Stacking Benjamins: Your Gateway To Money And Personal Finance

Ever think, “If I just followed the playbook of the ultra-wealthy, I’d be set for life”? Turns out, that’s exactly the kind of thinking that can lead you straight into the arms of a scammer. In this episode, Joe Saul-Sehy and OG break down the traps hidden inside the “invest like the 1%” mantra (and other similar phrases), complete with real-life cautionary tales, including a small-town Ponzi scheme that could’ve been ripped from a Netflix docuseries, and the spectacular belly flop of some YieldStreet real estate bets. But it’s not all doom and gloom in the basement. You’ll also get the scoop on a controversial proposal to let private equity sneak into your 401(k), practical tips for spotting shady pitches before they drain your wallet, and the reminder that a boring-but-solid financial plan beats a flashy scam every time. Plus, the guys field a listener question on long-term care insurance and unpack the often-overlooked basics of HSAs. Between headlines, trivia detours, and a dash of movie talk, this epis

If you’ve ever wondered whether you should pass on your money now or make your heirs wait for the “big reveal” (cue the dramatic reading of your will), this is your episode. Joe Saul-Sehy, OG, and Neighbor Doug welcome Paula Pant from Afford Anything and Jesse Cramer from Personal Finance for Long-Term Investors to play a high-stakes round of “In or Out” with estate planning and charitable giving. Is anonymous giving a waste of good publicity? Should you set up a donor-advised fund or keep it simple? Is sharing your estate plan with your heirs wise—or an invitation to awkward holiday dinners? This isn’t your average dry legal seminar. Between football analogies, dinosaur jokes, and the occasional jab at Ford’s electric truck sales, our crew digs into the real-life choices Stackers face when deciding how—and when—to pass along their wealth. You’ll hear hot takes, smart strategies, and maybe even a nudge to start that conversation you’ve been putting off. From the practical (avoiding probate, maximizing givin

What if there were a way to make charitable giving easier, more strategic, and—dare we say—more satisfying? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Len Penzo welcome Adam Nash, founder and CEO of Daffy, to demystify donor-advised funds. Whether you’ve never heard of them or you’ve been meaning to set one up, Adam walks us through how they work, why they might be a perfect fit for your giving goals, and how they can help you be more intentional with your generosity year-round. But that’s not all—we also turn the spotlight on an often-overlooked money moment: handling a car insurance claim. From gathering evidence at the scene to negotiating with your insurance company, the team shares smart, practical steps to make sure you don’t leave money (or protection) on the table. And, of course, Len dishes up his trademark personal finance storytelling straight from his new book, mixing in lessons you’ll actually remember with tales you didn’t see coming. If you’ve been thinking about g

Estate planning might not sound like the most thrilling topic—but skipping it can create a real mess for the people you care about most. In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug sit down with attorney Tim Semro to cut through the noise on wills, trusts, and life insurance. Whether you’ve been putting off writing a will or you’re wondering if a trust is worth it, this conversation will give you a clearer path forward. Tim walks us through the essentials, from the differences between wills and trusts to the sneaky pitfalls that can trip up your beneficiary designations. We also tackle tricky scenarios—like probate headaches, planning across state (or even international) lines, and how to think about life insurance with living benefits. Plus, we swap stories about scams that hit a little too close to home and the simple moves you can take to protect your finances and family. This episode isn’t about scaring you into action; it’s about showing how estate planning and

Some people chase “work-life balance” like it’s the Holy Grail—spending time, money, and mental energy trying to keep work and personal life perfectly split down the middle. But what if that balance doesn’t actually exist? Live from Joe’s mom’s basement (and not nearly as glamorous as it sounds), Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer pull back the curtain on whether we should be aiming for balance… or something else entirely. In this roundtable, the crew wrestles with the difference between work-life balance, alignment, and integration—and why chasing balance might actually keep you from a truly fulfilling life. You’ll hear personal stories, some hard-won lessons about productivity, and a few well-placed digs at Nautica (including the questionable financial moves Joe made in his youth). And because no basement chat is complete without it, we bring you a trivia challenge you didn’t know you needed. From managing notifications so they stop managing you, to building a life where work and personal pri

