The Stacking Benjamins Show

Most of us are optimizing a number, whether it’s a retirement balance or a job title, and almost never stop to ask what it’s for. Wharton economist Corinne Low measures how people really trade time, money, and love, and she has a short exercise that shows how little of your ideal life depends on that number. Joe Saul-Sehy and guest co-host Anna Allem, CFP, put her ideas to work on careers, partnerships, and the awkward conversations in between. You’ll hear why a house can act as insurance in a marriage, why your job won’t love you back...

Some of the best money moves of the year come with a deadline most people never notice. A student loan rate can drop by a full percentage point with one setup step. A window may be open to move retirement money with little or no tax. A gap in your income protection can sit unnoticed until a claim gets denied. Joe Saul-Sehy and guest co-host Anna Allem, CFP, sort the urgent from the merely interesting, using a caller’s real insurance dilemma, a family college decision, and a ringside look at the market’s worst Mondays. It takes a free...

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Ask a room of young adults what they want most from life and about eight in ten will say “get rich.” The longest scientific study of adult life, now following the children of its original participants, found something different about what pays off. Dr. Robert Waldinger leads the Harvard Study of Adult Development, and he explains why one kind of spending keeps making people happier long after a flashy purchase fades, why career achievement doesn’t predict a good life, and the habit he now treats the way he treats the gym. Along the way come a rundown of what S...

Most people check their 401(k) the way they check a gas gauge: a glance, a shrug, and back on the road. Joe and OG pop the hood on the whole engine and work through 25 fixes, from a two-minute change to a phone call that could cut real money from your fees. The surprise is how many of them have nothing to do with your employer’s plan. A mediocre 401(k) can still do its job if the rest of your accounts pick up the slack, and the bar for “good enough” is lower than the internet makes it sound.

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The Fed just raised rates for the first time in more than three years, and the markets barely flinched. Your mortgage, your CDs, and your next car payment may feel it differently than the headlines suggest. The panel breaks down what a quarter point actually changes, then turns to two newer ways of borrowing against your future self: buy now, pay later apps that run almost entirely on debit cards, and a prediction market that wants Congress to let you borrow money to bet. One episode, three headlines, and one thread running through all of them.

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Credit card companies are getting smarter about one thing: making an $800 annual fee feel like a steal. Joe and OG open the vault on how the points-and-perks game actually works, why "free" subscriptions and dining credits aren't really free, and the one simple piece of math that tells you whether a point is worth more than cash. Doug plays referee in a live round of Points, Cash, or Pass, and it turns out his instinct to keep one boring card in his wallet might be the smartest strategy in the room.

What You'll Walk Away With

Bigger returns. Guaranteed income for life. Retiring five years early. Every one of these sounds like an obvious yes, until you see the invoice that comes with it. Joe puts Doc G, OG, and Jesse Cramer through a rapid-fire "in or out" game: he pitches five genuinely appealing financial ideas, and each of them has to decide whether they'd actually take the deal, and name the worst realistic thing that could go wrong if they did.

What You'll Walk Away With

A $12,000 emergency room bill for popping a dislocated shoulder back into place. A car-buying strategy that saved one family $4,000 with a single text message. A college athlete's first taste of NIL money and the tax questions that come with it. Joe and OG spend today answering real questions from real Stackers, the kind of specific, practical situations that don't always fit neatly into a textbook, but come up constantly in real life.

What You'll Walk Away With

Some financial strategies aren't bad, they're just wildly oversold to people they were never built for. Joe and OG walk through five genuinely legitimate, sometimes powerful tools, cash value life insurance, municipal bonds, qualified longevity annuity contracts, net unrealized appreciation, and complex charitable trusts, and draw a clear line between the tiny slice of people these actually help and the much larger crowd who gets pitched them anyway. If you've ever had someone offer you a "special" financial strategy and wondered whether it was genius or a sales tactic, this episode gives you the framework to tell the difference.<...

