The Stacking Benjamins Show

If Jen Drummond can climb K2, you can open that Roth IRA. That's the premise of this greatest hits episode featuring mountaineer and author Jen Drummond, who became the first woman to complete the Seven Second Summits. But here's why we're replaying this conversation from early 2024: it's not about mountaineering. It's about courage. Joe Saul-Sehy opens by explaining why courage matters for your money goals. It takes courage to look at your financial life honestly, to try something new like opening your first investment account, to admit you made a mistake and course correct. Courage builds confidence, which gives you the commitment to take another step. It works like a flywheel. One brave decision leads to another, which builds more confidence, which creates momentum. Jen's story illustrates this perfectly. After surviving a devastating 2018 car crash that first responders said should have killed her, and losing a friend shortly after, she made a decision to "die living." That mindset took her from someone who'd never slept in a tent to the top of some of the world's most dangerous peaks. But what makes Jen's approach so valuable isn't the extreme nature of her goals. It's her method. She didn't succeed through recklessness. She succeeded through preparation, safety protocols, building the right team, learning from others who'd gone before her, and breaking massive goals into clear milestones. Sound familiar? That's exactly how you build wealth. Throughout the conversation, Jen shares lessons that apply whether you're climbing Everest or just trying to max out your 401(k). How to push through "blue ice" (those moments when progress slows to a crawl and every move has to count). Why big goals require big teams (you can't do this alone). How to fire bad help when someone's dragging you down. Why getting to the summit is only halfway (you need enough energy to get home safely). The episode also includes practical career advice for navigating today's tougher job market, from refreshing your LinkedIn profile to the power of face to face networking, plus Doug's trivia about Andrew Jackson and the only day the U.S. was completely debt free. What You'll Learn: • Why courage is a skill you develop through reps, not something you're born with • How small brave decisions compound into bigger ones (the flywheel effect) • Why preparation and safety matter more than boldness in any big goal • How to break down overwhelming goals into clear, achievable milestones • Why looking back at progress matters as much as looking ahead • The importance of learning from others who've achieved what you're attempting • How to build the right team around your goals and fire people who hold you back • Why getting to your goal is only halfway (you need sustainability, not just achievement) • Practical strategies for strengthening your career in a competitive job market • How Jen's "blue ice" moments teach us to slow down and be deliberate during tough stretches This Episode Is For You If: • You're intimidated by financial goals that feel too big or complicated • You keep putting off important money moves because you're scared of making mistakes • You need permission to start small and build momentum over time • You're looking for a framework that works for any goal (financial or otherwise) • You believe courage is something you can develop, not just inherit This is a greatest hits episode because Jen's message about building courage through action is exactly what you need heading into a new year. If she can climb the second highest peak on every continent, you can absolutely handle that 401(k), that budget, that first investment account. Question for You: What's one small brave money move you could make this week? Opening an account? Checking your credit score? Having that awkward budget conversation? Drop it in the comments or The Basement Facebook group because sometimes the first step isn't dramatic, it's just intentional. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Live from Joe's mom's basement (where humility is encouraged and spreadsheets are optional), the crew tackles a deceptively simple question. If most people think they're above average with money, what advice actually helps someone who isn't? Joe Saul-Sehy, OG, Doug, Jesse Cramer, and guest Whitney Hanson (Money Nerds podcast) run a thought experiment inspired by Morgan Housel's observation that nearly everyone believes they're financially smarter than the median. What straightforward moves keep someone from needing last minute financial Hail Marys? The answer isn't flashy. It's systems. Whitney kicks things off with a practical starting point: identify your knowledge gaps. Tools like Investor.gov quizzes can reveal blind spots, and she suggests theming your learning (one focus per month) so financial literacy doesn't feel overwhelming. From there, the conversation turns to controllables: cash flow, savings rate, lifestyle inflation, and career capital. Because while markets bounce around, your habits are yours. The gang also introduces the idea of a tactile money leak audit, physically reviewing spending to spot waste that autopilot budgeting apps can miss. It's less glamorous than crypto speculation but far more effective. Investing gets reframed too. Instead of treating it like a mysterious Wall Street game, they suggest thinking of it as owning small pieces of companies you already know and use. Start small. Automate it. Build reps. Confidence follows action. Insurance and estate planning round out the episode. The crew urges listeners to shop multiple advisors, understand policy details before signing, use AI to help decode fine print without blindly trusting it, and avoid overconfidence just because something sounds right. Doug keeps things lively with trivia revealing that Johnny Carson's 1982 DUI fine was a very specific $603, and OG once again proves suspiciously good at guessing. What You'll Learn: Why most people overestimate their financial knowledge and what to do about it How to identify and close your personal money knowledge gaps The key financial variables you actually control How to perform a simple money leak audit Why small, automatic investing beats waiting for the perfect moment How to make investing feel familiar instead of intimidating The basics everyone should understand about insurance and estate planning Why repetition builds financial confidence faster than theory The Big Takeaway: You don't need advanced tactics. You need consistent systems. Focus on what you control. Automate the boring stuff. Learn one thing at a time. Build margin. Repeat. Because the goal isn't to be above average. It's to be steady enough that you never need a desperate Hail Mary. This Episode Is For You If: You feel like everyone else has money figured out except you Financial advice usually feels too complicated or assumes knowledge you don't have You're tired of feeling behind and want simple systems that work You want to build confidence through action, not just theory You believe steady progress beats trying to be perfect Question for You: What was the first simple money habit that changed your trajectory? Share it in the Spotify comments or The Basement Facebook group. Your small win might be exactly what another Stacker needs to hear. FULL SHOW NOTES: https://www.stackingbenjamins.com/bottom-50-money-tips-1809/ 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

