The One-Way Buy-Sell Agreement: An Often-Overlooked Strategy for Business Owners

Thomas J. Perrone, CLU, CIC

A Different Way to Protect a Business, Its Key People and the Owner’s Future

Business owners spend a great deal of time thinking about how to grow their companies. They hire employees, develop customers, build vendor relationships and continually look for ways to increase profitability.

But there is another question that deserves just as much attention:

What happens to the business if a key owner or key person dies unexpectedly?

A traditional buy-sell agreement can provide an answer when there are multiple owners. But there are situations where a different approach may be more appropriate—particularly when the objective is to create a mechanism for the company to purchase an owner’s or key person’s interest upon death.

One strategy discussed in this podcast is the one-way buy-sell agreement.

The concept can provide a business with a predetermined method for handling an ownership interest when an unexpected death occurs, while also potentially creating financial security for the business and the surviving family.

What Is a One-Way Buy-Sell Agreement?

A one-way buy-sell arrangement is essentially an agreement in which one party agrees to purchase an ownership interest from another party upon a specified triggering event, most commonly death.

The arrangement can be particularly interesting when a company has an important owner or key person whose continued involvement is critical to the business.

Instead of leaving the family, the business and the remaining owners to negotiate what happens after a death, the agreement establishes a process in advance.

That can provide something every business owner needs:

certainty.

The goal is not simply to create a legal document. The objective is to establish a coordinated strategy for:

  • Protecting the business

  • Providing liquidity

  • Creating a method for transferring ownership

  • Helping the deceased owner’s family receive value

  • Retaining important employees or key people

  • Avoiding a forced or poorly timed sale

  • Providing continuity for customers, vendors and employees

Why Key People Matter So Much

The podcast discussion begins with a real-world situation involving a company and a particularly valuable key person.

The individual was considered extremely reliable and important to the organization. The company initially considered an executive-benefit arrangement as a way of retaining that person.

That raises an important point:

Key-person planning and business-transition planning are often connected.

A business may have an employee or owner whose knowledge, relationships, production ability or leadership makes that individual extremely difficult to replace.

If that person dies unexpectedly, the financial consequences can extend well beyond the person’s salary.

The company could lose:

  • Customers

  • Revenue

  • Specialized knowledge

  • Leadership

  • Vendor relationships

  • Employees

  • Business value

That is why business owners should think about both retention and transition when evaluating their most important people.

The Connection Between Executive Benefits and a One-Way Buy-Sell

One of the interesting aspects of the strategy discussed in the podcast is the relationship between executive benefits and a one-way buy-sell arrangement.

An executive-benefit strategy may be used to help attract and retain an important employee.

But when the planning is coordinated with ownership and transition objectives, the same overall strategy can potentially address additional business concerns.

The key is to avoid looking at each financial strategy as an isolated transaction.

Instead, business owners should ask:

How does this strategy fit into the overall plan for the company?

A business may need to simultaneously:

  1. Retain an important person.

  2. Protect the company from the economic consequences of that person’s death.

  3. Provide an orderly transition of an ownership interest.

  4. Create liquidity for the person’s family.

  5. Maintain control of the business.

  6. Continue building business value.

A properly designed arrangement can bring these objectives together.

What Happens When an Owner Dies?

Without a plan, the death of an owner can create a difficult situation.

The deceased owner’s family may suddenly own an interest in a business they know little about.

The remaining owners may want to continue operating the company but may not have the cash to purchase the family’s interest.

The family may need liquidity.

The business may need time.

And everyone may have different ideas about what the ownership interest is worth.

That is a recipe for conflict.

A one-way buy-sell arrangement can establish the basic framework before the crisis occurs.

Rather than asking, “What do we do now?”, the parties have already determined what is supposed to happen.

Funding Is Just as Important as the Agreement

One of the most important lessons for business owners is that having a buy-sell agreement is not necessarily the same thing as having a funded buy-sell agreement.

An agreement can establish an obligation to purchase an ownership interest.

But where does the money come from?

This is where life insurance and other funding mechanisms may become important.

The podcast discusses arrangements involving life insurance, premiums, cash value and other planning considerations.

The basic concept is straightforward:

The funding should be designed at the same time as the agreement—not years afterward.

Otherwise, a business could have a perfectly drafted agreement but discover that it does not have the financial resources to carry out the transaction when the triggering event occurs.

The Family Has an Interest Too

Business owners sometimes focus almost entirely on what happens to the company.

But the owner’s family is also an important part of the equation.

Suppose an owner dies and leaves a substantial business interest to the family.

The family may now own an asset that is difficult to sell, difficult to value and difficult to manage.

The remaining owners, meanwhile, may need control of the business to continue operating it.

A properly structured buy-sell arrangement can potentially solve both problems.

The family receives value for the ownership interest.

The remaining owners or the business receive the ownership interest.

The company can continue operating.

That is the fundamental objective of transition planning:

Turn a potentially disruptive event into an orderly transaction.

The Importance of Starting Before There Is a Crisis

One of the recurring themes in business planning is that the best time to solve a problem is before it becomes a problem.

A death, disability, retirement or other unexpected event is not the time to begin discussing ownership.

The parties should already understand:

  • Who buys?

  • Who sells?

  • What triggers the transaction?

  • How is the value determined?

  • How will the purchase be funded?

  • What happens to the family?

  • What happens to the business?

  • What happens to the remaining owners?

  • How will the arrangement be reviewed as the company grows?

These questions should be addressed while everyone is healthy, the relationships are good and the business is operating normally.

Business Value Changes Over Time

Another reason these arrangements need to be reviewed is that businesses change.

A company that is worth $2 million today might be worth considerably more several years from now.

Key employees change.

Ownership changes.

Debt changes.

The company’s cash flow changes.

The owner’s personal objectives change.

The insurance funding may change.

Therefore, a buy-sell agreement should not be treated as a document that is created once and placed in a drawer.

It needs to evolve with the business.

The Bigger Lesson for Business Owners

The one-way buy-sell concept illustrates a much larger principle:

Business planning should be integrated.

Growth planning, key-person planning, executive benefits, protection planning, retirement planning and transition planning should not necessarily be viewed as separate subjects.

They can be different pieces of the same business-planning puzzle.

A successful business owner needs to build value.

But building value is only one part of the equation.

