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The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

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

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#1888
August 24 · 1 hr 4 min
Your Financial Order of Operations: What to Fix First SB1888
There's a version of financial advice that lists fifty things you're supposed to be doing at once: build an emergency fund, pay off debt, invest, get life insurance, start a Roth, build an estate plan. All true, all important, and all completely useless without one missing piece: the order. Joe and OG walk through the exact sequence for figuring out what to tackle first, second, and third, so instead of freezing under the weight of everything, you know precisely where to start today. This one's a Stacking Benjamins classic, originally recorded a few years back, and the framework holds up so well it earned a spot in our Greatest Hits lineup unchanged. What You'll Walk Away With A simple four-quadrant framework for seeing your entire financial picture in one place, instead of overwhelming yourself with fifty scattered tasks Why cash flow and risk management should almost always come before any long-term goal-setting, no matter how exciting the goals are The real difference between a strict budget and an "anti-budget," and how to know which one your situation actually calls for Why debt consolidation can quietly make things worse if the underlying behavior never changes A clear-eyed look at which insurance actually matters most early in your financial life, and which ones get overhyped Why starting with your tax strategy or investment picks first is almost always backwards, and what should come before it The blunt case against co-signing a loan for a family member, no matter how good the reason sounds Why This Matters Now The instinct to fix everything at once usually backfires, not because the individual advice is wrong, but because doing five things halfway rarely beats doing one thing completely. A clear order of operations replaces that scattered, everything-at-once anxiety with a simple next step, and that clarity alone tends to build more momentum than any single tactic. Whether you're just starting to get organized or you've been meaning to revisit your plan for a while, knowing what actually comes first changes everything that follows. From the Basement A TikTok "hack" involving sneaking into a hotel breakfast buffet to save on groceries becomes the day's cautionary tale, alongside a genuinely unhinged story about an office keg that taught an entire WeWork floor a hard lesson about unlimited free beer. Resources Mentioned Stacking Benjamins Field Kit — the all-in-one net worth and budgeting tool referenced in the updated intro The 201 Newsletter — deeper dives on topics covered in the show, written by Kevin Bailey See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1887
August 21 · 1 hr 13 min
What to Teach Your Kids About Money, and When 1887
Every parent eventually asks the same question: what does my kid actually need to know about money, and when do I teach it? Today's roundtable brings together three genuinely different perspectives, financial educator Karen Holland of Gifting Sense, middle school teacher and author Alaina Trivax, and Rishi Vamdatt, the now-college-bound creator behind Easy Peasy Finance who started teaching kids about money at age eight. Together they build a real, age-by-age roadmap, from swiping a credit card at six years old to filing taxes for the first time at eighteen. What You'll Walk Away With Why waiting until kids are "old enough to understand the math" is one of the most common mistakes parents make A simple age-by-age breakdown of what to teach, from age six all the way through eighteen Whether you should tell your kids exactly how much you earn, and what to say instead if you'd rather not Why letting kids make small, affordable money mistakes now protects them from much bigger ones later How to talk to kids about in-game currencies and microtransactions in a way that actually sticks A refreshingly simple way to build an allowance system that teaches real financial judgment, not just chore compliance Why you don't need to be great with money yourself to teach your kids well, and what actually matters more than expertise Why This Matters Now It's easy to feel unqualified to teach your kids about money, especially if your own financial journey has had plenty of stumbles. But the goal was never to have all the answers. It's to normalize talking about money at home, model good decision-making out loud, and let kids practice with small stakes before the stakes get real. A little structure around when to introduce which concepts takes the guesswork out of a subject most parents already feel behind on, and turns it into something manageable, even fun. From the Basement A special exhibition round of trivia brings together three guest contestants for a genuinely close guessing game on the current going rate from the Tooth Fairy, complete with inflation commentary that would make any economist proud. Resources Mentioned Follow the Money by Alaina Trivax — Alaina's new activity-based book teaching kids about money Let's Make It Grow — Alaina's platform helping parents teach financial literacy Gifting Sense — Karen Holland's nonprofit teaching kids mindful spending, including the "Spending Ed" program Easy Peasy Finance — Rishi Vamdatt's YouTube channel and book series, including the new release Easy Peasy Stocks See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1886
August 19 · 54 min
Tim Semro Answers Your Weirdest Estate Planning Questions SB1886
