When people think of estate planning, they often picture wills, trusts, and passing down personal assets to family. But for business owners—especially those with intellectual property, partnerships, or a growing brand—estate planning isn’t just about inheritance. It’s about protecting your life’s work.

And if you think it’s only about retirement or old age, think again.

How Bob Ross’s Estate Planning Mistake Became a Cautionary Tale for Business Owners

Bob Ross brought joy to millions through The Joy of Painting, but after his death, his legacy became tied up in court battles—not because he failed to create a will, but because his estate plan didn’t match his business agreements. Although Bob meant to leave his intellectual property (IP) to his son, the courts ruled he didn’t legally own those rights when he died. Why? Because he had already transferred them to his company, Bob Ross Inc., during his lifetime—making them untouchable by his estate plan.

The Lesson: Estate Plans Don’t Override Business Agreements

This is a common misconception among business owners: they believe a will or trust alone will transfer business assets to their family. In California, and everywhere else, business ownership is determined by contracts, not by your estate plan.Whether you’re running a solo LLC or a family corporation, your business operating agreement, bylaws, or partnership contract will govern what happens to your ownership shares—not your will. That’s why estate planning and business planning must go hand-in-hand. This isn’t just a celebrity mistake. Business owners across all industries make similar missteps.

Modern Business Blunders: When Estate Planning Falls Short

Connelly v. United States (2024)

A family business faced a $900,000 estate tax bill—despite having a buy-sell agreement in place. Why? Because the agreement wasn’t coordinated with estate tax law. A costly reminder that not all legal plans are created equal.

The Sol Goldman Estate Battle (2025)

A $1.7B real estate empire is now the center of a family feud. With no clear leadership plan, Goldman’s heirs are tied up in court. Relationships are strained. Fortunes are at risk. And it all could’ve been avoided with a better roadmap.

The Cowboy Jack Clement IP Tangle

Country music pioneer Jack Clement left behind a musical legacy—but no clear estate plan for his trademarks or royalties. His heirs are now battling over who owns what, and who gets what.

What These Stories Teach Every Business Owner

You don’t need to be a celebrity to learn from these examples. Whether you run a bakery, law firm, design studio, or YouTube brand, your business—and everything tied to it—needs to be protected.

Here’s what a smart estate plan must do:

  • Coordinate with Business Agreements: Your LLC operating agreement, partnership contract, or shareholder deal needs to match your estate documents. A will alone won’t cut it.
  • Plan for Intellectual Property (IP): Trademarks, copyrights, digital assets, and proprietary work must be inventoried and transferred properly—or risk being lost.
  • Create a Succession Plan: Who steps in when you’re gone? Who can legally make decisions, access funds, manage operations, or sell the business? If the answer is unclear, your business may not survive.
  • Be Reviewed Regularly: Life changes. Laws change. Businesses evolve. If your plan is more than 3–5 years old—or you’ve never updated it—there’s risk you didn’t account for.
  • Your Business Is a Legacy: Treat It Like One. If you’re a business owner, your company isn’t just income. It’s time, sweat, ideas, and value you’ve built over years. Without a proper estate plan, all of that can be lost, taxed, or tied up in court.

At Tyre Law Group, as Personal Family Lawyers, we help you:

  • Align your business and estate documents
  • Protect your IP and revenue-generating assets
  • Create a smart, custom succession plan
  • Avoid court, conflict, and chaos—for your family and your team

Let’s Talk About Your Business Legacy

Book your Family Wealth Planning Session today.