The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
  • 3.8 (25)
  • Investing
  • Updated Twice Weekly

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. 1 day ago

    When Is "Good Enough" Actually Good Enough With Money? SB1884

    There's a version of financial responsibility that looks a lot like discipline but can quietly become something else: an inability to ever stop optimizing. Chasing 0.2% more interest. Driving fifteen minutes out of the way for cheaper gas. Budgeting so tightly that a $5 bottle of multivitamins feels like a crisis. Wealthy Kids Club founder Maya Corbic joins Carol Ann Desiderio and Jesse Cramer for a genuinely fun debate about where the line actually sits, and what over-optimizing quietly costs when nobody's counting it. What You'll Walk Away With A simple test for telling the difference between smart optimization and time-wasting perfectionismWhy budgeting "until it hurts" can quietly damage your relationship with money more than it helpsThe real math behind small optimizations, like driving out of your way for cheaper gas or chasing a slightly higher savings rate, and when they're actually worth itA reframe on "one more year" retirement thinking that flips the entire question aroundWhy letting kids make small, reversible money mistakes teaches more than any lecture ever couldThe surprising overlap between "still researching the best option" and simply avoiding a decisionWhy the biggest lever in your investment returns has almost nothing to do with picking the "best" individual stockWhy This Matters Now It's easy to assume that more research, more comparison, more fine-tuning always makes for a better financial decision. But there's a point where that instinct stops protecting you and starts costing you, in time, in joy, and sometimes in the decision never actually getting made at all. Recognizing when a plan is genuinely good enough isn't giving up. It's redirecting your energy toward the things optimization can't fix: time with people you love, work that fulfills you, and a life that isn't built entirely around squeezing out one more percentage point. From the Basement A wild detour into the 1964 Great Plymouth Mail Truck Robbery keeps the crew's year-long trivia race razor close, while an entirely unrelated cookie heist upstairs in mom's kitchen proves that not every optimization scheme goes according to plan. Resources Mentioned Wealthy Kids Club — Maya Corbic's family financial education programPersonal Finance for Long-Term Investors podcast — Jesse Cramer's show, referenced episode: "Is My DIY Financial Plan Working?"Stacking Benjamins Benjamins After Dark meetups — local in-person Stacker meetup groups, including BostonGranola — AI-powered meeting notes 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.

  2. 3 days ago

    Len Penzo: The 18-Year Sandwich Survey That Predicts Recessions (SB1883)

    Every year, Len Penzo prices out the exact same ten brown-bag sandwiches, using the exact same methodology, at the exact same time of year, and turns it into one of the most oddly reliable inflation trackers around. This year the numbers are ugly: double-digit jumps across the board, an 80% spike in one ingredient alone, and a genuinely surprising twist involving the humble bologna sandwich that Len says has quietly tracked economic downturns for nearly two decades. Then, a headline that should make every family pause: how one daughter used a single signed document to quietly drain nearly a million dollars from her own father. What You'll Walk Away With Which sandwich ingredient jumped a jaw-dropping 80% this year, and why it's not the one you'd expectThe strange, long-running correlation between bologna sales and economic recessionsSimple substitutions, buying whole meats and block cheese instead of pre-sliced, that can meaningfully cut your grocery billWhy "nominally the highest price ever" doesn't always mean "the most expensive it's ever really been," once you adjust for inflationHow a single signed power of attorney document led to nearly $1 million disappearing from a vulnerable parent's accountsThe real difference between what your estate plan says and what your actual account beneficiary designations say, and why that gap can undo your entire planA billionaire's surprisingly simple family money ritual that keeps inheritance conflicts from tearing families apartWhy This Matters Now Grocery prices are one of those slow, quiet costs that are easy to underestimate until you actually look at the numbers side by side. At the same time, the legal documents meant to protect aging family members, like power of attorney, only work as intended when there's real transparency and real trust behind them. Both stories point to the same underlying idea: the clearest financial protection usually isn't a clever trick, it's paying close attention to the details that are easy to assume are already handled. From the Basement A story about a backyard grill fire escalates into a genuinely useful (and slightly panicked) lesson on fire extinguisher use, corrosive foam and all, proving once again that the best financial lessons in the basement don't always come from a spreadsheet. Resources Mentioned LenPenzo.com — Len Penzo's full 18-year sandwich survey and price historyHow Kenn Ricci Runs Family Wealth Meetings — the Wall Street Journal piece on transparent family net worth meetings, referenced in the discussionStacking Benjamins Field Kit — the all-in-one budgeting and financial tracking tool See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  3. 5 days ago

