The Retirement Reality Report

What can one of baseball’s biggest contracts teach you about retirement taxes? Using Shohei Ohtani's deferred compensation strategy as a starting point, David Linsky explains how timing income, managing distributions, and understanding tax rules can impact retirement planning. The discussion covers IRA withdrawals, Roth conversions, capital gains strategies, and why tax planning may be one of the most overlooked parts of a re...

Is the next hot investment opportunity worth the risk when you're nearing retirement? In this episode, Marc and Dylan Linsky discuss the excitement surrounding high-profile investments like SpaceX and why retirees should view speculative opportunities within the context of a broader financial plan. They explain the importance of balancing income needs, tax planning, protected assets, and long-term growth before chasing the latest m...

What happens if market volatility hits right when you start taking income in retirement? David Linsky discusses concerns around a potential market bubble and how it may affect those entering retirement. He explains why relying on traditional allocation strategies can create challenges during the distribution phase and highlight the importance of structuring income ahead of time. The conversation focuses on liquidity planning, avoid...

Is going all-in on Roth always the right move—or could it limit your flexibility later? David Linsky breaks down the growing conversation around Roth contributions and conversions, explaining why a one-size-fits-all approach may not apply. He explores factors like current and future tax rates, income changes, employer plans, and retirement timelines that can influence the decision. Plus, they discuss how to evaluate financial...

Is investor FOMO driving the market higher—and what could that mean for your retirement? In this episode, Marc and Dylan Linsky explore how a “melt-up” fueled by fear of missing out can impact long-term planning. They discuss the role of protection within a portfolio, how strategies shift from accumulation to retirement income, and why balancing growth with stability becomes more important as retirement approaches...

Why do so many investors repeat the same mistakes—even when they know better? In this episode, Marc and Dylan Linsky explore how emotions and behavior can influence financial decisions, especially during market volatility. The conversation focuses on shifting from trying to change habits to building discipline, using a structured financial plan as a guide. They also discuss balancing growth, income, and protection, while assi...

Why is it so hard to spend the money you spent decades saving? This episode explores the emotional and financial shift from accumulation to distribution in retirement. Marc and Dylan Linsky discuss why many retirees struggle to turn savings into income and how relying on accumulation strategies alone can create challenges. The conversation highlights the importance of having a structured system for withdrawals, managing market vola...

Is your 401(k) built for retirement—or just for saving? In this episode, Dylan Linsky explores how 401(k)s became a primary retirement tool and where they may fall short when it’s time to generate income. He discusses the difference between accumulation and distribution, why limited investment options can create challenges, and how strategies can shift after leaving the workforce. The conversation also highlights the im...

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 on market conditions. The discussion highlights the shift from saving to taking income, why distribution strategies matter, and how min...

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. They explain how Medicare premiums are calculated, share a real-life example of unintended tax outcomes, and highlight the...

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 Treasury remains elevated, how protected growth fits into a retirement plan, and the key differences between fixed and varia...

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, they break down how timing, dollar amounts, and overlooked thresholds like IRMAA can significantly change outcomes. The discussion h...

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‑world examples, they explain the difference between phase one (accumulation) and phase two (distribution) planning, why liquidit...

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 unnecessary stress. The conversation explores spending plans versus budgets, managing income gaps, liquidity needs, taxation of income s...

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 examples, Marc and Dylan Linsky break down how to check credentials, spot red flags, and understand the difference between planning-bas...

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 already in retirement. They discuss dollar-cost averaging, shifting from accumulation to distribution, and how reinvesting interest and ...

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 retirement and required minimum distributions matter, how Medicare IRMAA can complicate tax moves, and why popular strategies don’t...

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 in retirement, and the risks of selling investments at the wrong time. Through real‑world examples, the conversation highlights h...

Assumptions feel harmless—until retirement puts them to the test. In this episode, Dylan and David Linsky break down the common beliefs people hold about longevity, expenses, taxes, inflation, and income planning, and why those assumptions often miss reality. The conversation explores why expenses can rise after work ends, how time gets spent differently in retirement, and why phase‑two planning requires a different approach ...