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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

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 finance, cash flow, and legacy planning. Join us for a holiday-themed deep dive on this week’s Check Your ...

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, or are you just running faster on a much bigger treadmill? Tune in to find out! Send us a text Send y...

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 a text 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 idea and deliver our verdict on whether a daily approach could finally be the breakthrough your budget needs. ...

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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

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 a text 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 65. Is it possible to be too focused on saving for your golden years? #retirement #financialplanning #balance Send us a text Send your ques...

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 a text 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 breakdown of the things you need to know right now! Send us a text Send your questions for upco...

Is the grueling pace of your job fueling your desire for FIRE (Financial Independence, Retire Early)? 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 freedom doesn't cost you your current well-being. Stop letting the corporate grind dictate your financial pl...

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 planning for the future, this episode is packed with must-hear, actionable lessons on maximizing your home's ...

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 prepare. Plus, we open the mailbag to answer listener questions on all things Roth. Send us a text Sen...

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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram

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 a text Send your questions for upcoming show to checkyourbalances@outlook.com @checkyourbalances on Instagram