Check Your Balances

For decades, standard capital markets assumptions have relied on a predictable, cyclical conveyor belt of capital: workers save, institutions invest, markets rise. But we might be staring down a massive, structural wrench in the gears. Between the Great Retirement of the Boomer generation and the cultural explosion of Coast FIRE—where millions of younger investors stop contributing to retirement e...

In this week's mailbag episode, we are diving straight into the listener inbox to tackle the financial questions on your mind. First up, we break down a fundamental investing trap: Portfolio Overlap . A listener asks how to actually tell if adding a new ETF to their portfolio provides true, independent diversification, or if they are just buying the same exact stocks under a different wrapper...

Corporate America isn't the only path to building wealth, but starting a business from scratch can feel like jumping without a parachute. This week, we sit down with top non-food franchise consultant and investor Jon Ostenson to explore a powerful alternative. If you think franchising is limited to fast-food burgers, think again. Jon breaks down why some of the best opportunities actually lie...

Happy Birthday, Dan! In this special episode, we’re celebrating another trip around the sun by taking a deep dive into Dan’s personal finances over the last 12 months. It’s been a whirlwind of a year defined by two of life’s biggest milestones: packing up and moving to a new home, and welcoming a beautiful new baby to the family. Join us as Dan opens up his own playbook to share the real-life fina...

SpaceX is days away from the largest IPO in history, and the ripple effects are going to hit every single investor. With a massive projected market cap, this launch could force index funds to aggressively dump shares of other tech giants just to make room for Elon Musk's aerospace behemoth. How do major indices protect portfolios from that kind of sudden systemic risk? When will SpaceX actual...

We’ve all been told that skipping your daily latte is the secret to building wealth. But is sacrificing small joys actually moving the needle, or is it just a distraction from the real culprits? In this episode of Check Your Balances, we unpack a recent Business Insider article on "Wealth Traps" to reveal what’s really holding people back from financial freedom. Spoiler alert: It’s almos...

For decades, Warren Buffett’s annual letter to Berkshire Hathaway shareholders was the ultimate textbook for value investing. Packed with folksy wisdom, sharp market critiques, and fundamental business truths, it was considered mandatory reading for anyone serious about finance. But with Greg Abel officially taking the helm as CEO , the landscape has shifted. Is the letter still worth your time? T...

It’s time to open up the mailbag! In this episode, Ross and Dan dive into your financial questions, tackling everything from early retirement strategies to the interpersonal dynamics of shared household finances. First up, we break down the Rule of 55 . If you’re looking to retire or step away from your job early, this IRS provision sounds like a dream—allowing you to tap into your current 401(k)...

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 f...

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...