The Stacking Benjamins Show

• How to Deliver the “WOW” in Everyday Life (with longtime former Royal Caribbean Chairman and CEO Richard Fain) SB1748

  You don’t have to command a cruise ship (or a boardroom) to lead with purpose. On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome Richard Fain, longtime chairman and former CEO of Royal Caribbean Group, for a conversation that’s not about corporate leadership… but about life leadership. Richard shares timeless lessons he learned from decades steering one of the world’s most innovative companies—lessons that apply just as powerfully to parenting, coaching your kid’s soccer team, running a PTA fundraiser, or simply trying to create more joy at home. You’ll hear how to dream bigger about your own life, build a culture of kindness and excellence in small groups, and turn the ordinary moments around you into opportunities to “deliver the WOW.” Of course, this wouldn’t be the basement without a few money detours. The crew also breaks down new 401(k) rules and annuity updates, debates whether tax flexibility beats fancy planning, and celebrates Doug’s birthday with trivia, laughter, and a few movie reviews along the way. By the end, you’ll walk away inspired to bring a little more vision, creativity, and generosity into every corner of your world. No cruise ship required. What You’ll Learn How to lead from wherever you are: Richard’s lessons on building strong teams, communities, and families. No corner office needed. Turning the ordinary into extraordinary: Simple ways to “deliver the WOW” at home, work, or anywhere people count on you. Dreaming bigger about your life: Why bold vision isn’t just for CEOs; it’s for anyone looking to create meaning and momentum. Financial updates you can use: New 401(k) rules, annuity insights, and practical tips to strengthen your plan. The lighter side of leadership: Trivia, birthday celebrations, and a few fun detours (because we can’t resist). Questions for the Basement What’s one way you could “deliver the WOW” in your own life this week? Who’s a leader in your everyday world (at home, work, or your community) who’s made an impact on you? How can dreaming a little bigger change the way you approach your next financial or personal goal? FULL SHOW NOTES: https://stackingbenjamins.com/better-money-habits-with-richard-fain-1748 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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• Build a Confident Early Retirement Plan (Without Overthinking It) SB1746

  Who says you have to wait until 65 to clock out and start living your best life? On this episode of The Stacking Benjamins Show, Joe Saul-Sehy, Paula Pant (Afford Anything), OG, and special guest Sean Mullaney—author, CPA, and early retirement strategist—explore how to design a life that lets you walk away from the office sooner and happier. From tax-smart withdrawal strategies to dialing in your lifestyle design, this conversation pulls back the curtain on what it really takes to achieve early financial independence. You’ll hear practical steps for aligning your money with your values, structuring your investments for flexibility, and ensuring your plan can survive market dips and surprise expenses. Along the way, the team debates Roth vs. Traditional retirement accounts, shares personal insights from FinCon, and delivers a few laughs (and groans) in Doug’s trivia corner. Whether you’re in your 30s planning a slow exit or in your 50s wondering if it’s too late to pivot, this episode is your guide to crafting a retirement plan that works as hard as you do—without losing sight of the joy along the way. What You'll Learn How to design your early retirement plan: The building blocks of lifestyle design and financial freedom. Tax-efficient investing: When to prioritize Roth vs. Traditional accounts—and why both can play a role. Withdrawal strategies that work: How to avoid tax traps and keep your plan sustainable. The mindset shift: Why retiring early isn’t about leaving work—it’s about moving toward purpose. How to “future-proof” your finances: Guarding against inflation, longevity risk, and unexpected curveballs. Questions to Ponder During Today's Show: What would your perfect day look like if you didn’t have to work tomorrow? Would you be willing to earn less now if it meant retiring five years earlier? What does “enough” look like for you—and how do you know when you’ve reached it? FULL SHOW NOTES: https://stackingbenjamins.com/building-your-early-retirement-plan-1746 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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• Build Wealth AND Community Using This Strategy (with Mel Dorman) SB1745

