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  • Thinking in Bets: Annie Duke on Making Smarter Decisions When You Don't Have All the Facts - Greatest Hits! (SB1837)

    Thinking in Bets: Annie Duke on Making Smarter Decisions When You Don't Have All the Facts - Greatest Hits! (SB1837)
    May 4 2026

    What if the reason your investment decisions feel so hard isn't the market -- it's how you're wired to think about outcomes? Annie Duke spent years as a professional poker player winning over $4 million in tournaments, then devoted the next chapter of her career to understanding why smart people consistently make bad decisions. The answer has nothing to do with intelligence and everything to do with how we confuse results with quality. She brings the full framework down to the basement today.

    What You'll Walk Away With

    • Why certainty is the enemy of good decision making -- and the mindset shift that makes uncertainty feel like an advantage instead of a threat
    • The Pete Carroll problem: how tying the outcome of a decision to the quality of the decision is quietly wrecking how you evaluate your investments
    • Why being smarter actually makes this bias worse -- and how intelligent people spin data to confirm what they already believe more effectively than anyone else
    • The difference between wanting to be right and wanting to be accurate -- and why that single distinction changes everything about how you process new information
    • How to hold your beliefs as "works in progress" rather than positions to defend -- and why that opens you up to information that actually improves your decisions
    • Why the stock market's short-term volatility is almost never the signal investors treat it as -- and what a 40-year Berkshire Hathaway chart actually tells you
    • The poker table parallel to long-term investing -- and why you can make all the right moves and still lose, which means a bad outcome never proves a bad decision
    • What the Philly Special play reveals about how we reward boldness only when it works -- and what that tells you about how you judge your own financial choices
    • A listener question on market-cap weighted index funds -- why the s and p is built the way it is and what you'd actually need to do to weight it differently
    • The best personal finance and business books the crew is reading right now -- including picks from OG that go well beyond the usual recommendations

    Why This Matters Now

    For Stackers in their 40s watching a volatile market and second-guessing decisions that were perfectly sound six months ago, this episode is a direct intervention. The temptation to call a good decision bad because the market moved against you -- or to abandon a long-term strategy because of a short-term result -- is exactly the bias Annie Duke has spent her career studying. The framework she brings today doesn't just apply to poker. It applies to every financial decision you'll make for the rest of your life.

    From the Basement

    Annie Duke joins Joe and OG to walk through the decision-making framework behind her book Thinking in Bets -- including the Super Bowl story that reframes how most people evaluate every financial move they've ever made. The headline segment tackles parents spending six figures on kids' extracurriculars and what the trade-off actually looks like for retirement savings. Doug arrives with poker-themed trivia about the all-time tournament earnings leader, gets it mostly right, and declares victory anyway. Whether the basement poker tournament ended in anyone's favor is a matter of some dispute.

    Resources Mentioned

    • Thinking in Bets by Annie Duke -- available wherever books are sold
    • Annie Duke's website and weekly newsletter -- annieduke.com
    • Annie Duke on Twitter -- @AnniedDuke
    • The Truth About Money by Ric Edelman -- recommended by Joe
    • Set for Life by Scott Trench -- recommended by Joe
    • Broke Millennial by Erin Lowry -- recommended by Joe
    • How to Be a Financial Grownup by Bobbi Rebell -- recommended by Joe
    • The Behavior Gap and The One-Page Financial Plan by Carl Richards -- recommended by OG
    • Fooling Some of the People All of the Time by David Einhorn -- recommended by OG
    • Built to Sell by John Warrillow -- recommended by OG
    • The E-Myth by Michael Gerber -- recommended by Joe
    • The Goal by Eliyahu Goldratt -- recommended by Joe
    • Stacking Benjamins Community -- stackingbenjamins.com/basement


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    1 Std. und 3 Min.
  • Invest Like the 1%? What to Steal, What to Scale, and What to Skip (SB1836)

