The Stacking Benjamins Show
The Stacking Benjamins Show is a personal finance podcast that makes money topics fun and accessible. Hosted by former financial advisor Joe Saul-Sehy and CFP Josh Bannerman, the show features expert guests, real headlines, and listener questions. Topics include investing, retirement, budgeting, real estate, and behavioral finance. It has won multiple awards and is known for its entertaining yet educational approach.
Episodes
The Retirement Wall of Shame: Mistakes That Wreck Retirement Plans (SB1863)
Most retirement content talks about what to do. This episode talks about what actually goes wrong -- and how often it happens to people who thought they had it figured out. Joel Larsgaard of How to Money, Paula Pant of Afford Anything, and Jesse Cramer of Personal Finance for Long-Term Investors each nominate their worst retirement mistake for the wall of shame. Some make it. Some get arg
Can You Actually Make Money Buying a Franchise? (with Alex Smereczniak) SB1862
Every time you drive past a packed 7 Brew or a Raising Cane's with a line around the block, you probably wonder for about 30 seconds what that owner's life looks like. Is it printing money? Is it a nightmare? Is it something a regular person can actually do? Alex Smereczniak has owned franchises, helped hundreds of people buy them, and built a platform specifically to cut through the hype
When Borrowing Against Your House Is Smart (And When It Quietly Wrecks Your Plan) SB1861
Americans are sitting on more home equity than ever -- and more of them are tapping it. Not because they're struggling, but because they locked in ultra-low mortgage rates and they're not giving those up. So instead of refinancing, they're turning to HELOCs and home equity loans. Joe and OG walk through the math, the psychology, the questions most people never think to ask, and the specif
What Would You Do With a $500,000 Inheritance -- And What Would You Leave Behind? SB1860
Americans are in the middle of the largest wealth transfer in history. Trillions of dollars are moving between generations right now. But what do you actually do when half a million dollars lands in your account? And on the other side of that question: when it's your turn to give, do you leave it when you die or give it while you're alive? Do you split it equally or based on need? And wha
Dana Anspach on the Four Phases of Retirement (and why your go-go years are the most important) SB1859
Most retirement planning focuses on accumulation -- how to save enough. Dana Anspach of Sensible Money has spent her career on the other side of that equation: what happens when it's time to actually spend the money. In her new book Living Off Your Acorns, she breaks retirement into four distinct phases -- pre-go, go-go, slow-go, and no-go -- and argues that the decade before you retire m
The SpaceX IPO Wasn't for You (and that's actually fine) SB1858
SpaceX raised $75 billion in the largest IPO in history -- more than all 71 other IPOs combined so far this year. Shares jumped nearly 20% on day one. Elon Musk became the world's first trillionaire. And if you're a regular investor asking whether you missed out, Joe and OG have a very specific answer: the life-changing money was already gone before the ticker symbol appeared. Here's how
Financial Rules That Sound Smart Until You Actually Test Them (Money "Rules" We Had to Unlearn) SB1857
Everyone inherited financial wisdom from somewhere -- a parent who clipped coupons at three different grocery stores, a first job, a financial guru, or just the culture you grew up in. Some of those beliefs serve you. Some of them quietly hold you back. Chris Hill of Money Unplugged joins Joe, Paula Pant, and OG to share the money habits they've had to unlearn -- and then the whole group
Isaac Newton Lost 80% of His Fortune in a Bubble -- What That Teaches Every Investor (SB1856)
Thanks to Surfshark for sponsoring the show. Go to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN!Isaac Newton was one of the smartest humans who ever lived. He also bought into the South Sea Bubble, sold for a profit, watched it keep climbing, bought back in out of pure FOMO, and rode it all the way down to an 80% loss t
AI Agents Want to Trade Your Stocks and Shop With Your Credit Card -- Here's Why That's a Problem (SB1855)
Robinhood just launched agentic trading -- an AI that can execute stock trades and purchases on your behalf using criteria you set in advance. There's also a new agentic credit card that can shop for you automatically. Joe and Anna dig into why handing execution over to a machine is fundamentally different from using AI as a thinking partner -- and why the people most excited about AI age
