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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 emotion from decisions most people make entirely on feeling.
What You'll Walk Away With
Why This Matters Now
For investors in their 40s, the goal quietly shifts. Finding the next big winner starts to matter less than building something that actually holds up over time. Markets feel noisier, AI tools feel more powerful, and the promise of faster answers has never been louder. But long-term results still come down to behavior, discipline, and repeatable systems -- the same unglamorous edge the pros have been using all along. Knowing that changes how you listen to the noise.
From the Basement
Joe and OG press Claire and Lee on what a decade of studying elite investors actually reveals -- and the answers are more behavioral than most people expect. The crew then turns to AI in financial advice, and OG shares a story that should give every advisor and DIY investor pause before they hit send on anything they haven't personally verified. Doug arrives with a trivia question that somehow connects Michael Jackson's moonwalk to one giant leap for your bragging rights. Whether the basement scoreboard sticks the landing is best discovered with your earbuds in.
FULL SHOW NOTES: https://stackingbenjamins.com/diving-deep-into-stock-market-research-1820
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
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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 strategic asset quietly holding your entire plan together.
What You'll Walk Away With
Why This Matters Now
In your 40s, financial decisions don't happen in isolation -- they stack. You're managing growth, protection, and flexibility at the same time, often with less margin for error than you'd like. Cash can feel like a drag when markets are moving and rates look modest. But the right emergency fund creates options, absorbs shocks, and quietly makes every other part of your plan more resilient. It's not idle. It's infrastructure.
From the Basement
Joe and OG dig into what your emergency fund is actually doing -- and it turns out the math goes well beyond the interest rate on the tin. OG and Anna close out the show with the second installment of the new financial planning basics series, walking through a five-column cash flow system simple enough to sketch on a napkin but powerful enough to anchor your entire plan. Doug arrives with elevator trivia that's smoother than the ride up. Whether the scoreboard moves is a conversation best had with your earbuds in.
FULL SHOW NOTES: https://stackingbenjamins.com/how-to-get-the-most-out-of-your-emergency-fund-1819
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.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.
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 something harder: a system that doesn't force bad decisions when everything around it is going sideways.
Because the real test of your plan was never the bull market. It's right now.
Paula Pant — Afford Anything host and career-flexibility advocate.
On building a portfolio that doesn't quit:
On the parts of your plan that aren't your portfolio:
On measuring success differently:
If you're in your 40s, the math has changed. You've built real momentum, which means a major mistake costs more than it used to, and there's less runway to recover. Markets are unpredictable, job security looks different than it did a decade ago, and the financial media is a constant nudge toward reacting to something.
An all-weather approach doesn't try to predict what's coming. It prepares for it. The goal shifts from winning every season to still being in the game when the weather turns, and that shift makes all the difference when things actually get hard.
OG's chair is empty this week, but Paul Merriman is a more than worthy substitute, joining Joe, Paula, and Jesse to trade ideas on portfolios built to take a punch. Doug holds down the trivia desk, and let's just say the leaderboard gets an interesting update. Somewhere between market wisdom and basement bragging rights, the point lands: you don't need to win every season. You just need a plan that doesn't fall apart when the weather does.
New to the basement? Subscribe so you never miss an episode, and leave a review if this one helped you stop optimizing for the wrong thing.
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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 crew gets practical. Because even the most purpose-driven life still needs its foundations. Joe and OG break down the one emergency fund mistake that quietly undoes years of good planning — and how to fix it before it matters.
Amy Minkley — FI traveler, community builder, and living proof that the goal was never really the number.
On redefining FI:
On emergency funds (the part everyone gets wrong):
For a lot of people in their 40s, the question has quietly shifted from "Can I retire someday?" to "What am I actually building?"
FI isn't just an escape from work anymore — it's a design problem. And the people figuring it out fastest are the ones pairing big-picture purpose with boring-but-critical foundations: the right emergency fund, the right community, and a clear answer to what they're running toward.
Doug arrives with trivia and — in a surprise result — silver has a moment. Joe and OG tie Amy's story back to the practical stuff, because the most intentional life still needs a financial floor underneath it. Whether you're chasing FI, redefining it, or just trying to understand your emergency fund math, the basement crew has you covered.
Amy's retreat: https://fifreedomretreats.com
Subscribe so you never miss an episode. Leave a review if the basement has ever saved you from a bad financial decision. (You know who you are.)
FULL SHOW NOTES: https://stackingbenjamins.com/your-journey-to-fi-with-amy-minkley-1817
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.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.
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 ever, and what confident investors quietly do differently.