The owner also needs to protect that value and eventually determine how that value will be converted into personal financial security.

That is why transition planning should begin long before retirement.

Questions Every Business Owner Should Ask

If you own a closely held business, consider asking yourself:

  1. What happens to my company if I die tomorrow?

  2. Who would purchase my ownership interest?

  3. Does my family know what would happen?

  4. Is there a written buy-sell agreement?

  5. Is the agreement properly funded?

  6. Has the value of the company been updated?

  7. Would the business have enough liquidity to complete the purchase?

  8. What happens to our key people if they die?

  9. Could the loss of a key person significantly reduce business value?

  10. Does our current plan coordinate business protection with ownership transition?

If you cannot answer these questions clearly, your business may have a transition-planning gap.

Conclusion

A one-way buy-sell agreement is not simply a legal document. It can be part of a broader strategy for protecting a business, providing liquidity, retaining key people and creating an orderly transfer of ownership.

The most important point is that the agreement and the funding need to work together.

Business owners work for years to create valuable companies. The next step is making certain that an unexpected event does not destroy the value they worked so hard to create.

The objective should be simple:

Build the value. Protect the value. And have a plan to transition the value.

That is what effective business transition planning is designed to accomplish.

About the Podcast

This topic was discussed on Building and Protecting Your Business Worth, hosted by Thomas J. Perrone, CLU, CIC, of New England Consulting Group, Inc. The podcast focuses on strategies and ideas designed to help business owners build, protect and transition their businesses while creating greater financial security for their future.

tperrone@necgginc.com

Website: 

Comprehensive Business Planning Guide

click to download your free “Comprehensive Business Planning Guide”

INTERNAL VS. EXTERNAL SALES

BY; Thomas J. Perrone, CLU,CIC 

Choosing the Right Path to Exit Your Business

A Business Owner’s Guide from the GWT Planning System®

Every business owner will exit their company one way or another — the only real questions are when, on what terms, and to whom. Of all the decisions in a transition plan, few shape the outcome more than the choice between an internal sale and an external sale. Each path carries distinct implications for valuation, timeline, taxes, financing, and the legacy you leave behind. This report walks through both paths so you can weigh them clearly, in the context of your own Growth, Wealth, and Transition goals.

What Is an Internal Sale?

An internal sale transfers ownership to people already inside the business — a family member, one or more key managers, a broader group of employees through an Employee Stock Ownership Plan (ESOP), or some combination of these. The buyer already knows the company’s operations, culture, and customers.

Common Internal Sale Structures

  • Family succession — passing the business to a child or other relative, often paired with an estate plan and a multi-year transition of leadership.
  • Management buyout (MBO) — one or more key employees purchase the company, frequently financed in part by the seller.
  • Employee Stock Ownership Plan (ESOP) — a qualified retirement plan purchases company stock on behalf of employees, offering the seller potential tax advantages and a built-in buyer.
  • Partner or co-owner buyout — an existing partner buys out a retiring or exiting owner’s interest, often under a pre-existing buy-sell agreement.

What Is an External Sale?

An external sale transfers the business to a buyer outside the company — a strategic buyer (often a competitor or company in an adjacent market seeking synergies), a financial buyer such as a private equity firm, or an individual entrepreneur buying their way into ownership.

Common External Sale Structures

  • Strategic acquisition — a buyer in your industry purchases the business for its customers, talent, technology, or market position, often paying a premium for synergy.
  • Financial buyer / private equity — an investment group acquires the business primarily for its cash flow and growth potential, typically with a plan to scale or resell it later.
  • Individual or search-fund buyer — an entrepreneur purchases the business to run it directly, often using SBA or other acquisition financing.

Key Differences at a Glance

Factor Internal Sale External Sale
Typical buyer Family member, key manager(s), or employees (via ESOP) Strategic buyer, competitor, or private equity/financial buyer
Valuation & price Often below full fair market value; frequently seller-financed Usually the highest achievable price, especially with strategic/synergy buyers
Timeline to close Can be structured over years (gradual transition) Often 6–12 months once a deal is in motion
Confidentiality High — deal stays inside the company Lower — due diligence exposes financials to outside parties
Financing Seller financing, SBA loans, or ESOP debt are common Buyer typically arranges its own financing or uses cash/PE capital
Cash at closing Partial upfront, balance paid over time Larger lump sum at closing is more common
Legacy & culture Preserves culture, brand, and relationships with staff/clients May result in integration, rebranding, or workforce changes
Owner’s post-sale role Often a gradual, mentoring exit Usually a clean, faster exit (sometimes with an earn-out)
Risk to seller Buyer’s ability to repay over time is a real risk Deal risk is concentrated in due diligence and negotiation, then resolved at close
Tax treatment Can sometimes be structured favorably (e.g., installment sale, ESOP rollover) Structure depends on asset vs. stock sale; often subject to negotiation

Weighing the Trade-Offs

Why Owners Choose an Internal Sale

  • Preserve the company culture, brand, and relationships built over decades
  • Reward and retain loyal employees or family members who helped build the business
  • Maintain a gradual, mentoring transition rather than a sudden exit
  • Keep the sale confidential, without exposing financials to outside parties

Why Owners Choose an External Sale

  • Maximize sale price, particularly when a strategic buyer will pay for synergy
  • Receive more cash at closing rather than relying on a buyer’s future payments
  • Achieve a cleaner, faster exit with less ongoing financial or operational risk
  • Access buyers who bring capital, infrastructure, or expertise to grow the business further
A Note on Value

An internal sale and an external sale rarely produce the same number on the closing statement. Internal buyers are usually financing the purchase from the business’s own future cash flow, which caps what they can pay; external buyers — especially strategic buyers — can sometimes pay for value the internal team cannot. Knowing your business’s true worth, and the gap between internal and external value, is the starting point for choosing a path with confidence.

Questions to Guide Your Decision

  • How important is it that the business stay in the family or under existing leadership?
  • Do you need maximum cash at closing, or can you accept a phased payout over time?
  • Is there a capable internal buyer — and can they realistically finance the purchase?
  • How much risk are you willing to carry if you finance part of the sale yourself?
  • What matters more to you: the highest possible price, or the legacy of who runs the business next?
  • How much time do you have before you need or want to exit?

