Retirement isn’t just about what you earn — it’s about what you keep. In this episode of That Financial Guy Show, Keith Wilson breaks down the overlooked tax traps that quietly drain retiree income and create unnecessary stress. From Social Security taxation to IRMAA surcharges, Keith explains how to spot — and avoid — the hidden tax bites that come from well-intentioned decisions. You’ll learn: • How the “stacking rule” for income determines whether your capital gains are taxed at 0%, ...
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Retirement isn’t just about what you earn — it’s about what you keep. In this episode of That Financial Guy Show, Keith Wilson breaks down the overlooked tax traps that quietly drain retiree income and create unnecessary stress. From Social Security taxation to IRMAA surcharges, Keith explains how to spot — and avoid — the hidden tax bites that come from well-intentioned decisions. You’ll learn: • How the “stacking rule” for income determines whether your capital gains are taxed at 0%, ...
Are Roth Conversions Overrated? Real Stories You Need to Hear
That Financial Guy
19 minutes
2 months ago
Are Roth Conversions Overrated? Real Stories You Need to Hear
Everywhere you turn these days, people are talking about Roth conversions like they’re the ultimate retirement hack. But from what I’ve seen in working with real families, the truth is… Roth conversions can be overrated. In this episode of That Financial Guy Show, I share real stories from my own clients — times when a Roth conversion made sense, and times when it would have been a costly mistake. You’ll hear about: A client who almost converted in his peak earning years (and why that would’v...
That Financial Guy
Retirement isn’t just about what you earn — it’s about what you keep. In this episode of That Financial Guy Show, Keith Wilson breaks down the overlooked tax traps that quietly drain retiree income and create unnecessary stress. From Social Security taxation to IRMAA surcharges, Keith explains how to spot — and avoid — the hidden tax bites that come from well-intentioned decisions. You’ll learn: • How the “stacking rule” for income determines whether your capital gains are taxed at 0%, ...
