Trick or Treat… Founder Edition - 2026 Halloween Startup Posters
Every October I shut myself in a room with a pot of happy tea, a pile of horror films and a list of everything that’s gone sideways this year. (That’s mine included, friends).
And what comes out the other end is the Oh Blimey Halloween poster series, which is roughly half daft and half a cry for help.
This year we’ve got three new posters, plus a reminder of last year’s. One is about being on your own, one is about everything looking exactly the same, and one is about a bloke in a boiler suit who won’t take the hint.
Even when he keeps DMing you about his AI playbook course.
Let’s take a look at this year’s collection.
Or read the very first series here if you’re into seeing just how much my brand has changed…
Sunset Cocktails: The Solo Founder Experience (from Widow’s Bay)
If you’ve watched Widow’s Bay, you’ll know the scene.
You’re Patricia and you’ve got something on your head. You’re in your own little world, and the noises outside are getting louder and stranger.
To me, that’s the experience of a solo founder, at least.
You’ve got your 90s playlist on and a celebratory drink because you finally ate the frog - you made progress on your Cyber Essentials certificate or your platform worked the way it was meant to on a demo call.
You’re having a lovely time.
Meanwhile your churn rate is scratching at the window and a “competitor” is rattling the door handle - getting ready to knock your “growth mindset”.
(No idea why I’m using so many ““).
The party is in full swing.
The DJ is your hype person, your dance partners are your beta testers, and the crowd in the foreground are zombies.
Dancing is allowed. Heck, Dad dancing is permitted - you’ve got to celebrate the small wins. But every so often you have to remember to take the antlers off and listen to what’s going on outside.
Heeeeeeee'res SLOPPY - The Shining
A long hotel corridor, two identical figures holding hands at the far end. You ride your little tricycle… creeping towards them.
AI slop came back this year and it brought friends. Every landing page now looks like those twins, standing in the hallway and inviting you to streamline your workflow forever and ever and ever.
Cue evil laugh, engineered using a prompt.
You know what I’m talking about.
The same headlines. The same three-icon feature grid. Same promise to unlock something that was never locked; to make something more simple that was probably already simple.
The same font, dammit.
When you’re doing the job of eight people, a tool that writes your homepage in ninety three seconds can be a big help. I get it.
The trouble is that customers can smell it.
There’s slime on the ceiling and slime on the carpet, and if your messaging could belong to any company, it belongs to none of them. People have outsourced their thinking and for some reason, given up on using voice of customer which - I think - wins every time.
But there’s a way out, friend.
It’s under the exit sign, and it’s an annoyingly analogue one: go and talk to your customers. The words they use are odd and specific, and a machine can’t fake them. It’s what helps build trust. Pinky promise.
The AI sales rep that won’t say no - Halloween
The scariest thing about the masked man in Halloween is that he never runs.
He walks. Each time you look back, he’s a little closer to the front door.
For me, that’s an incredibly effective way to describe automated outreach in 2026.
Follow-up one.
Follow-up two.
Follow-up seventeen, “hey! Gently bumping this to the top of your inbox”.
Euck.
Last week, an AI sales rep recently emailed to congratulate Oh Blimey on our Series B.
We have not raised a Series B.
We have a cartoon cat and a newsletter. Oh, and a startup game (plug plug).
The AI sales rep - who I am certain isn’t real - then followed up four times to make sure I’d seen its congratulations.
Then they invited me to an AI course.
Call me grouchy, but if the person behind the door didn’t need you on the first knock, the ninth isn’t going to change their mind.
Knowing who has the problem you solve, and why they’d care today, in my opinion (humbly) beats sending a proven playbook or whatever automated magic beans you’re promising.
So, are you scared yet?
I hope not. That wasn’t my intention.
If any of these posters hit a bit close to home, book a call with me. We can talk about the realities of launching and growing (the unglamorous ones), work out what’s actually lurking outside, or indulge in a little catharsis.
And if you enjoyed this, why not check out a previous startup halloween poster series or… if that’s still too scary, check out some more positive startup posters.
