The Buy-Sell Market is Wide Open – and Most Adviosrs Are Walking Past It
Roughly 10,000 Baby Boomers turn 65 every day. A significant number of them own businesses. Most of those businesses have no formal succession plan, no funded buy-sell agreement, and no advisor who has ever asked them the right questions. That is not a planning problem — it is a market opportunity.
The Scale of Opportunity
The small business market in the United States is enormous and chronically underserved. According to the Small Business Administration, there are approximately 33 million small businesses in the U.S., and small businesses account for 98% of all U.S. employers. They employ more than 40 million people. These are not abstract statistics — they represent the clients already sitting in your book, and the prospects working in the office park down the street.
The demographic wave behind this market is just as compelling. Baby Boomers — the generation born between 1946 and 1964 — founded or built the majority of closely-held businesses in America. They are now in their 60s and 70s. Research consistently shows that approximately 40% of business owners expect to retire within the next ten years. That means the succession planning clock is running on a large portion of your potential market right now.
And yet, despite the urgency, up to 60% of business owners have no formal succession plan in place. Think about that number for a moment. Six out of every ten business owners have built something of significant value and have done nothing meaningful to protect it, transition it, or fund the transfer of it. For family-owned businesses — which represent 80% to 90% of all business enterprises — the situation is even more sobering: only 30% survive into the next generation, and just 12% remain viable into the third generation.

The gap between what business owners need and what they actually receive from their advisors is not anecdotal — it is documented and quantified. Research from the Spectrem Group surveyed affluent investors on the services they expect from their primary financial advisor versus the services they actually report receiving. The results are striking across the board. But one data point stands completely apart.
Business succession planning: 80% of business owners expect their advisor to address it. Only 1% report actually receiving it.
That is a 79-point gap — the single largest service gap in the entire Spectrem study. Investment management shows a 7-point gap. Even estate planning shows a 71-point gap. Business succession planning sits at the absolute bottom of the “services received” column while ranking among the highest in client expectations. The data could not be clearer: this is the most underserved planning category in the entire advisor-client relationship.



What Business Owners Actually Need
The term “succession planning” is often used loosely, and it is worth being precise. Succession planning is the broader process of identifying the key factors that make a business successful and creating a blueprint for what happens when the owner is no longer involved — whether through retirement, disability, or death. A buy-sell agreement is one critical component of that plan, but it is not synonymous with the whole.
For advisors working in this market, the buy-sell conversation is often the most immediate, most fundable, and most neglected piece of the puzzle. A buy-sell agreement is a legally binding contract that governs what happens to an owner’s interest in the business upon a triggering event: death, disability, retirement, divorce, or bankruptcy. Without one, the consequences can be severe — an unwanted co-owner, a family forced to liquidate, a thriving business dissolved because no one planned for the obvious.
There are two broad categories of buy-sell client, and both deserve your attention:
- Multi-owner buy-sell: Co-owned businesses — two or more owners who need a mutual agreement that addresses what happens to each owner’s interest if any one of them cannot continue.
- One-way buy-sell: Single-owner businesses with a designated successor — a family member, key employee, or management team member who is expected to acquire the business. This is the classic one-way buy-sell, and it is a larger market than most advisors recognize.
Over the course of my career, the single-owner client with a named successor has been one of the most consistently productive sources of buy-sell business. The owner has built something of value, knows who should carry it forward, and in most cases has never had a structured conversation about how that transfer gets funded. Life and disability insurance are the natural solution — and the conversation almost always opens a broader relationship.
Consider what is actually at stake for these clients. For most small business owners, the business is not simply a source of income — it is their single largest asset and, in many cases, their de facto retirement plan. Research from the Federal Reserve’s Survey of Consumer Finances found that the median net worth of self-employed families is more than four times that of wage-earning families. That wealth, however, is overwhelmingly concentrated in one place: the business itself. According to SCORE, 34% of entrepreneurs have no formal retirement savings plan of their own, and 18% intend to fund their retirement primarily through the sale or transfer of their business.
That is the hidden vulnerability in every single-owner buy-sell conversation. It is not just about what happens to the business at death — it is about whether the business transition actually produces the retirement resources the owner is counting on. A successful, funded succession plan is not a business planning document. For many owners, it is their retirement plan. When that transition fails — when the business dissolves, is sold under duress, or transfers without adequate funding — the financial consequences for the owner’s family can be severe and irreversible. That urgency belongs in every buy-sell conversation you have.

Why Disability Is Half the Conversation Advisors Are Missing
When advisors think about buy-sell planning, they typically think about death. Death is dramatic, it is certain eventually, and it is easy to illustrate. But research consistently shows that a business owner is significantly more likely to experience a long-term disability before age 65 than to die before that age. And in many respects, disability is more financially damaging to a business than death.
At death, the buy-sell is triggered cleanly. Insurance proceeds fund the purchase. The estate is settled. But disability creates ambiguity: Is the owner coming back? Who makes decisions in the interim? How long does the business wait before triggering the buy-out? An owner who is disabled but not deceased can become an involuntary silent partner — entitled to distributions, unable to contribute, and legally difficult to remove without a properly drafted and funded agreement.

