Exit Planning Tools for Business Owners

exit strategies

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.

The 3% Problem in Advisory Work: A Guide for Business Owners

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As a business owner, you belong to a unique group that makes up only 3% of the population. Yet, many advisors treat you like any other client—using the same approaches they apply to executives, professionals, or retirees. This is a fundamental misunderstanding that can impact your business and personal goals.

Why You’re More Than Just an Asset

You are not simply a high-income individual with concentrated wealth. Your business is not just an investment; it’s an integral part of your identity, your livelihood, and your daily purpose. It is the source of your authority, reputation, and even your personal satisfaction.

Navigating Identity, Not Just Assets

When traditional clients seek advice, the focus tends to be on optimizing their assets. In contrast, advising business owners like you involves navigating a complex web of identity and emotional attachment. This distinction is crucial and affects how you engage with advisors.

Understanding the Owner’s Perspective

The Structure of Your Business

Unlike executives who operate within established frameworks, you are the architect of your business’s structure. If a senior executive makes a mistake, it usually impacts their bonus. But for you, a misstep could jeopardize payroll, credit lines, or even your family’s financial security.

This creates a protective and cautious mindset that many advisors fail to recognize. Your business is not just an income engine; it’s something you’ve built, defended, and refined over years. Every employee, system, and brand element bears your imprint.

The Impact of Structural Suggestions

When an advisor casually suggests changes, it can feel less like strategy and more like criticism. Understanding this emotional landscape is vital; without it, you may resist recommendations that could genuinely benefit your business.

The Challenge of Decision-Making

As a successful entrepreneur, you are wired for decision-making. The constant loop of “What if we tried this?” fuels your creativity and drive. However, many traditional advisory engagements can lead to implementation failures:

1. Data Analysis: The advisor reviews your business metrics.
2. Recommendations: They develop a plan based on their findings.
3. Owner Response: You agree with the plan—but then take no action.

This isn’t about disagreement; it’s about ownership. You’re more likely to implement decisions you help create. This is why coaching before advisory work is essential, especially in exit planning.

Identity: The Key Variable in Exit Planning

Advisors often zoom in on valuation, tax efficiency, and succession logistics. While these aspects are important, the critical question you must consider is:

“What will you do when you no longer own this business?”

If your answer is vague—like “I’ll figure it out later” or “I’ll travel” —then your exit plan is likely incomplete. Liquidity without purpose can lead to regrets.

The Realities of Post-Exit Life

Research shows that 75% of former business owners report dissatisfaction a year after exiting. This is rarely due to financial shortcomings; it’s often because they haven’t redefined their identity.

As a business owner, you are exiting more than just an asset—you are relinquishing your relevance. Recognizing this early in your planning can lead to far better outcomes.

Conclusion: A Call to Action for Business Owners

Navigating the complexities of your business and its impact on your identity requires a unique approach from advisors. By understanding the emotional and psychological aspects of ownership, you can foster more meaningful relationships with your advisors.

If you’re contemplating exit strategies or want to redefine your post-business identity, consider engaging with a coach or advisor who recognizes these unique dynamics. Your business is your legacy; make sure your exit plan honors that.

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.

The Exit Planning Fallacy – A Business Owner’s Perspective

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One of the most common sales pitches you might hear from someone claiming to help you “enhance value” goes something like this:

“I’ve reviewed your company and believe it’s worth $4.2 million today. With the right planning, it could be worth $7.7 million. Would you rather exit with $4.2 million or $7.7 million?”

That’s not really a question—it’s a setup. Of course, no business owner would willingly choose the smaller number. But the real issue isn’t which number you prefer. It’s what it actually takes to bridge that gap—and whether you’re being given a full picture.

Are You Falling for the Planning Fallacy?


There’s a psychological term for this overly optimistic way of thinking: the planning fallacy.

A private equity investors group I follow, Chenmark.com, once cited a study published in the Journal of Personality and Social Psychology that perfectly illustrates the concept:

From a psychological perspective, the planning fallacy can perhaps be studied most profitably at the level of daily activities. Consider one familiar example: Academics who carry home a stuffed briefcase full of work on Fridays, fully intending to complete every task, are often aware that they have never gone beyond the first one or two jobs on any previous weekend.

The intriguing aspect of this phenomenon is the ability of people to hold two seemingly contradictory beliefs: Although aware that most of their previous predictions were overly optimistic, they believe that their current forecasts are realistic. It seems that people can know the past and still be doomed to repeat it.

What’s fascinating is that they know this pattern. Yet, every weekend, they’re sure this time will be different. Business owners do something similar: despite knowing how long things usually take (and how unpredictable growth can be), we still believe “this time” will follow our best-case forecast.

You may hear that big valuation potential and think, “Yes, that’s what I’ve always wanted—to grow the company by 83%! I just needed a plan.”

But a plan alone isn’t enough. It’s a start—but not the whole story.

What Really Closes the Gap?


