Podcast appearances and mentions of joe saul sehy

You just came into $50,000—no strings attached. Do you crush your debt? Supercharge your retirement? Blow it all on a podcasting-themed backyard grotto? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (The Best Interest) gather around the card table in Mom's basement to tackle one of the most common “someday” questions in personal finance: What do you do when a windfall lands in your lap? Whether it's an inheritance, work bonus, or prize money (maybe you finally won that game show you keep applying to), the panel explores what smart, emotionally grounded, and goal-aligned decisions look like in the face of sudden cash. Start With the Why Before you touch a dime, the crew walks through the importance of mindset, goals, and not falling into the “I deserve it” trap that has sunk many a lucky winner. Debt vs. Invest vs. Enjoy High-interest debt? Retirement accounts? Travel dreams? The panel weighs each strategy—and surprises us with their personal priorities. Behavioral Finance & Windfall Psychology Why do people tend to mismanage unexpected money? From mental accounting to lifestyle creep, learn the hidden traps and how to sidestep them. The 401(k) Match Dilemma Is it better to max out tax-advantaged accounts or build an emergency fund? The team hashes out smart order-of-operations for stacking your windfall right. Trivia Break: St. Paddy's Parade Edition Neighbor Doug makes sure you don't learn too much without a little distraction. Can you guess when the first St. Patrick's Day parade was held? How They'd Spend It Ever wonder what Joe, OG, Paula, or Jesse would do with an extra 50 grand? From practical moves to guilty pleasures, we get a peek into each of their financial brains. Don't let windfalls drift into “found money” syndrome—align with your long-term goals first. Paying off high-interest debt = guaranteed return. But balance it with your future-focused investments. Emotional awareness is just as crucial as spreadsheets when a windfall hits. Take a beat before making decisions. Give yourself permission to enjoy some of the money—just make sure it's intentional, not impulsive. Got a windfall story or dream scenario? Tell us how you'd handle an extra $50K in our Basement Facebook group. Let's see who would invest it, who would renovate the kitchen, and who would finally launch that mobile alpaca petting zoo. FULL SHOW NOTES: https://stackikngbenjamins.com/how-to-treat-a-financial-inheritance-1716 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

High school math left most of us staring blankly at the board, convinced compound interest was just a fancy way to say "confusing." But what if math could be fun, relevant, and—dare we say—life-changing? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome economist, education reformer, and documentary filmmaker Ted Dintersmith to the basement for a conversation that makes math feel less like a chore and more like a cheat code for life. Dintersmith, best known for his education advocacy and the acclaimed documentary Most Likely to Succeed, joins us fresh off the release of his latest book, Aftermath—a compelling look at how we rethink learning in a world that's evolving faster than ever. With over a decade visiting 500+ schools and a deep passion for practical math, Ted shares how skills like estimation, probability, and prediction can help you make smarter decisions—especially when it comes to your money. Why Prediction Beats Perfection Ted explains why being roughly right about your spending, investing, and life planning is more powerful than being precisely wrong. Consumer Math is the Real MVP From family budgets to grocery store run-throughs, Dintersmith makes a case for math that actually applies to your everyday decisions—and shows how parents and educators can teach it at home. A Fourth-Grade Science Test Gone Wrong An unforgettable story about how one exam nearly crushed a curious kid's confidence… and what it says about how we measure learning. The Financial Advisor Dilemma Solved Joe Saul-Sehy and OG unpack the key differences between bank advisors and independents, including fee structures, fiduciary responsibilities, and what really matters when choosing your financial guide. Lights, Camera, Reform Dintersmith shares the powerful stories behind his documentaries—including Most Likely to Succeed and the upcoming Multiple Choice—and why his new book Aftermath is a must-read for anyone who believes education should prepare us for real life. The Psychology of Math Anxiety and Money Mistakes We explore how bad math experiences lead to financial decision paralysis, and how to rebuild confidence one calculation at a time. Neighbor Doug's Trivia Takes the Stage Whether it connects to math or not, Neighbor Doug delivers his signature trivia moment with flair—and possibly a tangent or two. Math shouldn't be a barrier to better money decisions. This episode arms you with a fresh mindset for yourself, your kids, and maybe even your school board. If you're a math teacher, financial coach, or just someone who once cried over fractions, we want to hear from you. Join the conversation in our Facebook group, The Basement, and tell us: How are you making math practical—or how do you wish you'd learned it? FULL SHOW NOTES: https://stackingbenjamins.com/math-that-you-need-in-your-life-1715 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

What if the scariest part of retirement isn't running out of money—but losing your sense of identity? This week on The Stacking Benjamins Show, we tackle the fears that hold so many people back from financial independence and a joyful, purpose-filled retirement. Joe Saul-Sehy and Doug are joined by an all-star panel of financial thinkers: Mark Trautman (Mark's Money Mind) Paula Pant (Afford Anything) Jesse Cramer (Personal Finance for Long-Term Investors) Together, they unpack the emotional, practical, and strategic side of planning your next chapter—whether you're closing in on retirement or still working toward it. The biggest fears about retirement: from running out of money to running out of meaning. The “one more year” syndrome: why it's so tempting to delay and how to break through. Time freedom vs. financial freedom: how to align your life goals with your money strategy. Tactics to conquer fear: income layering, diversified portfolios, annuities, and rental properties. Psychology matters: why no spreadsheet ever solved a midlife identity crisis. Real stories from the panel: wins, struggles, and lessons from guiding others through retirement transitions. Planning for healthcare and long-term care: because your body didn't get the early retirement memo. Plus, the usual basement mayhem: trivia, playful host banter, and a few unexpected laughs (we won't call them “funny”—you know the rule). Mark's Money Mind podcast Afford Anything podcast Personal Finance for Long-Term Investors AARP: Retirement Readiness & Addressing Fear Blog post: “Fear Will Hold You Prisoner. A Diversified Portfolio Will Set You Free.” Retire to something, not just from something. Purpose beats spreadsheets. Understand your income plan. Know where the money will come from, rain or shine. Plan for healthcare now, not later. Medicare, long-term care, and medical surprises deserve your attention. Don't go it alone. The best plans are ones you understand, but it helps to get advice from trusted sources. Whether you're on the cusp of calling it quits or still deep in the grind, this episode will help you prepare—not just financially, but mentally and emotionally—for a retirement you'll love. FULL SHOW NOTES: https://stackingbenjamins.com/what-is-holding-you-back-from-reaching-your-goals-1713 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

