How to Spot a GOOD Boring Business

September 21, 2025

Hello friend,
Why you’re getting this: you’ve either built something boring already, or you want to.
Either way, you’re my people.

Let’s talk about how to find the next HVAC before the MBA crowd starts podcasting about it.

Here’s what I’m thinking about…

We Need to Talk About Shoe Stores

In 2014, I tried to buy a local shoe repair shop.

Tiny storefront.
Peeling paint.
Smelled like glue.

But here’s the thing:

Every time I passed by, there were people lined up.
No marketing. No online presence. Just loyal repeat customers.

I asked the owner how business was.

He leaned in and said, “I haven’t paid for advertising in 15 years. I turn away work.”

I offered to buy it.
He said, “Only when I die.”

That’s the dream.

Boring Businesses Don’t Start Boring

They start as overlooked.

Then someone with good taste and bad patience walks by and sees the cash stuck inside.

That’s what this post is about:
How to spot a boring business before it becomes “a good idea.”

Because once it's on a podcast, it’s too late.

Look for Loiterers

Every boring business I’ve ever wanted had one thing in common:
People standing around awkwardly.

Waiting rooms.
Pickup lines.
Backed-up driveways.
Missed calls on a whiteboard.

Why? Because demand > supply.

That’s all you need.

Search for the Underwhelming

I love a good brand.
But when a business has Comic Sans signage and still has five-star reviews?

That’s a clue.

It means the service is good enough to survive terrible taste.

Which also means if you add even basic operational or design sense, you win.

Listen for Sighs

Your aunt complaining about her appliance repair guy being late for the third time?

That’s signal.

Every sigh is a business idea.
Every Yelp rant is a gap in the market.

When people keep paying despite bad service, you’ve found your wedge.

Find the Dust

Literally.

Go look at the shops with the dustiest windows and oldest inventory systems.

If the owner still writes invoices by hand and has no website?
You're staring at margin waiting to be modernized.

I once saw a shop that made $900K/year with no computer.
Just sticky notes. And rage.

Look for Work Trucks Without Logos

Unbranded truck.
Hand-painted number.
No website.

That guy’s probably clearing $250K.

The moment someone has more clients than they can handle and no incentive to grow, they plateau.

Your job is to catch them right before they do.

Ask “Who Would Be Annoyed If This Business Shut Down Tomorrow?”

If the answer is “a lot of people,”
and nobody is bragging about it on Instagram…

You’re onto something.

Pain + loyalty = boring gold mine.

The Craigslist Test

Craigslist is a graveyard of good ideas run by tired people.

Find a listing with:

  • Bad photos
  • Vague description
  • No financials

Then call the seller and ask:

“How many customers are recurring?”
If they say anything above 40%, meet them.

Watch the Weather

Storms, heat waves, and cold snaps = phone calls.

If a business gets flooded with demand when things go wrong (and they do every year), it’s recession-proof.

Think:

  • Emergency tree removal
  • Broken AC
  • Ice dam repair
  • Basement flood cleanup

Seasonal pain is predictable margin.

Look for Regulation (That Doesn’t Change Often)

When the government says “you must do this every year,”
someone gets rich.

Fire extinguisher inspections.
Dental equipment sterilization logs.
Hood vent cleaning.

Compliance is a cash register.

Follow the Fridge

If a building has a fridge, it has:

  • Condenser fans
  • Gaskets
  • Compressors
  • Filters

All of which break.
And someone has to fix them.

Restaurants, grocery stores, labs.
Refrigeration techs don’t post on LinkedIn — they’re too busy making $180/hr.

Go Where MBAs Fear to Tread

Here’s a fun trick:
Go to a startup founder dinner.
Pitch “commercial window washing.”

If no one bites, start it.

If everyone laughs, double down.

If one person says, “We’re doing that, but with AI,” run.

Follow Gross Before It Becomes Glamorous

Power washing was gross.
Now it’s on TikTok.