Let’s reframe that optimistic pitch with a more realistic one:

“To grow from $4.2 million to $7.7 million in five years, you’ll need proper planning, dedicated effort, some strategic hires, and reinvesting a significant portion of your profits. That requires growing the business 19% annually—starting immediately. That’s more than double your best year to date. If you spend a year building that foundation first, then you’d need to grow at least 25% annually over the next four years. If you keep growing at your best year’s rate of 7.5%, it will take over 12 years to reach that goal.”

Those are the facts. And the reality is that very few business owners hit those growth rates without serious changes—and trusted advisors to help them.

The Power of Perspective (and the Right Guide)


You may have a solid company. It supports your lifestyle, your employees, and your reputation. Maybe you’ve even dreamed of taking it further. But the risks, the effort, or the lack of a clear roadmap have held you back.

That’s exactly where experienced advisors come in—not to promise easy gains, but to help you map a realistic path to your goals. They help align what you want (your proceeds), with what you’re willing to do (your effort), in the time you have left (your exit timeline).

In our work, we use a Value Gap coaching model that considers four essential pieces:

1. Current business value
2. Your desired outcome—not just “more,” but a specific number
3. The timeframe in which you want to exit
4. The required growth rate to get there

Often, once those last two are on the table, the conversation changes. It’s not just about the money—it’s about what you’re willing and able to do to get there.

The real planning fallacy? Believing it’s just about hitting a number. The truth is, getting the outcome you want depends on understanding the full picture—and working with an advisor who helps you navigate it honestly, strategically, and with clarity.

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.

Decisions Made from Fear

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“I’m taking the logos off my trucks. It just makes them a target for personal injury lawyers.”

“I don’t want to put our newest product innovations on our website. The competitors just copy them.”

“We’re creating a human resources LLC so that employees are separated from the rest of our business. That way we’re safer from spurious claims.”

“We pay all of our employees to bring their vehicles back to the yard every night. We don’t want to be responsible for what they do on their own time.”

“We were thinking of opening a new location, but the news says the economy might dip.”

“I thought about hiring another salesperson, but I can’t be sure they’ll pay for themselves.”

“Our margins are shrinking, but a price hike may cost us customers.”  

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When Fear Dictates Decisions

I can’t. We won’t. I shouldn’t.

Sound familiar? These thoughts creep in as your business grows. You’ve overcome a lot already—taking that first leap, pushing through uncertainty, making tough calls when the stakes were high. But now, you have something to lose. The fear of getting it wrong can paralyze progress.

There’s a well-known quote from Elon Musk. When asked, “What words of encouragement would you give to an entrepreneur?” he answered, “If you need words of encouragement, don’t become an entrepreneur.”

Starting a business meant stepping into the unknown. You did it once—and maybe you’ve forgotten how much courage that took.

There’s a saying worth remembering:

“We know about half of what we need to know. Another 25% is stuff we know we don’t know. The last 25% is stuff we don’t know that we don’t know.”

It’s that last 25% that causes the most anxiety. The unknowns we haven’t even considered yet. They can stop us in our tracks.

So we do what feels safest: nothing. Better to protect what we have than risk the comfort of the present for the uncertainty of the future.

But here’s the truth: staying still isn’t safe. It’s just quietly risky.

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Exit Planning: A Different Kind of Fear

Thinking about life after your business? You’re not alone if that brings up more questions than answers:

• What will I do with myself?
• Who am I without this business?
• Will I still feel needed or fulfilled?

That’s why most business owners don’t have an exit plan. It’s not urgent, it’s not easy—and frankly, it’s intimidating.

But the transition will come. The sooner you face it, the more options you’ll have—and the better prepared you’ll be.

This is where an experienced advisor is invaluable. A good advisor doesn’t just help you plan for exit—they help you clarify your goals, address the unknowns, and convert fear into forward motion.

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Turn Unknowns Into Strategy

Entrepreneurs are natural goal-setters. You’re wired to chase progress. With the right guidance, the fears that hold you back become challenges you can tackle.

Working with an advisor brings structure to uncertainty. It moves you from:

• “I don’t know where to start” to “Here’s the next step.”
• “What if I make the wrong decision?” to “I’m making informed choices.”

You’ve already taken one of the boldest risks in starting your business. Don’t let fear dictate what comes next.

Partner with someone who knows the road ahead—and can help you navigate it.

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.

Build a Successful Business Exit Plan by Using a Planning Process

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As a business owner, planning the exit from ownership of your business is probably the single most important decision you will make. When to exit, how much to walk away with, who to sell it to, what’s the most tax efficient strategy in your circumstance, what timeline is most suitable, and what are the areas of business that need to be improved upon to make it marketable, etc.? Those are just some of the things that need to be considered.

The challenge for many business owners is they don’t want to think about it until they’re absolutely ready to exit. The problem with that is, you won’t know when that will be, and it may happen unexpectedly, due to health and so forth. Furthermore, and especially with “baby boomer” owners, their business is everything to them – They don’t want to think about letting go, so they put it off. Plus, even if they do sell, what are they going to do when running their business isn’t with them every day. – What’s going to be their purpose when that comes to an end? So, they put it off, and when they decide to exit, the business may be unprepared to sell, the market may not be favorable, or they won’t get the price that they thought they would.