What do your financial priorities look like when you're just getting started... or when you're sitting on $100 million? If you're still stuck trying to figure out how to max out your Roth IRA and also afford dinner, this episode's going to walk you through what might be coming next—without promising you a yacht by Tuesday. This week on The Stacking Benjamins Show, Joe Saul-Sehy, O.G., and Doc G (Jordan Grumet) are joined by Nick Maggiulli, Chief Operating Officer at Ritholtz Wealth Management and author of Of Dollars and Data, to talk about lessons from his new book: The Wealth Ladder. Nick breaks down the six wealth levels, from scraping together your first emergency fund to navigating the complexities of generational wealth. They explore: Why increasing your income early on trumps frugality (sorry, coupon clippers). What “wealth plateaus” really look like, and how to recognize when your strategy needs to evolve. The hidden trap of goal obsession, featuring a cameo from world #1 golfer Scottie Scheffler. The true cost of career choices, and why opportunity cost might be the silent killer of long-term growth. Why content and code are two of the most powerful wealth-building levers available (especially when they scale without needing a lunch break). Whether you're stuck in Level 1 or fantasizing about Level 6, this episode has practical, perspective-shifting advice on building wealth—and more importantly, how to enjoy the process without losing your sense of purpose along the way. Stackers don't just want to make money—they want to master it without letting it become their master. This conversation bridges income, investing, identity, and intention in a way that gives you both clarity and confidence. You might even stop worrying about skipping that $5 latte… or realize it's time to start coding that app you keep talking about at parties. FULL SHOW NOTES: https://stackingbenjamins.com/invest-differently-and-move-faster-1712 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

#627: Jlyn and her husband are 20 years from retirement, but they've got their eye on a second home they'll live in when the time comes. Should they make the purchase now, or keep saving? Reese was recently laid off, and she's struggling to choose between two financially responsible paths. Should she continue her long-term disability insurance? Or is it wiser to save money? Kip's youngest has finally graduated from college, and he's looking forward to an early retirement. But, with the eyewatering costs of long-term healthcare, is this still a viable path?  Former financial planner Joe Saul-Sehy and I tackle these three questions in today's episode. Enjoy! P.S. Got a question? Leave it here. Resource mentioned: Reese's original question in Episode 417 Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's the right financial move for you… right now? If you've ever found yourself reading advice meant for a millionaire when you're still trying to crack five figures—or following budgeting tips when your net worth is seven digits—this episode is your custom-tailored financial GPS. In this installment of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Doug take you rung-by-rung through the wealth ladder—from humble beginnings at $10K all the way to $10 million—and explain how your financial priorities, risks, and strategies evolve as your net worth grows. How to avoid mismatched advice: Why taking financial tips meant for someone in a different stage can set you back instead of move you forward. Net worth brackets and behavior shifts: What you should be thinking about at $10K, $100K, $1 million, and beyond—and what not to worry about yet. When Roth IRA conversions make sense—and when they really don't: With new legislation impacting retirement tax planning, Joe and OG break down the implications with help from Robert Powell of The Street. Diversification, risk, and behavioral pitfalls: What the pros get wrong and how to stay grounded no matter how big your stack grows. Community-driven insights: From listener milestones to new Stacking Benjamins swag sightings, you'll hear how Stackers are winning in their own lives. As always, the team weaves in laughter, sarcasm, and that unmistakable basement charm—complete with Doug's new mug, a calendar confusion history lesson, and a household disaster caused by what can only be described as “revenge rain.” A Robin Williams–themed trivia segment to warm your heart (and test your memory) Batty Betty's wild TikTok take on relationship finance Practical investing and estate planning ideas that don't make your eyes glaze over Why You'll Love This Episode:If you're trying to level up without falling prey to the one-size-fits-all advice machine, this episode delivers a realistic blueprint. It's equal parts roadmap and reminder: where you are right now matters more than where someone else thinks you should be. Stacker takeaway? Clarity beats comparison. Especially when it comes to money. FULL SHOW NOTES: https://stackingbenjamins.com/build-your-wealth-ladder-1711 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

Ever feel like you're working hard but getting nowhere? You're not alone—and you might be stuck in a productivity trap, not a purpose-driven plan. In this episode of The Stacking Benjamins Show, we tackle the big one: how to avoid wasting your life. (No pressure.) Joe Saul-Sehy kicks things off with a tongue-in-cheek nod to all the ways we fritter away time—before pivoting into a power-packed conversation on building meaningful goals and avoiding common life derailers. He's joined by two all-star minds in money and behavior: Paula Pant from Afford Anything, who reminds us that "you can afford anything—but not everything," and Jordan Grumet from Earn & Invest, who offers the life-and-death perspective (literally—he's a hospice doctor) on why we need to act now, not later. Together with OG and Doug, the roundtable unpacks six common ways people unknowingly waste their lives, including: Being "busy" instead of effective Letting fear of failure hijack your plans Overthinking every move Paralysis from too many choices Constant hustle with no progress Indecision dressed up as careful planning You'll hear hard-earned lessons, subtle mindset shifts, and tips for creating financial and personal momentum. Plus: The surprising link between indecision and regret, backed by Dr. Ellen Langer's research Smart strategies for eliminating distractions and taking better action The difference between motion and movement—especially when it comes to your goals and your money And, of course, we sprinkle in some classic basement banter, a rowdy trivia throwdown, and Joe's favorite kind of weekend preview (the kind where no one actually follows their own advice). Why this episode is worth your time: Whether you're staring down your 2025 goals or still recovering from a rough Q1, this is your shot of clarity. No judgment—just real talk from people who've been there, made the spreadsheet, and occasionally lit it on fire.

Want to crush your goals and avoid getting crushed by long-term care costs? In today's episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Retired Lieutenant Commander Gary McDermott, a former U.S. Navy officer turned business coach, who brings military-grade discipline to the world of goal-setting and financial success. Whether you're working toward a promotion, launching a side hustle, or just trying to stay on track past February, Gary shares a field-tested, civilian-approved approach to achieving your biggest financial and personal milestones. From defining SMART goals to building sustainable habits and multiple income streams, this conversation is all about real results—no fluff, no buzzwords. But that's just the first mission. In the second half, Joe and OG dive into one of retirement's trickiest topics: long-term care insurance. Is it worth it? When should you buy it? How do you know if it's right for your situation? Consider this your tactical briefing before walking into a battle you didn't know you were fighting. You'll also hear: Why borrowing someone else's goals is a recipe for burnout. The power of structure and accountability (no drill sergeant required). What “Trump Accounts” are and why you might want to know about them. How to evaluate long-term care coverage before it sneaks up on your plan. Joe's high-speed review of the new Formula One movie (spoiler: he's not drafting behind the popcorn). Packed with tactical advice, unexpected laughs, and practical strategies, this episode delivers a full-stack toolkit for Adventurers looking to thrive—financially and personally—in the second half of 2025 and beyond. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Still on track to crush your 2025 goals? Or has the year felt more like a Super Mario Kart banana peel moment? In this special mid-year review episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG take a pause from the summer sprint to look back at the most impactful lessons, conversations, and themes from the first half of 2025. Whether you're rethinking your budget, fine-tuning your risk tolerance, or just trying to remember where you wrote down your resolutions, this is your nudge to hit the financial reset button—with style. From Alex Hormozi's take on embracing risk and skill-building to JL Collins' wisdom on why buying happiness with money is a flawed formula, this episode pulls powerful insights from our brightest guests so far. We revisit career advice from media powerhouse Bonnie Hammer, dig into intentional spending habits, and reflect on the subtle connection between mindset and long-term success. Oh—and don't miss a moment of Joe and OG's always-wise, occasionally-weird banter as they break down topics like: Why goal setting isn't just for January—and how to mid-course correct before December sneaks up on you. Risk management in real life (not the textbook version). Why mindful consumption isn't about cutting back, but tuning in. What makes retirement joyful beyond the spreadsheets. How your community can be the most underrated part of your portfolio. If you've felt a little off-course—or just want a chance to recalibrate without the guilt trip—this episode delivers practical steps and encouraging reminders to help you make the second half of 2025 your strongest yet. Got goals? Let's reset ‘em. And if not, we've got a few ideas for those, too. FULL SHOW NOTES: https://stackingbenjamins.com/our-review-of-first-half-2025-1708 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

