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The Stacking Benjamins Show: Daily Summaries Delivered
by 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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- 2 days ago55 min
Money Ideas That Sound Great Until You Read the Fine Print (SB1905)
Bigger returns. Guaranteed income for life. Retiring five years early. Every one of these sounds like an obvious yes, until you see the invoice that comes with it. Joe puts Doc G, OG, and Jesse Cramer through a rapid-fire "in or out" game: he pitches five genuinely appealing financial ideas, and each of them has to decide whether they'd actually take the deal, and name the worst realistic thing that could go wrong if they did.What You'll Walk Away WithWhy leveraged ETFs have historically wiped out the vast majority of investors who hold them for more than a few yearsThe real, academically-supported case for and against thematic and "beat the market" investment fundsA clear framework for handling a single stock that's grown into 40% of your portfolio, including a simple trick for spreading a big tax bill across two tax yearsWhy "guaranteed income for life" almost always means giving up the one thing that actually protects you from inflation over a multi-decade retirementA genuinely helpful explanation of what a Monte Carlo simulation's "80% success rate" actually means, and why it's not the cliff-edge failure people assumeWhy retiring five years earlier isn't automatically the right move, even when the math technically worksA real cost-benefit gut check on working an extra year or two specifically to fully fund a child's college educationWhy This Matters NowThe financial products and strategies that sound the most appealing, guaranteed income, market-beating returns, an earlier retirement, all have a cost that isn't obvious from the pitch alone. That cost isn't always dishonest or hidden on purpose, but it only becomes clear once you ask the right follow-up questions. Learning to instinctively look for that fine print, what you're giving up, what could go wrong, and whether the tradeoff actually serves your specific goals, is a far more useful skill than knowing the name of any single financial product.From the BasementA three-way tie atomizes the year-long trivia standings heading into the fourth quarter, decided by a question about how little Charles Schulz was paid for the very first month of Peanuts comic strips.Resources MentionedEarn & Invest podcast — Doc G's showPersonal Finance for Long-Term Investors podcast — Jesse Cramer's showGranola — AI-powered meeting notes tool mentioned in the sponsor breakStacking Benjamins on OG's calendar — for financial planning helpSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 4 days ago58 min
Don't Tell the Car Dealer Your Budget (And Other Money Moves That Actually Work) SB1904
A $12,000 emergency room bill for popping a dislocated shoulder back into place. A car-buying strategy that saved one family $4,000 with a single text message. A college athlete's first taste of NIL money and the tax questions that come with it. Joe and OG spend today answering real questions from real Stackers, the kind of specific, practical situations that don't always fit neatly into a textbook, but come up constantly in real life.What You'll Walk Away WithWhy you should never tell a car dealer your monthly budget, and the exact three-rule negotiation process that saved one family thousandsA real, word-for-word example of how to negotiate a hospital bill down, including the specific questions that actually get resultsWhat to know before buying stock in a private, employee-owned company, including the questions to ask about liquidity and getting your money back outWhy a college athlete earning NIL revenue-sharing income needs a specialized tax professional, not a generic preparerThe real difference between qualified and ordinary dividends, and why it matters less than most investors assumeA nonprofit resource that helped one young Stacker eliminate a $43,000 hospital bill entirelyWhy asset location (which accounts hold which investments) only matters once your portfolio is diversified enough across account types to make a differenceWhy This Matters NowFinancial advice often gets taught in tidy, general categories, but real financial life shows up as messy, specific situations: an ER bill with no clear price tag, a car dealer who won't budge on your trade-in, a new source of income nobody prepared you for. Having a framework for these moments, knowing what questions to ask, who to loop in, and where the leverage actually sits, turns a stressful surprise into a solvable problem. None of these situations require perfect expertise, just knowing enough to ask the right question at the right moment.From the BasementA Good Neighbor Day detour uncovers the legendary origin of the first-ever Stacking Benjamins meetup: a group of miners in Healy, Alaska, who listened to the show while at work and reached out when they heard Joe was headed to Denali.Resources MentionedStacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking toolDollar For — nonprofit that helps eliminate medical debt for qualifying patientsSB1808: How She Eliminated a $43,000 Hospital Bill — referenced episode on medical debt reliefSB1899: Should You Graduate From Index Funds to Individual Stocks? — referenced episode with Brian FeroldiYell Down the Stairs — submit a question for a future episodeFULL SHOW NOTES: https://www.stackingbenjamins.com/money-rules-worth-questioning-1904/Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 6 days ago59 min
Our Top 5 Esoteric Money Strategies That Work (For the Right Person) SB1903