    Invest Like the 1%? What to Steal, What to Scale, and What to Skip (SB1836)
    May 1 2026
    You've seen the ads. Invest like the ultra-wealthy. Get access to what the 1% does. But what does the 1% actually do -- and how much of it should a normal person try to copy? Joe, OG, comedian and finance educator Roxanne Duckels, and Jesse Cramer run every popular "rich people investing" idea through a simple filter: steal it, scale it, or skip it. The answers will surprise you -- especially the one where OG wants to delete an entire asset class from existence.What You'll Walk Away WithWhy long-term thinking is the one habit the 1% has that every Stacker should steal immediately -- and the short-term execution piece most people miss when they tryThe tax strategy obsession that the wealthy genuinely use -- and why Jesse ranks it seventh on his list of financial priorities, not firstWhat paying for advice actually means when you're smart enough to do it yourself -- and why the wealthiest people surround themselves with even smarter people anywayThe alternative investment marketing trap hiding inside every "invest like the rich" pitch -- and OG's case for why most people have no business touching any of itWhy the accredited investor designation protects almost no one -- and what the real risk is when you lock up money in illiquid investments chasing slightly better returnsThe leverage conversation that exposes a contradiction hiding in plain sight for every real estate investorWhy Roxanne's path to financial independence started with filling her gas tank all the way up -- and what that tells you about long-term thinking at any income levelThe one question that should precede any alternative investment conversation: does the expected return actually beat what publicly traded equities already offer?What the trivia competition scoreboard looks like heading into the back half of the year -- and whether OG's historic lead is as safe as it looksWhy rich habits and "what the 1% does" are two completely different things -- and which one is actually worth chasingWhy This Matters NowIn a noisy market environment, the "invest like the wealthy" pitch gets louder every time volatility spikes. Private credit, non-traded REITs, leveraged real estate, alternative assets -- the marketing machine never stops. For Stackers in their 40s who've built something real and don't want to blow it chasing a category that mostly benefits the people selling it, this episode is a useful reset. The habits worth stealing from the 1% turn out to be remarkably unglamorous.From the BasementJoe, OG, Roxanne Duckels from Finance Rox, and Jesse Cramer run the "invest like the rich" playbook through a steal-it-scale-it-skip-it framework -- and nobody agrees on everything, which is exactly what makes it useful. Doug arrives with Mayday trivia about the origin of the distress call and the year it was coined, which turns into one of the cleaner trivia finishes of the season. Whether the basement scoreboard moved in OG's favor or Jesse closed the gap is a question best answered with your earbuds in.Resources MentionedFinance Rox -- Roxanne Duckels on YouTube and Instagram @FinanceROXPersonal Finance for Long-Term Investors -- Jesse Cramer's podcast, wherever you listenStacking Benjamins Newsletter (The 201) -- recent issue: brokerage vs. UTMA/UGMA vs. Trump accounts for kids; stackingbenjamins.com/201Stacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Community -- stackingbenjamins.com/basementStacking Benjamins Meetups -- stackingbenjamins.com/badSee 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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    57 Min.
  • Mrs. Dow Jones on How to Become a Future Rich Person (Without Giving Up Your Life) SB1835

    Mrs. Dow Jones on How to Become a Future Rich Person (Without Giving Up Your Life) SB1835
    Apr 29 2026

    Haley Sacks didn't grow up knowing what a 401k was. She was nannying for a kid named Winthrop on the Upper East Side, doing comedy at night, and getting paid cash under the table. Then she sat in an HR meeting and her eyes glazed over -- and she decided that was the last time she'd be caught unprepared with her own money. Today she's Mrs. Dow Jones, with millions of followers and a new book. The basement finally got her in the chair, and she did not hold back.

    What You'll Walk Away With

    • The "future rich person" framework -- what separates people quietly building wealth from everyone else performing it
    • Why the biggest wealth trap isn't overspending -- it's the psychological pull of looking rich before you are
    • How automation is the real secret behind Haley's path to millionaire status -- and why willpower alone was never going to get her there
    • The action movie analogy that finally makes the debt-versus-investing debate make sense -- and which one you tackle first
    • Why your fixed expenses might be the actual problem -- and the two levers you can pull when the math doesn't work
    • The "money date" habit that keeps Haley on track -- and how to make it something you'll actually do every month
    • What a mise en place approach to your finances looks like -- and the four accounts every future rich person needs in place before anything else
    • Why cutting spending has a floor but earning more doesn't -- and how to think creatively about your income ceiling
    • The mortgage volatility conversation hiding in this episode -- including OG's take on where rates actually belong historically and why "date the rate" might be the most useful three words in real estate right now
    • Why comparison is derailing more financial plans than bad investments ever could

    Why This Matters Now

    If you're in your 40s and you still feel like the millionaire milestone belongs to someone else's story -- someone who started earlier, earned more, or just had better instincts -- this episode is a direct challenge to that belief. Hailey Sacks didn't have better instincts. She had a glazed-over HR meeting and a determination not to be caught unprepared twice. The foundation she built after that moment is exactly what she walks through today.

