Welcome back to the Mid Market Insider!
Today, I’m breaking down why most businesses that go to market never actually sell—and how hidden red flags can quietly push buyers away long before owners understand what went wrong.
Thinking About Selling Your Business?
I’ve spent nearly 20 years buying, growing, and evaluating companies.
If you’re considering a sale or just want to understand more about my role and what we do, feel free to grab 30min on my calendar below:
As you probably already know, studies show that roughly 80% of businesses that go to market never sell at all.
A depressing fact. But why does this happen?
Some people assume that it’s because most that go unsold are “bad” businesses. That they’re unprofitable, or are struggling to hire and retain staff, or have a terrible reputation with customers, and so on.
But after watching hundreds of transactions up close (from both sides of the table), I can tell you those are rarely the reasons that a deal dies.
Instead, what kills a deal is usually something quiet – something that potential buyers can spot in an instant, but the business owner has no idea is a glaring red flag.
And by the time the owner realizes something is wrong…
Their buyer has already walked away.
That’s why in this short YouTube video, I decided to break down the 10 silent deal-killers buyers never warn you about – the ones that make them disengage even when they like your business.
Here’s a little taste of what you’ll learn:
The 5 word phrase which instantly exposes you to buyers as a potentially-flaky “rookie”...
How having big lucrative contracts with a few of your best customers can actually lower your valuation…
Why the diligence process can often kill a deal… even if everything turns out to be squeaky clean.
To be clear – none of these red-flags makes your business “bad.”
But to a buyer, they all signal risk. And risk destroys valuation, structure, or the deal entirely.
That’s why the businesses that actually sell don’t hope to get lucky…
They get prepared.
They see their business through a buyer’s eyes. They remove risk before it wrecks a deal. And they control the narrative, instead of reacting to it.
That’s all for today’s newsletter! Thanks for reading!
📅 Next Week:
In next week’s edition, I’ll break down why so many promising exits fall apart during diligence—even when the business itself is strong.
And how the best sellers build leverage years before going to market, instead of trying to fix everything at the last minute.
Keep building,
Nick
In Case You Missed It: Must-Watch Video
Why 80% of Businesses Don’t Sell...and How to Be in the Successful 20%
Click the link below and check it out:
