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 into the room with the people who made it all possible: You.

Join Ross and Dan for a special live taping of the Check Your Balances podcast! This isn't just another episode; it’s an interactive event dedicated to the community that has grown alongside us.

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Send your questions for upcoming show to checkyourbalances@outlook.com
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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 you should swing for the fences with high-growth stocks or play the long game with broad-market index funds. Finally, we tackle tax season head-on by evaluating if premium tax software offers genuine value or if you're better off with a less expensive option - and how to evaluate them. Whether you're weighing a new job offer or optimizing your retirement bucket, this episode provides the framework for making smarter money moves this spring.

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

But life rarely follows a linear spreadsheet. In this episode, we tackle the nuance of the "forbidden" withdrawal. We’re diving into the specific scenarios where paying the penalty might actually be the most logical—or least destructive—financial move available to you.

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Send your questions for upcoming show to checkyourbalances@outlook.com
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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 critical inflection point where momentum takes over. We discuss the transition from the "grind" of active saving to the moment your portfolio’s growth begins to outpace your contributions. By staying consistent through the heavy lifting, you allow your wealth to transform from a stationary pile into a self-sustaining engine.

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Send your questions for upcoming show to checkyourbalances@outlook.com
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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. From permanent bonus depreciation to the new incentive structures, we’re cutting through the noise to make sure you’re prepared for the "Big Beautiful Bill" you’ll face in April.

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

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