    From the Basement

    Mrs. Dow Jones herself -- Haley Sacks -- finally makes it down the stairs and does not disappoint. Joe and OG close the episode with a Wall Street Journal headline on mortgage rate volatility and what it actually means for anyone trying to buy, move, or refinance right now. OG lands what may be the cleanest take of the season: when should you borrow money? When you need to borrow money. Doug arrives with Dow Jones trivia about the longest-tenured company in the index, which turns out to have been added in 1932 and is hiding in plain sight on every household shelf. Whether the basement scoreboard had anything to do with Procter & Gamble is a question best answered with your earbuds in.

    Resources Mentioned

    • Future Rich Person by Haley Sacks (Mrs. Dow Jones) -- pre-order with $700 in bonuses at mrsdowjones.com/book; releases May 12th
    • Mrs. Dow Jones on Instagram and YouTube -- @MrsDowJones
    • Mrs. Dow Jones podcast -- Financial Therapy
    • Wall Street Journal mortgage volatility article by Veronica Dagher and Ben Eisen -- linked at stackingbenjamins.com
    • Stacking Benjamins Vault -- stackingbenjamins.com/vault
    • Stacking Benjamins Meetups -- stackingbenjamins.com/bad
    • Stacking Benjamins Community -- stackingbenjamins.com/basement


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    1 Std. und 4 Min.
  • Index Investing 101: Stop Picking Funds and Start Building the Mix That Actually Works (SB1834)

    Index Investing 101: Stop Picking Funds and Start Building the Mix That Actually Works (SB1834)
    Apr 27 2026
    Most investors spend their energy asking the wrong question. It's not which fund is best -- it's which combination of funds gets you to your actual goal at a cost and complexity level you'll actually maintain. Joe and OG break down the full index investing playbook: where to start, when to add complexity, what Wall Street calls indexing that really isn't, and the one number that should change how you think about your entire portfolio.What You'll Walk Away WithWhy the real argument for index investing isn't that nobody beats the market -- it's that you can't predict who will do it nextThe crockpot principle of index investing -- and why the self-cleaning oven analogy might be even betterWhy the S&P 500 and the total stock market index are closer than most people think -- and which one Joe is increasingly favoring for the long runThe $100,000 turning point: what changes about your investment strategy when the portfolio gets big enough to get scientificThe first two additions most Stackers should consider beyond their core index -- and why OG would actually add more than twoWhy mixing index funds from different companies can quietly undermine your diversification without you ever knowing itHow to replace the word "index" with "list" to instantly identify whether a product is actually doing what you think it isThe buffered ETFs, factor ETFs, and active ETFs that call themselves indexes -- and why most Stackers should walk right past themWhy you're not racing against the index -- you're on a road trip -- and what that shift in framing changes about every investing decisionThe season one recap from OG and Anna's financial planning basics series -- plus the free workbook that ties all seven episodes togetherWhy This Matters NowIn your 40s, the portfolio is finally big enough to matter -- and that's exactly when the temptation to complicate things gets strongest. New products, new strategies, and new buzzwords show up constantly, each promising a smarter approach. The investors who come out ahead aren't the ones who found the best fund. They're the ones who built something simple enough to maintain, scientific enough to optimize, and sturdy enough to hold through the moments when everything feels like it's falling apart.From the BasementJoe and OG dig into the full index investing playbook -- from the first fund a beginner should buy to the asset class combinations that actually improve long-term outcomes once the portfolio gets big enough to warrant it. OG and Anna close out their seven-week financial planning basics series with a full recap and the surprise release of a free downloadable workbook at stackingbenjamins.com/basicsguide. Doug arrives with Nolan Ryan trivia that connects strikeout records to index investing in a way that only the basement could pull off. Whether the analogy fully lands is a question best answered with your earbuds in.Resources MentionedThe Simple Path to Wealth by JL Collins -- referenced as the foundational text for beginner index investorsPrior interviews with JL Collins: Interview 1 and Interview 2Paul Merriman's annual asset class research -- referenced for data on adding small cap value and international to a core S&P portfolio; paulmerriman.comiShares -- referenced as an example of a consistent index fund family worth staying withinJP Morgan Guide to the Markets -- referenced in prior episode; available at jpmorgan.comStacking Benjamins Basics Guide -- free seven-episode workbook at stackingbenjamins.com/basicsguideStacking Benjamins Newsletter (The 201) -- weekly investing hot takes from Kevin Bailey at stackingbenjamins.com/201Stacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Meetups -- stackingbenjamins.com/badSee 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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    57 Min.
  • How to Find the Money Leaks Hidden in Your Financial Statements (SB1833)

    How to Find the Money Leaks Hidden in Your Financial Statements (SB1833)
    Apr 24 2026

    Most people glance at their balance and move on. Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer argue that's exactly where the money quietly disappears. This week they go statement by statement, credit card through brokerage, and share what actually deserves your attention and what you can safely ignore.