Bringing It Together with the GWT Planning System®

Deciding between an internal and external sale isn’t a decision to make in isolation — it’s one piece of a broader Growth, Wealth, and Transition plan. The right path depends on where your business stands today, what your personal and financial goals require, and how much runway you have to prepare. A well-built transition plan builds real, transferable value into the business long before a specific buyer — internal or external — is identified, so that whichever path you choose, you are negotiating from strength rather than necessity.

If you’re weighing your own exit options, the most valuable next step is an honest assessment of where your business stands today against both paths — so the choice is one you make deliberately, not one that gets made for you.

1.FREE- GWT PLANNING SYSTEM® DOWNLOAD

2.FIND OUT MORE ABOUT US

3 Let have a conversation

4 ARTICLE THE ONEWAY BUY AND SELL AGREEMENT

Why 75% of Businesses Fail in 10 Years (And How to Fix It)

By Thomas J. Perrone, CLU, CIC

Your Business May Have a Plan. But Does It Have a Plan for the Details?

After more than 53 years working with business owners, I have noticed a recurring problem:

Business owners are often unaware of the things they don’t know.

And that lack of awareness can be expensive.

Most business owners are very good at running their businesses. They know their customers, their products, their employees, and their markets. They know how to generate revenue and solve the problems that show up every day.

But there is another side of business ownership that often gets overlooked—the planning that takes place behind the scenes.

I call this the Plan for Details.

It is the planning that addresses how you will grow the business, protect what you have built, create wealth from the business, and eventually transition out of the business.

It is different from the action plan that gets you into business and keeps the cash flow moving.

And that difference can have a tremendous impact on the ultimate value of your business.

Three Levels of Awareness

I believe there are three different levels of awareness among business owners.

1. You know there is a problem—but you tolerate it.

You recognize that something isn’t working perfectly, but because the business is still operating, you don’t address it.

“It’s working well enough” becomes the answer.

2. You discover a problem and fix it.

You weren’t aware of the issue, but once someone points it out, you understand it and take action.

This type of awareness can prevent financial leakage and help improve the business.

3. You don’t know what you don’t know.

This is the most dangerous situation.

You don’t know that an opportunity exists. You don’t know that a risk exists. You don’t know that something is costing you money.

And because you don’t know about it, nothing changes.

This is one of the biggest challenges facing business owners today.

There are opportunities to increase business value, protect the company, improve cash flow, retain key employees, create wealth outside the business, and prepare for a future transition—but many owners simply aren’t aware that these opportunities exist.

The Business Owner’s Action Plan vs. the Plan for Details

When most people start a business, their attention naturally goes toward the Action Plan.

They want to get their product or service to market.

They want customers.

They want revenue.

They want cash flow.

They want the business to grow.

And that’s exactly where an entrepreneur should be focused in the beginning.

The Action Plan is exciting. It’s where the energy is.

But the part that often gets avoided is the Plan for Details.

The Plan for Details addresses four critical areas:

  • Growth

  • Protection

  • Equity creation and distribution

  • Exit and transition

These are the areas that can determine whether a business simply produces an income—or ultimately creates substantial wealth for its owner.

What Happens Without a Plan for Details?

Without this type of planning, business owners can find themselves facing problems they never anticipated.

They may:

  • Lose key employees.

  • Lose customers or valuable relationships.

  • Face lawsuits or other unexpected risks.

  • Have no plan if the owner dies or becomes disabled.

  • Experience significant financial consequences when an owner dies.

  • Lose money unnecessarily through inefficient tax planning.

  • Fail to build wealth outside the business.

  • Struggle to create a strong company culture.

  • Have difficulty attracting and retaining talented employees.

  • Miss opportunities for innovation.

  • Discover too late that their business isn’t attractive to a buyer.

None of these problems necessarily mean the owner did a poor job running the business.

They may simply mean that the owner never had a comprehensive Plan for Details.

Building Business Value Is More Than Increasing Revenue

One of the most important concepts in business planning is understanding value drivers.

Value drivers are the characteristics of a business that make it attractive to a prospective buyer.

A buyer doesn’t simply look at what the business makes today.

The buyer wants to know:

Will this business continue to produce cash flow after I buy it?

That leads to questions about:

  • Growth potential

  • Cash flow

  • Key employees

  • Management depth

  • Systems and processes

  • Customer relationships

  • Company culture

  • Dependence on the owner

  • Opportunities for future growth

A business with strong systems, capable employees, good cash flow, and growth potential is generally much more attractive to a buyer than a business that depends almost entirely on its owner.

That’s why planning for a transition shouldn’t begin when you’re ready to sell.

It should begin years—even decades—before you leave.

What If You Died Tonight?

Here’s a question every business owner should ask:

What would happen to your business if you died tonight?

Or what happens if you become disabled?

What happens to your employees?

What happens to your customers?

What happens to your bank financing?

What happens to your family?

What happens to the value you’ve spent years building?

For example, the loss of an owner or key person can have an immediate impact on a company’s financial stability and operations.

And a key employee who leaves may take valuable relationships, knowledge, employees, and even trade secrets with them.

The solution isn’t simply to hope they stay.

The business needs a strategy for retaining the people who are critical to its success.

Key Employees Are Part of Your Business Value

A strong company doesn’t depend entirely on the owner.

The goal should be to develop people who can think and act like owners.

When you accomplish that, several things happen.

You create stronger management.

You create greater freedom for the owner.

You create more time for family and other priorities.

You improve cash flow.

You create a business that can operate without the owner being involved in every decision.

And you make the business more attractive to a future buyer.

A buyer wants to purchase a business—not purchase a job.

If the owner walks out the door and the business falls apart, the business becomes much harder to sell.

Culture Is a Business Asset

Another often-overlooked component of business value is company culture.

A strong culture can make recruiting easier because people want to work for companies where they feel valued and where they can see a future.

Culture can also improve retention.

And when good people stay, they accumulate knowledge, build relationships, develop systems, and become increasingly valuable to the organization.

The result is a stronger business.

Creating Wealth Outside the Business

Many business owners spend decades building wealth inside their company.

The problem is that their business may represent the overwhelming majority of their net worth.

That creates concentration risk.

It also creates a problem when the owner eventually wants to retire.

The question becomes:

How do you convert business success into personal wealth?

