Funding Buy-Sell Agreements with Life Insurance After Connelly v. United States

Funding Buy-Sell Agreements with Life Insurance
After Connelly v. United States

Funding Buy-Sell Agreements with Life InsuranceFor closely held businesses, a well-drafted, properly funded buy-sell agreement is one of the most important—and most frequently mishandled—estate planning tools. A buy-sell sets the rules of engagement for what happens to an owner’s interest at death, disability, or departure and, when paired with life insurance, can provide the liquidity needed to keep the business and the family both financially secure.

But the Supreme Court’s decision in Connelly v. United States is a stark reminder that how you structure and fund that agreement can dramatically change the estate tax result. A buy-sell that looks fine from a corporate or succession-planning perspective can actually increase the taxable estate if the insurance and ownership mechanics are not carefully aligned with the valuation rules of the Internal Revenue Code.

Why Life Insurance Is the Workhorse Funding Vehicle

Most owners like the concept of a buy-sell agreement in theory. The friction usually arises around the question: “Where does the money come from to actually buy the deceased owner’s interest?”

Life insurance solves that problem elegantly:

      • It creates immediate, liquid cash at the exact time it is needed; upon an owner’s death.
      • It avoids forcing the company or the surviving owners to borrow on unfavorable terms or fire-sale assets just to complete the buyout.
      • It converts an illiquid business interest into cash for the deceased owner’s family, which is often far more useful for a surviving spouse or heirs who are not involved in the business.

In short, insurance is not the agreement; it is the funding engine that allows the agreement to work under real-world stress. The legal and tax consequences, however, depend critically on who owns the policy, who is the beneficiary, and how the buy-sell is drafted.

Common Structures: Cross-Purchase vs. Entity Redemption

Although there are hybrids and variations, most life-insurance-funded buy-sell plans fall into one of two basic models: cross-purchase or entity redemption (entity purchase). Each has distinct ownership, tax, and administrative implications.

Cross-Purchase Structure

Under a cross-purchase arrangement:

      • Each owner buys and owns a policy on the life of the other owner(s).
      • When an owner dies, the surviving owner(s) collect the death benefit personally and use it to purchase the deceased owner’s shares under the buy-sell agreement.
      • The surviving owners receive a basis step-up in the shares they purchased, which can be valuable if the business is later sold.

Advantages:

    • The insurance proceeds never sit inside the company itself, so they generally are not building the value of the corporation for estate tax purposes.
    • Surviving owners individually acquire more stock with a higher basis, which may reduce future capital gains on a sale.

Challenges:

      • With more than a few owners, the number of policies required can become unwieldy (each owner needs policies on each of the others).
      • Premiums may not be perfectly “equal” if there are big age or health differences among owners.

Entity Redemption Structure

Under an entity redemption:

      • The company owns policies on each owner’s life and is the beneficiary of those policies.
      • When an owner dies, the company receives the death benefit and uses those funds to redeem (buy back) the deceased owner’s shares under the buy-sell agreement.
      • The remaining owners’ percentage interests increase, but their tax basis in their shares does not.

Advantages:

      • Administrative simplicity: the entity owns one policy per owner, pays the premiums, and handles any changes centrally.
      • Often easier to explain and implement for larger ownership groups.

Risks:

      • Because the insurance proceeds are received by the entity, they increase the value of the company itself, which becomes a central issue for estate tax valuation.
      • If the agreement is not drafted and operated within the strict requirements of the valuation rules, the tax results can be far worse than expected.

The Connelly decision squarely focused on this entity-redemption model.

The Connelly Case: When the Insurance Creates the Tax Problem

In Connelly v. United States, the Supreme Court reviewed an estate tax dispute arising from a family-owned corporation that used a redemption-style buy-sell agreement funded with corporate-owned life insurance. The key facts, simplified:

      • The corporation owned a life insurance policy on a shareholder’s life and was the beneficiary.
      • The buy-sell agreement provided that on a shareholder’s death, the corporation would redeem the deceased shareholder’s stock using the insurance proceeds.
      • For estate tax purposes, the estate argued that the corporate-owned life insurance should effectively be ignored or offset by the corresponding obligation to redeem the shares; i.e., that the insurance did not increase the value of the corporation for valuation purposes.