Live from Joe's mom's basement (where the jokes are free but hospital care apparently isn't), the Stacking Benjamins crew tackles two very real financial stressors: surprise medical debt and a shifting housing market. First up is Imani Vance, who joined the Coast Guard at 19 and soon faced a nightmare scenario. What started as appendicitis escalated to severe sepsis after limited on-base resources and long waits for off-base care. After hospitalization, including treatment for an abscess and eventual appendix removal, Imani received a bill totaling roughly $43,000 to $45,000. And here's where it gets worse. She didn't qualify for VA help because she hadn't yet served 180 days. Accessing Coast Guard records proved difficult. The bill arrived after the care, opaque, overwhelming, and completely disconnected from what she had agreed to or expected. If you're a Stacker, you know this feeling. The stress isn't just the number. It's the lack of clarity. Imani shares how she started researching options, discovered the nonprofit Dollar For through Reddit, and used them to apply for hospital financial assistance. Dollar For helped her complete and submit the required forms, and within weeks, she was approved for 100% financial assistance, wiping out the bill entirely. Joe Saul-Sehy highlights an important takeaway. Nonprofit hospitals are legally required to offer financial assistance. Many for-profit hospitals offer programs, too. Income thresholds are often higher than people assume. The applications can be confusing, which is where advocates like Dollar For can make a huge difference. Instead of locking into $300 to $500 monthly payments for years, Imani walked away debt-free and with a completely different outlook. After Doug drops trivia about the youngest bank robber (yes, really), the crew pivots to housing. A recent Wall Street Journal/Redfin headline suggests the housing market may be tilting toward buyers, with more homes selling below list price and average sales around 8% under asking. Joe and OG break down what that means for Stackers, not in headline hype terms but practical life terms. What You'll Learn: Medical Bills and Financial Assistance: • Why medical debt feels different from other debt • How hospital financial assistance programs work • Why many people qualify but never apply • How nonprofits like Dollar For can help navigate the paperwork • Why you should always ask for itemized bills and assistance options Housing Market: Think Forward, Not Backward: • Why you shouldn't get stuck in your mortgage just because you locked in a low rate • How anchoring to past rates can cloud present decisions • Why negotiating power is shifting and how to use it • The importance of building financial margin when income rises • Smart, low cost staging tactics, including hiring a pro for just an hour of advice • How AI tools can help with pricing and presentation ideas The Big Takeaways: Before paying a massive medical bill, check whether you qualify for assistance. Financial stress often comes from confusion. Clarity is power. Housing decisions should be forward-looking, not emotionally anchored to the past. Margin and flexibility beat perfect timing. This Episode Is For You If: • You're facing medical debt and thought you had no options • You've been putting off dealing with a hospital bill because it feels hopeless • You're stuck in a low rate mortgage and wondering if you should move • You want to understand what's really happening in the housing market • You believe there's always more to the story than the bill or the headline Question for You: Have you ever negotiated or reduced a bill you initially thought was non-negotiable? Share your story in the Spotify comments or The Basement Facebook group. Your experience might help another Stacker avoid paying more than they should. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Live from Joe's mom's basement (complete with dog mugs, birthday roasting, and Doug polishing his trivia crown), the crew tackles a headline that caught plenty of attention. Suze Orman backing off her long held stance that everyone should work until age 70. Does that mean you shouldn't work longer? Not exactly. Joe Saul-Sehy, OG, Doug, and special guest Len Penzo break down the math behind working into your late 60s or beyond. More years to save, more compounding, fewer years drawing down assets. It's powerful stuff. But they also remind Stackers that work doesn't have to mean the same grind, and that retiring and claiming Social Security are two completely separate decisions. Len shares why he plans to delay Social Security until 70, walks through the break even math versus claiming at 62, and highlights the importance of survivor benefits for spouses. At the same time, the crew emphasizes that health, longevity expectations, and personal priorities can completely change the right answer. Suze's updated advice leans heavily on stress testing your retirement plan, and that's where the basement really digs in. What happens if inflation sticks around? If your side hustle disappears? If returns are lower than expected? The team argues that instead of chasing the perfect retirement date, you should solve for flexibility. Avoid analysis paralysis but don't skip the planning either. They also debate liquidity (hint: it doesn't mean stuffing your mattress with cash), share a cautionary tale about delayed IRA access, and remind listeners that logistics matter just as much as spreadsheets. In the TikTok Minute, a retiree reframes time as priceless instead of something to maximize. That sparks a thoughtful conversation about identity in retirement, the adjustment period after leaving work, and what makes life satisfying once the paycheck stops. Plus: A big community win as a fellow Stacker crosses the $1 million net worth milestone, stats on how common that really is, upcoming Stackers meetups, Doug's Gutenberg themed trivia, and unexpected retirement expenses involving squirrels and BarkBox. Because this is the basement, after all. What You'll Learn: • Why working longer can strengthen your retirement math and when it might not • The difference between retiring and claiming Social Security • How to think about Social Security timing, longevity, and survivor benefits • What it means to stress test your retirement plan • Why flexibility often beats perfect optimization • The real meaning of liquidity and why too much idle cash can hurt efficiency • How retirement success is often about time, not just money • Why identity shifts matter just as much as account balances The Big Takeaway: Retirement doesn't require working forever. But it does require a coordinated plan, one that brings together your assets, Social Security strategy, spending flexibility, and (most importantly) how you want to spend your time. Because in the end, money is renewable. Time isn't. This Episode Is For You If: • You've been told to work to 70 and aren't sure if that's right for you • You're trying to figure out when to claim Social Security • You want to stress test your retirement plan but don't know where to start • You're worried about the adjustment period after leaving work • You believe retirement planning is about more than just hitting a number Question for You: If you could retire tomorrow, what would you spend more time doing, and what would you happily leave behind? Share your thoughts in the Spotify comments or The Basement Facebook group. Your answer might inspire another Stacker who's quietly wondering the same thing. