BusinessInvestingEducation

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

Play

Open in

40 episodes
a few times a week
Avg 1 hr 4 min
English

Episodes 40

Newest Oldest Longest

All20 Unplayed20 In progress0 Played0

Counted on this page — what you have heard stays on this device, so it is not something the list can be paged by.

#1899
Friday · 1 hr 6 min
Should You Graduate From Index Funds to Individual Stocks? SB1899
You've done everything right. Emergency fund, employer match, maxed-out retirement account, boring diversified index funds quietly compounding in the background. And now some part of you is wondering: is there a next level? Financial educator Brian Feroldi joins Paula Pant and Jesse Cramer for a genuinely useful gut-check on whether picking individual stocks is a smart next step, a fun hobby, or a trap dressed up as ambition, and how to tell the difference before you put real money on the line. What You'll Walk Away With The single question that determines whether you're actually ready to buy individual stocks: do you have real interest in the process, not just the potential payoff Why working in an industry doesn't automatically make you qualified to invest in it The real statistics behind stock picking: roughly two-thirds of individual stocks underperform the market average Why losing money on your first few stock picks might be the best possible outcome, and why winning right away can be dangerous A clear framework for position sizing, so a stock-picking hobby never puts your actual financial plan at risk The real opportunity cost of stock picking as a "side hustle," and why it competes with your time as much as your money Why a great company and a great stock investment are often two completely different things Why This Matters Now There's a point in a lot of people's financial journeys where the basics start to feel almost too simple, and that itch to do something more advanced is worth taking seriously, not dismissing. But "more advanced" doesn't automatically mean "individual stocks," and jumping in without genuine interest or a clear framework can turn a healthy curiosity into an expensive mistake. Knowing honestly whether you're drawn to the actual process of researching and following businesses, not just the idea of beating the market, is the difference between a rewarding new hobby and a costly detour from a plan that was already working. From the Basement A tight, competitive trivia round on Bank of America's 1958 "Fresno Drop," the unsolicited mass credit card mailing that eventually led to the creation of Visa, shakes up the year-long standings in a genuinely dramatic way. Resources Mentioned Stock Simplifier — Brian Feroldi's AI-powered stock research tool Why Does The Stock Market Go Up? by Brian Feroldi — Brian's bestselling book on how the market works 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.
#1898
Wednesday · 1 hr 7 min
Lynda Gratton: What If You Live to 100? Here's How to Actually Plan For It SB1898
The traditional life plan, learn, work for four decades straight, retire once and for all, was built for a much shorter life than many of us are actually going to live. Lynda Gratton, London Business School professor and bestselling author of The 100-Year Life, has spent years studying what happens when that old blueprint stops matching reality. Her answer isn't a bigger retirement number. It's a completely different way of thinking about how work, rest, learning, and relationships fit together across a much longer stretch of time, and what that means for how you actually fund it. What You'll Walk Away With Why a single, long block of retirement often backfires, and what tends to happen to people's sense of purpose and friendships when it does The "weaving" framework: eight threads, four about staying productive and four about nurturing yourself, that Gratton argues need ongoing attention throughout life, not just at the end Why a "flexibility fund" might matter more than a traditional retirement account for anyone planning to take real breaks, sabbaticals, or career pivots along the way A simple four-option framework (stay, switch, scale back, or sail away) for deciding what to do when a chapter of work stops feeling right Why the fastest way to burn out is neglecting the "nurture" side of life, and why neglecting the "productivity" side leaves you financially fragile instead A genuinely useful reframe on AI: not a threat to outrun, but a reason to double down on the specifically human parts of work and life Why This Matters Now Longer lifespans sound like good news until you realize the traditional financial and career plan never accounted for them. A forty-year runway to retirement followed by thirty-plus years of doing nothing structured often turns out to be less fulfilling, and harder to fund, than a life built with more transitions built in along the way. Planning for that kind of life means thinking further ahead than most retirement calculators do, and building in the flexibility to actually use the extra years well, not just survive them. From the Basement A Dolly Parton headline turns into a genuinely sharp personal finance lesson: how she turned down Elvis, kept the rights to "I Will Always Love You," and built Dollywood, her literacy program, and her entire business empire on the exact same core talents rather than chasing unrelated ventures. Old-school diversification, but the boring kind that actually works. Resources Mentioned Living the 100-Year Life by Lynda Gratton — Lynda's book, workbook, and free diagnostic on the eight life threads Life Threads podcast — Lynda's eight-episode podcast series exploring each thread The 100-Year Life by Lynda Gratton and Andrew Scott — the original million-copy bestseller that started this line of research See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1897
