Want More Money? Cut The Clutter (with Tracy McCubbin) SB1705
Is your home packed with emotional baggage... and maybe a few fondue sets you haven’t touched since 2003? Organizational expert Tracy McCubbin joins us to talk about the emotional side of clutter—why it builds up, how it weighs us down, and what to do when your sentimental stuff is quietly running the show.
Meanwhile, Joe and OG dig into another kind of mess: the billions retirees lose by claiming Social Security too early. Timing isn’t just everything—it’s the difference between thriving in retirement and wondering where all the money went.
In this episode, we cover:
Why sentimental clutter is more than just "stuff"—and how to finally let it go.
How donating intentionally can breathe new life into your old things (and clear some mental space).
The tough conversations adult kids need to have with parents about downsizing and letting go.
Strategies to help you avoid making costly Social Security decisions.
A surprisingly thoughtful take on the Taco Bell Hotel (yes, it’s real... and yes, it sold out in minutes).
Plus: a listener question, some truly questionable fashion choices, and one more reason not to hoard your retirement benefits—or your holiday dishes.
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1:08:33
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1:08:33
Let's Start a Money Revolution (SB1704)
Happy Independence Day, Stackers! While fireworks boom and flags wave, we're lighting a spark under your financial life. This episode isn’t about tea in harbors—it’s about burning down debt, revolting against lifestyle creep, and rallying your family for a better money future.
Joining Joe and Doug in the basement for this full-on financial insurrection:
Dorethia Kelly, TikTok titan and money coach, shares how she raised her financial flag as a single mom and became a force for smart money choices.
Jesse Cramer of the Personal Finance for Long-Term Investors podcast ditches tired spending habits and charts a course for independence through intentional investing and budgeting.
Steve Stewart, longtime SB editor and podcasting Yoda, reveals the pivotal Jeep moment that changed his financial course—and why he's racing OG to mortgage freedom.
🎙️ In this basement-based revolution, you'll hear:
The financial “tea party” moments that woke our guests up to their money mess
How to declare independence from credit cards, lifestyle creep, and sneaky “Buy Now, Pay Later” traps
Tools, mindsets, and support systems that help you keep your financial revolution alive
Why tax planning is the financial Boston Tea Party nobody's talking about
The trivia showdown no revolutionary should miss: How many grains of silver made a dollar in 1792? (Spoiler: Jesse knows his colonial coinage.)
And in the aftershow? We ask the deep questions our Founding Fathers never saw coming, like: why is gambling debt dischargeable in bankruptcy, but student loans aren't?
FULL SHOW NOTES: https://stackingbenjamins.com/financial-independence-day-2025-1704
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
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1:08:06
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1:08:06
Turning Ideas into Billion Dollar Businesses (with Julie Wainwright) SB1703
What does it take to turn a bold idea into a billion-dollar brand? Julie Wainwright, founder of The RealReal, joins us to share how she did just that—after enduring some pretty public failures (hello, Pets.com). She talks about navigating the startup world, tackling ageism head-on, and why your past doesn’t define your future.
Julie’s story is packed with wisdom on risk-taking, confidence, and what it really means to build something new when everyone else is telling you no. From the boardroom to the resale boutique, she takes us through the emotional rollercoaster of entrepreneurship—plus a few secrets on why luxury goods are more than just a pretty label.
Also in the basement:
We unpack Jason Zweig’s latest Wall Street Journal column on diversification and why it still matters (yes, even in this market).
OG learns a Father’s Day lesson on the golf course (spoiler: not all swings are created equal).
Doug manages to work in Margot Robbie. Again.
Whether you’re plotting your own business empire or just wondering how someone not only recovers from flaming sock puppet-level failure, but who THRIVES afterward, this episode delivers honest insight with a side of style.
FULL SHOW NOTES: https://www.stackingbenjamins.com/from-business-idea-to-execution-julie-wainwright-1703/
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
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1:11:34
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1:11:34
Is the 4% Rule In Play? (SB1702)
How much can you really spend in retirement without running out of money—or worse, running out of fun?
In this deeper-than-usual dive, Joe Saul-Sehy and OG examine the classic 4% retirement rule and whether it’s time for an upgrade. With new commentary from Bill Bengen, the original architect of the 4% rule, the team explores emerging research that suggests a withdrawal rate closer to 5.5% might be possible—if you’ve got the right mix of investments, a solid plan, and a bit of courage.
But we don’t stop there. Because with greater freedom comes greater risk (especially if you're leading with vibes instead of strategy). The guys tackle the sequence of returns risk that can derail early retirement years, and how to build a portfolio that helps you sleep at night—even during a market storm.
Meanwhile, Doug drops in with an unexpected (and very British) culinary experience, Joe fields a listener question comparing financial plans to workout routines (is your Roth IRA doing enough reps?), and yes... we revisit our fan-favorite segment on how food waste is wrecking your budget.
Why the 4% rule might be too conservative (or maybe just outdated).
What diversified portfolios and asset class strategy have to do with a longer-lasting nest egg.
How to prepare for market downturns before they happen—and what to do if you're already in one.
Why retirement joy isn’t just about spreadsheets—it’s about the psychology of spending with confidence.
Which type of green tea is the superior kind (depending on which side of the TikTok aisle you're on).
How to reduce food waste and put that extra savings toward your bigger financial goals.
If you’re approaching retirement—or even just dreaming about it—understanding how much you can safely spend without sabotaging your future is the question. This episode combines historical insight with today’s market realities to give you the real math and mindset you need to retire well…and maybe even with a smile.
FULL SHOW NOTES: https://stackingbenjamins.com/problems-with-the-4-percent-rule-1702
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
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57:37
Are Money Gurus Feeding Us Lies? (SB1701)
Can you really build wealth with a simple formula? Do you need a budget to succeed financially? Should you cut up all your credit cards, or is that just a dramatic TikTok trend?
In this episode of The Stacking Benjamins Show, Joe Saul-Sehy is joined by Paula Pant, Doc G (Jordan Grumet), and Jesse Cramer for a roundtable discussion that peels back the truth behind popular advice from so-called financial “gurus.” The conversation is rooted in a provocative blog post by Christine Luken that calls out four common money mantras—and the team dives into each one with classic basement wit, spirited debate, and hard-earned wisdom.
Topics on the table:
Do you really need a budget, or can you thrive without one?
Are rigid financial formulas helpful or harmful?
Is willpower the key to financial success—or just a scapegoat?
Does cutting up credit cards actually solve your spending problems?
Along the way, you'll hear banana jokes (yes, multiple), a heated trivia contest about obsolete technology (looking at you, LaserDisc), and some good-natured trash talk that might just surprise you with how insightful it gets.
This episode is packed with nuance, laughs, and practical takeaways for Stackers who are tired of the one-size-fits-all guru approach. Whether you’re team budget or team spreadsheet freestyle, there’s something here for you—plus a solid reminder that when it comes to personal finance, the best advice is the advice that fits your life.
FULL SHOW NOTES: https://stackingbenjamins.com/lies-damn-lies-and-statistics-1701
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
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Named the Best Personal Finance Podcast by Bankrate.com and Kiplinger, The Stacking Benjamins Show features a light and friendly tone. Hosts Joe Saul-Sehy and OG aim to make financial literacy fun for all as they sit around the card table in Joe's Mom's half-finished basement and talk with experts about personal finance, saving, investing, and important money trends. As Fast Company once wrote, the Stacking Benjamins podcast "strikes a great balance of fun and functional." So join Joe and OG every Monday, Wednesday and Friday as they read your letters, discuss major headlines, and throw in some trivia and laughs for free.
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