What You'll Walk Away With
Why This Matters Now
Your 40s are often your highest-earning years -- and your most financially complicated ones. Rising costs, family obligations, and career uncertainty can make even disciplined savers feel the pull toward retirement money. The goal isn't just knowing the rules around 401(k) loans. It's building the habits and buffers that make raiding your future self's account something you simply never have to consider.
From the Basement
Joe and OG dig into fresh data showing more retirement accounts getting tapped just as the stakes are highest. Doug shows up with trivia that has no business being as competitive as it gets. The crew also pulls back the curtain on a new beginner-friendly series built to help Stackers pressure-test their entire financial foundation -- because the best retirement strategy was never about knowing when to borrow from yourself.
FULL SHOW NOTES: https://stackingbenjamins.com/how-to-build-good-money-habits-1816
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
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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 (Earn & Invest) sort the signal from the noise.
What You'll Walk Away With
Why This Matters Now
If you're in your 40s, you've watched an entire new financial infrastructure get built around a generation younger than you -- and you may be wondering what's worth borrowing. More access and more information don't automatically produce better outcomes. Knowing which Millennial habits genuinely compound over time, and which ones just feel productive, is the kind of edge that shows up in your account balance a decade from now.
From the Basement
OG makes his case for patience (again), Doc G steers things toward the bigger life picture, and Jen Smith grounds the conversation in the money habits real people actually use. Doug surfaces a trivia question involving a NASA probe budget -- and whether you think you know the answer or not, the basement scoreboard has a way of humbling even the most confident Stacker.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
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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 form after a backdoor Roth conversion might not be the crisis it first appears to be. Turns out some of the most stressful money moments simply come from misunderstanding how the system works.
The conversation tackles real listener questions about whether their savings rate is good enough (spoiler: it depends entirely on the life you want), how to increase savings without feeling squeezed, when to update retirement projections for inflation, and whether contributing to a terrible 401(k) with no employer match still makes sense.
Anna brings fresh perspective on the backdoor Roth tax scare that panics people every year, explaining why receiving a 1099-R is completely normal and usually harmless, plus the small IRS form that keeps your Roth strategy squared away. The crew also breaks down what's actually happening when a mutual fund splits (far less dramatic than the headlines suggest) and the one disclosure document every advisor must provide that contains important clues about fees, conflicts, and discipline history.
Down in the basement, Doug delivers trivia about a document most investors rarely request but absolutely should. Somewhere between inflation math, tax forms, and the occasional rant about terrible retirement plan providers, the crew reminds us that personal finance isn't about memorizing rules. It's about understanding how the pieces fit together, even when the paperwork looks scary.
What You'll Walk Away With:
• Why your savings rate isn't a universal scoreboard and how to judge it based on the life you actually want
• A low friction strategy for increasing savings over time without feeling budget squeezed
• The expense audit trick that quickly reveals whether your spending still matches your priorities
• A smarter way to adjust retirement projections for inflation and how often those numbers deserve a second look
• Why the famous 4% rule should guide your thinking but never run your retirement plan
• How to evaluate whether contributing to a frustrating 401(k) plan still makes sense without employer match
• What's really happening when a mutual fund splits and why the headline sounds more dramatic than reality
• Why receiving a 1099-R after a backdoor Roth conversion is completely normal and usually harmless
• The small IRS form that keeps your Roth strategy squared away and prevents tax headaches later
• The one disclosure document every advisor must provide and the important clues it contains about fees and conflicts
This Episode Is For You If:
• Money decisions suddenly feel like they carry more weight
• You're tired of clean money rules that don't fit your messy real life
• You're ready to understand how the pieces fit together instead of just memorizing formulas
For many people in their 40s, retirement planning gets real, inflation has reshaped expectations, and the margin for error feels smaller. The danger is relying on simple financial rules without understanding the assumptions behind them. When you know how these tools actually work, you can make smarter decisions and stop stressing about the parts that aren't problems in the first place.
Question for You:
What's one money rule you've been following without really understanding why? Drop it in the comments or The Basement Facebook group because Anna, Joe, and OG might tackle it in a future episode.
FULL SHOW NOTES: https://stackingbenjamins.com/stacker-community-show-1814
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.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.
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 whether everyday investors should be chasing the same private deals as the 1%. OG breaks down why "exclusive access" and "higher returns" can also mean binary outcomes, illiquidity traps, and a failure rate that the ultra-wealthy can absorb — and you probably can't.
Oh, and there's a Ty Lopez–led retail investment that allegedly became a Ponzi scheme. So that's fun.
What's in today's episode:
OG also walks through an SEC-inspired framework for evaluating any investment before you hand over a dollar:
Also in the basement:
Doug drops Mustang trivia (the 1964 Ford kind, not the horse kind). The TikTok Minute rides off into the sunset, replaced by a shiny new back-to-basics segment. There are community meetup updates — including Benjamins After Dark in Boston. And somehow, against all odds, Kool-Aid nostalgia becomes a conversation.
