The Entrepreneur’s Guide to Buying a Business: What I Learned from My Own Acquisition

When I recently bought a business, it wasn’t my first rodeo in M&A. But, before this, my acquisition experience was as a CFO inside a business. I had the spreadsheets. The diligence. The bankers. And, the attorneys at my disposal. But when YOU'RE the one buying the business, the game changes.

If you’re an entrepreneur considering an acquisition, here’s what I learned—from what to do, what NOT to do, and what no one tells you about the real weight of signing a personal guarantee.

1. Assemble the Right Team (And Don’t Skimp Here)

Buying a business is not a solo endeavor. The right professionals will save you from expensive mistakes, bad deals, and sleepless nights. Here’s who you need in your corner:

A Banker Who Understands Business Acquisitions – Not just any lender, but one who has structured financing for business acquisitions before. If you’re taking out an SBA loan, you need someone who can walk you through the complexities of deal structuring, covenant compliance, and risk mitigation. A good banker isn’t just approving the loan; they’re ensuring your financial stability post-acquisition.
A Business Attorney Who Specializes in M&A – Your cousin’s real estate lawyer? Not the right fit. You need someone who can tear through contracts, negotiate strong reps and warranties, and ensure you’re not walking into a legal mess. They should also be well-versed in non-compete agreements, earnouts, and liability protections.
A Broker Who Works for YOU (Not Just the Seller) – A good broker can facilitate deals, but they primarily work for the seller. If you’re buying, make sure you have someone advocating for you, helping identify risks, and structuring the deal in your favor. An independent buy-side advisor can be invaluable.
A Fractional CFO or Due Diligence Expert – (Yes, I’m biased, but hear me out.) You need someone who can see through the financials and tell you what’s real and what’s not. Someone who can model out different acquisition scenarios, identify hidden risks, and help structure the financial transition so that you don’t find yourself in a cash crunch three months in.

Pro Tip: Your best friends during an acquisition are your banker, your lawyer, and your CFO. Choose them wisely—this isn’t a reality TV show; you actually can vote people off the island.

2. The Numbers Tell a Story—Don’t Just Read Them, Understand Them

When I acquired my business, I had to go beyond the financial statements and ask: What’s driving these numbers?

Are revenues sustainable or is there customer concentration risk? If 40% of revenue is tied to one client and they leave, will the business survive?
Are expenses properly allocated or will I find financial landmines later? Some sellers overcapitalize assets or delay expenses to make profitability look better than it really is.
Is the business actually profitable, or just cash-flow positive on paper? Just because the P&L looks good doesn’t mean the business is on solid ground.

Pro Tip: Trust, but verify. And by verify, I mean dig into the financials like your ex is hiding something—because sometimes, they are.

3. Look at the Seller—Not Just the Business

The business may check all the boxes, but the seller matters just as much.

Are they transparent? If they dodge questions or get defensive, that’s a red flag.
Why are they selling? Retirement? Health? Burnout? Or are they trying to unload a sinking ship before it hits rock bottom?
Will they transition well? Some sellers will hand over the keys and disappear. Others will stay too involved and struggle to let go. (A good LCSW is helpful here.)
What’s their real motivation? A seller who built a business over 30 years is different from one who’s flipping companies for profit. Their emotional attachment (or lack thereof) will impact how smooth—or painful—the transition is.

Pro Tip: If the seller talks more about their boat than their business, dig deeper. That boat might be floating on a sea of hidden liabilities.

4. Signing a Personal Guarantee: The Moment It Gets Real

I’ve spent my career advising businesses on financing, risk, and capital strategy. But when I sat down to sign a personal guarantee, I felt the full weight of the risk.

A personal guarantee means you’re on the hook—personally.

If the business doesn’t perform? If something unexpected happens? The bank isn’t going after just the business. They’re coming for you.

For me, that meant mortgaging my home.

It was one of those moments where the magnitude of the decision hit me like a freight train. But here’s the thing: Calculated risk is part of being an entrepreneur.

You just need to make sure it’s a risk worth taking.

Pro Tip: Before you sign a personal guarantee, take a deep breath. And maybe have a stiff drink. You’re playing in the big leagues.

5. The First 90 Days After the Acquisition Can Make or Break You

Buying a business is just the beginning. The transition period is where most deals succeed—or fall apart.

Take control of cash flow immediately. Even if the business was profitable before, new ownership means changes. Protect liquidity. Know exactly when every dollar is coming in and going out.
Communicate with employees early and often. Uncertainty breeds anxiety. If employees don’t know what’s happening, they’ll assume the worst. The first few weeks post-close set the tone for morale.
Focus on customer retention. Clients will be wary of an ownership change. Be visible, be proactive, and don’t assume they’ll automatically stick around. Introduce yourself. Reinforce your commitment to service. Continuity is everything.

Pro Tip: Always wear your snazziest blazers. And, supply chocolate. Because chocolate helps everything.

Final Thoughts: Would I Do It Again?

Absolutely. Buying a business was the right move to expand my existing firm's services, allowing us to fulfill our mission. But I walked into it with eyes wide open.

For any entrepreneur considering an acquisition:

Have the right team.
Scrutinize the numbers.
Vet the seller.
Respect the weight of a personal guarantee.
Be ready to lead on Day 1.

Acquiring a business is a high-stakes game—but when done right, it’s an incredible way to scale. Expand. And, take your business to the next level.

Thinking About Buying a Business?

If you’re considering an acquisition and need an experienced financial strategist in your corner, The William Stanley CFO Group specializes in helping business owners navigate the financial complexities of M&A. Reach out today to see how we can help set you up for success.