The Supreme Court rejected that argument. The Court held that:

    1. The life insurance proceeds received by the corporation are a valuable corporate asset that must be included in the fair market value of the company when determining the value of the decedent’s stock for estate tax purposes.
    2. The corporation’s contractual obligation to redeem the decedent’s shares does not reduce the value of the corporation in that valuation exercise. A redemption obligation is essentially an arrangement among shareholders, not a corporate liability that diminishes enterprise value in the eyes of a hypothetical willing buyer.

The result was harsh: the insurance increased the company’s value for estate tax purposes, thereby increasing the value of the decedent’s shares, even though those same insurance dollars were earmarked to redeem those shares. The estate ended up paying estate tax on a higher value while the actual economic benefit to the family did not increase proportionately.

In addition, the Court and the IRS looked closely at the buy-sell agreement itself. The agreement failed to meet the requirements under Internal Revenue Code Section 2703 for an agreement to control value for estate tax purposes:

      • The agreement did not operate as a true, binding arm’s-length arrangement;
      • It was not consistently observed in practice; and
      • It did not provide a fixed or formula-based price that would be respected for valuation purposes.

Because the agreement was not respected as a bona fide price-setting mechanism, the IRS and the Court fell back to general fair market value principles, which included the insurance proceeds at full value.

The Estate Tax Risk of “Wrong” Structure

The lesson from Connelly is not that entity-redemption agreements are dead, but that they are dangerous if you assume the life insurance funding will be tax neutral at the corporate level.

The core estate tax risks include:

      • Inflated Estate Value: When the corporation owns the policies, the death proceeds can significantly increase the company’s value at the moment of death, directly increasing the decedent’s taxable estate.
      • No Offset for Redemption Obligation: A contractual requirement for the company to redeem shares using those same proceeds typically will not reduce the corporate value for estate tax purposes. The estate may feel like the insurance “just passes through,” but for valuation purposes it is effectively an asset that boosts the company’s worth.
      • Unrespected Buy-Sell Price: If the agreement’s price mechanism is not carefully drafted, regularly updated, and actually followed, the IRS may disregard the stated price and instead use a higher fair market value, including the insurance.
      • Mismatch Between Economic and Tax Outcomes: The family may end up with the same economic result they always expected (cash for shares, surviving owners with 100% of the company), but with a significantly larger estate tax bill, reducing the net value transferred to heirs.

For closely held businesses where the business interest is the primary asset in the estate, that mismatch can be catastrophic.

Drafting and Structuring After Connelly: Practical Guidelines

Attorneys and advisors can still use life insurance to fund buy-sell agreements effectively, but the post-Connelly environment calls for more precision in structure and documentation.

    1. Be Intentional About Policy Ownership

Consider whether corporate ownership of the policies is truly necessary, or whether a cross-purchase or alternative structure (such as a separate LLC or trust to own policies) can achieve the same funding benefits with less estate tax exposure.

      • For two or three owners, a traditional cross-purchase is often manageable and may keep the insurance proceeds out of the entity’s value.
      • For larger groups, look at techniques that centralize policy ownership outside the operating company rather than inside it.
    1. Tighten the Buy-Sell Agreement Under Section 2703

If you want the buy-sell to influence or control the value used for estate tax purposes, it must be drafted to meet the statutory and regulatory requirements:

      • Use a clear, objective price mechanism (such as a regularly updated formula tied to earnings, EBITDA multiples, or independent appraisals) rather than vague or ignored valuation language.
      • Require periodic updates to the stated value or formula and document those updates; then actually transact at those values when triggering events occur.
      • Ensure the agreement is binding on the parties both during life and at death, and that it resembles an arm’s-length arrangement rather than a device to artificially depress estate values.
    1. Coordinate Insurance, Valuation, and Corporate Records

The buy-sell agreement, the insurance policies, and the corporate records (minutes, cap table, financial statements) must tell a consistent story:

      • Confirm that policy ownership and beneficiary designations match the structure described in the buy-sell.
      • Ensure that financial statements properly reflect corporate-owned policies and that appraisers understand the treatment of those policies under current law.
      • Revisit both the agreement and coverage amounts as the business value changes; an outdated policy or stale valuation can be as dangerous as no planning at all.
    1. Model the Estate Tax Outcomes in Advance

For key owners, it is prudent to model:

      • The projected value of the business with and without insurance proceeds at death.
      • The resulting estate tax liability under different structures (cross-purchase vs. entity redemption vs. external policy-owning entities).
      • The net amounts expected to pass to family members after tax under each approach.

