Check Your Balances

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 sensitiv...

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? Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagra...

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 r...

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...

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...

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. Send us Fan Mail Send your questions for upco...

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 your...

If you feel like the ground is shifting under your feet as a tech investor, you aren’t alone. Early 2026 has introduced a new term to the financial lexicon: the SAASpocalypse . With AI agents beginning to perform tasks that used to require a $50-per-seat software subscription, the traditional "moats" of the software-as-a-service world are being tested like never before. This week, we are...

If you've got mutual funds in your portfolio you might be familiar with that uncomfortable feeling at tax-time when your CPA sends you a bill even when you didn't sell anything. We talk about how to anticipate and navigate capital gains distributions on a mutual fund, and also weigh in on whether its the right time to refinance a high rate mortgage. Send us Fan Mail Send your questions f...

It’s hard to believe it’s been half a decade since we first hit "record" to talk shop about markets, financial planning, and the psychology of money. To celebrate our 5th Anniversary , we’re stepping out from behind the microphones and into the room with the people who made it all possible: You. Join Ross and Dan for a special live taping of the Check Your Balances podcast! This isn&apos...

In mailbag episode of Check Your Balances , we break down the financial reality of choosing between 1099 and W2 employment. Do the additional deductions actually make this a way better deal? We also tackle the Roth IRA debate of whether you should swing for the fences with high-growth stocks or play the long game with broad-market index funds. Finally, we tackle tax season head-on by evaluating if...

If you could borrow money for a century, should you? This episode explores the strategy behind Alphabet's 100-year bond and why one of the world's wealthiest companies chooses to stay in debt until the next century. We bridge the gap between corporate finance and your front door, breaking down how inflation acts as a "discount" on long-term debt like mortgages. By analyzing the...

It’s the ultimate "break glass in case of emergency" move: tapping into your 401(k) or IRA before you hit age 59½. Usually, the advice is a resounding "don't do it," thanks to that stinging 10% early withdrawal penalty plus ordinary income taxes. But life rarely follows a linear spreadsheet. In this episode, we tackle the nuance of the "forbidden" withdrawal. We’...

Staring at a driveway buried by a snowstorm is a lot like looking at a massive financial goal—overwhelming until you start chipping away. This episode of Check Your Balances explores how small, "baby steps" eventually lead to a critical inflection point where momentum takes over. We discuss the transition from the "grind" of active saving to the moment your portfolio’s growth b...

Tax season is a different beast under the One Big Beautiful Bill (OBBB), and it’s time to see if your strategy holds up. This week, we’re joined by Ryan Flanigan, CPA, to break down the legislative shifts and what they mean for your bottom line. From permanent bonus depreciation to the new incentive structures, we’re cutting through the noise to make sure you’re prepared for the "Big Beautifu...

Finding overstated benefits in real estate and annuities might just be our favorite pastime. This week on Check Your Balances, Ross and Dan are putting on the gloves to take down the myths and math of these two common financial tropes. The rant gets specific as we highlight the absurdity of pitching annuities to investors who already enjoy the security of a strong pension—essentially solving a pro...

The K-shaped economy is a jarring reality right now. On the "upward" arm, you have households with significant exposure to assets like stocks and real estate—which have reached record highs—alongside industries like AI and tech that are booming. On the "downward" arm, you have those feeling the squeeze of high interest rates, stagnant wages relative to costs, and the "disa...

Is there a "magic bullet" for generating tax-free income in retirement? This week, Ross and Dan dive back into the mailbag to tackle a question that sounds almost too good to be true: The Tax-Free Dividend Roth Strategy. We’ve all heard that Roth IRAs are powerful, but a listener asks if specifically loading a Roth with high-yield dividend stocks is the ultimate "cheat code" fo...

As we close out 2025, Ross and Dan look back at a year that defied the scripts, from "sure-thing" predictions that fizzled to the market moves that caught even the pros off guard. Join us for a final look at the lessons of 2025 and a clear-eyed strategy for your money as we head into 2026. Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourb...

Which holiday icon would be a financial advisor’s worst nightmare? This week, we’re putting Christmas characters under the microscope. We debate whether the Grinch or Scrooge is the tougher client to manage and dive into the 'North Pole Economics' of how Santa actually funds his global operation. Beyond the festive fun, we explore what these fictional portfolios teach us about behavioral...

Could a $100 million career income actually be insufficient for true, lasting generational wealth? This week, Ross and Dan dive deep into the ultimate financial paradox: the hidden, massive costs of being ultra-wealthy. We unpack the eye-opening comments from NFL star Odell Beckham Jr. about how quickly a pro athlete's money evaporates. At this level, do standard retirement rules still apply,...

In a world where cash is yielding around 4% and the bond index has lost 0.35% over the last 5 years*... why would you buy bonds instead of sitting on cash? This week we dive into that question and several others from our Mailbag. * Data as of 11/30/2025 via Vanguard Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

We've always championed the long-term view of budgeting, but what if thinking about your money daily is the real secret to financial control? This week, we explore the idea of micro-timeframe spending: Is hyper-focusing on every 24 hours empowering and key to hitting your goals, or is it a recipe for driving yourself completely nuts? We'll reveal how we came to this counter-intuitive ide...

We celebrate Thanksgiving with some light hearted banter, and exploring the question of whether "High Watermarking" can lead to disappointment (even if it's hypothetical). We hope you're enjoying time with your family and friends this week, but if you want your weekly dose of personal finance content, we're here for you! Send us Fan Mail Send your questions for upcoming sh...

Could a half-century loan be the answer to the housing crisis, or is it a financial nightmare waiting to happen? We break down the pros, cons, and the brutal amortization schedules of 50-year mortgages to see who actually benefits. Plus, we’re emptying the mailbag to cover the specific financial hurdles you are facing right now. Tune in to this week's mailbag episode! Send us Fan Mail Send yo...