    In this episode:

    The one thing on your credit card statement that trips up even careful spenders, why focusing on your 401k rate of return is the wrong move, the underinsured coverage gap most homeowners and drivers don't know they have, and the tax planning opportunities hiding inside your brokerage account.

    Biggest takeaways:

    Sort your credit card transactions highest to lowest. The leak with a comma in it will find you faster than you'll find it.

    Your 401k contributions matter more than your returns. Contributions are within your control. Returns aren't. Check that your payroll deductions are actually landing in the account, because the IRS does not look kindly on companies that miss that.

    Check your homeowner's insurance rebuild value every few years. Labor and material costs have changed dramatically. If you bought your policy when you bought your house and never revisited it, there is a good chance you are significantly underinsured.

    In a taxable brokerage account, understand whether you're holding short-term or long-term gains before you make any moves. The difference in what you'll owe can be substantial.

    Also in this episode:

    Jesse Cramer previews an upcoming episode of Personal Finance for Long-Term Investors on why target date funds may be underperforming by more than you think.

    Resources mentioned:

    • Jesse Cramer's podcast: Personal Finance for Long-Term Investors
    • Paula Pant's podcast: Afford Anything
    • The Stacking Benjamins scorecard: stackingbenjamins.com/scorecard
    • The Vault: stackingbenjamins.com/vault


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    53 Min.
  • Bitcoin, Blockchain, and the Stuff Nobody Actually Explains (SB1832)

    Bitcoin, Blockchain, and the Stuff Nobody Actually Explains (SB1832)
    Apr 22 2026

    Blockchain. Stablecoins. Wallets. Staking. Halvings. If you've spent the last few years nodding confidently through crypto conversations while quietly hoping nobody asks a follow-up question -- this episode is for you. Retired anesthesiologist and trading veteran Joe Duarte went from crypto skeptic to informed pragmatist, and today he brings the plain-English breakdown that most crypto content assumes you don't need. No hype. No moon talk. Just the vocabulary, the mechanics, and the honest risks.

    What You'll Walk Away With

    • What blockchain actually is -- stripped of the jargon and explained in one sentence that actually sticks
    • The real difference between Bitcoin and Ethereum -- and why understanding those two unlocks everything else
    • What a stablecoin is, why it exists, and the one comparison that finally makes it click
    • The three crypto exchanges worth knowing -- and why starting with the big names isn't just convenient, it's genuinely safer
    • Hot wallets, cold wallets, and mobile wallets explained -- and which one makes the most sense if you're just getting started
    • What staking is, what mining is, and why neither one is your first move as a beginner
    • How crypto actually moves -- the liquidity connection most investors miss entirely
    • The tax trap that catches crypto beginners off guard -- and why your record keeping has to be airtight from day one
    • Why ETFs might be the smartest way for most Stackers to get crypto exposure without the operational headaches
    • The long-term care reality hiding in this episode -- and why 80% of people will eventually face a cost their current plan doesn't account for

    Why This Matters Now

    Whether you've been crypto-curious for years or you've actively avoided the conversation, the landscape has changed enough that staying completely uninformed carries its own risk. Regulation is arriving, major brokerages now offer access, and the vocabulary has leaked into mainstream financial planning. You don't have to become a believer -- but understanding what you're looking at puts you in a much better position to decide whether any of it belongs in your financial life.

    From the Basement

    Joe Duarte joins Joe and OG to translate the crypto dictionary for everyone who's been faking it at dinner parties for the last decade. In the headline segment, Joe and OG dig into a sobering new AARP report on long-term care costs -- and the conversation gets uncomfortably real about what most retirement plans are quietly missing. Doug arrives with trivia about the Bitcoin halving process, which turns out to have a name that required approximately zero creativity to invent. Whether the basement scoreboard reflects informed decision-making or something closer to Doug's personal net worth is a question best answered with your earbuds in.

