Consider ESOPs as an Option

David O’Leary • January 29, 2019

Five million business owners will be reaching retirement age in the next few years. Often the next generation does not want to continue the business and it is often difficult to find a suitable third-party buyer. These owners should seriously consider the benefits of selling to an employee stock ownership plan (“ESOP”). ESOPs can provide considerable flexibility in structuring the sale, permitting the business owner to sell a part, or all, of his or her stock in a tax-efficient manner. It may also allow the business owner to retain control of the business after the sale.

What is an ESOP?

An ESOP is a special kind of qualified retirement plan designed to give employees an ownership stake in their company by investing primarily in the stock of the company. Most ESOPs are leveraged, which means that the ESOP uses borrowed funds to purchase company stock.

Benefits of an ESOP

Sale to an ESOP is the only strategy by which an entity can purchase stock of a selling shareholder using pre-tax dollars. In addition, if the company is a “C” corporation, a selling shareholder who sells to an ESOP may be able to defer (and in some cases, eliminate) income taxes on the sale of stock. If the company is an "S" corporation partially or completely owned by an ESOP, there is no tax on the ESOP's share of the company's earnings. These tax advantages and the increased flexibility of an ESOP can be a compelling alternative to other succession planning strategies.

In addition to providing significant tax benefits, the sale of stock by a shareholder to an ESOP may:


  • provide additional liquidity for selling shareholders
  • provide a market for the stock owned by minority shareholders
  • provide a “tool” for transferring business to other family members
  • provide financing sources and alternatives that might not otherwise be available
  • enable selling shareholders to get top value for their stock
  • enable selling shareholders to maintain control of the business following sale
  • maximize after-tax proceeds for selling shareholders and provide them with unique estate planning and tax-saving opportunities
  • provide significant tax savings to the company
  • provide more favorable terms and conditions of sale than what can be obtained from a third party buyer
  • allow easier negotiations, less due diligence and an earlier closing date as compared to sale to a third-party buyer
  • reward employees for their loyalty and allow them to participate in the future growth of the company

Characteristics of a Good ESOP Candidate

Good ESOP candidates are small or mid-sized companies that have solid operating performances, stable cash flows, and a quality senior management team. The importance of the management team cannot be over emphasized, as they are the ones who will run the company once the shareholder leaves. To be cost effective, the business should have a value greater than $3 million. Partnerships and LLCs are not eligible to sponsor ESOPs but there are ways to structure the transaction so that they can benefit from an ESOP.

ESOPs are a Hot Topic

The media has numerous stories of successful ESOP companies. ESOPs can be utilized by a company in almost any industry and the tax savings are often significant. If you are a business owner who is considering the sale of your company, an ESOP may be a valuable, tax-efficient tool that can be used to help you accomplish your objectives.

If you would like to discuss whether selling to an ESOP is the right solution for you, please contact me at 847-241-1793 or doleary@lavellelaw.com.

More News & Resources

Lavelle Law News and Events

Understanding Grandparent Visitation Rights in Illinois
By Elizabeth C. Thompson November 19, 2025
While Illinois law recognizes that grandparents can play a vital role in a child’s life, it also strongly defers to the rights of parents. A grandparent seeking visitation must overcome a high legal threshold and demonstrate that denial of contact would likely harm the child’s well-being.
Behind the Scenes of Our 2025 Food Drive Delivery Day!
By Lavelle Law Charities November 17, 2025
The 2025 Lavelle Law Charities Food Drive wrapped up excitingly on October 24, 2025! After weeks of heartfelt community giving, Lavelle Law team members personally delivered an enormous haul to the Schaumburg Township Food Pantry.
Impact of Partial Government Shutdown on IRS – Day 41
By Timothy M. Hughes November 10, 2025
Impact of Partial Government Shutdown on IRS – Day 41: Due to the current lapse in appropriations, IRS operations are limited. However, the underlying tax law remains in effect, and all taxpayers must continue to meet their tax obligations as normal.
$65 Million Sale of Business - Lavelle Law Success Story
By Business Law October 29, 2025
$65 Million Sale of Business – a Lavelle Law Success Story. We were able to effectively negotiate the terms of a complex sale in a manner that enabled both buyer and seller to achieve their objectives.
Free Event. Learn the nuts and bolts of Illinois condominium law.
By Stephen G. Daday and Robyn K. Kish October 27, 2025
Explore the nuts and bolts of condominium law and gain actionable strategies to navigate today’s condominium and HOA challenges in Illinois.
New law provides expanded protection for Illinois residents, increasing key debtor exemptions.
By Timothy M. Hughes October 15, 2025
The Illinois General Assembly enacted Public Act 1738, amending several provisions of the Illinois Code of Civil Procedure to raise debtor exemption limits effective 1.1.26. The new law provides expanded protection for residents, marking the most significant increase to the state’s exemption statutes in over a decade.
Be proactive and put your home in a trust to avoid the time, hassle, and expense of probate court.
By Heather A. McCollum October 13, 2025
A crucial estate planning tool that many people in Illinois overlook is putting their home in a trust. Placing your house in a revocable trust offers multiple benefits. It avoids probate, which can save your family time and money after your death.
IRS Has Started to Phase Out Paper Tax Refund Checks
By Timothy M. Hughes October 10, 2025
In response to Executive Order 14247 requiring the Internal Revenue Service to eliminate the use of physical checks, the U.S. Department of the Treasury announced that paper tax refund checks for individual taxpayers will be phased out.
Join us in our food drive efforts!
By Lavelle Law Charities October 1, 2025
The 2025 Lavelle Law Charities Food Drive benefiting the Schaumburg Township Food Pantry has begun! Join us in our efforts to bring food, dignity, and hope to residents in need who rely on the food pantry. The need is greater than ever this year, as the food pantry serves over 1,300 households each month!
Marital Agreements, Collaborative Divorce, and Child Custody
By Family Law September 24, 2025
Our experienced family law attorneys, Joe Olszowka, Annette Corrigan, and Kristina Buchthal Alkass, discussed three key areas of family law matters: prenuptial/postnuptial agreements, collaborative divorce, and child custody. This video is a recording of their presentation on September 17, 2025.
More Posts