The Stacking Benjamins Show

JL Collins, author of The Simple Path to Wealth, shares his insights on simplifying investing and achieving financial independence. He humorously connects the dots between frosting and finance, emphasizing low-cost index investing as a stress-free path to wealth. Topics include the sneaky impact of debt, portfolio allocation, and the essence of 'FU money' as true freedom. The conversation also explores diversified asset classes and strategies for recent graduates, making financial literacy accessible and enjoyable, all with a sprinkle of humor.

Robert Niles, the mastermind behind Theme Park Insider, shares how to make the most out of your theme park outings. He reveals surprising tips for saving money, discusses the excitement of new attractions like a Disney park in Abu Dhabi, and highlights underrated parks such as Dollywood. The conversation also dives into how market 'memory' can impact your investment decisions, offering a fun mix of thrills and financial wisdom. Get ready for a perfect blend of roller coasters and smart money strategies!

Jesse Cramer, a savvy financial analyst, and Paula Pant, the founder of Afford Anything and real estate expert, join the roundtable for a lively debate on the true drivers of happiness in relation to finance. They tackle whether earning more or saving diligently impacts joy more significantly. The discussion is peppered with humorous 'either-or' dilemmas about credit cards versus cash and the merits of investing versus hoarding. Listeners are treated to personal stories, playful banter, and insights that challenge conventional financial wisdom.

Leisa Peterson, author of The Mindful Millionaire and The Money Catalyst, dives deep into shifting from a scarcity mindset to one of abundance. She shares a transformative moment in Paris that changed her relationship with money and emphasizes valuing experiences over material possessions. Alongside discussions about alternative investments and the quirks of generosity, Leisa encourages listeners to rethink expenses and prioritize fulfillment. Get ready for laughs as personal anecdotes illuminate the journey to financial and personal growth!

Sam Dogen, the Financial Samurai and author of 'Millionaire Milestones', shares his insights on building financial wealth through grit and clear goals. He explains why the first $250,000 is crucial for compounding success and emphasizes that knowing your 'why' is more important than budgeting. Sam also discusses the house-to-car ratio as a key indicator of financial health. Listeners learn about the impact of location on career growth, real estate investments, and the mindset necessary for financial freedom, all delivered with engaging anecdotes and humor.

Join Janice Torres, a finance expert and founder of the Financial Freedom Summit, alongside personal finance guru Len Penzo, as they tackle the challenges of food budgeting. They share practical meal planning tips to reduce waste, discuss the pros and cons of buying in bulk, and reveal which grocery apps can save you money. Enjoy their humorous anecdotes about grocery shopping and unexpected splurges, plus insights on how cutting back on meat can be budget-friendly. A delightful mix of useful hacks and laughs awaits!

Your burning questions fuel this episode! Joe Saul-Sehy, OG, and special guest Christine Benz of Morningstar unpack some of the biggest questions facing investors today—especially those just starting out. We kick things off by diving deep into target date funds. They promise simplicity—but do they deliver long-term results? We explore when they work, when they don’t, and what you should consider if they’re part of your portfolio. Then Christine shares a graduation-season masterclass in financial advice: How to begin investing, even when you feel behind Why lifestyle creep is the silent killer of wealth The importance of building habits now that will serve you for decades Resources and reading recs that can actually move the needle for new grads (and not-so-new grads) We also answer listener questions on: Whether refinancing your mortgage is still a smart move How global shifts in labor and supply chains may impact your finances And why it’s time to give your favorite retirement calculator a second look And somewhere in all this… someone may or may not reveal a dream dinner scenario that involves a pair of country music legends. But, you know, that part probably didn’t happen. Probably. Whether you're just graduating, recalibrating, or rethinking your strategy entirely, this episode is your invitation to stack smarter—and have a little fun while you do it. 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

Jen Sincero, bestselling author and success coach, shares her inspiring journey from living in a garage to becoming a seven-figure entrepreneur. She discusses powerful mindset shifts that transformed her relationship with money and offers advice on self-talk as a critical tool for financial success. Listeners learn practical ways to reprogram their spending and saving habits, along with the importance of consistent investing. Plus, she brings humor with anecdotes about marathon filming and quirky trivia, making for an entertaining and insightful conversation.

Join Jesse Cramer, host of the Personal Finance for Long-Term Investors podcast, as he passionately debates the benefits of buying versus renting a home. He reveals surprising truths about renting, dispels myths about homeownership being a guaranteed investment, and shares the hidden costs many new buyers overlook. With anecdotes and spirited discussions, Jesse emphasizes the need for financial flexibility and personal circumstances in the housing decision. Plus, enjoy some lighthearted trivia and banter that keeps the conversation lively!

Retirement might be the goal, but the journey? Full of curveballs. On today’s episode, Joe Saul-Sehy is joined by special guest co-host Len Penzo of LenPenzo.com, along with OG and Neighbor Doug, for a no-holds-barred look at what really derails retirement plans—and how to build a strategy that can handle the chaos. From unexpected job loss to rising long-term care costs, adult kids moving back home, and even changing relationship dynamics, this episode dives into the often-overlooked risks that can chip away at your retirement dreams. Inside the episode: What to consider when evaluating long-term care insurance How job instability late in your career can throw off your timeline The growing trend of adult children impacting their parents’ retirement Grandparents becoming full-time caregivers—and the financial toll that brings Relationship shifts and widowhood in retirement Downsizing, austerity planning, and staying financially flexible Plus, our TikTok Minute features Gary V on why taking a step backward might be the smartest move forward. And as always, Doug brings the trivia heat—this time, with a nostalgic nod to a certain potato-headed toy. With Len Penzo in the basement, the insights (and squirrel references) are extra sharp. Prepare to laugh, learn, and rethink what “retirement ready” really means. FULL SHOW NOTES: https://stackingbenjamins.com/four-things-that-can-derail-your-retirement-plan-1676 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