The Stacking Benjamins Show

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

Join Paula Pant, host of the Afford Anything podcast, as she delves into the sneaky ways convenience drains our wallets. They tackle the outrageous prices of airport food, revealing why a sad turkey sandwich beats a steak dinner in cost. Concert ticket fees become a surprising topic of discussion, showcasing how quickly a cheap deal turns expensive. Paula shares creative strategies to cut wedding costs without sacrificing fun, and the conversation wraps up with Ben Franklin's timeless wisdom about building connections—all while keeping it light and humorous!

Tax season tips are here! Discover which tax software reigns supreme this year, with options like TurboTax, H&R Block, and the surprising new frontrunner, FreeTax USA. Learn how to prepare for filing, even if you’re a side hustler or crypto investor. H&R Block's virtual help and strategies for stress-free filing ensure you won’t leave money on the table. Plus, enjoy trivia and insights on market trends, movie recommendations, and the quirks of crypto taxes. It's your essential guide to navigating tax season with a smile!

Grant Sabatier, bestselling author of "Millennial Money," shares his insights on entrepreneurship and financial freedom. He discusses the reality behind starting your own business, emphasizing the importance of knowing if it's the right path for you. Grant highlights the power of structure over limitless freedom and offers clever pricing strategies to find customers. He also debunks entrepreneurial myths like the glamorous lifestyle and even tackles the quirky topic of tax-deductible weddings. Packed with real talk and surprises, this conversation is a must-listen for aspiring entrepreneurs!

Feeling the pressure to constantly tweak your investments? Today, we uncover the surprising benefits of financial inaction with insights from CFP Dana Anspach, Len Penzo, and OG. We dive into the wisdom of sometimes doing nothing—because, as it turns out, sitting on your hands (financially speaking) can be a power move. Why lazy portfolio management might be the smartest strategy you’ll ever adopt (spoiler: it involves less work). The power of downtime—turns out, stepping away from your money might actually make you richer. Why your future self will thank you for setting up auto-pay (hint: fewer late fees, more naps). The sneaky ways peer pressure messes with your finances—and how to keep the Joneses from running your budget. When rebalancing your portfolio is necessary…and when it’s just a fancy way to micromanage yourself. A wildly unexpected insurance claim (because finances are never boring in the basement). Oh, and Doug’s got a trivia question about a particularly controversial activity that was banned—because, apparently, not everything fun is legal.Stick around for weekend plans, final thoughts, and maybe even a surprise or two (because we like to keep you on your toes).This episode originally aired on June 10, 2022. Please disregard any mention of current events.The original show notes can be found here.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

Discover the art of financial planning with insights that turn dreams into reality. Learn how to break big goals into manageable steps, ensuring each victory counts. Dive into tax strategies that can save you money over time. Understand the importance of risk management to safeguard your financial future. Simplicity is key, as often the best strategies are the easiest. Plus, hear why having a financial guide can transform your approach. Join in for an engaging conversation sprinkled with fun anecdotes and valuable advice!