Best Acquisitions

October 5, 2025

Why you're getting this: this is my Friends Newsletter; a place where I whisper the stuff no one puts on pitch decks.

This one’s about boring businesses.
And why they make the best exits.

If you’ve ever wondered whether your low-drama, high-margin business is worth anything to buyers like Tiny...
It is.

In fact, it might be more valuable than that VC-backed company burning $700K a month with a 14-person growth team and zero profit.

Here’s why.

The Best Acquisitions Don’t Go Viral

Every few months, someone sends me a TechCrunch article:

“Startup exits to Stripe for $87M.”

What you don’t hear:

  • They raised $80M to get there.
  • The founder walked with less than $400K after preference and dilution.
  • It took 9 years, 2 pivots, and 3 layoffs.
  • And they still ended up working at Stripe for 2 years post-acquisition.

That’s not an exit. That’s indentured servitude.

Meanwhile, someone else sells their niche SaaS for $8M—100% owned, profitable, clean—and quietly retires in Whistler.

No headlines.
No board approvals.
Just a wire and a sunset.

That’s the silent goldmine.

Boring = Buyable

Here’s why buyers love boring businesses:

Recurring revenue
Low churn
Few employees
Simple ops
No heroic founder keeping it alive

It’s not that we hate excitement.
It’s that we like predictability more.

Want to know exactly what we look for?
Read → What Buyers Like Tiny.com Look For

Profit > Potential

The big lie in startup world:

“We’re not profitable, but we’re growing!”

Cool.

We’ll come back in 3 years… if you’re still alive.

In boring business land, profit is the starting line.

Tiny will happily pay 3–5x EBITDA for a business doing:

  • $1–10M in revenue

20% margins

You don’t need a killer pitch.
Just a tidy P&L and a founder who’s not full of sh*t.

Want a cheat sheet?
Read → The Boring Business Exit Checklist

Why Boring Founders Win

Weird pattern I’ve noticed:

The best exits usually come from people who:

  • Don’t care about being famous
  • Built their business on Stripe and Notion
  • Work 20–30 hours/week
  • Don’t brag on LinkedIn
  • Send the cleanest Google Drive folders I’ve ever seen

They didn’t set out to get acquired.
They set out to build something simple, sustainable, and profitable.

Which ironically is exactly what buyers want.

The Quiet Exit Path

Here’s how most boring business exits actually happen:

  1. Founder hits $1–3M profit
  2. They get bored or tired
  3. They whisper to a few buyers (not bankers)
  4. One buyer says “yes”
  5. 45–90 days later: done deal

No bidding war.
No fanfare.
No press release.

Just a wire transfer and a clean calendar.

Want the play-by-play?
Read → What It’s Really Like to Sell to Tiny

The Irony?

You don’t have to sell.

One of the best things about boring businesses is that you can keep them.

They:

  • Throw off cash
  • Require little oversight
  • Are hard to screw up
  • Fund your next idea (or your retirement)

Which means you can hold them forever.
Or sell when you’re ready.

Optionality = leverage.

VC startups have to exit.
You get to decide.

Final Thought

Boring is beautiful.
Simple is scaleable.
Quiet is valuable.

If you’re building a boring business; good.

You’re sitting on the kind of company most buyers pray for:
No drama.
High margin.
And totally off the radar.

If you want to sell it someday, you won’t need a banker.
You’ll need a buyer who gets it.

And if that’s you?

You know where to find us.

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

Or don’t.
Just go raise your margin and enjoy your peace.

—Andrew

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