Never Enough

Hello friend,

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Why you’re getting this: this is my Friends Newsletter, a brain dump I send to interesting people I’ve met and want to keep in my orbit.
Zero pressure to stick around; unsubscribe anytime.
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I’ve been thinking about unsexy businesses and why they print money while everyone else chases clout.

Here’s what I’m thinking about…

I used to assume the best opportunities were hiding in some clever product I hadn’t thought of yet.
A magical app.
A shiny trend.
A press‑friendly story.

Then reality smacked me with a squeegee.
Boring businesses quietly win.
They win because nobody’s paying attention.
They win because they serve needs, not narratives.
They win because the customers don’t care about your pitch deck; they care about the job getting done.

I call it “Fish Where the Fish Are: The Boring‑Business Goldmine.”
Not cute.
Not clever.
Just true.

When I tell people the safest bet in the entrepreneurial casino is a dull, recurring, slightly annoying problem, their eyes glaze over.
They want crypto‑AI‑VR.
They want “platform.”
They want the dopamine hit of being early.

But “early” is expensive.
“Obvious” is profitable.

I’ve watched founders burn years chasing sexy markets where everyone else is also burning years.
Meanwhile, the quiet killers keep showing up, answering the phone, and compounding.

I helped a student start a pressure‑washing company.
First month, we did $20,303.
Was it glamorous?
No.
Did it work?
Yes.
For the story, see my blog post: I made $20,303 power washing driveways

“Okay Andrew, what counts as boring?”
Think pest control, septic, washroom supplies, form‑filling software, signage, bulk labels, claims processing, HVAC service.
If a tech bro would mock it on Twitter, you might be onto something.

Why these markets rule:
They’re annoying to enter.
They require licenses, relationships, trucks, SOPs, early mornings, and dirty hands.
Translation: a moat made of inconvenience.
VCs won’t touch them because they can’t 100x on a deck.
Perfect.
Leave them to us.

A quick deal filter I use:
Recurring need.
Low churn.
Unsexy category.
Owner‑operated 20+ years.
Margins north of 25%.
Marketing spend near zero.
Obvious upside from basic digitization.
If I can make it 20% better with standard blocking and tackling; answer the phone, show up on time, invoice cleanly; I lean in.

You don’t need to be passionate about roofing tar.
Be passionate about margin, time, and optionality.
Work a boring business for three years and you’ll buy the freedom to chase any passion you want.
That’s the cheat code nobody likes because it isn’t romantic.

Here’s a trick.
Start narrow enough to be embarrassing.
Not “all healthcare.”
Try “endodontists in Saskatchewan.”
Own one zip code.
Win the map pack.
Answer every call.
Then expand.
The riches are in the niches because niches have names, and names pick up the phone.

Customer acquisition is easier in “boring” because intent is real.
Run ads for a termite inspection and you’ll book work tomorrow.
Run ads for your visionary social app and you’ll get… feedback.

Another trick.
Sometimes the “software” opportunity is service wearing glasses.
People don’t always want an app.
They want a human who answers and a paper invoice that makes sense.
Be the human.
Mail the invoice.
Collect.

The best part of boring is the social camouflage.
Nobody asks you for hot takes.
Nobody screenshots your ARR chart.
You get to improve operations in peace.
You get to compound without critics.

I’ve met founders quietly running $5M–$30M businesses you’ve never heard of.
One sells compliance form‑filling software into HR.
Another prints hospital signage.
Another shreds documents.
No hype.
Just cash.

What I look for when we buy:
Tired owner.
Healthy business.
Simple model.
Reputation you can’t fake.
Hidden levers like pricing discipline, route density, recurring contracts, and basic CRM adoption.
Pull those and watch EBITDA breathe.

“Isn’t that… small?”
Good.
Small is where you learn to make real money.
Small breaks cleanly.
Small forgives mistakes.
Small is the gym where you get strong.

If I had nothing tomorrow, I wouldn’t pitch a fund.
I’d buy a plumbing shop.
I’d standardize quotes, clean up the brand, install a CRM, optimize routes, implement next‑day follow‑ups, and train techs to upsell without being annoying.
Twelve months later it would look “lucky.”
Luck is just operations in a trench coat.

Start local.
One neighborhood.
One boring problem.
One great Google Business Profile.
Own that block, then the next one.
Yes, it’s slower than a Series A.
It’s also yours.

The contrarian part is emotional.
Can you stand being uninteresting at dinner parties for two years while you get rich?
Can you say, “We do washroom supply and we’re hiring,” without apologizing?
Can you ignore the founders chasing teatime on CNBC?
That’s the test.

A few I’d start tomorrow if I had the time:
Niche landscaping roll‑up with tight route density.
Mobile dog grooming with ruthless scheduling.
Pool maintenance with prepaid plans and seasonal add‑ons.
ID badge printing with on‑site service contracts.
Junk removal with a local SEO machine and next‑day guarantees.
If you build one of these well, email me.

If you want a neat bow, here it is.
Fish where the fish are.
Stop hunting for permission to be impressive.
Solve a guaranteed problem for a specific person and send an invoice that gets paid.
Do it again next month.
Do it again next year.
That’s how boring becomes beautiful.
That’s the boring‑business goldmine.

Other Updates
I’ve been saying no more.
It feels like free money.
Tiny is prioritizing recurring revenue over heroics.
Boring, steady, compounding.
The adult table.
I’m also interviewing an AI ops nerd to automate the sludge in my life.
Email triage, calendar prep, vendor nudges, CRM hygiene.
Send me a Loom if you’ve built something that makes humans obsolete in a kind way.
And yes, the pressure‑washing project is hiring.
If you’re in Victoria and love early mornings, reply.

Reading / Watching
Re‑reading Buffett’s shareholder letters.
Still undefeated.
Listening to old Beatles deep cuts because I am a cliché with speakers.
Trying not to buy another ridiculous keyboard.
Failing.

That’s all for now.
Go do something unsexy and cash‑rich.
I’ll cheer for you from the trench.

Get Your Copy of Never Enough at https://www.neverenough.com/

P.S. For more on rolling up your sleeves and touching reality, see my blog post: I made $20,303 power washing driveways.
P.P.S. If you ignored everything above and still want a “big idea,” start with “Fish Where the Fish Are: The Boring‑Business Goldmine.”

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That's all for now…

-Andrew

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Fish Where the Fish Are: The Boring-Business Goldmine