These projections help owners understand that “simpler” is not always safer and that the short-term convenience of entity-owned policies may carry long-term estate tax cost.

Takeaways for Business Owners and Advisors

Life-insurance-funded buy-sell agreements remain a powerful way to combine business succession and estate planning. They provide liquidity when it is needed most and can prevent families from being forced into bad deals or litigation in the wake of an owner’s death.

The Connelly decision, however, is a reminder that the tax law does not always align with intuitive economics. When the entity owns the life insurance and is the beneficiary, those proceeds may increase the value of the decedent’s stock for estate tax purposes, even if they are immediately used to redeem that stock under a buy-sell agreement. If the agreement itself is not drafted and operated to meet strict valuation requirements, the IRS and the courts may ignore the nominal “buy-sell price” and impose tax on a significantly higher value.

For that reason, buy-sell agreements should be reviewed not only through a corporate or transactional lens, but through an estate tax lens. Aligning the structure (cross-purchase vs. entity redemption vs. alternative ownership vehicles), the insurance funding, and the valuation mechanics is essential to avoid turning what was intended as a tax-efficient succession plan into an estate tax trap.

Michael A. WeaverIf you have an existing buy-sell agreement funded with life insurance—especially if the corporation owns the policies—this is an excellent time to have it reviewed in light of Connelly and to confirm that the structure will produce the estate tax result you actually intend. Mr. Michael A. Weaver, Partner at Saunders | Walsh, specializes in estate planning and corporate law and looks forward to working with you to build buy-sell provisions in your Company Agreement that work. Call us today to schedule your consultation with Mr. Weaver.

What Your Insurance Agent Needs to Know When a Living Trust Owns a Texas Series LLC

What Your Insurance Agent Really Needs to Know When a Living Trust Owns a Texas Series LLC

When a Living Trust Owns a Texas Series LLC:

What Your Insurance Agent Really Needs to Know

 

When you combine a living trust, a Texas series LLC, and multiple lines of business insurance, you create a structure that is great for asset protection but confusing for insurance underwriting. This post walks through the key issues that come up when an insurance agent calls to “understand the disregarded entity tax structure” and how you, as counsel or advisor, can be ready with clear, consistent answers.

  1. Who Really Owns and Controls the Business?

The first thing a business‑insurance agent wants to nail down is: who is the insured risk?

In a typical planning structure:

  • The revocable living trust is the sole member of the parent LLC.
  • That parent LLC establishes multiple series, each holding a specific asset pool or business line (for example, separate rental properties or operating ventures).
  • The trustee—often the grantor—is the manager of the LLC and its series.

From an insurance standpoint, the key is to make sure:

  • The parent LLC and the relevant series appear as named insureds or scheduled entities on the policy.
  • The trust and the individual trustee/grantor appear as additional insureds (or co‑named insureds where possible).

This alignment reduces the risk that a claim is denied because the “real party” with liability or ownership was never properly named on the policy.

  1. Disregarded Entities: Tax Fiction vs. Insurance Reality

For federal tax purposes, single‑member LLCs (including those owned by a grantor trust) are routinely treated as disregarded entities. In practice, that means:

  • Each series’ income flows through the trust and onto the grantor’s Form 1040.
  • The IRS looks through the LLC and trust and taxes the grantor directly.

Insurance carriers, however, do not underwrite tax fictions. They care about:

  • Which legal entity holds title to the property or employs people.
  • Where operations occur and who signs contracts and leases.
  • Whose financial statements (often the grantor’s return plus entity‑level books) reflect the risk they are insuring.

The smart move is to explain to the agent that the tax treatment doesn’t change who owns assets or runs the business; it simply affects how income is reported. Then offer:

  • EINs for each series and the parent LLC.
  • A short explanation of how the grantor trust and disregarded entities report on the individual return.

This lets underwriting connect the dots between entity‑level exposures and the individual’s tax return they’ll often see in underwriting.

