Check Your Balances

Latest Episodes:

SpaceX: A Rocket You Want to Ride? Jun 10, 2026

Show notes

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 actually qualify for the S&P 500? And should you be rushing to buy shares on day one, or watching from a safe distance?
We break down the mechanics of a landmark market event and share our personal game plans for the biggest IPO in history.

Send us Fan Mail

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

Is the Coffee Really Blowing Your Budget? Jun 03, 2026

Show notes

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 almost never your morning caffeine fix.

Tune in to find out if we can find a more thoughtful way to teach young investors the impact of a creating financial discipline.

Link to Article: What Wealth Managers Teach About Avoiding Spending Traps via Business Insider (https://www.businessinsider.com/teach-wealth-management-avoid-these-spending-traps-save-money-invest-2026-5)

Send us Fan Mail

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

Is the Berkshire Shareholder Letter Still Required Reading? May 27, 2026

Show notes

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?

This week Ross and Dan break down Greg Abel's first letter and whether it still deserves a spot on your reading pile.

Send us Fan Mail

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

How Easy Is the Rule of 55 to Use? - Mailbag Episode May 20, 2026

Show notes

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) penalty-free before the magical age of 59½. But is it actually as simple as it sounds? We look at the fine print, the common traps people fall into, and why your employer’s specific plan documents hold all the power.

We later transition from tax code to relationship dynamics. How much can you or your spouse spend without asking for permission? We discuss how to establish "no-questions-asked" spending limits, and whether a wheel of cheese could actually be a good investment.

Send us Fan Mail

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

1929: Is This Our Past or Our Future? May 13, 2026

Show notes

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 Mail

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

Are You Feeding AI Financial Plans Bad Assumptions? May 06, 2026

Show notes

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 Mail

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

What Companies Do We Hold Grudges Against? Apr 29, 2026

Show notes

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 Instagram

Did Vanguard Come up with a BETR Approach for Roth Conversions? Apr 22, 2026

Show notes

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 Mail

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

Is Your Retirement Carve Out Long Enough? Apr 15, 2026

Show notes

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 Mail

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

Does Your Money Need Spring Cleaning? Apr 08, 2026

Show notes

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 Mail

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

Our TOPPODCAST Picks

Follow Us

Stay Connected

Related Podcasts

Links

Stay Connected