Perhaps one of the most powerful tax and business succession planning tools available to shareholders of a closely held company is the ability to sell stock to a trust created pursuant to an employee stock ownership plan (“ESOP”) and defer or permanently avoid taxation on any gain resulting from the sale. An ESOP also can increase commitment and productivity from employees and, in turn, produce greater share value, provided employees understand how their work affects share value. In order to generate these intangible benefits of broad-based employee ownership through an ESOP, employers must invest substantial time in developing an “ownership culture” (i.e., a general sense of responsibility for the success of the employer’s business plan, including a focus on limiting expenses and maximizing revenues) or in fostering a similar environment that already exists.

Consider this example of the tax advantages available for a sale to an ESOP. A shareholder who owns stock worth $3,000,000 in a closely held company (for which stock he or she originally paid $200,000) will pay $797,500 in federal and state income taxes on the sale (assuming a combined federal and state tax rate of approximately 27.5%). He or she will net $2,202,500, at best, from the sale. However, by selling the stock to an ESOP, he or she will pay no federal income taxes, and possibly no state income taxes, on the sale — potentially a $797,500 tax savings.

This tax deferral is available only if the following requirements are satisfied:

• The selling shareholder must be an individual, a trust, an estate, a partnership, or a subchapter S corporation (an “S corporation”) and have owned the stock sold to the ESOP for at least three years.

• The selling shareholder must not have received the stock from a qualified retirement plan (e.g., an ESOP or stock bonus plan), by exercising a stock option, or through an employee stock purchase program.

• The sale must otherwise qualify for capital gains treatment but for the sale to the ESOP.

• The stock sold to the ESOP (in general) must be voting common stock with the greatest voting and dividend rights of any class of common stock or preferred stock that is convertible into such voting common stock.

• For the 12 months preceding the sale to the ESOP, the company that establishes the ESOP must have had no class of stock that was readily tradable on an established securities market.

• After the sale, the ESOP must own at least 30% of the company that establishes the ESOP (on a fully diluted basis). Although not a requirement for the tax deferral, the company also must consent to the election of tax-deferred treatment and a 10% excise tax is imposed on the company for certain dispositions of stock by the ESOP within three years after the sale (and while the ESOP loan is outstanding, in certain circumstances).

• Within a 15-month period beginning 3 months before the sale to the ESOP and ending 12 months after the sale, the selling shareholder must reinvest the sale proceeds in qualified replacement securities (“QRP”) (common or preferred stock, bonds, and/or debt instruments) issued by publicly traded or closely held domestic corporations that use more than 50% of their assets in an active trade or business and whose passive investment income for the preceding year did not exceed 25% of their gross receipts. Ineligible reinvestment vehicles include municipal bonds, certificates of deposit issued by banks or savings and loans, mutual funds, and securities issued by the U.S. Treasury.

• The ESOP must be a C corporation, not an S corporation, at the time of the sale.

In addition to these, the company stock purchased by the ESOP generally may not be allocated to the seller, certain members of his or her family, or any shareholder in the company that establishes the ESOP who owns more than 25% of any class of company stock (at any time during the one-year period ending on the date of the sale to the ESOP or the date on which “qualified securities” are allocated to ESOP participants). A prohibited allocation causes a 50% excise tax to be imposed on the company, adverse income tax consequences to the participant receiving the allocation, and may result in disqualification of the plan with serious consequences (such as disallowance of deductions for contributions to the plan and other penalties).

A subsequent sale of the QRP will trigger the tax that had been deferred by the sale to the ESOP. To address this problem, an investment alternative known as a “floating rate note” has been developed.

Floating rate notes are publicly registered securities issued by upper-medium rated to highly rated companies. Investment advisory firms have helped bring to market a number of similar securities over the years. These floating rate notes often have a maturity of 60 or more years and bear a floating rate coupon indexed to 30-day commercial paper, LIBOR, or some other floating rate index. These securities also normally have call protection for 30 years. Floating rate notes can be margined up to 90% or more of their market value, if properly structured, allowing investors access to a substantial portion of their initial sale proceeds to create an actively managed portfolio without triggering any tax liability to the seller. The borrowing cost usually is the broker call loan rate (or, in recent years, a much better negotiated rate) plus a spread (in larger transactions, 50 basis points or lower), which is offset by the income earned on the floating rate notes. There are a number of traps for selling shareholders who do not properly structure their reinvestments in these securities. Accordingly, caution and due diligence is required.