Live from FinCon, Joe sits down with historian and bestselling author Joseph Moore, Paula Pant, and Jesse Cramer to talk about what's actually keeping people up at night: AI concentration in the stock market, inflation anxiety that won't fully fade, interest rates that feel "stuck," and a housing market that seems rigged against newcomers. The twist is that almost none of it is new. From a Scottish con man's fake country bonds to the 1830s stock that was over 30% of the entire market, to a refrigerator boom that happened during the Great Depression, this conversation uses 300 years of financial...

In April 2025, the bond market did something the stock market couldn't: it made a sitting president reverse course within days. Financial Times journalist Robin Wigglesworth, author of the new book A Fabulous Debt, joins Joe and OG to explain why bonds, dismissed for centuries as the dull corner of finance, are actually the bedrock everything else sits on. From a murdered medieval ruler in Venice to a Scottish con man who sold bonds for a country that didn't exist to the hedge fund collapse that nearly took down the global financial system, this is 900 years of history explaining exactly...

"How do I know it's time to fire my advisor?" That question came up over and over at a recent retreat, enough that Joe knew it needed its own episode. Today he and OG walk through five real, specific red flags, not vague warnings about fees, but concrete signs that your advisor might be coasting, out of their depth, or simply not built for where your life is headed. If you've ever sat in a meeting with your advisor and wondered whether you're getting real value or just really good small talk, this one's for you.

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You've done everything right. Emergency fund, employer match, maxed-out retirement account, boring diversified index funds quietly compounding in the background. And now some part of you is wondering: is there a next level? Financial educator Brian Feroldi joins Paula Pant and Jesse Cramer for a genuinely useful gut-check on whether picking individual stocks is a smart next step, a fun hobby, or a trap dressed up as ambition, and how to tell the difference before you put real money on the line.

What You'll Walk Away With

The traditional life plan, learn, work for four decades straight, retire once and for all, was built for a much shorter life than many of us are actually going to live. Lynda Gratton, London Business School professor and bestselling author of The 100-Year Life, has spent years studying what happens when that old blueprint stops matching reality. Her answer isn't a bigger retirement number. It's a completely different way of thinking about how work, rest, learning, and relationships fit together across a much longer stretch of time, and what that means for how you actually fund it.

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Someone with half a million dollars confidently retires and thrives. Someone else with a full million dollars runs into trouble within a few years. The dollar amount alone never tells the whole story, and today's episode proves it with three real scenarios side by side. Joe and OG walk through exactly what changes the math: your age, whether Social Security has kicked in yet, how much of your spending is already covered by guaranteed income, and how many years that portfolio actually needs to stretch.

What You'll Walk Away With

Collaboration is celebrated everywhere else. Musicians collaborate. Athletes have training partners. Businesses merge their best ideas together. But mention teaming up on your finances, and suddenly it sounds suspicious, like you're doing something wrong. Joe sits down with Paula Pant, Jesse Cramer, and OG to ask why personal finance is the one area where going it alone gets treated as a virtue, and what exactly gets left on the table when nobody's allowed to help.

What You'll Walk Away With

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 delivered news that would reframe everything: incurable blood cancer, tumors too numerous to count. What follows is one of the most honest, wide-ranging conversations this show has had about money, mortality, and the difference between being rich and actually being wealthy. Todd is now in remission, a self-made millionaire, and the author of a book built entirely around one idea: the biggest obstacle to financial security usually isn't a spreadsheet...

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 the wrong place to start, and it's why so many people panic-sell at the worst possible moment. The real question isn't how you feel about risk. It's what rate of return your actual goals require, and whether you can stomach the volatility that comes with getting there. Once you flip the order, risk tolerance stops being a personality quiz and becomes a math problem you can actually solve.

What You'll Walk...

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 what happened when a training injury, a missed diagnosis, and months of frustration sent Joe into a spiral he didn't see coming. It's a personal story, but the reason it belongs on a money show is simple: your ability to earn, think clearly, and actually enjoy what you've built depends on your health just as much as it depends on your portfolio.

