• High-net-worth individuals often have multiple income streams and need to coordinate tax strategies across entity types and asset classes.

• The proper structuring of investments can often have a significant positive impact on the economic gain realized.

• Start to plan at least 18 to 24 months before the sale of a closely held business to ensure proper structure, boost business valuation, and improve after-tax outcomes.

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You’ve built significant wealth. As a result, taxes have become more than just a line item in your budget — they’re a force that can quietly erode your returns, complicate your business exit, and reshape your legacy.

Fortunately, you have a window of opportunity to take control. Proactive tax planning can help you align today’s strategies with tomorrow’s vision — whether you’re juggling multiple businesses, eyeing a potential sale of an investment, or preparing to transition out of your company.

This article examines how to approach tax planning to maximize your earnings and stay ahead as tax laws shift.

Understanding the Tax Implications of Different Income Streams

The average high-net-worth individual typically has around seven income streams. These can include salaries and wages, pensions and annuities, interest, dividends, capital gains, rental and royalties, business profits, and more.

Each type of income can face different tax rules and rates — which makes planning across all sources critical.

For example, you might defer income into years where your marginal rate is lower (such as in retirement or during a gap year after a business sale), accelerate deductions in high-income years to offset earnings, or swap investment property using a 1031 like-kind exchange to defer recognition of capital gains.

Strategically harvesting investment losses can also help manage bracket thresholds and your exposure to the net investment income tax (NIIT).

Also, consider how you generate income through various entities. Sometimes, an investment’s structure can have a greater impact on tax outcomes than the investment itself.

For example, at the federal level, income from a C corporation is taxed at both the corporate (21%) and shareholder levels (up to 23.8% on dividends), resulting in effective tax rates that leave less than half of earnings in your control once you layer in state taxes. In contrast, S corporations and other passthrough structures may offer favorable pass-through treatment and qualify for a QBI deduction (20% of the business income).

Planning for Business Exits with Taxes in Mind

Selling a closely held business may be a once-in-a-lifetime event. The company may make up a large portion of your net worth and, with so much at stake, the tax treatment of the sale can dramatically alter the outcome.

We recommend that business owners start preparing for a sale at least 18 to 24 months in advance. But even if a sale isn’t on the immediate horizon, business owners should operate as though the company is always “for sale”. Opportunities often arise unexpectedly and financials that aren’t sale-ready can delay or derail a deal. Minimize all working capital kept in the business for at least the year preceding a sale. You will not be paid any more money for a business with a ton of working capital versus the minimum.

A knowledgeable CPA can help you identify red flags, clean up reporting, and implement strategies that improve the business’s financial profile so you’re prepared to act when the timing is right.

A longer timeline gives you runway to halt unnecessary reinvestment and boost earnings before interest, taxes, depreciation, and amortization (EBITDA) — directly affecting the sale price and reducing excess working capital.

Structuring the Deal

The structure of a sale plays a crucial part in the tax treatment of potential gains. Many sales of closely held businesses take the form of asset sales rather than stock sales, mainly because asset purchases offer more favorable terms to the buyer. When a buyer purchases the company’s assets, they avoid inheriting legacy liabilities and can allocate the purchase price among depreciable assets for future tax benefits.

However, even for transactions legally structured as a stock sale, buyers may use a Section 338(h)(10) election to treat the deal as an asset sale for tax purposes. This hybrid structure provides the buyer with the benefits of an asset acquisition while technically acquiring the stock.

From the seller’s perspective, both methods can yield similar tax outcomes. The gain from the sale typically flows through to the owner as a capital gain. If any portion of the purchase price is allocated to depreciated fixed assets, there may be a small amount of ordinary income due to depreciation recapture. As long as the owner is actively involved in the business at the time of sale, it’s generally exempt from the 3.8% NIIT.

In some cases, especially in deals involving private equity, buyers want to retain the existing owner’s involvement, so the buyer may acquire a majority interest and require the seller to continue managing the business. This is often structured through an F-reorganization, which allows for tax deferral on the portion of the business not immediately sold.

Another common feature of modern deals is the earnout: a portion of the sale price that’s paid over time based on the company’s future performance — usually tied to EBITDA targets. Earnouts can create significant tax planning opportunities and risks when they extend over several years.

Finally, for owners concerned about a large tax hit, investing the gain into Qualified Opportunity Zone (QOZ) funds can provide a way to defer capital gains and potentially reduce future taxes. This benefit was made permanent by the One Big Beautiful Bill Act.

Working closely with a CPA who understands these nuances allows you to align the terms of the sale with your broader financial goals.

Potential Section 1202 Tax Saving Strategies

Selling qualified small business stock (QSBS) may qualify for Section 1202 treatment. This tax provision allows individuals to avoid paying taxes on up to 100% of the taxable gain recognized on the sale of QSBS. The gain exclusion is worth $10 million or 10 times investment basis and applies to C Corporation stock issued after August 10, 1993, and before July 4, 2025, held for at least five years.

The recently passed One Big Beautiful Bill Act increases the Section 1202 exclusion for gain to $15 million or 10 times basis for QSBS acquired after July 4, 2025, and held for at least five years. There is a reduced gain excluded if the stock issued after July 4, 2025, is only held for three years (50% exclusion) or four years (75% exclusion).

Section 1202 creates an effective tax rate savings of up to 23.8% for federal income tax, and many states follow the federal treatment — resulting in even more substantial savings.

How MGO Can Help

Tax outcomes are rarely 100% predictable, but we can help shape them with foresight and planning.

