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The Stacking Benjamins Show

Latest episodes

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Apr 14, 2025 • 1h 15min

Money and Business Lessons from the Career of Taylor Swift (and a BIG Roth IRA rule clarified) SB1670

This week, the discussion is all about the savvy business moves of Taylor Swift! The hosts explore how she transformed from a teen star to a powerhouse by controlling her creative output and mastering strategic collaborations. Listeners will learn to avoid their own ‘sophomore slump’ in finance and music through clarity and consistent effort. Plus, they tackle the ins and outs of Roth IRAs, specifically the five-year rule, debunking myths while keeping it entertaining. Expect humor, career insights, and valuable financial strategies throughout!
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16 snips
Apr 11, 2025 • 1h 12min

Conquering Investment Fears and Risks (SB1669)

Joining the conversation are Paula Pant, host of the Afford Anything podcast focused on real estate and financial independence, and Dr. Jordan Grumet, a deep thinker in finance and author of 'The Purpose Code'. They explore the nuances of investment risks, highlighting the difference between perceived dangers and real threats. Topics include the psychological barriers to stock investing, the implications of liquidity, and the perils of overconcentration. Lively anecdotes about milkshakes and humorous trivia add a delightful twist to their insightful discussion.
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Apr 9, 2025 • 1h 4min

How To Smooth Out Your Investing Ride...or not (SB1668)

Market volatility can be daunting, but keeping things simple might just be the smartest strategy. Discover how to manage your investments without losing sleep, and whether to choose diversified portfolios or one-stop fund solutions. Learn the common misconceptions about investment risks and the importance of a long-term mindset. A listener's retirement planning query adds a personal touch, while humorous anecdotes and trivia spice up the financial insights. It's an engaging blend of advice, laughter, and unexpected stories.
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11 snips
Apr 8, 2025 • 27min

Special Episode: Tariff Fallout - What Should You Do?

Feeling anxious about tariffs? The hosts dive into what recent tariff changes mean for your investments and how to navigate market fluctuations. They discuss why doing nothing can sometimes be the best strategy. Historical economic crises are explored, revealing how past mistakes influence today's financial landscape. You'll also learn about the importance of long-term investment and proactive financial strategies, all while keeping a calm and humorous vibe. Prepare to tackle uncertainty with confidence!
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8 snips
Apr 7, 2025 • 1h 19min

From Basement Beginnings to Million-Dollar Dreams (with Rudy Mawer) SB1666

Rudy Mawer, the founder of 60 Day Hustle and Maher Capital, shares his inspiring journey from a modest upbringing in England to becoming a thriving entrepreneur. He discusses the crucial role of mentorship and networking in his success and emphasizes the importance of balancing hustle with building a legacy. The conversation also delves into the anxiety around saving money, sparked by Seth Rogen’s insights, prompting reflections on enjoying life versus financial security. And don’t miss the amusing tales about guinea pigs that kick off this engaging discussion!
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9 snips
Apr 4, 2025 • 1h 9min

BIG Questions In Finance: Are You IN or OUT? (SB1665)

Paula Pant, founder of Afford Anything, and Jesse Cramer, host of The Personal Finance for Long-Term Investors Show, join a lively roundtable discussing polarizing finance topics. They tackle the myth of 'good debt' and debate whether living without a budget can lead to freedom or regret. With insights on the awkward yet valuable necessity of money discussions with family and friends, they also examine the trade-offs of pursuing FIRE goals. Plus, enjoy some light-hearted trivia that brings laughs along with the learning!
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13 snips
Apr 2, 2025 • 1h 14min

Top 5 Eye-Roll Financial Tips You Should Ignore SB1664

Explore the top five worst financial tips that could ruin your finances, from buying a massive house to skipping insurance. Discover the pitfalls of relying on misguided advice, like sharing a checkbook in relationships. Laugh along with critiques of TikTok money myths and the absurdity of DIY mishaps. Engage with listener Q&As delving into investment topics, all while gaining insights into personal finance that empower you to dodge bad advice with confidence!
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Mar 31, 2025 • 1h 14min

Tiffany Aliche on Connections and Financial Wholeness (with a side discussion on recent DoorDash/Klarna news) SB1663

Tiffany Aliche, known as The Budgetnista, is a personal finance expert and author of "Get Good With Money." In this episode, she shares her journey to financial wholeness and insights from her PBS special. The conversation dives into the impact of community on financial literacy, the pitfalls of 'Buy Now, Pay Later' schemes, and humorous reflections on adulting and budgeting. Tiffany also tackles stage fright and the importance of continuous learning in finance, all while addressing some recent eye-opening headlines.
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Mar 28, 2025 • 1h 5min

Better Investing Using Horrible Investment Products (SB1662)

Paula Pant, a personal finance expert and host of Afford Anything, joins Jesse Cramer from Personal Finance for Long-Term Investors and financial guru Don McDonald. They dive into the pitfalls of poor investment products like infinite banking and penny stocks, revealing how they often lure investors into traps. The panel humorously contrasts gut feelings with hard data and sheds light on the complicated world of 403(b) plans for educators. Expect a mix of insightful advice and lighthearted trivia, making finance both informative and entertaining!
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8 snips
Mar 26, 2025 • 1h 18min

How NOT To Invest: Lessons from Barry Ritholtz SB1661

Barry Ritholtz, founder of Ritholtz Wealth Management, dives into the world of investing with a twist on traditional advice. He discusses the vital lessons on what NOT to do when investing, emphasizing behavioral finance and the dangers of chasing trends. Barry highlights how understanding market history can prevent costly mistakes and critiques the illusion of financial literacy. He shares insights from his latest book, explores the pros and cons of tech innovations in finance, and offers practical tips for financial security, all laced with humor and relatable anecdotes.

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