Financial Advisors for Post-Sale Planning

Kimberly Green | 2026-03-04

Financial Advisors for People Who Just Sold a Business Selling a business is one of the most financially complex events most people ever navigate. You go from having most of your net worth locked in an illiquid asset to suddenly having a large amount of liquid capital — and an enormous number of decisions to make, many of them time-sensitive and tax-sensitive. Most people underestimate how hard the first 12 months post-sale are. The decisions you make (or don't make) in that window matter more than almost anything you'll do financially for the next decade. The First 90 Days: Slow Down, Then Plan The most important financial advice for someone who just sold a business: don't move fast. The urgency you feel to "do something" with the proceeds is a psychological response to the transition, not a financial necessity. Park the proceeds in a high-yield savings account, money market fund, or short-term Treasuries while you build a plan. You're not losing ground — you're buying time to make good decisions. Don't make any major investment commitments for at least 60–90 days. The number of people who received $5M from a sale and immediately wrote checks to bad investments is not small. The capital gains tax bill is coming — know how big it is before you commit any of the proceeds to illiquid investments. Your estimated tax payment may be due sooner than you think. Deal Structure & Tax Implications (What Your Buyer Negotiated Matters) Not all exits are created equal from a tax perspective. These decisions can literally cost or save you hundreds of thousands of dollars. Stock sale vs. asset sale: Buyers often prefer asset sales (step-up in basis works for them); sellers generally prefer stock sales (lower capital gains rates on the sale price, no recapture tax). The negotiation on this point can be worth $200K–$500K+ depending on deal size. Installment sales: Spreading the sale proceeds over multiple years via seller financing can spread capital gains across tax years, potentially keeping you in lower brackets each year. Downside: you're taking credit risk on the buyer, and if they default, you have both financial and legal complications. Earnouts: Deferred consideration contingent on post-sale performance is taxed when you receive it — and the tax character (capital gain vs. ordinary income) depends on how it's structured in the purchase agreement. This matters more than most sellers realize. Qualified Small Business Stock (QSBS): If you held QSBS that meets Section 1202 requirements, up to $10M (or 10x basis) in gains may be excluded from federal tax. This is one...