The Wise Money Show™

Retiring before Medicare? You might face a tricky balancing act between doing Roth conversions and keeping your health insurance subsidies through the Affordable Care Act (ACA). Tanner Watson, CFP®, helps us unpack a real-life retirement planning case to show how Roth conversions can impact your premium tax credits and what strategies can help you make the most of both.

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Retiring with debt in your 50s can feel like a dead end, but it doesn't have to be. In this episode of Wise Money, we unpack how to balance paying off debt while still making that final push toward a confident retirement. We explain different versions of the debt snowball, how to build a five-factor retirement plan, and how to bring clarity to your financial plan so you can retire with confidence. 

Season 11, Episode 13

When you retire, your investment strategy shouldn't look the same as it did during your working years. The way down the mountain is different and more challenging than the climb up. In this episode of Wise Money, we're walking through five retirement investment strategies, explaining the pros and cons of each, and helping you determine which approach is best for your situation. From dividend investing to the personal pension plan, ...

As 2025 wraps up, so does your chance to make smart, proactive tax moves before the year is over. In this episode of Wise Money, we walk through your 2025 fall tax planning playbook and checklist for you to follow. We cover Roth conversions, RMDs and QCDs, topping off Health Savings Accounts (HSAs), and how the tax law changes passed this summer should shape what you do before year-end.

Season 11, Episode 11

On this special Listener Question episode of Wise Money, we're answering your financial questions. From the new catch-up contribution rules and "super" catch-ups at age 60, to whether it ever makes sense to invest your 401(k) in individual stocks like Tesla or Palantir. We're unpacking most of the most confusing tax and retirement changes heading into 2026. 

Season 11, Episode 10

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Many people believe that earning more income will automatically lead to wealth, but that's not how financial freedom works. Real wealth isn't about how much you make, it's about how much you keep and what you do with it. In this episode of Wise Money, we are sharing practical ways to boost your savings, no matter your income level.

Season 11, Episode 9

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When it comes to Social Security, everyone has an opinion, but what does the math (and financial planning) actually say? We searched our YouTube comments to respond to your most common frustrations and misconceptions about Social Security. From "I don't want to spend down my own money first" to "I'll just invest my Social Security checks," we unpack the truth behind listener questions and comments. 

Most people have heard that Roth IRAs can be a powerful tool, but many don't realize that the timing of a Roth conversion is just as important as the strategy itself. If done right, a Roth conversion can save you thousands of dollars in taxes and help you build long-term, tax-free retirement income. In today's episode of Wise Money, we're breaking down the top five times when you should consider doing a Roth conversion. 

Season 11,...

Medicare is going through some of the biggest changes we've seen in years, and the impact on your retirement planning could be significant. Premiums for Medicare supplement prescription drug plans are expected to rise sharply, and the way you budget for healthcare in retirement may need to shift. In this episode of Wise Money, we break down what these changes mean, why costs are increasing, and how you can prepare.

Season 11, Episo...

Are you in your 50s and planning for retirement? This decade can make or break your financial future. From cashing out retirement accounts too early to overlooking critical tax strategies, these mistakes can quietly derail your retirement goals. In this episode, we're revealing the top seven costly money mistakes people commonly make in their 50s and how you can avoid them.

Season 11, Episode 6

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Should you keep life insurance once you retire, or is it time to drop it? In this episode of the Wise Money Show, we reveal when life insurance still makes sense in retirement, when it doesn't, and how to make the best decision for your financial future. Whether you're still working, planning retirement, or already retired, understanding how life insurance fits (or doesn't fit) into your financial plan is essential. 

Season 11, Epi...

Losing a spouse is one of the most difficult transitions in life, emotionally and financially. We're sitting down with Tayler Rhoda CFP® to discuss the unique financial challenges widows and widowers face, especially in retirement.

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Major tax law changes are here in 2025. Are you ready to take advantage of them before year-end? In this episode of Wise Money, we break down the most important updates from the Secure Act 2.0 and One Big Beautiful Bill Act (OBBBA) and show you how to proactively plan so you pay the least amount of tax over your lifetime. We cover the increase of the SALT cap from $10,000 to $40,000, how the new senior deduction works, the truth ab...

College planning doesn't have to break the bank. From 529 plans and tax credits to student loans and smart money habits, this episode of the Wise Money Show walks you through practical strategies to help families save for education, reduce student debt, and set students up for lifelong financial success. 

Season 11, Episode 3

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Thinking about tapping into your retirement accounts to buy a home or cover a big move? In this episode of Wise Money, we break down the pros and cons of using IRA or Roth IRA funds for non-retirement needs like down payments or relocation costs. We'll also answer listener questions on Roth conversions later in life, inherited IRA planning, and the five-year rule on Roth withdrawals.

Season 11, Episode 2

Think you know taxes? Think again. In this episode of Wise Money, we uncover the most common tax misconceptions that could be hurting your financial plan. From mortgage interest myths to the truth about 401(k) contributions and gifting rules, we break down what's fact and what's fiction so you can keep more of your hard-earned dollars.

Season 11, Episode 1

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Should you invest your HSA (Health Savings Account), and if so, how do you actually do it? In this episode of Wise Money, we're answering listener questions on some of the most important areas of your financial life. We kick things off with one of the most common questions we receive: Should you invest your HSA, and if so, how? We'll explain what a Health Savings account is, why it's such a powerful tool, and who should (and should...

Selling your business isn't just about the top-line sale price; it's about how much you actually get to keep after taxes, debt payoff, and transition costs. In this Wise Money Spotlight, CFP®, CEPA Jared Moxness joins Mike to unpack the essentials of business exit planning. We cover when to start planning, how to prepare your business and yourself for the transition, the most common ways to sell, tax-efficient strategies to keep mo...

Is $1 million enough to retire? It's a question nearly every saver has wondered, and the answer might surprise you. In this episode of Wise Money, we dig into the $1 million retirement goal. What does being a "millionaire" actually mean today? Can you stop saving once you hit that milestone? And how do spending, lifestyle, and longevity factor into your ability to retire confidently? We'll walk through the five key factors that det...