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Want your kids to grow into confident money decision-makers without turning every dinner conversation into a financial lecture? In this roundtable episode, Joe sits down with Livia (“Liv”) Roder, host of the Liv Lab Podcast, Karen Holland of GiftingSense.org, and John Lanza, host of the Art of Allowance Podcast to explore what actually helps kids understand money before the stakes get big. Instead of theory, this discussion focuses on real moments when money suddenly becomes real: college price tags, house-hunting sticker shock, allowances that run out too fast, and purchases that teach better lessons than any lecture ever could. The panel shares practical ways families can build financial confidence through everyday decisions, honest conversations, and a willingness to let kids learn by doing. What the Stacking Benjamins “Confident Explorer” will gain from this episode: How to talk about money naturally so kids see it as a life skill, not a stressful taboo topic Why modeling everyday behavior matters more than formal “money talks” A simple shift from “Can I have it?” to “Is it worth it?” that builds independent thinking How small spending mistakes become powerful teaching moments when handled without shame Ways to introduce big topics like college costs gradually so kids feel informed instead of overwhelmed Real-life money lessons that sparked the conversation: Livia’s moments when money suddenly felt real, from college forms to realizing savings aren’t just “bank numbers” Karen Holland’s memorable eighth-grade back-to-school budget experiment Early allowance experiences that helped connect choices with consequences Why kids absorb far more from overheard conversations and daily habits than parents expect Practical strategies parents can use right away: Starting with simple allowance systems or “jars” to visualize spending, saving, and giving Karen’s “Does It Make Sense?” pause to slow impulsive purchases Joe’s “circle back” technique, revisiting purchases later to reflect without criticism Letting kids fail safely so regret becomes learning instead of embarrassment Helping kids split costs or contribute toward purchases to create ownership Navigating tougher parenting questions: Should kids see financial stress, or should parents shield them? How to practice age-appropriate honesty without creating anxiety Why financial jargon like FAFSA or taxes can unintentionally intimidate teens Bringing kids into real financial conversations so they build confidence early Money challenges unique to today’s kids: Teaching spending awareness in a tap-to-pay, frictionless world Cash vs. cards vs. apps and how each changes behavior Building a “pause habit” before spending when transactions feel invisible If you could teach just one money skill… The panel compares their top priorities: Awareness of cash flow and where money actually goes Thinking before buying instead of reacting emotionally Paying yourself first and building saving habits early Plus, a little basement fun along the way: Favorite purchases that truly felt worth it (from snowboards to board games to a Kindle) Stories that prove money lessons stick best when tied to real experiences Resources and next steps from each guest, including tools, calculators, and upcoming episodes This episode reinforces a core Stacking Benjamins idea: kids don’t learn money through perfect decisions. They learn through guided experience, honest conversations, and the freedom to practice while the stakes are still small. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-teach-your-kids-about-money-1806 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

Live from Joe's mom's basement (where receipts go to be judged and spreadsheets fear OG), this episode tackles two big questions Stackers are asking right now. What's the best tax software for filing your 2025 return? And what should normal, long term investors make of gold, silver, and crypto taking a wild ride? Joe Saul-Sehy and OG are joined by Robert Farrington from The College Investor to break down the tax software landscape without the marketing fluff. Because if you're our Stacker avatar, you don't want hype. You want something that works, doesn't overcharge you, and doesn't suddenly upsell you because you clicked the wrong box. Then in the headline segment, the crew digs into the sharp pullback in precious metals and crypto. Is this the beginning of something bigger? A buying opportunity? Or just another reminder that chasing shiny objects (literally shiny in gold's case) can make your portfolio feel like a roller coaster? As always, Doug brings trivia, there's some basement banter, and the team separates smart strategy from financial fashion trends. Choosing the Right Tax Software (Without Overpaying): • Why FreeTaxUSA might be the best overall value for most Stackers • When TurboTax or H&R Block make sense and when you're just paying for bells and whistles • The pros and limitations of truly free options like Cash App Taxes and Chime • Why TaxSlayer can be a solid choice for student loan borrowers, landlords, and side hustlers • What investors and crypto traders need to know about brokerage imports and the new 1099-DA form • Why filing taxes is mostly data entry and where real tax planning can make a difference • Simple tools to track mileage, expenses, and side hustle income without losing your mind Bottom line: the best software isn't universal. It's the one that fits your situation without surprise fees. Gold, Silver, and Crypto: What the Drop Means: • Why assets without earnings (like gold and many cryptocurrencies) can swing wildly • The danger of investing based on FOMO instead of a plan • How concentration risk increases the range of possible outcomes, both good and bad • Why short term volatility doesn't automatically change a long term strategy • The risks of misinformation, including AI generated financial advice that isn't real OG walks through how disciplined investors think during volatile moments: zoom out, revisit your allocation, and stick to your strategy instead of reacting emotionally. The Big Takeaway: Whether you're picking tax software or deciding what to do during a market drop, the lesson is the same. Choose tools that fit your life. Build a plan before the chaos hits. Don't let headlines or shiny objects hijack your strategy. This Episode Is For You If: • You're trying to pick tax software without getting ripped off • Markets are making you nervous and you're not sure if you should do something • You want to understand what's happening with gold and crypto without the hype • You're looking for calm, practical guidance during a chaotic time • You believe steady wealth beats chasing shiny things Let's Hear From You: What tax software are you using this year and why? When markets get volatile, what helps you stay disciplined? Share your thoughts in the Spotify comments or The Basement Facebook group. Your experience might help another Stacker avoid an expensive mistake. FULL SHOW NOTES: https://stackingbenjamins.com/the-best-tax-software-2026-robert-farrington-1805 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