"Do I need a trust or just a will?" might be the single most common estate planning question there is, and estate attorney Tim Semro says most people are asking it backwards. The real question isn't trust versus will, it's how do you avoid probate, and a trust is just one of several ways to get there. Tim returns to answer a full mailbag of real Stacker questions, covering everything from a $200,000 mistake buried in a lady bird deed to the exact reason so many families accidentally disqualify a parent from Medicaid. What You'll Walk Away With Why "trust versus will" is the wrong question, and the three-column framework that actually determines what you need What a lady bird deed is, when it makes sense, and the family conflict it can quietly set up down the road The tax detail buried in gifting property early that can cost your heirs tens of thousands of dollars they didn't expect Why naming a power of attorney without having an honest conversation first is one of the most common and costly mistakes families make The five-year Medicaid look-back rule explained clearly, including what happens if you don't quite make it to five years How debt actually works after someone dies, including a real statute of limitations window most people don't know exists A special needs trust structuring tip that can protect a family member's government benefits without giving up their inheritance Why This Matters Now Estate planning tends to get pushed to "someday" because it feels complicated, uncomfortable, or like it only matters once you're wealthy. But the actual decisions, who has power of attorney, how property transfers, what happens if a parent needs long-term care, apply to nearly every family, regardless of net worth. Getting the structure right isn't about predicting the future perfectly. It's about making sure the people you love aren't left guessing, fighting, or losing money to easily avoidable mistakes during an already difficult time. From the Basement A birthday trivia detour into the surprising origin of the Nobel Prize reveals it was born from a very specific kind of reputation crisis, proof that it's never too late to actively shape how you'll be remembered. Resources Mentioned Your Money, Your Way by Tim Semro — Tim's book on estate planning, free to download Semro Henry Ltd. — Tim's estate planning law firm Stacking Benjamins Field Kit — the all-in-one financial organization tool See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1885
August 17 · 1 hr 14 min
The Four Psychological Tricks That Get You to Sign Anything (SB1885)
Nobody skips reading a contract because they're careless. Contract attorney Leo Mann spent 30 years writing the fine print that governs leases, car loans, job offers, and gym memberships, and he says the reason smart people sign blind isn't laziness at all. It's four specific psychological pressures, engineered on purpose, stacked on top of each other in the exact moment you're handed the paperwork. Today he walks through exactly how those tricks work, and more importantly, how to spot them before you sign away something you'll regret. What You'll Walk Away With The four psychological traps, stacked together on purpose, that get otherwise careful people to sign without reading Why the phrase "this is standard" should be one of the biggest red flags in any negotiation A green flag, yellow flag, red flag rundown of common contract moments, from blank spaces to rush deadlines to page-by-page initials The hidden clause in shared leases that can leave one person legally responsible for an entire group's unpaid rent Why the number on the front page of a lease or job offer is often just marketing, and where the real total actually lives The critical difference between an employment offer letter and the actual employment agreement, and why only one of them is legally binding Why severance is almost always more negotiable than employers make it seem, and the two questions worth asking about any financial product before you commit Why This Matters Now Every adult signs dozens of contracts over a lifetime, apartment leases, car loans, job offers, gym memberships, and the fine print in most of them is written to be skimmed, not read. That's not an accident, and it's not really about intelligence or diligence either. It's about recognizing the exact moments you're being nudged to move fast, and knowing which few sentences in a stack of paperwork actually matter. A little contract literacy doesn't just protect your money, it gives you real leverage the next time someone slides a stack of paper across the table and says, "just sign here." From the Basement A headline about Pepsi's infamous 1996 fighter jet promotion becomes the day's trivia detour, proving that even the biggest brands occasionally get burned by their own fine print, right alongside the rest of us. Resources Mentioned Don't Sign That by Leo Mann — Leo's #1 bestselling guide to consumer contracts The Contract Literacy Movement — Leo's initiative teaching everyday people to read what they sign Stacking Benjamins Field Kit — the all-in-one budgeting, credit monitoring, and financial tracking tool Stacko Financial Action Month board — the interactive game with a money move for each square See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1884
August 14 · 1 hr 3 min
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 perfectionism Why budgeting "until it hurts" can quietly damage your relationship with money more than it helps The 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 it A reframe on "one more year" retirement thinking that flips the entire question around Why letting kids make small, reversible money mistakes teaches more than any lecture ever could The surprising overlap between "still researching the best option" and simply avoiding a decision Why the biggest lever in your investment returns has almost nothing to do with picking the "best" individual stock Why 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 program Personal 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 Boston 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.
