Why Every Family Needs a Trust & LLC (Not Just the Rich)
Small Business Tax Savings Podcast
Turning Vacations Into Legitimate Family Business Meetings
Jack explains how families can document annual meetings, invite speakers, and have kids pitch ideas as part of governance rituals.
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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