Check Your Balances

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...

This week, Ross and Dan tackle a fun question... If you had to invest $100,000 without using the stock market, what would you do?  Would you become a landlord and try to buy real estate? Would you try to start a business or invest in something truly "passive?" Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

Does the average financial plan have "retirement tunnel vision," with a focus on pouring every spare dollar into your retirement accounts. We're all told to save for the future, but what happens when that focus makes us 'house poor' or 'life poor' today? Big goals like buying a home, funding college, or starting a business can't always wait until you're...

First up: A listener challenges our take on Dollar Cost Averaging out. Then, we confront the fear: How spooky is this market? Ross and Dan bust the financial ghouls and tell you what’s truly frightening for your portfolio (and what’s just noise). Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

The October Mailbag is here! Ross and Dan open up the mailbag to answer your pressing financial questions, tackling everything from navigating the costs of college to whether you can Dollar Cost Averaging (DCA) out of a position as you approach retirement. Plus, they dive into the latest listener stories and tips on spotting and avoiding financial scams . Tune in for practical advice and a breakdo...

Is the grueling pace of your job fueling your desire for FIRE ( F inancial I ndependence, R etire E arly)? This week on Check Your Balances , Ross and Dan tackle the reality that for many, burnout is the primary driver of the movement, not just aspiration. We discuss how to re-evaluate your aggressive savings strategy, explore more balanced options like Coast FIRE , and ensure your pursuit of free...

When it's time to sell your personal home, do you treat it like a purely emotional move or a smart financial transaction? This week, our resident real estate expert, Dan, is under contract on selling his personal home. Join us as Dan breaks down the process, from pre-listing prep and pricing strategy to staging secrets and negotiation tactics. Whether you're moving next month or just pla...

Your Catch-Up Contributions Are Changing! This week, Ross and Dan dive into the new guidance from the Treasury Department that will redefine how high earners over age 50 make their 401(k) catch-up contributions. The new rule mandates Roth contributions for certain savers, forcing many to lose a key pre-tax deduction. We break down who is affected, when this starts, and what you need to do to prepa...

30 Year Fixed Mortgage rates decline down to 6.26%, is it too early to consider a re-finance from a high rate loan? This week Ross and Dan unpack some of the trickery that can make you think you're saving more money than you really are when you look at refi numbers and how to make sure you don't get fooled. Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlo...

This week, Ross and Dan read and discuss The Millionaire Next Door. Does a finance book from 1996 still have precious lessons for us to learn about becoming Prodigious Accumulators of Wealth (PAWs) and avoiding the dreaded Under-Accumulator of Wealth (UAW) title? Tune in this week to see if this still deserves a spot on your shelf almost 30 years later. Send us Fan Mail Send your questions for upc...

As a follow up to last week's episode with David Gardner, we dive deeper into whether the Rule Breaker Investing philosophy is suited for an investor that is approaching retirement. Ross and Dan spent 6 years almost exclusively trying to answer that question for many many investors. Here's what they think about that concept today! Send us Fan Mail Send your questions for upcoming show to...

This week we are honored to have the Co-Founder and Chief Rule Breaker of The Motley Fool, David Gardner, join the show. David has an unbelievable investing track record, and his new book Rule Breaker Investing is his formula for success. We know many of our listeners are excited to hear David's thoughts! Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlook.com...

Got extra cash and wondering if you should throw it at your mortgage? 🤔 This week, we dive into the age-old debate: when does it actually make sense to overpay your mortgage? What are you using if you still mourn the loss of Mint.com? That and more in this week's mailbag episode. Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Ins...

When it comes to talking about finance, not all of the theories you hear out there are going to be winners. What are some of the dumbest theories that we've come across, and why are they wrong? Tune in to find out. Send us Fan Mail Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

Are you one of the many people who've inherited a retirement account and are now wondering, "What's an RMD and how do I manage it?" The rules around inherited IRAs and required minimum distributions have changed, and it can be confusing. In this episode of Check Your Balances, we're tackling the complex topic of managing Required Minimum Distributions (RMDs) on an inherite...

Scott Galloway recently announced he’s dropped all of his insurance—but is he an anomaly or onto something? Dan and Ross break down his controversial stance and discuss whether most people are actually over-insuring themselves against small risks. Tune in to find out if you're a Scott Galloway, or if you're just paying too much. Send us Fan Mail Send your questions for upcoming show to c...

The highly anticipated "One Big Beautiful Bill" has officially been signed into law, sparking intense debate and speculation. This week on Check Your Balances, we're cutting through the noise to deliver a crucial breakdown of its sweeping changes. From tax tweaks and investment implications to critical shifts in financial planning, we'll equip you with the essential insights yo...