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Joe Saul-Sehy and Josh ‘OG’ Bannerman

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

The Stacking Benjamins Show

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 Away With

 • Why "risk" and "volatility" are two completely different things, and confusing them leads to bad investing decisions
 • The real order of operations for building a portfolio: goal first, required return second, risk tolerance last
 • How standard deviation can turn scary market swings into something you expected all along, instead of something that panics you
 • Why concentration risk quietly builds up in portfolios, even for people who think they're diversified
 • A genuinely surprising take on why "getting more conservative as you age" often doesn't make sense, once you think in decades instead of birthdays
 • Real answers to listener questions on emergency fund sizing, late-start Roth conversions, disability insurance coverage, and whether the 4% retirement rule still holds up

Why This Matters Now

A risk tolerance quiz can't tell you what you actually need your money to do. It just measures a feeling in the moment, and feelings change the second the market gets scary, which is exactly when a plan built on feelings falls apart. Building your investment strategy around your actual goals and time horizon, instead of a gut reaction to hypothetical losses, gives you something sturdier to hold onto when the inevitable rough year arrives. That's the difference between panic-selling at the bottom and staying the course long enough to actually reach the life you're investing for.

From the Basement

A Labor Day trivia detour into the 1916 origins of workers' compensation somehow spirals into a bit about an "employee named Al" being replaced by AI, which is either brilliant wordplay or a sign the basement crew needs a vacation. Possibly both.

Resources Mentioned

Stacking Benjamins Field Kit • — the all-in-one budgeting and financial tracking tool
Yell Down the Stairs • — submit a question for a future OG and Anna episode

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

You're Doing Risk Tolerance Backwards SB1894

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

 • Why a setback in one area of your health or life can quietly spiral into others, and the exact moment that turnaround has to happen
 • The science behind why doing "one thing" well beats trying to overhaul everything at once
 • Why having someone else to be accountable to changes follow-through far more than willpower alone
 • A candid explanation of why almost nobody follows through on "I'll think about it and get back to you," and what to do instead
 • Why acting early in the day and early in the week measurably increases your odds of sticking with a health goal
 • How physical health directly affects financial outcomes, through energy, focus, decision-making, and the years you get to actually enjoy what you've saved

Why This Matters Now

It's tempting to treat health and money as two completely separate categories of adulting. But the connection runs deeper than most people realize: poor sleep, low energy, and physical pain make it harder to think clearly, work efficiently, or make good financial decisions. And the whole point of building financial security is having the health to actually enjoy it, time with family, travel, the ability to do the things you're saving for. Taking care of one without the other only gets you halfway to the life you're actually working toward.

Resources Mentioned

MetPro • — Angelo Poli's concierge nutrition, fitness, and lifestyle coaching program, free session for Stacking Benjamins listeners

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

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

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 down why dividends feel so appealing, where the strategy can fall short, and why building your retirement income plan around your goals may matter more than chasing a particular yield. Plus, Doug celebrates the anniversary of the ATM with some cash-dispensing trivia.

Resources mentioned

Wes MossThe Retire Sooner Method: The 5 Secrets Behind America’s Happiest and Unhappiest RetireesYou Can Retire Sooner Than You ThinkRetirees Love Dividends, but the Stock Market Surge Is Making Them Think Again — The Wall Street JournalField Kit FinanceThe 201 newsletter — stackingbenjamins.com/201Field Kit Finance webinars: Sign up for The 201 to get the full schedule.The Clark Howard ShowFinConDana AnspachBen CarlsonAttorney Tim Semro’s recent Stacking Benjamins appearance

FULL SHOW NOTES: https://www.stackingbenjamins.com/wes-moss-retire-sooner-method-1892/

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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

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

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.

