Roth Conversions for High Earners: Timing, Taxes, and Long-Term Control (Ep. 23)

Roth Conversions for High Earners: Timing, Taxes, and Long-Term Control (Ep. 23)

Retirement tax decisions often feel simple on the surface, but the ripple effects can last decades. The real question is not whether taxes will be paid, but when, how, and by whom. In this episode, Dan Reese, CFP®, walks through how Roth conversions, a taxable event, can fit into a broader retirement and estate plan …

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Are Business Owners Ready for the $14 Trillion Exit Wave? (Ep. 22)

Are Business Owners Ready for the $14 Trillion Exit Wave? (Ep. 22)

Most business owners say they feel prepared to step away, but available data suggests gaps in readiness. In this episode, Dan Reese breaks down insights from the National State of Owner Readiness Report and explains common areas where small and mid-sized business owners may lack preparation for a significant financial transition. With a large portion …

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The Risk of Following TikTok Finance (Ep. 21)

The Risk of Following TikTok Finance (Ep. 21)

Online platforms surface a steady stream of financial content, often from influencers whose guidance is not tailored to individual situations. In this episode of Ramp Up to Retirement, Dan Reese discusses the difference between broad online commentary and fiduciary planning, and how that gap can affect real retirement decisions. He walks through examples involving Roth …

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The $150,000 Gift That Derailed Their Retirement with Brent Oliver (Ep. 19)

The $150,000 Gift That Derailed Their Retirement with Brent Oliver (Ep. 19)

Mark and Susan thought they did everything right: no debt, over a million saved, markets trending up. But one well-intentioned gift to their kids set off a chain of financial consequences they didn’t anticipate. In this episode, Dan Reese is joined by Brent Oliver for a hypothetical case study exploring how using the concept of …

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The $1 Mistake That Could Cost You Thousands in Retirement (Ep. 18)

The $1 Mistake That Could Cost You Thousands in Retirement (Ep. 18)

Did you know that even one extra dollar of income in retirement may trigger higher taxes, Medicare premiums, or health insurance costs? This week, Dan Reese explains common retirement planning situations where a single extra dollar in income can unexpectedly spike your taxes, Medicare premiums, and insurance costs. From IRMAA surcharges to Social Security taxation …

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The Danger of Not Knowing What You Don’t Know (Ep. 17)

The Danger of Not Knowing What You Don’t Know (Ep. 17)

One of the biggest risks to your retirement may not be the market. It could be overconfidence. Dan Reese examines the genuine risks of DIY financial planning, particularly in a world inundated with AI tools and financial influencers who oversimplify complex decisions. From emotional investing to overlooked tax landmines and Medicare surprises, Dan breaks down …

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You’ve Retired. Now What? The Hardest Financial Shift You’ll Ever Make (Ep. 16)

You’ve Retired. Now What? The Hardest Financial Shift You’ll Ever Make (Ep. 16)

Most people think the hard part is saving for retirement, but the real challenge begins when the paychecks stop. Dan Reese walks through the crucial mental and financial shift from accumulation to decumulation and why so many retirees get it wrong. From tax surprises and market volatility to emotional roadblocks and overlooked estate planning, Dan …

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One Big Beautiful Bill: Tax Changes Every Retiree Needs to Know with Brent Oliver (Ep. 15)

One Big Beautiful Bill: Tax Changes Every Retiree Needs to Know with Brent Oliver (Ep. 15)

Retirement planning doesn’t exist in a vacuum, especially when tax laws are shifting.  Dan Reese and guest Brent Oliver, Senior Wealth Advisor at Avery Wealth, break down the latest tax legislation and what it means for your future income, charitable giving, and estate plans. From the extension of lower tax brackets to the expanded standard …

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Social Security Myths That May Derail Your Retirement Strategy (Ep. 14)

Social Security Myths That May Derail Your Retirement Strategy (Ep. 14)

Many people feel confident about Social Security until it’s time to file. That’s when the conflicting advice from neighbors, social media, and self-proclaimed experts can make a complex decision even harder.  In this episode, Dan Reese, CFP®, breaks down the most common Social Security myths and explains how decisions around claiming, spousal benefits, and timing …

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