A few years ago, I sold a business over lunch.
No bankers. No CIMs. No NDA until after dessert.
Just two people, an iPhone calculator app, and a handshake.
That’s what I love about quiet acquisitions.
They’re clean.
They’re fast.
And if done right, they feel less like a divorce and more like giving your kid to someone who won’t screw them up.
So if you’ve ever asked yourself “Is it time to sell?” here’s how I’ve known I was ready (even if I pretended I wasn’t).
You’re on calls, nodding, pretending to care about conversion rates, when really you're thinking about that pasta place in Rome.
That’s your body telling you: you're done.
The irony?
You only get these feelings after you’ve built a solid business.
If the business is boring but profitable, and runs mostly without you, congrats; you’ve built the thing buyers want.
Now you just need to admit it’s time to go.
This is the gut punch.
You spent 5 years duct-taping this thing together, and now it runs beautifully; and you’d rather be doing literally anything else.
That disconnect?
It’s not burnout.
It’s the beginning of your exit story.
And if you’re still stuck on whether you can leave it behind, read I Want You to Hate Me for a nudge.
You know the one.
You see an email with the subject line “Acquisition Inquiry” and… you don’t archive it.
You click.
You read.
You even imagine what it would feel like to not have 48 Slack channels whispering your name.
That’s a massive tell.
If your nervous system relaxes at the idea of letting go, start talking to buyers. Quietly. Now.
I used to think I was bad at follow-through.
Turns out, I just like starting businesses.
Scaling past a certain point?
Feels like filing expense reports with better margins.
If you’re more excited about your new agency / book / pressure-washing side hustle than closing Q3 strong, don’t guilt yourself.
That’s not a character flaw.
That’s just an honest-to-God founder lifecycle.
This one is sneaky.
When people ask what you do, you pause before answering.
Or you mumble “I used to run…” even though you still technically own it.
Or worse, you say nothing; because you’re in limbo.
This is where identity death begins.
And if you’re still hung up on that, read The Courage to Be Disliked then tell your business (and your ego): “Thanks for everything. I’m off to build a weird newsletter now.”
Most founders overvalue their own involvement.
I used to think I was Metalab. Then I went backpacking and my friend Mark ran it better than I did.
If you’ve built systems, hired great people, and replaced yourself with SOPs… you’ve built something transferable.
A buyer doesn’t want you. They want proof that they don’t need you.
Some people want to ring the bell at the NYSE.
Others want to slip out the side door and disappear to Tofino.
If the idea of a big announcement makes you nauseous, and you’d rather sell via text message over Signal?
You’re my people.
Quiet acquisition is a founder’s Irish goodbye.
Q: What’s a “quiet acquisition,” anyway?
It’s a private sale. No banker decks. No bidding war. Just a direct, quiet deal; often with a strategic or holding company.
Q: Is now a bad time to sell?
Only if your books are a mess. Otherwise, solid businesses are always attractive to the right buyers.
Q: How long do these deals take?
30–90 days is typical if your financials are clean and you’re not precious.
Q: Will I get a better price if I go public with it?
Maybe. But you’ll also get 6 months of tire-kickers and spreadsheet warriors. Choose your pain.
Q: What kind of businesses are buyers like you looking for?
Boring ones. High margin, recurring revenue, light ops, and ideally growing without heroic effort. See Why the Most Profitable Businesses Are the Ones Nobody Talks About.
Q: Should I stay on after the sale?
Only if you want to. Most quiet buyers prefer a clean handoff.
Q: Should I talk to my team first?
Not until it’s real. Uncertainty kills morale.
Q: How do I find a buyer quietly?
Email people like me. Or better yet, read How to Sell Your Business to Tiny Capital.
Q: Is it weird to want to walk away from something successful?
No. It’s actually a sign that you did it right.
If you’re thinking about selling your business…
You already know it’s time.
You’re just afraid to say it out loud.
But here’s the thing most people won’t tell you:
Letting go at the right time?
Is a superpower.
And if you do it quietly, on your terms, without turning it into a public performance?
Even better.
So if this post made you feel seen, you might also enjoy Bootstrapped, Not Broken; it’s about building something great, selling it with grace, and not needing a $100M exit to be proud of your work.
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