Monday · 56 min
Can You Retire With $500,000? $750,000? A Million? SB1897
Someone with half a million dollars confidently retires and thrives. Someone else with a full million dollars runs into trouble within a few years. The dollar amount alone never tells the whole story, and today's episode proves it with three real scenarios side by side. Joe and OG walk through exactly what changes the math: your age, whether Social Security has kicked in yet, how much of your spending is already covered by guaranteed income, and how many years that portfolio actually needs to stretch. What You'll Walk Away With Why the question to start with isn't "how much do I have," it's "what's the gap between my expenses and my guaranteed income" A real comparison of three retirement scenarios (500k, 750k, and 1 million) that shows why the smallest portfolio can actually be the least risky Why the "safe withdrawal rate" debate among experts (ranging from under 4% to over 5%) matters less than having a plan for flexibility The often-overlooked lumpy expenses, property taxes, insurance premiums, home repairs, that can quietly wreck an otherwise solid retirement budget Why retiring early and taking Social Security ahead of schedule creates a double reduction that compounds for both you and a spouse A clear breakdown of how many years you actually have left to "practice" your retirement spending before you commit to it Why This Matters Now A specific dollar figure feels like it should provide an answer, but retirement security depends on the relationship between that number and your actual life: your fixed expenses, your guaranteed income, your timeline, and your flexibility if plans change. Two people with wildly different account balances can have equally solid plans, and two people with the same balance can be in completely different positions depending on when they start drawing from it. The real work isn't chasing a bigger number. It's understanding exactly what gap that number needs to fill. From the Basement A Social Security deep dive digs into a genuinely useful and underdiscussed detail: how retiring early doesn't just shrink your own benefit, it can shrink a spouse's spousal benefit too, and by how much. Plus, a Golden Girls trivia detour and a listener note that sparks a good, honest conversation about teaching kids to give. Resources Mentioned Stacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking tool SSA.gov — create an account to download your official Social Security earnings statement The 201 Newsletter — deeper dives on topics covered in the show See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1896
September 11 · 1 hr 1 min
Why "Doing It Yourself" With Money Is Costing You SB1896
Collaboration is celebrated everywhere else. Musicians collaborate. Athletes have training partners. Businesses merge their best ideas together. But mention teaming up on your finances, and suddenly it sounds suspicious, like you're doing something wrong. Joe sits down with Paula Pant, Jesse Cramer, and OG to ask why personal finance is the one area where going it alone gets treated as a virtue, and what exactly gets left on the table when nobody's allowed to help. What You'll Walk Away With Why financial blind spots are nearly impossible to see on your own, no matter how much you already know A real story about a stranger who handed over his entire real estate renovation system, no strings attached, simply because that's how a good community works Specific, practical answers for who to actually collaborate with on earning more, spending less, saving more, and investing better Why "the best collaborator" is sometimes the person most willing to tell you you're wrong A surprisingly effective incentive system for getting family members genuinely invested in cutting shared expenses Why competitors can make some of the most valuable collaborators of all, if you're willing to see them that way Why This Matters Now There's a quiet assumption in a lot of financial advice that asking for help is a sign of weakness, that a truly capable person should be able to figure it all out solo. But nobody expects a musician, an athlete, or a business to succeed in total isolation, and money isn't actually any different. The people who make the fastest progress usually aren't the ones with the most willpower. They're the ones surrounded by others willing to share a system, question an assumption, or simply say "that seems like a lot of money for fish." From the Basement A fiercely competitive year-long trivia race gets even tighter with a question about the Volkswagen Beetle's original 1949 price tag, complete with a brand-new (and delightfully cheap) trophy that finally dethrones the old one. Resources Mentioned Afford Anything podcast — Paula Pant's show, referenced episode featuring 9/11 survivor Michael Hingson Personal Finance for Long-Term Investors podcast — Jesse Cramer's show Stacking Benjamins on OG's calendar — for financial planning help See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1895
September 9 · 1 hr 17 min
Todd Havens: Why Most People Don't Have a Money Problem, They Have a Thinking Problem SB1895
