The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
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  • Deux fois par semaine

Named Best Personal Finance Podcast by Bankrate.com and Kiplinger — and the only podcast the Plutus Awards retired from competition after winning twice — The Stacking Benjamins Show is personal finance that doesn’t put you to sleep. Hosts Joe Saul-Sehy (former 16-year financial advisor, ex-WXYZ-TV “Money Man”) and Josh “OG” Bannerman, CFP (Certified Financial Planner, Bannerman Wealth) sit around the card table in Joe’s mom’s half-finished basement in Texarkana and talk money with the smartest guests in personal finance, investing, and behavioral economics. As Fast Company wrote, the show “strikes a great balance of fun and functional.” Every Monday, Wednesday, and Friday: expert guests, real headlines, listener questions, and Doug’s trivia. Topics include investing, retirement planning, budgeting, real estate, behavioral finance, taxes, and financial independence — for anyone who wants to be smarter about money without being talked down to. Subscribe to The 201 — the free newsletter that goes deeper than the show — at stackingbenjamins.com/201

  1. -5 h

    Jesse Mecham (YNAB Founder) On The One Question That Ends Money Anxiety For Good (SB1879)

    There's a strange thing that happens to a lot of people as their income grows: the anxiety doesn't go away, it just changes shape. More money, more accounts, more to track, and somehow the same low hum of worry every time a bill comes due. Jesse Mecham, founder of YNAB and one of the most trusted voices in budgeting, has spent over two decades helping people fix that, and his conclusion isn't a better spreadsheet or a stricter budget. It's a single question, one that sounds almost too simple to matter, until you actually try to answer it. What You'll Walk Away With The one question that replaces budgeting guilt with genuine clarity, and why it works even for people who "already have money figured out"Why looking backward at your spending almost never makes you feel better, and what to do insteadThe five categories every dollar actually falls into, and why skipping even one of them creates financial blind spotsWhy future income should never be allowed to rescue your current plan, and how that habit quietly leads to credit card debtA surprisingly simple system for making irregular bills stop feeling like emergenciesThe real story of a Costco cashier who became a millionaire without doing anything complicated, and what it says about the myth of needing to "get fancy" with moneyWhy money worry doesn't disappear once you have more of it, and what actually makes it go awayWhy This Matters Now It's easy to assume that financial peace is just one income bump away. Get the raise, pay off the card, hit the next savings milestone, and the anxiety will finally quiet down. But that's rarely how it actually works. Real financial confidence comes from knowing exactly what your money is for, not from having more of it. That clarity is available at any income level, and it's the difference between managing money and constantly feeling managed by it. From the Basement A story about a seventh-grade inline skating competition, complete with donated gear, mystery sponsors, and an unauthorized parking lot, turns out to be the unexpected origin story behind one of personal finance's most beloved communities. Some of the best lessons about building something people care about show up in the most unlikely places. Resources Mentioned Never Worry About Money Again by Jesse Mecham — Jesse's new book on purpose-based spendingYNAB (You Need A Budget) — Jesse's budgeting app and free trial See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  2. -2 j

    Your Mid-Year Tax Checkup: Fix Problems Before They Become April's Problem (SB1878)

    Most people only think about taxes twice a year: while filing, and while dreading filing next time. That gap is exactly where expensive surprises are born. Today's episode is a genuine mid-year tax tune-up, the kind of checkup that takes maybe twenty minutes and can quietly save you from an ugly bill, an unexpected penalty, or a refund that wasn't actually a win. No jargon-heavy lecture, just a clear walkthrough of what to check right now while there's still time to fix it. What You'll Walk Away With Why a big tax refund last year tells you almost nothing about whether you're on track this yearThe four numbers you actually need to know to build your own mini tax forecast in one sittingHow the IRS "safe harbor" rule works, and the two different percentage thresholds that keep you penalty-freeA common myth about side hustle income that trips up more people than you'd expectWhy switching to a Roth 401k without a plan can quietly blow a hole in your monthly cash flowThe real math behind donor-advised funds, and why writing a check to charity may be leaving money on the tableA simple gut-check for figuring out whether you need a professional or can handle a financial fix yourselfWhy This Matters Now In your 40s, your financial life usually gets more complicated before it gets simpler: a raise here, a side hustle there, maybe two incomes in the household, maybe a bonus that shows up at an inconvenient time. Each of those changes quietly shifts what you owe, and waiting until April to notice means you've lost your best chance to do anything about it. A twenty-minute check now isn't about becoming a tax expert. It's about making sure next spring is boring instead of stressful, which, when it comes to taxes, is exactly the goal. From the Basement A home AC disaster turns into an unexpectedly useful lesson about getting a second opinion before writing a big check, whether it's for a repair, a service, or apparently, a $3,000 HVAC estimate that turned out to be a $300 fix. Consider it a bonus lesson in trusting your gut when something doesn't add up. Resources Mentioned Stacking Benjamins Tax Guide — free guide for organizing your mid-year tax reviewStacko Financial Action Month board — the interactive game with a money move for each dayField Kit Finance — track net worth, spending, and subscriptions in one placeDaffy — donor-advised fund platform referenced for charitable giving strategyIRS Estimated Tax Payments — where to make an estimated payment directly See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  3. -5 j

