Hello friend,
If you’ve ever wondered how someone ends up owning 75+ companies…
…and never raises a dime of venture capital…
This is the story.
Spoiler: It starts with coffee.
Back in 2006, I was a broke college kid designing websites to make rent.
One afternoon, I finished a client project — a café in downtown Victoria — and sent over an invoice for $2,000.
The owner called me five minutes later.
“Andrew… what the hell is this?”
I braced for impact.
Too expensive? Too fast?
“This is too cheap. You saved my business. Come in tomorrow — I’m buying you a coffee.”
That was the first time I realized…
Skills don’t scale. Systems do.
Word spread.
Uber. Slack. Amazon.
One by one, they started calling.
No press. No podcast tour. Just quiet referrals.
I kept thinking:
“This isn’t scalable. It’s not productized. It’s just a service business.”
But the invoices kept getting bigger.
And then I did something smart (by accident):
I stopped doing the work.
I hired designers.
Delegated the calls.
Documented the playbooks.
Within two years, the business was growing faster without me than with me.
That was the lightbulb.
I didn’t set out to build a holding company.
But I had this weird realization one day:
“Every boring business has the same skeleton.”
So I started buying them.
Not flashy startups.
Just… overlooked cash machines.
Tiny software tools.
Niche e‑commerce brands.
Agencies. Media sites. Even AeroPress.
Each one had a lever to pull:
Automate. Delegate. Rebrand. Remove the founder. Profit.
For years, I barely mentioned what I did.
I wasn’t a “tech founder.”
I wasn’t a “VC.”
I wasn’t “changing the world.”
I just bought boring businesses and made them better.
It didn’t sound impressive.
Until one day, someone asked:
“Wait… how many companies do you own?”
That’s when it hit me:
I’d built a quiet empire by doing the opposite of what everyone else was chasing.
Don’t get me wrong — I love money.
But what really lit me up was showing other founders how to do it.
So I started writing:
And to my surprise… people loved it.
Turns out there are thousands of us.
People who don’t want to pitch VCs.
Who don’t need a million followers.
Who just want to build profitable, unsexy, freedom-rich businesses that print cash.
Today, Tiny (my holding company) is worth over a billion.
And yet… we still follow the same exact playbook.
It works.
Not because it’s sexy.
Because it’s predictable.
I wrote this series to hand you the keys to the empire I accidentally built:
Part 1: Boring Is the New Brilliant
Part 2: How to Spot a Boring Business Before It’s Cool
Part 3: How to Run a Boring Business Without Doing the Boring Work
Part 4: The 5-Step Boring Business Blueprint
Coming next:
Part 5: How to Buy a Boring Business With No Money Down
Part 6: How to Turn One Boring Business Into a Local Empire
Each post is practical. Personal. Repeatable.
Just like the businesses I love.
I write about this stuff weekly.
No fluff. No pitch. Just real stories and simple playbooks.
Get the next boring business idea delivered to your inbox:
👉 Subscribe to the Never Enough Newsletter
Because freedom isn’t built in pitch decks.
It’s built in parking lots, pest control routes, and pressure washing margins.
This isn’t about avoiding risk.
It’s about choosing the right kind of risk.
The kind you can understand.
The kind you can improve.
The kind that stacks quietly for a decade until people wonder how you did it.
That’s boring brilliance.
Get Your Copy of Never Enough at https://www.neverenough.com