  What if building wealth wasn’t just about stacking dollars — but also stacking good deeds? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG sit down with Mel Dorman, a powerhouse real estate investor who turned humble beginnings (yes, dumpster diving beginnings) into a thriving portfolio of 34 rental units in just five years. And she didn’t just build wealth — she built community along the way. From negotiating creative seller-financed deals to forging partnerships that benefit both investors and neighborhoods, Mel shares how real estate can be a tool for connection as much as for cash flow. You’ll learn how she leverages relationships, uses alternative financing to scale quickly, and even flips properties without traditional bank loans — all while staying grounded in her mission to help others. But that’s not all: Joe and OG also break down the latest Federal Reserve moves and what they mean for your wallet. And of course, Neighbor Doug drops by with his signature trivia to remind us that building wealth is serious business… but it’s okay to have some fun while you’re at it. What You'll Learn Creative ways to build wealth: How seller financing can unlock deals you never thought possible. The power of purpose: Why combining community impact with real estate investing is a winning formula. Real-world strategies: Mel’s journey from zero to 34 units — and the lessons she learned along the way. How Fed rate changes affect you: What rising (or falling) rates mean for investors and homeowners. Financing myths busted: Why traditional bank loans aren’t the only way to grow a portfolio. Points to Ponder: Could creative financing open doors for your investing goals? How might building stronger community ties improve your financial outcomes? Are you prepared for how interest rate changes could impact your next big money move? This episode isn’t just a guide to real estate success — it’s a reminder that money works best when it works for everyone. Grab a notebook, pour yourself something caffeinated, and join us for a conversation that just might change how you think about wealth building. FULL SHOW NOTES: https://stackingbenjamins.com/real-estate-investing-in-your-community-1745 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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• 5 Life-Changing Money Lessons from Jonathan Clements (SB1744)

  What if the key to a richer life isn’t about chasing the next hot stock or grinding harder — but learning to master the timeless truths of money? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug pay tribute to legendary financial writer Jonathan Clements by revisiting five of his most impactful lessons. These aren’t complicated formulas or secret hacks — they’re the kind of deceptively simple ideas that change the way you think about money, work, and what truly matters. We’ll explore why prioritizing financial stability before passion can actually lead you to a more fulfilling career, how “winning by not losing” may be the most underrated investing strategy of all time, and why patience isn’t just a virtue — it’s a tax strategy. Along the way, we’ll talk about how to strike the right balance between frugality and joy and why living your life may be the best investment you ever make. Plus, we help Stacker Kat tackle a tricky severance situation and share tips on how to put that cash to work without capsizing your financial plan. If you’ve ever wondered how to align your money with a life you actually love, this conversation is the perfect mix of inspiration and actionable wisdom. Grab your coffee mug and settle into Mom’s basement — this is an episode you’ll come back to whenever you need a financial reset. What You'll Learn The real reason you shouldn’t chase passion too soon — and what to do instead How to avoid the most common (and costly) financial mistakes Why patience pays: how time turns taxes into opportunity How to balance frugality with actually living a fulfilling life Smart ways to use severance, high-yield savings, and investing strategies together Points To Ponder: Which of Jonathan Clements’ five money lessons hits closest to home for you? Have you ever faced a tough severance decision like Stacker Kat’s? What did you do? Do you believe financial stability should always come before passion — or is there a time to flip that script? FULL SHOW NOTES: https://stackingbenjamins.com/five-pearls-of-wisdom-from-jonathan-clements-1744 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 Missing Ingredients From Many Financial Plans (SB1743)

  If your financial plan feels more like a vague wishlist than a real roadmap, this episode is about to change that. Live from the basement of YouTube HQ, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long-Term Investors) roll up their sleeves and dig into the three most common — and costly — mistakes people make with their money plans. Whether you’re just starting out or you’ve been stacking for years, this conversation will help you turn “someday” into a solid plan you can actually follow. The gang isn’t just talking theory — they’re breaking down the real reasons plans fail and how to fix them. From adding actionable next steps (instead of endless spreadsheets and good intentions) to weaving in crucial tax and estate planning moves, you’ll discover how to transform your financial plan into a tool that works for you. And because this is Stacking Benjamins, you can expect plenty of banter, relatable stories, and a trivia detour or two along the way. By the time we wrap, you’ll know how to evaluate whether your plan is truly moving you toward your goals, how to communicate more effectively with your financial pros, and how to stop second-guessing every decision. It’s financial planning with fewer headaches, more confidence, and maybe even a little fun. What You’ll Learn Why most financial plans fail — and how to make yours bulletproof The three crucial elements every solid plan needs (and most are missing) How to incorporate tax strategies, estate planning, and real action steps Smart ways to communicate with your advisor or team about what matters most Questions to Consider How to course-correct if your plan’s gone off the rails Does your financial plan include clear, actionable steps — or just big goals? Have you factored in tax and estate planning, or are you leaving those to chance? Are you confident your plan will work in real life, not just on paper? FULL SHOW NOTES: https://stackingbenjamins.com/three-things-missing-from-most-financial-plans-1743 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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