74: The Best of 2025 (A Retrospective)
Let's Talk Family Enterprise
Regular hosts Aileen Miziolek and Steve Legler discuss some of their favourite episodes and insights from 2025's episodes of the Let's Talk Family Enterprise podcast. Hear them share their greatest takeaways and bring back good memories while encouraging listeners to subscribe for more! All views, information, and opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of . Key Takeaways [0:26] Steve Legler and Aileen Miziolek come together for a year-end review for the Let’s Talk Family Enterprise podcast....
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73: Understanding ADHD in Family Enterprises
Let's Talk Family Enterprise
Host Aileen Miziolek speaks with Dr. Tamara Rosier about how ADHD can show up in adults and the common misconceptions that can shape family enterprise dynamics. They explore how traits such as emotional dysregulation, risk-taking and divergent thinking influence communication, trust and generational roles within enterprising families. Dr. Rosier also shares practical ways to design systems that support neurodivergent minds, and highlights the value of coaching and self-awareness in helping families work more effectively together. All views, information, and opinions expressed during this...
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72: Navigating Complexity in Enterprising Families
Let's Talk Family Enterprise
Host Steve Legler speaks with Michelle Osry about how families need to deal with both complicated issues that require specific solutions, as well as complex challenges that require different skills to navigate to help the family make progress. They discuss the challenges in getting both advisors and families to understand these distinctions and find ways to work on having each family's best outcome emerge from co-creation. Guest bio Michelle Osry works with family enterprises and offices on governance and generational transition. She draws from a broad experience and range of disciplines and...
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71: Parenting Adult Children in Family Business
Let's Talk Family Enterprise
Aileen Miziolek hosts an in-depth conversation with Alyson Schafer, an acclaimed author and Adlerian family counsellor. In this thoughtful 30-minute episode, they touch on issues around over- and under-functioning children, why the notion of fair vs. equal in childhood can impact long-term family business dynamics, and how tackling the unique challenges of enterprising families requires maturity, open-mindedness and an understanding that sometimes personal responsibility is the only path forward. All views, information, and opinions expressed during this podcast are solely those of the...
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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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69: The Skilled Facilitator
Let's Talk Family Enterprise
In this episode, Aileen Miziolek speaks with renowned facilitator and author Roger Schwarz about the critical roles facilitators and consultants play—especially in complex systems like family enterprises. Roger explores how mutual learning, clear boundaries and transparency can elevate the value professionals bring to their clients, offering practical insights and tools for navigating advisory roles with compassion and clarity. All views, information, and opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of ....
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68: Stop Frankensteining It
Let's Talk Family Enterprise
Join host Steve Legler for a video episode with guest Cindy Radu, recorded at the 2025 Family Business Symposium right after Cindy's session, which she conducted for a room full of attendees. Together, they discuss the challenges of professional collaboration when working with families, and highlight just how important it is for the families we serve so they don’t end up having to deal with a “scary monster.” 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 Cindy...
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67: Wealth, Continuity & the Long Game: Insights from Philip Marcovici
Let's Talk Family Enterprise
Host Aileen Miziolek sits down with Philip Marcovici to explore long-term wealth continuity, the pitfalls of tax policy and how enterprising families can avoid common traps while building meaningful legacies. 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 Philip Marcovici is retired from the practice of law and consults with governments, financial institutions, and global families in relation to tax, wealth management, and other matters. An area of focus for Philip...
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66: Fatherhood Unlocked
Let's Talk Family Enterprise
Host Steve Legler speaks with Dan Doty, an executive and wilderness guide, about his upcoming session at Family Enterprise Canada's Symposium in Halifax. Together, they discuss the challenges that fathers face when leading a business and a family, and how the roles and expectations of fathers are rapidly evolving. 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 Dan Doty is a writer, wilderness guide, men’s work leader, and somatic meditation teacher, and has...
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65: "Owning" Ownership with Barbara Dartt
Let's Talk Family Enterprise
In our 65th episode, Aileen Miziolek sits down with ownership expert and co-author of Own It!: How to Develop a Family Enterprise Owner's Mindset at Every Age, Barbara Dartt, to ask her how she started and grew her career in the family business consulting world, what being an owner of a family enterprise can mean and the different roles that owners often have to navigate in their ownership journey. 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 Barbara Dartt has...
info_outlineSteve 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 fea@familyenterprise.ca.
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
More about Family Enterprise Canada