#623: An anonymous caller feels trapped in a no-win situation with her financially reckless mother. She has the means to bail her out, but it doesn't feel right. What should she do?  Shannon is excited about investing in several companies overseas. But she can only access them using American Depository Receipts. What are they, and how do they work?  Jennifer calls back with an update on putting a vacation on a credit card and playing the rewards game. Former financial planner Joe Saul-Sehy and I tackle these three questions in today's episode. Enjoy! P.S. Got a question? Leave it here. Learn more about your ad choices. Visit podcastchoices.com/adchoices

DOWNLOAD the FREE Cheat Sheet: ASSET LOCATION MADE SIMPLE at affordanything.com/assetlocation #621: Jared is attracted to the favorable terms of the annuity plan that his employer offers, but he's hesitant to pay the opportunity cost of locking up his money now. What should he do? An anonymous caller is struggling to find the efficient frontier with only three funds to choose from in his Thrift Savings Plan. Is there any hope for him? Jack feels great about the funds in his portfolio, but he's losing sleep over how to apportion them between his taxable, pre-tax and Roth accounts. What's the best tax strategy for him? Former financial planner Joe Saul-Sehy and I tackle these three questions in today's episode. Enjoy! P.S. Got a question? Leave it at https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices

How much can you really spend in retirement without running out of money—or worse, running out of fun? In this deeper-than-usual dive, Joe Saul-Sehy and OG examine the classic 4% retirement rule and whether it's time for an upgrade. With new commentary from Bill Bengen, the original architect of the 4% rule, the team explores emerging research that suggests a withdrawal rate closer to 5.5% might be possible—if you've got the right mix of investments, a solid plan, and a bit of courage. But we don't stop there. Because with greater freedom comes greater risk (especially if you're leading with vibes instead of strategy). The guys tackle the sequence of returns risk that can derail early retirement years, and how to build a portfolio that helps you sleep at night—even during a market storm. Meanwhile, Doug drops in with an unexpected (and very British) culinary experience, Joe fields a listener question comparing financial plans to workout routines (is your Roth IRA doing enough reps?), and yes... we revisit our fan-favorite segment on how food waste is wrecking your budget. Why the 4% rule might be too conservative (or maybe just outdated). What diversified portfolios and asset class strategy have to do with a longer-lasting nest egg. How to prepare for market downturns before they happen—and what to do if you're already in one. Why retirement joy isn't just about spreadsheets—it's about the psychology of spending with confidence. Which type of green tea is the superior kind (depending on which side of the TikTok aisle you're on). How to reduce food waste and put that extra savings toward your bigger financial goals. If you're approaching retirement—or even just dreaming about it—understanding how much you can safely spend without sabotaging your future is the question. This episode combines historical insight with today's market realities to give you the real math and mindset you need to retire well…and maybe even with a smile. FULL SHOW NOTES: https://stackingbenjamins.com/problems-with-the-4-percent-rule-1702 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

Families are making plans for Fourth of July road trips, choosing cars over planes for everything from camping weekends to family reunions. Car travel remains the top choice for summer getaways but rising prices have prompted more travelers to look for ways to stretch every dollar, especially when traveling with kids, grandparents and maybe even … Continue reading Joe Saul-Sehy, Summer Road Trips and Sports Travel →

Can you really build wealth with a simple formula? Do you need a budget to succeed financially? Should you cut up all your credit cards, or is that just a dramatic TikTok trend? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy is joined by Paula Pant, Doc G (Jordan Grumet), and Jesse Cramer for a roundtable discussion that peels back the truth behind popular advice from so-called financial “gurus.” The conversation is rooted in a provocative blog post by Christine Luken that calls out four common money mantras—and the team dives into each one with classic basement wit, spirited debate, and hard-earned wisdom. Topics on the table: Do you really need a budget, or can you thrive without one? Are rigid financial formulas helpful or harmful? Is willpower the key to financial success—or just a scapegoat? Does cutting up credit cards actually solve your spending problems? Along the way, you'll hear banana jokes (yes, multiple), a heated trivia contest about obsolete technology (looking at you, LaserDisc), and some good-natured trash talk that might just surprise you with how insightful it gets. This episode is packed with nuance, laughs, and practical takeaways for Stackers who are tired of the one-size-fits-all guru approach. Whether you're team budget or team spreadsheet freestyle, there's something here for you—plus a solid reminder that when it comes to personal finance, the best advice is the advice that fits your life. FULL SHOW NOTES: https://stackingbenjamins.com/lies-damn-lies-and-statistics-1701 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

Joe Saul-Sehy is talking travel on this edition of the MADM. Sponsor: Premier Structures PremierStructures.com

On this edition of TMWS, we are talking travel with Joe Saul Sehy and backpack giveaways with Lane Harper of the Power of Life Foundation!

What's the best way to save for a house without wrecking your retirement plan? That's just one of the big questions Joe Saul-Sehy, OG, and Mom's neighbor Doug tackle in this packed episode (number 1700!) of Stacking Benjamins. Whether you're trying to figure out where to park your emergency fund, how to handle inherited IRAs, or how to financially plan as a single adult with big responsibilities (hello, aging parents!), this episode is full of relatable scenarios and actionable strategies. Stackers Torin, VJ, Lori, and Michelle ask everything from: How much is too much in your emergency fund? What happens to inherited IRAs when you're already juggling financial priorities? What should single people be doing right now to prepare for the future? How do you juggle helping aging parents while keeping your own goals on track? Plus, we mix in commentary from Kevin at Edward Jones and longtime listener Ron—offering insights from inside the financial services world and the Stacker community. The guys debate personal finance media narratives, give practical advice for budgeting large windfalls, and reflect on why saving feels easier in theory than in practice. Also covered in this episode: Why financial advice often skips over single individuals—and what to do about it Emergency fund strategies: where to park the money, how much to keep, and how to make peace with the fact it isn't earning sky-high returns How to prioritize debt, student loans, savings, and investing without setting off a financial anxiety spiral The value of short-term tradeoffs when you've got long-term goals All delivered with the basement's signature charm—where the coffee is lukewarm, the guidance is practical, and the jokes… well, let's just say they're dividend-eligible. This episode is a perfect listen for: New Stackers building their financial foundation DIYers trying to juggle competing money goals Anyone who's inherited assets and doesn't want to mess it up People who've realized adulting is basically managing 14 financial priorities at once and still remembering to bring snacks. FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-questions-mailbag-1700 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

