The Stacking Benjamins Show

Is the constant push to be great quietly making life (and money) harder than it needs to be? This vault-worthy episode from 2023 hits differently, especially during a season when expectations run high and energy can run low. Joe Saul-Sehy is joined by Len Penzo, Paulette Perhach, Diania Merriam, and special guest Stephanie O'Connell Rodriguez for a candid roundtable about ambition, procrastination, perfectionism, and the surprising freedom that comes from choosing good over exhausting. Instead of chasing flawless systems or ideal outcomes, the conversation explores what actually moves the needle in real life. Building momentum. Removing friction. Letting go of the idea that every decision has to be optimized. Whether it's money habits, career goals, or simply getting unstuck, this episode offers a calmer, more sustainable way forward without lowering your standards or your future. Along the way, the group shares personal stories, practical strategies, and a few moments that only happen when smart people stop pretending they've got it all figured out. It's thoughtful, honest, and exactly the kind of perspective many Stackers didn't know they needed. What You'll Take Away from This Episode: • Why perfection often slows progress more than fear or lack of knowledge • How "good enough" can be a powerful financial strategy, not a compromise • Practical ways to break through procrastination without burning out • When delegation and automation actually help and when they just add complexity • How to balance ambition with contentment without feeling like you're settling • Why consistency beats intensity in both money and life Questions Worth Sitting With: Where are you chasing "perfect" when "done" would be better? What would improve immediately if you lowered the bar just a little? Which money habit could become easier if you stopped optimizing it? We'd love to hear your take. Share your thoughts in the Spotify comments or bring the conversation into the Basement Facebook group, especially if this episode gave you permission to ease up without giving up. Sometimes the best financial move isn't pushing harder. It's choosing progress that actually fits your life. This one's a quiet classic, and those tend to age the best. 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

One snowy Christmas Eve in Texarkana, Neighbor Doug settled into bed in his snazzy Superman Footie PJs (Amazon affiliate link), still buzzing on Joe’s Mom’s eggnog… Today’s special holiday episode recounts a completely original tale of Doug and the money lessons learned when he’s visited by three ghosts—past, present, and future. Especially when it comes to past credit mistakes, what’s done is done. Whatever method works best for you (debt snowball or debt avalanche), do that one. Come to terms with your bad money habits and realize that you can’t outearn them. It’s on you to fix the bad money habits of your past. Focus on what’s current and fix what needs fixing today. Don’t get caught in the trap of lamenting your past nor only planning for the future. Our only truly limited resource is time. Balance living for today with planning for the future. Remain in the present – especially when spending time with your loved ones – while keeping a vision in mind for your longer-term future plans. Be intentional about your plans and actions today and timeline what you want to achieve in what time you have remaining. Communicate on a regular basis with your “team” (loved ones) about your financial goals, progress, and situation. We recommend scheduling a weekly Family Budget Meeting. Automate as many of your financial decisions as possible today so you never have to think about them again in the future. Commit to paying off that mortgage early, ramp up those retirement savings contributions, stack those Benjamins for your kids’ college savings. Decide where you want to be financially in the future; face reality of where you are currently (we like our sponsor, Monarch Money, to track where you are); and take the necessary step to make that future a near certainty. Remember that time is the one commodity that’s finite for all of us. Value your time and experiences while staying responsible to your present and future self. Remember and learn from the sins of your past to build on your strengths; focus on living in the present and building your financial foundation; and head into the future with more confidence than Joe’s Mom’s Neighbor Doug during the annual Sun’s Out, Guns Out El Camino Competition at the Sizzler. FULL SHOW NOTES: https://stackingbenjamins.com/doug-and-the-three-ghosts-2025-holiday-special-1778 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