Because sometimes the most dangerous investment isn't the one that looks risky. It's the one that sounds like something only smart, wealthy, connected people get access to.
Pull up a chair. The basement is open.
FULL SHOW NOTES: https://stackingbenjamins.com/how-to-avoid-the-wrong-investments-1813
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.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.
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 $190. Today it's near $700. Everyone who waited for the "right time" back then missed massive gains through a pandemic, inflation, and everything else.
The group digs into investing rules that sound simple but get complicated fast. Sell losers quickly and let winners run. But how do you define a loser? Buy low and sell high. But what counts as high? Turn off financial TV noise. But how do you stay informed without getting overwhelmed? They debate whether you need pre-set exit strategies or if long term ownership beats trying to time perfect entries and exits.
The conversation shifts to practical money decisions. Cash versus credit. The group mostly favors credit cards for rewards and dispute protection, but uses cash selectively for tips, travel, and splitting group dinners. They debate the risks of a cashless society, negative interest rates, and what happens when you lose the ability to hold physical money.
Then they tackle one of the toughest money topics. How do you answer kids' hard questions about income, spending priorities, and why you use credit cards? The panel shares candid approaches to money conversations with children that balance honesty with age appropriate information.
What You'll Learn:
• Why waiting for the "right time" to invest often means missing gains
• How to think about investing when markets feel too high
• The difference between selling losers fast and giving good investments time to work
• How to define what counts as a loser versus a temporary dip
• Why turning off financial TV matters more than most people think
• The case for credit cards over cash (rewards, protection, tracking)
• When cash still makes sense despite the convenience of cards
• Risks of a cashless society and negative interest rates
• How to answer kids' tough questions about money without oversharing or lying
• Age appropriate ways to explain income, spending, and credit
This Episode Is For You If:
• Markets feel too high and you're not sure whether to invest
• You've been waiting for a pullback and wondering if you're making a mistake
• You want to hear experienced investors debate real strategies, not just theory
• You're trying to figure out the cash versus credit question
• You need language for talking to your kids about money honestly
Question for You:
Have you ever waited to invest because the market felt too high, and if so, did you regret it? Drop your story in the comments or The Basement Facebook group because this roundtable might shift how you think about timing.
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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 hits crossover from Stacking Adventures brings George's story to the basement, not because it's about exotic travel (though the destinations are incredible), but because it illustrates something crucial about the retirement mindset. The question isn't whether you can afford to travel. The question is whether you're willing to reinvent yourself when the structure of work disappears.
George shares the planning behind his epic journey, including why he used a travel agent (yes, really), how he chose destinations that would challenge him rather than just relax him, and what each stop taught him about identity, purpose, and staying relevant after a career ends.
From South Africa's Robben Island and a five day safari that taught him about patience, to Australia's Great Barrier Reef and a Melbourne Immigration Museum exhibit that forced him to rethink identity, to New Zealand's Milford Sound and a Maori dance lesson about seeking approval, to Japan's samurai service culture and Hiroshima's lesson in resilience, to Canada's awe inducing Rockies and French-flavored Quebec. Every stop was chosen deliberately to teach him something, not just show him something.
The conversation explores his DARE method for retirement planning, why so many retirees struggle with identity once their business cards disappear, and how intentional travel creates the mindset shift that makes retirement feel expansive rather than diminishing.
Along the way, Joe and Crystal plug the "Where in the World is Crystal Hammond?" guessing game (she's not in the continental U.S. or Aruba), announce Seattle and Boston community meetups, and mention the Vault tool for credit monitoring. Plus, you'll hear about George's book, Odyssey of an Elder: Around the World in 80 Days.
What You'll Learn:
• Why retirement success depends on mindset transformation, not just financial preparation
• George's DARE method for retirement planning and identity
• How to plan transformational travel versus just vacation travel
• Why choosing unfamiliar destinations matters more than comfortable ones
• What each stop on George's journey taught him about life after work
• How travel forces identity shifts that make retirement feel expansive
• Why so many retirees struggle once their professional identity disappears
• Practical strategies for reinventing yourself when work ends
• How to use travel as a tool for personal growth, not just leisure
This Episode Is For You If:
• You're approaching retirement and worried about losing your identity
• You've saved enough money but haven't thought about who you'll become
• You're recently retired and struggling with the transition
• You want retirement to feel like expansion, not contraction
• You believe travel can transform you, not just entertain you
Question for You:
If you could take an 80-day trip designed to transform you (not just relax you), where would you go and why? Drop your answer in the comments or the Basement Facebook group.
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From the publisher's feed
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…
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
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