#619: Dave is no longer happy with his financial advisor, but he's nervous about switching over to self-management after being completely hands-off for so long. What should he do? An anonymous caller keeps hearing about the benefits of Cost Segregation for investment property. What is it? And should he apply this strategy to his recently acquired duplex? Another anonymous caller is eagerly anticipating a windfall from his employer's upcoming IPO. How should he prepare for this, and what happens if it fails? Former financial planner Joe Saul-Sehy and I tackle these three questions in today's episode. Enjoy! P.S. Got a question? Leave it at https://affordanything.com/voicemail For more information, visit the show notes at https://affordanything.com/episode619https://affordanything.com/episode619 Learn more about your ad choices. Visit podcastchoices.com/adchoices

The robots aren't just coming—they're already here. And if you're not paying attention, they might not just take your job… they could take your personal data too. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Doug dive into the rise of artificial intelligence, exploring whether it's a threat, a tool, or something in between. If you've been wondering how AI will impact your work, your privacy, and your future, this episode is a must-listen. They kick off with a surprising headline: Gen Z workers are sidestepping AI entirely—not by resisting it, but by choosing careers where machines can't compete (like landscaping and trades), and using AI tools to grow their businesses faster. This sparks a full-on basement debate about how technology has historically impacted jobs, what the next evolution might look like, and whether AI will make our lives easier… or just busier. In today's show: Why some jobs may disappear—but others are about to explode with opportunity The surprising role AI is playing in blue-collar and skilled trade growth Why being AI-curious (not AI-phobic) is your best financial move New tech tools that supercharge productivity—from transcription wallets to note-taking bots How AI is already transforming education and career paths What to do right now to stay ahead of the AI curve Then the guys shift gears to a more sinister topic: data privacy. CNET recently reported which free AI chatbots are scooping up the most of your personal info—and which are surprisingly respectful. The gang reveals which apps are best to trust, and which are like letting Zuck crash on your couch (bad idea). We'll also hear from listener John, who wants to hire a financial advisor but isn't sure where to start. Joe and OG break down how to find the right fit, why fees aren't the most important factor, and the one question that tells you if someone's worth hiring. Plus: Doug's trivia on egomaniacal coin designers A TikTok minute about U2, dating apps, and dad jokes Back porch chatter about Pontiac Azteks, water treatment careers, and IMAX concert pilgrimages Takeaway: AI isn't just a tech trend—it's reshaping our economy, our careers, and even how we learn. Whether you're a Gen Z worker, mid-career professional, or planning your retirement, now's the time to lean in, explore what AI can (and can't) do, and secure your future before the bots beat you to it. FULL SHOW NOTES: https://stackingbenjamins.com/ais-coming-for-your-job-how-to-outwit-the-robots-1699 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

So you've scaled the mountain, built the nest egg, and maybe even shouted “I'm done!” across a pristine beach... now what? In today's Stacking Benjamins episode, Joe Saul-Sehy convenes a roundtable of heavy-hitters to tackle the most misunderstood phase of money management: decumulation—a.k.a. the art of spending what you've worked so hard to save. Whether you're staring down retirement or already deep into your golden years, you'll hear candid, practical insights from three financial thought leaders who specialize in making your money last. Joining Joe are Dana Anspach, retirement planning expert and founder of Sensible Money, Karsten Jeske (aka “Big ERN” from Early Retirement Now), and Frank Vasquez, aka Uncle Frank, host of Risk Parity Radio. Together, they bring decades of academic research, professional experience, and plain old common sense to questions like: What's the real safe withdrawal rate—and why does it depend on more than just spreadsheets? Should you chase simplicity or embrace complexity in managing retirement funds? What role do annuities and guaranteed income play in reducing late-life anxiety? How do you plan for cognitive decline without spiraling into existential dread? What's the difference between spending confidently... and spending carelessly? You'll also hear why lumpy expenses, long-term care surprises, and behavioral quirks can trip up even the best-laid plans—and how to bulletproof your strategy now. And yes, we get nerdy. Risk parity, sequence of return risk, and portfolio glidepaths all make guest appearances—but always with your favorite Stacking Benjamins charm and plain-English style. Because retirement doesn't need to be scary... but it does need to be intentional. Why your investment approach needs to evolve once paychecks stop The strengths and blind spots of the “4% rule” How emotions (not just inflation) affect safe withdrawal strategies When it makes sense to annuitize, and when it absolutely doesn't How to adjust for cognitive decline in your financial plan (and still maintain autonomy) The “spend conservatively early” myth—debunked Tips for managing healthcare and other unpredictable late-life costs Whether you're a retiree, a pre-retiree, or a spreadsheet-loving financial independence buff, this deep-dive episode will give you the confidence to manage the second half of your financial life like a pro. This isn't just about stretching your dollars—it's about building a life worth spending them on. So grab your planner, pour a cup of whatever says “retirement-ready” to you, and let's get smarter (and maybe just a bit weirder) about your golden years. FULL SHOW NOTES: https://stackingbenjamins.com/create-your-retirement-spending-plan-1698 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

What if the most important part of your retirement plan had nothing to do with your 401(k), IRA, or stock portfolio? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by filmmakers Pete Davis and Rebecca Davis, creators of the thought-provoking documentary Join or Die. They explore how community connection, not cash, may be the ultimate retirement strategy. Drawing inspiration from the late political scientist Robert Putnam (Bowling Alone), the Davises reveal why joining groups—book clubs, church choirs, rec leagues, neighborhood associations—might be more essential to your long-term well-being than your asset allocation. Together with Joe and OG, they unpack the data behind social decline, the healing power of showing up, and what the film Join or Die teaches us about leading a richer life beyond the numbers. Of course, Mom's Neighbor Doug pops in with trivia that proves he belongs (at least to this show). Whether you're on the path to retirement or simply looking for deeper purpose, this episode will make you think differently about how you stack your most valuable resource: time. Why joining a club may be just as critical to retirement as saving for it What Join or Die reveals about America's shrinking social networks How loneliness affects physical and financial health—and how to fight it Why your “portfolio of community” might be the highest-yield investment you ever make Ways to build meaningful connections now—even if you don't feel like a “joiner” Pete and Rebecca Davis share behind-the-scenes stories from making Join or Die Joe and OG reflect on what gives life meaning after the 9-to-5 ends Surprising data on the link between social capital and financial confidence Doug delivers a trivia challenge about famous clubs (and less-famous neighbors)