It's the most wonderful time of the year in the basement, and we're kicking off the holiday season with our biggest, most packed episode yet. Joe Saul-Sehy, OG, and Neighbor Doug welcome Joel Larsgaard and Matt Altmix from the How to Money podcast for a year-end celebration of everything that mattered in money during 2025. Think of this as the holiday parade of personal finance episodes. There's a lot happening, it's all connected, and you'll want to stick around for the whole thing. First up, Joel and Matt join the crew for their Top 5 Lessons from the Events of 2025. From AI's real impact on everyday work to market surprises nobody saw coming, this segment unpacks the money moments that actually changed how we think about our finances. These aren't just headlines rehashed. They're the insights that'll help you make smarter moves in 2026. Then the show shifts to a fascinating trend everyone's noticing but nobody's quite figured out yet. Why is everyone suddenly betting on everything? Prediction markets are exploding, retail investors are taking bigger risks, and the line between investing and gambling feels blurrier than ever. Joe, OG, Joel, and Matt dig into what's driving this shift, whether it's brilliant or reckless, and how to think about risk when it seems like the whole world just discovered the casino. But wait, there's more. Nick from Alaska calls in with a real-world budgeting challenge that proves even the most prepared Stackers face seasonal money surprises. His situation sparks the kind of practical, helpful conversation this show does best. And because this is a holiday kickoff episode, we're wrapping with big news about the Stacking Benjamins Vault, the new tool designed to help you organize and protect your most important financial documents without the headache. This episode has everything. Big ideas, real questions, legendary guests, surprise calls, and the energy of a show that knows the best episodes are the ones where there's almost too much good stuff to fit in. Welcome to the holiday season, Stacker style. What You'll Walk Away With: • Joel and Matt's Top 5 Money Lessons from 2025 that actually matter going forward • How AI really affected work and income this year in practical, not theoretical, ways • Why prediction markets and betting culture are suddenly everywhere and what it means for investors • Whether the shift toward riskier investments is smart adaptation or dangerous groupthink • Nick from Alaska's budgeting challenge and the solutions the crew offers in real time • An inside look at the Stacking Benjamins Vault and how it helps you organize what matters most • The perfect energy boost heading into holiday episodes and a new year of smarter money moves This Episode Is For You If: • You want the year-end money recap that feels like a celebration, not a lecture • You've noticed everyone's suddenly betting on elections, sports, and markets and wonder what's going on • You love episodes with special guests, surprise calls, and enough happening to keep you engaged the whole way • You want to head into the holidays feeling smarter about money, not more anxious • You're ready to kick off the season with the Stacking Benjamins crew at their absolute best After You Listen, Share This: What was your biggest money lesson from 2025? And have you noticed yourself (or people you know) getting more comfortable with risky bets lately? Drop your thoughts in the Spotify comments or the Basement Facebook group because this episode kicks off our holiday run, and we want to hear what's on your mind heading into 2026. FULL SHOW NOTES: https://stackingbenjamins.com/year-end-lessons-with-the-runners-up-of-the-charity-challenge-1777 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Before you charge into a new year with fresh goals, shiny spreadsheets, and unrealistic optimism, it's worth doing the one thing most people skip. Looking back honestly at what just happened. Joe Saul-Sehy, OG, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) gather for an end-of-year roundtable to unpack the financial, personal, and behavioral lessons that 2025 handed us. Sometimes those lessons arrived gently. Sometimes they shoved us face-first into reality. Either way, this episode isn't about predictions for what's coming. It's about understanding the patterns from what already happened. The team digs into what diversification actually meant this year when some of the old rules stopped working the way they used to. They explore why emotional reactions to headlines still cost investors real money, even when everyone knows better. And they examine how policy noise (tariffs, political drama, market freakouts) reminded us once again that short-term chaos rarely deserves long-term decisions. Along the way, the conversation touches on housing lessons learned, family priorities that got re-examined, and AI's quiet but growing influence on work, productivity, and opportunity. The thread running through it all? Financial planning only works when it serves the life you're trying to build, not the other way around. This episode balances big-picture thinking with real-life reflection. It's the kind of honest look back that actually helps you move forward smarter instead of just louder. What You'll Walk Away With: • The most important financial lessons 2025 taught investors, whether they actually listened or not • How AI quietly