The Stacking Benjamins Show

• Jonathan Clements: Why Simple Beats Complicated Every Time (SB1760)

  Here's what nobody tells you about building wealth: it's not about finding the perfect investment or timing the market. It's about doing boring things consistently until they're not boring anymore—they're just your life. In this Greatest Hits episode, Joe Saul-Sehy and OG revisit a 2023 conversation with Jonathan Clements, the beloved former Wall Street Journal personal finance columnist and founder of Humble Dollar who passed away recently. We're resharing this episode to honor Jonathan's legacy, his gift for making complex ideas simple, and the joy he brought to every conversation about money. Jonathan's book, My Money Journey, features 30 real stories from real people who built financial freedom—and the lessons are surprisingly simple (which doesn't mean easy). In this conversation, Jonathan breaks down what separated the people who made it from the people who kept spinning their wheels: steady habits, ruthless simplicity, and the kind of resilience that lets you keep going when life throws curveballs. From emergency funds that actually saved people to the rent vs. buy debate that reveals more about your priorities than your budget, this conversation cuts through the complexity to show you what actually matters. Jonathan's wisdom feels even more valuable now—a reminder that the best financial advice isn't about chasing trends, it's about building a life that works for you. Joe and OG also tackle listener questions, including whether to relocate for a better job and how to balance saving for tomorrow without sacrificing today. Plus: Doug's trivia, a Key & Peele-inspired TikTok minute, and proof that the best financial teachers leave lessons that last long after they're gone. What You'll Walk Away With: • The money habits that showed up in almost every success story from Jonathan's book (spoiler: none of them are sexy) • Why simplicity beats complexity in investing—and how to stop overcomplicating your portfolio • The rent vs. buy question reframed: it's not just about math, it's about what kind of life you want • How to balance aggressive investing with the safety net you actually need (not the one Instagram tells you to have) • Why emergency funds and health insurance are the unsexy heroes of every financial success story • What "margin for error" really means—and why it's the difference between surviving setbacks and being destroyed by them This Episode Is For You If: • You're tired of chasing the next "hot" investment strategy and want to know what actually works • You feel like everyone else has figured out money except you (spoiler: they haven't) • You want to hear real stories from real people, not just theory from talking heads • You're trying to balance living well now with saving for later—and feeling stuck in the middle • You believe the best teachers are the ones whose lessons outlive them 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

  --------  

  1:23:29

  --------

  1:23:29
• What a 12-Hour Walk Teaches You About Money (And Life) SB1759

  Here's a wild idea: What if the thing holding you back isn't your bank account, your age, or your circumstances—it's just the story you've been telling yourself? Joe Saul-Sehy and OG sit down with Colin O'Brady, four-time world record holder and endurance athlete who's done things most people would call impossible: solo trek across Antarctica, row across the Drake Passage, and yes, take a 12-hour walk that changed his entire perspective on what humans are capable of. Colin's not just here to tell adventure stories (though those are incredible). He's here to talk about the mental game—the part where you convince yourself to take the first step even when the finish line seems impossibly far away. Sound familiar? Whether you're staring down a cross-country expedition or trying to figure out if you'll have enough saved for retirement, the challenge is the same: push past the voice that says "I can't" and prove to yourself that you can. Then Joe and OG bring it back to the basement with a listener question about Roth vs. Traditional 401(k) contributions—because financial endurance is just as important as physical stamina. They break down how to think long-term about taxes, flexibility, and building a retirement plan that actually fits your life. Plus: Neighbor Doug delivers trivia that proves even world record holders have to earn their laughs in the basement. What You'll Walk Away With: • What Colin O'Brady's 12-Hour Walk reveals about breaking through your mental limits (and how it applies to money decisions too) • The mindset shift that separates people who attempt big goals from people who actually achieve them • Smart strategies for balancing Roth and Traditional 401(k) contributions based on your timeline and tax situation • Why flexibility matters as much as discipline—whether you're planning an expedition or planning retirement • Permission to set goals that scare you a little (because that's usually where the good stuff happens) This Episode Is For You If: • You've been telling yourself you "can't" do something but wonder if that's actually true • You want inspiration that comes with actual tactics (not just motivational fluff) • You're trying to figure out the Roth vs. Traditional 401(k) question and want a clear answer • You believe your best life is out there, but you're not sure how to build toward it • You need a reminder that big transformations start with small, intentional steps FULL SHOW NOTES: https://stackingbenjamins.com/conquer-your-mount-everest-greatest-hits-week-1759 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

  --------  

  59:53

  --------

  59:53
• What Retirees Wish They'd Known 10 Years Ago (SB1758)