#1883
August 12 · 1 hr 1 min
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 expect The strange, long-running correlation between bologna sales and economic recessions Simple substitutions, buying whole meats and block cheese instead of pre-sliced, that can meaningfully cut your grocery bill Why "nominally the highest price ever" doesn't always mean "the most expensive it's ever really been," once you adjust for inflation How a single signed power of attorney document led to nearly $1 million disappearing from a vulnerable parent's accounts The real difference between what your estate plan says and what your actual account beneficiary designations say, and why that gap can undo your entire plan A billionaire's surprisingly simple family money ritual that keeps inheritance conflicts from tearing families apart Why 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 history How Kenn Ricci Runs Family Wealth Meetings — the Wall Street Journal piece on transparent family net worth meetings, referenced in the discussion Stacking 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.
#1882
August 10 · 55 min
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 anyway The real difference between an actively managed fund and a passive one, and why "active" isn't automatically a red flag A little-known 401k feature that can give you far more investment control without giving up your match How to think through a Roth conversion when your income, your future tax bracket, and even the state you'll retire in are all still unknown The single mistake that quietly wastes a Roth contribution opportunity for good, since you can never get that calendar year back What an ABLE account is, and how it's different from a 529 in a way that matters enormously for a family navigating a new diagnosis Why 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 meeting Why 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 tool Stacko Financial Action Month board — the interactive game with a money move for each square Three Money Buckets video — Stacking Benjamins' YouTube Financial Basics course Yell 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.
#1881
August 7 · 58 min
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 career A simple "stay, fix it, or go" framework for evaluating your specific work situation, tested against real scenarios Why waiting for the "right time" to leave a toxic job often means waiting far too long The financial prep work worth doing now, even if your job is fine today, so you're ready to move fast if it isn't tomorrow Why your skills and confidence can quietly atrophy under a bad boss, even if your paycheck stays the same How to separate your relationships with great coworkers from your relationship with a bad workplace A practical first-week plan for anyone who gets laid off or walks away suddenly, starting with what actually needs to be true immediately Why 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 freedom Building Your Money Machine podcast — Mel's weekly show on wealth-building and financial freedom Afford 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.
#1880
August 6 · 1 hr 14 min
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 realize Why a procedure can get pre-approved and still get denied months later, and what to save to protect yourself A simple "who do you call first" framework for untangling a prescription, billing, or coverage problem The pharmaceutical industry trick of repackaging old drugs as "new" ones, and the one question that sidesteps it completely How to spot whether your doctor's office is privately owned or backed by private equity, and why it changes the care you get Why so much unnecessary testing exists purely to protect doctors from lawsuits, not to protect you The real math on insurance appeals, and why giving up is exactly what the system is counting on Why 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 relationship Earn & 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.
#1879
August 5 · 1 hr 4 min
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 instead The five categories every dollar actually falls into, and why skipping even one of them creates financial blind spots Why future income should never be allowed to rescue your current plan, and how that habit quietly leads to credit card debt A surprisingly simple system for making irregular bills stop feeling like emergencies The 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 money Why money worry doesn't disappear once you have more of it, and what actually makes it go away Why 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 spending YNAB (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.
#1878
August 3 · 51 min
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 year The four numbers you actually need to know to build your own mini tax forecast in one sitting How the IRS "safe harbor" rule works, and the two different percentage thresholds that keep you penalty-free A common myth about side hustle income that trips up more people than you'd expect Why switching to a Roth 401k without a plan can quietly blow a hole in your monthly cash flow The real math behind donor-advised funds, and why writing a check to charity may be leaving money on the table A simple gut-check for figuring out whether you need a professional or can handle a financial fix yourself Why 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 review Stacko Financial Action Month board — the interactive game with a money move for each day Field Kit Finance — track net worth, spending, and subscriptions in one place Daffy — donor-advised fund platform referenced for charitable giving strategy IRS 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.
#1877
July 31 · 1 hr 4 min
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 true The surprising reason financially literate people still make emotional money mistakes, according to research on an unrelated profession A simple writing exercise that makes you far more likely to stick to your own financial plan Why betting on what's familiar, your employer's stock, your home country's market, is quietly one of the riskiest things you can do A martial-arts-inspired mental trick for turning your own biases into tools instead of traps The real reason "this time is different" almost always feels true and is almost always the wrong conclusion to act on Why 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 preorder Afford Anything podcast — Paula Pant's show Personal 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.