Gutter cleaning was gross.
Now it's a franchise.

Poop scooping was gross.
Now it’s on Shark Tank.

The lesson?

The earlier you spot gross, the more you own it before it’s glamorized.

Pay Attention to Vendors, Not Just Customers

I once met a guy who only sold replacement belts for restaurant slicers.
He made $700K/year.

How?
Because he was the only person who followed up every 90 days.

Your customers might not be sexy.
But their vendors might be boring goldmines.

Reverse Engineer the Craigslist Gigs Section

If 12 people are posting “Need junk hauled TODAY,”
then junk hauling is not saturated — it’s fragmented.

Look for niches where demand is high and no one’s dominating.

Ask Your Grandparents

Seriously.

They remember:

  • What breaks
  • What’s hard to fix
  • What nobody wants to do

Old problems = new business ideas.
Especially if no one has updated the process since 1977.

Check What Breaks in Airbnb Units

Short-term rentals expose where things wear out.

If hosts are replacing something every 3 months, and there’s no easy subscription to handle it?

You’ve got a business.

Find the Local Monopoly Everyone Hates

There’s always one.

  • The only plumber who answers the phone
  • The only dog groomer in town
  • The only company who’ll haul away mattresses

They’re ripe for a friendly competitor who shows up and smiles.

Look for Paper and Clipboards

If someone is still using clipboards in 2025, they’re behind.

If you can digitize just one part of their workflow (quoting, dispatch, invoicing), you can:

  • Save time
  • Win business
  • Resell it as a SaaS or service

I did this in one of my businesses. It felt like cheating.

The “Embarrassment” Edge

If someone feels embarrassed to say what they do, lean in.

The worse it sounds at a dinner party, the better it probably pays.

Pest control?
Poop hauling?
Hoarder cleanup?

Yes. Yes. Yes.

Follow the Yelp Reviews That All Say the Same Thing

If every 5-star review says “Finally someone who answered the phone…”

That’s a market problem, not a customer fluke.

A boring operator who simply responds can steal the whole category.

The Trick Is Not Waiting for Permission

By the time everyone’s writing Twitter threads about a boring business?

You’re already late.

The best time to get in is when it’s so boring, even you hesitate to say it out loud.

That hesitation?
That’s the scent of margin.

FAQs

1. What’s the best way to validate a boring business?
Call the top 3 providers. If they don’t answer or are booked out, it's real.

2. Where do I find these businesses?
Drive around. Ask friends. Look at what annoys them. Craigslist. Local Facebook groups.

3. What if I don’t want to operate it?
Find a hungry operator. Pair your capital and systems with their energy.

4. How do I know it’ll scale?
If it’s fragmented, service-based, and has recurring pain, it can scale.

5. Do I need experience?
No. You need taste, empathy, and the willingness to learn (and ask dumb questions).

6. Should I build or buy?
Buy if possible. You skip the hardest part — traction.

7. Isn’t this risky?
Not if you move slowly, verify demand, and stay lean.

8. What’s the margin like?
Often 30–60%. Because no one wants to compete.

9. How do I spot a fake boring business?
If everyone in your cohort suddenly wants in?
It’s probably not boring anymore.

10. What should I read next?
See: I Made $20,303 Power Washing Driveways

Conclusion

Boring businesses are easy to miss.
Because we’ve been trained to ignore them.

But if you start looking — really looking — you’ll spot them everywhere.

It’s the dry cleaner with a handwritten sign.
The guy fixing elevators who never posts online.
The grandma who sells firewood by the bundle and clears $90K/year.

They’re not trying to look smart.
They’re too busy being rich.

Want more?
Subscribe to the Never Enough Newsletter or read About Me if you’re new here.

And get your copy of Never Enough at https://www.neverenough.com

The Never Enough Newsletter
Sign up for Andrew's weekly newsletter for insider tips, reflections, and personal tool recommendations.
Enter your email and
sign up for free right now.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.