What You'll Walk Away With

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 America’s happiest retirees. Wes explains why money is only part of the equation, how community and “super activities” give retirement purpose, why eliminating debt can create more freedom, and how a clear retirement plan can help reduce the fear of running out of money.

Then Joe and OG tackle one of retirement’s most popular investing strategies: living off dividends so you never have to sell your investments. They break do...

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 purchase. Today's episode flips that same idea around: what if you engineered your own financial life the same way, making good decisions the path of least resistance and bad decisions just annoying enough to make you pause? Joe and OG close out Financial Action Month with a genuinely useful framework for building systems that work even on the days your willpower doesn't show up.

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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 that theory to the test. Paula Pant, Len Penzo, and OG face off in a rapid-fire game: Doug reads a slightly modified version of a famous advertising slogan, and they have to name the brand. What follows is a genuinely fun, surprisingly competitive round that proves just how deep this stuff sits in all of our brains, whether we like it or not. This one's a Greatest Hits favorite, originally recorded back in 2020...

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 by six o'clock. She knew exactly what she needed to do to climb out. Knowing wasn't the problem. Taking the first step was. That gap, between knowing and doing, is exactly what this conversation is about, and it's why Mel's simplest tool, a five-second countdown and a high five in the mirror, has been validated by neuroscience, adopted by veterans' organizations treating PTSD, and linked to real behavior change in ways that go...

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, start a Roth, build an estate plan. All true, all important, and all completely useless without one missing piece: the order. Joe and OG walk through the exact sequence for figuring out what to tackle first, second, and third, so instead of freezing under the weight of everything, you know precisely where to start today. This one's a Stacking Benjamins classic, originally recorded a few years back, and the framework holds...

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 genuinely different perspectives, financial educator Karen Holland of Gifting Sense, middle school teacher and author Alaina Trivax, and Rishi Vamdatt, the now-college-bound creator behind Easy Peasy Finance who started teaching kids about money at age eight. Together they build a real, age-by-age roadmap, from swiping a credit card at six years old to filing taxes for the first time at eighteen.

What You'll Walk Away With

"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 backwards. The real question isn't trust versus will, it's how do you avoid probate, and a trust is just one of several ways to get there. Tim returns to answer a full mailbag of real Stacker questions, covering everything from a $200,000 mistake buried in a lady bird deed to the exact reason so many families accidentally disqualify a parent from Medicaid.

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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 gym memberships, and he says the reason smart people sign blind isn't laziness at all. It's four specific psychological pressures, engineered on purpose, stacked on top of each other in the exact moment you're handed the paperwork. Today he walks through exactly how those tricks work, and more importantly, how to spot them before you sign away something you'll regret.

What You'll Walk Away With

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% more interest. Driving fifteen minutes out of the way for cheaper gas. Budgeting so tightly that a $5 bottle of multivitamins feels like a crisis. Wealthy Kids Club founder Maya Corbic joins Carol Ann Desiderio and Jesse Cramer for a genuinely fun debate about where the line actually sits, and what over-optimizing quietly costs when nobody's counting it.

What You'll Walk Away With

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 most oddly reliable inflation trackers around. This year the numbers are ugly: double-digit jumps across the board, an 80% spike in one ingredient alone, and a genuinely surprising twist involving the humble bologna sandwich that Len says has quietly tracked economic downturns for nearly two decades. Then, a headline that should make every family pause: how one daughter used a single signed document to quietly drain nearly a million...

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 "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 Allen tackle all three with real, usable answers.

What You'll...

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 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 gives you the exact steps to build your way out.

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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 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 actually providing and receiving care are left holding the bag. Here's the good news: almost nobody appeals a denial, and...

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 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 to matter, until you actually try to answer it.

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 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 Away With

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. 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 to do about it before it costs you.

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Homeowners 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 actually happening, why it's not going to stop, and what you can do about it right now.

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Odds 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 Street Journal reporter Justin Baer spent years uncovering it, and today he brings the whole story down...

There 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 show, and each brings something you didn't know you needed to hear.

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