Ever wonder how to build a career, business, or financial plan that actually lasts — no matter what life throws at you? This week, we’re bringing you lessons from someone who’s done it for more than five generations. Cheryl McKissick Daniel, president and CEO of McKissick & McKissick, joins Joe and OG to share the strategies her family has used to overcome obstacles, land major deals (like the arena in Brooklyn and countless buildings on the historic register of places), and turn connections into opportunities. Whether you’re growing a business, climbing the career ladder, or managing your money, you’ll walk away with practical ideas to strengthen your network, protect your reputation, and keep moving forward. From the art of negotiation to turning big challenges into bigger wins, Cheryl offers insights you can use right now to build momentum. We’ll explore how revisiting your financial plan regularly can help you avoid surprises, why reputation is an asset you can’t afford to neglect, and how a strong team

Is your 401(k) quietly working for you… or quietly working against you? In the first half of this episode, Joe Saul-Sehy, OG, and Neighbor Doug tackle the most common 401(k) slip-ups that even seasoned savers make—and how to turn yours into a retirement-building machine. Then, in the second half, we turn to a problem many Stackers don’t see coming: going from saving to spending in retirement. Stacker Joel in Cleveland asks how to make the leap without feeling like you’re sabotaging your future. Drawing on OG’s real-world experience guiding clients through this tricky transition and Joe’s research into the psychology of money, we share practical steps to help you spend without guilt, align your withdrawals with your values, and actually enjoy the freedom you’ve worked so hard for. Here’s what you’ll learn in this episode: The most expensive 401(k) mistakes—and how to fix them today Why employer matches are truly “free money” (and how to grab them) Smart moves for rolling over old 401(k)s and

Get ready for a rapid-fire roundtable packed with personal finance opinions that might challenge your own money playbook. In this episode, Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Don McDonald (Talking Real Money) join Joe and OG to declare whether they're in or out on some of the most polarizing financial strategies. Whether you're just getting started or leveling up your financial life, this episode is full of practical wisdom, contrarian views, and a few laughs along the way. Oh—and somewhere in there, we may or may not sneak in a birthday surprise for one of our favorite Stackers.

Think negotiation is just for boardrooms and car dealerships? Think again. In this episode, we bring in Paula Pant from Afford Anything to show how negotiating—done well—can level up your finances, your relationships, and yes, even who does the dishes. Paula breaks down why many of us fear negotiation, how to overcome those internal roadblocks, and how setting clear “aspiration” and “reservation” points can lead to more confident conversations (and better outcomes). Whether you’re asking for a raise or trying to avoid unloading the dishwasher for the fifth night in a row, her tactics are practical and empowering. Also in this episode: What most people miss about their workplace retirement plans, and whether adding a managed account is the edge you’ve been missing A viral TikTok proposal on setting your kids up for millions—can it really work, or is it just social media smoke? Doug delivers trivia and 1970s television references like only he can And we remember a cherished interview, David Gerge

Is your grocery bill beefier than your sandwich? This week, Joe Saul-Sehy, OG, and Neighbor Doug unpack inflation in a way that only we can—by biting into Len Penzo’s Annual Sandwich Survey. Yes, prices are up, and yes, you can still eat well without triggering a credit card crisis. But it’s not just meat and mustard on today’s menu. We’re also serving a fresh look at 401(k) “leakage”—that drip-drip-drip of hardship withdrawals that's turning your retirement plan into a leaky faucet. You’ll get pro-level insight on how to patch those holes before your future income soaks the floor. And if you’re paying for (or dreading paying for) college, Christine from the Stacker community, who works in higher ed, joins to offer sharp and timely advice on keeping costs in check—from completing the FAFSA to finding overlooked aid. Len Penzo’s Sandwich Index Which sandwiches give you the most delicious bang for your inflation-adjusted buck? (Spoiler: bologna stages a quiet comeback.) 401(k) Trouble Brewing Hard

