The Stacking Benjamins Show

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

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 fin

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The podcast currently has 2,202 episodes available.

Best of The Stacking Benjamins Show

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Number 1: 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, 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 up so well it earned a spot in our Greatest Hits lineup unchanged. What You'll Walk Away WithA simple four-quadrant framework for seeing your entire financial picture in one place, instead of overwhelming yourself with fifty scattered tasksWhy cash flow and risk management should almost always come before any long-term goal-setting, no matter how exciting the goals areThe real difference between a strict budget and an "anti-budget," and how to know which one your situation actually calls forWhy debt consolidation can quietly make things worse if the underlying behavior never changesA clear-eyed look at which insurance actually matters most early in your financial life, and which ones get overhypedWhy starting with your tax strategy or investment picks first is almost always backwards, and what should come before itThe blunt case against co-signing a loan for a family member, no matter how good the reason soundsWhy This Matters Now The instinct to fix everything at once usually backfires, not because the individual advice is wrong, but because doing five things halfway rarely beats doing one thing completely. A clear order of operations replaces that scattered, everything-at-once anxiety with a simple next step, and that clarity alone tends to build more momentum than any single tactic. Whether you're just starting to get organized or you've been meaning to revisit your plan for a while, knowing what actually comes first changes everything that follows. From the Basement A TikTok "hack" involving sneaking into a hotel breakfast buffet to save on groceries becomes the day's cautionary tale, alongside a genuinely unhinged story about an office keg that taught an entire WeWork floor a hard lesson about unlimited free beer. Resources MentionedStacking Benjamins Field Kit — the all-in-one net worth and budgeting tool referenced in the updated introThe 201 Newsletter — deeper dives on topics covered in the show, written by Kevin Bailey See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
August 24, 20261h 5min
Number 2: 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 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. What You'll Walk Away WithWhy "trust versus will" is the wrong question, and the three-column framework that actually determines what you needWhat a lady bird deed is, when it makes sense, and the family conflict it can quietly set up down the roadThe tax detail buried in gifting property early that can cost your heirs tens of thousands of dollars they didn't expectWhy naming a power of attorney without having an honest conversation first is one of the most common and costly mistakes families makeThe five-year Medicaid look-back rule explained clearly, including what happens if you don't quite make it to five yearsHow debt actually works after someone dies, including a real statute of limitations window most people don't know existsA special needs trust structuring tip that can protect a family member's government benefits without giving up their inheritanceWhy This Matters Now Estate planning tends to get pushed to "someday" because it feels complicated, uncomfortable, or like it only matters once you're wealthy. But the actual decisions, who has power of attorney, how property transfers, what happens if a parent needs long-term care, apply to nearly every family, regardless of net worth. Getting the structure right isn't about predicting the future perfectly. It's about making sure the people you love aren't left guessing, fighting, or losing money to easily avoidable mistakes during an already difficult time. From the Basement A birthday trivia detour into the surprising origin of the Nobel Prize reveals it was born from a very specific kind of reputation crisis, proof that it's never too late to actively shape how you'll be remembered. Resources MentionedYour Money, Your Way by Tim Semro — Tim's book on estate planning, free to downloadSemro Henry Ltd. — Tim's estate planning law firmStacking Benjamins Field Kit — the all-in-one financial organization tool See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
August 19, 202655min
Number 3: 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 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 WithWhy waiting until kids are "old enough to understand the math" is one of the most common mistakes parents makeA simple age-by-age breakdown of what to teach, from age six all the way through eighteenWhether you should tell your kids exactly how much you earn, and what to say instead if you'd rather notWhy letting kids make small, affordable money mistakes now protects them from much bigger ones laterHow to talk to kids about in-game currencies and microtransactions in a way that actually sticksA refreshingly simple way to build an allowance system that teaches real financial judgment, not just chore complianceWhy you don't need to be great with money yourself to teach your kids well, and what actually matters more than expertiseWhy This Matters Now It's easy to feel unqualified to teach your kids about money, especially if your own financial journey has had plenty of stumbles. But the goal was never to have all the answers. It's to