What You'll Walk Away With

 • Why discipline isn't a personality trait, it's a system you build once instead of a decision you make every day
 • A simple "make it easy or make it hard" test you can apply to any financial habit, from retirement savings to late-night online shopping
 • Why automating your savings rate removes the single biggest source of decision fatigue in a financial plan
 • A smarter way to handle windfalls and bonuses, deciding your split between saving, debt, and fun once a year instead of every single time
 • Why canceling a subscription is deliberately made difficult, and the workaround that neutralizes it
 • A four-step "financial action ladder" for turning financial knowledge into permanent, lasting habits
 • Why waiting a day before a big purchase, and other small friction points, can save you from regret without requiring any extra willpower

Why This Matters Now

Knowing what to do with your money has never really been the hard part. The hard part is doing it consistently, especially when life gets busy, stressful, or just plain boring. Building your environment so the smart choice is also the easy choice takes the daily grind of willpower out of the equation entirely. That's not a lack of discipline, it's actually the most disciplined move available: deciding once, automating it, and letting the system do the work every day after that.

From the Basement

A goofy but genuinely fun "make it easy or make it hard" game plays out across everything from emergency funds to concert tickets, and a National Trail Mix Day detour delivers exactly the kind of nonsense only this show could make delightful.

Resources Mentioned

Stacko Financial Action Month board • — the interactive game with a money move for each square
Stacking Benjamins Field Kit • — the all-in-one financial organization and subscription-canceling tool
Profit First by Mike Michalowicz • — the book referenced on flipping the save-then-spend default

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

The Mental Trick That Makes Saving Money Effortless SB1891

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, and the game holds up exactly as well today.

What You'll Walk Away With

 • A fast-paced, genuinely fun game you can replay in your own head (or with friends on a road trip) testing how many classic slogans you actually remember
 • A real discussion on how much advertising quietly shapes what we believe is smart to buy, invest in, or trust with our money
 • A candid conversation about pieces of financial advice that used to be gospel and don't hold up anymore, including homeownership as an automatic wealth-builder and the old "100,000 miles and it's time for a new car" rule
 • A memorable real-world story about how deeply brand loyalty can override even a clearly better financial decision
 • A reminder that good financial advice isn't about memorizing fixed rules, it's about regularly checking whether those rules still fit your actual life

Why This Matters Now

It's easy to assume you make financial decisions purely on logic. But brand recognition, catchy slogans, and decades of repeated marketing messages shape more of our buying and money decisions than most of us would like to admit. Recognizing that influence doesn't mean living in constant suspicion of every ad you see. It means occasionally asking whether a belief about money, homeownership, cars, insurance, college, is something you actually decided, or something you absorbed because you heard it enough times to assume it was true.

From the Basement

A wildly competitive slogan showdown ends with a last-to-first comeback, plus a genuinely great story about a five-year-old spotting a McDonald's from the top of the Empire State Building at the exact wrong (or right) moment.

Resources Mentioned

Afford Anything podcast • — Paula Pant's show
LenPenzo.com • — Len Penzo's site, including his sister blog, The Persistent Itch
Stacking 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.

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

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 With

 • The five-second rule Mel used to physically interrupt anxiety and get out of bed during her lowest financial point
 • Why knowing what to do with your money is almost never the real obstacle, and what actually is
 • The surprising research linking high-fives among NBA teams to which teams went on to win championships
 • Why so many people feel resistance instead of relief the first time they try this exercise, and what that resistance is actually telling you
 • The neuroscience behind why a simple physical gesture can interrupt a negative thought spiral more effectively than positive self-talk
 • Why self-worth tied to a bank balance, a job title, or a number on a scale tends to collapse the moment things go wrong
 • A genuinely surprising story about grief, intuition, and a decision that changed the direction of Mel's entire family

Why 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 Mentioned

The High 5 Habit by Mel Robbins • — Mel's book on the science-backed daily practice
Stacking 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.

Mel Robbins: The Morning Habit That Rewires Your Brain SB1889

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 With

 • A simple four-quadrant framework for seeing your entire financial picture in one place, instead of overwhelming yourself with fifty scattered tasks
 • Why cash flow and risk management should almost always come before any long-term goal-setting, no matter how exciting the goals are
 • The real difference between a strict budget and an "anti-budget," and how to know which one your situation actually calls for
 • Why debt consolidation can quietly make things worse if the underlying behavior never changes
 • A clear-eyed look at which insurance actually matters most early in your financial life, and which ones get overhyped
 • Why starting with your tax strategy or investment picks first is almost always backwards, and what should come before it
 • The blunt case against co-signing a loan for a family member, no matter how good the reason sounds

Why 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 Mentioned

Stacking Benjamins Field Kit • — the all-in-one net worth and budgeting tool referenced in the updated intro
The 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.

