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Check Your Balances — Business
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.

Copyright: © 2023 Check Your Balances

Latest Episodes:

What Might Bust Your Bracket? Apr 01, 2026

Show notes

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

The March Mailbag: From Scarcity Mindsets to Roth Nuance Mar 25, 2026

Show notes

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.

Send us Fan Mail

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

SAASpocalypse, Quantum, and AI investing with Simon Erickson Mar 18, 2026

Show notes

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.

Send us Fan Mail

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

Capital Gains and Refinances, Our favorite topics? Mar 11, 2026

Show notes

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.

Send us Fan Mail

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

Celebrating 5 Years with a Live Listener Event Mar 04, 2026

Show notes

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.

Send us Fan Mail

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

1099 vs W2 Jobs & More: February Mailbag Feb 25, 2026

Show notes

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
@checkyourbalances on Instagram

If you could borrow money for 100 years, should you? Feb 18, 2026

Show notes

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.

Send us Fan Mail

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

When Does It Make Sense to Pay Retirement Account Penalties? Feb 11, 2026

Show notes

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.

Send us Fan Mail

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

Are You Underestimating the Impact of Baby Steps? Feb 04, 2026

Show notes

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.

Send us Fan Mail

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

Are Your Taxes Ready for the OBBB With Ryan Flanigan, CPA Jan 28, 2026

Show notes

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.

Send us Fan Mail

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

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