The Stacking Benjamins Show

• How To Use Our #1 Key To Money Management Success (SB1641)

  Is automating your finances the key to effortless money management, or a one-way ticket to financial autopilot disaster? Paula Pant, Jesse Cramer, and Doc G join us to navigate the fine line between automation genius and accidental money mayhem. Done right, automation saves you time and stress. Done wrong? You might be funding a forgotten gym membership for the next five years. 😬 What’s Inside This Episode? 💰 The Power of Automation – How strategic automation can make your financial life simpler, more efficient, and stress-free. 🤖 What to Automate & What to Keep Manual – Should you set bills to auto-pay, or will that lead to mysterious charges on your credit card? 📊 High-Tech Money Tools: Are They Worth It? – Todoist, Notion, and other techy automation tricks—are they game-changers or just digital clutter? 💡 Personal Automation Hacks – How the panel automates their finances like pros (without losing control of their money). 🎭 The Dark Side of Automation – Horror stories of overdraft surprises, vanishing paychecks, and auto-pay regret. 📢 Stacker Debate: Should You Automate Everything? – The great automation showdown—when automation helps and when it hurts. ✨ Special Bonus: The Worst Things to Automate – Some things should NEVER be on autopilot. Find out what financial automation fails made our list. Takeaways for Smart Stackers: ✅ Automation = Freedom (When Used Wisely). The right balance saves you time while keeping you in control. ✅ Auto-pay is great—until it isn’t. Track subscriptions and bills so you don’t end up paying for things you don’t use. ✅ Manual check-ins keep you financially sharp. Even with automation, you need to review your money regularly. ✅ Tech tools can help—but they’re not magic. The best system is the one you actually use. 🎧 Hit play now and rethink your approach to automation before it outsmarts you! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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• Yet Another Insurance To Avoid (SB1640)

  What do scammers, fancy doors, and Twinkies have in common? Turns out, more than you think! Today, Joe, OG, and Doug take you on a wild ride through financial scams, fraud prevention, tax implications of dual residency, and... the surprising link between door quality and financial stability. (Yeah, we didn’t see that one coming either.) What’s Inside This Episode? 🕵️‍♂️ Scams, Scams Everywhere! – From identity fraud to the trendy new "deed theft" scam, learn how to protect yourself before a scammer claims your house faster than you can say "that wasn't in the budget." 💳 Fraud-Proofing Your Finances – Why setting up credit monitoring, checking your bills, and paying attention to sketchy emails can save you thousands in headaches. 🚪 The TikTok Minute: What Do Soft Close Doors Say About Your Wealth? – Is your financial future written in the way your doors shut? Find out why door noises might reveal more about your bank balance than your credit score. 🧾 State Taxes & Dual Residency: The Sneaky Costs of Living in Two Places – Thinking about snowbirding to Florida or keeping a backup home in another state? We break down what you NEED to know before state tax authorities come knocking. 🤖 Password Security & The Quantum Computing Takeover – Is the future of passwords doomed? What you should be doing now to keep your Twinkies—and your bank accounts—safe. 🍕 Pizza Cutting Controversy & Nostalgic Minivan Stories – Because what’s a Stacking Adventures episode without a little debate, a little reminiscing, and a whole lot of questionable opinions on pizza slicing? 🍰 Twinkies Trivia: A Deep-Dive into the Snack That Never Dies – Have scientists unlocked the secret of Twinkie immortality? More importantly, should Twinkies be considered part of a solid financial plan? (Spoiler: probably not, but let’s discuss.) 📢 Stacker Questions & Community Fun – Helping a listener navigate dual residency tax headaches + a special meetup announcement! Takeaways for Smart Stackers: ✅ If it sounds too good to be true, it’s a scam. Seriously. Trust your gut, not the email from "Prince Jeff of Nigeria." ✅ Your finances need monitoring, just like your snack stash. Set up credit alerts and check your accounts weekly to avoid surprises. ✅ Moving states for tax savings? Do the math first. Dual residency isn’t always the loophole people think it is. ✅ Twinkies may last forever, but financial security requires maintenance. A solid money plan beats a stockpile of snacks (but only slightly). 🎧 Hit play now for a mix of financial wisdom, scam-prevention tips, and just the right amount of Twinkie-fueled fun! 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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• Redefining Retirement with Benjamin Brandt (SB1639)

