Same Savings, Different Outcomes: Timing’s Role in Retirement

What happens when retirement begins at the wrong time in the market? In this episode, David Linsky explores how timing and sequence of returns can impact retirement outcomes. Using real-world examples, he compares how two retirees with similar savings can experience very different results depending…

The Hidden Tax Trap That Can Raise Your Medicare Costs

What if a small withdrawal could quietly trigger a chain reaction of taxes and higher Medicare costs? In this episode, Marc and Dylan Linsky break down how IRMAA surcharges can impact retirement and why income decisions—from selling a home to taking IRA withdrawals—can have broader tax consequences…

Why High Interest Rates May Open a New Retirement Window

Are higher interest rates actually creating opportunities retirees shouldn’t ignore? In this episode, Marc and Dylan Linsky discuss how today’s rate environment is reshaping conversations around fixed income, including CDs, bonds, money markets, and fixed annuities. They break down why the 10-year …

When a Roth Conversion Can Create an Unexpected Tax Problem

A Roth conversion can look smart on paper—but done at the wrong time, it can quietly raise your tax bill. In this episode, David and Dylan Linsky explain why Roth conversions require careful coordination with retirement income, tax brackets, and Medicare premium rules. Using real‑world examples, th…

What Market Volatility Reveals About Retirement Income Planning

When markets are volatile, the way your retirement income is structured matters more than ever. In this episode, Marc and David Linsky break down how different income sources, investment “buckets,” and purposeful asset allocation can work together in retirement. Using simple analogies and real‑worl…

Why the First Year of Retirement Sets the Tone

Most people plan harder for vacations than they do for retirement—and that mindset shows up fast once the paychecks stop. In this episode, Marc and Dylan LInsky break down why the first years of retirement are so critical and how spending habits, income gaps, and lack of structure can create unnece…

How to Avoid Fake Financial Advice Online

Anyone can look like a financial expert online—but how do you know who to trust with your retirement savings? In this episode, the conversation centers on how retirees can protect themselves from misleading advice and unqualified influencers posing as financial professionals. Using real-world examp…

AI, Market Volatility, and Retirement: What Changes—and What Doesn’t

Market volatility, AI headlines, and nonstop uncertainty can make retirement planning feel like a constant balancing act. In this episode, Dylan and David Linsky unpack how disruptive trends like artificial intelligence fit into a long-term investment approach—especially for those nearing or alread…

The Retirement Windows You Don’t Want to Miss

Miss a retirement window, and the opportunity may be gone for good. In this episode, David Linsky breaks down key ages and timing decisions that can shape retirement outcomes, from pension elections to IRA rollovers and Roth conversion strategies. The conversation highlights why the years between r…

Political Risk and the Retirement Income Problem

When headlines move markets overnight, how should retirees think about political risk? David and Dylan Linsky unpack how sudden political events can impact retirement portfolios—and why distribution strategy matters more than allocation alone. The episode explores market volatility, income planning…