    Resources Mentioned

    • Cryptocurrency 101 by Joe Duarte -- available wherever books are sold, with deals currently running on Amazon
    • Coinbase -- coinbase.com, recommended starting point for US-based crypto beginners
    • Kraken -- kraken.com, noted for advanced trading tools alongside beginner access
    • Binance -- binance.com, largest global exchange; noted history with US regulators worth researching
    • NFCI Index -- Chicago Fed's National Financial Conditions Index, useful for tracking crypto-correlated liquidity at chicagofed.org
    • Genworth Cost of Care Study -- annual long-term care cost data by state at genworth.com
    • AARP Long-Term Care Report -- linked in show notes at stackingbenjamins.com
    • Stacking Benjamins Scorecard -- stackingbenjamins.com/scorecard
    • Stacking Benjamins Vault -- stackingbenjamins.com/vault
    • Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com
    • Hegemony board game -- referenced by Joe post-show; details at hegemonyproject.com


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    1 Std. und 15 Min.
  • The Tax Triangle Most Investors Have Never Heard Of (SB1831)

    The Tax Triangle Most Investors Have Never Heard Of (SB1831)
    Apr 20 2026

    Most people think about investing in terms of what to buy. Joe Saul-Sehy, OG, and CFP Anna Allem argue the more important question is where you put it. This week they break down the three-bucket tax triangle that could save you thousands in retirement, plus answer listener questions on Trump accounts, UTMAs, and how to pull together a home down payment when your money is locked up in all the wrong places.

    In this episode:

    The difference between pre-tax, brokerage, and tax-free investing and why you need all three, what the new Trump account actually does and who it makes sense for, how to build a home down payment when your assets are tied up in retirement accounts, and why flexibility in your tax strategy matters as much as the investments themselves.

    Biggest takeaways:

    Draw a triangle. Label each corner pre-tax, brokerage, and tax-free. Then draw your buckets to scale based on where your money actually sits. If one bucket dwarfs the others, that's your problem to solve before you touch anything else.

    The Trump account is not a traditional IRA, despite what the website implies. Money goes in after tax, grows tax deferred, and comes out taxable. For most people with a 529 and an UTMA already in place, keep going with what you have.

    When your money is locked in retirement accounts and you need a down payment, the math has two sides. What does pulling it out cost you today in taxes and penalties, and what does it cost you in thirty years of lost compounding? Know both numbers before you decide.

    Resources mentioned:

    • Episode 1808 on help eliminating hospital bills (on navigating medical bills and hospital assistance programs)
    • The Stacking Benjamins scorecard: stackingbenjamins.com/scorecard
    • The Vault: stackingbenjamins.com/vault
    • Submit your question: stackingbenjamins.com/yelldownstairs


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    54 Min.
  • The Best Money Advice We Wish We Knew at 20 (Live from Texas A&M - Texarkana) SB1830

    The Best Money Advice We Wish We Knew at 20 (Live from Texas A&M - Texarkana) SB1830
    Apr 17 2026

    What would you ask about money if you had the mic?

    Live from Texas A&M Texarkana, Joe Saul-Sehy, Paula Pant, and financial educator Jay Davis take questions from students facing real-world money decisions—like choosing between passion and paycheck, avoiding lifestyle creep, investing safely, and building a financial future from scratch.

    If you're in your 20s—or wish you could do them over—this episode is packed with the advice we wish we knew earlier.

    Plus: Doug climbs into the rafters (again) for a trivia showdown you won’t forget.

    💡 What We Cover in Today’s Episode

    • Passion vs paycheck vs peace: How do you actually choose a career without regretting it later?
    • Why “follow your passion” might be terrible advice—and what to do instead
    • How to avoid lifestyle inflation when your income jumps
    • The easiest way to “hide money from yourself” (and why it works)
    • The real difference between 401(k)s, IRAs, stocks, and gold (finally explained clearly)
    • What “safe investing” actually means (hint: it depends on time)
    • The biggest money mistakes college students make—and how to avoid them
    • Why systems beat discipline every single time
    • Smart ways to manage student loans after graduation
    • The underrated power of an emergency fund (aka your freedom fund)
    • How networking—not your resume—can shape your financial future

    🧠 The Big Takeaways

    • You don’t need perfect discipline—you need better systems
    • Your first few years out of school can change everything financially
    • “Safe” depends on when you need the money
    • The earlier you start, the more your money works (hello, compounding)
    • Most people don’t fail from lack of knowledge—they fail from lack of action

    🎤 Special Guests

    • Paula Pant – Host of the Afford Anything Podcast
    • Jay Davis – Executive Director of Financial & Entrepreneurship Engagement, Texas A&M Texarkana
    • Thank you to Red River Credit Union for underwriting this live show!
    • FULL SHOW NOTES: https://stackingbenjamins.com/live-q-and-a-with-paula-pant-1830
    • Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201


    Enjoy!

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    1 Std. und 6 Min.