Estate Planning for Entrepreneurs and Business Owners

September 06, 2024 · 8 min read

Estate planning for entrepreneurs and business owners is critical. Success in business requires planning, commitment, and a strategic approach. Many new businesses take at least two or three years to turn a profit and twice as long to truly hit their stride. If you’ve created a business, you know that success doesn’t happen overnight. But do you know what will happen to your business if something unexpected impacts you or when you decide to step away? You will exit your business at some point. Planning for that moment now by incorporating the business into your estate plan can help to set up you and your family for a successful next chapter. Succession planning is more than contingency planning — it’s part of a growth strategy. One-Third of Business Owners Not Ready for Succession in 2024 Entrepreneurs share certain characteristics. They tend to be motivated, creative, flexible, risk tolerant, and to have a longer time-horizon perspective than the average 9-to-5 worker. But when it comes to estate planning for entrepreneurs and business owners, many become focused on short-term priorities associated with their day-to-day operations at the expense of planning for future succession, according to a 2024 survey from Edward Jones. More than half of U.S. business owners are over the age of 55, and the average age at which owners plan to pass on their business is 63. As they near retirement, these entrepreneurs are priming the country for what Edward Jones calls a “business succession boom” in the coming years. Only two-thirds of business owners, however, have prepared a business succession plan. The one-third that have yet to create a succession plan say they don’t view it as a priority, citing uncertainty about the future of the business (32 percent), uncertainty about where to start the planning process (32 percent), and an inability to identity a successor (26 percent). What Can Happen If You Fail to Plan Despite the uncertainty behind why some business owners don’t create a succession plan, the Edward Jones survey also reveals that most owners (88 percent) are confident their business will grow in the next 10 years. One can see why estate planning for entrepreneurs and business owners is so critical to have in place and keep updated. With a succession plan in place, those businesses could grow even more. Harvard Business Review cites research showing that proactive succession planning can increase company valuations and investor returns by 20 percent to 25 percent. Whether you intend to sell your business to fund retirement or pass it on to heirs as part of a lasting financial legacy, the leadership pipelines and succession practices you put in place today should be thought of as part of a broader business strategy to create continuity and value. Roughly one-third of entrepreneurs have no retirement savings plan. Around one in five plan to sell their business to fund their retirement. But executing a sale requires years of preparation. A three-year minimum window is recommended when selling a business to lay the groundwork for things like fine-tuning revenue streams and expenses and putting your books and management plan in order. Your business succession plan also needs to address the unexpected. Around half of all owner exits are involuntary due to one of the five “Ds”: Death, Disability, Divorce, Distress, or Disagreement. If your estate plan does not incorporate succession planning and you unexpectedly pass away, for example, state law could dictate that the business is split equally between your spouse and children. While they may already figure into your business succession plan, they might not — or maybe not in equal parts. There may also be a different person, like a current business partner or key employee, to whom you plan to hand over the keys. Your plan could also entail having an unrelated professional or ownership group in charge of running the business for the benefit of your loved ones. Planning gives you the power to choose what happens to your business when you step away — either voluntarily or involuntarily. But not having a plan can make you a bystander in your own enterprise. Risk in Business vs. Risk in Estate Planning Although embracing risk may have been necessary for building your business, an estate plan is better suited to doing things by the book. And failing to protect your business with a comprehensive estate plan is a risk you can’t afford to take. An estate plan should have clear operating instructions and accompanying legal documents that foster business continuity. Your individual talents are what made the business what it is, but a business that is based too much on your personality might not be built to stand the test of time. Managing successor personalities and expectations are a crucial