You just came into $50,000—no strings attached. Do you crush your debt? Supercharge your retirement? Blow it all on a podcasting-themed backyard grotto? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Jesse Cramer (The Best Interest) gather around the card table in Mom’s basement to tackle one of the most common “someday” questions in personal finance: What do you do when a windfall lands in your lap? Whether it's an inheritance, work bonus, or prize money (maybe you finally won that game show you keep applying to), the panel explores what smart, emotionally grounded, and goal-aligned decisions look like in the face of sudden cash. Start With the Why Before you touch a dime, the crew walks through the importance of mindset, goals, and not falling into the “I deserve it” trap that has sunk many a lucky winner. Debt vs. Invest vs. Enjoy High-interest debt? Retirement accounts? Travel dreams? The panel weighs each strategy—and surprises us with th

High school math left most of us staring blankly at the board, convinced compound interest was just a fancy way to say "confusing." But what if math could be fun, relevant, and—dare we say—life-changing? In this episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug welcome economist, education reformer, and documentary filmmaker Ted Dintersmith to the basement for a conversation that makes math feel less like a chore and more like a cheat code for life. Dintersmith, best known for his education advocacy and the acclaimed documentary Most Likely to Succeed, joins us fresh off the release of his latest book, Aftermath—a compelling look at how we rethink learning in a world that’s evolving faster than ever. With over a decade visiting 500+ schools and a deep passion for practical math, Ted shares how skills like estimation, probability, and prediction can help you make smarter decisions—especially when it comes to your money. Why Prediction Beats Perfection Ted explains why being ro

Big changes are coming to the tax code—and that could mean big savings if you know where to look. On today’s episode, Joe, OG, and Doug break down the most important updates in the 2025 tax laws and share smart, simple ways to keep more of your hard-earned cash. Whether you're a spreadsheet-loving tax nerd or someone who still asks, “Wait, do I have to file?”—this episode will help you navigate the new rules like a pro. Here’s what we unpack: The 2025 Tax Overhaul: What changed, what stayed the same, and how it affects your bottom line Credits vs. Deductions: Why that $1 credit might be worth more than a $5 deduction (math, but fun) Above-the-Line Moves: Claim valuable deductions without itemizing New Wins for Givers and Drivers: Above-the-line charitable contributions AND (drumroll…) personal auto loan interest is back! Family Tax Breaks: Expanded dependent care accounts and beefed-up child credits 50 and Thriving: New 401(k) catch-up rules that can help you max out your

What if the scariest part of retirement isn’t running out of money—but losing your sense of identity? This week on The Stacking Benjamins Show, we tackle the fears that hold so many people back from financial independence and a joyful, purpose-filled retirement. Joe Saul-Sehy and Doug are joined by an all-star panel of financial thinkers: Mark Trautman (Mark’s Money Mind) Paula Pant (Afford Anything) Jesse Cramer (Personal Finance for Long-Term Investors) Together, they unpack the emotional, practical, and strategic side of planning your next chapter—whether you're closing in on retirement or still working toward it. The biggest fears about retirement: from running out of money to running out of meaning. The “one more year” syndrome: why it's so tempting to delay and how to break through. Time freedom vs. financial freedom: how to align your life goals with your money strategy. Tactics to conquer fear: income layering, diversified portfolios, annuities, and rental

What do your financial priorities look like when you're just getting started... or when you're sitting on $100 million? If you’re still stuck trying to figure out how to max out your Roth IRA and also afford dinner, this episode’s going to walk you through what might be coming next—without promising you a yacht by Tuesday. This week on The Stacking Benjamins Show, Joe Saul-Sehy, O.G., and Doc G (Jordan Grumet) are joined by Nick Maggiulli, Chief Operating Officer at Ritholtz Wealth Management and author of Of Dollars and Data, to talk about lessons from his new book: The Wealth Ladder. Nick breaks down the six wealth levels, from scraping together your first emergency fund to navigating the complexities of generational wealth. They explore: Why increasing your income early on trumps frugality (sorry, coupon clippers). What “wealth plateaus” really look like, and how to recognize when your strategy needs to evolve. The hidden trap of goal obsession, featuring a cameo from world #1 golfer Sco