Think building seven figure wealth requires exotic investments or perfect timing? This President's Day episode from Joe's mom's basement tells a very different story. Joe Saul-Sehy, OG, and Neighbor Doug dig into a Kiplinger My First Million case study featuring a Wisconsin couple who started saving at age 32 with exactly zero invested and quietly built $2 million over the next 22 years using mostly retirement accounts and steady habits. Their success sparks a bigger conversation about why simple strategies often outperform complicated ones, and how surviving the boring middle is where wealth is created. Along the way, the gang tackles advisor fees, the psychology of enough, long term care decisions, and the real value financial professionals can bring. Of course, it wouldn't be a basement episode without trivia, community wins, and a few unexpected detours (including a conversation about giant toilet paper rolls that somehow reinforces the episode's central theme). What You'll Take Away: • Why ordinary retirement accounts (401(k)s, SEP IRAs, and Roth IRAs) can be enough to build significant wealth without chasing complex investments • How starting with just enough to earn the employer match creates momentum without overwhelming new savers • A simple escalation strategy: increasing contributions by 1% each year to grow savings almost painlessly • The often missed detail of contributing through the final paycheck to capture the full employer match • A creative gamification approach to Roth contributions tied to the Social Security wage base • How reframing long goals into months instead of years helps investors stay motivated during the long, quiet middle stretch • Why imperfect plans with higher fees can still beat waiting for the perfect investing setup • The real concerns people have about trusting workplace retirement plans and how those plans actually function • Lessons the featured couple learned, including the value of post tax flexibility later in life • Long term care planning as risk management, including balancing insurance coverage with self funding strategies Big Behavioral Conversations: • A TikTok minute featuring Dr. John Delony sparks a discussion about defining enough and whether chasing more success is driven by purpose or ego • How redefining success can shift financial decisions more than any spreadsheet ever will • The danger of constantly moving financial goalposts once progress begins Listener Mailbag: When Is a 1% Advisor Fee Worth It? OG walks through how to evaluate an advisor relationship beyond performance numbers, including whether your advisor helps you make money or avoid costly mistakes, the value of saved time and reduced stress, planning continuity for spouses or heirs, typical fee structures, and how to have an honest fee conversation without damaging a long standing relationship. This Episode Is For You If: • You're behind on saving and worried you've missed your window • You feel like wealth building requires strategies you don't understand • You want proof that simple plans work if you stick with them • You're wondering if your advisor's fee is worth it or if you should manage it yourself • You need reassurance that boring and consistent beats exciting and complicated This episode is a reminder that wealth rarely comes from brilliance or shortcuts. More often, it comes from steady decisions repeated consistently while everyone else searches for something more exciting. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-make-a-million-after-starting-late-1804 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

Nothing says romance like a heated debate about the 4% rule. Live from the basement (which suspiciously resembles YouTube headquarters), Joe Saul-Sehy, OG, Neighbor Doug, and the panel celebrate Valentine's Day weekend the only way Stackers know how: by putting their favorite financial ideas on the hot seat. This isn't a polite discussion. It's a rapid fire "love it or leave it" showdown where popular money strategies either get roses or get shown the door. On the chopping block: Paying off a low interest mortgage early: financial freedom or opportunity cost disaster? The FIRE movement: empowering clarity or accidental misery? Lifestyle inflation: natural evolution or silent wealth killer? Real estate as passive income: dream scenario or second job in disguise? The 4% rule: reliable rule of thumb or outdated security blanket? Budgeting apps: behavior changer or digital guilt machine? Expect strong opinions. Expect pushback. Expect OG to bring spreadsheets to a knife fight. Expect Doug to stir the pot. And expect at least one take that makes you argue out loud in your car. Along the way, the crew swaps Valentine's Day plans, reviews survey results from listeners, and throws down in a trivia challenge that could shake up the leaderboard. With margin call rules in play, nobody's position is safe. What You'll Discover: Which popular financial strategies hold up under scrutiny and which ones deserve a breakup Why smart people disagree about mortgage payoff strategies Whether the FIRE movement creates freedom or just different problems The truth about lifestyle inflation and when it's okay versus when it's dangerous Why real estate investing is rarely as passive as it sounds Whether the 4% rule still works or needs serious revision If budgeting apps actually help or just make you feel guilty How to question your own financial assumptions without second guessing everything This Episode Is For You If: You want to understand WHY you believe what you believe about money You're tired of one-size-fits-all financial advice You enjoy hearing smart people debate and disagree respectfully You've been following certain money rules without questioning if they fit YOUR life You believe the most loving thing you can do for your financial plan is challenge it This episode is for anyone who doesn't just want answers but wants to understand the thinking behind them. Because sometimes the most loving thing you can do for your financial plan is break up with strategies that aren't serving you anymore. FULL SHOW NOTES: https://www.stackingbenjamins.com/love-it-or-leave-it-valentines-day-edition-1803/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

What's more romantic than roses and chocolate? How about not fighting about money. Joe Saul-Sehy and OG welcome Douglas and Heather Boneparth, the financial planning power couple who literally wrote the book on navigating money in relationships. Broadcasting from the basement (where love is patient and spreadsheets are kind), the crew dives into how people can build financial trust, avoid money secrets, and actually enjoy talking about dollars without it turning into a heavyweight title fight. Whether you're navigating finances with a romantic partner, a roommate splitting rent, an accountability partner keeping you honest, or a family member you're in business with, these principles apply. Because let's face it: our Stacker avatar isn't trying to impress Wall Street. You're trying to build a great life with the people who matter, without money becoming the thing that creates tension. Douglas and Heather break down what healthy financial communication really looks like, how to spot and prevent financial secrecy, and why shared goals matter more than perfectly matched spending styles. They also tackle the tricky stuff: different money upbringings, emotional baggage around finances, and how to reset when conversations go sideways. And since this is the basement, you'll also get practical reminders about key financial deadlines (because nothing kills momentum like IRS penalties), smart ways to teach kids about money, and Doug's festive trivia to keep things light. What You'll Learn: How to talk about money