Are the Golden Handcuffs Keeping You From Retirement?

Are the “golden handcuffs” keeping you from feeling ready for retirement? On this episode, Marc and Dylan Linsky discuss the moment many retirees experience financial clarity and confidence in their retirement plan. They explore how understanding income sources, expenses, taxes, and investment role…

What Can Shohei Ohtani Teach You About Retirement Taxes?

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…

Should Retirees Chase the Next Big Investment?

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.…

What If the Market Drops in Retirement?

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 di…

Should You Go All-In on Roth—or Think Twice?

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, inco…

Is FOMO Fueling a Market Melt-Up?

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 accu…

Why Smart Investors Still Repeat the Same Mistakes

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 buildin…

Why Spending in Retirement Feels So Difficult

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 alo…

Is Your 401(k) Failing You in Retirement?

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 opti…

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…