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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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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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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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
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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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This week, Ross and Dan tackle a fun question... If you had to invest $100,000 without using the stock market, what would you do? Would you become a landlord and try to buy real estate? Would you try to start a business or invest in something truly "passive?"

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Does the average financial plan have "retirement tunnel vision," with a focus on pouring every spare dollar into your retirement accounts. We're all told to save for the future, but what happens when that focus makes us 'house poor' or 'life poor' today? Big goals like buying a home, funding college, or starting a business can't always wait until you're 65. Is it possible to be too focused on saving for your golden years?

#retirement #financialplanning #balance

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Send your questions for upcoming show to checkyourbalances@outlook.com
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First up: A listener challenges our take on Dollar Cost Averaging out.

Then, we confront the fear: How spooky is this market? Ross and Dan bust the financial ghouls and tell you what’s truly frightening for your portfolio (and what’s just noise).

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