According to CNBC, nearly half of professional advisors, or 45%, say clients spend too little time on tax and wealth transfer planning before selling a business, according to a recent BNY Wealth survey. Michael Paulus, founder of wealth advisory PCM Encore, said he left hundreds of millions of dollars on the table when he sold insurance tech firm Assurance IQ for $2.4 billion in 2019, and he said the best time to plan is two to three years before going to market.

The article outlines five steps for business owners seeking to reduce taxes on a sale. It says founders should first check whether they qualify for the qualified small business stock, or QSBS, exclusion, which can reduce capital gains taxes on stock directly acquired from a qualifying C corp. Under the One Big Beautiful Bill Act, the exclusion rose to $15 million for stock issued after July 4, 2025, from a prior maximum of $10 million or 10 times the original basis, whichever is greater, and partial benefits are available after three or four years. It also notes that owners can gift QSBS to non-grantor trusts, with Brian Gray of Gursey Schneider saying an entrepreneur could stack $45 million in deductions by gifting QSBS to three trusts.

The piece also says business owners can gift minority stakes before a sale, since illiquid minority interests are typically discounted by 20% to 35%, and that gifts made too late can draw scrutiny from the Internal Revenue Service. It adds that donating appreciated stock well before a transaction can preserve a charitable deduction and avoid capital gains tax, while waiting too long can cause the IRS to treat the transfer as a deemed sale. The article further says moving to a tax-friendly state such as Florida or Texas is more complicated than simply spending more than half the year there, because taxpayers must prove a new domicile. Finally, it says owners should weigh liquidity needs before using these strategies, since many require giving up equity well before a sale.