Some financial strategies aren't bad, they're just wildly oversold to people they were never built for. Joe and OG walk through five genuinely legitimate, sometimes powerful tools, cash value life insurance, municipal bonds, qualified longevity annuity contracts, net unrealized appreciation, and complex charitable trusts, and draw a clear line between the tiny slice of people these actually help and the much larger crowd who gets pitched them anyway. If you've ever had someone offer you a "special" financial strategy and wondered whether it was genius or a sales tactic, this episode gives you the framework to tell the difference.What You'll Walk Away WithWhy cash value life insurance almost never makes sense as a savings vehicle, and the very narrow situations where it actually doesThe real math behind municipal bonds, and why the "tax-free" appeal often costs more in lost growth than it saves in taxesA clear-eyed look at qualified longevity annuity contracts, and why giving up control of your money rarely makes sense at any wealth levelThe single tax strategy on this list that can genuinely save six figures over a lifetime: net unrealized appreciation on employer stockWhy "borrowing against your assets instead of selling them" can be brilliant or disastrous depending entirely on how the economy movesA blunt reality check on 72(t) distributions for early retirees, and why the five-year commitment trips more people up than the strategy itselfWhy "there's no free lunch" is the single question to ask about any complex financial product before you commit to itWhy This Matters NowThe financial industry has an incentive to make simple problems feel complicated, because complicated problems require expensive solutions. Most people's actual financial life doesn't need any of these five strategies, and that's not a failure, it's just math. But knowing what these tools are, who they're actually built for, and what they cost when misapplied means you can spot the difference between a legitimately smart move and a sales pitch dressed up as sophistication, whether or not you'll ever personally need any of them.From the BasementA Good Neighbor Day detour into Ted Williams's legendary 1941 season, when he refused to sit out the final day to protect a rounded-up .400 batting average, becomes a genuinely moving story about doing things the honest way even when nobody would've noticed otherwise.Resources MentionedStacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking toolStacking Benjamins Coaching Program — Joe and OG's new cohort program for financial coachesSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 1 weeks ago58 min
Is "This Time Different"? A FinCon Panel on AI, Inflation, and Interest Rates SB1902
Live from FinCon, Joe sits down with historian and bestselling author Joseph Moore, Paula Pant, and Jesse Cramer to talk about what's actually keeping people up at night: AI concentration in the stock market, inflation anxiety that won't fully fade, interest rates that feel "stuck," and a housing market that seems rigged against newcomers. The twist is that almost none of it is new. From a Scottish con man's fake country bonds to the 1830s stock that was over 30% of the entire market, to a refrigerator boom that happened during the Great Depression, this conversation uses 300 years of financial history to put today's anxieties in real perspective.What You'll Walk Away WithWhy "this time is different" has been true in every single era of financial history, and why that's actually reassuring, not alarmingThe real reason today's AI-heavy stock market concentration isn't as extreme as people fear, compared to genuine historical outliersWhy equal-weighted index funds tend to underperform market-weighted ones, and what that reveals about betting against your own winnersA fascinating historical parallel between AI infrastructure spending today and the railroad boom of the 1800s, and where that comparison breaks downWhy the fastest way to build real wealth during a technological boom is often working in the industry, not investing in itHow the "golden handcuffs" of low mortgage rates are quietly fueling a broader sense of economic pessimism, even during a strong economyWhy increasing your income is one of the few truly controllable levers in your financial life, and why it usually takes longer than people expectWhy This Matters NowEvery generation convinces itself that its economic moment is uniquely unprecedented, uniquely uncertain, uniquely dangerous. History suggests otherwise: markets concentrate around a handful of winners, technology booms take decades to actually change daily life, and financial anxiety tends to track personal experience more than actual data. None of that means today's concerns aren't real. It means the emotional weight of "this has never happened before" is usually misplaced, and understanding that can be the difference between panicking through a normal cycle and staying invested through one.Resources MentionedHow to Get Rich in American History by Joseph Moore — Joseph's USA Today bestselling book on 300 years of financial advice, what worked and what didn'tAfford Anything podcast — Paula Pant's showPersonal Finance for Long-Term Investors podcast — Jesse Cramer's showMen Go To Mars — sponsor mentioned in the episodeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 1 weeks ago1h 5m
Robin Wigglesworth: The Boring Market That Actually Runs the World SB1901
In April 2025, the bond market did something the stock market couldn't: it made a sitting president reverse course within days. Financial Times journalist Robin Wigglesworth, author of the new book A Fabulous Debt, joins Joe and OG to explain why bonds, dismissed for centuries as the dull corner of finance, are actually the bedrock everything else sits on. From a murdered medieval ruler in Venice to a Scottish con man who sold bonds for a country that didn't exist to the hedge fund collapse that nearly took down the global financial system, this is 900 years of history explaining exactly why the "boring" market is the one that actually moves empires.What You'll Walk Away WithWhy the bond market, not the stock market, is what actually forced a change of course during 2025's "Liberation Day" tariff chaosThe surprisingly wild origin story of the very first government bond, issued in 1171 Venice, and how it got its ruler killedHow the Dutch turned Venice's basic invention into a true market, and used it to fund their independence from a much larger empireThe incredible true story of a con man who sold real bonds for a fictional country and lured hundreds of settlers to their deathsWhy Long-Term Capital Management, staffed with Nobel laureates and legendary traders, collapsed almost overnight in 1998The biggest misconception most Americans have about U.S. government debt, and why the reality is more nuanced than the doom headlines suggestWhy the oldest investing mistake in 900 years of financial history is still the simplest one: borrowing too muchWhy This Matters NowMost people never think about bonds until something breaks, a rate spike, a market scare, a headline about the national debt, and by then it can feel too complicated to catch up on. But bonds quietly