8 Signs You're Winning With Money SB1854
Thanks to Surfshark for sponsoring the show. Go to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN!You might not look rich on Instagram. That doesn't mean you're behind. Joe, Paula Pant, Jesse Cramer, and Anthony Weaver from About That Wallet work through eight real signs that your financial life is on track -- covering stability, b
Helping Mom With Money Before It's Too Late (SB1853)
One day you're comparing Roth IRA options. The next you're helping Mom navigate long-term care paperwork, fighting with a bank over a power of attorney document, and wondering how anyone manages all this without losing their sanity.Welcome to the world of financial caregiving.Today, certified financial planner and financial journalist Beth Pinsker joins us to share the lessons she learned
59% of Retirees Left the Workforce Earlier Than Planned -- Are You Ready If It Happens to You? SB1852
Most people plan their retirement like they control the date. The data says they don't. A new Society of Actuaries study found that 59% of retirees stopped working earlier than expected -- and for most of them, the decision wasn't theirs. Health setbacks, job loss, caregiving demands, and plain old job dissatisfaction all showed up before the spreadsheet said it was time. Joe and OG dig i
Why High Earners Still Feel Broke (And What to Do About It) SB1851
Thanks to Surfshark for sponsoring the show. Go to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN!You're making more money than you ever have. Your net worth on paper looks great. And yet somehow, there's still too much month left at the end of the money. Joe, OG, Paula Pant, and Jesse Cramer dig into why high earners fee
Retire by 30: Cody Berman on Building Financial Freedom Faster Than You Think (SB1850)
Cody Berman had the $80,000 corporate job straight out of college, the four-hour daily commute, and the career path everyone said he should want. He hated all of it. By 25, he was financially free -- not because he stumbled into crypto or built a unicorn startup, but because he obsessively maximized the gap between what he made and what he spent, tried 30 different side hustles until a fe
How to Add 1% to Your Portfolio Without Taking on More Risk (The Systems) SB1849
Most DIY investors spend their energy optimizing investments. The wealthiest investors optimize systems. According to Vanguard, a great advisor can add roughly 3% to your portfolio -- not by picking better stocks, but by keeping you from wrecking what you already have and by making the boring structural decisions most people skip. Joe and OG walk through the return boosters that actually
Stop Treating Every Financial Decision Like It's Mount Everest SB1848
Most of the financial decisions keeping you up at night are two-way doors. You can change them. You can undo them. The real one-way doors -- the decisions that actually lock you in -- are rarer than you think, and the problem is we're spending the same emotional energy on both. Joe, OG, Paula Pant, and Jesse Cramer take Simone Stolzoff's uncertainty framework from Wednesday and run it str
Why Uncertainty Is an Opportunity (and some Wall Street players don't want you to know that) SB1847
The five highest global uncertainty readings since the 1980s have all occurred in the last five years. And yet the answer Wall Street keeps selling -- products that promise upside without downside -- is mathematically impossible and provably underperforms over time. Simone Stolzoff, author of How to Not Know, spent years studying how people, companies, and investors navigate uncertainty w
How Much Should You Really Save Without Hating Your Life? SB1846
Everyone wants to know the magic savings number. Is it 10%? 15%? Half your paycheck while eating ketchup packets in the woods?In this Memorial Day basement hangout, Joe, OG, Doug, and Len Penzo cut through the personal finance nonsense and tackle the real question:How much should YOU actually save?Instead of guilt trips and impossible rules, the crew breaks down how real people build weal
Where Are You Drawing the Line? How Smart Spenders Decide What to Cut and What to Keep (SB1845)
Prices are up. Budgets are tighter. And people are making some surprising choices about what stays and what goes. The woman skipping the new laptop and the graduation dress is still booked for a Disney cruise, a Bruno Mars concert, and a trip to Lake Erie. It turns out inflation doesn't just squeeze your wallet -- it forces a conversation about what you actually value. Joe, OG, Paula Pant
How to Plan the Perfect Theme Park Trip Without Wasting Your Money or Your Day (SB1844)