#1876
July 30 · 54 min
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 today The 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 community Why this isn't 2008 -- and the one important way it's actually worse than what the mortgage crisis taught us Why one in seven homeowners now carries no insurance at all -- and what that means for the next major weather event The 100-year flood problem: why homes built to withstand a once-in-a-century event are now getting hit every five to ten years What 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 rate How 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 doubled OG'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 had Why 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 resolved The risk management reframe: why thinking about insurance is the wrong starting point, and what to think about instead Why 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.com Black-Litterman Model -- referenced for Bob Litterman's background in risk pricing Climate Central -- tracks billion-dollar weather events annually; climatecentral.org National 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.
#1875
July 29 · 1 hr 11 min
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 from The surprisingly personal origin story behind Fidelity's founder, and the market-crash lesson that shaped the entire company's philosophy Why Fidelity almost missed the money market fund revolution, and the workaround that changed how everyday people access their cash The near-sale that almost happened in 2005, and how close the company came to becoming something completely different Why checking your 401k balance more often might actually be good for your financial decision-making, according to Fidelity's own research How a family succession battle nearly pushed the current CEO out of the business entirely A useful mental gut-check for figuring out how much of your "checking account cushion" should actually count as part of your emergency fund Why 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 history Field 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.
#1874
July 28 · 1 hr 9 min
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 life A simple, low-stakes way to start a money conversation with a partner who's checked out, without triggering defensiveness Why financial advisors dread meeting a client's "uninvolved" spouse for the first time after a death What actually happens to your financial life if your money-handling spouse suddenly can't do it anymore How financial stress physically changes your body, according to a major new health study Why the standard advice to "just put more in your 401k" completely misses people who are financially struggling right now The surprising first place financial counselors suggest looking before you take out any kind of loan A behind-the-scenes look at how employers are (and aren't) using workplace benefits to actually help people Why 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 Talercio Jill 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 episode Brightside Financial Care — Kristy Talorico's company, financial care benefits for employers Findhelp.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.
#1873
July 27 · 56 min
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 67 The real reason waiting until 70 pays off, and why it has almost nothing to do with growth A subtle, surprisingly common mistake that can quietly wreck a smart claiming strategy years after you made it What actually happens to your benefit if your spouse passes away first, and how remarriage timing can change everything Why the industries where workers never pay into Social Security create a completely different retirement math The dollar threshold that can force you to pay back benefits you already claimed A 2024 rule change that may directly affect certain public employees and hasn't gotten nearly enough attention Why raising the retirement age matters a lot less than people assume, depending on how you actually want to retire How a totally different tax, the Medicare surcharge, quietly rides along with your Social Security decisions A quick true-or-false round that separates Social Security fact from the myths everyone repeats Why 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 deadline Create your SSA.gov account — check your earnings history and benefit estimate id.me login for SSA.gov — the identity verification step for your Social Security account The Walt Disney Company: Walt's Era — Acquired podcast — the four-hour deep dive Doug referenced on Disney, Oswald the Rabbit, and protecting your name Stacking 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.
#1872
July 24 · 1 hr 10 min
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 entirely Jesse'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 know OG'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 half The 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 eliminate Safe, 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 machine Why learning the AI tools right now -- even if you're 58 and four years from retirement -- is the modern equivalent of learning email in 1993 JL Collins' line that applies to careers just as much as portfolios: flexibility is the only true security Should 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 expect Why 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 ready The 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 researcher Tony Robbins interview with Ray Kurzweil -- referenced for additional AI perspective; linked at stackingbenjamins.com Afford Anything episode 693 -- Paula Pant interview with Dr. Ben Zweig on AI and the workforce; affordanything.com/episode693 Personal Finance for Long-Term Investors (PFLTI) -- Jesse Cramer; upcoming AMA episode 19 and episode 150 personal AMA Anthropic Skill Jar -- free AI training; referenced by Paula for learning Claude features Delivering Happiness by Tony Hsieh -- referenced for the Zappos customer service model OG financial planning calendar -- stackingbenjamins.com/og Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201 Stacking 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.
