Steve (caller)
Retired small-business owner and caller seeking advice about managing a recent $500,000 inheritance currently held in CDs and how it should fit into his retirement plan.
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Nov 19, 2025 • 24min
How to Manage Inherited Money
Steve, a retired small-business owner, inherited $500,000 in CDs and seeks advice on managing this windfall in light of his retirement plans. They discuss whether to invest or keep it liquid for peace of mind. Jill emphasizes a balanced withdrawal strategy, encouraging Steve to preserve his Roth IRA while considering municipal bonds for better tax efficiency. They also address the importance of financial comfort with advisors and the need for a second opinion on investment choices. Ultimately, it's about protecting his financial future while ensuring a safety cushion.
Mar 8, 2026 • 10min
My Mom Won't Stop Racking Up Debt (I've Already Paid Off Thousands for Her)
Steve, a son who has paid thousands to cover his elderly mother’s debts, describes a long pattern of bailing her out. He talks about stopping credit-card bailouts, confronting guilt and boundaries, legal options like power of attorney, and questions about bankruptcy and consolidation. Short, emotional, and practical money-and-family tension.
