6 CPA Hot Takes From a Seller's Coaching Call You Need Now!
(and 4 action steps)
Last week, I hopped on a coaching call from atop a mesa in the panhandle of Texas.
Side Note: I totally fell in love with Palo Duro Canyon State Park. Jaw dropping views and great internet! This was probably my favorite camping spot on the Epic Road Trip Spring 2025. I solo camped for 5,027 miles across the southern half of the US. More stories on that later.
This business owner scheduled a coaching call after going through my seller’s guide, 9 Steps to Selling Your Business. She is pretty deep into the process of selling her online store, and frankly, she’s doing a great job:-) What followed was a perfect strategy session where we reinforced what she was already doing and established specific steps to move forward in the selling process.
Before we dove into tax structure, due diligence and data rooms, buyers, and when to bring in an attorney, I had to applaud this client—she's what I would call a “textbook seller.” Or at least what we’d like to see from sellers.
She’s exiting at peak performance (best year, best quarter).
She’s collected growth plans, financials, vendor stats, and job descriptions.
She’s emotionally ready and focused on a smooth transition.
💥 CPA Hot Take: Start when the numbers are strong. Don’t wait until you're sick of the business, or just plain sick.
Stock Sale vs. Asset Sale
One of her main concerns was figuring out the difference between a stock sale and an asset sale. This is where many sellers, and buyers for that matter, are totally clueless—but this is huge! Kudos to this seller for even being aware of these deal components and seeking more knowledge. I’ve already written a few articles on the difference between stock sales and asset sales: you can find them here and here. But it was fun to review it with someone in the process of getting a deal together.
Stock Sale You sell your entity (LLC, S-corp, C-corp), the EIN, contracts, even the business bank account.
Best tax treatment for you, the seller
Buyers take on all liabilities and skeletons and get little to no depreciation
Asset Sale You sell the “stuff” of the business—inventory, equipment, IP, goodwill.
Buyer gets tax write-offs (depreciation & amortization)
Seller pays more in taxes
The Second Layer in an Asset Transaction
The next part or layer in determining your basic deal structure is the allocation that needs to happen with an asset sale. Your agreed upon sales price has to be allocated amongst all the different assets that are being sold. And each asset class is taxed to the seller, and depreciated for the buyer, in a different way.
💥 CPA Hot Take: What’s good for the seller is bad for the buyer—and vice versa. What really matters is NOT what you sell your business for—it’s how much of that you get to put in your pocket.
Due Diligence & Data Room
This seller extraordinaire had already created vendor sales breakdowns, collected job descriptions and hours for her staff, and was beginning to organize her P&Ls, tax returns and payroll info. I reminded her to mask or mark-out SSNs and other private info. We talked about using Google Drive or Dropbox to store and share these items.
(Respond back with DATAROOM if you’d like my data room outline resource.)
Due diligence can be very uncomfortable: like getting naked at the beach. The buyer wants to see it all, and rightly so. But it doesn't feel good. Suck it up, show them what they need, and feel free to offer any story about what was really going on when your sales took a dip or that key employee ran off with some of your best clients. They're going to figure it out anyway and it will be better if you disclose it up front.
💥 CPA Hot Take: If your data room looks like a digital junk drawer, you’re sending the message that your business is just as messy. Clean, well-organized records don’t just impress buyers—they speed up deals and protect your price.
Assess Your Buyer
This buyer seemed reasonable: planning to operate as-is for a year, then working to scale in a controlled, planned out manner. That’s a green flag. Unless you’re selling for 100% cash and immediately walking away, your buyer is going to become your business partner in some fashion or another. Believe me, unless you crawl into a hole, you will still hear about your business and how it’s going with the new owner, and in my case, tons of complaints from now-unhappy clients:-( I totally messed that up.
We also discussed:
Transition help (consulting for 90 days)
The possibility of seller financing
Prepping emotionally for deal turbulence
Ways she could continue to receive income from the business
💥 CPA Hot Take: Deals often break down—sometimes more than once—before they come together.
When & How with Attorneys
How and when to involve an attorney is a common concern for both buyers and sellers. Unless I was doing a zero-money, 100% seller financing deal, I would absolutely use an attorney. (People are so sue-happy anymore.) But you also have to know what you’re getting into and how to maintain control of the relationship.
Be clear on your expectations upfront. Do you want negotiation help, or just document drafting? Do you already have a draft that only needs reviewed and tweaked? If you call a random lawyer and ask for a quote on handling your upcoming deal, they will assume they are doing “everything”.
Push for a flat fee, not hourly.
If you’re a little low on confidence at the deal table, hire earlier, but my suggestion would be to wait until after the Letter of Intent is signed and due diligence is well under way, with no red flags in sight.
💥 CPA Hot Take: Attorneys bill by the hour, and every “quick chat” counts. Know exactly what you want them to do—or prepare to watch your deal budget disappear in 5-minute increments.
Action Steps for Sellers Like You
Compile a clean, detailed data room.
Educate yourself on tax treatment and consult your CPA.
Get a shortlist of attorneys—know what you want them to do.
Anticipate due diligence questions and prepare to get naked!
💥 CPA Hot Take: Don’t underestimate the emotional part—selling your business will be a roller coaster of highs and lows.
Final Thoughts
This seller is in great shape—and you will be too, IF you start now. Preparing a business for sale is a lengthy process. You should be planning a year or two before your anticipated sale date. Even better, you should be planning for your exit on day 1! Selling a business takes time, and an experienced friend in your corner. That’s exactly what I do.
Want to talk about YOUR exit? Send me a message or book a 1:1 call here
Peace out!
