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July 21, 2026 30 mins

What if the biggest risk to your family’s wealth isn’t the money, but the silence around it? The conversations that never happen, the assumptions that go unspoken, the lessons we hope our kids just “pick up” along the way.

In this episode, Joline Godfrey sits down with estate planning attorney and author Mark Shiller to explore a question many families quietly carry: how do you support your children financially without unintentionally holding them back? Together, they dig into what it really means to prepare the next generation, not just financially, but as thoughtful, capable humans.

Joline and Mark discuss:

  • Why families often come in for technical help, but what they really care about is how money impacts the people they love
  • The growing shift over the past 5 to 10 years, with more families opening up conversations that once felt off-limits
  • Why parents and grandparents cannot outsource these conversations, and need to take an active role in guiding their children
  • A powerful metaphor of the apple tree, reframing legacy as something that grows and continues, not just something that is consumed
  • And more

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About our Guest: 

Mark works with individuals, couples, and families in connection with their estate, tax, and business planning. His clients are typically business owners, professionals, and senior executives who appreciate his thoughtful and creative approaches to their often complicated personal, tax, and financial planning challenges.

Mark has been quoted in such publications as Smart Money and Worth and has been a frequent speaker on estate planning topics. He is a Fellow of the American College of Trusts and Estates Counsel, former Chair of the Board of Governors of the Real Property, Probate and Trust Law Section of the State Bar of Wisconsin, Past President of the Milwaukee Estate Planning Forum, and Past Chair of the Estate and Trust Law Section of the Milwaukee Bar Association. Mark also served as an adjunct professor at the University of Wisconsin Law School for four years, teaching a course on estate and business planning for a privately held enterprise.

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