#1871
July 22 · 1 hr 11 min
Ryan Hawk on How Ordinary People Become Exceptional (And the Actions That Actually Compound) SB1871
Ryan Hawk arrived at Miami University the day after high school graduation, with a plan to earn the starting quarterback job and make it to the NFL. Two years later, a 6'5" kid from somewhere in Ohio showed up and took the job away from him. That kid turned out to be Ben Roethlisberger. What Ryan did with that moment became the entire foundation of The Learning Leader podcast, one of the most respected leadership shows in the country, and his new book The Price of Becoming. He joins Joe and OG to talk about the habits, frameworks, and daily actions that compound into something exceptional -- and what to do when the plan doesn't survive contact with reality. What You'll Walk Away With Coach Hepp's three-sentence leadership philosophy that Ryan has never forgotten: have a plan, work the plan, and plan for the unexpected Why being told "he gives us a better chance to win than you do" was the most valuable coaching Ryan ever received -- and what it teaches about adding value versus wanting credit The imitate-then-innovate framework: why The Beatles were a cover band first, why Wayne Gretzky took handwritten notes watching players smaller than himself, and why copying the greats isn't theft -- it's the fastest path to finding your own voice Ryan's first draft pick for becoming exceptional: a five-to-ten minute nightly prompt exercise built around one Charlie Munger question that compounds like a great investment Why truth tellers -- people willing to look you in the eye and tell you what you need to hear rather than what you want to hear -- are the most underrated asset in any high performer's life The superpower Ryan has found in every great leader he's interviewed across 11 years and hundreds of conversations: deep, specific curiosity -- and why it's the ultimate form of showing love Sweat more than you watch other people sweat: Scott Galloway's physical discipline framework applied to every area of life The Brock Purdy late-round pick: why bringing a notebook to every meeting -- something almost no intern or young employee does -- is the single easiest way to stand out and learn faster The boomerang kids debate: why nearly half of Americans under 30 now live with a parent, when OG thinks it's a great idea, when he thinks you suck, and why it only works if there's a real plan with a real end date James from the community: how retiring at 52 let him become his daughter's bank in a hot real estate market -- loan document, market rate, free labor but zero say in the house Why This Matters Now The gap between people who become exceptional and people who almost do isn't talent -- it's the daily actions they're willing to stack. This episode is the practical blueprint for what those actions actually look like. From the Basement Ryan Hawk joins Joe and OG to talk about getting benched, the imitate-then-innovate path from cover band to original voice, and the five draft picks that build a great life -- including one that Joe immediately connects to hiding money from himself. The Wall Street Journal's piece on boomerang kids gives OG a platform to explain exactly when it's smart, when it's lazy, and why his kids should not take this as an invitation. Doug arrives with Cleveland trivia and the story of how a newspaper's cheap typesetting permanently changed the name of a major American city. James from the community sends a letter that makes OG quietly admit he was wrong about the appraisal. Resources Mentioned The Price of Becoming: The Compounding Practices of High Performance by Ryan Hawk -- available wherever books are sold The Learning Leader podcast -- Ryan Hawk; available wherever you listen to podcasts; learningleader.com Steal Like an Artist by Austin Kleon -- referenced for the imitate-then-innovate framework Set for Life by Scott Trench -- referenced for Joe's kids; biggerpockets.com Broke Millennial by Erin Lowry -- referenced for Joe's kids; brokemillennial.com Wall Street Journal -- "Living With Your Parents Is No Longer Viewed as a Failure to Launch" by Rebecca Picciotto and Nicholas G. Miller Stacking Benjamins Field Kit -- stackingbenjamins.com/fieldkit Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201 Stacking 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.
#1870
July 20 · 1 hr 14 min
How to Get More Free Money From Your 401k (The Moves Most People Never Make) SB1870
An alarming number of people have access to a 401(k) and are either not using it, not getting the full employer match, or not making the simple moves that turn a good account into a great one. Joe and OG dedicate a full episode to the retirement account that most people take for granted -- covering contributions, matching, investment selection, Roth versus traditional, and the specific decisions that separate people who retire comfortably from people who almost got there. Plus wins from the Stacker community and trivia that will make you the most dangerous person at your next dinner party. What You'll Walk Away With Why the employer match is the single highest guaranteed return available to any investor -- and the specific contribution level that captures every dollar of it Roth 401(k) versus traditional 401(k): the one question that cuts through all the noise and tells you which one to use right now Why your investment menu feels overwhelming and how to make a great choice in under five minutes using one simple filter The auto-escalation feature most people never turn on -- and why setting it up once can add tens of thousands of dollars to your balance without you doing anything else What to do with your 401(k) when you leave a job: the four options, which one is almost always wrong, and which one most people choose anyway Why contribution limits are higher than most people think -- and the catch-up contribution that becomes available at 50 that most people in their 40s don't know to plan for The vesting schedule trap: why your employer match might not actually be yours yet -- and what that means for anyone thinking about leaving their job Why 403(b) and 457 plans follow most of the same rules -- and the one unique advantage the 457 has that almost nobody knows about OG on the single most common 401(k) mistake he sees in client portfolios -- and how long it typically takes to fix Stacker wins from the community: the specific moves people made this month that are already paying off Why This Matters Now Every year you don't optimize your 401(k) is a year of compounding you don't get back. The moves in this episode are not complicated -- but most people either don't know about them or keep putting them off. This is the episode to send to anyone who has a 401(k) and has never really looked at it. From the Basement Joe and OG celebrate the 401(k) in mom's basement while OG recovers from completing the Triple Bypass -- a Colorado cycling event that covers three mountain passes and approximately all of the elevation gain in the western hemisphere. OG's wife asked if he'd do it again. He answered with a childbirth analogy. Doug arrives with trivia that will be re-shared all week. The community delivers wins that prove the system works. Resources Mentioned Stacking Benjamins Basics Guide -- stackingbenjamins.com/basicsguide Stacking Benjamins Field Kit -- stackingbenjamins.com/fieldkit Stacking Benjamins BAD Groups -- stackingbenjamins.com/bad Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201 OG financial planning calendar -- stackingbenjamins.com/og Stacking 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.