Jesse explores the value of financial priorities and the balance between spending and saving with guests Diania Merriam, Justin Peters, Bill Yount, Jeremy Schneider, Doc G, and Joe Saul-Sehy. Diania highlights the “iceberg principle” of stealth wealth—how true wealth is often what you don't see, like deferred purchases and unspent money. Justin shares a personal story about the cost and memories of boat ownership, emphasizing the lesson to buy utility and rent luxury. Bill discusses the different seasons of life in relation to frugality and spending, while Jeremy reflects on ingrained money habits persisting despite sudden wealth. Doc G and Joe Saul-Sehy add their unique perspectives on personal finance and the emotional relationship with money. Together, they unpack how financial decisions shape our lives, the importance of aligning spending with values, and the lessons learned from both scrimping and splurging. Key Takeaways: • Financial freedom doesn't always come with a clear sense of how to enjoy money meaningfully. • Renting luxury experiences can be more satisfying and economical than owning them. • Time, health, and family often become more valuable than money as people grow older. • Community and shared experiences often bring more satisfaction than expensive possessions. Lifestyle upgrades need to be aligned with personal values to feel meaningful. • Former spendthrifts can struggle just as much with letting go of financial vigilance. • Understanding your money story is key to shifting your habits and mindset with intention. Even the financially savvy can be blindsided by lifestyle creep and emotional spending. Key Timestamps: (00:00) – Scar Tissue: Financial Lessons from the Past (13:59) – The Mini Bar Mishap (20:11) –  The $500 Parking Ticket (23:56) – Balancing Financial Optimization and Enjoying Life (24:29) – Time vs. Money: Changing Priorities (25:50) – Keeping Up with the Joneses: A Personal Story (30:59) – The Perils of Consumerism and Stealth Wealth (44:12) – Rent Your Luxury and Buy Utility (45:20) – Frugality Habits: From Broke to Millionaire Key Topics Discussed: The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques Bill Yount:  Website: https://catchinguptofi.com/ LinkedIn: https://www.linkedin.com/in/bill-yount-a8033036/  Diania Merriam: Website: https://economeconference.com/about/ LinkedIn: https://www.linkedin.com/in/dianiamerriam/  Justin Peters:  Website: https://podcasts.apple.com/us/podcast/fi-minded-achieve-financial-independence-have-fun-doing-it/id1496701179 LinkedIn: https://www.linkedin.com/in/justinleepeters/  Jordan (Doc G) Grumet:  Website: https://jordangrumet.com/ LinkedIn: https://www.linkedin.com/in/jordan-grumet-38a506179/  Joe Saul-Sehy:  Website: https://www.stackingbenjamins.com/ LinkedIn: https://www.linkedin.com/in/joe-saul-sehy-b3426b31/  Jeremy Schneider: Website: https://www.personalfinanceclub.com/ LinkedIn: https://www.linkedin.com/in/jerschneid/  More of The Best Interest: Check out the Best Interest Blog at bestinterest.blog Contact me at jesse@bestinterest.blog The Best Interest Podcast is a personal podcast meant for education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

#617: Austin and his wife are worried about moving to a single-income household while supporting two kids. Should they free up cash flow by paying off a car loan, or tighten up and stay the course? Paul has been retired for seven years, but still can't shake his anxiety about not having enough. Is there a good way to know when he's finally escaped the dreaded sequence of returns risk? Jonathan wants to build up his taxable brokerage account, but he's having trouble letting go of the tax benefits of a Roth IRA. How does he get past his psychological hurdles? Former financial planner Joe Saul-Sehy and I tackle these three questions in today's episode. Enjoy! P.S. Got a question? Leave it at https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices

You can't plan a great retirement if you haven't first planned what you're retiring to. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug open up Retirement Week in the basement with a Monday that's equal parts insight, weekend recap, and questionable vehicle decisions.

Markets crashing? Interest rates spiking? Inflation roaring? Welcome to history. This week, we dig into 130 years of stock market meltdowns—from the panic of World War I to the Great Depression, 1970s stagflation, the dot-com collapse, and the 2008 financial crisis—to uncover timeless lessons that can fortify your financial future. Joe Saul-Sehy is joined by Miranda Marquit, Jesse Cramer, and OG to examine how investors have historically responded to chaos... and how you should, too. You'll learn why diversification matters, why panic rarely pays, and why staying the course (even when it's scary) can be the smartest move of all. Of course, this wouldn't be the Stacking Benjamins Show without a trivia detour that involves mailing children through the U.S. Postal Service (yes, that happened). Buckle up for laughter, insight, and financial takeaways that are as practical as they are entertaining. What WWI, the Great Depression, and 1970s inflation can teach us about investing Why “The Lost Decade” wasn't a loss for long-term thinkers How to build a resilient portfolio that weathers the storm Our infamous trivia game: How much could a kid weigh and still be legally mailed in the 1920s? A few money-saving hacks, podcast updates, and your weekend preview from the basement Whether you're a seasoned investor or just building your financial foundation, this episode will leave you smarter, more confident, and—let's be honest—way more amused than the average market history lecture. FULL SHOW NOTES: https://stackingbenjamins.com/lessons-from-stock-market-history-1695 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

What happens when you mix financial strategy with a healthy dose of cultural commentary? You get Rich Girl Nation. This week on The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Katie Gatti Tassin, the powerhouse behind Money with Katie and author of the new book Rich Girl Nation. Together, they unravel the sneaky ways consumerism shows up in our lives—from pricey trends to status-signaling spending—and how it messes with our wallets. Katie dives into the “hot girl hamster wheel” of overspending, the wage gap, and why negotiating your salary (without flinching) is one of the best financial moves you can make. She also offers sharp, tactical advice on job-hopping for higher pay and automating your money to avoid lifestyle creep. Meanwhile, the crew throws in real-life stories, from Cybertruck depreciation to celebrating financial independence in more ways than one. And of course, Doug drops in with a trivia twist that keeps things weird—because it wouldn't be the basement without a little curveball.

#615: Emily is nervous that buying their first home will derail her family's journey to financial independence. What's the smartest way to deploy their savings and stay on track? Based on cap rate calculations, Paul's real estate investments have appreciated beyond their sensible holding point. Should he sell his assets, or is there more to consider here? Mike is recently retired while his wife still works. With a paid-off home and healthcare already taken care of, what are best practices for drawing down an investment portfolio?   Former financial planner Joe Saul-Sehy and I tackle these three questions in today's episode. Enjoy! P.S. Got a question? Leave it here. For more information, visit the show notes at https://affordanything.com/episode615https://affordanything.com/episode615 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Can building wealth be as entertaining as a round of trivia in the basement? We think so—and today's episode proves it. Joe Saul-Sehy is joined by Doc G, Paula Pant, and Jesse Cramer to play a fast-paced financial game show based on 11 expert-approved ways to grow your wealth. From boosting your income and dialing in your budget to the eternal tug-of-war between paying down debt and investing more, this episode delivers wisdom with a side of basement-brand chaos. But we don't stop at just the basics. Our roundtable dives into: How homeownership plays into your wealth picture (even if it's not as sexy as index funds), Why insurance coverage might be your best wealth-preserving move, The truth about improving your credit score without obsessing over every point. Plus, a trivia celebration of 50 Cent's Vitamin Water payday turns into a lesson in surprise wins—and surprise losses. Whether you're just beginning your wealth-building journey or refining your strategy, this episode brings practical insights, hearty laughs, and a gentle nudge to rethink what really grows your net worth. How to increase your income (without selling essential organs) Budgeting strategies that actually stick Why investing early matters—and when paying off debt takes priority The real ROI of proper insurance coverage A homebuying debate that might ruffle some financial feathers Birthday trivia for 50 Cent and the Vitamin Water deal that made him a legend End-of-episode takeaways you'll want to write down (or tattoo, if that's your thing) Stackers, whether you're navigating rainy days or planning for a brighter financial future, today's conversation will help you stack smarter, live better, and maybe even walk away with a new strategy—or at least a smile. FULL SHOW NOTES: https://stackingbenjamins.com/our-favorite-ways-to-grow-wealth-1692 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

