Exit Planning Tools for Business Owners

family business

The Transfer Options Many Owners Don’t Consider

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Transfer OptionsIf you ask most business owners what their exit strategy is, they will tell you they intend to sell the business to a third party. It is the most straightforward-sounding option. Find a buyer, negotiate a price, sign some documents, and walk away with a check. The problem is that it may be the hardest option to execute successfully.

According to data from business broker associations, intermediaries fail to sell approximately eighty percent of the businesses they list. When you run the arithmetic on how many businesses are available for sale versus how many buyers exist in any given market, the odds for a typical owner are not encouraging. Yet most owners approach this as their principle plan, not just as a fallback.

Your job as an advisor is to help them understand the broader range of options before they commit to a strategy that may not work. It’s important to start that conversation early enough that the alternative options are still available.

Why the Default Option Is the Hardest One

A third-party sale requires a buyer who is willing to pay a price the owner finds acceptable, has the financial resources to complete the transaction, and is prepared to take on the responsibility of running the business without the current owner. That is a combination that doesn’t always present itself on demand.

It also exposes the owner to a process that most are not prepared for. First is the confidential marketing, then buyer qualification, then due diligence. If you get that far there’s a negotiation of terms, determining representations and warranties, and a transition period that may require the seller to remain involved for a year or more after the sale. It’s not unusual to have an earn-out that depends on performance during that time, or perhaps even afterwards.

The process is time-consuming, often emotionally difficult, and frequently results in a price below what the owner expected.

None of that means a third-party sale is the wrong option. It means it needs to be approached with realistic expectations and thorough preparation. Our job is to help the owner needs to the alternatives.

Option Two: The Internal Sale

Selling to employees or a management team is, in many cases, the most controllable exit option available to a business owner. It is consistently underutilized because it is consistently misunderstood.

The most common objection I hear is “My employees don’t have the money.” That is often not the obstacle it appears to be. A well-structured internal sale doesn’t require employees to show up with a check on closing day. It uses the cash flow of the business itself as the source of acquisition financing and may include equity compensation programs to allow qualified buyers to accumulate ownership over time.

The owner can often maintain control until they are paid. The buyer is someone who knows the business and has been trained to run it. The transition is gradual, planned, and far less disruptive to customers, employees, and operations than a third-party sale.

It typically takes five to seven years to structure and execute a leverage buy-out properly, which is why the conversation needs to start early.

Option Three: Family Succession

When a family member is being positioned to take over, the planning challenges are different but no less significant. Family succession is not merely a matter of adding the next generation’s name to the ownership documents.

The incoming generation needs to earn credibility with employees, suppliers, and customers. That requires time and working in the business in a way that builds genuine capability. The financial structure of the transfer needs to be clear, so the outgoing generation is reasonably compensated and the incoming generation isn’t saddled with debt that undermines their ability to invest in the business.

And the family dynamics relationships, expectations, and the old grievances that never quite got resolved, are present in every conversation. They don’t disappear because the topic is business. If anything, the stakes make them more vivid.

Advisors who can help a family navigate those dynamics are providing a genuinely valuable service.

Option Four: Planned Liquidation

This option is less exciting to talk about, but it is the right answer for more owners than anyone (especially those owners) wants to admit. If the business cannot realistically be sold for a meaningful multiple, or if the owner is the business in ways that can’t be separated, then the owner should run the business profitably for as long as they choose, pay themselves well, invest those proceeds appropriately, and wind down the company when they are ready.

That is not failure. That is a rational financial decision. A business that generates good income for its owner for twenty or thirty years likely has fulfilled its purpose, whether or not it sold at the end.

Helping an owner see that option clearly is serving them better than pursuing a third-party sale that the market won’t support.

Option Five: Watch and Wait

Some owners have built businesses with characteristics that make them attractive to specific buyers in specific market conditions. There may be an opportunity for a strategic acquisition by a competitor, a private equity roll-up of their industry, or a specific buyer who appears at the right moment.

An owner who has kept the business performing well, maintains clean financials, and has structured the company to be transferable is positioned to take advantage of those opportunities when they arise. Waiting for the right buyer is not the same as having no plan.

Your Role in Expanding the Conversation

Most owners default to the third-party sale because it’s the one they’ve heard of. They’ve never had an advisor sit down with them and lay out the full menu of options, and their potential given the circumstances of the owner and the business.