Every family knows the feeling. You spend $1,000 to get everyone to the happiest place on Earth, and by 1:30 someone's crying, someone's sunburned, and somebody just paid $18 for a hotdog. Robert Niles from Theme Park Insider (the site that Robert jokes AI is pulling all its theme park data from) comes back to the basement to help you avoid that fate. This year he's also got strong opinio
Too Much of One Stock? How to Diversify Without Blowing Up Your Tax Bill (SB1843)
You wake up, check your portfolio, and realize one stock has quietly become your entire retirement plan. Maybe it came from an employee stock purchase plan. Maybe Grandma left you a pile of Apple shares. Maybe you bought NVIDIA in 2012 because you liked the graphics card and forgot about it. However you got here, the problem is the same: one company now owns you. Joe and OG walk through e
The Habits That Actually Make Millionaires (SB1842)
What actually separates people who build lasting wealth from everyone else? Not the tips. Not the apps. The habits. Joe put the question to a panel of financial planners, coaches, and bloggers -- and turned it into a game. Seven habits, three rounds, two points up for grabs. Monica Scudieri, who paid off $257,000 in debt and reached financial independence in 10 years, joined OG and Jesse
Beth Kobliner on the Money Basics That Still Work 30 Years Later (and the New Traps Nobody Warned You About) SB1841
Thirty years ago Beth Kobliner wrote the book that a generation of financial planners handed to their clients' kids. The core advice still holds. But the world around it has changed dramatically -- frictionless spending, gambling apps disguised as investment platforms, and a housing market where the average first-time buyer is now 40. Beth comes back to the basement with an updated editio
Why 67% of Americans Fear Running Out of Money More Than Dying (And What to Do About It) SB1840
A new study just confirmed what most people in their 40s already feel but rarely say out loud: running out of money is scarier than death. Gen X is leading that number at 73% -- and the reasons why make a lot of sense when you look at what that generation is actually navigating. No pensions. Rising costs. Longer retirements. Markets that never seem to settle. Joe, OG, and Len Penzo dig in
40 Ways to Take Control of Your Money -- Which Ones Actually Work (SB1839)
Ever spend an entire afternoon trying to save 38 cents… while completely ignoring the $10 decision sitting right in front of you?Yeah. We’ve all been there.In today’s roundtable, we’re diving into the money habits that actually build wealth, and the ones that just make you feel productive while your financial progress spins its wheels. From lifestyle inflation to automated savings to the
How to Save Your First $25,000 -- The Roadmap Most People Get Wrong (SB1838)
Getting to your first $25,000 saved is harder than anything that comes after it. Not because the math is complicated -- because the habits aren't built yet, the fixed expenses are already set, and the standard advice about cutting small treats completely misses where the real leverage is. Scott Trench, VP of Operations at BiggerPockets and author of Set for Life, brings a roadmap that cha
Thinking in Bets: Annie Duke on Making Smarter Decisions When You Don't Have All the Facts - Greatest Hits! (SB1837)
What if the reason your investment decisions feel so hard isn't the market -- it's how you're wired to think about outcomes? Annie Duke spent years as a professional poker player winning over $4 million in tournaments, then devoted the next chapter of her career to understanding why smart people consistently make bad decisions. The answer has nothing to do with intelligence and everything
Invest Like the 1%? What to Steal, What to Scale, and What to Skip (SB1836)
You've seen the ads. Invest like the ultra-wealthy. Get access to what the 1% does. But what does the 1% actually do -- and how much of it should a normal person try to copy? Joe, OG, comedian and finance educator Roxanne Duckels, and Jesse Cramer run every popular "rich people investing" idea through a simple filter: steal it, scale it, or skip it. The answers will surprise you -- especi
Mrs. Dow Jones on How to Become a Future Rich Person (Without Giving Up Your Life) SB1835
Haley Sacks didn't grow up knowing what a 401k was. She was nannying for a kid named Winthrop on the Upper East Side, doing comedy at night, and getting paid cash under the table. Then she sat in an HR meeting and her eyes glazed over -- and she decided that was the last time she'd be caught unprepared with her own money. Today she's Mrs. Dow Jones, with millions of followers and a new bo
Index Investing 101: Stop Picking Funds and Start Building the Mix That Actually Works (SB1834)