    Why Smart People Make Dumb Money Decisions SB1877

    Three genuinely sharp financial minds sit down today and, one by one, admit to the same kind of dumb money moves everyone else makes. Not because they didn't know better. Because knowing better and doing better turn out to be two completely different skills, and your brain is very good at making bad ideas feel reasonable in the moment. This episode isn't about learning new investment tactics. It's about learning to recognize the exact moment your own mind starts working against you, and what to do about it before it costs you. What You'll Walk Away With The three specific flavors of overconfidence that combine into what one expert calls "a recipe for disaster"Why "I'll wait until it comes back" is one of the most dangerous sentences an investor can say to themselves, and when it's actually trueThe surprising reason financially literate people still make emotional money mistakes, according to research on an unrelated professionA simple writing exercise that makes you far more likely to stick to your own financial planWhy betting on what's familiar, your employer's stock, your home country's market, is quietly one of the riskiest things you can doA martial-arts-inspired mental trick for turning your own biases into tools instead of trapsThe real reason "this time is different" almost always feels true and is almost always the wrong conclusion to act onWhy This Matters Now In your 40s, you've likely made enough financial decisions to have a track record, some smart, some you'd rather not revisit. The goal isn't to eliminate emotion from money; that's not realistic, and it's not even the point. It's to recognize the specific moments your gut is about to overrule your plan, and to have something in place, a rule, a person, a system, that catches you before it does. Confidence with money doesn't come from never being tempted to make a bad call. It comes from knowing exactly what you'll do when you are. From the Basement The crew's year-long trivia championship takes a wild turn with a Spanish treasure fleet question that somehow ends in someone getting bonus points for pure luck, which is a fittingly ironic way to close an episode all about how bad we are at judging our own luck. Resources Mentioned The Behavioral Investor by Daniel Crosby — second edition available for preorderAfford Anything podcast — Paula Pant's showPersonal Finance for Long-Term Investors podcast — Jesse Cramer's show See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  4. -6 j

    Why Your Homeowners Insurance Bill Keeps Going Up (And What to Do About It) Special Episode SB1876

    Homeowners insurance prices are up a whopping 24% since 2022. One in seven homeowners now has no insurance at all. In some parts of the country, companies aren't just raising rates -- they're refusing to write policies. Bob Litterman co-created the Black-Litterman model that the financial industry still uses to price risk, spent 23 years running risk at Goldman Sachs, and now chairs the Coalition for an Insurable Future. He joins Joe and OG on a special Thursday episode to explain what's actually happening, why it's not going to stop, and what you can do about it right now. What You'll Walk Away With Why the insurance market breaks down when probabilities stop being stable -- and how billion-dollar weather events went from three per year in the 1980s to 23 per year todayThe domino chain: how rising insurance costs in one ZIP code can drive down home values, freeze bank lending, shrink local businesses, and quietly hollow out an entire communityWhy this isn't 2008 -- and the one important way it's actually worse than what the mortgage crisis taught usWhy one in seven homeowners now carries no insurance at all -- and what that means for the next major weather eventThe 100-year flood problem: why homes built to withstand a once-in-a-century event are now getting hit every five to ten yearsWhat first-time homebuyers should ask that their realtor almost certainly won't bring up -- and why the insurance question is now as important as the mortgage rateHow to actually read your renewal letter: what to look for beyond the premium, what hidden changes insurance companies are legally required to disclose, and why your deductible may have quietly doubledOG's Claude trick: how he uploaded both his old and new policy documents, asked for the differences, and found actionable savings plus a jewelry rider gap he didn't know he hadWhy Bob says the real mispricing isn't in the insurance market -- it's in the pollution market -- and what that means for how this eventually gets resolvedThe risk management reframe: why thinking about insurance is the wrong starting point, and what to think about insteadWhy This Matters Now This isn't an inflation blip. The risk is genuinely increasing, the models are being rewritten in real time, and the insurance companies pulling out of markets are the canary in the coal mine. The good news: there are specific things you can do right now -- at your house, with your policy, and in how you think about risk -- that most homeowners haven't done yet. From the Basement Bob Litterman joins Joe and OG on a special Thursday episode to walk through the home insurance crisis from the inside -- the pricing models, the domino chain, the reinsurance squeeze, and the difference between a tail event and the slow-moving sea level rise underneath it. OG's takeaway: upload both your old and new policy to Claude and ask it to find the differences before your next renewal. Doug arrives with flood insurance trivia tied directly to the episode content. The Coalition for an Insurable Future, a nonpartisan cross-industry group, made this episode possible. Stacking Benjamins received compensation for this episode. Resources Mentioned Coalition for an Insurable Future -- nonpartisan cross-industry group on climate and insurance risk; coalitionforaninsurablefuture.comBlack-Litterman Model -- referenced for Bob Litterman's background in risk pricingClimate Central -- tracks billion-dollar weather events annually; climatecentral.orgNational Flood Insurance Program -- referenced for the 1968 government backstop for flood risk; floodsmart.gov See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  5. 29 juil.

