Did 2024 Just Rewrite The Rules Of Investing? (SB1618) The Stacking Benjamins Show podcast

26:44

Tariffs got you sweating? We’ve got the strategy (and the LaCroix) to help you chill. Markets are wobbling, headlines are screaming, and you’re wondering if your portfolio is about to implode. Take a deep breath—and head down to the basement. In this episode, Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle the turbulence triggered by recent tariff changes. While others panic, we’re pouring the coffee and walking you through how to think smarter (and sleep better) during uncertain times. 🔍 Inside the episode: What recent tariff changes actually mean for your money How to protect your investments when markets get shaky Why doing nothing might be the smartest move The behavioral traps investors fall into—and how to avoid them Reassurance, real talk, and your weekly dose of Doug Whether you’re tempted to sell it all or just want a little peace of mind, this episode gives you tools to stay cool, stay invested, and stay the course. Because in the basement, we don’t panic—we plan. Learn more about your ad choices. Visit podcastchoices.com/adchoices…

The Stacking Benjamins Show

1
From Basement Beginnings to Million-Dollar Dreams (with Rudy Mawer) SB1666 1:18:43

hace 2 días1:18:43

1:18:43

Entrepreneurship, financial anxiety, and a guinea pig (yes, really). When you’ve got a stuffed guinea pig on your desk and a mic in front of you, it’s only a matter of time before you talk about that one time you ate guinea pig in Peru. (Spoiler: It was pretty good.) That’s how we open today’s show—but from there, things get real. Today’s main event features Rudy Mawer , founder of 60 Day Hustle , who joins Joe Saul-Sehy to share his incredible story. Rudy grew up in a modest home in England, raised by two world-class triathletes who pushed him to pursue excellence. He didn’t come from wealth—but he did build it, and fast. Rudy opens up about: His path from sports scientist to serial entrepreneur The role mentorship and strategic networking played in his success Why legacy matters just as much as hustle His latest documentary project and what drives him today Then, we turn to a conversation sparked by actor Seth Rogen’s recent interview with Dax Shepard. Rogen confessed he’s spent years saving out of fear—and maybe missed out on life in the process. So we ask: Are you hoarding cash out of anxiety? What happens when your savings plan becomes a cage? And how can Stackers find balance between security and spontaneity? Finally, we wrap up with one heck of a weather report. Mom’s neighbor Doug recounts the epic ice storm that left him snowed in, powered down, and questioning all his life choices. (Okay, maybe not all of them—but definitely his chainsaw strategy.) As always, Doug brings the trivia heat (and a little airline history), and we share some listener reflections that tie it all together. It’s a jam-packed episode—from financial fear to frozen driveways—with a little Peruvian culinary adventure tossed in. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-get-moving-on-your-money-goals-rudy-mawer-1666 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…

The Stacking Benjamins Show

1
BIG Questions In Finance: Are You IN or OUT? (SB1665) 1:08:33

hace 5 días1:08:33

1:08:33

Is good debt a myth? Should we all chase FIRE? The basement panel weighs in. In today’s Financial Concepts Friday roundtable, Joe brings the basement crew together for a lively “In or Out” debate on some of the most polarizing personal finance topics out there. Are we in or out on the idea of “good debt”? Do budgets really matter when you’re just starting out? Should you talk about money with your friends and family… or is that still taboo? Joining Joe are three financial thinkers who aren’t afraid to stir the pot: Paula Pant from Afford Anything Jesse Cramer from The Personal Finance for Long Term Investors Show OG from our own basement think tank (and planning headquarters) Together, they dig into: Whether any debt can actually be considered good If living without a budget is a fast track to financial regret—or freedom The upside (and awkwardness) of open money conversations How FIRE goals like retiring by 35 sound… and feel, once you really unpack them Plus, Mom’s neighbor Doug drops by with a trivia challenge that’ll have you laughing (and maybe yelling at your speaker). And of course, we wrap up with reflections that’ll leave you both entertained and a little bit wiser. So grab a LaCroix from the mini fridge and join us in the basement—this one’s packed with laughs, insights, and hot takes on cold, hard cash. FULL SHOW NOTES: https://stackingbenjamins.com/personal-finance-most-controversial-questions-1665 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…