That conversation, done well, is one of the most valuable things you can offer. It positions you as the advisor who is thinking about their whole future, not just the transaction. And it gives you something to plan together, which is where the most valuable advisory relationships are built.

John F. Dini develops transition and succession strategies that allow business owners to exit their companies on their own schedule, with the proceeds they seek and complete control over the process. He takes a coaching approach to client engagements, focusing on helping owners of companies with $1M to $250M in revenue achieve both their desired lifestyles and legacies.

How to Transfer a Family Business to the Next Generation

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A family business goes on from generation to generation, and having a structured succession plan helps in minimizing the problems and smooths out the process. Family business succession planning is the structured process of legally, financially, and operationally preparing your business for a smooth ownership handoff, covering everything from IRS valuations to trust structures.

Only 30% of family businesses survive to the second generation, and skipping a formal plan is the #1 reason. The tax exposure alone (gift tax, estate tax, capital gains) can drain decades of business value if no one plans.

In this blog, we’ll cover the right methods to transfer a family business to the next generation, tax strategies, common mistakes, and what a strong advisory team looks like.

Why Family Business Succession Planning Matters

Family business succession planning protects the business you built. Without a business plan, your family business won’t survive an ownership transition.

According to the Family Business Institute, only 30% of family businesses reach the second generation, and only 12% survive into the third.

  • A clear succession plan reduces family conflict during the handoff
  • It protects business value from unnecessary estate and gift taxes
  • It gives the successor enough time to prepare for the role
  • It prevents forced sales when a health crisis or death triggers an unexpected exit

When Should You Start Planning an Intergenerational Business Transfer?

Start intergenerational business transfer planning 10 to 15 years before your planned exit. By the time health issues or retirement pressures arise, the best tax-saving options are already off the table.

Starting early matters because:

  • Successors need years of mentorship and practical training
  • Annual gift strategies work better when you have more years to execute them
  • A certified business valuation affects estate and gift tax filings
  • Legal structures, such as trusts, buy-sell agreements, and entity restructuring, take time to set up correctly

The IRS and estate planning attorneys consistently recommend beginning formal planning no later than 5 years before an exit. Ten years out is better.

Key Steps in Transferring Ownership of a Family Business

Transferring ownership of a family business is a structured process. Missing one step can stall the whole transition or create serious legal and tax problems.

Step 1: Set Clear Goals for the Business Transition

Decide what you actually want.

  1. Do you want retirement income from a sale?
  2. Do you want to keep an advisory role?
  3. Do you want equal ownership among your children or control given to one person?

Write these goals down. Share them with your family and your CPA before any documents are drafted. Vague goals produce vague plans, and vague plans produce conflict.

Step 2: Choose and Prepare the Right Successor

Not every family member who wants the role is the right fit. A good successor should have:

  • Relevant business or industry experience
  • Leadership skills the team already respects
  • A clear willingness to commit long-term
  • Enough financial literacy to manage operations

Start preparing the successor early. Shadow roles, incremental responsibility, and mentorship work far better than a sudden handoff on day one of retirement.

Step 3: Get a Professional Business Valuation

Before you transfer a family business to the next generation, get a certified business valuation. The IRS uses fair market value to assess taxes on any transferred business interest.

Use a Certified Valuation Analyst (CVA) or an Accredited Senior Appraiser (ASA). Their report must be defensible if the IRS questions the transaction, because a fabricated number won’t hold up.

Step 4: Develop a Leadership Transition Plan

A leadership transition plan outlines who will take over, when, and how responsibilities will shift. It should cover:

  • Key management roles and who fills each one
  • The timeline for the current owner’s exit
  • A communication plan for staff, clients, and vendors
  • Decision-making authority during the overlap period

Without this, employees and customers get nervous, and nervous people leave.

Methods for Transferring a Family Business

Transferring a family business to the next generation depends entirely on your goals, tax situation, and family structure.

Selling the Business to the Next Generation

You can sell the business to your children at fair market value or at a discounted price. An installment sale (where the buyer pays over time) is common because it generates ongoing retirement income for the seller while spreading the tax burden.

One structured option is a Self-Canceling Installment Note (SCIN). If the seller dies before the note is paid off, the remaining balance is canceled. Your CPA can determine whether this fits your situation.

Gifting Ownership Shares

The IRS allows annual gifts of up to $19,000 per recipient in 2025 without triggering gift tax. You can gift ownership interests in an LLC or S-corporation over many years.