    Meet the Family That Quietly Controls Your Retirement Money (SB1875)

    Odds are good that part of your paycheck disappears into an account with the Fidelity name on it every two weeks. Almost nobody stops to ask who's actually on the other end of that relationship. The answer isn't a faceless Wall Street institution, it's one family that has quietly controlled a $15 trillion company for three generations, through boardroom near-mutinies, a succession fight that almost ended in the company being sold, and enough family drama to fill a book. It did, actually. Wall Street Journal reporter Justin Baer spent years uncovering it, and today he brings the whole story down to the basement. What You'll Walk Away With Why one of the biggest financial companies in America has never had a single outside shareholder, and what that's actually protected them fromThe surprisingly personal origin story behind Fidelity's founder, and the market-crash lesson that shaped the entire company's philosophyWhy Fidelity almost missed the money market fund revolution, and the workaround that changed how everyday people access their cashThe near-sale that almost happened in 2005, and how close the company came to becoming something completely differentWhy checking your 401k balance more often might actually be good for your financial decision-making, according to Fidelity's own researchHow a family succession battle nearly pushed the current CEO out of the business entirelyA useful mental gut-check for figuring out how much of your "checking account cushion" should actually count as part of your emergency fundWhy This Matters Now If you're in your 40s, there's a good chance you've had a relationship with Fidelity, Vanguard, or a similar company for two decades without ever really knowing how they work or who's behind them. That's not a knock on you, it's just how most financial relationships start: automatically, through a job, without much choice involved. Understanding the incentives and history behind the company holding your retirement money doesn't change your investing strategy overnight, but it does replace a vague, faceless trust with something more informed, and informed trust is a lot more durable than blind trust. From the Basement A conversation about $189 average dates turns into a surprisingly sharp point about not overspending to impress someone before you even know if it's a match, in relationships or business. And a basement community note about "hidden" emergency funds sitting in checking accounts sparks a genuinely useful reframe worth stealing for your own budget. Resources Mentioned House of Fidelity: The Rise of the Johnson Dynasty and the Company That Changed American Investing — Justin Baer's book on the Johnson family and Fidelity's historyField Kit Finance — the all-in-one net worth, budgeting, and credit tracking tool mentioned in the sponsor break See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  6. 28 juil.

    The One Financial Conversation People Avoid (Plus a Discussion about Stress and Money) SB1874