In this episode, I reconnect with my old friend Joe Saul-Sehy from The Stacking Benjamins podcast to talk about creating your own life curriculum — because when you do, you may no longer be beholden to anyone. With AI eliminating jobs and making the path to financial independence even tougher, I wanted to sit down with another creator who forged his own way—building a business and income stream through podcasting. I firmly believe everyone should build an online brand and develop a side hustle. The era of job security, pensions, and abundant opportunities is fading. You—and your children—need to learn how to create your own income streams. Check out Joe's work at: https://joesaulsehy.com https://www.stackingbenjamins.com Subscribe To Financial Samurai Join 60,000+ others and subscribe to the free weekly Financial Samurai newsletter. My goal is to help you achieve financial freedom sooner, rather than later. Financial Samurai started in July 2009 and is the leading independently-owned personal finance site today.  This episode is sponsored by Fundrise Venture, an innovative venture capital product that invests in private AI companies like OpenAI, Anthropic, Anduril, Databricks, and more. The minimum investment to start is only $10, and I personally have invested over $185,000 in Fundrise Venture so far.   

After Monday's primer on why your portfolio needs some international flavor, we're following up with a deeper dive—this time with someone who lives and breathes global markets. Joe Saul-Sehy and OG welcome Joy Yang, Head of Index Product Management at MarketVector Indexes, to talk through how to actually invest beyond U.S. borders. Joy explains how ETFs can help investors capture international growth while minimizing risk—and why country-specific and sector-specific ETFs might just be your new best friend. You'll also hear insights on investing in private markets, the rise of digital assets, and whether private equity in your 401k is a brilliant idea… or a cautionary tale. But don't worry, the basement stays weird. Doug brings the trivia heat with a Martha Stewart–Eliot Spitzer stumper, and the episode wraps with some creative audience feedback (including one Stackers' AI-powered school project that caught our attention). Topics Covered: How to diversify globally without overcomplicating your portfolio The power of ETFs for targeting specific markets and sectors What you really need to know before considering private equity in retirement accounts Balancing simplicity with opportunity in a world of shiny investment options The limits of “going big or going home” when it comes to risk and return Stackers, if you're looking for smart ways to expand your portfolio's reach—or just curious what index creators think about Bitcoin—this episode delivers insights, laughs, and a grounded reminder: simple can still be smart. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-invest-globally-with-joy-yang-1691 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

How global is your portfolio, really? This week in the basement, Joe Saul-Sehy, OG, and the gang zoom out from the U.S. markets and take us on a whirlwind trip around the investing world. Spoiler alert: the case for international investing is stronger than you think—and it's not just about chasing higher returns. It's about risk reduction, smart diversification, and maybe even admitting that the U.S. isn't always the world's MVP. You'll hear how developed and emerging markets fit into a well-balanced portfolio, how correlation works in your favor (yes, this time that's a good thing), and what history tells us about going global. Joe and OG share practical advice for how to get started, when to rebalance, and how much international exposure might make sense for the average Stacker. Then in the second half, we pivot from markets to money buffers: listener Jeff from Cleveland wonders how to set insurance deductibles based on the state of his emergency fund. We break down how to think about the real return on your rainy-day stash—because spoiler: it's not about the interest rate, it's about your resilience. To wrap things up, we share timeless wisdom from Stackers across the country on what they'd tell new graduates about money, life, and how not to blow that first paycheck on a jet ski. Why international investing may improve both your returns and your risk profile How much of your portfolio to allocate internationally—and what history suggests What "correlation" really means and why it's your friend (at least in investing) Risks and common misconceptions of investing overseas How to choose between developed vs. emerging markets Portfolio tools to visualize your asset mix and expected outcomes Why your emergency fund's best ROI might be peace of mind How to align insurance deductibles with your liquidity cushion What our community of Stackers wishes they had known after graduation FULL SHOW NOTES: https://stackingbenjamins.com/making-the-case-for-international-investing-1690 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

#611: With the state of the world changing so rapidly, Lesley is struggling to accept that “this time isn't different.” Does the past still reliably inform the present in the face of major decisions today? An anonymous caller and her husband want to achieve financial independence through real estate within 10 years. Is it better to pay off existing mortgages or prioritize buying more rentals? Melanie feels duped by the FICO credit scoring system. She's doing all the right things, but her credit score is still moving in the wrong direction. What's going on here? Former financial planner Joe Saul-Sehy and I tackle these three questions in today's episode. Enjoy! P.S. Got a question? Leave it here. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Think you're being lied to at work? You probably are. From boardrooms to bank accounts, this episode pulls no punches. We're stacking double the wisdom on this special Memorial Day episode, as Joe Saul-Sehy interviews two powerhouse guests: Bonnie Hammer, former vice chair of NBCUniversal and bestselling author, and Dr. Erika Rasure from Beyond Finance. Whether it's breaking glass ceilings or breaking out of debt, this episode is your roadmap to reclaiming control. Inside the episode:

Memorial Day weekend is here, which means it's officially time to break out the grill, the beach bag… and maybe that travel budget spreadsheet. But don't worry—this isn't a guide from travel influencers who hike barefoot with artisanal backpacks. Nope. This episode is brought to you by your favorite money geeks in Joe's mom's basement. Joe Saul-Sehy, OG, Jesse Cramer, Crystal Hammond, and Doug gather 'round the card table to share their best budget-friendly travel strategies, hilarious vacation stories, and maybe one or two travel fails. From choosing the right travel companion to navigating airports like a boss, this crew drops loads of practical wisdom for making your summer adventures awesome and affordable. You'll learn why credit card points can be your best friend, how to pick lodging that won't make you cry (or bankrupt you), and why packing a toothbrush is a good idea… even if Doug's trivia makes you question the timing. This isn't expert advice. These are the musings of people who spend more time optimizing their wallets than their luggage. And that's exactly why you'll leave feeling better prepared to tackle your own summer travel—without the jet-setter guilt trip. Kicking off summer with a Stacking Benjamins travel roundtable Real-life travel hacks from people who care more about budgeting than boarding groups Credit card point strategies that actually work Hot takes on hotels, Airbnbs, and airport snacks Why picking the right travel buddy can make or break your trip The one item Doug thinks was more important than nylon (it's… something) Whether you're headed to the lake, the mountains, or just your backyard with a cold drink, join the crew for a hilarious and practical celebration of summer travel. 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