The Stacking Benjamins Show

1
Top 5 Eye-Roll Financial Tips You Should Ignore SB1664 1:14:08

hace 7 días1:14:08

1:14:08

Ever been told to buy the biggest house you can afford... to “motivate yourself”? Or to skip insurance because “nothing bad will happen”? Yeah— us too. And we’ve got some thoughts. In this episode, Joe, OG, and Doug break down the Top 5 Worst Financial Tips they’ve ever heard—and more importantly, why taking them seriously could leave your finances in a flaming dumpster behind your dreams. From personal debt confessions to debates about extreme couponing, bad budgeting ideas, and the wild world of TikTok money myths, this episode is your roadmap to not falling for advice that sounds smart but… absolutely isn’t. In this episode: Why “buying big” won’t necessarily inspire you—it might just bankrupt you Skipping insurance to save money? We’ll show you how that plan ends Should couples really share just one checkbook? We investigate The great emergency fund vs. credit card debate When DIY everything turns into Why Did I Try? How the satire in The Joneses movie is secretly more real than you think Listener Q&A: Impact investing, private debt financing , and what it means to be an accredited investor Plus, a surprise TikTok moment, OG's thoughts on calendars, Doug’s history of April Fools’ disasters, and much more You’ll laugh, you’ll learn, and by the end, you’ll be a whole lot more confident dodging bad advice in the wild. 🎧 Tune in and stack smarter by skipping the “advice” that could sink your stack. FULL SHOW NOTES: https://stackingbenjamins.com/our-top-five-money-saving-solutions-1664 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…

The Stacking Benjamins Show

1
Tiffany Aliche on Connections and Financial Wholeness (with a side discussion on recent DoorDash/Klarna news) SB1663 1:13:57

hace 9 días1:13:57

1:13:57

Is financial literacy missing from your life like that sock you swear went in the dryer? Tiffany Aliche, AKA The Budgetnista, is here to help you find it—minus the lint. She shares her journey to financial wholeness and takes us behind the scenes of her brand-new PBS special. Meanwhile, Joe and OG break down why financial education starts with community (not overpriced guru courses), why ‘Buy Now, Pay Later’ is the financial equivalent of eating fast food in your car—feels great now, but you’ll regret it later—and how even a trip to Texarkana can teach you a thing or two about money. Plus, a story involving World War II espionage that somehow made its way into the mix. Here’s what’s on tap this week: Kicking off Monday with a solid dose of grumpiness (and a passionate store-brand rant). Hanging with The Budgetnista—Tiffany Aliche takes us behind the scenes. Why financial literacy isn’t just about numbers—it’s about community. The sneaky financial traps that might be eating your wallet alive. Tiffany’s PBS special—how she tackled stage fright and delivered a knockout show. Headlines that made us go “Wait, WHAT?!”—including Klarna and DoorDash teaming up. ‘Buy Now, Pay Later’—why it’s like borrowing money from Future You (and Future You is not happy about it). Mortgage strategies, financial independence, and the art of dodging debt. Could you survive a week on cash only? One of us is trying (and maybe crying). Food waste: it’s not just bad for the planet—it’s silently draining your bank account. Upcoming meetups, tax tips, and basement-style money wisdom you can actually use. And if you stick around long enough, well… who knows what else might show up? FULL SHOW NOTES: https://stackingbenjamins.com/budgetnista-financial-literacy-1663 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…