changed work, productivity, and opportunity in ways that matter for your money decisions • Why diversification looked different this year and what investment principles still held up under pressure • How market volatility exposed emotional blind spots you might not have known you had (and how to fix them) • What the housing market taught us about patience, expectations, and timing • Why year-end reflection beats year-end predictions every single time • How family dynamics, personal values, and money planning intersect more than anyone likes to admit This Episode Is For You If: • You want to learn from 2025 before setting goals you'll abandon by February • You made some money decisions you're proud of and some you'd rather forget • Market headlines changed your behavior this year and you're wondering if that was smart • You're tired of prediction content and want actual reflection on what already happened • You believe getting smarter about money means being honest about what you got wrong Before You Hit Play, Think About This: What money decision in 2025 are you most proud of, and which one taught you the biggest lesson? Going into 2026, what one financial habit would make the biggest difference if you actually stuck with it? Bring those thoughts into the Facebook group or drop a comment because your reflections might help another Stacker avoid learning the same lesson the hard way. FULL SHOW NOTES: https://stackingbenjamins.com/top-money-lessons-of-2025-1776 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 "giving back" isn't about writing bigger checks but about using what you're already great at? Most people think philanthropy is reserved for people with their names on buildings. That assumption keeps them from realizing they already have something valuable to give. Joe Saul-Sehy, OG, and Neighbor Doug welcome John Studzinski, managing director at PIMCO and founder of the Genesis Foundation, for a conversation about generosity, purpose, and impact that actually applies to everyday Stackers. John challenges the whole concept of "philanthropy" as something for the ultra-wealthy and reframes giving as a muscle anyone can build using time, talent, and intention instead of just cash. The conversation reveals how you can create meaningful impact right now, regardless of your bank balance. Whether you're great at organizing, teaching, listening, or solving problems, those skills matter more than you think. John breaks down how to identify your personal talent for impact and why intentional giving beats reactive charity every single time. Then the show shifts to retirement planning, specifically how to design a glide path that works with your behavior instead of fighting it. Joe and OG break down how to manage risk as you age, why annuities keep showing up in retirement conversations, and why smart planning focuses less on chasing perfect returns and more on creating stability you can actually live with. Because the math might say one thing, but your ability to sleep at night matters just as much. Along the way, the crew takes a detour into ChatGPT's potential future, explores a few behavioral finance truths that hit uncomfortably close to home, and wraps with a pop culture review reminding us that money decisions never happen in a vacuum. This episode is about aligning your resources (financial and otherwise) with the life you actually want to live. What You'll Walk Away With: • Why "giving" is a better word than "philanthropy" and why that shift in language actually matters • How to identify your personal talent for impact even without significant wealth • Why generosity works best when it's intentional and strategic rather than reactive • How retirement glide paths actually work and why your behavior matters more than the math • The role annuities can play in reducing retirement anxiety without sacrificing everything • Why percentages can be misleading, real dollars tell better stories, and context is everything • How fear, FOMO, and age quietly shape your investment decisions in ways you might not notice • Permission to build a retirement plan around stability instead of maximum growth This Episode Is For You If: • You want to give back but think you need more money before you can make a real difference • You're approaching retirement and tired of advice that ignores how you actually feel about risk • You've wondered if annuities deserve their bad reputation or if there's something there • You want your money decisions to reflect your values, not just optimize for returns • You believe purpose and planning should work together, not compete Before You Hit Play, Think About This: What's a talent you already have that could create more impact than money alone? And when it comes to retirement investing, what decision do you know is emotional but still struggle with? Drop your answers in the comments because John's perspective on giving and the crew's take on retirement planning might shift how you think about both. Learn more about your ad choices. Visit podcastchoices.com/adchoices