March madness isn't just for the court—sometimes, life throws a full-court press at your financial plan that you never saw coming. In this episode, we take a look at the "bracket busters" of personal finance: those unexpected or overlooked situations that can derail even the most carefully constructed strategy for financial independence.

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In this March mailbag episode, we’re diving into the listener inbox to tackle the psychological hurdle of oversaving and how to transition from a lifetime of hoarding to intentional spending. We also clear up the "sloppy" discourse surrounding Roth conversions, cutting through the noise to discuss the tax nuances and math that actually matter. Whether you're struggling to give yourself permission to spend or weighing a big tax move, we’re bringing some much-needed clarity to your financial plan.

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If you feel like the ground is shifting under your feet as a tech investor, you aren’t alone. Early 2026 has introduced a new term to the financial lexicon: the SAASpocalypse. With AI agents beginning to perform tasks that used to require a $50-per-seat software subscription, the traditional "moats" of the software-as-a-service world are being tested like never before.

This week, we are joined by Simon Erickson, founder of 7Investing and one of the most forward-looking minds in growth investing. Simon helps us break down whether the recent $1 trillion sell-off in software stocks is a permanent structural shift or the ultimate "buy the dip" opportunity.

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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 distributions on a mutual fund, and also weigh in on whether its the right time to refinance a high rate mortgage.

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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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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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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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