The Stacking Benjamins Show

1
Better Investing Using Horrible Investment Products (SB1662) 1:04:54

hace 12 días1:04:54

1:04:54

Ever fallen for an investment that seemed like a sure thing... until it wasn’t? You’re not alone. Today, we shine a light on some of the worst investment advice out there —and help you steer clear of it. Joining Joe at the roundtable are: Paula Pant from Afford Anything Jesse Cramer from Personal Finance for Long-Term Investors And Don McDonald , financial pro and former astronaut (not really, but just go with it) from Talking Real Money . Infinite banking and other shiny traps – What sounds like genius often comes with fine print you’ll wish you’d read. Penny stocks and the illusion of easy money – Spoiler: if it feels like a shortcut, it's probably a detour. Equity-indexed annuities and their slick sales tactics – When someone tells you there’s “no downside,” maybe run. Gut feelings vs. data – The panel weighs in on trusting instincts vs. trusting actual math. Teachers and 403(b) plans – A quick peek behind the curtain at one of the most overlooked problem areas in personal finance. How not to invest – A rundown of red flags and hard-won wisdom from people who’ve seen the worst up close. Meanwhile, Doug brings the trivia thunder with a question about sitcom salaries —and things quickly go from Big Bang to big bucks. Whether you’ve made a misstep or are just trying to avoid one, this episode will help you tune out the noise, spot the nonsense, and build a smarter, more resilient investment plan. FULL SHOW NOTES: https://stackingbenjamins.com/our-least-favorite-investments-1662 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…

The Stacking Benjamins Show

1
How NOT To Invest: Lessons from Barry Ritholtz SB1661 1:18:29

hace 14 días1:18:29

1:18:29

Ever wondered how the top financial minds avoid disaster while the rest of us are busy panic-Googling “best investments 2024”? Today, Joe welcomes Barry Ritholtz of Ritholtz Wealth Management down to Mom’s basement for a conversation that flips typical investment advice on its head. It’s not about what to do—it’s about what not to do if you want to grow your money without losing your sanity. Barry shares battle-tested insights from his years in the trenches, covering everything from behavioral finance to market psychology and how to avoid falling for trends that make great headlines but terrible portfolios. Also in this episode: Subscription hacks you didn’t know you needed (and yes, even that one you've been ignoring since 2021). How market history can be your secret weapon—if you actually pay attention to it. Tech innovations in finance and why Barry says they're both exciting and a little terrifying. Productivity gains, AI, and whether the future is a robot that trades ETFs for you while you nap. A peek into Barry’s latest book and the big idea that might shift how you think about investing. Doug creates yet another national holiday—because what the world needs now is Bow Chicka Wow Wow Day . Stacker mailbag time! We’re diving into job loss strategies, building bulletproof emergency funds, and yes, getting into the weeds with buffer ETFs. The never-ending showdown: remote work vs. office life—where do Stackers land? And of course, Doug’s trivia will challenge your financial knowledge and possibly your respect for faux holidays. Whether you’re a seasoned investor or just now figuring out what a 401(k) actually does, this episode brings the insight, laughs, and community you’ve come to expect from the basement. 🎧 Tune in and stack smarter—with fewer missteps and a whole lot more fun. FULL SHOW NOTES: https://stackingbenjamins.com/getting-your-investments-right-with-barry-ritholtz-1661 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…

The Stacking Benjamins Show

1
10 Ways to Stop Blowing Up Your Investment Portfolio (SB1660) 1:07:12

hace 16 días1:07:12

1:07:12

What do weddings, wineries, and Whoppers have to do with smart investing? This week, Joe, OG, and Doug kick off the episode with stories from the road—including a surprise credit card confession that somehow involves a Burger King (because of course it does). But then the gang shifts gears and dives into real money talk, breaking down investing wisdom from the legendary Barry Ritholtz. From navigating market cycles to keeping your emotions in check, Barry’s top 10 tips serve up the kind of grounded, no-BS advice your portfolio will thank you for—especially the next time the market gets jumpy or the headlines go haywire. They also tackle what politics really mean for your investments (spoiler: maybe less than you think) and why getting your expectations right could be the most important investment decision you make. Stick around to hear a listener question that hits close to home: How should you invest for an 84-year-old mom? It’s a multigenerational money moment that brings the discussion full circle. Here’s what you’ll learn: Why market cycles matter (and how to avoid getting whiplash) The hidden dangers of investing with your heart instead of your head What Barry Ritholtz says about predicting political impacts on your portfolio How to set realistic return expectations (and why that’s surprisingly freeing) A practical investing strategy for elderly parents—without the jargon Plus: Doug’s trivia takes a nostalgic turn into the wild world of Beanie Babies FULL SHOW NOTES: https://stackingbenjamins.com/how-not-to-invest-1660 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…

