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The Stacking Benjamins Show

The Stacking Benjamins Show

By: Joe Saul-Sehy and Josh ‘OG’ Bannerman CFP
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Summary

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

© SB Podcast LLC | Gamut Podcast Network
Economics Personal Finance
Episodes
  • How to Save Your First $25,000 -- The Roadmap Most People Get Wrong (SB1838)
    May 6 2026

    Getting to your first $25,000 saved is harder than anything that comes after it. Not because the math is complicated -- because the habits aren't built yet, the fixed expenses are already set, and the standard advice about cutting small treats completely misses where the real leverage is. Scott Trench, VP of Operations at BiggerPockets and author of Set for Life, brings a roadmap that challenges almost everything you've heard about getting started -- and it begins with a decision most people aren't willing to make.

    What You'll Walk Away With

    • Why the first $25,000 is the hardest milestone -- and why cutting lattes and happy hours won't get you there
    • The three budget categories that actually matter -- and why they account for two thirds of what most people spend
    • Why saving your next $1,000 is more valuable than earning your next $1,000 -- and the tax math that proves it
    • The house hacking strategy that can eliminate your largest monthly expense entirely -- even if you never want to be a full-time landlord
    • Why stocks are less risky than bonds for long-term investors -- and the age-based argument Scott makes that most people miss
    • The counterintuitive case for spending more on fun -- once you've handled the big fixed expenses first
    • Why developing a specialty may actually be riskier than being adaptable -- and what that means for your career strategy
    • The retirement account trap that catches early savers off guard -- and when maxing out isn't the right first move
    • How to actually vet a financial advisor before handing over your money -- and why the problem is often as much the client as the advisor
    • Why international stocks belong in your portfolio even when they've underperformed -- and the rebalancing math that changes the picture

    Why This Matters Now

    This conversation was originally recorded years ago, but it was pulled from the vault for a reason: saving that first $25,000 feels harder today than it did then. Costs are higher, decisions feel riskier, and it's easier than ever to feel stuck before you even get started. The core framework Scott lays out hasn't changed -- and if anything, it applies more directly now than when it was first recorded.

    From the Basement

    Scott Trench joins Joe and OG to walk through the early chapters of Set for Life -- the ones that challenge conventional saving wisdom before getting into the real estate strategy BiggerPockets is known for. The headline segment takes on a Bloomberg piece about bad financial advisors and a lawsuit against American Funds, and OG gets considerably more animated than usual about both. Doug arrives with muni bond trivia that turns out to be exactly as straightforward as it sounds -- which is either reassuring or anticlimactic depending on your expectations.

    Resources Mentioned

    • Set for Life by Scott Trench -- biggerpockets.com/setforlife
    • The Truth About Money by Ric Edelman -- referenced by Joe as a foundational personal finance read
    • FINRA BrokerCheck -- finra.org/brokercheck; referenced for vetting financial advisors
    • Stacking Benjamins Scorecard -- stackingbenjamins.com/scorecard
    • Stacking Benjamins Vault -- stackingbenjamins.com/vault
    • Stacking Benjamins Community -- stackingbenjamins.com/basement


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    Show More Show Less
    1 hr and 6 mins
  • 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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    Show More Show Less
    1 hr and 3 mins
  • 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.
    Show More Show Less
    57 mins
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