    Should You Max Out a 401(k) You Don't Even Like? SB1882

    Three Stackers call into the basement today with three very different problems, but they all boil down to the same uncomfortable question: what do you do when the "obviously right" financial move doesn't feel right? A generous employer match paired with fund choices you're not thrilled about. A tax bracket so low it seems wasteful not to convert. A life that just took a turn nobody expected, and a whole new set of financial tools nobody teaches you about until you need them. Joe, OG, and Anna Allen tackle all three with real, usable answers. What You'll Walk Away With Why turning down a five-figure employer match over fund quality concerns is almost always the wrong move, and the workaround that fixes it anywayThe real difference between an actively managed fund and a passive one, and why "active" isn't automatically a red flagA little-known 401k feature that can give you far more investment control without giving up your matchHow to think through a Roth conversion when your income, your future tax bracket, and even the state you'll retire in are all still unknownThe single mistake that quietly wastes a Roth contribution opportunity for good, since you can never get that calendar year backWhat an ABLE account is, and how it's different from a 529 in a way that matters enormously for a family navigating a new diagnosisWhy a special needs trust often gets layered on top of an existing estate plan rather than replacing it, and the questions worth asking an attorney before that meetingWhy This Matters Now Good financial advice usually comes with fine print that nobody mentions: what to do when the textbook answer doesn't quite fit your actual life. A workplace retirement plan with mediocre fund choices, a temporary low-income window that might not last, a family circumstance nobody could have planned for. The goal isn't finding a perfect answer; it's understanding the real trade-offs well enough to make a confident decision and adjust as life changes. That's true whether the stakes are a few hundred dollars in fees or a lifetime of care for someone you love. From the Basement A Financial Action Month detour into meal planning turns into a genuinely useful AI-assisted grocery hack, plus a spirited debate over Aldi loyalty and the eternal question of what actually counts as a proper turnover pastry. Some debates never get resolved in the basement, and that's exactly as it should be. Resources Mentioned Stacking Benjamins Field Kit — the all-in-one budgeting, net worth, and subscription tracking toolStacko Financial Action Month board — the interactive game with a money move for each squareThree Money Buckets video — Stacking Benjamins' YouTube Financial Basics courseYell Down the Stairs — submit a question for a future episode See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  4. 7 Aug

    What a Bad Boss Is Actually Costing You (SB1881)