This is where careful planning can be particularly important.

The business may be capable of generating cash flow that can be used strategically to create wealth outside the company while continuing to grow and operate the business.

The objective isn’t simply to accumulate money.

The objective is to create a business that produces cash flow, builds equity, and ultimately allows the owner to convert business value into financial independence.

Why Traditional Planning Often Doesn’t Work for Business Owners

One reason business owners don’t have a Plan for Details is that traditional planning can become unnecessarily complicated.

Business owners are busy.

They don’t want a planning process that takes months and requires endless meetings.

They want to understand the issues, make decisions, and move forward.

Another problem is that different advisors often work independently.

The business owner may have a CPA, attorney, financial advisor, insurance professional, and business consultant—but nobody is bringing the pieces together.

In my experience, the best planning occurs when the appropriate advisors work together.

Your CPA understands the tax issues.

Your attorney understands the legal issues.

Your financial advisor understands investments and financial strategies.

Your business consultant understands the business.

Put the right people around the same table and you can begin solving the actual problems of the business rather than simply selling products.

The Four Areas of the GWT Business Planning System

The GWT Business Planning System focuses on four fundamental areas.

1. Growth

How can you increase the value of the business?

What systems, people, processes, and strategies can help the company grow?

2. Protection

What happens if something goes wrong?

What if the owner dies?

What if the owner becomes disabled?

What if a key employee leaves?

What if the company is sued?

What if cash flow suddenly becomes a problem?

Protection planning is about preparing for the “what ifs.”

3. Equity Creation and Distribution

How can the business create wealth for its owner?

And just as importantly, how can some of that wealth eventually be distributed outside the business?

The goal is to use the business strategically—not simply as a source of income, but as a vehicle for creating wealth.

4. Exit and Transition

Eventually, every business owner has to answer one question:

What happens to the business when you’re no longer running it?

That doesn’t necessarily mean selling tomorrow.

Transition could be 10, 20, or even 30 years away.

But the decisions you make today can have a tremendous impact on the options available to you later.

The GWT 30-Day Business Planning Pathway

The GWT Business Planning System was designed around a simple idea:

Business planning doesn’t have to consume your life.

The process uses a series of approximately 15–16 planning blueprints that help identify the areas that deserve attention.

You don’t necessarily need all of them.

You identify the areas that are most relevant to your business, prioritize them, and then work on them one at a time.

The process is designed to take approximately 2–4 hours of the business owner’s time over a 30-day period.

It includes short educational videos, forms, discussions, and planning sessions.

The goal isn’t to overwhelm you with information.

The goal is to help you become aware of what you don’t know, identify the areas that need attention, and establish a practical path forward.

The Real Goal Isn’t a Bigger Binder

Business planning shouldn’t be about creating a complicated document that sits on a shelf.

It should create action.

A good Plan for Details should help you:

  • Build business value.

  • Protect the value you’ve created.

  • Improve cash flow.

  • Develop key employees.

  • Build management depth.

  • Create a stronger company culture.

  • Reduce dependence on the owner.

  • Create wealth outside the business.

  • Prepare for unexpected events.

  • Increase the likelihood of a successful transition.

Ultimately, it should give the owner something that is often just as valuable as money:

freedom.

Freedom to spend more time with family.

Freedom to take time away from the business.

Freedom to make decisions based on opportunity rather than necessity.

And eventually, freedom to leave the business on your terms.

Your Business Needs More Than an Action Plan

The Action Plan gets the business moving.

The Plan for Details determines what happens after it starts moving.

If you are a business owner, ask yourself:

Do I know exactly what would happen to my business if I died, became disabled, or lost a key employee?

Do I have a plan for building value?

Do I know how I will eventually get my wealth out of the business?

Could my business operate successfully without me?

Would someone want to buy my business today?

If you don’t know the answers, that’s not necessarily a problem.

It may simply mean you’ve discovered something you weren’t aware of.

And that’s where good planning begins.

The Bottom Line

Most business owners don’t have a business planning problem because they don’t care.

They have one because they’re busy running the business.

The Plan for Details is designed to help close that gap.

It gives you a way to step back from the day-to-day operation of the company and look at the bigger picture—growth, protection, equity creation, and transition.

The earlier you begin, the more options you have.

And the objective isn’t simply to build a bigger business.

It’s to build a business that creates wealth, protects that wealth, and ultimately gives you the freedom to decide what happens next.

Lets Discuss: Toms Calendar

Free Download; The Planning GWT PLANNING SYSTEM® Guide

Article: Where you are- Where you Could Be

Tperrone@necgginc.com

If you would like to learn more about the GWT Business Planning System and the 30-Day Business Planning Pathway, contact Thomas J. Perrone, CLU, CIC at 203-530-6615.

Where You Are – Where You Could Be!

Why an Annual Review Is the Most Overlooked Step in Business Owner Planning

By Thomas J. Perrone, CLU, CIC | Founder, New England Consulting Group of Guilford, Inc.

Ask most business owners how their planning is doing, and they’ll tell you it’s fine. They’ll say it with confidence, too — the same way most of us would say we feel healthy on any given day. But ask that question in the middle of a CT scan, and the confidence tends to disappear. The difference isn’t your health. It’s what you can’t see.

Business owner planning works the same way. The plans you built years ago may have looked airtight the day you signed them. But time passes, tax law changes, your business changes, and your family’s needs change — and none of that shows up on the surface. The documents still sit in the drawer looking just as official as they did the day you filed them. What they don’t tell you is whether they still fit.

We get the documents completed and executed, feel good about it, and then one morning realize it’s been five years — or more — since anyone looked at them again.

A Familiar Story

This pattern shows up constantly — with my clients, and with the professional colleagues I work alongside every day. The planning gets done. Everyone feels the relief of finally having “taken care of it.” Then life takes over, and the plan quietly ages in place while the world around it keeps moving.

The real risk isn’t skipping the planning altogether — most owners eventually get that part done. The risk is discovering, years later, that Washington has rewritten the rules, your business has grown or changed shape, your family situation is different, and no one ever flagged it. If any of those shifts would have changed your strategy, the only real question worth asking is: when would you have wanted to know?

