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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.
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Recent Episodes
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…
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…
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…
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…
Are You Underestimating the Impact of Baby Steps?
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…
Are Your Taxes Ready for the OBBB With Ryan Flanigan, CPA
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…
Are Annuities and Real Estate Our Favorite Punching Bags?
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…
Investing in a K Shaped Economy
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…
Does a tax free dividend Roth work? - Mailbag Episode
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…
So Long 2025 from CYB!
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…
Would The Grinch be the worst client?
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…
Is $100 Million Enough for Generational Wealth?
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…
Why buy bonds when cash looks better? - Mailbag Episode
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…
Daily Budgeting: Sanity or Stress?
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…
Does High Watermarking turn progress into disappointment?
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…
Does a 50 Year Mortgage Make Sense? - Mailbag Episode
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…
How Would You Invest $100K Without the Stock Market?
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…
Is the Financial Plan Too Focused on Retirement?
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…
How Spooky Is This Market?
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…
October Mailbag: College Planning, Dollar Cost Averaging Out, Scams!
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…
Frequently Asked Questions
Check Your Balances has published 262 episodes since February 2021, covering topics in Business, Education.
Check Your Balances is currently highly active with new episodes weekly. Average episode length is 27m.
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