Before You Sell: free resources for readers

Chapter 1

The Biggest Financial Decision You Haven’t Planned Yet

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. If you had to write down today the after-tax amount you would need from your business to be financially independent, could you do it with confidence?
2. Roughly what percentage of your total net worth is tied up in your company, and are you comfortable with that number?
3. Which of the three gaps (value, wealth, or purpose) do you think is largest for you right now?

Sources from the notes: Exit Planning Institute, Walking to Destiny; 26 U.S. Code 402, elective deferral limits.

Chapter 2

What Your Business Is Really Worth, and Why

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. Do you know your company’s adjusted EBITDA, and could you defend each adjustment to a skeptical buyer?
2. Which single value driver in this chapter represents the biggest risk in your business today?
3. Have you ever had an independent professional estimate your company’s value, and if so, is it still current?

Sources from the notes: IRS Publication 561 (valuing an interest in a business).

Chapter 3

Getting Sale-Ready: The Two-to-Five-Year Runway

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. If a qualified buyer called tomorrow, which three items on the readiness checklist would you be most worried about?
2. Which exit paths in this chapter fit your goals for your family, your team, and your legacy, and which ones would you rule out?
3. Do you have the core members of a deal team identified, even informally, and do they know about each other?

Sources from the notes: IRS, Employee Stock Ownership Plans (ESOPs).

Chapter 4

Timing: When to Sell, When to Wait, and When to Take Some Chips Off the Table

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. Where is each of your three clocks (personal, business, and market) right now, and are they pointing in the same direction?
2. If one of the “five Ds” happened in your business this year, would your current agreements, insurance, and plans protect your family and your company?
3. Would a partial liquidity option, rather than a full sale, better match your goals over the next five years?

Sources from the notes: Exit Planning Institute, How to Protect Your Business from the 5 D’s.

Chapter 5

Deal Structures in Plain English

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. For any offer you might receive, could you estimate the cash you would net at closing after debt, fees, escrow, and taxes?
2. How much of your financial plan would you be comfortable relying on earnout or rollover equity that you do not control?
3. Do you know whether your entity type and history make an asset sale or a stock sale more likely in your situation, and what that might mean for your taxes?

Sources from the notes: IRS Publication 544, Sales and Other Dispositions of Assets; 26 U.S. Code 338, stock sales treated as asset sales.

Chapter 6

Retirement Plans for Owners, Part One: Solo 401(k) and Safe Harbor 401(k)

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. Did you contribute the maximum allowed for your age to your company’s retirement plan last year? If not, what stopped you?
2. Has your company’s 401(k) ever failed nondiscrimination testing, or are you limiting your own deferrals to avoid that risk?
3. Is your current plan designed around your goals as an owner, or did it come bundled with your payroll service?

Sources from the notes: IRS Notice 2025-67, 2026 plan limits; IRS, One-participant 401(k) plans; IRS Publication 560, Retirement Plans for Small Business.

Chapter 7

Retirement Plans for Owners, Part Two: Profit Sharing and Cash Balance Plans

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. Is your company consistently profitable enough to support required annual contributions, and how stable do you expect those profits to be over the next five years?
2. Would a cross-tested profit sharing design allocate more of the company’s contribution to you and your partners than your current formula does?
3. If you sold the business in the next three years, do you know what would happen to each of your retirement plans and when?

Sources from the notes: 26 U.S. Code 404, deduction limits; PBGC, insurance coverage.

Chapter 8

Tax-Aware Planning Before the Sale

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. Have you had a dedicated pre-sale tax planning conversation with your CPA, separate from your annual tax preparation?
2. Do you know your company’s tax classification history, and how it might affect an asset sale versus a stock sale?
3. Are there charitable or family goals you would want to address before a sale, while those strategies are still available?

Sources from the notes: 26 U.S. Code 1060, purchase price allocation; 26 U.S. Code 1202, qualified small business stock; 26 U.S. Code 453, installment sales; IRS Revenue Procedure 2025-32, 2026 estate and gift amounts.

Chapter 9

The Day the Wire Hits: What Happens to the Proceeds

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. If your business sold this year, do you know where the proceeds would land, how much would be reserved for taxes, and what you would do in the first 90 days?
2. After a sale, how much of your net worth would still be tied to the buyer, your industry, or a single counterparty through rollover equity, earnouts, notes, or real estate?
3. Could you describe in writing what the proceeds are for and how much you could reasonably spend each year?

Sources from the notes: FDIC, Understanding deposit insurance.

Chapter 10

Life After the Exit: Purpose, Family, and Legacy

Self-check. Write your answers down. The ones you cannot answer yet are your to-do list.

1. Could you describe, in a few sentences, what you want your life to look like a year after you step away from the business?
2. Have you and your family talked openly about what a liquidity event would mean for each of you?
3. Which of the eight habits in this chapter are you practicing today, and which one will you start on next?