Category Archives: Estate Planning

A business partnership is a lot like a marriage, but with more paperwork and significantly higher financial stakes. You spend more time with your partners than your family. you build a legacy together, and you trust each other with your professional lives. But there is a universal truth that every business owner eventually has to face: every partnership will end.

The question isn’t if it will end, but how. Will it end with a smooth transition and a handshake, or will it end in a tax-fueled legal nightmare that leaves your family: and your partner’s family: scrambling for liquidity?

Most business owners have a Buy/Sell agreement tucked away in a dusty drawer. They signed it years ago, checked the box, and moved on. But the world has changed. Tax laws have shifted. Court cases have redefined how the IRS looks at your business value. If your agreement hasn’t been touched in three years, it’s not just outdated: it’s a ticking time bomb.

The Problem: When Protection Becomes a Tax Trap

For decades, the standard play was the "Entity Purchase" or "Redemption" agreement. The business owns a life insurance policy on each owner. If an owner passes away, the business gets the cash and uses it to buy back the shares from the deceased owner's estate. Simple, right?

Not anymore.

A recent, massive shift in the tax landscape: specifically the Connelly v. United States decision: has turned this "simple" strategy into a potential catastrophe. The Supreme Court essentially ruled that if the company receives life insurance proceeds to fund a buyout, those proceeds can be included in the company’s total valuation for estate tax purposes.

Imagine this: Your business is worth $10 million. You have a $5 million life insurance policy to buy out your partner. If you pass away, the IRS could argue the business is now worth $15 million because of that insurance cash. Your estate is taxed on a $7.5 million valuation (your half), but your family only receives the $5 million you originally agreed upon.

You’re paying taxes on money your family never sees. Does that sound like "protection" to you?

100% Protection for the Families Who Built the Business

When we talk about Buy/Sell agreements at Schiff Executive Benefits, we focus on the human element. Your spouse and your children shouldn't have to become "accidental business partners" with your co-founder. Likewise, your surviving partner shouldn't have to report to your heirs who might not know the difference between a P&L and a balance sheet.

The goal is 100% Protection.

This means the family of the deceased receives the full, fair market value of the business interest immediately, in cash, with zero tax friction. It also means the surviving owner gets 100% control of the company without taking on massive debt or draining the corporate coffers.

The Solution: Modernizing via the Cross-Purchase Strategy

To avoid the "Connelly Trap," many savvy owners are moving toward a Cross-Purchase or a Trusteed Cross-Purchase structure.

In a traditional cross-purchase, the owners own policies on each other. Because the business doesn't own the money, it doesn't inflate the business's value in the eyes of the IRS. But the real magic happens with something called the "step-up in basis."

When you use insurance proceeds to buy your partner’s shares personally, your tax basis in the company increases. If you ever decide to sell the business later, that "step-up" could save you millions in capital gains taxes. It is the definition of tax efficiency.

However, if you have three or four partners, owning individual policies on everyone gets messy. That’s where we modernize. We often implement an LLC Insurance Ownership structure. You create a separate entity (taxed as a partnership) specifically to hold the life insurance. It provides the creditor protection of a corporation, the tax benefits of a cross-purchase, and the administrative ease of a single plan.

Is Your Agreement Part of The Perfect Plan®?

At Schiff Executive Benefits, we don't look at insurance in a vacuum. We look at how it fits into your broader financial legacy: what we call The Perfect Plan®.

A modern Buy/Sell agreement isn't just a legal document; it’s a wealth-transfer vehicle. It’s part of a strategy that uses corporate dollars tax-efficiently to build personal security.

Ask yourself these three questions:

1. How is the value determined? If your agreement uses a "fixed price" from five years ago, you are either overpaying or cheating a family out of their legacy.


2. Where does the tax go? If your plan triggers a massive estate tax bill or a capital gains nightmare, it’s a failure.


3. Is it funded? A legal obligation to buy shares is worthless if the company doesn't have the liquidity to write the check.

If you can’t answer these with 100% certainty, you are leaving your business and your family's future to chance.

The ROI of Getting it Right

We often hear owners say, "I'll get to it next year." But the cost of waiting is higher than you think. A well-structured, modern agreement doesn't just protect you upon death; it sets the stage for a healthy exit, a smooth retirement transition, and even better terms with lenders who want to see a solid succession plan.

Think of it as the ultimate insurance for your life's work. You’ve spent decades building this company. You’ve survived market crashes, hiring woes, and global shifts. Why let a preventable tax headache dismantle it all at the finish line?

Stop Worrying and Start Planning

You shouldn't have to stay up at night wondering if your partner’s spouse will end up sitting in your boardroom or if the IRS will take a 40% bite out of your family’s inheritance.

Modernizing your Buy/Sell agreement is about more than just "insurance." It’s about clarity. It’s about ensuring that the value you’ve built stays where it belongs: with the people who built it and the families who supported them.

We help business owners navigate these complexities every day. We coordinate with your legal team and your CPA to ensure the math, the law, and the logic all point in the same direction: your success.

Let’s get your plan off the "to-do" list and into the "done" column.

Grab a coffee, take a breath, and let’s look at the numbers together. You can visit our website to learn more about our approach or schedule a quick discovery call via my Calendly to see if your current agreement is helping you or hurting you.

Your legacy is too important to leave to an outdated contract. Let's make sure it's protected: 100%.

Learn more: planning your business succession.