    Most people measure a bad boss in bad days: the meeting that went sideways, the credit that got stolen, the comment that stung longer than it should have. Money Mentor Mel Abraham, along with Paula Pant and the crew, argues that's the wrong unit of measurement entirely. A toxic work situation has a real, compounding financial cost, in stalled raises, atrophied skills, drained energy, and years quietly lost to a job that was never going to get better. Today's episode puts a number on it, and gives you the exact steps to build your way out. What You'll Walk Away With Why a bad boss almost always means you're being underpaid too, and the compounding effect that has on your entire careerA simple "stay, fix it, or go" framework for evaluating your specific work situation, tested against real scenariosWhy waiting for the "right time" to leave a toxic job often means waiting far too longThe financial prep work worth doing now, even if your job is fine today, so you're ready to move fast if it isn't tomorrowWhy your skills and confidence can quietly atrophy under a bad boss, even if your paycheck stays the sameHow to separate your relationships with great coworkers from your relationship with a bad workplaceA practical first-week plan for anyone who gets laid off or walks away suddenly, starting with what actually needs to be true immediatelyWhy This Matters Now A difficult boss or a dead-end job rarely shows up as one dramatic moment. It shows up as a slow leak: a raise you didn't ask for, a skill you didn't build, an idea you didn't pitch because you'd stopped believing it mattered. That slow leak is expensive, and it's also fixable. Building financial and career readiness before you need it, savings, low fixed costs, a sharpened skill set, means the decision to leave becomes a choice you're making on your own terms, not a scramble you're forced into. From the Basement The crew's trivia detour into Philippe Petit's famous 1974 high-wire walk between the Twin Towers turns into a surprisingly close four-way guessing game, complete with hometown bragging rights and a mid-season trivia standings shakeup that's still anyone's game. Resources Mentioned Building Your Money Machine by Mel Abraham — Mel's USA Today bestseller on building financial freedomBuilding Your Money Machine podcast — Mel's weekly show on wealth-building and financial freedomAfford Anything podcast — Paula Pant's show, referenced episode: "Should We Retire in Our 40s with $4 Million?"Granola — AI-powered meeting notes 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.

  5. 6 Aug

    What to Do When Insurance Denies Your Claim (And Why They Count on You Giving Up) SB1880

    It's easy to walk out of a rushed appointment, an unexplained bill, or a denied claim and quietly blame the person in the white coat. Doc G (Doctor Jordan Grumet), the hospice physician and longtime Stacking Benjamins favorite, argues that's exactly the wrong target, and that the confusion isn't an accident. Somewhere between the insurance company, the pharmaceutical company, the private equity firm, and the electronic records system, a lot of people are getting paid, and the two groups actually providing and receiving care are left holding the bag. Here's the good news: almost nobody appeals a denial, and appeals win far more often than you'd expect. This episode gives you the real playbook. What You'll Walk Away With The exact first move to make when a claim gets denied, and why documenting it matters more than people realizeWhy a procedure can get pre-approved and still get denied months later, and what to save to protect yourselfA simple "who do you call first" framework for untangling a prescription, billing, or coverage problemThe pharmaceutical industry trick of repackaging old drugs as "new" ones, and the one question that sidesteps it completelyHow to spot whether your doctor's office is privately owned or backed by private equity, and why it changes the care you getWhy so much unnecessary testing exists purely to protect doctors from lawsuits, not to protect youThe real math on insurance appeals, and why giving up is exactly what the system is counting onWhy This Matters Now Healthcare confusion isn't just an annoyance, it's a real financial risk hiding in plain sight. A denied claim, a surprise bill, or a medication that suddenly isn't covered can undo months of careful budgeting in a single afternoon. The difference between losing that fight and winning it usually isn't luck, it's knowing the specific, doable steps to push back before you give up. This isn't about becoming your own doctor or insurance expert. It's about not getting steamrolled by a system that's counting on you not knowing what to do next. From the Basement A story about FedEx's founder famously saving the company with a lucky night at a Vegas blackjack table becomes the day's trivia detour, and somehow ties neatly back into an episode all about refusing to give up when the system says no. Resources Mentioned The Healthcare Heist by Jordan Grumet, MD — Doc G's new book on fixing the doctor-patient relationshipEarn & Invest podcast — Doc G's award-winning personal finance podcast See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

  6. 5 Aug

    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.

  7. 3 Aug

    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.

  8. 31 July

    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.

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3.8
out of 5
25 Ratings

About

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

Information

  • Creator
    Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
  • Years Active
    2013 - 2026
  • Episodes
    1.5K
  • Rating
    Explicit
  • Copyright
    © SB Podcast LLC | Gamut Podcast Network
  • Show Website
    The Stacking Benjamins Show

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