Most investors spend their energy asking the wrong question. It's not which fund is best -- it's which combination of funds gets you to your actual goal at a cost and complexity level you'll actually maintain. Joe and OG break down the full index investing playbook: where to start, when to add complexity, what Wall Street calls indexing that really isn't, and the one number that should ch
How to Find the Money Leaks Hidden in Your Financial Statements (SB1833)
Most people glance at their balance and move on. Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer argue that's exactly where the money quietly disappears. This week they go statement by statement, credit card through brokerage, and share what actually deserves your attention and what you can safely ignore.In this episode:The one thing on your credit card statement that trips up even carefu
Bitcoin, Blockchain, and the Stuff Nobody Actually Explains (SB1832)
Blockchain. Stablecoins. Wallets. Staking. Halvings. If you've spent the last few years nodding confidently through crypto conversations while quietly hoping nobody asks a follow-up question -- this episode is for you. Retired anesthesiologist and trading veteran Joe Duarte went from crypto skeptic to informed pragmatist, and today he brings the plain-English breakdown that most crypto co
The Tax Triangle Most Investors Have Never Heard Of (SB1831)
Most people think about investing in terms of what to buy. Joe Saul-Sehy, OG, and CFP Anna Allem argue the more important question is where you put it. This week they break down the three-bucket tax triangle that could save you thousands in retirement, plus answer listener questions on Trump accounts, UTMAs, and how to pull together a home down payment when your money is locked up in all
The Best Money Advice We Wish We Knew at 20 (Live from Texas A&M - Texarkana) SB1830
What would you ask about money if you had the mic?Live from Texas A&M Texarkana, Joe Saul-Sehy, Paula Pant, and financial educator Jay Davis take questions from students facing real-world money decisions—like choosing between passion and paycheck, avoiding lifestyle creep, investing safely, and building a financial future from scratch.If you're in your 20s—or wish you could do them ov
The Mental Game of Money: What Elite Athletes Know That Most Investors Don't (SB1829)
The same mental patterns that cause investors to panic-sell during a downturn, chase validation through status purchases, or freeze up when facing big financial decisions -- those are the exact patterns performance coach Jim Murphy has spent decades helping elite athletes overcome. His framework isn't about trying harder. It's about getting aligned. And today he brings it down to the base
Geopolitical Risk Is Spiking. Here's Why You Should Do Nothing. (SB1828)
Oil prices up. Tariffs in the headlines. Markets bouncing. Your phone serving you a fresh reason to panic every 10 seconds. This week Joe Saul-Sehy and OG break down why everything you're feeling right now is normal, why acting on it is the mistake, and how to think about your portfolio when the world feels like it's on fire. Plus CFP Anna Allem joins OG for the basics segment, walking th
No Retirement Savings at 40? Here's Exactly What to Do First (SB1827)
Most people don't start thinking seriously about retirement until their forties. If that's you, the good news is you're not behind. You're normal. And this week three CFPs, Jackie Cummings Koski, Roger Whitney, and OG break down exactly what to do, in what order, starting right now.In this episode:Why panic is the enemy of a good retirement plan, the first place your money should go befor
Why You Should Stop Saving for Retirement 3 Years Early (SB1826)
Retirement expert Jamie Hopkins has spent 20 years helping people plan for retirement, and his most counterintuitive advice stops most savers cold: in the final years before you retire, putting more money away might actually be hurting you. This week he joins Joe and OG to explain why, and what to do instead.In this episode:Why financially prepared retirees still end up miserable, how to
You Don't Need a Huge Income to Build Real Wealth (SB1825)
A Kiplinger study of 1,000+ everyday millionaires found four traits that kept showing up. None of them involve a big salary, a hot stock tip, or a lucky break. This week Len Penzo, OG, and Joe dig into what those habits actually look like in practice, how to train yourself to spend with intention, and how to find a financial advisor who does what you actually need.In this episode:The "Mid
Building Your Personal Finance Curriculum (At Any Age) SB1824
