The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
  • 4.4 (2K)
  • Investing
  • Updated Semiweekly

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

  1. 22h ago

    The SpaceX IPO Wasn't for You (and that's actually fine) SB1858

    SpaceX raised $75 billion in the largest IPO in history -- more than all 71 other IPOs combined so far this year. Shares jumped nearly 20% on day one. Elon Musk became the world's first trillionaire. And if you're a regular investor asking whether you missed out, Joe and OG have a very specific answer: the life-changing money was already gone before the ticker symbol appeared. Here's how IPOs actually work, who really wins, and why your index fund is probably going to own SpaceX anyway. What You'll Walk Away With Why the 20% first-day pop was largely an illusion for retail investors -- and what actually happened to the price between $135 and the moment you could buy itThe auction mechanics behind IPO pricing: why institutional investors with early access capture most of the return before the stock hits public marketsWhy OG argues that even putting a million dollars into SpaceX at the IPO price and making 20% isn't life-changing -- and why that math actually makes the risk harder to justify, not easierThe sobering stat: 71 other IPOs happened this year before SpaceX, raising a combined $36 billion between themHow SpaceX could still end up in your portfolio without you doing anything -- and which indexes will add it faster than others under new fast-entry provisionsWhy S&P 500 investors will have to wait: the three criteria any company must meet before joining, and why SpaceX's profitability timeline makes one of them complicatedThe six new space-themed ETFs Wall Street created in the past three months -- and what that pattern always signalsOG on why the person who got rich on SpaceX put money in before you knew it existed, and why you wouldn't have done it eitherWhy being wrong on a small speculative position might be the most valuable financial education available -- and OG's Thanksgiving pan storyOG and Anna on college planning: how to calculate your actual funding gap, why FAFSA still matters even if you won't qualify for need-based aid, and the high school glide path that protects your savings from market timing risk in the final four years Why This Matters Now Every few years a story like SpaceX comes along and makes every investor feel like they missed the trade of a lifetime. The real question isn't whether you missed SpaceX -- it's whether you have a plan that captures the next one automatically, without you having to call your shot. From the Basement Joe and OG dig into the SpaceX IPO mechanics, the FOMO math, and why index fund investors may own it soon anyway without lifting a finger. OG and Anna deliver the penultimate episode of their financial basics series with a full college planning walkthrough including the gap calculator, FAFSA, and the glide path strategy for the four years before tuition is due. Doug arrives with Meryl Streep trivia. The show introduces Scout, a new AI assistant built specifically for the Stacking Benjamins guides that only answers from the guides themselves -- and tells you when it doesn't know. Congratulations go out to Stacker Melissa, who finished her last day of work. Resources Mentioned Stacking Benjamins Guides -- college planning, tax, and workplace benefits guides with new Scout AI assistant; stackingbenjamins.com/guidesStacking Benjamins Basics Guide -- stackingbenjamins.com/basicsguideStacking Benjamins Scorecard -- stackingbenjamins.com/scorecardStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201The College Investor -- Robert Farrington; collaborator on the college planning guide; thecollegeinvestor.comGranola AI -- meeting notes tool; granola.ai/sbStacking 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.

    1h 8m

  2. 3d ago

    Financial Rules That Sound Smart Until You Actually Test Them (Money "Rules" We Had to Unlearn) SB1857

