The Stacking Benjamins Show

Thinking in Bets: Annie Duke on Making Smarter Decisions When You Don't Have All the Facts - Greatest Hits! (SB1837)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 See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Index Investing 101: Stop Picking Funds and Start Building the Mix That Actually Works (SB1834)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 With • Why the real argument for index investing isn't that nobody beats the market -- it's that you can't predict who will do it next • The crockpot principle of index investing -- and why the self-cleaning oven analogy might be even better • Why 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 run • The $100,000 turning point: what changes about your investment strategy when the portfolio gets big enough to get scientific • The first two additions most Stackers should consider beyond their core index -- and why OG would actually add more than two • Why mixing index funds from different companies can quietly undermine your diversification without you ever knowing it • How to replace the word "index" with "list" to instantly identify whether a product is actually doing what you think it is • The buffered ETFs, factor ETFs, and active ETFs that call themselves indexes -- and why most Stackers should walk right past them • Why you're not racing against the index -- you're on a road trip -- and what that shift in framing changes about every investing decision • The season one recap from OG and Anna's financial planning basics series -- plus the free workbook that ties all seven episodes together Why This Matters Now In 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 Basement Joe 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 Mentioned The Simple Path to Wealth by JL Collins • -- referenced as the foundational text for beginner index investors • Prior 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 within JP Morgan Guide to the Markets • -- referenced in prior episode; available at jpmorgan.com • Stacking Benjamins Basics Guide -- free seven-episode workbook at stackingbenjamins.com/basicsguide • Stacking Benjamins Newsletter (The 201) -- weekly investing hot takes from Kevin Bailey at stackingbenjamins.com/201 • Stacking Benjamins Vault -- stackingbenjamins.com/vault • Stacking Benjamins Meetups -- 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.

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