Business Lunch

The Estate Planning Mistake That Tears Families Apart (Jimmy Buffett's $275M Lesson)

September 17, 2026·48 min
Episode Description from the Publisher

In This Episode Of Business Lunch: Jimmy Buffett left a 275 million dollar trust, and now his widow and his longtime business manager are suing each other in two states while the legal bills run into the millions. Roland Frasier, who practiced estate law for about 12 years, and Ryan Deiss use that fight to make a case most advisors never make: the estate plan that saves the most tax is often the one that tears the family apart. They cover who actually needs complex trusts (almost nobody under 30 million dollars), what they each plan to leave their own kids, what should happen to the business, and the few simple moves that protect a family without giving anyone you love the right to sue anyone else you love. This is a conversation about what they do themselves, not legal advice.Chapters:0:00 Welcome back, Ryan Deiss, and a business that keeps running when life happens1:58 Today's topic: structuring things for when you are not there3:08 Jimmy Buffett's 275 million dollar trust fight and the James Brown estate9:30 Under 30 million dollars, you do not need the complex structures12:39 What Roland wants for his kids: education, a house, shared experiences, no control from the grave16:41 Ryan Deiss on stewardship and deciding who gets what21:04 Never create an estate plan that gives people you love standing to sue each other24:29 Tell your kids to expect nothing, and spend on experiences while you are alive27:33 What happens to the business, and do the kids have to be treated equally?34:05 Two simple tools: 14 years to pay estate tax on a business, and life insurance trusts36:30 Give your beneficiaries the right to remove the trustee39:27 The one box on the estate tax return that can cost a surviving spouse 6 million dollars42:23 Six figure trust setups on small estates, and the human side advisors miss47:09 Recap: the three moves to make, and the question to ask every advisorListen to Business Lunch:Apple Podcasts: https://podcasts.apple.com/us/podcast/business-lunch/id1442654104Spotify: https://open.spotify.com/show/0iWSA89TaD263zhXETdSvZFollow Roland Frasier:Instagram: https://www.instagram.com/rolandfrasier/LinkedIn: https://www.linkedin.com/in/rolandfrasier/TikTok: https://www.tiktok.com/@rolandfrasierFacebook: https://www.facebook.com/RolandFrasierPage/Everything else: https://msha.ke/rolandfrasier/Follow Ryan Deiss:Instagram: https://www.instagram.com/ryandeiss/LinkedIn: https://www.linkedin.com/in/ryandeiss/X: https://x.com/ryandeissVisit: https://www.scalable.co

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