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Trusts aren’t just for the rich. Every family can benefit from one. A revocable living trust can simplify estate planning, avoid probate, and create a foundation for generational wealth.

In this episode, Mike Jesowshek, CPA, sits down with Jack Fiveash, attorney and co-founder of The Co Letter, to talk about how families can use a simple trust and LLC structure to build long-term stability, protect assets, and involve their children in smart financial stewardship.

They cover how to start a revocable trust, the ideal timing, what it costs, and how it ties into a broader family office structure that preserves both wealth and values.

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Chapters

(00:00) Intro to Family Office Structures
A family office isn’t only for the ultra-wealthy.

(02:41) Understanding Revocable Living Trusts
What is a revocable living trust (RLT), why every family should have one, and how it simplifies estate planning.

(04:43) When to Create a Trust for Your Kids
Jack explains the right time to create a trust for children and how even young people with digital assets or investments can benefit from having one in place.

(06:53) Cost and Process of Setting Up a Trust
Jack outlines realistic pricing, what makes a trust legally sound, and the importance of completing a general assignment to fully fund the trust.

(09:44) Funding the Trust and Avoiding Probate Issues
Jack describes how a trust must be properly funded through title changes and assignments to avoid probate disputes later.

(10:22) Involving Family Members Early
Jack and Mike discuss including children in the family LLC, teaching financial stewardship, and using legitimate methods to instill responsibility and long-term wealth habits.

(13:38) Family Business Meetings and Board Structure
How to formalize family board meetings, even on vacations, to build both structure and tax efficiency.

(18:30) Structuring Family Business Entities
When to create new entities versus using existing businesses, how to integrate wills and trusts into ownership.

(20:46) Building a Foundation for Generational Wealth
Jack offers guidance for those just starting to build wealth: How to use simple structures like family LLCs or educational trusts to create lasting value for children and grandchildren.

Learn more about family trusts, LLCs, and governance at https://thecoletter.beehiiv.com

Podcast Host:

Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast
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