  Want to know what keeps retirees up at night? It's not what they did—it's what they wish they'd done ten years earlier. Joe Saul-Sehy is joined by Jill Siriani (Frugal Friends), Jesse Cramer (The Best Interest), and Doc G (Earn & Invest), who all pull up chairs in the basement for a powerhouse roundtable on the five regrets that show up again and again when people hit retirement. These aren't hypothetical "what-ifs"—they're real stories from a real CFP, sharing tales about people who wished someone had told them sooner. From botched investment allocations that left people either too risky or too conservative, to tax mistakes that cost tens of thousands, to the heartbreaking pattern of people who saved everything but never actually enjoyed their money—this conversation gets real about what actually matters when you're trying to retire with confidence (and joy). The good news? Every single one of these regrets is avoidable. The panelists share what to do now so you don't become one of these stories later, including the estate planning moves that take ten minutes but save your family years of headaches, and why the biggest retirement regret isn't financial at all—it's emotional. Plus: Doug's trivia challenge pits the panel against each other for bragging rights, because even serious money talk deserves a little competition. What You'll Walk Away With: • The five regrets that show up over and over in retirement—and the specific moves that prevent each one • Why your investment allocation in your 40s and 50s might be setting you up for regret in your 60s • Tax strategies that keep more money in your pocket (because giving Uncle Sam extra is nobody's retirement dream) • The simple estate planning steps most people skip—and why your family will thank you for not skipping them • How to give yourself permission to actually enjoy your money instead of hoarding it out of fear This Episode Is For You If: • You're decades from retirement but want to avoid the "I wish I'd known" moments • You're closer to retirement and worried you've missed something important • You want to hear top financial minds debate what actually matters (spoiler: they don't always agree) • You're tired of generic retirement advice and want to hear what real retirees actually regret • You believe retirement should be about living well, not just having enough FULL SHOW NOTES: https://stackingbenjamins.com/top-5-retirement-plan-regrets-1758 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

  --------  

  1:10:58

  --------

  1:10:58
• Financial Literacy for Kids + Are Annuities Actually Safe? SB1757

  Here's a question: If everyone's buying annuities right now, does that mean you should too? Joe Saul-Sehy, OG, and Neighbor Doug tackle that exact question in this week's episode—but first, they're starting with the basics. Because before you can figure out complex financial products, you need to nail the fundamentals. And who better to teach them than Karen Holland, founder of Gifting Sense, who's made it her mission to help kids (and their parents) understand money in ways that actually stick. Karen breaks down how to teach the next generation about "need vs. want," why middle schoolers need to understand the real cost of "cool," and how financial literacy can be empowering instead of intimidating. Whether you've got kids or just want a refresher on the money basics you wish someone had taught you, this conversation is the reset button you didn't know you needed. Then things get timely: annuity sales are booming, and everyone's suddenly got an opinion. But are annuities the safe harbor they're marketed as, or just another way to lock up your money with fees you don't understand? Joe and OG cut through the sales pitch to help you figure out when annuities make sense—and when you're better off walking away. Plus: Doug delivers "life-changing" trivia (his words), there's an iHeart Music Festival giveaway tied to financial literacy, and you'll get your weekly dose of basement wisdom served with laughs. What You'll Walk Away With: • Karen Holland's framework for teaching kids financial literacy that actually changes behavior (not just lectures that go in one ear and out the other) • Why annuity sales are exploding right now—and the questions you MUST ask before signing anything • The difference between annuities that solve real problems and annuities that just create expensive ones • Financial habits that work at any age—whether you're teaching a 12-year-old or retraining yourself • How supporting financial education can score you iHeart Music Festival tickets (because doing good shouldn't be boring) This Episode Is For You If: • You want to teach kids about money but don't know where to start (or worry you'll mess it up) • Someone's pitched you an annuity and you're not sure if it's brilliant or a trap • You've heard annuities are "safe" but want to understand what you're actually giving up • You believe financial literacy is a gift worth giving—to your kids, your community, or yourself • You want money advice that doesn't talk down to you or assume you already know everything FULL SHOW NOTES: https://stackingbenjamins.com/raising-money-for-financial-literacy-1757 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

  --------  

  1:09:14

  --------

  1:09:14
• What to Do When Money Gets Tight SB1756

  Nobody plans for their finances to get tight. But here you are, staring at your bank account, wondering if you should panic now or wait until next Tuesday. Joe Saul-Sehy, OG, and Neighbor Doug are here to talk you off the ledge—and give you an actual plan for when money gets squeezed. Whether you're facing a layoff, dealing with reduced hours, bracing through a government shutdown, or just trying to make your paycheck last until payday, this episode is your financial storm shelter. The good news? You don't need to have everything figured out perfectly to make it through. You just need to know what to do first, what can wait, and how to keep your head (and your budget) together when everything feels uncertain. From building an emergency fund that actually works for your life to eating well on a ramen budget (spoiler: it's possible), this crew breaks down the practical moves that keep you afloat. Plus: Doug delivers trivia, the gang tackles the Voices for Good Charity Challenge (because even in tough times, small acts of giving matter), and they dissect a TikTok money tip that's... well, let's just say not all financial advice should be followed. What You'll Walk Away With: • The first three moves to make when money gets tight—before the panic spiral starts • How much emergency fund you actually need (hint: it's probably less than you think to get started) • Budget-friendly tactics for groceries, utilities, and keeping yourself fed without living on instant noodles • What to do about insurance and loans when cash flow slows down (and which mistakes cost you later) • Why small acts of generosity matter even when you're struggling—and how they help you too • A reminder that financial storms are temporary, but the skills you build weathering them last forever This Episode Is For You If: • Money feels tighter than it used to and you're not sure what to do about it • You want to build a safety net but don't know where to start (or how much is "enough") • The economy feels shaky and you want to feel prepared instead of panicked • You're tired of generic advice like "just save more" and want actual tactics • You need a pep talk wrapped in practical wisdom—because optimism without a plan isn't helpful FULL SHOW NOTES: https://stackingbenjamins.com/the-importance-of-emergency-funds-1756 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

  --------  

  59:48

  --------

  59:48

Mais podcasts de Negócios

Podcasts em tendência em Negócios

Sobre The Stacking Benjamins Show