PodcastsBusinessThe Stacking Benjamins Show

The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
The Stacking Benjamins Show
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2837 episodes

  • The Stacking Benjamins Show

    How to Save Your First $25,000 -- The Roadmap Most People Get Wrong (SB1838)

    2026-05-06 | 1h 6 mins.
    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

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
  • The Stacking Benjamins Show

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

    2026-05-04 | 1h 2 mins.
    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.
  • The Stacking Benjamins Show

    Invest Like the 1%? What to Steal, What to Scale, and What to Skip (SB1836)

    2026-05-01 | 56 mins.
    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 With
    Why 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 try
    The tax strategy obsession that the wealthy genuinely use -- and why Jesse ranks it seventh on his list of financial priorities, not first
    What 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 anyway
    The 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 it
    Why 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 returns
    The leverage conversation that exposes a contradiction hiding in plain sight for every real estate investor
    Why 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 level
    The 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 looks
    Why rich habits and "what the 1% does" are two completely different things -- and which one is actually worth chasing
    Why This Matters Now
    In 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 Basement
    Joe, 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 Mentioned
    Finance Rox -- Roxanne Duckels on YouTube and Instagram @FinanceROX
    Personal Finance for Long-Term Investors -- Jesse Cramer's podcast, wherever you listen
    Stacking Benjamins Newsletter (The 201) -- recent issue: brokerage vs. UTMA/UGMA vs. Trump accounts for kids; stackingbenjamins.com/201
    Stacking Benjamins Vault -- stackingbenjamins.com/vault
    Stacking Benjamins Community -- stackingbenjamins.com/basement
    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.
  • The Stacking Benjamins Show

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

    2026-04-29 | 1h 3 mins.
    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

    See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
  • The Stacking Benjamins Show

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

    2026-04-29 | 1h 6 mins.
    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. Haley 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

    FULL SHOW NOTES: https://stackingbenjamins.com/interview-with-mrs-dow-jones-1835
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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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