Now is the time to take a closer look at your income, investments, and business interests. Don’t wait until the tax code changes. Schedule a planning session with an MGO advisor to start building a roadmap today.

The post Proactive Tax Planning Strategies for Exiting Your Closely Held Business appeared first on MGO CPA | Tax, Audit, and Consulting Services.

Last year’s Tax Cuts and Jobs Act, H.R. 1 (“the Act”) created a federal capital gains tax deferral program through the opportunity zone statute, which is designed to attract private, long-term investments in low-income and economically distressed communities. Over 8,700 communities designated as Qualified Opportunity Zones (QOZ), located across all 50 states, territories and Washington D.C, were nominated by local governments and confirmed by the Department of Treasury (DoT) in Notice 2018-48 issued in June 2018.

The statutory language of the Act introduced the tax incentive deferring taxable gains but it did not provide important details, including the types of gains eligible for deferral, the timing and specific requirements  of qualified investments, and how investors report deferred gains. On October 19, 2018, the Treasury Department released proposed regulations, a revenue ruling, and tax forms to provide additional guidance on the opportunity zone tax incentive.

How QOZ Tax Incentives Work

Simply stated, the opportunity zone statute allows for the deferral of capital gains if some or all of the amount of the capital gain recognized is invested in a Qualified Opportunity Fund (QOF) by an eligible taxpayer. A QOF is any entity that invests in qualified opportunity zone property and is taxed as a partnership or corporation organized in any of the 50 states, US territories, or D.C. The QOF is required to hold at least 90 percent of its assets in qualified opportunity zone property.

To defer a capital gain, a taxpayer has 180 days from the date of sale or exchange of the appreciated property to invest the recognized gain in a QOF. The potential tax benefits of opportunity zone statute include:

• Deferral of tax on capital gains invested in a QOF through 2019: Any recognized capital gain invested in a QOF through December 31, 2019 may be deferred until December 31, 2026 or eliminated when an investment in a QOF is disposed. There is an opportunity for taxpayers to make multiple investments in QOFs through the statute expiration date.
• Potential to eliminate 15% to 100% of taxes for capital gains invested: Capital gains invested in a QOF are deemed to have an initial tax basis of zero. The taxpayer receives a 10% increase in tax basis if the investment is held five years and an additional 5% increase in tax basis after seven years. If an investment in a QOF is held for ten years, the taxpayer can elect to increase their tax basis in the QOF to fair market value upon disposition, which provides for a tax-free investment in the QOF. Tax is realized on the excess of the deferred gain over the basis in the QOF at the time of disposal.
• Ability to rollover gains on disposal of investments in QOF: In general, the original deferred gain must be recognized by the taxpayer upon disposition of the investment in the QOF. If a taxpayer disposes of all of an investment in a QOF, triggering tax on the deferred gain and the qualified opportunity zone property, a taxpayer can make an investment in a new QOF and rollover the deferred gain. The rollover investment must be made before December 31, 2026.

Qualified Opportunity Zone Property

The purpose of the opportunity zone statute is to incentivize investment in low-income areas of the country in need of community development and improvement. IRC Sec. 1400Z-2(d)(2) provides guidance regarding the types of assets that will be considered qualified opportunity zone property if held by a QOF. In general, qualified opportunity zone property includes the following:

• Newly issued stock held in a domestic corporation if such corporation is a qualified opportunity zone business,
• Newly issued partnership interests in a domestic partnership if such partnership is a qualified opportunity zone business, or
• Qualified opportunity zone business property.

Qualified opportunity zone business property is further defined in IRC Sec. 1400Z-2(d)(2)(D) as tangible property used in a business in a qualified opportunity zone that is either:

• Land in a qualified opportunity zone,
• A building in a qualified opportunity zone that is first used by the QOF or the qualified opportunity business,
• A building in a qualified opportunity zone that was previously used but is “substantially improved” by the QOF or qualified opportunity business,
• Equipment that was never previously used in a qualified opportunity zone, or
• Equipment that was previously used in a qualified opportunity zone but it “substantially improved” by the QOF or the qualified opportunity business.

The opportunity zone statute defines “substantial improvement,” as an amount of investment in existing tangible property by a QOF, during any 30-month period, that exceeds the adjusted basis in the property at the beginning of the 30-month period. The Revenue Ruling issued clarifies that improvements made to land are not included in the total improvements for purposes of the “substantial improvement test” and the value of land is excluded from the adjusted basis calculations.

More Details on Qualifying as a QOF

The new guidance also provides details on what qualifies an investment vehicle as a QOF. And a draft of Form 8996, Qualified Opportunity Fund was released alongside the guidance to demonstrate how corporations and partnerships can self-identify as a QOF by including the form with the filing of their tax return. Additional information provided includes guidelines for determining when a QOF begins, how a QOF can meet the requirements to be recognized as a qualified opportunity zone business, and what pre-existing entities may qualify as a QOF. And finally, guidance details the test required of QOFs to determine whether the entity holds the minimum threshold of assets in qualified opportunity zone property.

Considering a QOZ Investment?

While the new guidance helps fill in many details, many questions are left unanswered and the Department of Treasury plans to release further guidance before the end of the year. If you’re planning on creating or investing in a QOF, we recommend consulting with an experienced tax advisor first.

The tax team at MGO is ready to assist you in navigating QOZs, QOFs, and other income tax concerns. For further guidance or to schedule a consultation, please contact us.

The post Quick Answers About Opportunity Zone Incentives appeared first on MGO CPA | Tax, Audit, and Consulting Services.