    Everyone inherited financial wisdom from somewhere -- a parent who clipped coupons at three different grocery stores, a first job, a financial guru, or just the culture you grew up in. Some of those beliefs serve you. Some of them quietly hold you back. Chris Hill of Money Unplugged joins Joe, Paula Pant, and OG to share the money habits they've had to unlearn -- and then the whole group plays a round of In or Out on some of personal finance's most popular rules. What You'll Walk Away With Why Paula's childhood coupon-clipping ritual wasn't really about frugality -- it was about an unstated belief that your time is worth nothing, and how that belief shapes everythingChris Hill's 20-year belief that dividend-paying stocks are for old people -- and the specific Apple moment in 2012 that finally broke itOG's admission that despite the math argument, he's never once seen someone actually execute the "invest the difference" 30-year vs. 15-year mortgage strategy in real lifeWhy "more money will fix this" is the belief most people never fully unlearn -- and OG's honest accounting of what he thought at $17,000, $170,000, and beyondThe In or Out verdict on five popular financial rules: everyone should own a home, pay off debt before investing, never carry a mortgage into retirement, you need a budget to build wealth, and whether financial independence is mostly behavior or mathPaula's anti-budget framework -- why it works when there's a wide enough gap between income and spending, and the one scenario where a real budget actually becomes necessaryChris Hill on why surrounding yourself with people who aren't impressed by your success might be the most underrated risk management tool in your financial lifeThe Isaac Newton problem applied to successful people: why brilliance in one area creates a false confidence in all areas -- and why guardrails matter more the more successful you getWhy OG argues that if the leverage-your-mortgage math truly worked reliably, you'd be using the same logic in your Schwab account -- and why almost nobody doesWhat Melissa from Detroit did this week that every Stacker listening should know aboutWhy This Matters Now The most expensive financial decisions are often the ones you've never questioned because someone you trusted taught them to you early. This episode is the permission slip to stress-test those beliefs. From the Basement Chris Hill joins Joe, Paula Pant, and OG to dig into the money habits and inherited beliefs they've each had to unlearn -- before the whole group debates whether five of personal finance's most popular rules actually survive contact with real life. Doug arrives with Lou Gehrig trivia and makes everyone do inflation math from 1939. Chris plays for Team Jesse Cramer. The gap between first and second place closes considerably. Resources Mentioned Money Unplugged podcast -- Chris Hill; recent episodes featuring Joe Saul-Sehy and Paula Pant; available wherever you listen to podcastsAfford Anything podcast -- Paula Pant; upcoming episode on how to think through business decisions with a Harvard professor and longtime practitionerSurfshark VPN -- surfshark.com/stackingb; code stackingbee for four extra monthsStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201OG financial planning calendar -- stackingbenjamins.com/ogStacking 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.

    57 min

  3. 5d ago

    Isaac Newton Lost 80% of His Fortune in a Bubble -- What That Teaches Every Investor (SB1856)

    Thanks to Surfshark for sponsoring the show. Go to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN! Isaac Newton was one of the smartest humans who ever lived. He also bought into the South Sea Bubble, sold for a profit, watched it keep climbing, bought back in out of pure FOMO, and rode it all the way down to an 80% loss that haunted him until he died. Ben Carlson, co-host of the Animal Spirits podcast and one of the sharpest minds at Ritholtz Wealth Management, joins Joe and Anna to walk through centuries of market history -- bubbles, crashes, and the psychology that makes smart people do dumb things with money. Anna also helps a Stacker named Louie untangle his 401(k) sources and figure out whether it's finally time to bring in a professional. What You'll Walk Away With Why Isaac Newton's South Sea Bubble loss still ranks among history's most instructive investing failures -- and why it had nothing to do with intelligenceBen's framework for why risk means something completely different depending on where you are in your life cycle -- and why a market crash genuinely doesn't matter the same way to a 25-year-old and a 55-year-oldThe wrong lesson an entire generation learned from 2008 -- and why everyone preparing for the last crisis missed the next seventeen years of bull marketWhy Japan's three-decade stock market bubble is the best real-world case for diversification -- and why it doesn't translate as cleanly to the US as people assumeThe behavioral reason complex investment strategies are easy to sell and nearly impossible to hold through a downturn -- while simple strategies survive the painWhy Ben's firm discovered that the hardest financial transition isn't saving for retirement -- it's actually learning to spend the money once you get thereThe Beanie Babies divorce court story that perfectly captures what every bubble looks like from the outsideAnna and OG's take on Louie's four-source 401(k): why it's simpler to manage than it looks, and why "move everything to Roth" is the wrong instinct for most DIY investorsThe Roth conversion icing-on-the-cake strategy: how to use pre-tax and Roth buckets together to manage your tax bracket year by year in retirementWhy one financial pro has a surprisingly negative take on HSAs at death -- and the timing problem that makes spending one down in retirement genuinely tricky Why This Matters Now Every market cycle feels unprecedented while you're living through it. Understanding the actual constant -- human psychology, not headlines -- is the difference between riding out volatility and becoming a cautionary tale, smart as you might be. From the Basement Ben Carlson joins Joe and Anna to walk through centuries of bubbles, crashes, and the psychological wiring that makes both geniuses and ordinary investors do the same dumb things. Doug arrives with Statue of Liberty trivia tied to America's upcoming 250th anniversary. A Stacker calling himself Louie -- and getting Anna instead of OG, much to his surprise -- asks for help simplifying his 401(k) and figuring out his Roth conversion strategy, and gets a reminder that he's already doing better than he thinks. Resources Mentioned Risk and Reward: How to Handle Market Volatility and Build Long-Term Wealth by Ben Carlson -- available wherever books are soldAnimal Spirits podcast -- Ben Carlson and Michael Batnick; available wherever you listen to podcastsRitholtz Wealth Management -- referenced for prior guests Barry Ritholtz, Josh Brown, and Nick MaggiulliWhere Are the Customers' Yachts? by Fred Schwed -- referenced for the famous quote on the emotional experience of losing moneyPaul Merriman's research on asset allocation -- paulmerriman.comStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins voicemail line -- stackingbenjamins.com/yelldownstairsStacking 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.