part of business estate planning. If your business is family-owned, family infighting and relatives placed in the wrong roles can jeopardize the company. According to Edward Jones, about half of named successors are family members. You may be tempted to give a loved one the benefit of the doubt, or take a chance on them, when succession planning. In the long run, though, personal favors may not be doing anyone any favors if they lead to business failures. At the very least, your chosen successor — family or otherwise — should be involved with the business prior to taking the reins. Good communication is just as critical for a seamless succession plan as it is for a well-run business. To help set expectations and avoid surprises that could disrupt operations, communicate your plans with family and nonfamily stakeholders, explain your decision-making process, give them a chance to provide input, and get everyone working toward the same goal. Estate Planning Documents for Your Business Succession Plan Estate planning for entrepreneurs and business owners starts with the basics - create your will, durable power of attorney, and a health care directive. You can also place the business in a trust for estate planning purposes. Think carefully about who you give power of attorney to, because this individual will have the authority to transact business for you if you lose capacity. They need to understand not only how to run the business in your absence, but also the connections between your personal and business finances. If your business is organized as an LLC, for instance, comingling personal and business expenses can open you up to liability. A family member who’s currently involved in the business may be a good choice for power of attorney, but a trusted professional who can grasp your nuanced financial position and make informed, unbiased choices might be best. Buy-sell agreements also need to be incorporated into your business estate plan. A typical buy-sell agreement takes effect at the time of an owner’s death, incapacity, or some other circumstance that requires transferring a business ownership interest. It is intended to provide a clear, orderly process for transferring business interests by identifying things like how the company’s value is determined, what events trigger the buyout, and how the buyout is funded. Financial Advisors and Estate Planning Attorneys In addition to an estate planning attorney, an entrepreneur should include a financial advisor in their business planning. The Edward Jones succession survey found that just 37 percent of business owners are utilizing a financial advisor as a business succession resource. Combined financial and legal strategies may be superior for developing a succession plan. Even if a business owner has a solid succession plan, a financial advisor can help them with the specifics of implementing it. The Importance of Tax Planning for Entrepreneurs Tax law and planning for tax efficiencies comprise a key part of estate planning, particularly when an estate contains business interests and assets. Charitable contributions or creating a charitable entity can reduce estate taxes and benefit your heirs. Philanthropy is also an opportunity to extend your legacy to the wider community. Many tax-related legislative proposals are considered each year, but which laws will be enacted and how they will affect business and personal assets can be hard to predict. Tax legislation, which could be introduced under the next presidential administration and Congress in 2025, is one of the top reasons for revisiting an estate plan. Life and Disability InsuranceUse life and disability insurance to your business advantage. Life insurance can provide your family or other named beneficiary with an income source after you die. It can also guarantee an income stream for your business, allowing your company to continue operations in your absence. Life insurance is used to fund buy-sell agreements as well. Disability insurance provides coverage in the event of short- or long-term disability. Carry separate policies for family beneficiaries and the business. The latter should identify a key business partner or employee as a beneficiary. Maximize Business Value With Estate PlanningThe estate planning attorneys at Elville and Associates partner with tax and financial advisors to help business owners plan for an expected ownership transition as well as unexpected events like business breakups and bankruptcy. Keeping your estate plan up to date is no less important than creating an initial plan. Business plans need to be adjusted from time to time as things change, and so do business succession and estate plans. Don’t delay your succession plan another day: Contact the experienced estate planning attorneys at Elville and Associates today to start or update your planning. #elvilleeducation

