Check Your Balances

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.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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?Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 joined by Simon Erickson, founder of 7Investing and one of the most forward-looking minds in growth investing. Simon helps us break down whether the recent $1 trillion sell-off in software stocks is a permanent structural shift or the ultimate "buy the dip" opportunity.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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't just another episode; it’s an interactive event dedicated to the community that has grown alongside us.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 premium tax software offers genuine value or if you're better off with a less expensive option - and how to evaluate them. Whether you're weighing a new job offer or optimizing your retirement bucket, this episode provides the framework for making smarter money moves this spring.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 math of eroding buying power, we reveal why time is the ultimate lever for the borrower—and how you can use a fixed-rate mindset to short the dollar and build long-term wealth.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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’re diving into the specific scenarios where paying the penalty might actually be the most logical—or least destructive—financial move available to you.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 begins to outpace your contributions. By staying consistent through the heavy lifting, you allow your wealth to transform from a stationary pile into a self-sustaining engine.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 Beautiful Bill" you’ll face in April.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 problem that doesn't exist. Whether it’s the over-glamorized world of property management or the fear-based selling of insurance products, we’re here to help you spot the red flags before you sign a contract. Tune in for a dose of much-needed skepticism and a reality check on our favorite financial punching bags.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 "disappearance" of affordable housing.In an environment where the "market" and the "economy" are moving in different directions, how should you be positioning your portfolio?Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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" for retirement cash flow. That and more on this week's episode!Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 MailSend your questions for upcoming show to [email protected] @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 Balances!Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 VanguardSend us Fan MailSend your questions for upcoming show to [email protected] @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. Tune in this week for our take!Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 MailSend your questions for upcoming show to [email protected] @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 Fan MailSend your questions for upcoming show to [email protected] @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 Fan MailSend your questions for upcoming show to [email protected] @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 #balanceSend us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 MailSend your questions for upcoming show to [email protected] @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 Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 plan—it's time to find a path to independence that's sustainable.#FIREMovement #Burnout #FinancialIndependence #CheckYourBalances #CoastFIRESend us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 sale price and minimizing costly mistakes.#RealEstate #personalfinance #Investing #HomeSale #PropertyInvestment #WealthBuildingSend us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 MailSend your questions for upcoming show to [email protected] @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 Fan MailSend your questions for upcoming show to [email protected] @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 Fan MailSend your questions for upcoming show to [email protected] @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 Fan MailSend your questions for upcoming show to [email protected] @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 Fan MailSend your questions for upcoming show to [email protected] @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 Fan MailSend your questions for upcoming show to [email protected] @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 inherited IRA. We'll break down the key rules, including the 10-year rule, and discuss how to create a strategy that works for you.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

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 you need to understand exactly how this legislation impacts your individual finances. Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

In this episode of Check Your Balances, we're joined by Callum Thomas to tackle a crucial question for your portfolio: Do you own enough emerging markets? Callum shares his expert insights on the current landscape, potential, and risks of investing in these dynamic economies. Tune in to understand if your asset allocation is truly optimized for global growth.Learn more about Callum at Top Down Charts and The Weekly ChartStormSend us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

This week, NerdWallet's Sara Rathner makes a second appearance on the show to talk about the changes to the Chase Sapphire Reserve card. As one of the most prominent travel cards and the market, and one that Ross happens to personally use... this was of particular interest. Sara Rathner is a NerdWallet travel and credit cards expert. She has appeared on the “Today” show and CNBC’s “Nightly Business Report,” and has been quoted in The New York Times, The Washington Post, The Wall Street Journal, Yahoo Finance, Time, Reuters, NBC News, Business Insider and MarketWatch. Learn more about her work here: https://www.nerdwallet.com/author/sara-rathnerSend us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

On this week's episode of Check Your Balances, a mailbag episode! Does Chat GPT know how each of your retirement account taxes actually works? How do the fees in mutual funds and ETFs actually get deducted? These questions and more as we dive into what our listeners want to hear us talk about.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

What can the hit Apple TV show Severance teach the fellas about saving for financial independence? Join us this week as Ross and Dan explore the idea that you might be "severed" from the version of yourself that you're supposed to be saving money for. Wishing everyone a safe and happy 4th of July!Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

How do you you get your money to line up with being available when you actually need it? Designing a portfolio with this strategy in mind is called "Liability Matching" and it's a concept that Ross and Dan believe in and teach regularly. While rules of thumb like "The 4% Rule" get all the buzz, this is how to think about actually connecting your money with its purpose.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

Think you know the average American? Ross and Dan are about to find out if they do! Welcome to "Over Under," the brand new game on Check Your Balances where our hosts put their statistical savvy to the test. They'll compete in a lighthearted game to see how well they know the wealth and financial habits of the typical American.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

A surge in homes for sale relative to the number of buyers leads Ross to question whether his purchase of a home 6 months ago might have been poorly timed. Is he the worlds worst real estate investor? Only time will tell, but you can hear the boys discuss it on this weeks episode of Check Your Balances.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram

This week on Check Your Balances, we tackle a listener question: Should your Roth IRA double as an emergency fund? We'll explore the pros and cons. We'll also demystify the critical difference between correlation and causation in personal finance. Understanding this distinction is key to making sound financial decisions, ensuring you build a robust financial plan based on true cause-and-effect, not just coincidental relationships.Send us Fan MailSend your questions for upcoming show to [email protected] @checkyourbalances on Instagram