The Stacking Benjamins Show

Why "Doing It Yourself" With Money Is Costing You SB1896

Collaboration is celebrated everywhere else. Musicians collaborate. Athletes have training partners. Businesses merge their best ideas together. But mention teaming up on

Todd Havens: Why Most People Don't Have a Money Problem, They Have a Thinking Problem SB1895

Todd Havens spent decades dreaming of a net worth of zero, just breaking even felt like an impossible finish line. Then, in 2021, at the height of COVID, a doctor deliver

You're Doing Risk Tolerance Backwards SB1894

Every brokerage account asks the same question: how comfortable are you with a 20% decline? Are you conservative, moderate, or aggressive? Joe and OG argue that's exactly

Angelo Poli: Why Your Health Is a Financial Decision (SB1893)

This is a different kind of episode. No trivia, no headlines, just Joe and longtime health and wellness expert Angelo Poli having an honest, unscripted conversation about

The 5 Secrets of a Happier Retirement with Wes Moss (SB1892)

What actually makes for a happy retirement? Today, Joe sits down with retirement expert Wes Moss, author of The Retire Sooner Method, to explore the research behind Ameri

The Mental Trick That Makes Saving Money Effortless SB1891

Companies have gotten frighteningly good at removing friction from spending. One click, stored payment info, a box on your porch before you've even had time to regret the

How Many of These Ad Slogans Can You Still Name? (Paula Pant, Len Penzo, OG Play Along) SB1890

Everybody likes to believe they're too smart for marketing. Companies spend billions of dollars putting jingles and slogans in our heads anyway, and this episode puts tha

Mel Robbins: The Morning Habit That Rewires Your Brain SB1889

Before Mel Robbins became one of the most recognized names in personal development, she was $800,000 in debt, unemployed, and numbing the panic with bourbon most nights b

Your Financial Order of Operations: What to Fix First SB1888

There's a version of financial advice that lists fifty things you're supposed to be doing at once: build an emergency fund, pay off debt, invest, get life insurance, star

What to Teach Your Kids About Money, and When 1887

Every parent eventually asks the same question: what does my kid actually need to know about money, and when do I teach it? Today's roundtable brings together three genui

Tim Semro Answers Your Weirdest Estate Planning Questions SB1886

"Do I need a trust or just a will?" might be the single most common estate planning question there is, and estate attorney Tim Semro says most people are asking it backwa

The Four Psychological Tricks That Get You to Sign Anything (SB1885)

Nobody skips reading a contract because they're careless. Contract attorney Leo Mann spent 30 years writing the fine print that governs leases, car loans, job offers, and

When Is "Good Enough" Actually Good Enough With Money? SB1884

There's a version of financial responsibility that looks a lot like discipline but can quietly become something else: an inability to ever stop optimizing. Chasing 0.2% m

Len Penzo: The 18-Year Sandwich Survey That Predicts Recessions (SB1883)

Every year, Len Penzo prices out the exact same ten brown-bag sandwiches, using the exact same methodology, at the exact same time of year, and turns it into one of the m

Should You Max Out a 401(k) You Don't Even Like? SB1882

Three 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 "obviou

What a Bad Boss Is Actually Costing You (SB1881)

Most 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 Me

What to Do When Insurance Denies Your Claim (And Why They Count on You Giving Up) SB1880

It'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 ho

Jesse Mecham (YNAB Founder) On The One Question That Ends Money Anxiety For Good (SB1879)

There'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 trac

Your Mid-Year Tax Checkup: Fix Problems Before They Become April's Problem (SB1878)

Most 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 episod

Why Smart People Make Dumb Money Decisions SB1877

Three 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.