All of what I just mentioned, can be addressed or avoided with the proper business exit plan. A proper business exit plan should be done by applying an organized process. It is also important to remember that building a solid exit plan takes time. It’s nothing that you simply flip a switch, and presto, you have a solid exit plan. There are many things to consider, advisors you need to bring in the mix, data that needs to be collected, and analysis that needs to be performed.

Over the years in consulting my business owner clients, I have developed a “business exit planning process.” The diagram below is an illustration of that process. It breaks the process into three separate phases: “Create A Game Plan”, “Plan Development”, and “Implementation.”
 

The “Create a Game Plan” phase is the initial phase of the exit planning process. This includes completing an exit plan assessment, which determines what areas you will need to address in order of priority, determining your vision for the future (after you have exited), how much you will need to walk away with, whether to sell to a third party or an insider, performing a preliminary valuation, and assembling your team of advisors.

For performing an exit plan assessment, I use a tool called “ExitMap”, which is a handy tool and takes the client 15 to 20 minutes to complete. Determining your vision for your future, is a discussion of the owner’s life after the business. That is an important discussion and may be a transition that needs to be planned for over a period of time. “Letting go” doesn’t come easy for some business owners. In fact, there are even tests now that can help determine how you will handle it when that time comes, and what to do about it. There is a consultant firm in Southern California, by the name of “Orange Kiwi” that specializes in that type of consulting. Determining how much you need to “walk away with”, involves analyzing how much you will need to live your life after the business and the goals you want to accomplish that require financial resources, and how much you have accumulated outside of the business. This will determine the dollar amount that you will need to walk away with, from the business. This is then compared to the preliminary valuation which reveals the “gap”. For instance, if you need to walk away with $3 – $5 million net after expenses and taxes, and your business is currently worth approximately $2 million, then the “gap” is $1 million to $3 million.

This leads us to performing a “preliminary valuation”, which is an informal valuation and costs a fraction of a formal valuation. It is a necessary step in order to determine where you stand and how much of a financial gap exists. Finally, the last step in this phase, is forming your team of advisors. Exit planning is a team sport, and you need the right people/advisors on your team – Professionals who are experienced and who are willing to work together. The diagram below shows a number of potential advisors, an owner may need a few of them or many of them at different times.


 

The “Plan Development” phase includes the gathering of data, the development of a draft plan, the development of a final draft plan, and establishing a plan of action which includes setting time tables, delegating tasks to advisors, and so forth. When we gather data, there are many areas to gather from. This includes the financials, performing a 5-year cash flow analysis, a 5-year cash flow projection and a host of other metrics, client base analysis, re- occurring income, etc. The draft plan is a starting point of a plan. It is reviewed by all of the participating advisors, which may include the C.P.A., the business broker or investment banker, the out-sourced C.F.O., estate planning attorney, tax attorney or business attorney, and so on. Depending on your particular situation, some or many of these advisors may be included.

The “Implementation phase” of the planning process includes “managing the action steps”, and revising the plan as needed, performing a formal business valuation (one that holds up in the negotiation of the sale), positioning the company for sale or inside transition, and the liquidity event, or the actual sale.

Managing the action steps is critical, because plan execution is critical. It’s one thing to develop a plan, but implementing it properly is crucial in a successful outcome. The exit planning professional can help an owner with that, so that he or she does not get consumed by it and can continue to work on the business. Performing a final valuation is required, which is a solid valuation to include in the sale of the company and also for tax purposes. Positioning the company for sale is where a business broker or a merger & acquisition professional comes in. They are the ones who will position the company for sale, put the company to market, and help to finalize a sale. It’s better if they are included earlier on.

It is also where the implementation of structuring the company ownership comes in. Meaning, what is the best way to position the ownership of the company to achieve the most tax efficient transaction. For instance, utilizing special trusts that avoid state taxes upon the sale of the company. But, that is for a future discussion.

Then comes the liquidity event or the actual sale of the business. It often doesn’t come easy and negotiating with a third party can be grueling and time consuming. But the better you have planned and prepared, the better the outcomes will most likely be.

My intention of this article is to point out a few things: One, the best way to develop an exit plan is by applying a process. Two, exit planning takes time. Three, exit planning is a team sport and requires the careful selection of advisors. And four, exit planning is a serious subject and requires a thorough discussion – more than a discussion with your local C.P.A., although a C.P.A. is a critical advisor in the exit planning process.

Steven Zeller is a Certified Business Exit Planner, Certified Financial Planner, Accredited Investment Fiduciary, and Co-Founder and President of Zeller Kern Wealth Advisors. He advises business owners with developing exit plans, increasing business value, employee retention, executive bonus plans, etc. He can be reached at szeller@zellerkern.com