  Retirement planning isn’t about waiting until 65—it’s about setting yourself up for a life you love starting right now! Today, Certified Financial Planner Benjamin Brant joins us to challenge traditional retirement thinking. What We Cover: ✅ Retirement planning starts now, not later – Why waiting to plan is the biggest mistake you can make. ✅ Dream big, but expect some ‘bad data’ – How testing financial plans (and life plans!) helps you refine your future. ✅ Why trust beats performance in financial planning – A new study shows that your advisor’s returns matter less than their integrity. ✅ The Monte Carlo simulation debate – What this financial tool actually tells you (and what it doesn’t). ✅ Childhood dreams, stand-up comedy, and time travel? – How revisiting past joys can shape a meaningful retirement. ✅ Choosing the right financial advisor – The #1 factor to look for before handing over your portfolio. Key Takeaways: 💡 Retirement isn’t a number—it’s a mindset. The earlier you start thinking about what brings you joy, the better. 💡 Financial planning isn’t perfect science. Bad data, trial-and-error, and adjusting your plan over time? Totally normal. 💡 Trust is your biggest investment. A good financial advisor isn’t just about returns—they’re about guidance you can rely on. Grab your favorite drink (coffee, bourbon—you choose!) and let’s stack some wisdom for your future self. 🎧 Hit play now and start building your best retirement today! FULL SHOW NOTES: https://stackingbenjamins.com/find-your-fulfillment-in-retirement-Benjamin-Brandt-1639 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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• The Case Against Early Retirement (SB1638)

  Ever dreamt of quitting your job early and sipping piña coladas on a beach? Before you tell your boss what to do with that job and start booking your one-way ticket to paradise, today’s roundtable might make you think twice. Join Jesse Cramer from The Best Interest, Paula Pant from Afford Anything, and our own OG as they break down the case against early retirement. The gang’s here to challenge the “quit work, retire early” dream and explore whether it’s really as awesome as it sounds—or if there are a few catches you haven’t considered. The conversation gets into the nitty-gritty of why early retirement might not be the smooth ride some people think it is. From the psychological toll of too much free time to the unexpected financial hurdles, our panelists share the real stories behind the headlines. What’s the balance between financial freedom and a fulfilling life? Can you really retire early without regret, or does the cost of quitting work too soon outweigh the benefits? And don’t forget about Doug’s wicked trivia challenge! FULL SHOW NOTES: https://stackingbenjamins.com/the-case-against-early-retirement-1638 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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• Unpacking a Rare Vanguard Target Date Fund Problem (SB1637)

  Ever wondered if you’re better off building your own target date fund instead of relying on a one-size-fits-all option? We’re diving into whether crafting your own investment mix is worth the effort, potentially saving you fees and giving you more control over your portfolio. But even the pros get it wrong sometimes—just ask Vanguard. We’re covering the major settlement they’re facing over misleading statements about taxes and target date funds, proving that even the big guys make costly mistakes. Meanwhile, a listener asks a great question about balancing tax optimization with financial flexibility—because what good is a perfectly tax-efficient plan if it ties your hands when you need cash? Plus, Doug takes us back to the origins of the gasoline-driven automobile, and there’s even an unexpected run-in with a Supreme Court justice (because why not?). And of course, we’ve got a TikTok moment that’ll have you questioning life choices and a few financial misconceptions that might just make you rethink your approach to money. What’s Inside Today’s Episode: Vanguard’s Costly Mistake: The settlement every investor should know about. Understanding Mutual Fund Taxes: How taxes sneak up on your investments. DIY Target Date Funds: Pros, cons, and when to consider building your own. Trivia Time with Doug: The surprising story behind the gasoline-driven car. The TikTok Minute: Financial advice that may (or may not) be worth your time. Financial Flexibility vs. Tax Optimization: Finding the balance in your strategy. Community Announcements & Meetups: Where to find us next. Episode Highlights: Vanguard’s Legal Trouble: What happened, and what it means for investors. Mutual Fund Taxation: Avoiding unexpected tax bills. Should You Build Your Own Target Date Fund? We break down the numbers. Listener Q&A: How to stay tax-efficient while keeping access to your cash. Doug’s Trivia: Who REALLY built the first gasoline-powered car? An Unexpected Supreme Court Encounter: Because that’s just how things go around here. Resources Mentioned in This Episode: Learn more about Vanguard’s target date fund settlement in our show notes: https://www.stackingbenjamins.com/vanguard-target-retirement-trouble-1637 Read up on mutual fund tax strategies and more by signing up for our 201 newsletter! https://stackingbenjamins.com/201 Tune in now and get the insights you need to build a smarter investment strategy—without falling into costly traps. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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