What do cupcakes, frosting, and financial independence have in common? This week in the basement, Stacking Benjamins welcomes legendary personal finance thinker JL Collins, author of The Simple Path to Wealth, to connect the dots between simple investing and sweet, stress-free success. In a lively conversation with Joe Saul-Sehy, OG, and Mom's neighbor Doug (who may or may not be launching a frosting-themed protest movement), JL shares timeless wisdom on avoiding complexity, embracing low-cost index investing, and why FU money is more than just a clever phrase—it's freedom in a bank account. You'll hear JL's take on portfolio allocation, debt's sneaky impact on your future, and how to survive volatile markets without sacrificing your peace of mind. If you've ever felt stuck in a soul-crushing job? JL's got some perspective you'll love. Then, in the second half of the episode, Joe and OG shift gears to answer a listener question from Mike. He's wondering about the efficient frontier—yes, we're getting fancy now—and wants to know how to move beyond the Simple Path. Joe walks through the different asset classes he thinks about when crafting a diversified portfolio, while OG shares how to think through asset allocation as your wealth and confidence grow. Whether you're curious about real estate, international investing, or just how much to hold in bonds, you'll walk away with a clearer picture of what your portfolio could look like after “graduating” from JL's foundational advice. Why keeping it simple beats chasing trends What “FU money” really means—and how to get it The truth about withdrawal rates and why they matter When debt becomes a dream killer Tips for navigating market downturns without panic How to find freedom without spending a fortune JL's surprisingly profound parable about a monk, a minister, and money Doug's hot take on the great frosting vs. cake debate A deep dive into the efficient frontier and how to set up your asset allocation beyond VTSAX Joe Saul-Sehy and OG's thoughts on portfolio construction for seasoned investors JL's insights have inspired millions on the path to financial independence—and now it's your turn. Tune in, take notes (or don't, we'll recap it in the 201), and remember: sometimes the sweetest success starts with doing less. 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

Eva is approaching financial independence, but she's worried about messing up the transition. How does she set her portfolio up for success during the drawdown years of early retirement? Former financial planner Joe Saul-Sehy and I deep-dive into this question in today's episode. Enjoy! P.S. Got a question? Leave it here. Episodes about the Efficient Frontier: https://affordanything.com/577-qa-the-efficient-frontier-was-perfect-until-hr-got-involved https://affordanything.com/357-practical-investing-and-the-efficient-frontier-with-joe-saul-sehy https://affordanything.com/380-ask-paula-how-to-optimize-your-investments-along-the-efficient-frontier-if-you-dare https://affordanything.com/episode597 https://affordanything.com/episode567 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Is it summer already, or is that just our theme park budget melting in the sun? Either way, we're kicking off the season with our annual guide to roller coasters, churros, and how not to hurl after one too many loops. Theme Park Insider's Robert Niles returns to share the biggest news in amusement park land—from a new Disney park in Abu Dhabi (what?!) to Universal Orlando's game-changing Epic Universe. But what's a summer kickoff without a good ol' whiplash reminder that your brain can't be trusted when it comes to investing? Joe Saul-Sehy and OG dive into Jason Zweig's latest insights about how our market “memory banks” mess with decision-making, and why 2008 probably wasn't as scarring as your gut tells you. And yes, Doug's trivia ties it all together—with corn dogs, naturally. How to actually save money at theme parks without having to sleep in a costume closet. The surprising reason a $1,400 day at Disney might be your own fault. Which new coasters (and old favorites) are worth the detour this year. Why your gut—and your "market memory"—could be sabotaging your investments. The last time the stock market went down multiple years in a row (hint: not 2008). What Robert's favorite underrated U.S. parks are (spoiler: Dollywood shows up, again). How to strategically splurge or save at the parks—merch fans, avert your eyes.

What really moves the needle on your happiness—making more money or saving more of what you've got? This week, Joe Saul-Sehy and OG are joined by Paula Pant, Jesse Cramer, and the guy who still owes money on his Beanie Baby collection—Doug—for a roundtable filled with bold financial takes and even bolder choices. It's a rapid-fire round of “either-or” dilemmas, and while nobody gets voted off the island, a few sacred cows are gently tipped over. Should you max out your retirement account or finally slay your student loans? Ditch credit cards for cash? Bet your future on crypto or keep it stuffed in a fireproof mattress? Our panel debates these decisions and shares real-life stories of what's worked—and what's blown up like a microwaved burrito. Of course, it wouldn't be The Stacking Benjamins Show without a detour or two: we dig into financial hoarding (how many dusty envelopes is too many?), reveal why your credit score might be your best frenemy, and serve up some vintage airplane trivia, just to keep things classy. So whether you're team "Earn More" or team "Cut Back," this episode delivers the kind of guidance that helps you feel a little more confident making your next money move—even if it's just saying no to another financial “shortcut.” Topics covered include: Why more income might not be the golden ticket The case for ditching your credit card (and why that makes Doug twitchy) Saving vs. investing vs. spending like you're already retired What financial hoarding reveals about your mindset Index funds vs. individual stocks: which one should get your long-term commitment? The never-ending crypto debate (now with 12% more existential dread!) How obsessing over your credit score may or may not ruin your weekend If you're figuring out how to balance today's latte with tomorrow's freedom—or you just want to feel smarter about money than your cousin Gary who “invests in vibes”—this one's for you. And remember, no matter how much you earn or save, the real ROI is tuning in with the Stackers each week. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Ever feel like money is a never-ending game of not enough? Today, we're rewiring that thinking. Our special guest, Leisa Peterson—author of The Mindful Millionaire and now The Money Catalyst—joins us to talk about abundance, scarcity, and how to stop living life like you're budgeting for armageddon. (Hint: It's okay to order the nice wine now.) Joe Saul-Sehy and OG also shine a light on the resurgence of alternative investments. Is it innovation... or just Wall Street's way of sneaking in high fees through the back door? Plus, we roll into Doug's trivia, a TikTok Minute that flips the script on a certain “draft pick,” and, of course, a few stories that prove—yet again—that golf is no game for the frugal. “Am I YOLO-ing or just broke?” Why framing matters more than frugality From scarcity to satisfaction: How one moment in Paris changed Leisa's relationship with money You call that a tip? The surprisingly deep conversation behind street musicians, champagne, and generosity Alternative investments are back (again?) Why your advisor might pitch you on ditching the market... and why you should think twice Personal growth through fiction: Leisa's surprising journey from nonfiction burnout to a book that might just fix your wallet and your heart When the camel arrives with a skeleton on its back: Doug's trivia gets weird (and somehow financial) TikTok Minute: What happens when a 50-year-old thinks he just got drafted into the NFL OG's rule of thumb: Volatility isn't the villain—it's the entrance fee