Most of us were never taught this stuff. So, where do you actually start?Thirty-nine states now require a personal finance course to graduate from high school. That's real progress — and it still might not be enough. Because financial education isn't a one-time event. It's a living curriculum that has to grow with you, stay connected to your actual life, and — crucially — help you get out
You Don't Need a Big Break to Become a Millionaire -- You Need a Better System (SB1823)
Bola Sokunbi didn't start with advantages. She started with a $54,000 salary she never negotiated, a rollover IRA mistake that cost her 40% of her savings, a tenant who stopped paying rent for eight months, and a first year of business that generated exactly $200. She's also built one of the most influential personal finance brands in the country and helped millions of people on the path
What to Do With Your Money When the Market Is Scaring Everyone Else (SB1822)
Markets are down. Social media is loud. And somewhere in the back of your mind, a voice is asking if you should do something. That voice has cost investors more money than any bear market in history. Joe and OG dig into what actually separates disciplined investors from everyone panic-refreshing their brokerage account -- and how to build the guardrails that keep you from making the one m
Stop Relying on Willpower (Build This Instead) SB1821
Willpower has a terrible track record with money. It works until it doesn't, and then your good intentions are the first thing to go when life gets busy. The investors and savers who actually make consistent progress aren't trying harder. They've built systems that keep running in the background whether they're paying attention or not. Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer break
Even the Pros Are Wrong Half the Time. Here's What They Do Differently SB1820
The best investors in the world are wrong -- a lot. Researchers Claire Flynn Levy and Lee Freeman-Shor spent over a decade studying elite money managers and found that being right about stock picks isn't actually what separates the winners. What separates them is what happens after the pick. The discipline, the rules, the willingness to act when the data changes -- and the ability to remo
The Real Return on Your Emergency Fund Has Nothing to Do With Interest Rates SB1819
If your emergency fund feels like it's just sitting there doing nothing, you might be measuring the wrong thing. The real return on cash isn't the yield -- it's what that cash helps you avoid. Panic selling during a downturn. High-interest debt after an unexpected bill. Tapping your 401(k) at exactly the wrong moment. Joe and OG reframe emergency savings not as a financial placeholder, bu
How to Build a Financial Plan That Holds Up When Life Doesn't SB1818
Your financial plan is only as good as what happens to it under pressure.
A market drop. A job loss. An inflation spike that turns "fine" into "wait, what?" Most portfolios are quietly optimized for the good times, and that's exactly why they crack when things get uncomfortable. This week, Joe, Paula, Jesse, and special guest Paul Merriman aren't chasing the highest returns. They're build
What to Build After You Hit "The Retirement Number" (SB1817)
What if reaching financial independence was the easy part?
Amy Minkley spent years optimizing toward her number — then hit it and discovered something nobody's spreadsheet prepares you for: freedom without purpose feels surprisingly empty. She joins Joe and OG to talk about what actually fills the gap: community, meaning, and building something instead of just escaping something.
Then the
The One About 401k Loans (and How To Stay Away From Them) SB1816
A 401(k) loan often looks harmless. You're borrowing from yourself, the interest comes back to you, and you'll pay it back before it matters -- right? But the fastest way to protect your retirement isn't understanding how loans and hardship withdrawals work. It's building a financial life where you almost never need them. Joe and OG dig into why more people are tapping retirement accounts
Why Doing Less With Your Money Is the New Investing Edge (SB1815)
Millennials didn't just change how people invest -- they changed what investing even looks like. Cheaper, faster, more automated, and occasionally more dangerous than anything that came before. The real question isn't whether to adopt their habits. It's which ones are actually building wealth and which ones are quietly lighting your portfolio on fire. Joe, OG, Jen Smith (Frugal Friends),
When Money Rules Don't Match Real Life (Your Questions!) SB1814
Personal finance loves clean rules. Save 20%. Follow the 4% rule. Always max the 401(k). But real life rarely cooperates with tidy formulas.
