When it comes to buying businesses, there’s the textbook version of how it’s supposed to go…

And then there’s reality.

One of the things I love about my co-founder at Acquisition Lab, Chelsea Wood, is that she never shies away from the truth. She doesn’t sugarcoat it. She doesn’t hype it. She just tells it like it is.

On a recent episode of Acquiring Minds, she shared a story about a buyer who nearly walked away from a perfectly good deal — not because the numbers got weird, but because the seller’s personality threw him off.

That’s the reality of this game: deals fall apart for reasons you’d never expect. And after helping Lab members acquire nearly half a billion dollars in small businesses, Chelsea has seen every roadblock under the sun.

In this piece, she’s going to walk you through the seven most common issues that stall buyers and how to handle them before they cost you the deal. These are the questions buyers whisper on calls, the doubts that creep in late at night, the stuff X threads and clickbait headlines don’t prepare you for.

Buying a business is nuts. 

When you tell someone outside this world that you’re about to sign a personal guarantee on millions of dollars of debt to buy a small business, they’ll look at you like you’ve lost it.

And maybe you have. But with that risk comes extraordinary reward — if you do it right.

The problem is, buyers get hung up on the wrong things. They read one too many social media posts about “buying with no money down” or “working four hours a week” and start chasing fantasies.

 

 

Then they hit the messy middle of an actual deal, and reality sets in.

In the Lab, I’ve had the same seven conversations over and over again with buyers throughout the years. These aren’t new questions, but they’re the ones that stall searches, kill deals, and cause sleepless nights. So let’s break them down.

 

1. “Will I be buying a business or a job?”

Everyone says, “I want to work on the business, not in the business,” but here’s the truth:

You can’t work on a business without being in it first. 

Even if the seller claims they only spend four hours a week running it, that’s because they already know the company inside out. You don’t.

Your first six months (minimum) will be about stabilizing, building trust with employees, and making sure the pipes are connected. Think Stripe accounts, vendor relationships, and payroll systems — tedious but critical work.

Yes, you can eventually hire an operator. But ask yourself: is hiring a strength of yours? Do you know what competencies your operator should have? Who’s going to train them — you, or the seller you just paid millions to exit?

This doesn’t mean you’re doomed to buy a job. It means you have to earn your way to owner-not-operator status and understand the foundation you need to build first. Dan Martell’s replacement ladder helps to depict the steps in which you should thoughtfully and patiently delegate your roles on the way to becoming a hands-off owner.

 

 

2. “I can’t afford to take a pay cut.”

Nobody likes this one. But it’s reality.

Most first-time owners pay themselves somewhere in the $100K–$150K range in the early years, so if you’re coming from a cushy $300K corporate job, that salary cut might sting.

But ownership isn’t about a paycheck. It’s about building wealth. Every dollar you leave in the business — instead of pulling out as salary — increases the company’s value and accelerates your exit multiple.

Ask yourself: what’s the minimum you need to support your family? 

Pay yourself that. Then stair-step your salary as the business grows. Make the short-term sacrifices for long-term payoff.

 

3. “How much of my own capital should I use?”

I hear this all the time: I don’t want to drain my savings. I’ll just use seller financing.

Let’s set the record straight. Seller financing isn’t bad — it’s been around forever. But the terms can be brutal. Short amortizations, balloon payments in year three, sellers who won’t go away because their payday depends on your performance.

SBA financing is often cheaper and safer. Ten-year terms give you breathing room. And yes, you’ll need skin in the game — usually around 10%, but that’s not a bug, it’s a feature. If you’re not willing to risk your own money, why should the bank, seller, or investors trust you?

 

Source: Wall Street Oasis

 

4. “Am I really ready to run a company?”

This one comes up constantly. Buyers look in the mirror and wonder if they’ve got what it takes.

The answer depends on your background. If you’ve never managed people, overseen a budget, or been accountable for P&L, don’t go buy a $5M company with 40 employees. Start smaller. Build the reps.

If you have led teams, managed cash flow, and hired and fired, you’re in a better position. But lenders and sellers want to see alignment. A former investment banker trying to buy a blue-collar manufacturing shop raises red flags. A VP of operations buying that same shop? Much more compelling.

It’s not about perfection. It’s about transferable skills.

 

5. “What if the seller just stays on and runs it?”

Tempting idea. Terrible plan.

Imagine buying a $2M Bugatti, handing the seller the keys, and saying, Keep driving it, I’ll just make the payments. Insane, right? That’s what it looks like when you pay the seller millions and let them stay in control.

 

 

Sellers check out once the wire hits. Their incentives shift. Power struggles erupt. And if you’re using SBA financing, you can’t keep them longer than 12 months anyway.

You’re the owner. You carry the risk. You need to be in the driver’s seat.

 

6. “Why aren’t my LOIs getting accepted?”

The market is competitive. Strategic buyers and private equity are pushing multiples up. That doesn’t mean you’re doing something wrong, but it might mean you’re making one of these mistakes:

• Over-correcting for risk (stacking seller notes, demanding endless transition periods, lowballing every offer).
• Coming across desperate or high-maintenance with brokers.
• Targeting businesses misaligned with your experience.
• Ignoring geography — brokers are wary of buyers who promise to move but don’t.

Every term in a deal lives on a spectrum. If you push all the risk onto the seller, you look unserious. Meet them in the middle.

 

7. “Maybe I’m just not ready.”

This is the quiet fear under all the others. Am I cut out for this?

Here’s my take: if you’re willing to learn, if you have transferable skills, and if you approach deals with eyes wide open, you’re more ready than you think.

 

Source: 2IP Independent Investment Partners

 

But buying a business is not a playground. Don’t use a personal-guarantee loan to “try on” leadership skills you’ve never tested. Buy a business that fits your strengths. Grow into the rest.

 

What’s the Right Decision for YOU?

At the Lab, our goal isn’t that every member closes a deal. It’s that every member makes an informed decision. Sometimes the right call is to buy. Sometimes the right call is to wait.

But whatever you do, don’t buy a fantasy. Buy a business – a real one. With all the tedium, responsibility, and cash-flow headaches that come with it. Because it’s those exact things that will create lasting wealth.

Ready to acquire a business in the next 12 months? The Acquisition Lab is your first stop. Reach out to us today and get on the fast track to becoming an acquisition entrepreneur.