Estate Planning Failures, HSA Tax Strategies, & When DIY Backfires (4/18/2026)

Most people don't have a money problem—they have a follow-through problem. Brian Wiley and Jeremiah Bates use real-life case studies, including a massive estate mess left behind by Brian's own father, to show why DIY financial planning often leads to incomplete or broken outcomes—especially when trusts aren't properly funded or plans aren't kept up to date. The conversation goes into estate planning mechanics, breaking down how wills vs. trusts actually work, why co-trustee structures can create logistical nightmares, and how poor coordination leads to delays, legal headaches, and family tension (even when intentions were good). The guys also covers actionable planning topics, including when to pay off student debt versus investing, how to think through competing financial priorities, and a detailed listener question on using IRA funds to fund an HSA—highlighting rollover rules, contribution limits, and tax implications.  Plus, a key question for business owners: when it makes sense to move from a SIMPLE IRA to a 401(k), including higher contribution limits, added flexibility, and the real cost of compliance.   Listen, Watch, Subscribe, Ask! https://www.therealmoneypros.com Hosts Jeremiah Bates & Brian Wiley ————————————————————— Ataraxis PEO https://ataraxispeo.com Tree City Advisors of Apollon: https://www.treecityadvisors.com Apollon Wealth Management: https://apollonwealthmanagement.com/ —————————————————————