Lately, everyone seems to be talking about buying businesses.
Quit your tech job. Walk away from your W2. Buy something “boring.” Social media makes it sound like owning a business is the next passive income hack.
I get it. I’ve seen those posts too. But let me tell you—most of what’s being said out there is misleading, and in some cases, downright dangerous.
That’s exactly why I recorded a recent episode of the Exceptional Companies Podcast with my recurring guest and good friend Greg Wiggins. We broke down the top myths and landmines that trap unsuspecting buyers and shared what we’ve learned from owning and operating multiple companies ourselves.
If you’re serious about buying a business—or even just curious—read this first.
Myth #1: Owning a Business Is Passive
It’s not. Not even close.
I’ve owned nine businesses. I’ve also invested in real estate across nearly every asset class. And here’s the truth: neither is passive, at least not the way people talk about it.
Even if you build strong systems and use something like EOS or our own Exceptional Systems framework, you still need to be involved. Five to ten hours a week? That might work. But disappear entirely? That’s called negligence.
If you’re looking for something passive, put your capital in the market. But don’t buy a business and assume it’ll run itself.
Greg put it best: “There’s going to be nights when you’re up at midnight because someone quit or an insurance requirement wasn’t met. And you’re responsible—not just for yourself, but for your employees, their families, and their livelihoods.”
That’s not passive. That’s leadership.
Myth #2: Culture Will Sort Itself Out
This might be the biggest mistake I see buyers make—they underestimate the importance of culture.
Especially if you’re coming from a white-collar background and buying a blue-collar business, you’re in for a wake-up call.
These teams don’t care how many portfolio companies you’ve managed. They want to know: Are you in the trenches with us? Do you get it?
Greg explained this perfectly: “You’re not the white knight riding in. You’re the outsider. You have to earn trust, earn respect, and prove you understand the work.”
Early in my career, I came in way too fast—new systems, new processes, new technology. And we lost some amazing people because of it. That’s one of my biggest regrets.
Now? We do it brick by brick.
Sometimes that means spending the first two quarters just having conversations and building relationships. We don’t even mention EOS or Exceptional Systems by name. We just started introducing better practices slowly and respectfully.
Because when you rush change, you lose the people that matter most.
Myth #3: You Can Buy Any Business, Anywhere
Here’s another myth I hear a lot: “If the business is good, it doesn’t matter where it is.”
That’s dangerous thinking, especially for first-time buyers.
If you buy a business in another state, without a support system, network, or local team, you’re flying blind. That’s hard enough on its own. Add a spouse and kids at home—and no real plan for how you’re going to split your time—and it’s a recipe for burnout.
Now, if you’ve already done a few deals and built solid systems, that’s a different story. But if you’re just getting started, look for something local or somewhere your family is willing to move with you.
Myth #4: Blue-Collar and White-Collar Businesses Are Basically the Same
They’re not.
And if you think you can treat them the same, you’re setting yourself up for failure.
Greg said it better than I could: “A welder is different than a project manager. A coder is different than a technician. You have to understand people at a base level.”
Some of our clients are still using paper invoices, and it works for them. If you come in expecting to drop in a CRM, automate everything, and “optimize” their workflow overnight, you’re going to hit resistance.
Now, in some white-collar companies, I can hand someone the Traction book and they’ll come back the next week asking how to implement it. But in blue-collar environments, the culture shift is much bigger.
That’s why we’ve learned to start small. Build trust. And understand that the team often mirrors the previous owner. If that owner was in their 60s and not using much tech, odds are the team isn’t either.
The Brick-by-Brick Mindset
One of the most powerful lessons we’ve learned—and one of the most expensive—is the importance of pacing.
When we first started, we came in hard. Tried to implement systems, set KPIs, run meetings, and optimize from day one. And it backfired. We lost great people because we didn’t take the time to build trust.
Now, our motto is brick by brick. We don’t introduce all our systems right away. We start doing things differently, but without overwhelming the team with new language or expectations.
It takes longer, but it works.
Landmines in the Deal Process
Even if you’re a great leader and have a heart for the team, the deal itself can still sink you.
Let’s talk about a few common traps:
🚩 Overconfidence from Your Corporate Experience
A lot of folks coming out of finance or private equity believe they’re ready to own a business. And they might be. But running a team with someone else’s capital is not the same as having your house on the line when you sign the debt note.
When your name’s on the loan, it hits different.
🚩 Loss Aversion Bias
This one’s huge. Buyers spend so much time and money on due diligence that they feel they have to close—even when the deal doesn’t make sense.
That’s when people get hurt.
🚩 Not Enough Cash
If you don’t have cash—enough cash for legal, for operations, for the unexpected, you’re not ready.
Even with our conservative planning, we’ve hit tight spots that surprised us. If we didn’t have cash to float the tough times, we’d have been in real trouble.
If you’re asking for 100% seller financing because you don’t have capital, you’re not just risking the deal—you’re risking bankruptcy.
You Need the “Engineer in the Room”
Greg told a story that stuck with me.
He was pitching an oil and gas deal and got grilled by an engineer who shut everything down. Greg thought the guy was a jerk—until the business owner told him, “That’s exactly why I hired him. If a deal can survive him, it’s worth doing.”
That’s the kind of advisor you need.
Someone who’s not emotionally invested. Someone who’s not trying to sell you anything. Someone who will poke every hole in your logic, so you don’t step on a landmine you didn’t see coming.
Our Framework: People, Process, Profitability
When we evaluate a deal—whether it’s for ourselves or for one of our clients—we use the 3P framework:
- People – Who’s running the business? Will the team stay? Can you lead them?
- Process – Are there systems in place, or is everything in someone’s head?
- Profitability – Will the deal cash flow after debt and expenses?
If it doesn’t pass those three tests, we walk.
Final Thoughts: Know What You’re Signing Up For
Let me close with this:
“If you enjoy being home every night and having weekends to yourself, you probably shouldn’t buy a business.” – Greg Wiggins
That hit hard. And it’s true.
Owning a business isn’t a side hustle. It’s not a shortcut to early retirement. It’s a full-on lifestyle shift—and it demands everything you’ve got.
If you don’t enjoy the suck… don’t do it.
There’s going to be chaos. People will quit. Clients will leave. Vendors will flake. And if you’re not wired to lean in and solve problems when they arise, you’re going to burn out.
But if you are wired for it—if you do love the challenge—this path can build wealth, freedom, and something truly exceptional.
Just make sure you go in with your eyes wide open—and the right people in your corner.
📘 Want to Go Deeper?
I’ve written two quick-read guides to help you think this through:
- Buying Main Street – For buyers who want to avoid landmines and find the right first deal
- Selling Main Street – For business owners preparing to exit with strategy and clarity
If you’d like a free digital copy of either one, just reach out. I’d be happy to send it over.
Until next time—keep building exceptional companies.
AND MORE TOPICS COVERED IN THE FULL INTERVIEW!!! You can check that out and subscribe to YouTube.
If you want to know more about Greg Wiggins, you may reach out to him at:
- LinkedIn: https://www.linkedin.com/in/gregwiggins/
- Website: https://www.redbirdcos.com/
- Website: https://myspindr.com/
- Website: https://www.namesgreg.com/
Connect with Chris Seegers:
- Website: https://exceptionalcos.com/
- Email: Ch***@************OS.com
Other Resources:
- Books: Selling Main Street by Chris Seegers