    There are three words that quietly end up costing more than almost any bad investment: "he handles it." Not because delegating is wrong, but because somewhere between division of labor and total disengagement, a line gets crossed that most couples never notice until a crisis forces them to. This episode is about that line, and about the less obvious ways money stress shows up when it's not just a spreadsheet problem, it's a physical one. Jill Schlesinger and Kristy Talorico both join the show, and each brings something you didn't know you needed to hear. What You'll Walk Away With The real difference between splitting responsibilities and losing all visibility into your own financial lifeA simple, low-stakes way to start a money conversation with a partner who's checked out, without triggering defensivenessWhy financial advisors dread meeting a client's "uninvolved" spouse for the first time after a deathWhat actually happens to your financial life if your money-handling spouse suddenly can't do it anymoreHow financial stress physically changes your body, according to a major new health studyWhy the standard advice to "just put more in your 401k" completely misses people who are financially struggling right nowThe surprising first place financial counselors suggest looking before you take out any kind of loanA behind-the-scenes look at how employers are (and aren't) using workplace benefits to actually help peopleWhy This Matters Now In your 40s, you're often the connective tissue for your whole household's financial life, sometimes for a spouse, sometimes for aging parents, sometimes for kids just starting out. It's easy to assume that as long as someone in the relationship understands the money, everyone's fine. But real financial confidence means everyone involved has at least a working map of where things stand. This episode isn't about becoming an expert. It's about making sure "I don't really know" is never the answer when it matters most. From the Basement Doug's trivia question drags in an unexpected lesson about knowing what things actually mean, not just recognizing the name, which somehow ties together German car history and financial literacy in the same segment. Basement logic, but it works. Resources Mentioned Money Moves with Jill Schlesinger — Jill's new podcast with Mark TalercioJill on Money podcast — Jill Schlesinger's long-running personal finance show"The Most Dangerous Words I Hear From Married Couples: 'He Handles It'" — the Kiplinger piece referenced in the episodeBrightside Financial Care — Kristy Talorico's company, financial care benefits for employersFindhelp.org — the free navigation tool for local financial and hardship resources See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  7. 27 juil.

    Everything You Actually Need to Know About Social Security Right Now (SB1873)

    There's a new bill in Washington that sounds like a fix but is really just a promise to eventually have a debate about one. That's not why this episode matters. What matters is that Social Security is suddenly everywhere in the headlines, and if you've been putting off understanding how your own claiming decision actually works, that's a gap that gets more expensive the longer it sits. This episode is the one to finally close it. No single mistake, no one hot take, just a real walkthrough of the claiming ages, the spousal rules, the survivor benefits, and the myths that trip people up most, so you can stop guessing and start deciding with confidence. What You'll Walk Away With Why the "estimated benefit" number on your Social Security account can be wildly wrong, especially if you're not planning to work until 67The real reason waiting until 70 pays off, and why it has almost nothing to do with growthA subtle, surprisingly common mistake that can quietly wreck a smart claiming strategy years after you made itWhat actually happens to your benefit if your spouse passes away first, and how remarriage timing can change everythingWhy the industries where workers never pay into Social Security create a completely different retirement mathThe dollar threshold that can force you to pay back benefits you already claimedA 2024 rule change that may directly affect certain public employees and hasn't gotten nearly enough attentionWhy raising the retirement age matters a lot less than people assume, depending on how you actually want to retireHow a totally different tax, the Medicare surcharge, quietly rides along with your Social Security decisionsA quick true-or-false round that separates Social Security fact from the myths everyone repeatsWhy This Matters Now If you're in your 40s, Social Security can feel like something to figure out later, right up until a headline makes it feel urgent and confusing at the same time. The truth is, you don't need to predict what Congress will do. You need to understand the mechanics that are already in your control: when you claim, how you and a spouse coordinate, and how your own work history shapes the number. Get that right, and you turn a source of money stress into one less thing you have to worry about, freeing up mental space for the parts of your financial life you actually want to think about, like the next trip, not the next committee hearing. From the Basement Doug tests his trivia chops with a game built to separate fact from political fantasy, and OG gets fired up about something that has absolutely nothing to do with retirement, and everything to do with golf tickets. It's the reminder that even a deep dive into claiming strategy still comes with a little basement chaos along the way. Resources Mentioned The PROMISE Act, explained — CNBC's breakdown of the bipartisan bill and the 2032 trust fund deadlineCreate your SSA.gov account — check your earnings history and benefit estimateid.me login for SSA.gov — the identity verification step for your Social Security accountThe Walt Disney Company: Walt's Era — Acquired podcast — the four-hour deep dive Doug referenced on Disney, Oswald the Rabbit, and protecting your nameStacking Benjamins Guides - Scout + a quick and easy checklist are just two of the reasons these complete reference tools are your top choice to manage your HR Benefits, your taxes, or college planning. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  8. 24 juil.

