The Illusion of the Deal
There’s a moment every buyer looks forward to.
The deal closes. The papers are signed. The business is yours.
And for many, that moment feels like the finish line.
But as Chris put it plainly, the transaction is the easy part. The real work begins the moment you walk into the business on day one, knowing your name and your debt are now attached to it.
Will echoed this reality from experience. After facilitating over a hundred acquisitions, one pattern became impossible to ignore:
“I’ve never seen projections that weren’t up and to the right… and 87% of the time, the business goes down in the first year.”
That gap between expectation and reality is where most new owners struggle.
Why Most Businesses Decline in Year One
It’s not bad luck. It’s predictable.
Will broke it down into three consistent factors.
First, the seller is distracted. During the 90-day transaction period, they’re overwhelmed, stressed, and pulled away from running the business. Sales slow. Pipelines shrink. Momentum fades.
Second, buyers miss things. No matter how thorough the diligence, surprises show up. Equipment fails. Costs increase. Systems break.
Third, people react. Employees test the new owner. Some push for raises. Others question leadership. The dynamic shifts overnight.
Put together, it creates a perfect storm.
And if you’re not prepared, it can feel like everything is falling apart.
The Operator Matters More Than the Buyer
One of the most powerful ideas in this conversation is simple.
Buying a business and running a business are completely different skill sets.
Will described the challenge as “unicorn hunting.” You’re looking for someone who can source and structure a deal, secure financing, and actually run the business.
Most people only have one or two of those skills.
That’s why their model focuses on pairing experienced operators with structured acquisitions, allowing each person to do what they do best.
Because at the end of the day, the operator determines the outcome.
Not the spreadsheet.
What Makes a Great Operator
So what actually separates someone who succeeds from someone who struggles?
It’s not intelligence. It’s not credentials.
It’s how they respond when things go wrong.
Will shared one of the most revealing questions they ask every potential operator:
“What is the hardest thing you’ve ever gone through?”
Because business ownership will test you. It’s not a question of if, but when.
The real signal is whether someone has experienced adversity, reflected on it, and grown from it.
As Will explained:
“If you haven’t gone through suck, we’re about to go through suck together.”
That combination of grit and self-awareness becomes the foundation for long-term success.
The First 90 Days: Control the Chaos
If the first year is difficult, the first 90 days are critical.
This is where most new owners make their biggest mistakes.
They try to change everything.
They react emotionally to early dips.
They pull too many levers too quickly.
Will’s advice is the opposite.
Start simple.
Focus on two things.
First, fix what’s broken. Identify missed items from diligence and address them quickly. Treat it like a game of whack-a-mole.
Second, protect and drive revenue. Don’t reinvent the business. Take what’s already working and push it forward immediately.
Because revenue will dip. That’s expected.
What matters is how quickly you stabilize and rebuild momentum.
Control vs. Trust: The Balance That Changes Everything
One of the most interesting insights was how Will’s team evolved their approach to new operators.
At first, they gave full control immediately.
It didn’t work.
Some operators did nothing. Others changed everything.
Now, they take a structured approach.
Control is earned over time.
Operators start with clear boundaries. As they prove consistency and hit key metrics, they gain more authority.
It’s not about limiting leadership.
It’s about protecting the business while the operator learns.
Because early mistakes don’t just cost time. They can cost the entire opportunity.
Why Main Street Is Having a Moment
Beyond the mechanics of buying and running a business, there’s a bigger shift happening.
Main Street is becoming attractive again.
For years, small businesses were seen as unscalable and inefficient. Now, the narrative is changing.
As Will put it:
“Main Street is cool again.”
People are leaving corporate roles, looking for ownership, autonomy, and real impact.
And the numbers back it up.
Small businesses have driven the majority of job creation over the past 25 years. That trend is only accelerating.
This isn’t just a business opportunity.
It’s a shift in how people think about work, ownership, and the future.
Closing Reflection
Buying a business isn’t the hard part.
Becoming the kind of person who can lead it, grow it, and carry it through uncertainty, that’s the real challenge.
This conversation is a reminder that success doesn’t come from perfect projections or clean spreadsheets.
It comes from grit, reflection, and the willingness to stay in the game when things get hard.
Because in the end, the businesses that succeed aren’t the ones that start perfectly.
They’re the ones led by people who don’t quit.
Thank you for joining us for this episode of The Exceptional Business Podcast. Stay tuned for more conversations that inspire connection and growth.
AND MORE TOPICS COVERED IN THE FULL INTERVIEW!!! You can check that out and subscribe to YouTube.
If you want to know more about Will Fry, you may reach out to him at:
- Website: https://www.americanoperator.com/
- Twitter/X: https://x.com/BuySellSMB
- LinkedIn: https://www.linkedin.com/in/fryw
Connect with Chris Seegers:
- Website: https://exceptionalcos.com/
- Email: Ch***@************OS.com
Other Resources:
- Books: Selling Main Street by Chris Seegers