Todd Havens spent decades dreaming of a net worth of zero, just breaking even felt like an impossible finish line. Then, in 2021, at the height of COVID, a doctor delivered news that would reframe everything: incurable blood cancer, tumors too numerous to count. What follows is one of the most honest, wide-ranging conversations this show has had about money, mortality, and the difference between being rich and actually being wealthy. Todd is now in remission, a self-made millionaire, and the author of a book built entirely around one idea: the biggest obstacle to financial security usually isn't a spreadsheet problem. It's what's happening between your ears. What You'll Walk Away With Why disability insurance and life insurance, the coverage nobody wants to pay for, turned out to matter more than almost anything else when the worst actually happened The "money dam" framework for deciding, moment by moment, what's actually worth spending on Why believing you "deserve" financial security might be the single most important money belief there is A game that separates helpful money beliefs from dangerous ones, and why "I'll save more when I make more" quietly sabotages people for years Why net worth, not salary, is the number that actually matters, and how that shift changed Todd's entire trajectory A genuinely difficult story about saying no to a parent's request for money, and why it was ultimately an act of love Why gratitude, generosity, and integrity are money topics, whether people realize it or not Why This Matters Now It's tempting to think financial struggle is purely a math problem: spend less, save more, invest wisely. But plenty of financially literate people still feel stuck, and the reason is rarely a lack of information. It's an old story about not deserving security, about money meaning lack, about identity getting tangled up with a bank balance. Untangling that story doesn't require a windfall or a perfect plan. It requires deciding, the way Todd did at forty, that today is the day the narrative changes, and then building simple systems that don't depend on willpower to keep working. From the Basement A headline on the four things you should never order in front of your boss turns into a genuinely useful (and very funny) etiquette lesson, complete with a real story about a twenty-year-old nephew calmly ordering the most expensive steak on the menu without blinking. A listener question on Robinhood also gets a thorough, unflinching answer on why the platform's marketing has repeatedly crossed lines other brokerages haven't. Resources Mentioned Think Wealthy by Todd Havens — Todd's book on the mindset behind financial freedom The Simple Path to Wealth by JL Collins — companion read referenced as the "systems" counterpart to Todd's "mindset" focus The Psychology of Money by Morgan Housel — referenced book on the behavioral side of money See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1894
September 7 · 1 hr 4 min
You're Doing Risk Tolerance Backwards SB1894
Every brokerage account asks the same question: how comfortable are you with a 20% decline? Are you conservative, moderate, or aggressive? Joe and OG argue that's exactly the wrong place to start, and it's why so many people panic-sell at the worst possible moment. The real question isn't how you feel about risk. It's what rate of return your actual goals require, and whether you can stomach the volatility that comes with getting there. Once you flip the order, risk tolerance stops being a personality quiz and becomes a math problem you can actually solve. What You'll Walk Away With Why "risk" and "volatility" are two completely different things, and confusing them leads to bad investing decisions The real order of operations for building a portfolio: goal first, required return second, risk tolerance last How standard deviation can turn scary market swings into something you expected all along, instead of something that panics you Why concentration risk quietly builds up in portfolios, even for people who think they're diversified A genuinely surprising take on why "getting more conservative as you age" often doesn't make sense, once you think in decades instead of birthdays Real answers to listener questions on emergency fund sizing, late-start Roth conversions, disability insurance coverage, and whether the 4% retirement rule still holds up Why This Matters Now A risk tolerance quiz can't tell you what you actually need your money to do. It just measures a feeling in the moment, and feelings change the second the market gets scary, which is exactly when a plan built on feelings falls apart. Building your investment strategy around your actual goals and time horizon, instead of a gut reaction to hypothetical losses, gives you something sturdier to hold onto when the inevitable rough year arrives. That's the difference between panic-selling at the bottom and staying the course long enough to actually reach the life you're investing for. From the Basement A Labor Day trivia detour into the 1916 origins of workers' compensation somehow spirals into a bit about an "employee named Al" being replaced by AI, which is either brilliant wordplay or a sign the basement crew needs a vacation. Possibly both. Resources Mentioned Stacking Benjamins Field Kit — the all-in-one budgeting and financial tracking tool Yell Down the Stairs — submit a question for a future OG and Anna episode See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1893
September 4 · 58 min
Angelo Poli: Why Your Health Is a Financial Decision (SB1893)