  1. How Texas Series LLCs Affect Coverage Design

Texas series LLCs are popular for real estate and multi‑asset businesses because each series can hold its own assets and liabilities while sitting under a single umbrella LLC. For insurance, this raises several design questions:

  • Should each series be treated as a separate “location” under one master policy, or as separate insured entities?
  • Should there be one combined program (with clear scheduling of each series) or separate policies for each series?
  • How should limits and umbrellas be structured to respect internal liability segregation while still providing practical coverage?

A common, practical approach:

  • Use one coordinated program, with the parent LLC and each active series listed by name.
  • Clearly schedule properties and operations under the correct series on the declarations and schedules.
  • If certain series have meaningfully different risk profiles (e.g., high‑risk operations vs. passive real estate), consider separate policies or endorsements to avoid cross‑subsidization of risk.

The better you document which series owns what, the easier it is for the agent to avoid gaps.

  1. Trust Ownership: Why It Matters to the Carrier

Trust ownership introduces two issues carriers care about: control and continuity.

With a revocable living trust:

  • The grantor and the trust are economically the same person during the grantor’s life.
  • However, the trust instrument governs what happens on incapacity or death—when a successor trustee steps in, and how business interests transition.

Insurance implications include:

  • Ensuring the trust itself is recognized on the policy, so coverage continues seamlessly even if the grantor dies or becomes incapacitated.
  • Ensuring the trustee (and any successor trustee) is recognized as having authority to act for the insured entities.
  • Clarifying that any change in trusteeship or substantial amendment to the trust will trigger notice to the agent so the carrier can update the policy if needed.

When you proactively share a high‑level summary of the trust’s role—without revealing unnecessary private details—you reduce carrier anxiety about “mystery owners” behind the scenes.

  1. Business Income, Payroll, and “Who Is the Employer?”

When agents ask about “the disregarded entity tax structure,” they are often really asking about:

  • Whose income is at risk for business‑income and extra‑expense coverage.
  • Who is the employer for workers’ comp, employment‑practices, and related coverages.

In a common arrangement:

  • The payroll for each line of business runs through the specific series’ EIN, even though the series is disregarded for income‑tax purposes.
  • The books and records track revenue, expenses, and payroll by series, then roll up through the parent LLC and ultimately to the grantor’s return.

For underwriting clarity, it helps to be ready with:

  • Current payroll reports by entity/series.
  • A brief explanation of where business‑income coverage should respond (e.g., at the series level, based on its own revenue).
  • Confirmation that the tax “flow‑through” does not change which entity is responsible for payroll taxes and employment obligations.

This makes it easier to size limits and price the policy correctly.

  1. Documentation and Communication Best Practices

To make these calls productive and avoid follow‑up confusion, it’s worth investing in a simple documentation package:

  • A one‑page structure diagram showing the trust, the parent LLC, and each series with a short label (e.g., “Series A – Elm St. Rental,” “Series B – Equipment Leasing”).
  • A brief written summary (1–2 paragraphs) explaining:
    • That the trust is a revocable grantor trust.
    • That each series is a single‑member LLC owned by the trust and treated as a disregarded entity.
    • That all income flows to the grantor’s Form 1040, but assets and operations are legally held at the entity/series level.
  • A list of requested policy positions, such as:
    • Parent LLC and each series as named insureds or scheduled entities.
    • Trust and trustee as additional insureds.
    • Agreement to notify the agent on changes to trustees, series, or major operations.

Having this ready before the call lets you answer the agent’s questions consistently and gives the underwriter something concrete to work from.

  1. How to Talk About “Disregarded” Without Losing the Agent

Finally, remember that “disregarded entity” is tax jargon. In conversations with agents:

  • Emphasize that for legal liability, each LLC series still exists and owns assets or runs operations.
  • Clarify that for tax reporting, those entities are ignored and everything flows to the individual grantor’s return.
  • Tie every explanation back to what the carrier cares about: who owns the property, who operates the business, who employs people, and whose financials demonstrate the risk.

If you keep the focus on legal ownership, operations, and claims exposure, the tax‑classification piece becomes a simple background detail rather than a point of confusion.

