Welcome back to the Mid Market Insider!
Today, I’m breaking down how buyers form opinions within minutes of meeting you, and the subtle mistakes business owners make early that quietly kill deals before they ever get started.
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 a wise man once said:
“You never get a second chance to make a first impression.”
That phrase gets overused, but when it comes to talking with potential buyers, it’s absolutely true.
After buying businesses through Four Pillars for over a decade, I can tell you this with confidence:
Buyers form an opinion about you and your business in the first 30 minutes of meeting you (often in the first 5 or 10).
That opinion shapes everything that follows:
How hard they negotiate
How skeptical they are during diligence
Whether they ultimately push forward… or quietly walk away
What makes this tricky is that most owners don’t realize when they’re hurting themselves.
You might think you’re being careful. Or playing it cool. Or keeping leverage.
Meanwhile, the buyer is picking up signals that increase perceived risk.
And buyers hate risk.
The Mistakes That Quietly Kill Deals
Over the years, I’ve seen a handful of patterns repeat themselves when owners are first approached by a buyer.
None of these mistakes feel big in the moment.
They feel like smart positioning. Playing it safe. Saying the “right” things.
But together, they quietly erode trust.
Things like:
Sharing polished half-truths instead of being straightforward
Pretending you’re “not really interested” to look strong
Downplaying how involved you actually are in the business
Individually, they seem harmless.
Collectively, they signal uncertainty, and that’s when buyers start protecting themselves through tougher terms, more diligence, or walking away altogether.
A Resource to Help You Get This Right
I recently recorded a YouTube video where I break down the 4 biggest mistakes business owners make when first approached by a buyer, and how the top 10% of sellers handle these moments very differently.
If there’s even a chance you’ll sell one day, this stuff matters more than most owners realize.
And if you’d prefer to talk through your specific situation one-on-one, you can also schedule a no-cost strategy call.
On that call, we’ll:
Look at where your business stands today
Identify red flags that could hurt you in early buyer conversations
Map out what preparation would actually move the needle for you
No pressure or obligation.
The biggest mistake owners make is assuming they’ll “figure it out” when the time comes.
By then, the first impression has already been made.
That’s all for today’s newsletter! Thanks for reading!
📅 Next Week:
In next week’s edition, I’ll share a real example of how inbound buyer interest can quickly turn into a distraction, and why responding to every request isn’t always in your best interest.
We’ll talk about how to spot bad offers early, protect your time, and why preparation is what gives owners real leverage when buyers come calling.
Keep building,
Nick