normalize talking about money at home, model good decision-making out loud, and let kids practice with small stakes before the stakes get real. A little structure around when to introduce which concepts takes the guesswork out of a subject most parents already feel behind on, and turns it into something manageable, even fun. From the Basement A special exhibition round of trivia brings together three guest contestants for a genuinely close guessing game on the current going rate from the Tooth Fairy, complete with inflation commentary that would make any economist proud. Resources MentionedFollow the Money by Alaina Trivax — Alaina's new activity-based book teaching kids about moneyLet's Make It Grow — Alaina's platform helping parents teach financial literacyGifting Sense — Karen Holland's nonprofit teaching kids mindful spending, including the "Spending Ed" programEasy Peasy Finance — Rishi Vamdatt's YouTube channel and book series, including the new release Easy Peasy Stocks See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
August 21, 20261h 14min
Number 4: 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 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 well beyond feel-good advice. This episode originally aired in 2021 and earned its spot in our Greatest Hits lineup because the core idea hasn't aged a day. What You'll Walk Away WithThe five-second rule Mel used to physically interrupt anxiety and get out of bed during her lowest financial pointWhy knowing what to do with your money is almost never the real obstacle, and what actually isThe surprising research linking high-fives among NBA teams to which teams went on to win championshipsWhy so many people feel resistance instead of relief the first time they try this exercise, and what that resistance is actually telling youThe neuroscience behind why a simple physical gesture can interrupt a negative thought spiral more effectively than positive self-talkWhy self-worth tied to a bank balance, a job title, or a number on a scale tends to collapse the moment things go wrongA genuinely surprising story about grief, intuition, and a decision that changed the direction of Mel's entire familyWhy This Matters Now You probably already know several things you should be doing with your money right now. That's rarely the hard part. The hard part is closing the gap between knowing and doing, especially in moments of stress, shame, or overwhelm, exactly the moments financial setbacks tend to create. Building a habit of small, immediate self-support, showing up for yourself before you've accomplished anything, turns out to be one of the most overlooked tools for actually following through on the financial changes you already know you need to make. From the Basement A headline segment on modern, lower-fee annuities gets a healthy dose of skepticism, and a TikTok "wealth hack" involving margin loans gets thoroughly, hilariously debunked, a good reminder that not everything that sounds clever on social media survives contact with how markets actually work. Resources MentionedThe High 5 Habit by Mel Robbins — Mel's book on the science-backed daily practiceStacking Benjamins Field Kit — the all-in-one financial organization tool referenced in the updated intro See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
August 26, 20261h 11min
Number 5: 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 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 WithThe four psychological traps, stacked together on purpose, that get otherwise careful people to sign without readingWhy the phrase "this is standard" should be one of the biggest red flags in any negotiationA green flag, yellow flag, red flag rundown of common contract moments, from blank spaces to rush deadlines to page-by-page initialsThe hidden clause in shared leases that can leave one person legally responsible for an entire group's unpaid rentWhy the number on the front page of a lease or job offer is often just marketing, and where the real total actually livesThe critical difference between an employment offer letter and the actual employment agreement, and why only one of them is legally bindingWhy severance is almost always more negotiable than employers make it seem, and the two questions worth asking about any financial product before you commitWhy This Matters Now Every adult signs dozens of contracts over a lifetime, apartment leases, car loans, job offers, gym memberships, and the fine print in most of them is written to be skimmed, not read. That's not an accident, and it's not really about intelligence or diligence either. It's about recognizing the exact moments you're being nudged to move fast, and knowing which few sentences in a stack of paperwork actually matter. A little contract literacy doesn't just protect your money, it gives you real leverage the next time someone slides a stack of paper across the table and says, "just sign here." From the Basement A headline about Pepsi's infamous 1996 fighter jet promotion becomes the day's trivia detour, proving that even the biggest brands occasionally get burned by their own fine print, right alongside the rest of us. Resources MentionedDon't Sign That by Leo Mann — Leo's #1 bestselling guide to consumer contractsThe Contract Literacy Movement — Leo's initiative teaching everyday people to read what they signStacking Benjamins Field Kit — the all-in-one budgeting, credit monitoring, and financial tracking toolStacko Financial Action Month board — the interactive game with a money move for each square See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
August 17, 20261h 15min