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
263 episodes
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...
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Episode 268
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23:29
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...
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Episode 267
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32:51
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...
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Episode 266
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33:35
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...
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Episode 265
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26:58
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...
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Episode 264
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27:58
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 steps" eventually lead to a critica...
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Episode 263
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21:54
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 shifts and what they mean for your bottom line...
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Episode 262
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43:12
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 of these two common financial tropes.T...
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Episode 261
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22:30
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 industries like AI and tech that are booming...
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Episode 260
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28:52
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 Dividend Roth Strategy. We’ve all heard ...
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Episode 259
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28:42
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 look at the lessons of 2025 and a clear-eyed...
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Episode 258
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24:52
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 manage and dive into the 'North Pole Economi...
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Episode 257
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21:19
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 being ultra-wealthy.We unpack t...
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Episode 256
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21:41
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 several others from our Mailbag....
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Episode 255
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31:00
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 spending: Is hyper-focusing on every 24 hours empowe...
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Episode 254
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24:12
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 time with your family and friends this week, but...
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Episode 253
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21:43
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 mortgages to see who actually benefits. Plus, we’re ...
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Episode 252
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26:03
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 try to start a business or invest in somet...
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Episode 251
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30:39
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 that focus makes us 'house poor' or 'life po...
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Episode 250
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30:02
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 frightening for your portfolio (and what’s jus...
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Episode 249
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26:19
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 Averaging (DCA) out of a position a...
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Episode 248
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37:44
Is Burnout Leading to Your FIRE Dreams?
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...
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Episode 247
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27:24
Selling a House: Lessons from Our Best Real Estate Investor
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 bre...
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Episode 246
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27:14
Do you have any Super Dollars? (Roth Mailbag)
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 manda...
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Episode 245
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28:45