Careful planning of the reinvestment of the ESOP sale proceeds is extremely important. The business owner that sells his or her company to the employees can create liquidity today while deferring capital gains taxes indefinitely. In the event of the selling shareholder’s death after the ESOP sale, his or her heirs will receive a stepped-up basis on the QRP, meaning the taxation on the sale of his or her business is avoided forever. With the help of a knowledgeable investment advisor, the selling shareholder also can design a well-diversified portfolio that can be rebalanced according to the changing fundamental and technical conditions of the capital markets. Gifting of QRP to a charitable remainder trust (“CRT”) is an alternative available to selling shareholders who want to establish an actively managed portfolio rather than buying and holding QRP in a well-diversified portfolio. If a selling shareholder has donative intent, this planning alternative has some merit. The primary drawback of this strategy is that, although the selling shareholder (and his or her family) may receive the income on the QRP transferred to the CRT during the selling shareholder’s lifetime, the principal will be transferred to the designated charities upon the selling shareholder’s death.

How does an owner go about selling 30% or more of his or her company to an ESOP? The first step is a feasibility study to determine whether the characteristics of the company are such that the owner is a good candidate for a sale to an ESOP. This study may involve conversations with a qualified employee ownership attorney or a full-blown written feasibility analysis prepared by an attorney or financial consultant.

If the circumstances are such that the ESOP alternative is feasible, the next key step is to obtain a professional valuation of the entire company and of the portion of the company that is being sold to the ESOP. A valuation by an independent appraiser is one of the requirements for a transaction between an ESOP and an owner of the company that establishes the ESOP. Under the Employee Retirement Income Security Act of 1974, as amended, and the Internal Revenue Code of 1986, as amended, the ESOP cannot pay more than fair market value for the shares that it purchases from the selling shareholder. The independent appraisal is used by the ESOP fiduciary (a board of trustees, an administrative committee, or an institutional trustee) to ensure that the ESOP does not pay more than fair market value for the shares, as determined as of the date of the sale. Based on case law, the ESOP fiduciary must conduct the proper due diligence to make this determination in good faith.

The ESOP plan document and the ESOP trust agreement also must be designed and implemented. If the company does not have adequate cash resources to finance the purchase of company stock by the ESOP, as is usually the case, the company must obtain a loan from a commercial lender, and loan terms (i.e., interest rate, prepayment penalties, commitment fees, costs, restrictive covenants, and collateral, to list a few) must be negotiated. In addition, a stock purchase agreement between the owner of the company and the ESOP must be negotiated and prepared.

The ESOP then typically borrows the money from the company, which, in turn, borrows from a commercial lender. Alternatively, the selling shareholder may agree to extend credit to the ESOP in exchange for a promissory note secured by the shares acquired with such extension of credit. The ESOP uses these loan proceeds to purchase company stock from the owner at no more than its fair market value, as determined by an independent appraiser and confirmed in good faith by the ESOP fiduciary as of the date of the purchase.

The company’s debt to the commercial lender is normally repaid over a five-to-seven-year term, and the ESOP’s debt to the company is normally repaid over ten years (or longer) with tax-deductible contributions by the company to the ESOP. The company, the ESOP, and the selling shareholders should work together to obtain the best terms possible for such financing. Collateral and personal guarantees (or the lack thereof) often are issues the parties may view differently and must be resolved. In an ESOP created by a C corporation, contributions to the ESOP used to pay the interest on the ESOP’s loan from the company are fully deductible. Contributions used to repay ESOP loan principal are deductible up to an amount equal to 25% of the total compensation paid or accrued to all participating employees, so long as not more than one-third of the contributions are allocated to “highly compensated employees.” Different (lower) limits apply for ESOPs established by S corporations.

Reasonable cash dividends paid on company stock acquired by an ESOP with an ESOP loan also are generally deductible by a C corporation plan sponsor to the extent they are used to repay that specific loan (provided the company that establishes the ESOP and issues the dividends is not subject to the alternative minimum tax, in which event, the dividends may not be fully deductible).

Under current law, S corporation ESOPs are exempt from the unrelated business income tax (UBIT). Thus, if an ESOP owns all of an S corporation, no current tax is imposed on the company’s income. (That income is eventually taxed because ESOP participants in S corporations are taxed on ESOP distributions, just as C corporation ESOP participants are so taxed.) Although various members of Congress have proposed revising or eliminating the exemption, no such law has passed to date.

As outlined above, an ESOP is a versatile financial and motivational tool by which a selling shareholder can obtain significant tax benefits in selling a portion or all of his or her company. An ESOP also can be used in connection with the spinoff of a division or corporate expansion or for acquisition planning. It also can be given a special class of preferred stock to minimize equity dilution, and it can be combined with or offered in addition to a 401(k) plan to attract human capital to a company.

Read also: Description and Purpose of an ESOP - Employee Stock Ownership Plan

Read also: Tax Incentives for Employee Stock Ownership Plans