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The Seller’s Playbook

Rule 23 of 34 · Part 4, The Deal Terms

Structure matters as much as price.

Chapter 23: Asset Sale vs Stock Sale

Should I sell the assets or the stock?

What sellers often miss

Many owners negotiate aggressively over valuation while spending relatively little time understanding the implications of transaction structure. Buyers know that structure affects risk and economics. Sellers should approach it with the same level of attention. A seemingly minor structural provision can have significant consequences long after the closing documents are signed.

The takeaway

Never evaluate an offer based solely on purchase price. Work closely with your legal, tax, and transaction advisors to understand how the deal is structured and what that structure means for your after-tax proceeds, future obligations, and overall financial outcome. The best deal is not always the one with the highest price. It is the one with the best combination of price, structure, and certainty.

Figure from the book · Chapter 23
Figure from Asset Sale vs Stock Sale. The buyer and the seller start this negotiation on opposite sides.
The buyer and the seller start this negotiation on opposite sides.

Illustrative, not your deal. Where the book uses dollar figures, they are there to show how something works, not to describe your business. Your banker, your accountant, and your attorney will put real numbers to your own situation. Full note.

Terms this chapter uses

Read the full chapter in the book