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The Stacking Benjamins Show has produced 2,881 episodes. 638 of those episodes have been sponsored by 182 companies. We last recorded an episode on Aug 10, 2026.
Latest Episodes
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Should You Max Out a 401(k) You Don't Even Like? SB1882
Aug 10, 2026Three Stackers call into the basement today with three very different problems, but they all boil down to the same uncomfortable question: what do you do when the "obviously right" financial move doesn't feel right? A generous employer match paired with fund choices you're not thrilled about. A tax bracket so low it seems wasteful not to convert. A life that just took a turn nobody expected, and a whole new set of financial tools nobody teaches you about until you need them. Joe, OG, and Anna...
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What a Bad Boss Is Actually Costing You (SB1881)
Aug 7, 2026Most people measure a bad boss in bad days: the meeting that went sideways, the credit that got stolen, the comment that stung longer than it should have. Money Mentor Mel Abraham, along with Paula Pant and the crew, argues that's the wrong unit of measurement entirely. A toxic work situation has a real, compounding financial cost, in stalled raises, atrophied skills, drained energy, and years quietly lost to a job that was never going to get better. Today's episode puts a number on it, and...
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What to Do When Insurance Denies Your Claim (And Why They Count on You Giving Up) SB1880
Aug 6, 2026It's easy to walk out of a rushed appointment, an unexplained bill, or a denied claim and quietly blame the person in the white coat. Doc G (Doctor Jordan Grumet), the hospice physician and longtime Stacking Benjamins favorite, argues that's exactly the wrong target, and that the confusion isn't an accident. Somewhere between the insurance company, the pharmaceutical company, the private equity firm, and the electronic records system, a lot of people are getting paid, and the two groups...
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Jesse Mecham (YNAB Founder) On The One Question That Ends Money Anxiety For Good (SB1879)
Aug 5, 2026There's a strange thing that happens to a lot of people as their income grows: the anxiety doesn't go away, it just changes shape. More money, more accounts, more to track, and somehow the same low hum of worry every time a bill comes due. Jesse Mecham, founder of YNAB and one of the most trusted voices in budgeting, has spent over two decades helping people fix that, and his conclusion isn't a better spreadsheet or a stricter budget. It's a single question, one that sounds almost too simple...
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Your Mid-Year Tax Checkup: Fix Problems Before They Become April's Problem (SB1878)
Aug 3, 2026Most people only think about taxes twice a year: while filing, and while dreading filing next time. That gap is exactly where expensive surprises are born. Today's episode is a genuine mid-year tax tune-up, the kind of checkup that takes maybe twenty minutes and can quietly save you from an ugly bill, an unexpected penalty, or a refund that wasn't actually a win. No jargon-heavy lecture, just a clear walkthrough of what to check right now while there's still time to fix it.What You'll Walk...
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Why Smart People Make Dumb Money Decisions SB1877
Jul 31, 2026Three genuinely sharp financial minds sit down today and, one by one, admit to the same kind of dumb money moves everyone else makes. Not because they didn't know better. Because knowing better and doing better turn out to be two completely different skills, and your brain is very good at making bad ideas feel reasonable in the moment. This episode isn't about learning new investment tactics. It's about learning to recognize the exact moment your own mind starts working against you, and what...
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Why Your Homeowners Insurance Bill Keeps Going Up (And What to Do About It) Special Episode SB1876
Jul 30, 2026Homeowners insurance prices are up a whopping 24% since 2022. One in seven homeowners now has no insurance at all. In some parts of the country, companies aren't just raising rates -- they're refusing to write policies. Bob Litterman co-created the Black-Litterman model that the financial industry still uses to price risk, spent 23 years running risk at Goldman Sachs, and now chairs the Coalition for an Insurable Future. He joins Joe and OG on a special Thursday episode to explain what's...
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Meet the Family That Quietly Controls Your Retirement Money (SB1875)
Jul 29, 2026Odds are good that part of your paycheck disappears into an account with the Fidelity name on it every two weeks. Almost nobody stops to ask who's actually on the other end of that relationship. The answer isn't a faceless Wall Street institution, it's one family that has quietly controlled a $15 trillion company for three generations, through boardroom near-mutinies, a succession fight that almost ended in the company being sold, and enough family drama to fill a book. It did, actually. Wall...
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The One Financial Conversation People Avoid (Plus a Discussion about Stress and Money) SB1874
Jul 28, 2026There are three words that quietly end up costing more than almost any bad investment: "he handles it." Not because delegating is wrong, but because somewhere between division of labor and total disengagement, a line gets crossed that most couples never notice until a crisis forces them to. This episode is about that line, and about the less obvious ways money stress shows up when it's not just a spreadsheet problem, it's a physical one. Jill Schlesinger and Kristy Talorico both join the...
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Everything You Actually Need to Know About Social Security Right Now (SB1873)
Jul 27, 2026There's a new bill in Washington that sounds like a fix but is really just a promise to eventually have a debate about one. That's not why this episode matters. What matters is that Social Security is suddenly everywhere in the headlines, and if you've been putting off understanding how your own claiming decision actually works, that's a gap that gets more expensive the longer it sits. This episode is the one to finally close it. No single mistake, no one hot take, just a real walkthrough of...
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