Minority interest and lack-of-marketability discounts can reduce the taxable value of gifted shares by 20% to 40%. This strategy works best when you start it early and maintain consistency year over year.

Passing the Business Through a Will or Trust

A will transfers business interests at death, but it goes through probate, a public, slow, and expensive court process. A revocable living trust avoids probate entirely and gives you more control over how and when the business transfers.

Irrevocable trusts like GRATs (Grantor Retained Annuity Trusts) and IDGTs (Intentionally Defective Grantor Trusts) are also used in family business transition planning to shift value out of the taxable estate at a reduced cost. These are complex and require an estate attorney.

Creating a Buy-Sell Agreement

A buy-sell agreement sets the terms for ownership transfer in advance. It defines who can buy shares, at what price, and under what conditions, including death, disability, retirement, or divorce.

Without one, a child’s divorce proceeding can result in the forced sale of business interests to a non-family outsider.

Tax Considerations in Family Business Succession

Family business succession planning gets expensive without a tax strategy. The IRS has multiple ways to tax a business transfer, and each one can take a serious cut if you’re not prepared.

Gift Tax & Estate Tax Implications

In 2025, the federal lifetime estate and gift tax exemption is $13.99 million per individual or $27.98 million for married couples. Transfers above this get taxed at up to 40%.

This exemption is scheduled to drop by roughly half after 2025 unless Congress acts to extend it. That makes 2026 a critical year to lock in high-value transfers before the window closes.

Capital Gains Tax Considerations

If you sell the business to your child, you pay capital gains tax on any appreciation above your original cost basis. Long-term capital gains rates sit at 0%, 15%, or 20%, depending on your taxable income.

Assets inherited at death receive a “step-up in basis,” which eliminates capital gains tax on all appreciation during the owner’s lifetime. Assets gifted during life do not receive a step-up in basis. This affects whether you gift now or hold until death.

Strategies to Minimize Tax Burden

  • Use the $19,000 annual gift exclusion per recipient in 2025 to transfer shares over time
  • Apply business valuation discounts to reduce the taxable value of gifted interests
  • Use a GRAT to shift appreciation out of the estate at minimal gift tax cost
  • Consider an irrevocable life insurance trust (ILIT) to cover estate tax liability with tax-free proceeds
  • Plan wealth management decisions around the 2026 exemption sunset before it cuts the available exclusion in half

Managing Family Dynamics During the Transition

Family business transition planning that ignores the human side runs into problems even when the legal structure is perfect.

Balancing Fairness Among Heirs

Fairness doesn’t always mean equal. A child who worked in the business for 20 years and a sibling who pursued a different career are not in the same position. Equal ownership in that case creates resentment and operational problems.

Some families use life insurance to offset this. The business goes to the child who runs it. The other children receive equivalent value through insurance proceeds. It’s clean, documented, and it reduces the most common source of succession conflict.

Separating Ownership and Management Roles

Ownership and management are not the same thing. A child can hold shares without running daily operations. Establishing a clear governance structure (a family charter, an operating agreement, or a board) helps prevent role overlap and power disputes.

This matters most when multiple siblings own shares, but only one actually runs the business.

Common Mistakes in Family Business Transition Planning

Most failed transitions share the same mistakes. Watch for these:

  • Starting too late: Planning with 2 years left gives you almost no good options
  • Skipping the business valuation: The IRS won’t accept your best guess
  • No written succession plan: Verbal agreements fall apart the moment stress enters the room
  • Ignoring non-business heirs: Children outside the business resent being left with nothing
  • Letting family conflict delay the decision: Conflict doesn’t resolve itself. Bring in a mediator before it escalates

The Role of CPAs and Advisors in Succession Planning

Transferring ownership of a family business involves tax, estate, and business law, as well as valuation considerations.

A strong advisory team includes:

  • A CPA with direct business succession experience
  • An estate planning attorney familiar with trust structures
  • A certified business appraiser (CVA or ASA designation)
  • A financial planner focused on long-term wealth management goals
  • A family office advisory specialist for high-net-worth families with complex holdings

Family office services are increasingly common for business families managing large estates. They coordinate all advisors in one place, eliminating gaps and preventing conflicting advice from different professionals.

