As a business owner considering your exit, when you think about the question “What’s the money for?” is “paying income taxes” a high priority? Chances are you are looking for ways to reduce taxes on the sale of your business, increasing the resources available to fund the things that are higher on your list.

While taxes are one of life’s certainties, with careful advanced planning (ideally before entertaining any offers) you may find ways to reduce them.

Maximize what’s taxed at advantageous rates

Sometimes, a business sale isn’t the sale of a single “business asset”—it’s often considered the sale of the individual assets of the business (think inventory, intangibles like goodwill, capital assets, etc.) for tax purposes.

This means that some assets may be taxed as ordinary income when sold while others may be taxed at lower, advantageous long-term capital gains rates. It’s worth noting, there may be big differences between the top marginal rate for ordinary income and the top rate paid on capital gains.

We are not transaction tax experts, but we have seen a lot. Your CPA is well suited to weigh in on these nuances. That’s why it’s important to develop a relationship with a CPA who is proactive in helping you with this strategic planning, not someone who just checks the box on completing your tax returns each year.

Negotiate Allocations

As part of any prospective deal, you as the seller will need to negotiate with the buyer on just how much of the purchase price is allocated to capital assets vs. assets subject to ordinary income taxes.

While the IRS has guidelines on this, often there’s some flexibility as part of the deal-making. Your CPA and deal attorney are integral to this process and it is imperative that you consult with them on the negotiations.

If your business is a corporation, you may be able to sell your shares in the business in lieu of an asset sale, resulting in taxes at capital gains rates vs. ordinary income. A strategic CPA can help with choices surrounding the best legal structure for your business well in advance of any potential sale – they will deliver value by helping you minimize taxes where possible.

Consider receiving payments over time vs. lump sum

Installment sales may help provide some control over tax planning by spreading income from the transaction (and the accompanying taxes) over a number of years vs. a single year. Moreover, installment payments may help you stay in a lower tax bracket (meaning you may be able to prevent other sources of income from being taxed at higher marginal rates).

Having less taxable income in a tax year also means that you may benefit from even lower tax rates on long-term capital gains (potentially 0-15%).

Minimizing taxable income also has other benefits, including:

• Lower Medicare Part B & D premiums if you are age 63 or older (Medicare has a two year lookback period, so when you start at age 65, they will look at your income from two years prior)
• Lower threshold for AGI-dependent deductions, like deductible medical expenses, and possibly avoiding phaseouts for the full state and local tax deduction
• Reducing the likelihood of being subject to the additional 3.8% net investment income tax

Installment sales are not without risk and may not be the best solution given your unique circumstances or needs from a business sale. Keep in mind, you are depending on the ability of the buyer/new owner to make the payments they owe. Having a good understanding of “what the money’s for” and your personal needs from a business exit can help clarify this decision-making.

Consider your legacy. Does charity fit in?

In answering the question “What’s the money for?”, you may discover that you have sufficient assets to fund your desired lifetime spending and accomplish all of your other goals and priorities (gifting to family and friends, setting the next generation up for success, etc.) This may lead you to consider charitable donations.

There are various charitable giving vehicles that may be beneficial to fund as part of your exit strategy if you decide that charitable giving is a priority, including a Donor Advised Fund.

A Donor Advised Fund (DAF) allows you to make a tax-deductible donation (the fund itself is considered a 501(c)(3)), grow funds available for charitable giving by investing the donation in an allocation of your choosing, and granting money out to charities over time. Because the DAF is a charitable vehicle, earnings on investments compound tax-free – potentially supercharging your giving or creating a multi-generational charitable legacy. Donating to a DAF can reduce taxable income in a year when it is abnormally high (like having proceeds from a business exit) and pre-fund a charitable legacy, removing the worry about factoring in charitable giving from your personal portfolio in the future.

Additionally, you don’t have to donate cash from a business transaction. You could, instead, donate appreciated stocks or other assets you already own to remove future capital gains potential.

Know all options available

Selling a business is one of the most consequential financial decisions you’ll make. The difference between a reactive approach and a well-prepared one can be measured in hundreds of thousands of dollars, or more. The strategies above are worth knowing, but their value is almost entirely in the timing and coordination. Getting there requires the right team around you before a deal is on the table, not after.

At Monument, this is exactly the kind of pivotal moment we prepare for alongside our clients. Our wealth strategy work integrates tax planning, deal structure considerations, legacy goals, and what comes next, so that when the time arrives, you are moving forward with clarity and intention. If you think a business exit might be on your horizon, near or far, we’d welcome the conversation.

*Note: Monument is neither a law firm nor a certified public accounting firm and no portion of the blog content should be construed as legal or accounting advice. Please consult your CPA for tax advice.