without it escalating into a debate or argument The warning signs of financial secrecy and how to prevent it in any relationship Why shared goals matter more than identical personalities or spending styles Practical ways to align spending, saving, and investing with another person How your childhood money experiences shape your adult financial behavior Smart ways to teach kids patience, work reward connections, and intentional spending Important financial deadlines to keep on your radar Why communication, not math, is often the real key to financial success This Episode Is For You If: You avoid money conversations because they always seem to go badly You're navigating shared finances with a partner, roommate, or family member You want to align financial goals with someone without constant friction You're single but have accountability partners or friends you talk money with You believe better communication is the key to better financial outcomes Question for You: What's one money conversation that felt awkward at first but ultimately made a relationship (romantic, friendship, or otherwise) stronger? Drop your answer in the Spotify comments or the Stacking Benjamins Facebook group. You might just help another Stacker start a better conversation. Because in the end, mastering money isn't just about returns. It's about building a life and relationships that work. FULL SHOW NOTES: https://stackingbenjamins.com/relationships-and-money-with-doug-and-heather-boneparth-1802 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Joe Saul-Sehy, OG, and Neighbor Doug pull up a rickety basement chair and unpack a growing trend: people treating investing like a series of high stakes bets instead of a long term plan. Sparked by a recent Wall Street Journal piece on aggressive investing, the gang digs into where the line is between smart risk taking and straight up gambling with your future. Using plenty of real world examples and a few basement metaphors, the crew breaks down how stocks, businesses, options, and even so-called innovative products can fall into very different categories depending on why you're using them. The key theme? Good investing isn't about being bold. It's about understanding probabilities, controlling what you can, and stacking the odds in your favor over time. Along the way, the team also tackles listener questions, including some strong feelings about Costco (because of course), and shines a flashlight into the dark corners of complex products like Indexed Universal Life insurance, explaining why "sounds sophisticated" doesn't always mean "fits your plan." If markets feel noisy, confusing, or a little unhinged right now, this episode is your reminder that boring, disciplined strategies still win, and that you don't need to bet the farm to build one. What You'll Learn: • Why so many investors are confusing betting with investing right now • How to tell the difference between calculated risk and speculation • Why understanding probability matters more than chasing big wins • Where options, businesses, and alternative investments can fit and where they often don't • The hidden risks behind complex products like Indexed Universal Life (IUL) policies • Why compounding beats hype even when headlines say otherwise • How small, consistent decisions quietly outperform flashy moves • Yes, what Costco has to do with smart money choices This Episode Is For You If: • Markets feel confusing and you're not sure if you're investing or just guessing • You've been tempted by strategies that sound sophisticated but feel risky • You want to understand the line between smart risk and gambling • You're tired of flashy investment advice and want clarity on what actually works • You need reassurance that boring, disciplined strategies still win Question for You: What's the riskiest financial move you've ever considered, and what stopped you (or didn't)? Share your answer in the Spotify comments or the Stacking Benjamins Facebook group. Bonus points if hindsight made you laugh or wince. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Eighteen hundred episodes calls for something special, and what better way to celebrate than by dragging the absolute worst money advice into the light and laughing at it together? Special guest and CFP Sarah Catherine Guiterrez from Aptus Financial joins Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) for a rapid-fire, no mercy takedown of the most damaging financial clichés ever passed down at family dinners, car dealerships, and internet comment sections. This episode is equal parts group therapy, myth-busting, and friendly argument. Exactly the kind of chaos that's kept the Stacking Benjamins basement standing for 1,800 shows. What You'll Hear in This Milestone Episode: • The most cringeworthy financial advice the panel has ever heard and why it sticks around • Why phrases like "just let the bank take it" quietly wreck long-term wealth • How YOLO thinking sneaks into financial decisions disguised as confidence • The difference between common advice and useful advice • Sarah Catherine's planner level perspective on why bad advice feels comforting • Paula and Jesse sparring over long term thinking versus short term emotion • OG bringing strategy, clarity, and the occasional eye roll • Neighbor Doug doing what he does best: poking holes, cracking jokes, and keeping everyone honest • Why car buying advice is one of the most misunderstood areas in personal finance • How trivia, travel, and history collide in a surprisingly competitive game segment • What Singapore's founding teaches us about perspective, patience, and getting the facts right • Why smart money decisions usually sound boring but work anyway This Episode Is For You If: • You've ever heard money advice and thought, "Wait, people actually believe that?" • You're tired of conflicting financial wisdom and want validation that some of it IS terrible • You've been burned by advice that sounded good but cost you money • You want to hear smart people argue about what actually works versus what just sounds good • You've been with us since episode 1, or just wandered into the basement and want to celebrate This episode is a love letter to Stackers who question conventional wisdom and trust their gut when advice doesn't add up. It's loud, opinionated, funny, and packed with reminders that the best financial moves often start by ignoring the advice everyone else is shouting. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Whitney Elkins-Hutten's story isn't about overnight success or getting lucky. It's about building a wealth machine that keeps working even when life throws curveballs. Broadcast as always from Joe's mom's basement, this episode explores how Whitney went from a modest, very 1970s upbringing to creating systems that generate lasting wealth, and what everyday people can realistically take from her experience. Yes, she built an $800 million real estate portfolio, but this conversation is about something bigger: how to create income systems that compound, scale, and eventually run without you. Along the way, Joe Saul-Sehy, OG, and Doug connect the dots between mindset, cash flow strategies, and protecting what you've already built in a world full of digital landmines. What You'll Take Away: • Why Whitney's early mistakes became her biggest long term advantages • How to think about building cash flow engines, not just accumulating assets • The difference between owning things and building repeatable income systems • Why passive income still requires intentional structure and where people go wrong • How mentorship accelerates progress and what to look for in the right mentor • Practical ways to get started building wealth systems without massive capital • Why diversification across income streams matters more than most people realize • What unexpected businesses like car washes teach us about operational efficiency • How subscription models and recurring revenue quietly stabilize cash flow • The long game of turning short term decisions into generational wealth • Why protecting your personal data is now part of protecting your net worth • How small habits (financial and otherwise) compound into outsized results This Episode Is For You If: • You want to build wealth that lasts beyond your lifetime • You're curious about creating income systems that don't require your constant attention • You're tired of overnight success stories and want the real trajectory • You're looking for principles that work whether you invest in real estate, businesses, or other assets • You believe smart systems and consistent learning can change your family's financial future This episode is for Stackers who want proof that progress doesn't require perfection, and that building the right wealth machine can change the entire trajectory of your financial life and your family's future. FULL SHOW NOTES: https://stackingbenjamins.com/building-generational-wealth-with-whitney-elkins-hutten-1799 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

Taxes don't have to feel like something that happens to you. Joe Saul-Sehy, OG, and Neighbor Doug break down the biggest recent tax changes and, more importantly, how to use them intentionally instead of accidentally leaving money on the table. This isn't about memorizing the tax code or becoming a DIY CPA. It's about understanding where the real opportunities are right now, which moves matter most at different life stages, and how smart planning today can quietly add up to thousands of dollars over time. From new deductions to retirement-focused strategies, this episode helps you move from reacting at tax time to planning all year long. What You'll Learn: • The most important recent tax changes and who actually benefits from them • How the expanded SALT deduction works and when it matters • What the new senior deduction could mean for retirees and near retirees • Why maximizing retirement accounts isn't just about saving for later but lowering taxes now • How Health Savings Accounts create one of the most powerful tax advantages available • When tax loss harvesting helps and when it's mostly noise • Why managing your tax bracket in retirement can be as important as investment returns • Smarter charitable giving strategies that align generosity with tax efficiency • How education savings tools fit into a broader tax plan for those who need them • Common tax season mistakes that quietly cost people money every year This Episode Is For You If: • You suspect you're paying more in taxes than you should • Tax planning feels overwhelming so you just deal with it in April • You want to understand which tax moves actually matter at your life stage • You're tired of hearing about strategies that don't apply to your situation • You're ready to stop reacting to taxes and start planning for them This episode is for anyone who wants their tax strategy to support their bigger financial goals, not work against them. If you're looking to keep more of what you earn and make fewer "wish I'd known that earlier" decisions, this is one to queue up. FULL SHOW NOTES: https://stackingbenjamins.com/tax_planning_moves_for_2026-1798 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 path to better money decisions, more confidence, and a calmer life wasn't a massive overhaul but just getting a tiny bit better today than you were yesterday? Joe Saul-Sehy, Neighbor Doug, OG, and Paula Pant (Afford Anything) are joined by David Gillis, creator of the 1% Better Conference, for a roundtable exploring the surprisingly powerful idea of improving by just 1% at a time. No vision boards. No 5 a.m. ice baths. Just small, intentional choices that compound into real results, financially and otherwise. David brings practical insight and zero guru energy into what sustainable improvement looks like. Together the group talks about why most people burn out trying to change everything at once, and how Stackers can instead design days that make better decisions easier. You'll hear honest conversations about energy drainers (including the ones we pretend aren't draining), why saying "no" is often the most underrated financial skill, and how rest, relationships, and even boredom play a bigger role in success than grinding ever will. There's also a healthy reminder that progress doesn't always look productive, and that's okay. As always, Doug brings the trivia, the basement brings the banter, and the lesson sneaks up on you when you're not looking. If you've ever felt like you should be doing more but don't want to torch your sanity getting there, this episode is for you. If the 1% Better philosophy resonates with you, the 1% Better Conference is happening February 21-22 in Omaha, where Joe will be the keynote speaker. What You'll Learn: Why 1% better beats "start over Monday" every single time How to identify the biggest energy leaks hurting your money decisions Why learning to say "no" can improve your finances immediately How rest, nature, and relationships quietly boost long term success Why small habits matter more than motivation How to grow personally and financially without burning out A realistic framework for steady improvement that fits real life This Episode Is For You If: You're exhausted from trying to overhaul everything at once You feel like you should be doing more but you're already maxed out You want progress that doesn't require torching your current life You're tired of all or nothing approaches that leave you burnt out You're ready for sustainable improvement instead of another failed fresh start Question for You: What's one small change you could make this week that would make your life or money just a little easier? Drop it in the comments or share it with us in the Basement Facebook group. We promise not to turn it into a 30 day challenge with a workbook. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Where do great ideas come from, and why do they always show up in the shower, on a walk, or five minutes after you've stopped trying so hard? Joe Saul-Sehy, OG, and Neighbor Doug welcome this week's mentor, behavioral scientist George Newman, to unpack how creativity really works and how Stackers can use it to make better decisions with money, careers, and life. This isn't about becoming "more creative" in a woo-woo sense. It's about understanding the conditions that consistently produce better ideas. George explains why your best thinking doesn't come from grinding harder but from combining curiosity, expertise, and space to think. The crew digs into why incremental improvement (the famous "1% better" mindset) often beats chasing giant breakthroughs, and how that approach applies just as well to financial planning as it does to business, habits, or personal growth. You'll also hear why surveying the landscape before acting leads to smarter money moves, how relaxing your brain can unlock solutions you didn't know you had, and why most people already have access to better