Posted in:

Thinking about a life estate in Maryland? Learn the benefits, risks, Medicaid concerns, and alternatives before adding children to your deed.

Jan 19, 2026 in Blog

Life Estates in Maryland: When They Make Sense and When They Don’t

A life estate can be a useful planning tool for some Maryland families who want to protect a home, avoid probate, and plan ahead for the future. At the same time, life estates create permanent legal and financial consequences that are often misunderstood. Knowing when a life estate works well and when it creates long-term problems is essential before moving forward. This article explains how life estates function in Maryland, common risks families encounter, how life estates interact with Medicaid planning, and alternatives that may offer greater flexibility. What Is a Life Estate? A life estate allows more than one person to hold ownership interests in the same property at different times. In Maryland, this typically allows a parent to live in and control a home for life while naming children or other individuals to receive the property automatically after death. The person living in the home is called the life tenant. The individuals who will receive the property later are known as remaindermen. While remaindermen cannot take possession during the life tenant’s lifetime, they hold a present ownership interest in the property. Life estate deeds are often used to avoid probate, support long-term planning goals, and simplify the transfer of a home. These benefits must be balanced against the legal limitations created by the deed. When a Life Estate May Make Sense In limited situations, a life estate can serve a practical purpose. This is most common in straightforward family arrangements where a parent intends to remain in the home for life and wants the property to pass directly to a specific individual without probate. Life estates may also be considered when flexibility is not a priority and future long-term care needs are unlikely. Even in these situations, careful legal review is critical before creating the deed. When Life Estates Create Problems for Maryland Families Limits on Selling or Refinancing Once a life estate is created, the life tenant generally cannot sell or refinance the property without the consent of all remaindermen. This can create serious challenges if care needs change or the property must be sold to cover expenses. Some families explore tools such as a testamentary power of appointment or a nominee realty trust to increase flexibility, but these options require careful planning and are not appropriate in every case. Difficulty Changing Ownership Removing a remainderman from a life estate deed is far more complex than changing a beneficiary on a financial account. Once added, that ownership interest is legally significant and often cannot be undone without consent or legal action. Exposure to Remainderman Issues After a remainderman is added to the deed, their legal and financial issues may affect the property. Court judgments, tax liens, divorce proceedings, or bankruptcy can complicate ownership and create unexpected risks. If a remainderman passes away before the life tenant, their interest may pass through their estate, potentially requiring probate and introducing new parties into the ownership structure. Medicaid Look-Back Concerns Creating a life estate involves transferring a property interest. If long-term care is needed within five years of that transfer, Maryland Medicaid rules may impose a penalty period. Timing and structure matter, and mistakes can be costly. Nursing Home Recovery Risks If the home is sold while the life tenant is receiving nursing home care, the state may assert a claim against the proceeds to recover Medicaid benefits paid. This outcome often surprises families. Life Estates and Medicaid Planning in Maryland A common misconception is that a life estate automatically protects a home from Medicaid. While a life estate may avoid probate, it does not replace a comprehensive Medicaid planning strategy. Medicaid planning is highly timing-sensitive and should be coordinated with broader elder law goals. Families often benefit from reviewing life estates alongside other options discussed in our Maryland elder law resources. Alternatives That Offer Greater Flexibility Depending on family goals, other planning tools may provide better long-term outcomes. Revocable trusts, irrevocable trusts, and coordinated elder law planning strategies often allow for asset protection while preserving flexibility and control. These approaches may integrate more smoothly with Medicaid planning and incapacity planning and can reduce risk as circumstances change. Reviewing a Life Estate as Part of a Larger Plan Life estates affect more than property ownership. They influence taxes, Medicaid eligibility, and the ability to respond to future care needs. For this reason, they should always be evaluated as part of a broader estate and elder law plan rather than used in isolation. If you are considering a life estate or already have one in place, guidance from a Maryland elder law attorney can help clarify risks and identify options before a crisis occurs. To schedule a confidential consultation, contact us online, call our Columbia office at 443-339-5638, or reach our Rockville office at 240-456-1657.

Jan 13, 2026 in Blog

Life Estates in Maryland: Benefits, Risks, and Better Planning Options

