The Stacking Benjamins Show

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!

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!

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!

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.

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!

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.

Join a lively discussion about how weddings, wineries, and even Whoppers connect to smart investing. Discover ten essential tips from Barry Ritholtz that help navigate market cycles and keep your emotions in check. Learn about the real impact of politics on your portfolio, and why setting realistic investment expectations can liberate your strategy. Plus, hear a touching listener question about investing for an elderly parent. And don't miss the nostalgic trivia involving collectibles like Beanie Babies!

Jesse Kramer, host of the Personal Finance for Long-Term Investors podcast, and Dana Anspach, a CFP and retirement planning expert, dive deep into the art of financial motivation. They explore why many struggle with financial planning and how goal-setting psychology influences our habits. Dana shares insights on how tracking retirement balances can drive savings, while they discuss the need for financial advisors to take on more active roles, akin to sports coaches. Plus, a fun trivia segment about junk fees adds a playful twist!

Ever feel like you're stuck in a rut, spinning your wheels, or just running low on motivation? Today, we crack the code on sustaining drive and avoiding complacency with former sports agent Molly Fletcher, who’s worked with some of the biggest names in sports and has been dubbed the female Jerry Maguire. She breaks down the fine line between contentment and coasting, plus shares keys to staying at the top of your game—from managing energy to embracing adversity like a pro.But wait, there’s more! Len Penzo (yes, of LenPenzo dot com fame!) joins us as guest co-host, bringing his usual mix of wisdom, dry wit, and probably a few thoughts on sandwich prices.And if you think motivation is tough, try navigating the world of credit—because while ambition is great, bad credit can still trip you up. From student loan pitfalls to practical credit repair tips, we cover what younger folks (and honestly, all of us) need to know about keeping those numbers in check.In this episode: Molly Fletcher on Peak Performance – Lessons from a top sports agent on how to stay motivated without burning out. Complacency vs. Contentment – Are you stuck or simply satisfied? Molly breaks it down. Managing Energy Like a Pro – Tom Izzo swears by it, and so should you. Credit Crash Course – What happens when student loans go delinquent, and how to fix the damage. The Living Without Credit Debate – Is a debt-free life possible, or just a financial myth? Doug & OG’s Ski Slope Disaster – A story of poor decisions, gravity, and bruised egos (hilarious in retrospect). Len Penzo's Tips for Improving Credit Scores – Because nobody budgets quite like Len.Whether you need a motivation boost, a credit check-up, or just a good laugh at Doug’s expense, this episode has you covered.🎧 Tune in for wisdom, financial hacks, and some après-ski storytelling you won’t want to miss!FULL SHOW NOTES: https://www.stackingbenjamins.com/find-your-dynamic-drive-molly-fletcher-1658/Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever start a new financial goal feeling unstoppable, only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter.Today, Joe and OG take a deep dive into Dynamic Drive, the key to keeping your financial momentum going without burnout. We’ll break down the seven essential pillars—mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re ready to hit the ground running when we welcome former sports agent Molly Fletcher on Wednesday.💰 In this episode:Why motivation fizzles out—and how to make it lastThe seven keys to Dynamic Drive (and how to apply them to your finances)How milestones and energy management keep you on track Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins?What cowboy fencing teaches us about peak performance (yes, that’s a thing)Plus, Doug serves up a sports trivia challenge—because what’s financial motivation without a little fun?👉 Listen in now and get fired up—without burning out!FULL SHOW NOTES: https://stackingbenjamins.com/how-to-create-a-sustainable-drive-1657Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices