Two Owners Sold for $7 Million. One Kept $1.2 Million More.

Most business owners plan their retirement around their sale price. That's the wrong number. Two owners sold the same business, on the same day, for the same $7 million. One kept $4.4 million. The other kept $5.6 million. The $1.2 million difference had nothing to do with negotiation — it came from four deal structure decisions made eighteen months before either of them received an offer. In this video Matt Uhl breaks down exactly how the IRS taxes a business sale, the four structural decisions that most affect what you actually keep, and a four-step framework I call the After-Tax Blueprint that every seller should run before pricing their business or accepting an offer. If you're planning to sell a business in the next one to five years and nobody has translated your expected sale price into an after-tax number, this one is for you. ⏱️ CHAPTERS 0:00 The number your retirement is actually built on 0:18 Two sellers, same $7 million deal 1:41 The $1.2 million gap 3:18 Important disclaimer: I'm not a tax advisor 3:40 How the IRS actually taxes a business sale 5:09 Why calling your accountant after closing is too late 6:04 Decision 1: Asset sale vs. stock sale 7:06 Decision 2: Purchase price allocation 8:16 A $6.8M deal and a $2.1M tax bill 10:12 Decision 3: Earnout structure and timing 11:11 Decision 4: Deal timing and tax year management 12:20 Free After-Tax Calculator Guide 13:20 The After-Tax Blueprint framework 13:29 Step 1: Calculate your basis 14:00 Step 2: Model three deal structures 14:40 Step 3: Engage your tax advisor before the LOI 15:22 Step 4: The installment sale strategy 17:02 What actually separated Seller A from Seller B ABOUT I'm Matt Uhl, founder of Ridge Trail Capital. 18+ years in M&A and more than $200 million in transactions. This channel is for business owners preparing to exit — what your company is worth, what's keeping it from being worth more, and what you actually keep when you sell. New videos coming every week. #SellingYourBusiness #BusinessExit #MergersAndAcquisitions #ExitPlanning #SmallBusinessOwner #CapitalGainsTax #BusinessValuation #InstallmentSale