Building the Fix Into the System

This is exactly the problem I built the GWT Planning System® to solve. GWT stands for Growth, Wealth, and Transition — the three areas every business owner’s planning needs to work together, not in isolation. But good structure alone isn’t enough. A plan that’s well designed on day one and never revisited is still a plan that goes stale.

So, from the very beginning, the GWT Planning System® was built with an automatic annual review woven directly into it — not an optional add-on, but part of how the system runs. Every year, that review happens. Sometimes it’s in person. Sometimes it’s a phone call. Sometimes it’s a Zoom conversation. The format isn’t the point. The consistency is.

That built-in review does three things for every client:

  • It catches tax and legal changes coming out of Washington before they quietly undermine a strategy that used to work.
  • It keeps the plan aligned with the business itself, which rarely looks the same from one year to the next — revenue, staffing, ownership, and value all shift.
  • It accounts for changes at home — a marriage, a health event, a child’s changing role in the business, a shift in retirement timing.

The Most Critical Part of Planning

Over more than fifty years of doing this work, I’ve come to see this as the most important part of what I do — not just putting the right plan in motion but making sure it stays right as everything around it keeps changing. A plan is not a document you finish once. a relationship you maintain.

If you can’t remember the last time your plan was reviewed against today’s tax law, today’s business, and today’s family circumstances, that’s worth changing before it becomes a costly surprise. The goal isn’t to redo the planning every year — it’s to know, every year, exactly where you stand and where you could be.

The goal isn’t to redo the planning every year — it’s to know, every year, exactly where you stand and where you could be.

If it’s been a while since your plan had a real second look, let’s put one on the calendar.

tperrone@necgginc.com

Questions? Call me.  My Calendar

Download Your Free GWT Report- Learn how the GWT Planning System® can be your pathway to solid up to date planning and help you with decisions for the future:  Click

Are you Building your Business by Design…or by luck?

The Insurance-Holding LLC: A Smarter Way to Fund Your Buy-Sell Agreement

 

By Thomas J. Perrone, CLU, CIC

Every multi-owner business eventually asks the same uncomfortable question: what happens if one of us dies, becomes disabled, or wants out? A buy-sell agreement answers the “what” — it’s the legal contract that says the remaining owners (or the business) will buy out a departing owner’s interest. But a buy-sell agreement is only as good as its funding mechanism. Promises to pay are worthless if the cash isn’t there when it’s needed.

Life insurance is the most common way to fund a buy-sell agreement, because it delivers cash exactly when it’s needed most — at death. The harder question is *who should own the policies*. For businesses with more than two or three owners, a growing number of advisors are turning to a special-purpose LLC created solely to hold those policies. Here’s how it works, and why it might be the cleanest solution on the table.

The Problem With the Traditional Options

There are two classic ways to structure buy-sell funding:

Cross-purchase agreements** have each owner personally buy a policy on every other owner. This works fine with two owners (two policies), but the math explodes quickly. Four owners need twelve policies. Six owners need thirty. Every time an owner joins or leaves, policies have to be rewritten. It’s an administrative nightmare, and it often means owners of different ages and health statuses paying wildly different premiums for equal buyout rights.

Entity-purchase (redemption) agreements** solve the multiple-policy problem — the company itself owns one policy per owner — but they create a different issue: when the company redeems a deceased owner’s shares, the surviving owners don’t get a step-up in the cost basis of their own interests. That can mean a much bigger capital gains tax bill down the road when they eventually sell

The LLC Solution

An insurance-holding LLC splits the difference. The owners form a separate LLC — sometimes called a “special-purpose entity” or “insurance LLC” — whose only job is to own and administer life insurance policies on each business owner. The LLC is typically structured as a partnership for tax purposes, with each business owner holding a membership interest proportional to their stake in the operating company.

Here’s the flow:

– The LLC purchases one policy on each owner’s life (not one per pairing, so the policy count stays low no matter how many owners there are).

– Each owner (or the operating business) contributes cash to the LLC to cover premiums.

– When an owner dies, the LLC receives the death benefit tax-free.

– The LLC uses those proceeds to purchase the deceased owner’s interest in the operating business, distributing it to the surviving members according to the buy-sell terms.

Because the LLC — not the individual owners — is treated as the policy owner and beneficiary, and because it’s taxed as a partnership, the surviving owners generally receive a basis step-up in their LLC interests similar to what a cross-purchase arrangement provides, while avoiding the multiple-policy headache of a true cross-purchase.

Why Owners Like It

Fewer policies, less administration. One policy per owner, held in a single entity, instead of a tangle of cross-owned contracts.

– Basis step-up preserved. Surviving owners’ tax basis generally increases, which can meaningfully reduce future capital gains taxes.

Avoids the transfer-for-value trap. Because all owners are members of the same LLC from the outset, properly structured transfers among them typically fall within IRS exceptions that keep the death benefit income-tax-free.

Built-in flexibility. New owners can be added as LLC members without rewriting a web of cross-purchase contracts.

Creditor separation. Holding policies in a distinct entity can offer a layer of separation from the operating company’s business risks.

What to Watch Out For

This structure isn’t a free lunch. It adds a second legal entity to maintain — its own operating agreement, its own tax filings, its own bank account for premium payments. The IRS has scrutinized partnership-owned life insurance arrangements in the past, so the LLC operating agreement needs to be drafted carefully, with real economic substance and clear treatment of premium contributions as capital contributions rather than disguised gifts. It also requires everyone to stay disciplined about funding premiums on time, since a lapsed policy defeats the entire purpose of the plan.

Is It Right for Your Business?

The insurance-holding LLC tends to make the most sense once you have three or more owners, where cross-purchase becomes unwieldy but the tax advantages over a straight entity redemption still matter. For two-owner businesses, a simple cross-purchase or entity-purchase plan may be all you need.

As with any buy-sell funding decision, this isn’t something to set up from a blog post. Work with a business attorney and a tax advisor who can model the specific numbers for your ownership structure, confirm the entity is respected for tax purposes, and make sure the policies, the operating agreement, and the buy-sell agreement itself are all pulling in the same direction. Get it right once, and it’s one less thing your partners have to worry about when the unexpected happens.

This article is for general informational purposes only and does not constitute legal, tax, or financial advice. Consult a qualified attorney and tax professional before implementing any buy-sell funding strategy.