#1869
July 17 · 1 hr 11 min
Who Should You Trust With Your Money? (Friends, Family, Experts, AI, and Bad Advice) SB1869
A Wall Street Journal story about a 17-year-old helping his family with financial decisions kicks off a much bigger Stacking Benjamins question: who should you actually trust with your money? Joe, Doug, Paula Pant, Jesse Cramer, and special guest Roger Whitney dig into where great advice comes from, why bad advice often comes from people who love you, and how to build a better filter before you act. Along the way, they talk books, podcasts, family advice, AI, confirmation bias, homebuying myths, index funds, retirement plans, and why "smart" isn't enough. What You'll Walk Away With Why Roger says "advice" has a high bar: real advice should apply to your specific life, not just sound smart in public The difference between information and advice -- and why confusing the two can lead you into trouble Why books often beat random internet advice: they usually have more vetting, structure, and accountability How well-meaning friends and family can still give terrible money advice when they speak confidently about things they don't really understand Paula's advice pyramid: avoid people who profit from outrage, be skeptical of people with no accountability, and seek sources with both expertise and vetting Why AI can be useful as a sparring partner, but not as a substitute for your own thinking or fact-checking The danger of "always" and "never" advice: always buy a house, always max your 401(k), never finance a car, always buy index funds Why renting isn't automatically throwing money away -- and how the price-to-rent ratio can help you think more clearly Why maxing out your workplace retirement plan may not always be the right move, especially when tax flexibility, business investment, or other goals matter more How confirmation bias, present bias, and absolute certainty can fool you into believing your plan is stronger than it is What to look for in your personal board of directors: people you respect, people with a high signal-to-noise ratio, and people who are kind enough to tell you the truth Why Roger says a kind person is better than a merely nice one when you need real feedback Why This Matters Now Financial advice is everywhere: podcasts, books, TikTok, AI, coworkers, relatives, advisors, and confident strangers with strong opinions. The hard part isn't finding advice. It's knowing which advice deserves your attention. This episode gives Stackers a filter for separating useful guidance from noise before the wrong voice gets too close to their money. From the Basement Joe uses a Wall Street Journal piece about a teenage family financial advisor to launch a bigger card-table debate with Paula Pant, Jesse Cramer, and Roger Whitney. The crew builds a money-advice pyramid, debates which financial rules should be ignored, and explores when to trust yourself versus when to bring in your board of directors. Doug celebrates Art Linkletter with Game of Life trivia, Paula admits she's never played it, and OG's trivia lead might get a little more uncomfortable. Resources Mentioned The Wall Street Journal piece by Oyin Adedoyin about a 17-year-old helping his family with financial decisions Roger Whitney -- The Retirement Answer Man podcast Paula Pant -- Afford Anything podcast Jesse Cramer -- Personal Finance for Long-Term Investors podcast Seth Godin -- Linchpin Thomas Stanley and William Danko -- The Millionaire Next Door Robert Kiyosaki -- Rich Dad Poor Dad Robert Cialdini -- Influence Richard Feynman -- Surely You're Joking, Mr. Feynman! Beth Kobliner -- referenced as an upcoming Afford Anything guest Stacking Benjamins Newsletter, The 201 -- stackingbenjamins.com/201 Stacking Benjamins YouTube channel -- youtube.com/stackingbenjamins 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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