#607: George is a worried baby boomer, wondering if today's generation is drowning in the noise of today's financial landscape. How does one find a balance between information and overload? Heather is stunned by the notion that renting could make more financial sense than buying. Where she's from, the numbers seem to always swing in favor of owning. What's she missing? Former financial planner Joe Saul-Sehy and I tackle these questions in today's episode. Enjoy! P.S. Got a question? Leave it at https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do most millionaires have in common? No, it's not a yacht named “Compound Interest.” It's mindset. In this episode, Joe Saul-Sehy and OG kick off Mindset Week by welcoming Sam Dogen, the Financial Samurai himself, to help you start your journey toward a million-dollar net worth—one intentional step at a time. Sam shares why building wealth is less about luck and more about grit, clear goals, and a killer savings rate. He explains why $250,000 is the magic milestone where compounding takes over, why your “why” is more important than your budget, and how a simple house-to-car ratio can reveal whether you're cruising toward financial freedom or stuck in the valet lane. You'll learn: Why your first $250,000 is the hardest (and most critical) How to find your “why” and let it drive your money decisions Why some people crush millionaire goals while others stall out The pros and cons of prioritizing student loan payoff How real estate, entrepreneurship, and mindset play a role in long-term success Plus, Doug delivers trivia about the world's most millionaire-dense country (hint: it's not the U.S.), and Joe announces a live event with Boldin's Steve Chen to help you master retirement planning tools. All that and a wink toward OG's dream car obsession (which definitely didn't come from the after-show... wink wink).

If your grocery bill has you doing double-takes at the checkout line, you're not alone—and this episode of The Stacking Benjamins Show is packed with practical ways to take control of your food spending. Joe Saul-Sehy is joined by Janice Torres of the Yo Quiero Dinero podcast, regular contributor OG, and the always-frugal Len Penzo to serve up real-world grocery hacks that help you stretch your dollars without skimping on flavor or quality. You'll learn: How meal planning can shrink your bill (and your food waste) When buying in bulk pays off—and when it's just a trap Why pre-packaged foods might be eating up your budget Which apps help you unlock store discounts and cash back And whether starting a garden is actually worth it for your bottom line We also dig into freezer strategies, the art of cutting back on meat without feeling deprived, and a few guilty pleasure restaurants that somehow always find their way back into our budgets. It's a money-saving roundtable that's equal parts helpful and hilarious. Come for the grocery hacks, stay for the side dishes of personality. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

#605: In light of recent federal mandates to return to the office, Pedro is having a hard time giving up on his fully remote lifestyle. Is there a creative solution to his dilemma?  An anonymous caller is excited to move abroad permanently. How should she structure her investments to support her international lifestyle while maintaining a home base in the US? Former financial planner Joe Saul-Sehy and I tackle these questions in today's episode. Enjoy! P.S. Got a question? Leave it at https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices

Joe Saul-Sehy sits down with bestselling author Jen Sincero, the powerhouse behind You Are a Badass and You Are a Badass at Making Money. If you've ever felt stuck in financial quicksand or caught in a loop of scarcity thinking, Jen brings the fire (and the funny) to help shift your mindset and start building wealth from the inside out. You'll hear: How Jen went from living in a garage to becoming a seven-figure entrepreneur The mindset shifts that changed her relationship with money—and could change yours Why self-talk and affirmations aren't fluff—they're your financial launchpad Simple ways to start reprogramming how you think, spend, and save The importance of consistent investing—even when you're not feeling confident We also touch on: Why your HSA might be a secret investing weapon What to know as tax deadlines approach (and how not to panic) A listener's creative approach to investing—and how OG and Joe weigh in Plus: marathon filming, TV mishaps, and trivia surprises from Mom's neighbor Doug If you're ready to stop playing small with your money and start stacking like a badass, this episode will give you the mindset—and motivation—to get going. FULL SHOW NOTES: https://stackingbenjamins.com/you-are-a-badass-at-making-money-greatest-hits-week-1678 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

Buying vs. renting: it's one of the most emotionally charged—and financially misunderstood—topics in personal finance. This week on The Stacking Benjamins Show, Joe Saul-Sehy, OG, and guests Jesse Cramer and Chris Luger enter the ring to challenge the conventional wisdom behind homeownership. It's not just a polite chat. It's a full-on basement debate where no side goes unchallenged. You'll hear: The surprising math behind renting—and why it's not “throwing money away” What most homeowners don't budget for (and pay dearly for later) Why buying a house might be one of the best—or worst—decisions you ever make How lifestyle, mobility, and flexibility factor into long-term wealth The emotional traps, practical benefits, and tough tradeoffs on both sides Plus, Mom's neighbor Doug gets into full trivia-host mode with a Star Wars challenge, and we sprinkle in some good-natured jabs, marketing wisdom, and a reminder that there's no one-size-fits-all answer. If you've ever bought a home, sold one, rented, or even thought about doing any of the above—this episode will make you think twice. FULL SHOW NOTES: https://stackingbenjamins.com/renting-vs-buying-forever-1677 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

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

#603: Bethany's partner wants to invest most of their money in gold and silver, but no one seems to talk about this kind of investing. Is this a red flag or a potential opportunity?  Diana is worried she's been saving too much for her kids' college - hundreds of dollars a month since they were born. How does she know when to stop?   Wendy's pension and social security will cover all her basic expenses during retirement. Does the four percent rule still apply to her discretionary nest egg, or is there another approach? Former financial planner Joe Saul-Sehy and I tackle these questions in today's episode. Enjoy! P.S. Got a question? Leave it here. For more information, visit the show notes at https://affordanything.com/episode603 Learn more about your ad choices. Visit podcastchoices.com/adchoices

What do zipper injuries, holiday party mishaps, and servant leadership have in common? They're all part of today's wide-ranging look at careers—what to do, what not to do, and how to make your next move smarter (and safer). Joe Saul-Sehy, OG, and Neighbor Doug are joined by contributors Sandy Smith, Jesse Cramer, and a few classic career stories from the SB vault. Together, they explore: The surprising power of likability in the workplace How consistency and personal branding can open big doors Why some leadership styles flop and others inspire The real-life career missteps that made us all a little wiser A closer look at the Elevate Conference, which champions financial literacy for Black women And of course, it wouldn't be a basement episode without a trivia challenge. This time, Doug delivers a stat that'll make every listener squirm—let's just say it involves zippers and emergency rooms. Whether you're climbing the corporate ladder, considering a leap, or just trying to avoid HR's bad side, this episode packs in real advice and memorable stories from people who've been there, done that, and got the awkward email to prove it. Smart moves, cautionary tales, and Doug's very specific warning about pants—this one's got it all. FULL SHOW NOTES: https://www.stackingbenjamins.com/improve-your-career-trajectory-1674/ 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

#601: Nick and his wife have $100,000 to invest, but they're worried about the volatility of the current stock market. Should they look into alternative investments such as private equity? Even though Roth IRAs come with tax-free withdrawals in retirement, Josh is worried about his tax bracket going up and neutralizing the benefits. Is he right to be concerned? The retirement portion of Cindy's financial three-legged stool is set, and she's now focused on her taxable brokerage. What investment strategy will allow her to be work optional in 10 years? Former financial planner Joe Saul-Sehy and I tackle these questions in today's episode. Enjoy! P.S. Got a Question? Leave it at https://affordanything.com/voicemail Learn more about your ad choices. Visit podcastchoices.com/adchoices