Check Your Balances
Managing your money doesn't have to be boring. Check Your Balances is your weekly financial co-pilot, hosted by two experienced financial planners. We deliver straight-talk strategies and expert-level advice to help you save, invest, and finally feel 100% in control on your journey to financial independence.
Episodes
283 episodes
The Discipline Myth: How to Engineer Better Financial Choices
Most people who seem to have incredible financial discipline don’t actually possess superhuman willpower. Instead, they’ve just built environment-driven systems that eliminate temptation altogether. In this episode, Ross and Dan break down why ...
Would You Rather? From Practical to Absurd
Financial decisions are really just a series of trade-offs—some straightforward, others a little unhinged.This week on Check Your Balances, Ross Anderson, CFP® and Daniel Messeca, CFP® turn financial planning into a game of "Would You R...
Are You Making These 401(k) Errors? From NUA to Default Funds
Your 401(k) is likely your largest retirement asset, but are you managing it with a blind spot? This week, we cover the spectrum of 401(k) mistakes, starting with the heaviest hitter: Net Unrealized Appreciation (NUA). We explain how thi...
The Quiet Capital Drain: Could Coast FIRE Break the System?
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 Illusion of Diversification & Your Summer Mailbag Questions
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...
Should You Consider a Franchise? with Jon Ostenson
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 power...
Birthdays, Babies, and Big Moves: Dan’s Year in Review
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:...
SpaceX: A Rocket You Want to Ride?
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 t...
Is the Coffee Really Blowing Your Budget?
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...
Is the Berkshire Shareholder Letter Still Required Reading?
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 readin...
How Easy Is the Rule of 55 to Use? - Mailbag Episode
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 t...
1929: Is This Our Past or Our Future?
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 historica...
Are You Feeding AI Financial Plans Bad Assumptions?
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 f...
What Companies Do We Hold Grudges Against?
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 wr...
Did Vanguard Come up with a BETR Approach for Roth Conversions?
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 ...
Is Your Retirement Carve Out Long Enough?
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...
Does Your Money Need Spring Cleaning?
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" ch...
What Might Bust Your Bracket?
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 situ...
The March Mailbag: From Scarcity Mindsets to Roth Nuance
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 surro...
SAASpocalypse, Quantum, and AI investing with Simon Erickson
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 requir...
Capital Gains and Refinances, Our favorite topics?
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 distrib...
Celebrating 5 Years with a Live Listener Event
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 in...
1099 vs W2 Jobs & More: February Mailbag
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...
If you could borrow money for 100 years, should you?
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 bet...
When Does It Make Sense to Pay Retirement Account Penalties?
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 taxe...