The Stacking Benjamins Show

1
How Pros Build Motivation Into an Effective Financial Plan (SB1659) 1:04:39

hace 19 días1:04:39

1:04:39

Ever wonder why some people crush their financial goals while others keep hitting snooze? Today, we’re talking about the secret sauce behind sticking to a financial plan—and no, it’s not just “wanting it more” (though that helps). Joining Joe in the basement is OG, alongside personal finance expert Jesse Kramer from The Best Interest and CFP Dana Anspach from Sensible Money . Together, they’ll break down why staying financially motivated is harder than it looks—and how to actually keep yourself on track, even when life (or a killer sale on Amazon) tries to derail you. We’ll explore why people resist financial planning (hint: it’s not always laziness), how goal-setting psychology plays into money habits, and why tracking your finances can be as powerful as tracking your fitness. Dana shares the surprising link between logging your retirement balance and saving more, while OG and Jesse tackle the age-old debate: should financial advisors be more like sports agents—pushing, coaching, and sometimes delivering the tough love? Plus, we dig into why writing things down actually works (seriously, it’s science) and how a simple mindset shift can help you finally take action. And of course, what’s a Friday without Doug’s trivia? This week, Doug takes us back to the boxing ring with a question about the legendary Joe Louis—and the sucker punch that is junk fees . ? Our roundtable throws their best guesses into the ring, but who will come out on top? Play along and see if you can take home the trivia belt! This was a great finish to a week of talking motivation and drive! From the seven steps to dynamic drive to sports agent Molly Fletcher on Wednesday and this discussion, it's a well-rounded week that should help you get up and go...even if you think YOUR get up and go got up and went. FULL SHOW NOTES: https://stackingbenjamins.com/motivation-habits-and-planning-1659 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…

The Stacking Benjamins Show

1
Climb Out of Your Rut: Molly Fletcher on Creating Sustainable Motivation (SB1658) 1:21:59

hace 21 días1:21:59

1:21:59

Ever feel like you're stuck in a rut , spinning your wheels, or just running low on motivation? Today, we crack the code on sustaining drive and avoiding complacency with former sports agent Molly Fletcher , who’s worked with some of the biggest names in sports and has been dubbed the female Jerry Maguire . She breaks down the fine line between contentment and coasting , plus shares keys to staying at the top of your game —from managing energy to embracing adversity like a pro . But wait, there’s more! Len Penzo (yes, of LenPenzo dot com fame!) joins us as guest co-host, bringing his usual mix of wisdom, dry wit, and probably a few thoughts on sandwich prices. And if you think motivation is tough, try navigating the world of credit —because while ambition is great, bad credit can still trip you up . From student loan pitfalls to practical credit repair tips , we cover what younger folks (and honestly, all of us) need to know about keeping those numbers in check. In this episode: Molly Fletcher on Peak Performance – Lessons from a top sports agent on how to stay motivated without burning out. Complacency vs. Contentment – Are you stuck or simply satisfied? Molly breaks it down. Managing Energy Like a Pro – Tom Izzo swears by it, and so should you. Credit Crash Course – What happens when student loans go delinquent , and how to fix the damage. The Living Without Credit Debate – Is a debt-free life possible, or just a financial myth? Doug & OG’s Ski Slope Disaster – A story of poor decisions, gravity, and bruised egos (hilarious in retrospect ). Len Penzo's Tips for Improving Credit Scores – Because nobody budgets quite like Len. Whether you need a motivation boost , a credit check-up , or just a good laugh at Doug’s expense , this episode has you covered. 🎧 Tune in for wisdom, financial hacks, and some après-ski storytelling you won’t want to miss! FULL SHOW NOTES: https://www.stackingbenjamins.com/find-your-dynamic-drive-molly-fletcher-1658/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices…