    1 hr

  4. Jun 15

    AI Agents Want to Trade Your Stocks and Shop With Your Credit Card -- Here's Why That's a Problem (SB1855)

    Robinhood just launched agentic trading -- an AI that can execute stock trades and purchases on your behalf using criteria you set in advance. There's also a new agentic credit card that can shop for you automatically. Joe and Anna dig into why handing execution over to a machine is fundamentally different from using AI as a thinking partner -- and why the people most excited about AI agents for their money are often the same people who would never trust a human advisor with it. What You'll Walk Away With Why the psychology of trusting AI with money while distrusting human advisors doesn't hold up -- and what's actually driving itThe difference between using AI to expand your thinking and using it to execute decisions -- and why only one of those is dangerousHow AI agents eliminate the friction that protects you from your own worst financial impulses -- and why that's exactly how consumer debt gets worseJoe's four-question framework for knowing when an AI agent is actually helping versus when it's just automating overspendingWhy Doug's experience building computer systems made him more skeptical of AI agents, not less -- and what changedThe debt sequencer framework from OG and Anna: how to rank every debt by interest rate, add an honest emotional layer, and decide where the next dollar actually goesWhy the debt snowball versus avalanche debate has a cleaner answer than most people think -- and when the math genuinely doesn't matterThe one thing that happens to almost every client's bonus money if they don't have a pre-decided allocation plan -- and how to fix it before the money arrivesWhy paying off a 3% mortgage might be the right call even when the spreadsheet says it isn't -- and the taxes-and-insurance math that makes the house payment conversation more complicated than it looksWhy the Stacking Benjamins guides now have an AI component that only draws from the guide itself -- and why it tells you when it doesn't know somethingWhy This Matters Now Every time a company makes it easier to spend or trade without thinking, it's not because they want you to make better decisions. Understanding where AI genuinely helps -- thinking, organizing, comparing -- versus where it hurts -- executing, spending, trading -- is one of the most important financial literacy questions of the next decade. From the Basement Joe and Anna dig into Robinhood's new agentic trading and credit card features and work out where the line between useful and dangerous actually sits. OG and Anna follow with the debt sequencer -- a framework for ranking every debt you have and deciding where the next dollar goes, with room for both math and emotion. Doug arrives with kite-flying trivia that connects to one of the most famous names in American history. Anna is back without OG, which Doug predicts will produce the highest ratings in show history. Resources Mentioned CNBC -- "Your AI agent can now trade for you on Robinhood and buy stuff with your credit card, too"; linked at stackingbenjamins.comThe College Investor with Robert Farrington -- referenced for prior deep dive on AI financial advice accuracyStacking Benjamins Guides -- college planning, tax planning, and HR benefits guides with new AI component; stackingbenjamins.com/guidesStacking Benjamins Basics Guide -- season one and season two workbooks free at stackingbenjamins.com/basicsguideStacking Benjamins Scorecard -- stackingbenjamins.com/scorecardStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Field Kit Finance -- fieldkitfinance.comStacking Benjamins BAD Groups -- stackingbenjamins.com/badStacking 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.