A life estate can be a helpful tool for Maryland families looking to protect their homes, avoid probate, and plan for Medicaid. It is important to understand the risks involved. This article explains common life estate issues and why careful legal planning matters before deciding if this approach fits your situation. What Is a Life Estate? A life estate allows multiple people to hold interests in the same property at different times. In Maryland, this often means a parent keeps possession and use of their home while ensuring it passes to their children without going through probate. By creating a life estate deed, families may avoid probate, reduce Medicaid exposure, and receive a step up in tax basis. The person living in the home is known as the life tenant and retains control during their lifetime. The individuals who inherit the property are the remaindermen. Although they cannot take possession until the life tenant passes away, they hold a current ownership interest. When a Life Estate May Still Be Appropriate In limited situations, a life estate can serve a practical purpose. Some families use a life estate when a parent wants to remain in the home for life and ensure the property passes directly to a specific individual without probate. This is most common in straightforward family situations where long term care needs are unlikely and flexibility is not a primary concern. Even in these cases, careful review is important. A life estate permanently alters property rights, and future changes often require agreement from all parties involved. Five Issues Maryland Families Should Know 1. Limits on Selling or Borrowing Against the Property A life tenant generally cannot sell or refinance the property without agreement from all remaindermen. A testamentary power of appointment may allow the life tenant to change who inherits the property through a will, providing additional flexibility. A nominee realty trust may allow one or more children to act as trustee for all remaindermen, with decisions made by majority vote. This can be helpful when family members disagree. 2. Difficulty Removing a Remainderman Removing a remainderman from a deed is far more complex than changing a beneficiary on a financial account. In many cases, removal is not possible without consent or court involvement. 3. Legal Issues Affecting the Property Once a remainderman is added to the deed, their financial or legal issues may affect the property. Court judgments or tax liens may attach to the home Divorce or bankruptcy can complicate ownership If a remainderman passes away before the life tenant, their estate may require probate These issues may not force the life tenant to leave the home, but they can create significant complications. 4. Medicaid Look Back Period Transferring a property interest through a life estate can affect Medicaid eligibility if long term care is needed within five years of the transfer. 5. Nursing Home Reimbursement If the property is sold while the life tenant is in a nursing home, the state may have a claim against the sale proceeds to recover care costs. Why Life Estates Often Create Long Term Challenges Many families create life estates without fully understanding the limitations involved. Selling or refinancing the property usually requires consent from the remainder beneficiary, which can become problematic if care needs change or funds are needed. Life estates also expose the property to risks tied to the remainder beneficiary. Financial hardship, divorce, or creditor claims affecting that individual can impact the property even while the life tenant continues to live there. Life Estates and Medicaid Planning in Maryland A common misconception is that a life estate automatically protects a home from Medicaid rules. While a life estate may avoid probate, it does not automatically shield the property from Medicaid eligibility requirements or recovery claims. In some situations, transferring a remainder interest can create a Medicaid penalty period if it is not structured properly or completed at the right time. Because Medicaid planning is highly timing sensitive, a life estate should never be used as a substitute for a comprehensive elder law strategy. Alternatives That Offer More Flexibility Than a Life Estate Depending on a family’s goals, other planning tools may provide better long term results. Revocable trusts, irrevocable trusts, and coordinated elder law planning strategies may offer asset protection while preserving control and adaptability. These options often integrate more effectively with Medicaid planning and incapacity planning. Choosing the right structure depends on health, family dynamics, finances, and anticipated care needs. A solution that works well for one family may create serious limitations for another. Is a Life Estate the Right Option? For some Maryland residents, life estates can provide benefits, particularly when probate avoidance is a primary goal. The risks involved mean this approach is not appropriate for every situation. Understanding both the legal and financial impact is critical. Reviewing a Life Estate as Part of a Bigger Plan Life estates affect more than property ownership. They impact taxes, Medicaid eligibility, and a family’s ability to respond to changing circumstances. For this reason, life estates should be reviewed as part of a broader estate and elder law plan rather than used alone. If you are considering a life estate or already have one in place, speaking with a Maryland elder law attorney can help clarify risks and identify options before a crisis occurs. To schedule a confidential consultation, contact us onlin e, call our Columbia office at 443-339-5638, or dial 240-456-1657 to reach our Rockville office.