 

Discussion: :My Calendar

Website: www.bpbpgrp.com/tom

203.530.6615

tperrone@necgginc.com

Check out this : Cheapest Way To Fund Your Buy and Sell Agreement

FREE DOWNLOAD CLICK HERE: THE BSA GUIDE

 

What to Do When Your Business Partner Wants Out (50/50)

By Thomas J. Perrone, CLU,CIC

You and your partner own a business fifty-fifty. You’ve been in it together for years. It’s going well. And then one day he sits you down and says, “I’m done. I want out.”

Now what?

You can’t fire him — he owns half. You can’t ignore him — he’s still a decision-maker. And if the two of you disagree about what the company is worth, you’re deadlocked. Nothing gets done. Clients feel it. Employees feel it. The business starts bleeding.

Without a plan for this moment, here’s what usually happens next: a long, expensive fight. A court deciding your company’s future. Or a fire sale to a stranger who doesn’t care what you built. None of those outcomes are good — and every single one of them is avoidable.

 Why 50/50 Partnerships Deadlock So Easily

If you’re in a fifty-fifty partnership, or thinking about forming one, it’s worth understanding why this structure is so dangerous — because it sounds so fair.

Fifty-fifty. Equal partners. Equal say. What could be wrong with that?

Here’s the problem: a fifty-fifty split is a partnership with no tiebreaker. On any big decision, you have exactly two votes — one for, one against. When they cancel out, nothing moves.

Day-to-day, that works fine. You split the work, the profit, the decisions. But the moment a partner wants out, that equal split becomes a weapon. He’s not just a co-owner anymore — he’s a veto.

And here’s the uncomfortable truth: most buy-sell and partnership agreements don’t handle this well. They name a price. They name terms. But they never answer the question that actually breaks deals — what happens when one of you wants to leave and you can’t agree on the number?

Step 1: Valuing the Departing Partner’s Share

The first thing that goes wrong is the valuation.

Say the business does $4 million in revenue and generates about $400,000 a year in profit. Your partner says, “I’m out. I want my fair share.” Fair share of what? He’s not asking for $400,000 — he’s asking for the value of his half of the *company*. And that number depends entirely on how you value it.

Your accountant might say the business is worth one times earnings — $400,000. Your partner brings in his own appraiser, who says it’s worth five times earnings — $2 million. Because if he’s selling, he wants the highest number. If you’re buying, you want the lowest. Neither of you is wrong. You’re just on opposite sides of the same coin.

Now you’ve got two appraisals a million-plus dollars apart, and an agreement that just says “fair market value.” But fair market value is a phrase that starts lawsuits, not a number that settles them.

This is the first reason deadlocks happen — not because the business isn’t valuable, but because nobody locked in *how* it would be valued before the exit. That’s not a math problem. That’s a planning problem. And it’s fixable.

Step 2: The Money Problem

Say you get past the valuation. You and your partner agree the business is worth $4 million. His half is $2 million. Great. Now the real question: where does two million dollars come from?

“I want out” and “here’s your money” are two very different sentences. This is where most buy-sells actually fall apart — not in the courtroom, but in the bank.

Pay him over time?Two million dollars over ten years is over $200,000 a year — out of a business generating $400,000. That’s half your profit, gone, for a decade. That’s not a buyout. That’s a slow bleed.

**Borrow it?** The bank will lend, but now the business is collateral, you’re on personal guarantees, and you’re paying interest on top. On $2 million financed over ten years, that’s hundreds of thousands of dollars in interest — money that leaves your company for good.

**Fund it in advance with life insurance.** A policy on your partner’s life, owned correctly, so the money arrives when you need it — a structured payout that doesn’t starve the business. This is the funding question almost nobody covers, and it’s the difference between a clean exit and a collapse.

So now we get to the tool that actually solves this: the shotgun clause.

Some call it a “buy-sell” clause or a “put-call” arrangement, but the shotgun is what breaks a deadlock fast. Here’s how it works: either partner can name a price for the whole business — say, $4 million. The other partner then has a choice. Buy the departing partner’s half at that price, or sell their own half at that same price.

Watch what that does. It’s elegant. If your partner says, “I’ll sell my half for $2 million,” you decide — buy at $2 million, or sell your half for $2 million. Your partner has to be honest about the number, because if he names a price too low, you might just buy his half at that bargain. If he names it too high, he might end up buying yours at that premium.

The shotgun makes both sides name a fair number, because neither of you knows which side of the deal you’ll end up on. It’s the closest thing to self-enforcing fairness in a business partnership.

A word of caution, though: the shotgun isn’t for every situation. It works best when both partners actually have the ability to buy — meaning the money’s available. And it needs to be drafted by someone who understands the tax consequences, because those consequences can follow your family for a generation.

But for a fifty-fifty deadlock, where neither side will budge and neither side will blink, the shotgun clause is the cleanest exit there is.

 The Mistake That Turns a Deadlock Into a Lawsuit

Here’s the mistake I see owners make over and over — the one that turns a fixable deadlock into a years-long lawsuit.

Most owners don’t put a buy-sell or shotgun clause in place until a partner actually wants out. By then, it’s too late.

Here’s what happens: a partner says “I want out.” There’s no clause. So now you’re negotiating a price between two people who are already in a fight. You don’t agree on the number. You don’t trust each other. And every day that passes, the relationship gets worse and the business bleeds more.

By the time someone suggests a shotgun clause, it’s already adversarial — and clauses drafted in the middle of a conflict are expensive and rarely end well.

The time to put the shotgun in place is the same day you sign the partnership agreement, when you’re both calm, fair-minded, and thinking clearly. That’s when you lock in the mechanism, so that when the exit happens — and it will happen — the tool is already there, and the only thing left to figure out is the number.

Your 3-Step Action Plan

Here’s what to do this week:

1. **Find your deadlock clause.** Pull out your partnership or buy-sell agreement. No shotgun or buy-sell mechanism? That’s red flag No. 1 — and it’s fixable today.

2. **Lock in a valuation formula.** Not “fair market value at the time.” A specific formula — a multiple of earnings you both agree on and update yearly.

3. **Have the conversation.** It’s awkward to talk about the day one of you leaves. But the deadlock, the lawsuit, and the fire sale are far more awkward.

Picture the owner who has to sell because his partnership broke down with no plan in place. That’s a fire sale waiting to happen. Don’t let that be your business.