    1h 2m

  5. Jun 12

    8 Signs You're Winning With Money SB1854

    Thanks to Surfshark for sponsoring the show. Go to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN! You might not look rich on Instagram. That doesn't mean you're behind. Joe, Paula Pant, Jesse Cramer, and Anthony Weaver from About That Wallet work through eight real signs that your financial life is on track -- covering stability, behavior, and mindset -- and spend just as much time on why we're all so bad at recognizing the wins we've already had. What You'll Walk Away With Why a $1,000 emergency fund puts you in the top 40% of Americans -- and what Jesse's registered nurse versus Uzbek architecture professor framework tells you about how big yours actually needs to beThe debt-to-income ratio question nobody asks: would you rather have a 10% DTI and zero savings, or $1 million invested and a 45% DTI? Paula and Anthony work out their actual answers liveWhy someone making $250,000 and living paycheck to paycheck is less financially trustworthy than someone making $60,000 with a two-month buffer -- and what that reveals about the real gameAnthony's dream walk framework: the questions he asks clients to make sure their day-to-day financial habits are actually pointed toward what they say they wantWhy the trend matters more than the number -- and the one thing Jesse tracks monthly that most people miss when they're focused only on net worthThe peace of mind problem Paula names that most personal finance conversations skip entirely: there is very little correlation between the numbers in your accounts and your actual anxiety levelWhy Jesse thinks prioritizing stress reduction over optimization might actually produce better long-term outcomes than squeezing every percentage pointThe Instagram tell that almost none of the visible wealth you're comparing yourself to is real -- and the Tai Lopez rental strategy that proves itAnthony's story about the client who needed permission to sell investments to feed her kids -- and why money as a tool looks completely different at every income levelWhy money is the easiest possible scorecard -- and how that ease is exactly what makes it so dangerous as a proxy for self-worthWhy This Matters Now The comparison pressure has never been higher and the metrics have never been more visible. This episode is a reminder that the signs of real financial health are mostly invisible on the internet -- and that you might already be further along than you think. From the Basement Joe, Paula Pant, Jesse Cramer, and Anthony Weaver from About That Wallet work through eight signs of financial progress from a wisdom.com piece while talking about drone footage FOMO, Tai Lopez's rental Lamborghinis, and why somebody in Florida held a half-eaten grilled cheese sandwich for ten years before selling it on eBay. Resources Mentioned About That Wallet podcast -- Anthony Weaver; available wherever you listen to podcastsAfford Anything podcast -- Paula Pant; recent episode with Dr. John La Puma on why going outside improves health and productivityPersonal Finance for Long-Term Investors (FILTI) -- Jesse Cramer; recent AMA episode on retirement planning questionsFreedom app -- referenced by Paula for blocking Instagram; freedom.toSurfshark VPN -- surfshark.com/stackingbee; code stackingbee for four extra monthsStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins Community -- stackingbenjamins.com/basementStacking Benjamins BAD Groups -- stackingbenjamins.com/bad See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1h 4m

  6. Jun 10

    Helping Mom With Money Before It's Too Late (SB1853)