 

Amit Chandel  is a “Certified Tax Planner/Coach”, and “Certified Tax Resolution Specialist”. He has extensive experience in Tax Planning and Tax Problem Resolutions – helping his clients proactively plan and implement tax strategies that can rescue thousands of dollars in wasted tax and specializes in issues relating to unfiled tax returns, unpaid taxes, liens, levies, foreign bank account reporting, audit representation, and any other type of tax controversy; Financial Consulting; Business Planning, Business Valuation, Forensic Accounting and Litigation support. He is the recipient of the prestigious Certified Tax Planner of the Year Award-2017, bestowed by the American Institute of Certified Tax Planners.

The House of Gucci Succession Plan

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By now, you may have seen the movie House of Gucci. Lady Gaga and Al Pacino star in the true depiction of the Gucci family.

The Gucci brand started with two brothers who own the family business equally. Each brother had a son, and each son was to inherit the empire. One of the sons was a ne’er-do-well, who always attracted and found trouble. Despite nobody ever giving him a chance, the viewer could tell his successor ownership was doomed. The other son married the woman who was played by Lady Gaga. The story progresses through time as one of the fathers die and the other goes to jail while the wife rises to power and greed. To complicate the succession plan, lavish lifestyles, poor business decisions, children and divorce ensue.

The Gucci brand has always been iconic, and it remains so today. The movie describes the struggle between the two brothers and their ideas on how to grow the brand. One brother wants to expand into shopping malls across the world, while the other brother believes the idea of having a Gucci store in a mall is despicable. The two brothers who have these opposing views show how difficult it is running a family business with 50-50 ownership.

The two sons are the on-again/off-again heir apparent to the fortune, and eventually they will run or have a hand in running Gucci. The ne’er-do-well son struggles and is really off-base with his ideas, which are very inconsistent with the brand, and he lacks any sense of training or sense of how to run a business. Subplots in the movie describe how the other stakeholders attempt to circumvent his ownership and ultimately the rest of the family.

The other brother is smart, but he has a blind spot in that he has never had to struggle financially. He has never had to know what it was like to lack resources. His approach to management and growth are flawed because of the company culture and his paradigm. The influence of his wife and others around him also taint the management and success of a family run business. He lives lavishly, incurring personal expenses that he funds through the company.

Subterfuge and infighting ultimately become the demise of the family. The business survived but it was sold off for pennies on the dollar and was turned into a publicly traded company and as a result, the family no longer owns the business.

Clearly, the Gucci’s would have benefited from a team of exit planning advisors to help them navigate these waters! Indeed, there was no training of the sons, there was no alignment by the brothers, there was no dealing with the other stakeholders in the family. There was no financial planning, nor personal planning. Other than the brand quality, there was no development of cultural consistency or business attractiveness. There was a lack of management succession, planning and delineation of who does what. Sadly, there are many family run businesses that much less well known, but who lack the kind of exit planning that is needed to successfully pass along the business to the next generation.

House of Gucci illustrates how important it is for families to pay attention to succession and exit planning. I give this movie two thumbs up for the entertainment value of the movie, but two thumbs down on exit planning!

Mark Hegstrom is Certified Exit Planning Advisor and helps business owners to plan for what may be their single largest lifetime transaction: the transfer of their business. Get started by completing an exit readiness Assessment for yourself. Mark is Managing Partner at Business Owner Succession Strategies (BOSS). He currently serves as President of the Exit Planning Institute -Twin Cities Chapter.
 

Exit Planning – Lifestyle and Legacy

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Lifestyle and Legacy are two very different types of owner transition objectives.

When we ask a client “What do you expect as a result of our exit planning?” the answer may be about the money, the time frame, or the impact on people. No matter how it is phrased, the response will break down into one of two major categories. It’s either about the owner’s future lifestyle, or the legacy that is left behind.

Lifestyle Objectives

Many clients want to exit to an enjoyable retirement. Usually, their primary concern is financial security. They want enough money to live comfortably, and to take care of their family. This is the reason many start their process by consulting with a financial planner, but lifestyle objectives can extend well beyond their bank account.

A separate but related objective is time. It may be the time to travel without being chained to a laptop. The time to explore new things outside the business might result in formal education or training. Undertaking a new wellness regimen requires time, as does exploring a new hobby.

Time might be used to engage in community service. An issue that is increasing in the Baby Boomer generation is the time to care for older family members.

