” button on it. The internet will hand you a free roadmap overnight.
Open a Discord before you write copy. Sit in the general channel like the world’s sweatiest bartender, pouring refills of attention and stealing every complaint for tomorrow’s sprint.
Hard-code one Easter egg per build. A 404 that drops the Konami Code, a tooltip that flirts back-whatever. If the release notes don’t spark a screenshot DM, recycle the build and add soul.
Perfect comes last. Loud, lumpy progress comes first.
Give until it aches
Unknown brands can’t hide behind paywalls, so out-give the room:
Core feature? Free for 30 days-no card, no FOMO timer.
Scarcity is a luxury once you’re already loved.Founders’ inbox in the onboarding flow.
Promise a personal reply within 24 hours. Yes, your thumbs will melt; the replies are market research in raw form.Publish every misstep as a devlog.
Public failure buys more trust than private success.
Generosity is gravity. The more you throw into the world, the heavier your orbit becomes.

✌️ Tim "Break-the-Simulation" Hanson
CMO @Penfriend.ai
Same brain, different platforms: X, Threads, LinkedIn.
P.S. Tell me what keeps you up at night with content creation and I’ll do my best to make a product that fixes that. Or a newsletter to go over what I would do.

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