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70: How to NOT Ruin Your Kids With Money

Let's Talk Family Enterprise

Release Date: 08/21/2025

70: How to NOT Ruin Your Kids With Money show art 70: How to NOT Ruin Your Kids With Money

Let's Talk Family Enterprise

Steve Legler speaks with U.S. estate planning attorney Mark Shiller about his book, How to NOT Ruin Your Kids With Money: Navigating the Challenges of Transitioning Wealth in Families. Together, they discuss issues around character, competence, and capacity, the maturation process, and the uniqueness of each family member, with lots of useful tidbits for parents and rising generation family members along the way.   All views, information, and opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of .   Guest bio...

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Steve Legler speaks with U.S. estate planning attorney Mark Shiller about his book, How to NOT Ruin Your Kids With Money: Navigating the Challenges of Transitioning Wealth in Families. Together, they discuss issues around character, competence, and capacity, the maturation process, and the uniqueness of each family member, with lots of useful tidbits for parents and rising generation family members along the way.

 

All views, information, and opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of Family Enterprise Canada.

 

Guest bio

Mark A. Shiller has been a practicing estate and business succession attorney and wealth consultant for over 20 years. He 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.

 

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 the privately-held enterprise.

 

You can learn more about Mark Shiller on his website and LinkedIn.

 

Key Takeaways

[:26] Steve Legler welcomes Mark Shiller and asks him to share about the process that took him through to writing his book.

 

[3:48] The minority, maturation, and maturity needs of any person impact their relationships with others and wealth; Marc shares an anecdote.

 

[6:16] Wealth magnifies and reveals character; money can enable people to do damage.

 

[8:08] Mark explains why resisting the urge to “fix it for them” is important when it comes to advising families.

 

[12:08] Mark’s allowance system and how it both worked and failed.

 

[14:52] Money conversations shouldn’t be all or nothing; raising kids is a process.

 

[16:34] What’s the purpose of apple trees?

 

[19:02] The definition of success as a parent shouldn’t be an imposition; involving the upcoming generation is a requirement of a continued legacy.

 

[21:44] Modelling as a way of ensuring success.

 

[22:47] On Al, Brittany and Carl, and the difference between value and virtue.

 

[26:45] The danger zone and some tips on how to navigate it best, according to Mark.

 

[29:32] Mark’s book recommendation and advice for advisors.

 

[32:13] Steve thanks Mark Shiller for sharing his wisdom, and closes this episode by reminding listeners to rate and subscribe.

 

If you enjoyed today’s episode, you can subscribe to Let’s Talk Family Enterprise on Spotify, Apple Podcasts, and other podcast apps. Please remember to share this episode with family, friends, and colleagues.

Share your thoughts with us at [email protected].

 

Mentioned in this episode

How to Not Ruin Your Kids with Money: Navigating the Challenges of Transitioning Wealth in Families, by Mark Shiller

 

How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen, by David Brooks

 

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