ideas but don't recognize them yet. Whether you're trying to improve your finances, rethink your career, or simply stop overthinking every decision, this episode gives you a practical framework for generating smarter ideas without burning yourself out. What You'll Learn: Where great ideas are most likely to come from (hint: not when you're stressed) Why expertise plus curiosity beats raw inspiration every time How the 1% better philosophy creates long term breakthroughs The role relaxation plays in clearer thinking and decision making Why surveying your options first leads to better financial outcomes How small experiments like paper trading improve confidence before real world action Why coaching, reflection, and time horizons matter more than quick wins This Episode Is For You If: You feel like you're working harder but not thinking better Your best ideas come when you're NOT trying to force them You're exhausted from grinding and want a smarter approach You want to improve your finances but feel stuck in the same patterns You're ready to stop chasing breakthroughs and start making steady progress Questions to Think About: When do your best ideas usually show up, and what are you doing when they arrive? What's one area of your finances that could improve with a "1% better" mindset? Drop your answers in the comments or the Basement Facebook group because George's framework for generating better ideas might shift how you approach everything. FULL SHOW NOTES: https://stackingbenjamins.com/where-do-your-best-ideas-come-from-1796 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 made a money move that felt right then immediately wondered if you just emotionally invested in a bad idea? We've all done it. Some of us have receipts. Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the trickiest parts of personal finance: knowing when to trust your gut and when your gut needs to sit down and let the math speak. Because here's the thing. Most Stackers aren't struggling because they don't know what a Roth IRA is. You're struggling because real life decisions don't happen in a spreadsheet. They happen in the middle of a busy Tuesday, with a dozen tabs open in your brain and a million little "what ifs" fighting for attention. So the guys dig into how intuition works (and when it betrays you), and why data is powerful until you start using it to talk yourself into doing something dumb with extra steps. You'll also hear how the best financial plans aren't built on perfect predictions but on repeatable decisions. Plus the episode veers into some surprisingly useful territory with Costco membership strategy, the hidden psychology of "good deals," and how advisors use tools to help optimize Social Security choices without making you feel like you need a PhD in government paperwork. What You'll Learn: How to tell the difference between good intuition and financial anxiety in a trench coat Why data can be a superpower or a weapon you use against yourself The role of AI and research in decision making and what it means for everyday people How OG thinks about sticking to a plan when emotions get loud Why "a deal" can be a budget win or a trap door What a Costco membership is really doing to your spending habits The Social Security optimization tools advisors use and why timing decisions matter This Episode Is For You If: You've made emotional money decisions you later regretted You either overthink every financial choice or jump too fast without enough info You're not sure when to trust your instincts versus when to run the numbers You want to make confident decisions without needing perfect information You're tired of second guessing yourself every time money is involved Questions to Think About: When was the last time your gut feeling saved you financially or cost you money? Are you more likely to overthink decisions with too much research or jump too fast without enough? Drop your answers in the comments or the Basement Facebook group because finding your balance between intuition and data might be the unlock you need. FULL SHOW NOTES: https://stackingbenjamins.com/should-you-trust-your-gut-or-data-1795 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

Inflation may be doing its best to body slam your budget, but this episode is all about fighting back without turning your life into a sad spreadsheet. Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) are joined by special guest Justin Brown-Woods (Price of Avocado Toast) for a roundtable tackling the big question Stackers keep asking: Why does life feel so expensive even when I'm doing everything right? Instead of the usual "just cut lattes" advice, the crew digs into what's really happening. How to calm chaotic expenses. How to stop getting ambushed by "random" costs that aren't random. How to build a plan that makes your money feel predictable again. The conversation hits the real pressure points: food, housing, subscriptions, and the sneaky spending that doesn't look dangerous until it adds up. If you've ever looked at your bank account and thought "Wait, where did that go?" this episode will help you spot the leaks, tighten the system, and still enjoy your life while you do it. What You'll Learn: • How to stop chaotic expenses from wrecking your month • The difference between fixed and variable spending, and why it matters more than you think • Practical ways to lower food costs without eating sadness for dinner • Why housing is the heavyweight champion of your budget and what to do about it • How subscriptions quietly drain cash even when you barely use them • The best way to cut costs without feeling punished • Why mandatory expenses are often more negotiable than you've been told This Episode Is For You If: • You feel like you're doing everything right but still barely keeping up • Your bank account keeps surprising you with where the money goes • You're tired of frugality advice that makes life feel like punishment • You want to cut costs without giving up everything that makes life worth living • You're ready to calm the chaos and make your spending feel predictable again Questions to Think About: What's one expense that used to feel normal but now feels completely ridiculous? Which category gets you more: food spending, housing, or the sneaky monthly subscriptions? Drop your answers in the comments or the Basement Facebook group because this roundtable's framework for taming chaotic spending might be exactly what you need. FULL SHOW NOTES: https://stackingbenjamins.com/how-to-afford-the-new-normal-1794 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 your money stopped dictating your schedule and started supporting the life you actually want to live? Joe Saul-Sehy welcomes CFP Dana Anspach of Sensible Money as special guest co-host for an episode featuring this week's mentor, Andy Hill. Andy shares how he stepped away from the corporate grind, redesigned his priorities, and built a life where family and flexibility came first. His story isn't about escaping work. It's about building a financial foundation that gives you options. Then the conversation shifts to a headline that caught everyone's attention: NASCAR driver Kyle Busch and his wife Samantha are suing their insurance company, calling the life insurance they purchased "a scam." Dana uses this case to break down one of the most misunderstood areas in personal finance: life insurance. From Indexed Universal Life (IUL) policies to knowing when insurance is a tool