Entrepreneurs

The Businesses That Make Sensible People Uncomfortable

By RebelandReason

There’s a certain kind of business that makes sensible people twitch.

Not illegal.
Not immoral.

Just… wrong somehow.

The sort of idea that gets polite smiles in meetings and the phrase:

“Interesting concept, but I’m not sure the market is there.”

Then five years later it’s everywhere and everyone pretends they saw it coming.

I’ve become mildly obsessed with these businesses because they nearly always start the same way. Someone notices a rule that everybody else is following and quietly decides the rule might be nonsense.

Take 1-800-GOT-JUNK?.

Before that company came along, junk removal wasn’t really an “industry”. It was just blokes with vans. The kind of service you found on a faded magnet on a fridge or a scribbled phone number on a lamppost.

Then Brian Scudamore turns up and does something that looks obvious in hindsight. He treats it like a proper consumer brand. Memorable name. Clean trucks. Staff in uniforms. Central booking.

Nothing revolutionary.

But suddenly junk removal looked like a business instead of a favour you asked someone’s cousin to do.

Same service. Completely different perception.

Another example I always enjoy is the art marketplace Witchsy.

Its founders, Penelope Gazin and Kate Dwyer, discovered something slightly depressing while pitching investors.

Emails and meetings went noticeably better when investors thought there was a male founder involved.

So they invented one.

A fictional co-founder called Keith Mann started appearing in emails and pitch decks.

Responses improved immediately.

Eventually they admitted the joke publicly, which made the story even better because it exposed a bias everyone suspected but nobody wanted to say out loud.

You could call that deception.

Or you could call it a very efficient experiment.

The pattern behind these stories is surprisingly consistent. The founders aren’t necessarily the smartest people in the room. What they tend to be good at is noticing strange behaviour inside systems everyone else takes for granted.

Why does this industry still look like 1997?

Why does nobody brand this properly?

Why do customers tolerate something this inconvenient?

Most markets are basically habits wearing suits.

Once you notice that, business becomes a lot less mysterious.

Another thing interesting companies often do is sell identity rather than product.

Think about brands like Supreme or Patagonia.

People aren’t just buying clothes.

They’re buying a signal.

A small message about who they think they are.

That’s why these businesses grow in ways analysts often miss. Customers do the marketing because the brand doubles as identity.

Inside conservative industries this behaviour looks rebellious.

Outside those industries it just looks obvious.

And that’s usually where the interesting businesses come from.

Not from dramatic disruption.

Just from someone quietly looking at a normal industry and thinking:

This seems a bit stupid.