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The Stacking Benjamins Show

Latest episodes

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7 snips
Jul 11, 2025 • 1h 5min

The Stuff You Should Stop Buying (and Why Your Wallet Will Thank You) SB1707

Paula Pant, founder of Afford Anything, and Len Penzo, personal finance guru and TikTok legend, bring hilarity and wisdom as they tackle what we should stop buying. Discover why your treadmill may just be a fancy coat rack and the hidden costs of seasonal decorations that drain your wallet. They dive into magazine subscriptions as budget vampires and reveal unexpected items that quietly suck away your cash. With trivia and personal anecdotes, their lively banter makes decluttering your finances both fun and insightful!
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12 snips
Jul 9, 2025 • 1h 17min

Happy Money, Hidden Fees, and Hiring Your Kids (SB1706)

In this engaging discussion, Ken Honda, Japan's bestselling personal development guru and author of 'Happy Money,' dives into how gratitude can transform your relationship with finances. He shares insights on emotional finance, revealing that small mindset shifts can lead to significant life changes. The conversation also uncovers hidden fees in real estate commissions, urging listeners to be vigilant. Plus, practical tips on maximizing Health Savings Accounts and the complexities of hiring your kids for Roth IRA contributions add to the mix.
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10 snips
Jul 7, 2025 • 1h 9min

Want More Money? Cut The Clutter (with Tracy McCubbin) SB1705

In this enlightening discussion, organizational expert Tracy McCubbin, author of "Making Space, Clutter Free," navigates the emotional ties we have with clutter. She reveals why letting go can be liberating and offers strategies for donating intentionally. The conversation also touches on crucial financial advice, emphasizing the significant losses retirees face by claiming Social Security too early. Plus, a whimsical look at the Taco Bell Hotel promises some laughs! Tune in for practical tips on decluttering and securing your financial future.
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Jul 4, 2025 • 1h 8min

Let's Start a Money Revolution (SB1704)

Join Dorethia Kelly, a TikTok content creator and money coach, who transformed her financial life as a single mom, as she shares insightful strategies for smart money choices. Jesse Cramer, a personal finance expert, discusses the importance of intentional investing and budgeting to achieve financial independence. Steve Stewart reveals his journey toward mortgage freedom and the pivotal moment that changed his financial outlook. Together they tackle debt, lifestyle creep, and the need for open family discussions about money, all while keeping it fun and engaging.
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8 snips
Jul 2, 2025 • 1h 12min

Turning Ideas into Billion Dollar Businesses (with Julie Wainwright) SB1703

Julie Wainwright, founder of luxury consignment store The RealReal, shares her journey from setbacks like Pets.com to billion-dollar success. She discusses overcoming ageism in entrepreneurship and how your past failures can inform future triumphs. Julie emphasizes the importance of risk-taking and confidence while revealing the untold story of luxury resale markets. Listeners will gain insight into building a brand against the odds, and how perseverance can redefine one’s career path, regardless of age.
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Jun 30, 2025 • 58min

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! Learn more about your ad choices. Visit podcastchoices.com/adchoices
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9 snips
Jun 27, 2025 • 1h

Are Money Gurus Feeding Us Lies? (SB1701)

Paula Pant, host of the Afford Anything podcast, Jesse Cramer, a financial planner, and Doc G, known for the Earn & Invest podcast, gather to bust financial myths. They tackle whether budgets are really necessary and debate the effectiveness of strict financial formulas versus flexible approaches. The conversation dives into the myth of willpower in achieving financial stability and the impact of cutting up credit cards on spending habits. Expect laughs, trivia, and insightful discussions aimed at helping listeners find personalized financial strategies.
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7 snips
Jun 25, 2025 • 1h 4min

Your Questions Answered: Saving, Investing & Estate Planning, Stacker Style (Episode 1700!!!)

Dive into the world of personal finance as the hosts tackle saving for a house without jeopardizing retirement plans. Explore vital topics like the ideal emergency fund size, strategies for financial planning as a single adult, and managing inherited IRAs. Gain insights on juggling responsibilities with aging parents while pursuing personal goals. Discover practical budgeting tips, how to navigate real estate complexities, and why single individuals often miss out on tailored financial advice. It's a lively, informative discussion packed with actionable strategies!
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18 snips
Jun 23, 2025 • 59min

AI’s Coming for Your Job? How to Outwit the Robots (SB1699)

The discussion kicks off with the surprising trend of Gen Z avoiding AI-dominated careers by opting for trades where human creativity shines. The episode highlights the transformative role of AI, boosting productivity in skilled sectors while exploring new job opportunities. Listeners discover how being open to AI can enhance personal finance strategies. Data privacy concerns related to AI tools also take center stage, urging vigilance in protecting personal information. Tune in for a witty yet insightful take on navigating the future of work!
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17 snips
Jun 20, 2025 • 1h 30min

Carving Out a Robust Retirement Spending Plan (SB1698)

Join financial mavens Karsten Jeske, Dana Anspach, and Frank Vasquez as they explore the art of spending in retirement. Karsten, the Early Retirement Now expert, shares insights on withdrawal rates, while Dana discusses decumulation strategies to ease the transition to retirement. Frank dives into innovative portfolio strategies, emphasizing risk parity. They tackle the emotional hurdles of withdrawals, the role of annuities, and how to navigate unexpected expenses. Whether you’re retiring soon or well into your golden years, their advice is invaluable!

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