This is a different kind of episode. No trivia, no headlines, just Joe and longtime health and wellness expert Angelo Poli having an honest, unscripted conversation about what happened when a training injury, a missed diagnosis, and months of frustration sent Joe into a spiral he didn't see coming. It's a personal story, but the reason it belongs on a money show is simple: your ability to earn, think clearly, and actually enjoy what you've built depends on your health just as much as it depends on your portfolio. What You'll Walk Away With Why a setback in one area of your health or life can quietly spiral into others, and the exact moment that turnaround has to happen The science behind why doing "one thing" well beats trying to overhaul everything at once Why having someone else to be accountable to changes follow-through far more than willpower alone A candid explanation of why almost nobody follows through on "I'll think about it and get back to you," and what to do instead Why acting early in the day and early in the week measurably increases your odds of sticking with a health goal How physical health directly affects financial outcomes, through energy, focus, decision-making, and the years you get to actually enjoy what you've saved Why This Matters Now It's tempting to treat health and money as two completely separate categories of adulting. But the connection runs deeper than most people realize: poor sleep, low energy, and physical pain make it harder to think clearly, work efficiently, or make good financial decisions. And the whole point of building financial security is having the health to actually enjoy it, time with family, travel, the ability to do the things you're saving for. Taking care of one without the other only gets you halfway to the life you're actually working toward. Resources Mentioned MetPro — Angelo Poli's concierge nutrition, fitness, and lifestyle coaching program, free session for Stacking Benjamins listeners See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1892
September 2 · 1 hr 8 min
The 5 Secrets of a Happier Retirement with Wes Moss (SB1892)
What actually makes for a happy retirement? Today, Joe sits down with retirement expert Wes Moss, author of The Retire Sooner Method, to explore the research behind America’s happiest retirees. Wes explains why money is only part of the equation, how community and “super activities” give retirement purpose, why eliminating debt can create more freedom, and how a clear retirement plan can help reduce the fear of running out of money. Then Joe and OG tackle one of retirement’s most popular investing strategies: living off dividends so you never have to sell your investments. They break down why dividends feel so appealing, where the strategy can fall short, and why building your retirement income plan around your goals may matter more than chasing a particular yield. Plus, Doug celebrates the anniversary of the ATM with some cash-dispensing trivia. Resources mentioned Wes Moss The Retire Sooner Method: The 5 Secrets Behind America’s Happiest and Unhappiest Retirees You Can Retire Sooner Than You Think Retirees Love Dividends, but the Stock Market Surge Is Making Them Think Again — The Wall Street Journal Field Kit Finance The 201 newsletter — stackingbenjamins.com/201 Field Kit Finance webinars: Sign up for The 201 to get the full schedule. The Clark Howard Show FinCon Dana Anspach Ben Carlson Attorney Tim Semro’s recent Stacking Benjamins appearance FULL SHOW NOTES: https://www.stackingbenjamins.com/wes-moss-retire-sooner-method-1892/ Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1891
August 31 · 54 min
The Mental Trick That Makes Saving Money Effortless SB1891
Companies have gotten frighteningly good at removing friction from spending. One click, stored payment info, a box on your porch before you've even had time to regret the purchase. Today's episode flips that same idea around: what if you engineered your own financial life the same way, making good decisions the path of least resistance and bad decisions just annoying enough to make you pause? Joe and OG close out Financial Action Month with a genuinely useful framework for building systems that work even on the days your willpower doesn't show up. What You'll Walk Away With Why discipline isn't a personality trait, it's a system you build once instead of a decision you make every day A simple "make it easy or make it hard" test you can apply to any financial habit, from retirement savings to late-night online shopping Why automating your savings rate removes the single biggest source of decision fatigue in a financial plan A smarter way to handle windfalls and bonuses, deciding your split between saving, debt, and fun once a year instead of every single time Why canceling a subscription is deliberately made difficult, and the workaround that neutralizes it A four-step "financial action ladder" for turning financial knowledge into permanent, lasting habits Why waiting a day before a big purchase, and other small friction points, can save you from regret without requiring any extra willpower Why This Matters Now Knowing what to do with your money has never really been the hard part. The hard part is doing it consistently, especially when life gets busy, stressful, or just plain boring. Building your environment so the smart choice is also the easy choice takes the daily grind of willpower out of the equation entirely. That's not a lack of discipline, it's actually the most disciplined move available: deciding once, automating it, and letting the system do the work every day after that. From the Basement A goofy but genuinely fun "make it easy or make it hard" game plays out across everything from emergency funds to concert tickets, and a National Trail Mix Day detour delivers exactly the kind of nonsense only this show could make delightful. Resources Mentioned Stacko Financial Action Month board — the interactive game with a money move for each square Stacking Benjamins Field Kit — the all-in-one financial organization and subscription-canceling tool Profit First by Mike Michalowicz — the book referenced on flipping the save-then-spend default See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1890
