Selling a business isn’t like selling a used car. You don’t just hand over the keys and walk away. It’s a process that can make or break the legacy you’ve built — and whether you walk away proud (and paid) or frustrated (and broke) depends on how prepared you are.

Recently, I sat down with DeAnn Chase, founder of Chase Law Group and an incredible business attorney, to dig into the nitty-gritty of what really happens when you try to sell your business. Between the two of us, we’ve seen the good, the bad, and the “oh-no-this-deal-just-died-on-the-table.”

​Here’s what you need to know — with real stories and examples we’ve seen firsthand.
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​1. Financial Records Can Make or Break the Deal

Let’s start with the obvious: your numbers matter. But not just the “I’ve got money in the bank” kind of numbers. We’re talking clean, reconciled financials that actually tie to your tax returns.

💡 Real Example:
I’ve had business owners come to me in full panic mode because their books didn’t match their tax returns. One had a $30,000 “negative” showing on a credit card account — turns out they’d been recording payments but never entered the expenses. Imagine handing that to a buyer and expecting them to pay top dollar.

DeAnn shared a similar story: she’s literally seen deals fall apart because poor records killed buyer confidence.

Lesson: Don’t wait until you’re ready to sell to clean things up. By then, it’s too late to look trustworthy.


2. Your Legal Structure Tells a Story

Buyers don’t just buy your profits — they’re buying your systems, your compliance, and your ability to hand over something solid.

DeAnn walked through countless situations where missing agreements, sloppy stock certificates, or no operating agreement at all caused chaos in a sale.

💡 Real Example:
She once had a client whose stock certificates didn’t match the ownership records. Another had an LLC with no operating agreement, so no one could prove who owned what percentage. Both situations stalled deals and dropped the business’s value.

Lesson: If you don’t have your entity records (corporate minutes, operating agreement, shareholder agreements) cleaned up, you’re giving buyers a reason to pay less.


3. Protect Yourself Before You “Open the Books”

DeAnn emphasized that one of the smartest moves you can make is requiring a non-disclosure agreement (NDA) with non-circumvention language before showing your financials. This protects you from “buyers” who are really just competitors fishing for information.

From there, don’t skip the letter of intent (LOI) stage. It’s not binding, but it gets the big terms agreed to before lawyers rack up fees and before you expose everything.

💡 Real Example:
DeAnn told the story of a physical therapist who signed an “asset purchase agreement” that a broker gave her — thinking it was just part of negotiations. It wasn’t. She was basically selling her entire practice on terms she didn’t agree with, and it took major cleanup to fix.

Lesson: Don’t skip the process. Protect yourself with an NDA, then negotiate an LOI before you hand over sensitive data.


4. You’re Not “Off the Hook” After You Sell

A huge misconception business owners have is thinking once the sale is done, they’re in the clear. Not true.

💡 Real Example:
I reminded our audience: if the IRS audits tax years when you owned the business, you’re still liable. Even years after you sell, non-compliance can come back to haunt you.

DeAnn added that in a stock sale, the buyer inherits all the liabilities of the corporation — so if your compliance was sloppy, that could blow up the deal or reduce your price.

Lesson: Whether it’s taxes or corporate compliance, your past ownership can still follow you. Selling isn’t an escape hatch.


5. Beware of DIY or AI Contracts

We couldn’t leave without talking about contracts. Yes, AI tools like ChatGPT (👋 hi!) or LegalZoom can draft something. Yes, if two parties sign it, it’s binding. But that doesn’t mean it protects you.

DeAnn explained that courts interpret ambiguities against the party who provided the contract. If you hand someone a contract you don’t fully understand, you may be hurting yourself.

💡 Real Example:
I shared a painful family story — my grandpa signed a contract without reading it and sold our family’s 100-acre ranch for $1. It was binding, and nothing could be done after the fact.

Lesson: Cheap contracts are expensive mistakes.


The One Big Tip

I asked DeAnn to leave us with her #1 piece of advice. Her answer?

👉 Don’t shortcut the process. Get an attorney involved early.

Because here’s the truth: every single business owner I’ve talked to who skipped hiring a lawyer has regretted it. Every. Single. One.


Takeaway for Business Owners

Your business is one of the biggest assets you’ll ever build. When it’s time to sell, make sure you get the value (and peace of mind) you deserve.