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The Seller’s Playbook

Rule 33 of 34 · Part 5, Structure and the Money

Measure success by after-tax proceeds.

Chapter 33: Tax Planning: Protecting the Wealth You Just Created

Now that I’ve sold, how do I keep the proceeds?

What sellers often miss

Many owners believe the transaction is the finish line. In reality, it is often the starting line for an entirely new chapter of financial decision-making. The skills that made you a successful entrepreneur are not necessarily the same skills required to manage significant liquidity. Without a well-defined plan, even successful exits can produce disappointing long-term outcomes.

The takeaway

Do not evaluate your transaction based on enterprise value, purchase price, or even net proceeds at closing. Evaluate it based on the long-term financial security, flexibility, and opportunities it creates for you and your family. Wealth creation is important. Wealth preservation is essential.

Figure from the book · Chapter 33
Figure from Tax Planning: Protecting the Wealth You Just Created. Illustrative rates. The same slice of your price is worth noticeably less taxed as ordinary income.
Illustrative rates. The same slice of your price is worth noticeably less taxed as ordinary income.

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

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