This week Joe Saul-Sehy, OG, and guest co-host CFP Anna Allem dig into the gap between the advice we hear and the messy decisions we actually face. What your savings rate really means. How often you should rethink inflation assumptions. Why a mysteri
Private Equity for Regular People: Higher Returns or a Very Expensive Lesson? SB1813
The ultra-wealthy get access to private equity, private credit, and pre-IPO deals the rest of us don't. Now, suddenly, those same deals are being marketed to you. Coincidence? Maybe. Cause for suspicion? Absolutely.
Joe, OG, and Doug settle in at the basement desk (yes, Joe's mom's basement — the most prestigious financial address in podcasting) to dig into a Wall Street Journal headline
Should You Invest When the Market Feels Too High? SB1812
The market feels expensive. Again. So should you invest or wait for a pullback?
Joe Saul-Sehy brings together a powerhouse roundtable featuring Len Penzo, Paula Pant (Afford Anything), and Greg McFarlane to tackle the question every investor faces when markets hit new highs. The twist? This conversation originally happened in 2016 when the SPY ETF which tracks the S&P 500 was trading
Around the World in 80 Days: The Travel Mindset That Makes Retirement Bigger (SB1811)
What if retirement isn't about doing less, but about becoming more?
George Jerjian spent his career as a retirement mindset coach, helping others navigate life after work. Then he decided to practice what he preached. He planned an 80-day round-the-world journey, intentionally choosing unfamiliar countries where he'd be forced out of his comfort zone and into transformation.
This greatest
Building Courage One Small Step at a Time SB1810
If Jen Drummond can climb K2, you can open that Roth IRA.
That's the premise of this greatest hits episode featuring mountaineer and author Jen Drummond, who became the first woman to complete the Seven Second Summits. But here's why we're replaying this conversation from early 2024: it's not about mountaineering. It's about courage.
Joe Saul-Sehy opens by explaining why courage matters f
You Don't Need to Be a Money Genius to Win SB1809
Live from Joe's mom's basement (where humility is encouraged and spreadsheets are optional), the crew tackles a deceptively simple question. If most people think they're above average with money, what advice actually helps someone who isn't?
Joe Saul-Sehy, OG, Doug, Jesse Cramer, and guest Whitney Hanson (Money Nerds podcast) run a thought experiment inspired by Morgan Housel's observatio
How She Eliminated a $43,000 Hospital Bill (SB1808)
Live from Joe's mom's basement (where the jokes are free but hospital care apparently isn't), the Stacking Benjamins crew tackles two very real financial stressors: surprise medical debt and a shifting housing market.
First up is Imani Vance, who joined the Coast Guard at 19 and soon faced a nightmare scenario. What started as appendicitis escalated to severe sepsis after limited on-base
Suze Orman Changes Her Mind on Working to 70 (SB1807)
Live from Joe's mom's basement (complete with dog mugs, birthday roasting, and Doug polishing his trivia crown), the crew tackles a headline that caught plenty of attention. Suze Orman backing off her long held stance that everyone should work until age 70.
Does that mean you shouldn't work longer? Not exactly.
Joe Saul-Sehy, OG, Doug, and special guest Len Penzo break down the math behin
How to Talk to Kids About Money (Without Making It Weird) SB1806
Want your kids to grow into confident money decision-makers without turning every dinner conversation into a financial lecture? In this roundtable episode, Joe sits down with Livia (“Liv”) Roder, host of the Liv Lab Podcast, Karen Holland of GiftingSense.org, and John Lanza, host of the Art of Allowance Podcast to explore what actually helps kids understand money before the stakes get big
Best Tax Software for 2026 (And Handling Market Drops) SB1805
Live from Joe's mom's basement (where receipts go to be judged and spreadsheets fear OG), this episode tackles two big questions Stackers are asking right now. What's the best tax software for filing your 2025 return? And what should normal, long term investors make of gold, silver, and crypto taking a wild ride?
Joe Saul-Sehy and OG are joined by Robert Farrington from The College Invest
The Boring Plan That Built $2 Million SB1804
Think building seven figure wealth requires exotic investments or perfect timing? This President's Day episode from Joe's mom's basement tells a very different story.