Every buy-sell engagement should include a parallel conversation about disability insurance funding. The two coverages are complementary; they address the same fundamental risk from different angles, and the disability piece is often where the most significant planning gap exists. When you lead with both life and disability insurance in the context of buy-sell planning, you are providing the complete solution — and differentiating yourself from the vast majority of advisors who stop at life insurance alone.
Structure Matters: Matching the Agreement to the Client
Not every buy-sell is structured the same way, and the structure has meaningful planning and tax implications. There are six primary structures in common use, each with a distinct profile of advantages and considerations:
- Entity Purchase (Stock Redemption): The entity purchases the departing owner’s interest directly, funded by business-owned life insurance. Simple to administer, especially with three or more owners — but now carries meaningful estate tax implications following the Supreme Court’s 2024 ruling in Connelly v. United States.
- Cross-Purchase: Each owner personally owns insurance on the lives of the other owners, and uses the proceeds to purchase the departing owner’s interest. Provides a cost basis step-up for the surviving owners. Works cleanly with two owners but can become administratively complex with three or more.
- Cross-Endorsement Buy-Sell (CEBS): Each owner owns a policy on their own life and endorses a portion of the death benefit to the co-owners. Preserves personal ownership and basis step-up advantages. However, the endorsement of a death benefit for a rental charge may itself constitute a transfer for valuable consideration under IRC §101(a)(2) — a risk that is particularly acute for C and S corporation owners, where no clean statutory exception applies. The standard solution is to establish a partnership or LLC among the owners, bringing the arrangement within a recognized transfer-for-value exception. Note also that CEBS applies to life insurance only; disability must always be funded separately.
- Insurance LLC: A newly formed LLC owns the policies on all owners’ lives, providing the administrative simplicity of entity ownership while preserving basis step-up benefits and avoiding the Connelly estate tax issue.
- Trusteed Buy-Sell: An independent trustee holds and administers the policies, providing professional oversight and continuity. Particularly useful when owner relationships are complex or when impartiality in administration is valued.
- One-Way Buy-Sell: The business owner agrees to sell — and the designated successor agrees to buy — the business interest at a specified triggering event. The successor’s life insurance provides the funding. A simple, powerful structure for the single-owner market.
The Connelly Decision: A Review Trigger, Not a Crisis
In June 2024, the Supreme Court issued its ruling in Connelly v. United States, confirming that life insurance proceeds owned by a closely-held corporation are included in the fair market value of that corporation for estate tax purposes — without any offsetting deduction for the corporation’s buy-sell obligation. This was not entirely unexpected by tax practitioners, but it formalized a risk that had previously been theoretical for many entity purchase buy-sell clients.
The practical implication: business owners with entity-owned life insurance and meaningful estate tax exposure now have a planning problem that did not exist — or at least was not confirmed — before this ruling. For clients whose combined estate value (including the inflated business value) exceeds the applicable federal or state estate tax exemption, the entity purchase structure may no longer be the right answer.
For advisors, Connelly is not a crisis — it is a review trigger. Any client with an entity-owned buy-sell funded with life insurance warrants a structured conversation about whether the current structure remains appropriate given their estate size, ownership structure, and the magnitude of the death benefit relative to business value. The alternative structures — cross-purchase, CEBS, Insurance LLC — all avoid the Connelly problem while preserving the buy-sell function.

It is also worth noting that the urgency of a Connelly review is proportional to the client’s estate tax exposure. The One Big Beautiful Bill Act increased the federal estate tax exemption to $15 million per individual ($30 million per married couple), effective January 1, 2026, and made it permanent. Business owners whose total estates are comfortably below that threshold may have limited immediate exposure. However, for business owners in higher-value industries — or those whose business value, life insurance proceeds, real estate, and personal assets combine to approach or exceed $15 million — the Connelly issue is very much alive. And in the 17 states plus the District of Columbia that impose their own estate or inheritance taxes, the relevant threshold is often far lower, meaning state-level exposure can exist well before federal taxes come into play.
Three Questions That Open Every Door
The buy-sell conversation does not require a complex technical presentation to get started. In my experience, three questions — asked in the right context — open virtually every door:
- When did you last conduct a formal valuation of your business?
- When did you last review your buy-sell agreement and confirm your coverage is still adequate?
- If you are the only owner – who buys this business when you are gone, and how will they pay for it?
The first question exposes the valuation problem — most owners either have no formal valuation or have not updated one in years, which means their coverage is almost certainly out of date relative to what the business is actually worth today.
The second question surfaces the review need — buy-sell agreements age poorly when untended. New owners join without being added to the agreement. Businesses grow, but coverage does not. The legal document says one thing; the funding says another.
The third question — the single-owner question — is often the most powerful one in the room. Most sole proprietors have never been asked it directly. They know who they want to take over the business. They have never had a conversation about how that person actually pays for it.
The Market Is Wide Open — For Those Who Ask
Here is the honest picture of where the buy-sell market stands today. The need is enormous, well-documented, and growing as the Boomer generation ages into retirement. The awareness among business owners of their own exposure is limited — not because they are unsophisticated, but because no one has walked them through the right questions. And the advisor community, broadly speaking, has underserved this market for years.
The service gap is real. Business owners consistently report that their financial advisors do not raise business planning topics proactively. The advisors who do — who develop fluency in buy-sell structures, who understand the Connelly landscape, who can speak to both life and disability insurance in the same conversation — are building practices that are meaningfully different from the competition.
Business owners are fiercely loyal clients. When they find an advisor who understands their world — who asks the questions no one else has asked, who brings solutions rather than products — they do not leave. And they refer. Every satisfied business owner client is a pathway to the next business owner client.
The tools and structures exist. The need is undeniable. The market is wide open. The only question is which advisors show up prepared to serve it.
Contact the AgencyONE Advanced Markets Department at 301.803.7500 for more information or to discuss a case!

