determine mortgage rates, corporate borrowing costs, and government policy in ways that touch daily life far more than most people realize. Understanding even the basics of how this market works, and how consistently it has shaped history, turns a vague sense of unease about "the economy" into something you can actually follow and make sense of.From the BasementA Bond-adjacent trivia detour (the James Bond kind, not the financial kind) reveals that Ian Fleming borrowed his spy's name from a real-life ornithologist, proof that even a show about medieval Venetian debt can't resist a pun. Plus, a Wall Street Journal headline on why the job market has quietly flipped in favor of workers without a college degree.Resources MentionedA Fabulous Debt by Robin Wigglesworth — Robin's new book on the 900-year history of bondsTrillions by Robin Wigglesworth — Robin's earlier book on the history of index fundsStacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking toolSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 1 weeks ago1h 3m
Five Signs Your Financial Advisor Might Not Be Great SB1900
"How do I know it's time to fire my advisor?" That question came up over and over at a recent retreat, enough that Joe knew it needed its own episode. Today he and OG walk through five real, specific red flags, not vague warnings about fees, but concrete signs that your advisor might be coasting, out of their depth, or simply not built for where your life is headed. If you've ever sat in a meeting with your advisor and wondered whether you're getting real value or just really good small talk, this one's for you.What You'll Walk Away WithWhy an advisor who knows your portfolio better than they know your actual life is a warning sign, not a complimentThe real reason a "free" advisor should make you more suspicious, not lessWhy an advisor working with literally anyone, instead of a defined type of client, often means shallower expertiseHow to tell the difference between a collaborative advisor relationship and one where you're quietly doing all the drivingWhy outgrowing your advisor isn't always about more money, sometimes it's about more complexity, and that's worth a real conversationA simple question to ask about fees that costs you nothing and might save you real moneyThe single clearest red flag of all: an advisor who leads with products instead of questionsWhy This Matters NowMost people have no natural way to judge whether their financial advice is actually good, since the whole reason you hired someone was that you didn't have the expertise to evaluate it yourself in the first place. That's not a flaw in you, it's exactly why concrete, observable signs matter more than a vague gut feeling. Knowing what a good advisor relationship actually looks like, real collaboration, a defined specialty, clear communication about fees and process, gives you a way to check in on that relationship without needing a finance degree to do it.From the BasementAn Earth, Wind & Fire trivia detour uncovers the real, long-hidden meaning behind "the 21st night of September," and a listener question from someone getting her first-ever 401k at 50 sparks a genuinely useful conversation about target-date funds, Roth versus pre-tax decisions, and the often-overlooked Rule of 55.Resources MentionedStacking Benjamins Field Kit — the all-in-one budgeting, privacy, credit and net worth tracking toolStacking Benjamins Benjamins After Dark meetups — local in-person Stacker meetup groupsYell Down the Stairs — submit a question for a future OG and Anna episodeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 2 weeks ago1h 6m
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 WithThe 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 payoffWhy working in an industry doesn't automatically make you qualified to invest in itThe real statistics behind stock picking: roughly two-thirds of individual stocks underperform the market averageWhy losing money on your first few stock picks might be the best possible outcome, and why winning right away can be dangerousA clear framework for position sizing, so a stock-picking hobby never puts your actual financial plan at riskThe real opportunity cost of stock picking as a "side hustle," and why it competes with your time as much as your moneyWhy a great company and a great stock investment are often two completely different thingsWhy This Matters NowThere'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 BasementA 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 MentionedStock Simplifier — Brian Feroldi's AI-powered stock research toolWhy Does The Stock Market Go Up? by Brian Feroldi — Brian's bestselling book on how the market worksAfford Anything podcast — Paula Pant's showPersonal Finance for Long-Term Investors podcast — Jesse Cramer's showSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
- 2 weeks ago1h 7m
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 WithWhy a single, long block of retirement often backfires, and what tends to happen to people's sense of purpose and friendships when it doesThe "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 endWhy a "flexibility fund" might matter more than a traditional retirement account for anyone planning to take real breaks, sabbaticals, or career pivots along the wayA simple four-option framework (stay, switch, scale back, or sail away) for deciding what to do when a chapter of work stops feeling rightWhy the fastest way to burn out is neglecting the "nurture" side of life, and why neglecting the "productivity" side leaves you financially fragile insteadA genuinely useful reframe on AI: not a threat to outrun, but a reason to double down on the specifically human parts of work and lifeWhy This Matters NowLonger 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 BasementA 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 MentionedLiving the 100-Year Life by Lynda Gratton — Lynda's book, workbook, and free diagnostic on the eight life threadsLife Threads podcast — Lynda's eight-episode podcast series exploring each threadThe 100-Year Life by Lynda Gratton and Andrew Scott — the original million-copy bestseller that started this line of researchSee 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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About The Stacking Benjamins Show
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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