Joe Saul-Sehy, OG, and Neighbor Doug dig into a Kiplinger My First Million case study featuring a Wisconsin couple who started saving at age 32 with exactly zero invested and quietly built $2 million over the next 22 years u
Love It or Leave It: Financial Edition (SB1803)
Nothing says romance like a heated debate about the 4% rule.
Live from the basement (which suspiciously resembles YouTube headquarters), Joe Saul-Sehy, OG, Neighbor Doug, and the panel celebrate Valentine's Day weekend the only way Stackers know how: by putting their favorite financial ideas on the hot seat.
This isn't a polite discussion. It's a rapid fire "love it or leave it" showdown
How to Talk About Money Without Fighting SB1802
What's more romantic than roses and chocolate? How about not fighting about money.
Joe Saul-Sehy and OG welcome Douglas and Heather Boneparth, the financial planning power couple who literally wrote the book on navigating money in relationships. Broadcasting from the basement (where love is patient and spreadsheets are kind), the crew dives into how people can build financial trust, avoid
Are You Investing or Just Placing Bets? SB1801
Joe Saul-Sehy, OG, and Neighbor Doug pull up a rickety basement chair and unpack a growing trend: people treating investing like a series of high stakes bets instead of a long term plan. Sparked by a recent Wall Street Journal piece on aggressive investing, the gang digs into where the line is between smart risk taking and straight up gambling with your future.
Using plenty of real world
The Worst Money Advice Ever (Episode 1800!)
Eighteen hundred episodes calls for something special, and what better way to celebrate than by dragging the absolute worst money advice into the light and laughing at it together?
Special guest and CFP Sarah Catherine Guiterrez from Aptus Financial joins Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) for a rapid-fi
Building a Wealth Machine That Lasts Generations (SB1799)
Whitney Elkins-Hutten's story isn't about overnight success or getting lucky. It's about building a wealth machine that keeps working even when life throws curveballs.
Broadcast as always from Joe's mom's basement, this episode explores how Whitney went from a modest, very 1970s upbringing to creating systems that generate lasting wealth, and what everyday people can realistically take fr
Stop Leaving Money on the Table at Tax Time (SB1798)
Taxes don't have to feel like something that happens to you.
Joe Saul-Sehy, OG, and Neighbor Doug break down the biggest recent tax changes and, more importantly, how to use them intentionally instead of accidentally leaving money on the table.
This isn't about memorizing the tax code or becoming a DIY CPA. It's about understanding where the real opportunities are right now, which moves m
How to Get 1% Better Without Burning Out (SB1797)
What if the path to better money decisions, more confidence, and a calmer life wasn't a massive overhaul but just getting a tiny bit better today than you were yesterday?
Joe Saul-Sehy, Neighbor Doug, OG, and Paula Pant (Afford Anything) are joined by David Gillis, creator of the 1% Better Conference, for a roundtable exploring the surprisingly powerful idea of improving by just 1% at a t
The Science of Better Ideas with George Newman SB1796
Where do great ideas come from, and why do they always show up in the shower, on a walk, or five minutes after you've stopped trying so hard?
Joe Saul-Sehy, OG, and Neighbor Doug welcome this week's mentor, behavioral scientist George Newman, to unpack how creativity really works and how Stackers can use it to make better decisions with money, careers, and life.
This isn't about becoming
When to Trust Your Gut and When to Trust the Math SB1795
Ever made a money move that felt right then immediately wondered if you just emotionally invested in a bad idea? We've all done it. Some of us have receipts.
Joe Saul-Sehy, OG, and Neighbor Doug tackle one of the trickiest parts of personal finance: knowing when to trust your gut and when your gut needs to sit down and let the math speak.
Because here's the thing. Most Stackers aren't str
How to Afford Life Without Living Like a Monk (SB1794)
Inflation may be doing its best to body slam your budget, but this episode is all about fighting back without turning your life into a sad spreadsheet.
Joe Saul-Sehy, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) are joined by special guest Justin Brown-Woods (Price of Avocado Toast) for a roundtable tackling the big question Stac
How to Make Your Money Support the Life You Want (SB1793)
What if your money stopped dictating your schedule and started supporting the life you actually want to live?