Michael A. Weaver

 

Prepare Your Documentation Package Today

Don’t wait for the call from the underwriter. Proactively assemble the documentation package described in Section 6—including your structure diagram, high-level trust summary, and desired policy positions—to ensure a smooth, confusion-free underwriting process and avoid gaps in coverage. Need help? Contact Mr. Mike Weaver, Partner at Saunders | Walsh, today.  

What Every Commercial Tenant Should Know Before Signing a Lease in Texas

Avoid costly mistakes by understanding the fine print of your lease agreement.

Signing a commercial lease in Texas is a major business decision, and one that can impact your bottom line for years to come. Unlike residential leases, commercial leases in Texas are largely unregulated and highly customizable, which means tenants must be vigilant.

At Saunders, Walsh & Beard, we regularly help business owners navigate complex lease agreements. Here are some of the most important issues every tenant should understand before committing:

  1. Lease Type Matters More Than You Think
    Is it a gross lease, net lease, or triple net (NNN) lease? In NNN leases, which are common in Texas, tenants are often responsible for taxes, insurance, and property maintenance. Understanding the financial structure can help you avoid unexpected costs.
  1. Who’s Responsible for Repairs?
    Many Texas leases shift the burden of HVAC, roof, and even structural repairs onto the tenant. Always clarify responsibilities and consider negotiating a cap on major repair costs.
  1. Renewals and Early Termination
    Watch for automatic renewal clauses and rigid termination terms. If your business outgrows the space or operations stall, these clauses can trap you.
  1. Escalating Rent and CAM Charges
    Leases often include annual rent increases and Common Area Maintenance (CAM) fees. Ask for historic

    What to know before signing a commercial lease.

    al expense reports and consider negotiating audit rights and limits on increases.

  1. Use Restrictions
    A narrow use clause can prevent you from expanding services or subleasing. Request broader language that accommodates your current and future business operations.
  1. Assignment, Subleasing, and Exit Strategy
    Without the right language, landlords can block a transfer or keep you liable after you exit. Protect yourself by negotiating assignment rights and liability releases.
  1. Lockouts and Landlord Remedies
    Texas law permits commercial lockouts if rent isn’t paid. Ensure your lease includes notice and cure periods to avoid abrupt business interruptions.
  1. Personal Guaranties
    If you’re signing on behalf of an LLC or corporation, the landlord may still ask for a personal guaranty. Limit its duration and scope whenever possible.
  1. Dispute Resolution and Venue
    Arbitration clauses and far-away court venues can work against you. Aim for local venue provisions and consider requiring mediation before litigation.
  1. Improvements and Build-Outs
    Know whether you’re allowed to modify the space, and whether you’ll need to remove improvements when you leave. Ask about tenant improvement (TI) allowances upfront.
  1. Insurance and Liability
    Ensure your insurance obligations are reasonable and request a waiver of subrogation to protect against third-party claims.
  1. Force Majeure and Shutdowns
    After COVID-19, many landlords now exclude pandemic-related rent relief. Negotiate protections for future business interruptions.

 

Final Word: Protect Yourself Before You Sign
Texas is a landlord-friendly state. That’s why it’s essential to have a knowledgeable attorney review (and if necessary, negotiate) your lease before signing. At Saunders, Walsh & Beard, we’re here to ensure your lease works for your business, not against it.

Need help with a lease? Contact us today to schedule a consultation with a commercial real estate attorney.

The Benefits of Trademark Protection

The Benefits of Trademark Protection

When building your business, one of the most important assets you have is the brand itself. Whether it’s the name of your company, a slogan or a logo, finding distinct ways to represent your company will help build consumer awareness, enabling your business to grow. Filing a trademark with the United States Patent and Trademark Office (USPTO) offers significant benefits for protecting and growing your brand.