    One day you're comparing Roth IRA options. The next you're helping Mom navigate long-term care paperwork, fighting with a bank over a power of attorney document, and wondering how anyone manages all this without losing their sanity. Welcome to the world of financial caregiving. Today, certified financial planner and financial journalist Beth Pinsker joins us to share the lessons she learned while helping manage her mother's finances during a health crisis. From powers of attorney that don't always work when you need them to the surprising warning signs that an aging parent may need help, Beth offers practical advice every family should hear before an emergency arrives. Then in our headline segment, a blast from the financial past: unconventional mortgages are making a comeback. Are these products helping qualified borrowers who don't fit the traditional mold—or are we seeing early warning signs of the next lending problem? Plus, Doug celebrates the legacy of Ray Charles with today's trivia challenge. In Today's Episode Why financial caregiving is far more complicated than most families expectThe paperwork Beth wishes she'd completed before her mother's medical emergencyHow power of attorney works—and why it may not work as smoothly as you thinkWarning signs that a parent may be struggling financially or cognitivelyThe surprising problems created by passwords, two-factor authentication, and modern banking systemsWhy trusted contacts, healthcare proxies, and emergency document folders matterCommon family conflicts that emerge during caregiving and estate settlementWhether today's unconventional mortgages should worry homebuyersThe important differences between today's lending environment and 2008Ray Charles trivia from Doug Our Guest Beth Pinsker Beth Pinsker is an award-winning financial journalist, Certified Financial Planner™, and author of My Mother's Money: A Guide to Financial Caregiving. Through both her professional expertise and personal experience, Beth helps families prepare for the financial realities of caring for aging loved ones. Mentioned In Today's Show My Mother's Money: A Guide to Financial Caregiving by Beth PinskerLong-term care insuranceFinancial power of attorneyHealthcare proxy documentsTrusted contactsEstate planning basicsNon-conforming mortgagesRay Charles Doug's Trivia Which Ray Charles hit became an official state song? Better Call Saul...Sehy & OG What financial caregiving preparations have you already completed—and which ones are still sitting on your to-do list? See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

    1h 16m

  7. Jun 8

    59% of Retirees Left the Workforce Earlier Than Planned -- Are You Ready If It Happens to You? SB1852

    Most people plan their retirement like they control the date. The data says they don't. A new Society of Actuaries study found that 59% of retirees stopped working earlier than expected -- and for most of them, the decision wasn't theirs. Health setbacks, job loss, caregiving demands, and plain old job dissatisfaction all showed up before the spreadsheet said it was time. Joe and OG dig into what the numbers actually mean, who's most at risk, and the specific steps that create real flexibility before retirement finds you. OG and Anna follow with a full walkthrough of equity compensation -- RSUs, ESPPs, and stock options -- including the tax surprise that catches most people off guard. What You'll Walk Away With Why 59% of retirees left the workforce earlier than they planned -- and why only 6% left laterThe income gap nobody talks about: how high earners retire early mostly because they wanted to, while lower earners are pushed out by health and job lossWhy Coast FIRE math falls apart the moment your income stream stops before you planned -- and what that means for how aggressively you should be saving right nowThe one manager change that can end a 20-year career overnight -- and why keeping your network warm is one of the most underrated retirement prep moves availableThe 30-year mortgage paid like a 15-year analogy: why building financial margin now means retirement can happen on your terms, not someone else'sHow to prepare for the emotional side of early retirement -- including the identity shift, the relationship changes, and the pent-up demand that makes the first year unexpectedly wildRSUs versus stock options versus ESPPs: what each one actually means, how they're taxed differently, and why getting a grant without a strategy is the most expensive mistake in equity compThe 5-10% concentration rule: how much of your net worth should be tied to company stock -- and why your paycheck counts in that mathThe RSU tax trap: why your company withholds at 22% but you might actually owe 37% -- and why spending all your RSU money on a pool before April is a terrible ideaStacker Kiki's accountability letter: the complete list of what she's cutting, what she refuses to cut, and why the gamification of frugality is more powerful than white-knuckling itWhy This Matters Now You may not get to choose your retirement date. But you do get to choose how prepared you are for the day it arrives. The people in this study who retired early by choice had one thing in common: they'd built enough margin that the choice was actually theirs. From the Basement Joe and OG dig into a USA Today piece on the surprising frequency of unplanned early retirement -- and what to do about it before the decision gets made for you. OG and Anna deliver episode five of their financial basics series with a full equity compensation walkthrough, including the tax withholding gap that sends people to April with surprise bills. Doug arrives with Mickey Mantle trivia. A community poll on how often Stackers check their portfolios during headlines produces results that are more honest than most people expected. Stacker Kiki writes a detailed letter about her intentional spending cuts, and OG quietly admits he's been burning through hotel shampoo samples all year. Resources Mentioned Society of Actuaries Retirement Risks Survey -- released May 2026; linked at stackingbenjamins.comUSA Today -- "Most of Us Retire Earlier Than Planned. Here Are the Top Reasons." by Daniel DeVise; linked at stackingbenjamins.comStacking Benjamins Basics Guide -- season one and season two workbooks free at stackingbenjamins.com/basicsguideStacking Benjamins Scorecard -- stackingbenjamins.com/scorecardStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201; Kevin Bailey's hot take on this week's pieceStacking Benjamins YouTube channel -- full OG and Anna equity comp series; youtube.com/stackingbenjaminsStacking Benjamins BAD Groups -- meetups in Boston, Seattle, Twin Cities, Mankato, Tucson, and more; stackingbenjamins.com/badStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking 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.