Joe Saul-Sehy welcomes CFP Dana Anspach of Sensible Money as special guest co-host for an episode featuring this week's mentor, Andy Hill. Andy shares how he stepped away from the corporate grind, redesigned his priorities, and built a life where family and flexibility came first.
How to Prioritize Your Money: Listener Q&A (SB1792)
Ever feel like your money questions don't fit neatly into one category? One minute you're thinking about retirement, the next it's insurance, emergency funds, gifting money, or whether your workplace plan is helping or hurting you.
This is one of those episodes where Stackers bring the real-life questions, and Joe Saul-Sehy, CFP Anna Allem, and Neighbor Doug help sort through the noise.
The Money Habits to Keep and Ditch in 2026 (SB1791)
Some people kick off a new year with a vision board. We prefer a runway show in sweatpants from Joe's mom's basement.
Joe Saul-Sehy, OG, and Neighbor Doug throw personal finance into the spotlight and ask the question every Stacker secretly loves: What's officially "so last year" in your money plan, and what's worth keeping for 2026?
Because here's the truth. You don't need a total financ
Build Income Beyond Your Paycheck (SB1790)
If you're making decent money but still feel like you're one bad month away from stress, this episode is for you.
Joe Saul-Sehy, OG, and Neighbor Doug sit down with Mel Abraham to talk about something most Stackers think about but don't know how to start: creating income that doesn't depend entirely on showing up to work every single day. Not side hustle mania or get-rich-quick schemes. J
Breaking Money Rules and Playing Survivor Pantry SB1789
What if some of the "rules" you've been told about money aren't rules at all, just assumptions that haven't been questioned lately?
Joe Saul-Sehy, OG, and Neighbor Doug pull apart a handful of deeply held financial beliefs and see what holds up when real life enters the conversation. From Social Security timing to investment return expectations, the crew explores where common advice works
Our Annual Magic 8 Ball Predictions for 2026 (SB1788)
It's that time of year when we look ahead, squint confidently into the future, and pretend we have any idea what's coming next. In this annual Stacking Benjamins tradition, Joe Saul-Sehy welcomes back Mindy Jensen from the BiggerPockets Money Podcast, Len Penzo of LenPenzo.com, and OG for the predictions episode that blends money talk, pop culture, and just enough nonsense to keep everyon
Making Time for What Matters with Laura Vanderkam (SB1787)
If 2026 already feels busy and it's barely started, you're not imagining it. Joe Saul-Sehy and OG sit down with renowned time management expert Laura Vanderkam to tackle one of the biggest stressors Stackers face. Feeling like there's never enough time to do the things that matter, including managing money well.
Laura helps break the myth that better time management means squeezing more p
Waste Time on Hot Real Estate or IPO Trends or Start Building Wealth? SB1786
A new year has arrived, and with it comes a fresh wave of hot takes, bold predictions, and "can't miss" investing ideas. Joe Saul-Sehy and OG step back from the noise to discuss what clearly doesn't work and then to focus on what actually helps you build wealth in 2026 and beyond.
Rather than chasing hot trends, they revisit the timeless rules that have quietly done the heavy lifting thro
Alex Hormozi on Skills That Actually Build Wealth, Part 2 (SB1785)
What if earning more money in 2025 has less to do with working longer hours and more to do with becoming dangerously useful?
In this conversation, Joe Saul-Sehy and OG sit down with entrepreneur Alex Hormozi to break down how skill stacking, leverage, and better decision-making can radically change your income trajectory, whether you run a business, lead a team, or clock in for a 9-to-5.
Alex Hormozi on Skills That Actually Build Wealth SB1784
What if the biggest driver of your financial future isn't the stock market but your skill set?
In this episode of The Stacking Benjamins Show, Joe Saul-Sehy and the crew sit down with entrepreneur and business strategist Alex Hormozi to unpack one of the most overlooked wealth-building tools Stackers have access to: skill acquisition.
Alex doesn't pitch get-rich-quick nonsense or risky mo
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