Plan the exit before the exit plans you.

Download your free report: The Buy and Sell Agreement Checkoff Guide

Learn about our planning GWT Planning System® AND how it can help you design a solid Buy and Sell Agreement :  GWT Planning System®  

Want a discussion? For a free Consultation:  Tom’s Calendar 

Here is another article related to this one:

Blog Article: 

Seven Things Buyers May Pay More for When Purchasing a Business

You Built the Business. Now Let’s Make Sure It Pays You Back.

By: Thomas J. Perrone, CLU,CIC -New England Consulting Group of Guilford, Inc.

A planning system that helps business owners build value in their business,  stop overpaying taxes, stop losing wealth, and creates  business value and aa path so they can walk away from their business with their wealth, and on their own terms.

The Problem

Many business owners struggle to build personal wealth because business cash flow demands keep their money tied up. Our three-step process creates financial clarity, helps reduce wealth lost to taxes and uncertainty, and positions owners to walk away wealthy when it’s time to exit.”

Most business owners struggle with creating future wealth for their personal economic security because their businesses require so much of the financial resources and cash flow to continue to operate and grow the business.

You started with nothing but an idea and a willingness to outwork everyone else. Years later, youve built something real — payroll, customers, a name people trust.

But heres what nobody tells business owners: most of your wealth is trapped. Its tied up in a business thats hard to value, harder to sell, and taxed at every turn. Your retirement plan is a vague hope that someone, someday, will buy the company for what its worth.

Meanwhile, every year you wait:

  • You overpay taxes on money you’ve already earned
  • Inflation and poor structuring quietly erode what you’ve built
  • Your business becomes more dependent on you, not less — which makes it harder to sell or step back from

You didnt spend decades building this business just to hand the upside to the IRS, or to find out too late that no one wants to buy it.

You built it so you could walk away wealthy.

The Guide

Thats the problem I solve for with business owners — not as a generalist financial advisor, but as a specialist in one specific question:

How do you turn the value locked inside your business into wealth in your own hands?

I understand how hard you’ve worked—and how much of that effort has yet to become personal wealth. I learned this firsthand when my father died at 51 with nearly all his business value trapped inside the company. The company was ultimately sold for pennies on the dollar. The heartbreak my family endured motivated me to make sure other business owners would never have to experience a situation like ours.

A Three Step System to Extract the Wealth You’ve Built When You Need It the Most!

#1 GROW Find out what your business is worth AND if you are taking advantage of all the planning opportunities available to you. A three-minute survey, called the Business Owners Personal Viewpoint, gives us enough info to create a WHERE YOU ARE REPORT”. (A Barometer of your business).

We start with a clear-eyed look at your business value today, and whats driving — or hurting it. Also, what areas of your planning are effective and ineffective up to now!

#2 PROJECT WEALTH — Stop the leaks- and missed opportunities!

We find where you are overpaying in taxes and where your personal wealth is exposed — then fix it. “OUR DISCOVERY REPORT

#3 TRANSITION — Build your exit before you need it

We build the plan that lets you leave the business — by choice, not by crisis — with the money in your pocket, not just the memories. It is a plan by “Design” and not a plan by “Default”.

Resources:

Check out this video:  “Business Owners Getting This Wrong: A trapped Retirement plan. 

Get your Free Report: Building Wealth Through Your Business!

Want to discuss, use my calendar:  Toms Calendar  

 

 

Are You Building Your Business by Design… Or by Luck?

Are You Building Your Business by Design… or by Luck?

A Four-Pillar Framework for Turning Business Success into Lasting Personal Wealth

By Thomas J. Perrone, CLU, CIC | tperrone@necgginc.com

Executive Summary

Most small business owners don’t lack ambition — they work hard, grow steadily, and reinvest everything back into the company. Yet many reach a point where an uncomfortable question surfaces: is the business growing by design, or simply by default? While revenue climbs, critical areas such as financial planning, risk protection, tax efficiency, and long-term transition are frequently overlooked, not from a lack of care but from a lack of time, clarity, or structure.

This white paper summarizes a structured planning approach — often referred to as a “Destiny Plan” — that aligns a business with its owner’s ideal life and financial future. Rather than adding complexity, the framework organizes the essential drivers of long-term success and security into four pillars: Growth, Protection, Equity, and Transition.

The Hidden Gaps in Growing Businesses

Business owners are often aware, sometimes painfully so, that critical elements of their business are being neglected. Common gaps include:

  • No clear long-term growth strategy
  • Limited protection against unexpected events
  • Inefficient tax planning
  • No defined exit or succession plan
  • Uncertainty about how to convert business success into personal financial security

Left unaddressed, these gaps mean that even an outwardly successful business can remain financially fragile.

The Questions Every Business Owner Should Ask

A useful starting point is self-assessment. Consider the following:

  • Do you have a clear, fail-safe plan to grow, protect, and eventually transition your business?
  • If you had to step away tomorrow — due to retirement, disability, or worse — what would happen?
  • Could you extract your business value in the most tax-efficient way possible?
  • Are you maximizing your compensation and benefits through your business?
  • Do you have a plan for the unexpected — economic downturns, key employee loss, or sudden life events?

Difficulty answering any of these is a signal, not a source of alarm: it indicates that planning is overdue, and that the owner is far from alone in facing this gap.

The Four-Pillar Framework

What most business owners need isn’t more complexity — it’s clarity. A structured approach brings together the key elements that drive long-term success and security into one cohesive strategy, built on four essential pillars.

1. Growth: Building with Purpose

Growth should be intentional, not accidental.

  • Implementing systems that scale with the business
  • Developing strong leadership and teams
  • Focusing on the true drivers of business value

2. Protection: Preparing for the “What Ifs”

Every business faces risk. The question is whether you’re prepared.

  • What if a key employee leaves?
  • What if cash flow tightens?
  • What if you can’t continue running the business?

Proper protection planning ensures the business can withstand the unexpected.

3. Equity: Turning Success into Wealth

Your business is likely your largest asset — are you leveraging it effectively?

  • Accessing equity without unnecessary tax burdens
  • Structuring compensation to maximize benefits
  • Building wealth both inside and outside the business

The goal is not just to grow a business — it’s to create real, usable wealth.