    1 hr

  8. Jun 5

    Why High Earners Still Feel Broke (And What to Do About It) SB1851

    Thanks to Surfshark for sponsoring the show. Go to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN! You're making more money than you ever have. Your net worth on paper looks great. And yet somehow, there's still too much month left at the end of the money. Joe, OG, Paula Pant, and Jesse Cramer dig into why high earners feel financially squeezed -- and why the answer is almost never what you think it is. Spoiler: it's usually not the lattes, it's not too many accounts, and it might not even be a spending problem at all. What You'll Walk Away With Why lifestyle inflation doesn't feel like inflation -- it feels like deserved progress, and why that's exactly what makes it so hard to catchThe crucial difference between feeling like you didn't save enough and actually not saving enough -- and why OG's take on this is the most useful thing in the episodePaula's one big fixed cost audit: why making a single large decision beats constantly making small DoorDash decisionsWhy tracking your spending is the calorie counting of personal finance -- only useful short-term, but powerful for getting an honest snapshot before you make any changesThe paper wealth trap: why a high net worth and strong portfolio can coexist with genuinely tight monthly cashflow and why people conflate themJesse's one-line-item challenge: find one thing on last month's credit card statement you wish you hadn't spent, cut it, and see what happens to your motivationWhy OG's advice to "just decide not to feel squeezed anymore" is less dismissive than it sounds -- and the number of times the actual math completely contradicted a client's feelingsThe boats conversation: why a good financial advisor's job isn't to tell you whether to buy the boat but to show you what it costs in terms of your actual goalsWhy comparing your savings rate to the FIRE community can make you feel terrible about saving an objectively impressive amount of moneyThe goal clarity test: if you can't articulate what you're saving toward in specific, time-bound, dollar-denominated terms, the squeezed feeling probably has nothing to do with your budgetWhy This Matters Now Housing, food, and transportation costs are genuinely higher. That part is real. But for a meaningful chunk of the people who feel financially squeezed, the math and the feeling are pointing in different directions. This episode is about figuring out which one you're actually dealing with -- and what to do differently once you know. From the Basement Joe, OG, Paula Pant, and Jesse Cramer work through the Wall Street Journal's reporting on why so many Americans feel financially squeezed even at high income levels -- and whether the problem is real, psychological, or both. OG is recording from a conference adjacent to Disney World and has opinions about wood delivery, boats, and people who feel bad about saving $87,000 a year. Paula gets the giggles. The trivia competition features a man who mowed Steve Wozniak's lawn and had the license plate to prove it. OG wins with suspicious precision. Ronald Wayne, who sold his 10% of Apple for $800 twelve days after founding the company, has a worse story than anyone on this podcast. Resources Mentioned Financial Samurai -- referenced for the lifestyle inflation quote; financialsamurai.comAfford Anything podcast -- Paula Pant; Joe joins most Tuesdays for listener Q&APersonal Finance for Long-Term Investors -- Jesse Cramer; current series: 14 risks in retirement, Charlie Munger inversion framework; two-part series now completeStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201OG financial planning calendar -- stackingbenjamins.com/ogStacking 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.

    1h 5m
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4.4
out of 5
1,950 Ratings

About

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

Information

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

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