  • Exclusive U.S. Rights: When you file for a trademark, you will be granted exclusive rights to use the trademark in connection with your goods or services across the U.S., regardless of where you’re physically located. Additionally, it helps prevent others from using a confusingly similar name or logo.
  • Stop Copycats: Once you file with the USPTO, your mark becomes publicly searchable in the USPTO database. This deters others from adopting a similar name or logo because they can see it’s already claimed.
  • Public Deterrent: Registered marks are presumed valid, and you are presumed to be the rightful owner, thereby shifting the burden of proof to the other party in legal disputes and giving you a significant advantage.
  • Legal Advantage: Only federally registered trademarks can use the ® symbol, which enhances credibility and communicates legal protection. Unregistered marks can only use ™ (trademark) or ℠ (service mark), which carry less weight.
  • Sue Infringers: If you feel that another party is using an identical or similar version of your mark, you can file a lawsuit in federal court to stop infringement.
  • Sell It or Use It as Collateral: As trademarks are intellectual property assets, they can be sold, licensed, or used as collateral. Some entities choose to register their trademark not for the legal protection, but because it is an additional asset that they can sell, when they are looking to sell their company to a third party. A strong brand with legal protection can increase your company’s valuation and attractiveness to investors or buyers.
  • Keep Your Brand Consistent: Trademark protection helps maintain brand consistency. Consumers are more likely to trust brands with protected, recognizable marks.

In summary, registering a trademark with the USPTO is a powerful step toward building a secure, reputable, and scalable brand. It’s not just a legal safeguard; it’s a strategic and valuable business asset. 

Ready to secure your brand’s future? Contact Saunders Walsh & Beard today to learn more about protecting your intellectual property and unlocking the full potential of your business!

 

LLC vs Sole Proprietorship in Texas

Thinking of running your small business in your own name?


It’s common, but in Texas, forming an LLC or corporation offers big advantages.

When an individual starts their small business, they often do so in their own name. The thought process is typically that, as they are the only person involved with the business, there is no need to become a company or corporation. Not having employees or a payroll, some individuals think that the additional step of forming an entity is unnecessary and excessive. Some individuals do not believe they can form an entity when they are the only person involved with their business. What they may not know is that choosing not to operate as a sole proprietor in Texas and instead forming a Limited Liability Company (LLC), corporation, or other formal business entity can offer several key benefits.

1. Protect Your Personal Assets

With entities such as LLCs or corporations, owners are not personally liable for business debts, lawsuits, or obligations. Only the business assets are at risk. Inversely, sole proprietors (people who run businesses in their own personal names) are personally liable for all debts and legal actions against the business. Their personal assets (house, savings, etc.) could be at risk.

2. Boost Your Business Image

Additionally, by having “LLC” or “Inc.” in a business name may make the company appear more legitimate and professional, which can help when attracting investors, applying for business loans, and gaining client trust. While it might seem nominal, the suffix adds a measure of credibility and gravitas with potential clients and customers.

3. Enjoy Tax Flexibility

An individual who runs their business as a sole proprietorship has very few options when it comes to tax filings, whereas an entity allows for more versatility. An LLC can be taxed as a sole proprietorship, partnership, S corporation, or C corporation, depending on how an individual chooses to elect, providing the individual to optimize taxes based on their situation. There are multiple classifications of corporations. An S-corp enables pass-through taxation; avoids double taxation, while a C-corp has potential tax advantages on retained earnings but is subject to double taxation unless planned carefully. Inversely, a sole proprietor has no tax flexibility. All income is reported on their personal tax return (Schedule C), and they are subject to self-employment taxes on all profits.

4. Build a Stronger Business Foundation 

Formal entities provide a clear separation between personal and business finances as well as making it easier to build business credit and maintain legal protection.

An LLC or corporation can have multiple owners (members/shareholders) and is not tied to one person, making it easier to transfer ownership, bring on partners or investors, and continue operations if a member leaves or passes away. With a sole proprietor, the business ends with the owner and can be harder to transfer or sell.

Business entities such as LLCs or corporations provide for more formal structure with defined roles, governance, and rules (operating agreement, bylaws). Additionally, they can help prevent internal disputes and set clear expectations among owners or investors.

In sum, who Should Consider an LLC or Corporation?

  • Anyone worried about personal liability: Protect your assets!
  • Growing businesses: Hiring employees or seeking investment? Formalize your structure.
  • Businesses in “risky” industries: Healthcare, food services, consulting—consider the extra protection.
  • Those planning for the long-term: If you want to build a business that can continue beyond just you, an entity is crucial.

Don’t leave your future to chance. Contact us today to discuss forming an LLC or corporation in Texas.

 

Disclaimer: This blog post provides general information and not legal or tax advice. Consult with a legal and/or tax professional to determine the best entity type for your situation.