4. Transition: Planning Your Exit Before You Need It

Every business owner will eventually leave their business. The only question is how.

  • Will it be on your terms?
  • Will you receive full value?
  • Is your family or team prepared?

A well-designed transition plan enables an exit that is smooth, efficient, and profitable — whether through sale, succession, or retirement.

A Simple First Step

Owners don’t need to solve everything today — but they do need to start. Even a quick self-assessment can reveal where the biggest opportunities lie. Small adjustments in the right areas can lead to significant improvements in both business performance and personal financial outcomes.

Conclusion

A business should serve its owner’s life, not the other way around. With the right planning, an owner can move from uncertainty to clarity, from reactive decisions to intentional strategy, and from simply building a business to building a lasting legacy. The core question remains: are you ready to start designing your future — on purpose?

TAKE THE FREE BUSINESS OWNER 3 MINUTE SURVEY: With this survey we will send you a report of where you are in your planning today vs. the areas you should revisit to maximize your planning we call this the “Where You Are, and Where You Could Be!” DOWNLOAD

Download your free “Growing Your Business Guide With GWT PLANNING SYSTEM® Download

Also, if you would like to discuss your current situation, I would be happy to help you with a discussion, feel free to contact me: MY Calendar

Youtube:  The Business Owners Who Plan vs. Everyone Else: Luck or Design

Thomas J. Perrone, CLU, CIC | tperrone@necgginc.com

Why So Many Business Owners Outgrow Their 401(k)—But Never Build the Retirement They Deserve

By Thomas J. Perrone, CLU, CIC

If you’ve built a successful business, you’ve already accomplished something most people never will.

You’ve taken risks, created jobs, served customers, and built something of real value.

Yet there’s one question that quietly follows many successful business owners throughout their careers:

Will my business be enough to fund my retirement?”

For many owners, the uncomfortable answer is, “I hope so.”

The Hidden Retirement Problem

Business owners think differently than employees. When extra cash is available, it usually goes right back into the business.

  • Hiring another employee.
  • Purchasing equipment.
  • Expanding operations.
  • Investing in marketing.
  • Solving the next challenge.

The business always seems to come first.

Over time, something surprising happens. The business becomes the retirement plan.

On paper, many owners appear wealthy because most of their net worth is tied up inside their company. But when it’s time to retire, they discover they haven’t created enough wealth outside of the business to support the lifestyle they’ve worked so hard to achieve.

That’s a risky position to be in.

Your Business Is an Asset—Not a Retirement Plan

Many owners assume they’ll simply sell the business one day and retire comfortably.

Unfortunately, life doesn’t always cooperate.

Markets change. Buyers disappear. Industries evolve. Health issues arise. Family circumstances shift.

A business that looks valuable today may not sell for what you expect tomorrow.

Even if it does sell, taxes, transaction costs, and changing market conditions can significantly reduce the amount you actually keep.

Putting your entire retirement future on one asset—even one you built yourself—is concentration risk.

The wealthiest business owners understand that retirement security comes from diversification, not hope.

Cash Flow Is the Real Challenge

Most owners don’t ignore retirement because they don’t care.

They ignore it because cash flow always seems to demand attention somewhere else.

There is payroll to meet.

Taxes to pay.

Inventory to purchase.

Unexpected expenses.

Growth opportunities.

Retirement planning becomes something they’ll “get to next year.”

Then next year becomes five years.

Five years becomes ten.

Before long, retirement is much closer than anyone expected.

Clarity Changes Everything

The biggest obstacle isn’t a lack of income.

It’s a lack of clarity.

Most business owners have never been shown a strategy that allows them to continue investing in their business while intentionally creating personal retirement wealth outside of it.

Once they understand how to redirect cash flow efficiently, retirement planning becomes less about sacrifice and more about strategy.

That’s when real confidence begins.

Introducing the GWT System

Our firm developed the GWT System® (Grow Wealth Transition) because we repeatedly saw successful business owners facing the same challenge.

They were building exceptional businesses—but not building enough personal retirement wealth.

The GWT System is designed to help business owners:

  • Create a clear retirement roadmap.
  • Build wealth outside the business.
  • Use tax-efficient executive compensation strategies.
  • Reduce dependence on selling the business for retirement.
  • Gain confidence that their personal financial future is as strong as the company they’ve built.

The goal isn’t to replace your business.

The goal is to ensure your business supports your retirement instead of becoming your only retirement plan.

You Deserve More Than Hope

You didn’t build your business by hoping things would work out.

You built it with planning, discipline, and smart decisions.

Your retirement deserves the same attention.

Imagine reaching retirement knowing your lifestyle doesn’t depend on the timing of a business sale or the state of the economy.

Imagine knowing your personal wealth is growing alongside your business.

Imagine having choices instead of uncertainty.

That’s what financial clarity creates.

The Next Step

If you’ve spent years building your business, now is the time to begin building the retirement you’ve earned.

The earlier you create a strategy, the more options you have.

The GWT System helps business owners turn today’s success into tomorrow’s financial independence—so retirement becomes a destination you can look forward to with confidence, not uncertainty.

Because after a lifetime of building your business, you deserve a retirement built with the same level of purpose.

Download the Free Report: Building Retirement Wealth Through Your Business” 

Landing page for the building retirement wealth through your business. 

New England Consulting Group of Guilford, Inc.

tperrone@necgginc.com

http://www.bpbpgrp.com/tom

The Human Side of Succession!

By Ken Somers

The Human Side Of Succession!

Last month May 25, 2026,  I wrote about Estate Equalization:  “ A Guide for Business Succession”. 

As a continuation of this topic, I would like to include a great article in audio form by my friend  Ken Somers from

The Somers HR SOLUTIONS Group 

The article  called “The Human Side of Succession”  is in audio form.   Ken hits on all cylinders in the discussion of estate equalization and succession. 

This is a wonderful perspective on business succession and the dynamics within the family business.  

Feel free to contact Ken for a hard copy of his paper, or to speak to him about the topic. 

linkedin.com/in/kensomers

somershrsolutions.com

ken@somershrsolutions.com

Listen  to Ken’s message:  Also, you can download the audio file

Transferring_power_in_family-run_businesses Ken Somers_copy.mp3

Thomas J. Perrone, CLU, CIC

tperrone@necgginc.com

www.bpbpgrp.com/tom