Your Financial Order of Operations: What to Fix First SB1888

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

 • Why waiting until kids are "old enough to understand the math" is one of the most common mistakes parents make
 • A simple age-by-age breakdown of what to teach, from age six all the way through eighteen
 • Whether you should tell your kids exactly how much you earn, and what to say instead if you'd rather not
 • Why letting kids make small, affordable money mistakes now protects them from much bigger ones later
 • How to talk to kids about in-game currencies and microtransactions in a way that actually sticks
 • A refreshingly simple way to build an allowance system that teaches real financial judgment, not just chore compliance
 • Why you don't need to be great with money yourself to teach your kids well, and what actually matters more than expertise

Why 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 Mentioned

Follow the Money by Alaina Trivax • — Alaina's new activity-based book teaching kids about money
Let's Make It Grow • — Alaina's platform helping parents teach financial literacy
Gifting Sense • — Karen Holland's nonprofit teaching kids mindful spending, including the "Spending Ed" program
Easy 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.

What to Teach Your Kids About Money, and When 1887

"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 With

 • Why "trust versus will" is the wrong question, and the three-column framework that actually determines what you need
 • What a lady bird deed is, when it makes sense, and the family conflict it can quietly set up down the road
 • The tax detail buried in gifting property early that can cost your heirs tens of thousands of dollars they didn't expect
 • Why naming a power of attorney without having an honest conversation first is one of the most common and costly mistakes families make
 • The five-year Medicaid look-back rule explained clearly, including what happens if you don't quite make it to five years
 • How debt actually works after someone dies, including a real statute of limitations window most people don't know exists
 • A special needs trust structuring tip that can protect a family member's government benefits without giving up their inheritance

Why 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 Mentioned

Your Money, Your Way by Tim Semro • — Tim's book on estate planning, free to download
Semro Henry Ltd. • — Tim's estate planning law firm
Stacking 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.

Tim Semro Answers Your Weirdest Estate Planning Questions SB1886

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

 • The four psychological traps, stacked together on purpose, that get otherwise careful people to sign without reading
 • Why the phrase "this is standard" should be one of the biggest red flags in any negotiation
 • A green flag, yellow flag, red flag rundown of common contract moments, from blank spaces to rush deadlines to page-by-page initials
 • The hidden clause in shared leases that can leave one person legally responsible for an entire group's unpaid rent
 • Why the number on the front page of a lease or job offer is often just marketing, and where the real total actually lives
 • The critical difference between an employment offer letter and the actual employment agreement, and why only one of them is legally binding
 • Why severance is almost always more negotiable than employers make it seem, and the two questions worth asking about any financial product before you commit

Why 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 Mentioned

Don't Sign That by Leo Mann • — Leo's #1 bestselling guide to consumer contracts
The Contract Literacy Movement • — Leo's initiative teaching everyday people to read what they sign
Stacking Benjamins Field Kit • — the all-in-one budgeting, credit monitoring, and financial tracking tool
Stacko 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.

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

Steve Chou has made lots of money. He didn't do it by "following his passion." He sold hankerchiefs with his wife, who wanted to quit her job. Together they created businesses that rolled in cash. But Steve will be the first to tell you that the method he used was flawed. Today he'll dive into his mastakes and share kes to help you start your own business and make "a couple million" a year (Steve's number) without ruining your life, your relationships, or resorting to the "hustle culture" that chews up and spits out so many would-be entrepreneurs every year.

In our headline segment, we'll dive into the automation craze. Chat-GPT is doing homework, writing ad copy, creating books...what can't automation do? The government is casting it's gaze on automation and has issues some strong warnings. We'll share those AND what you should think about when you're considering automation (or recommendations that come from automation) in the future.

Of course, we'll also wind up the TikTok minute, Doug's trivia, and much more!

FULL SHOW NOTES: https://www.stackingbenjamins.com/steve-chou-1356

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at StackingBenjamins.com/201.

Enjoy!

 

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

Make "A Couple Million" Without Ruining Your Life (with Steve Chou)

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