Check Your Balances

Latest Episodes:

Are Annuities and Real Estate Our Favorite Punching Bags? Jan 21, 2026

Show notes

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 problem that doesn't exist. Whether it’s the over-glamorized world of property management or the fear-based selling of insurance products, we’re here to help you spot the red flags before you sign a contract. Tune in for a dose of much-needed skepticism and a reality check on our favorite financial punching bags.

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Investing in a K Shaped Economy Jan 14, 2026

Show notes

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. On the "downward" arm, you have those feeling the squeeze of high interest rates, stagnant wages relative to costs, and the "disappearance" of affordable housing.
In an environment where the "market" and the "economy" are moving in different directions, how should you be positioning your portfolio?

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Does a tax free dividend Roth work? - Mailbag Episode Jan 07, 2026

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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 that Roth IRAs are powerful, but a listener asks if specifically loading a Roth with high-yield dividend stocks is the ultimate "cheat code" for retirement cash flow. That and more on this week's episode!

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So Long 2025 from CYB! Dec 31, 2025

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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 strategy for your money as we head into 2026.

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Would The Grinch be the worst client? Dec 24, 2025

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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 Economics' of how Santa actually funds his global operation.

Beyond the festive fun, we explore what these fictional portfolios teach us about behavioral finance, cash flow, and legacy planning. Join us for a holiday-themed deep dive on this week’s Check Your Balances!

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Is $100 Million Enough for Generational Wealth? Dec 17, 2025

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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 the eye-opening comments from NFL star Odell Beckham Jr. about how quickly a pro athlete's money evaporates. At this level, do standard retirement rules still apply, or are you just running faster on a much bigger treadmill?

Tune in to find out!

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Why buy bonds when cash looks better? - Mailbag Episode Dec 10, 2025

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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.

* Data as of 11/30/2025 via Vanguard

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Daily Budgeting: Sanity or Stress? Dec 03, 2025

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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 empowering and key to hitting your goals, or is it a recipe for driving yourself completely nuts? We'll reveal how we came to this counter-intuitive idea and deliver our verdict on whether a daily approach could finally be the breakthrough your budget needs. Tune in this week for our take!

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Does High Watermarking turn progress into disappointment? Nov 26, 2025

Show notes

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 if you want your weekly dose of personal finance content, we're here for you!

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

Does a 50 Year Mortgage Make Sense? - Mailbag Episode Nov 19, 2025

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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 emptying the mailbag to cover the specific financial hurdles you are facing right now. Tune in to this week's mailbag episode!

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