The Stacking Benjamins Show

1
How to Use Process to Create Sustainable Drive (SB1657) 1:07:44

hace 23 días1:07:44

1:07:44

Ever start a new financial goal feeling unstoppable , only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter . Today, Joe and OG take a deep dive into Dynamic Drive , the key to keeping your financial momentum going without burnout . We’ll break down the seven essential pillars —mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re ready to hit the ground running when we welcome former sports agent Molly Fletcher on Wednesday. 💰 In this episode: Why motivation fizzles out —and how to make it last The seven keys to Dynamic Drive (and how to apply them to your finances) How milestones and energy management keep you on track Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins? What cowboy fencing teaches us about peak performance (yes, that’s a thing) Plus, Doug serves up a sports trivia challenge —because what’s financial motivation without a little fun? 👉 Listen in now and get fired up—without burning out! FULL SHOW NOTES: https://stackingbenjamins.com/how-to-create-a-sustainable-drive-1657 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…

The Stacking Benjamins Show

1
Yeah, We Overpaid for That (SB1656) 57:43

hace 26 días57:43

57:43

Ever feel guilty about that $7 airport coffee or the mystery fees that somehow turn your $15 DoorDash order into a $40 financial regret? You’re not alone. This episode, Joe Saul-Sehy is joined by Paula Pant (Afford Anything) and Justin Peters (The Struggle Is Real) to unravel the sneaky ways convenience drains our wallets. In this episode: Airport Food: The Ultimate Financial Heist – Why does a sad turkey sandwich cost more than a steak dinner? We investigate. Concert Tickets & Junk Fees – You found $50 tickets… but somehow the total is now $127? Yep, we’ve been there. The True Cost of Convenience – From Uber Eats to express shipping, when is paying extra worth it—and when are we just being lazy? Trivia Time: Pie Day Special! – Who knew McDonald's pie sales could spark heated debate? Well, now we all do. Wedding Costs Gone Wild – Creative ways to cut costs without making your guests eat ramen. The Ben Franklin Effect & Social Hacks – Want better connections without breaking the bank? Turns out, old Ben had some wisdom on that, too. All this, plus some hilarious personal finance confessions that will make you feel better about your last impulse buy. 🎧 Tune in, laugh, and learn how to keep more of your Benjamins! FULL SHOW NOTES: https://stackingbenjamins.com/places-we-know-were-overpaying-1656 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…

The Stacking Benjamins Show

1
The Best Tax Prep Software of 2025 (SB1655) 1:10:05

hace 28 días1:10:05

1:10:05

Choosing the Best Tax Software for Your Needs Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution. Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year. H&R Block’s virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to. Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions. Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table. Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix. Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations. If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence. 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…

The Stacking Benjamins Show

1
Dream Big, Live Free: Grant Sabatier's Guide to Entrepreneurship (SB1654) 1:20:02

hace 30 días1:20:02

1:20:02

Ever wondered if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, he’s diving into the realities of entrepreneurship —from smart strategies to potential pitfalls. Where to start if you’re considering entrepreneurship – Not every side hustle is a winner, so how do you know if this path is right for you? The power of systems and constraints – Why guardrails and structure matter more than unlimited freedom. Pricing strategies and finding customers – Because even the best ideas need paying customers. Entrepreneurial misconceptions – Spoiler: It’s not all Ferraris and private jets. Can your wedding be a tax deduction? – We explore the entertaining but highly questionable ways some people try to make this work. Meanwhile, Doug serves up trivia on the highest-grossing console game ever (bet you won’t guess it). And if you stick around long enough, let’s just say there may or may not be a discussion about a comedy movie that turns financial struggles into pure entertainment. But, you know… no promises. If you’ve been toying with the idea of starting your own thing , this episode is packed with insights, real talk, and a few surprises along the way. FULL SHOW NOTES: https://stackingbenjamins.com/unlock-your-inner-entrepreneur-with-grant-sabatier-1654 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…

The Stacking Benjamins Show

1
The Surprising Benefits of Financial Inaction (SB1653) 1:11:46

hace 5 weeks1:11:46