August 28 · 45 min
How Many of These Ad Slogans Can You Still Name? (Paula Pant, Len Penzo, OG Play Along) SB1890
Everybody likes to believe they're too smart for marketing. Companies spend billions of dollars putting jingles and slogans in our heads anyway, and this episode puts that theory to the test. Paula Pant, Len Penzo, and OG face off in a rapid-fire game: Doug reads a slightly modified version of a famous advertising slogan, and they have to name the brand. What follows is a genuinely fun, surprisingly competitive round that proves just how deep this stuff sits in all of our brains, whether we like it or not. This one's a Greatest Hits favorite, originally recorded back in 2020, and the game holds up exactly as well today. What You'll Walk Away With A fast-paced, genuinely fun game you can replay in your own head (or with friends on a road trip) testing how many classic slogans you actually remember A real discussion on how much advertising quietly shapes what we believe is smart to buy, invest in, or trust with our money A candid conversation about pieces of financial advice that used to be gospel and don't hold up anymore, including homeownership as an automatic wealth-builder and the old "100,000 miles and it's time for a new car" rule A memorable real-world story about how deeply brand loyalty can override even a clearly better financial decision A reminder that good financial advice isn't about memorizing fixed rules, it's about regularly checking whether those rules still fit your actual life Why This Matters Now It's easy to assume you make financial decisions purely on logic. But brand recognition, catchy slogans, and decades of repeated marketing messages shape more of our buying and money decisions than most of us would like to admit. Recognizing that influence doesn't mean living in constant suspicion of every ad you see. It means occasionally asking whether a belief about money, homeownership, cars, insurance, college, is something you actually decided, or something you absorbed because you heard it enough times to assume it was true. From the Basement A wildly competitive slogan showdown ends with a last-to-first comeback, plus a genuinely great story about a five-year-old spotting a McDonald's from the top of the Empire State Building at the exact wrong (or right) moment. Resources Mentioned Afford Anything podcast — Paula Pant's show LenPenzo.com — Len Penzo's site, including his sister blog, The Persistent Itch Stacking Benjamins Field Kit — the all-in-one financial organization tool referenced in the updated intro See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#1889
August 26 · 1 hr 10 min
Mel Robbins: The Morning Habit That Rewires Your Brain SB1889
Before Mel Robbins became one of the most recognized names in personal development, she was $800,000 in debt, unemployed, and numbing the panic with bourbon most nights by six o'clock. She knew exactly what she needed to do to climb out. Knowing wasn't the problem. Taking the first step was. That gap, between knowing and doing, is exactly what this conversation is about, and it's why Mel's simplest tool, a five-second countdown and a high five in the mirror, has been validated by neuroscience, adopted by veterans' organizations treating PTSD, and linked to real behavior change in ways that go well beyond feel-good advice. This episode originally aired in 2021 and earned its spot in our Greatest Hits lineup because the core idea hasn't aged a day. What You'll Walk Away With The five-second rule Mel used to physically interrupt anxiety and get out of bed during her lowest financial point Why knowing what to do with your money is almost never the real obstacle, and what actually is The surprising research linking high-fives among NBA teams to which teams went on to win championships Why so many people feel resistance instead of relief the first time they try this exercise, and what that resistance is actually telling you The neuroscience behind why a simple physical gesture can interrupt a negative thought spiral more effectively than positive self-talk Why self-worth tied to a bank balance, a job title, or a number on a scale tends to collapse the moment things go wrong A genuinely surprising story about grief, intuition, and a decision that changed the direction of Mel's entire family Why This Matters Now You probably already know several things you should be doing with your money right now. That's rarely the hard part. The hard part is closing the gap between knowing and doing, especially in moments of stress, shame, or overwhelm, exactly the moments financial setbacks tend to create. Building a habit of small, immediate self-support, showing up for yourself before you've accomplished anything, turns out to be one of the most overlooked tools for actually following through on the financial changes you already know you need to make. From the Basement A headline segment on modern, lower-fee annuities gets a healthy dose of skepticism, and a TikTok "wealth hack" involving margin loans gets thoroughly, hilariously debunked, a good reminder that not everything that sounds clever on social media survives contact with how markets actually work. Resources Mentioned The High 5 Habit by Mel Robbins — Mel's book on the science-backed daily practice Stacking Benjamins Field Kit — the all-in-one financial organization tool referenced in the updated intro See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
#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.

Showing 1–20 of 40 episodes