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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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 between corporate finance and your front door, breaking down how inflation acts as a "discount" on long-term debt like mortgages. By analyzing the math of eroding buying power, we reveal why time is the ultimate lever for the borrower—and how you can use a fixed-rate mindset to short the dollar and build long-term wealth.

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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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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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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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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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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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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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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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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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