In this episode of Check Your Balances, we dive deep into the haunting parallels between the modern financial landscape and the most infamous market collapse in history. We explore Andrew Ross Sorkin’s thoughtful insights and historical analysis surrounding the Great Crash of 1929.

Is a century of economic "progress" enough to save us from ourselves, or are we just 1929 investors with faster internet? Let's get into it.

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In financial planning, we often talk about "the numbers," but behind every projection lies a set of assumptions. Whether it’s an estimated rate of return, a projected inflation figure, or even how long you expect to live, these inputs are the foundation of your entire strategy. But what happens when you pull on a single thread?

This week on Check Your Balances, we dive into the sensitivity of financial plans. We discuss how making an assumption that feels conservative in one way can have completely unintended consequences, and vice versa. In a world where more people are turning to AI to ask their financial questions - can the wrong assumptions have a major impact for you?

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In this week's episode, Ross and Dan review the businesses that have wronged them. Whether that grudge is for the most petty thing ever, that's for you to decide. Do you have businesses that you simply won't work with again because they have wronged you in some way?

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In this episode, we’re digging into Vanguard’s 2025 BETR (Break-Even Tax Rate) Framework to see if it’s a legitimate breakthrough or just a fancy new acronym for the same old math. We explore whether this methodology actually simplifies the Roth conversion debate or if it just adds another layer of "analysis paralysis" for investors trying to outrun the IRS. Is pinpointing a break-even rate actually realistic, over-engineered, or not going far enough?

We’re breaking down the mechanics to see if Vanguard’s "gold standard" is a must-use tool. Tune in as we question whether this framework is truly better, or just better marketing.

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This week we re-examine our favorite strategy for making the transition into retirement, the "Carve Out." When transitioning into retirement, the safe asset bucket or "Carve Out" is often touted as the ultimate psychological safety net. But how much cash is actually enough to weather a prolonged market downturn without selling equities at a loss?

In this episode, we revisit the mechanics of the retirement carve out. Is 5 years the magic number? Whether you are five years out or already enjoying your golden years, we explore the strategies needed to ensure your liquidity matches your needs.

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As the seasons shift and the weather clears, it is the perfect time to open the windows, clear out the dust, and take a fresh look at your financial life. This week on Check Your Balances, we are diving into a comprehensive "Spring Cleaning" checklist for your money. Whether you are looking to simplify your accounts or maximize your savings rate, a little seasonal maintenance goes a long way toward long-term clarity.

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March madness isn't just for the court—sometimes, life throws a full-court press at your financial plan that you never saw coming. In this episode, we take a look at the "bracket busters" of personal finance: those unexpected or overlooked situations that can derail even the most carefully constructed strategy for financial independence.

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In this March mailbag episode, we’re diving into the listener inbox to tackle the psychological hurdle of oversaving and how to transition from a lifetime of hoarding to intentional spending. We also clear up the "sloppy" discourse surrounding Roth conversions, cutting through the noise to discuss the tax nuances and math that actually matter. Whether you're struggling to give yourself permission to spend or weighing a big tax move, we’re bringing some much-needed clarity to your financial plan.

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