    A Former OpenAI Researcher Says 70% Chance of Human Extinction -- Here's What to Do With That SB1872

    A former OpenAI researcher went on Diary of a CEO and said there's a 70% chance AI ends badly for humanity, told his wife they shouldn't have more children because they'd never enter the workforce, and gave up $2 million by refusing to sign a non-disparagement clause to say it publicly. Joe asks Paula Pant, OG, and Jesse Cramer to react -- not as AI experts, but as people who've watched the internet, robots, computers, and cars all supposedly end the economy, and as people who actually know what to do with your money when the world feels uncertain. What You'll Walk Away With Paula's case for being a negative 10 on the worry scale: why 60% of jobs that exist today didn't exist in 1940, and why AI is more likely to create new categories of work than eliminate work entirelyJesse's case for a four: why knowledge is being commoditized the same way gasoline was -- and what that means if your competitive advantage has always been what you knowOG's framework for separating the parts of your job AI will gladly take from the parts it never will -- and why that distinction is more useful than panicking about either halfThe Jevons Paradox: why making something cheaper almost always creates more demand for it, not less -- and why that applies to patents, legal filings, and every other knowledge-work category people think AI will eliminateSafe, evolving, or replaced: the roundtable verdict on CPAs, software engineers, and customer service reps -- and the Capital One research that reveals why some people actually prefer talking to a machineWhy learning the AI tools right now -- even if you're 58 and four years from retirement -- is the modern equivalent of learning email in 1993JL Collins' line that applies to careers just as much as portfolios: flexibility is the only true securityShould you buy an AI sector fund? OG, Paula, and Jesse each answer -- and the answer that surprised everyone is probably not the one you'd expectWhy OG's Triple Bypass bike race analogy is the best career advice in the episode: if you're always ready, you never have to get readyThe window tax trivia that AI got spectacularly wrong -- proving, on an episode about AI taking all our jobs, that it can't even count windows yet Why This Matters Now The fear is real. The timeline is uncertain. And the people most likely to be okay are the ones who are building flexibility into their finances and their careers right now -- not because AI is definitely coming, but because it's always smart to be ready for the thing that might come. From the Basement Paula Pant, OG, and Jesse Cramer react to a former OpenAI researcher's apocalyptic Diary of a CEO interview -- and spend most of the episode arguing about whether to panic, which jobs survive, whether to buy the AI sector fund, and what OG's fighting robot would do to Jesse's house. Doug arrives with window tax trivia that AI generated incorrectly -- which Joe caught just before air -- and handing one of our contributors a huge win. Financial Action Month is coming next week: five episodes, a bingo sheet, and more to come. Resources Mentioned Diary of a CEO -- Steven Bartlett interview with Daniel Kokotajlo, former OpenAI researcherTony Robbins interview with Ray Kurzweil -- referenced for additional AI perspective; linked at stackingbenjamins.comAfford Anything episode 693 -- Paula Pant interview with Dr. Ben Zweig on AI and the workforce; affordanything.com/episode693Personal Finance for Long-Term Investors (PFLTI) -- Jesse Cramer; upcoming AMA episode 19 and episode 150 personal AMAAnthropic Skill Jar -- free AI training; referenced by Paula for learning Claude featuresDelivering Happiness by Tony Hsieh -- referenced for the Zappos customer service modelOG financial planning calendar -- stackingbenjamins.com/ogStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins Community -- stackingbenjamins.com/basement See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Named Best Personal Finance Podcast by Bankrate.com and Kiplinger — and the only podcast the Plutus Awards retired from competition after winning twice — The Stacking Benjamins Show is personal finance that doesn’t put you to sleep. Hosts Joe Saul-Sehy (former 16-year financial advisor, ex-WXYZ-TV “Money Man”) and Josh “OG” Bannerman, CFP (Certified Financial Planner, Bannerman Wealth) sit around the card table in Joe’s mom’s half-finished basement in Texarkana and talk money with the smartest guests in personal finance, investing, and behavioral economics. As Fast Company wrote, the show “strikes a great balance of fun and functional.” Every Monday, Wednesday, and Friday: expert guests, real headlines, listener questions, and Doug’s trivia. Topics include investing, retirement planning, budgeting, real estate, behavioral finance, taxes, and financial independence — for anyone who wants to be smarter about money without being talked down to. Subscribe to The 201 — the free newsletter that goes deeper than the show — at stackingbenjamins.com/201

Informations

  • Création
    Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
  • Années d’activité
    2013 - 2026
  • Épisodes
    1,5 k
  • Classification
    Contenu explicite
  • Copyright
    © SB Podcast LLC | Gamut Podcast Network
  • Site web de l’émission
    The Stacking Benjamins Show

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