Another lifestyle issue is the ability to relocate. Moving to a place for favored activities, a better climate or to be closer to children (and grandchildren) often requires separation from the activities of the business.

Legacy Objectives

Some owners run their businesses for other than purely financial reasons. In these cases, they may be more concerned with how the business continues than the proceeds to be realized from a sale.

Of course, a chief motivation for putting legacy at the top of the list is family succession. It might be a sense of obligation in a company that has already passed through multiple generations, or just a desire to provide future generations with the benefits of ownership.

The role of the business in the community is also a legacy concern. The company could be a key employer in a small town, or a primary sponsor of a school or Little League. The owner’s name on the door or the preservation of long-standing business relationships can often affect the desirability of a buyer in the seller’s eyes.

Environment, Social, or Governance (ESG) concerns have become increasingly important to some sellers. They want to make certain that the importance they place on these issues is shared by future ownership.

Finally, the future growth and success of the business can be considered a legacy issue. An owner could have concern for the opportunities such growth provides to loyal employees, or whether innovations and proprietary processes will be expanded beyond their current limits.

Lifestyle and Legacy

Every owner’s objectives will have some combination of lifestyle and legacy concerns. They don’t necessarily conflict, but they involve differing perspectives.

John F. Dini develops transition and succession strategies that allow business owners to exit their companies on their own schedule, with the proceeds they seek and complete control over the process. He takes a coaching approach to client engagements, focusing on helping owners of companies with $1M to $250M in revenue achieve both their desired lifestyles and legacies.

Stakeholders in Exit Planning

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When preparing for the transfer of a business, there are many stakeholders who can impact your plan. Some have direct authority or decision-making capability over the transaction, but others may have substantial influence. In general, it’s best to presume that anyone who has a relationship with the owner or the business will have some impact on his or her decisions.

Internal Stakeholders

Of primary importance are partners and shareholders. Even when an owner has a voting majority, minority partners may have an official or unofficial veto. “Official” comes in the form of supermajority rights. Unofficial may be in the form of a threat to terminate employment, which in some cases may make the business unsaleable. If the minority holders are the intended recipients of the equity, they will function as both key components of the company’s value, and negotiators of the price to be paid for that value.

Employees are the other major internal stakeholders. Could they be a flight risk in the owner’s absence? Are they in danger of losing special status or privilege under new management? What is the plan for informing and updating them before and after a deal is struck?

Family

With most business owners, their equity in the business is 50% or more of their personal net worth. That makes future ownership, sale price and coordination with the estate plan items of great interest to spouses and children. In today’s serial family relationships, that can also involve step-siblings, former spouses, and their new partners’ families.

If there are children in the business, their future is inextricably tied to the company. If some children are in the business and some outside of it, the entitlements and expectations grow even more complicated.

Business Relationships

Customers may be transactional, as in retail, or strategic partners whose own business depends on what the company supplies. In such cases, or when customers are government entities, they may have contractual rights to approve a change in ownership.

In any case, the valuation of the business is going to depend at least partially on the retention of customers.

Suppliers have similar interests. We recently saw a distribution arrangement canceled simply because the supplier was insulted by not being informed about the company’s merger negotiations. The fact that they were conducted under a confidentiality agreement didn’t appease the supplier.

Creditors and lenders who hold personal guarantees are bound to be concerned about ownership changes. Be proactive in letting them know how their security interests will be preserved.

Public Stakeholders

StakeholderGovernment entities, especially any with regulatory responsibility over the industry, should also be approached proactively. Waiting for them to recognize a change may seem like “discretion as the better part of valor,” but untimely intervention could derail a transaction.

If the company is an important employer, a candidate for relocation, or a fixture in the community, some outreach to elected officials may be advisable.

Finally, consider the media. Plenty of business owners have complained about interviews that were slanted, reported inaccurately, or “just plain wrong.” If the transaction is newsworthy (and even if it isn’t,) prepare a professional announcement and a list of where it should be distributed. Refer to it, word for word if necessary, whenever someone calls for comment.

Thinking in advance about the impact of an exit plan on the various stakeholders can save advisors and their clients a lot of headaches when a deal is signed.

John F. Dini develops transition and succession strategies that allow business owners to exit their companies on their own schedule, with the proceeds they seek and complete control over the process. He takes a coaching approach to client engagements, focusing on helping owners of companies with $1M to $250M in revenue achieve both their desired lifestyles and legacies.