Hello friend,
Why you're getting this: this is my Friends Newsletter; where I share everything I wish someone had told me before I sold my first business.
I was 27, the wire hit, and I stared at the ceiling of my apartment wondering what the hell I had just done.
That was the moment I learned: selling your business doesn’t always feel like winning.
Since then, I’ve bought 50+ companies and talked hundreds of founders through their exit; some amazing, some soul-crushing.
This post is for the founders thinking of selling; but terrified of screwing it up.
Or worse; regretting it.
Let’s make sure you don’t.
You won’t feel it right away.
It shows up on Day 87, when nobody’s pinging you in Slack, and you suddenly miss arguing about logo placement.
Most founders don’t regret the money.
They regret losing:
That’s what you need to protect.
Founders tend to wait until:
Bad idea.
The best deals happen when:
Want a checklist?
Read this before listing:
Internal Link: The Boring Business Exit Checklist: How to Sell Without the Shark Tank Drama
Ignore the bro advice. You don’t need a flashy banker and a 50-page deck.
Some of the smoothest deals I’ve seen came from:
No auction. No drama. Just aligned incentives and a deal over coffee.
Thinking about selling quietly?
Internal Link: 7 Signs Your Business Is Ready for a Quiet Acquisition
Here’s a dirty little secret:
The buyer matters more than the multiple.
Don’t optimize for ego. Optimize for fit.
Ask yourself:
Best buyers are builders. Worst are spreadsheet kings.
For a play-by-play of how we do it, read this:
Internal Link: What It’s Really Like to Sell to Tiny: A Founder’s Exit, Step by Step
Never forget this:
An earn-out = golden handcuffs.
And those cuffs don’t come with the keys.
If you have to do one:
Better yet?
Just don’t.
Most people treat the exit like a finish line.
Wrong.
It’s a liquidity event; not a retirement plan.
Smart founders:
The second bite often dwarfs the first.
We talk about this all the time:
Internal Link: $1M to $10M Revenue? Here’s What Buyers Like Tiny Look For
True story: one founder sold for $12M, bought a Porsche, moved to Hawaii, and called me six months later sounding like he just got dumped.
Selling without purpose is like quitting the gym and throwing away your shoes.
You need:
Otherwise? You’re just rich and restless.
I’ve watched too many deals die because someone’s lawyer got high on their own term sheet.
Use a lawyer who:
You want smooth, not scorched earth.
Here’s the rule I live by:
The moment you feel doubt, it’s already over.
That’s true in hiring, dating, and exits.
Red flags:
When that happens?
Walk.
For the full philosophy:
Internal Link: Fire Fast, Fail Fast: The One-Strike Rule for Tough Decisions
There’s something magical when two founders do a deal.
It’s faster.
It’s cleaner.
It’s built on mutual respect.
At Tiny, we’re not bankers. We’re not suits.
We’re just founders who happen to buy businesses.
That’s why our deals look more like handshakes than hostage negotiations.
How long should a sale take?
2–4 months. Any longer and it’s probably bloated.
Do I need a broker or banker?
Not unless you’re running a $50M+ revenue machine.
Should I tell my team?
Tell leadership post-LOI, rest of team post-close.
What’s a fair multiple?
Usually 3–7x EBITDA depending on stickiness and margin.
Should I stay on after the sale?
If you want. But don’t be the ghost who won’t leave.
How do I know if it’s time to sell?
If you’re dreading Mondays and saying "just one more year," it’s time.
What happens if I change my mind mid-deal?
Pull out. Better awkward than lifelong regret.
How do I prep for diligence?
Clean books, clean cap table, clean contracts. Start now.
What’s the biggest regret sellers have?
Selling to the wrong buyer. Every. Single. Time.
What’s the biggest upside post-sale?
Clarity. Space. And yes—money (used right).
Selling your business without regret isn’t about price. It’s about peace.
If you want to exit well:
The best exits don’t end with confetti.
They end with a quiet knowing: I did this right.
Did you enjoy this?
Say thanks by checking out one of my businesses:
Follow me on Twitter/X: @awilkinson
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