The Stacking Benjamins Show

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 -- especially the...

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 book. The b...

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 change how...

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 careful spend...

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 content ass...

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 wrong...

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 over—this...

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 basement to h...

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 through the...

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 before anyth...

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 practic...

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 "Midwest mi...

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 of your...

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 to becomi...

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 mistake th...

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 down the...

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 remove emotio...

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, but as a st...

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 building for s...

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 basement...

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 than eve...

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), and Doc G...

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 mysterious tax f...

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 asking w...

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 at around...