2026 Maryland Super Lawyers and Rising Stars Lists

Dec 19, 2025 in Blog

Managing Principal Stephen Elville, Principal Attorneys Shannon Goodwin and Shannon Ladner, and Associate Attorney Sara von Stein Echeverria Honored on the 2026 Maryland Super Lawyers and Rising Stars Lists

Authored by: Jeffrey D. Stauffer – Community Relations Director It was announced on Friday, December 19 th that Managing Principal Stephen Elville, Principal Attorneys Shannon Goodwin and Shannon Ladner, and Associate Attorney Sara von Stein Echeverria were honored on the 2026 Maryland Super Lawyers and Rising Stars Lists. Stephen R. Elville, J.D., LL.M. — Managing Principal Stephen R. Elville, President, CEO, and Managing Principal of Elville & Associates, P.C., has again been selected to the 2026 Maryland Super Lawyers List — his 11th overall and 10th consecutive year receiving this recognition. Mr. Elville’s practice centers on helping individuals and families through challenging legal landscapes with clarity, compassion, and technical skill. He leads the firm’s work in estate planning, elder law, special needs planning, tax planning and asset protection and preservation, long-term care planning, and more. Clients working with Mr. Elville benefit from his deep experience navigating both pre-crisis planning and complex crisis situations — giving them peace of mind and a personalized, long-term strategy. Throughout his career, Mr. Elville has built a reputation as one of Maryland’s most respected attorneys. His broad legal-technical knowledge, combined with a caring and client-focused approach, enables him to address a wide range of legal matters with confidence and clarity. In addition to his client work, he is a seasoned educator and speaker, regularly offering webinars and workshops for clients and the surrounding community, along with continuing education events for financial advisors. Mr. Elville is an active member of several professional organizations including the National Association of Elder Law Attorneys (NAELA), WealthCounsel, the Academy of Special Needs Planners, and as well as the EPIC Peer Group where he travels around the country each quarter learning from and teaching likeminded attorneys. He has held leadership roles including the past Chair of the Estates & Trusts & Elder Law Sections of the Howard County Bar Association, past President of the Coalition of Geriatric Services (COGS), and past Chair of the Elder Law & Disability Rights Section Council of the Maryland State Bar Association. He was also the long-term Chair for Law Day Maryland and recently served as Chair of the Pro Bono Subcommittee of the Elder Law Disability Rights Section Council. Outside of his legal practice, he is President of the Friends of Baltimore Classical Music, Inc. and Founder of the Elville Center for the Creative Arts, Inc. — a nonprofit dedicated to furthering music education for students with limited means. Mr. Elville had a feature story written about him in the national Super Lawyers Magazine about the Elville Center and his efforts surrounding this initiative. Along with his charitable endeavors, Mr. Elville also supports community organizations such as the Autism Society of Maryland, the Brain Injury Association of Maryland, the National Alliance on Mental Illness of Howard County, the Howard County Public Library System Veterans Book Group program, and more. Shannon Goodwin, J.D. — Principal Attorney Shannon Goodwin has been named to the 2026 Rising Stars List for a third consecutive year. In her role as Principal Attorney, she leads Elville and Associates’ Estate and Trust Administration Department along with estate planning and tax planning. Ms. Goodwin guides clients through every aspect of administering estates — from the probate process and inventory reporting, to accountings, final distributions, and all detailed estate tasks. Her insight and dedication help families navigate what can often be complicated and emotionally difficult processes. Her background includes undergraduate studies at North Carolina State University, followed by law school — during which she distinguished herself as a member of the Syracuse Law Review. After graduation, she gained important legal experience working as a Judicial Law Clerk for three years in the Circuit Court for Washington County, and in the District Court for Washington and Frederick Counties. She joined Elville and Associates in 2021, bringing with her a strong foundation and commitment to client care. Shannon F. Ladner, J.D. — Principal Attorney Shannon F. Ladner has earned her place on the 2026 Rising Stars List for the fourth year in a row. She leads the firm’s Estate Planning Department, where she assists clients through every stage of planning — from initial consultation to plan design and implementation, and ongoing updates as laws and life circumstances evolve. Ms. Ladner’s practice emphasizes estate planning and special needs planning. Her work is grounded in a thoughtful, client-centered approach, ensuring that each plan reflects the client’s values, goals, and unique family situation. During law school, she contributed her talents to the Human Trafficking Prevention Project Clinic, representing victims of human trafficking as a Rule 19 Student Attorney. After receiving her J.D., she served as a Judicial Law Clerk for Magistrates Susan M. Marzetta and Lori Joy Eisner in the Circuit Court for Baltimore City. Before joining Elville and Associates, she practiced at a small law firm in Towson, Maryland where she gained valuable experience representing clients in family law and criminal matters. Sara von Stein Echeverria, J.D. — Associate Attorney 2026 is Sara von Stein Echeverria’s first of what we see as many future inclusions on the Maryland Rising Stars list. Ms. von Stein Echeverria focuses her practice on estate planning, estate and trust administration, special needs planning, asset protection, and tax planning. She is known for her thoughtful, client-centered approach and her ability to guide individuals and families through complex planning decisions with clarity, empathy, and care. Sara works closely with clients to develop comprehensive plans that protect loved ones, reflect personal values, and provide long-term peace of mind. Sara earned her Juris Doctor, summa cum laude, from the University of Baltimore School of Law, where she distinguished herself through academic excellence and legal scholarship. She also holds a Master of Science from Birkbeck College, University of London, and a Bachelor of Arts, cum laude, from Dickinson College. Prior to joining Elville and Associates, her work included humanitarian and immigration-related legal advocacy, experience that continues to inform her compassionate and inclusive approach to client service. Sara is admitted to practice in Maryland and is an active member of the Maryland State Bar Association, the American Bar Association, and the Baltimore City Bar Association. To learn more about this year’s honorees and the entire team at Elville and Associates, please visit www.elvilleassociates.com. The firm is steadfast in its commitment to client education, compassionate legal service, and providing peace-of-mind solutions across estate planning, elder law, special needs planning, and beyond. Super Lawyers, a Thomson Reuters business, is a rating service of outstanding lawyers from more than 70 practice areas who have attained a high degree of peer recognition and professional achievement. The annual selections are made using a patented multiphase process that includes a statewide survey of lawyers, an independent research evaluation of candidates and peer reviews by practice area. The result is a credible, comprehensive and diverse listing of exceptional attorneys. The Super Lawyers lists are published nationwide in Super Lawyers Magazines and in leading city and regional magazines and newspapers across the country. Super Lawyers Magazines also feature editorial profiles of attorneys who embody excellence in the practice of law. For more information about Super Lawyers, visit SuperLawyers.com. #elvilleeducation