and when it's a distraction, she shows how clarity of goals should drive every decision and how to avoid the traps that caught even high earners like the Buschs. The episode also touches on estate planning, scams to watch out for, how young adults should think about budgeting and debt, and how to evaluate whether paying off loans or investing is the better move for your situation. It connects the dots between time freedom, smart planning, and protecting what you're building. What You'll Learn: • How to design your finances around the life you want, not just the paycheck you earn • What "owning your time" really means and how to start moving in that direction • Why your financial plan should begin with values and priorities, not products • How to think about entrepreneurship without blowing up your financial stability • What the Kyle Busch insurance lawsuit reveals about life insurance products and sales tactics • The truth about Indexed Universal Life insurance and when it may or may not make sense • How to evaluate life insurance based on goals instead of sales pitches • How estate planning protects your family and your legacy • The pros and cons of paying off loans versus investing • Budgeting principles that help young adults build strong money habits early • How to recognize and avoid financial scams (including insurance product traps) • Why celebrating progress matters just as much as setting the next goal This Episode Is For You If: • You feel like your money controls your life instead of supporting it • You want more flexibility and time freedom but don't know how to fund it • You're confused about whether life insurance products are helping or just costing you (especially after hearing about the Busch lawsuit) • You're trying to figure out the right order of financial moves (debt vs investing, insurance vs saving) • You want your financial plan to reflect your actual values, not just what you're "supposed" to do This episode is about aligning your money with your life. If you're ready to stop reacting to your finances and start using them to build more freedom, flexibility, and confidence, this one belongs at the top of your queue. FULL SHOW NOTES: https://stackingbenjamins.com/own-your-time-with-andy-hill-and-dana-anspach-1793 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 your money questions don't fit neatly into one category? One minute you're thinking about retirement, the next it's insurance, emergency funds, gifting money, or whether your workplace plan is helping or hurting you. This is one of those episodes where Stackers bring the real-life questions, and Joe Saul-Sehy, CFP Anna Allem, and Neighbor Doug help sort through the noise. It's a true Q&A show built from the issues you're wrestling with right now. No perfect spreadsheets. No one-size-fits-all answers. Just practical guidance for making smart decisions when your financial life has a lot of moving parts. You'll hear how to prioritize when everything feels important, how to adjust your strategy as rules change, and how to stay flexible without losing control of your long-term plan. College planning comes up, but it's part of a bigger conversation about balancing competing goals, not the center of the episode. What You'll Learn: • How to make better decisions when multiple financial priorities collide • Smarter ways to think about life insurance when cash flow feels tight • How to build or rebuild an emergency fund with inconsistent income • What changes to 401(k) rules could mean for your saving and investing strategy • When opting out of a workplace plan might make sense, and when it's a mistake • How automatic enrollment and contribution changes can impact your future wealth • The right way to gift money to kids or grandkids without creating tax or planning problems • How HSAs fit into your bigger financial picture • Why financial gridlock happens and how to break through it • How to balance short term flexibility with long term security • A clear explanation of FAFSA and financial aid, and how it fits into overall planning for families who need it This Episode Is For You If: • You're juggling multiple financial priorities and not sure which one to tackle first • You feel stuck because everything seems important and nothing feels urgent enough • You want guidance that fits your messy real life, not just textbook answers • You're tired of financial advice that assumes you only have one problem at a time • You need permission to prioritize imperfectly and still make progress If your finances feel like a maze, this is your map. FULL SHOW NOTES: https://stackingbenjamins.com/answering-stacker-questions-with-anna-allem-1792 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

Some people kick off a new year with a vision board. We prefer a runway show in sweatpants from Joe's mom's basement. Joe Saul-Sehy, OG, and Neighbor Doug throw personal finance into the spotlight and ask the question every Stacker secretly loves: What's officially "so last year" in your money plan, and what's worth keeping for 2026? Because here's the truth. You don't need a total financial makeover. You need a few smart "wardrobe swaps" that fit your real life. The habits that quietly drain your progress (hello, lifestyle creep). The stuff people obsess over that doesn't matter as much as they think. And the overlooked moves that make everything else easier. The crew breaks down what's out (financial habits that looked good but never delivered), what's in (the practical moves that reduce stress and create actual progress), and why real financial planning isn't just about investments but about building a system that holds up when life gets messy. Also on the docket: a fresh start to the yearlong trivia competition with new rules, new twists, and the kind of competitive energy that makes you wonder if the trophy comes with a safety warning label. What You'll Learn: • What financial trends are out for 2026 and why they weren't helping anyway • The habits that are in if you want more freedom, less stress, and fewer "where did my money go" moments • Why real financial planning isn't just investments but a system that works in real life • How lifestyle creep sneaks in and a couple ways to stop it before it becomes your full-time hobby • What tax strategy means for normal people, not just spreadsheet enthusiasts • The money conversations you should have early in the year before life gets loud again • A realistic take on housing in 2026 and what to focus on when markets don't behave • New trivia rules including a twist that changes everything if you're not paying attention This Episode Is For You If: • You want to know what to stop doing so you can focus on what works • You're tired of financial advice that adds more tasks instead of clarity • You suspect some of your money habits aren't pulling their weight • You want permission to quit the financial trends that never fit your life • You're ready for a few strategic changes that make 2026 feel more manageable Questions to Think About: What's one money habit you're officially retiring in 2026? If you could upgrade one part of your financial plan this year, what would it be: spending, saving, investing, insurance, or taxes? Drop your answers in the comments or the Basement Facebook group because this episode is all about figuring out what stays and what goes. FULL SHOW NOTES: https://stackingbenjamins.com/finance-hot-or-not-2026-1791 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