What’s the right financial move for you… right now? If you've ever found yourself reading advice meant for a millionaire when you're still trying to crack five figures—or following budgeting tips when your net worth is seven digits—this episode is your custom-tailored financial GPS. In this installment of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Doug take you rung-by-rung through the wealth ladder—from humble beginnings at $10K all the way to $10 million—and explain how your financial priorities, risks, and strategies evolve as your net worth grows. How to avoid mismatched advice: Why taking financial tips meant for someone in a different stage can set you back instead of move you forward. Net worth brackets and behavior shifts: What you should be thinking about at $10K, $100K, $1 million, and beyond—and what not to worry about yet. When Roth IRA conversions make sense—and when they really don’t: With new legislation impacting retirement tax planning, Joe and OG break down the implica

Ever feel like you're working hard but getting nowhere? You're not alone—and you might be stuck in a productivity trap, not a purpose-driven plan. In this episode of The Stacking Benjamins Show, we tackle the big one: how to avoid wasting your life. (No pressure.) Joe Saul-Sehy kicks things off with a tongue-in-cheek nod to all the ways we fritter away time—before pivoting into a power-packed conversation on building meaningful goals and avoiding common life derailers. He’s joined by two all-star minds in money and behavior: Paula Pant from Afford Anything, who reminds us that "you can afford anything—but not everything," and Jordan Grumet from Earn & Invest, who offers the life-and-death perspective (literally—he’s a hospice doctor) on why we need to act now, not later. Together with OG and Doug, the roundtable unpacks six common ways people unknowingly waste their lives, including: Being "busy" instead of effective Letting fear of failure hijack your plans Overthinking ever

Want to crush your goals and avoid getting crushed by long-term care costs? In today’s episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Retired Lieutenant Commander Gary McDermott, a former U.S. Navy officer turned business coach, who brings military-grade discipline to the world of goal-setting and financial success. Whether you’re working toward a promotion, launching a side hustle, or just trying to stay on track past February, Gary shares a field-tested, civilian-approved approach to achieving your biggest financial and personal milestones. From defining SMART goals to building sustainable habits and multiple income streams, this conversation is all about real results—no fluff, no buzzwords. But that’s just the first mission. In the second half, Joe and OG dive into one of retirement’s trickiest topics: long-term care insurance. Is it worth it? When should you buy it? How do you know if it’s right for your situation? Consider this your tactical briefing before walking into a ba

Still on track to crush your 2025 goals? Or has the year felt more like a Super Mario Kart banana peel moment? In this special mid-year review episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG take a pause from the summer sprint to look back at the most impactful lessons, conversations, and themes from the first half of 2025. Whether you’re rethinking your budget, fine-tuning your risk tolerance, or just trying to remember where you wrote down your resolutions, this is your nudge to hit the financial reset button—with style. From Alex Hormozi’s take on embracing risk and skill-building to JL Collins' wisdom on why buying happiness with money is a flawed formula, this episode pulls powerful insights from our brightest guests so far. We revisit career advice from media powerhouse Bonnie Hammer, dig into intentional spending habits, and reflect on the subtle connection between mindset and long-term success. Oh—and don’t miss a moment of Joe and OG’s always-wise, occasionally-weird banter as they br

Is your house full of stuff you thought you needed… but haven’t touched since the Obama administration? In this game show-style episode, we're helping you clean house and bulk up your bank account at the same time. Joining Joe in the basement are Paula Pant from Afford Anything, OG, and the man, the myth, the TikTok-famous legend’s grandpa’s best friend: Len Penzo (or as Doug calls him, “America’s Most Unexpected Influencer”). Together, they go head-to-head in a raucous showdown, each offering hot takes on everyday items you should stop buying if you want to save money and ditch the clutter. We dig into: Why some exercise equipment becomes expensive coat racks The hidden costs of seasonal decorations Periodicals, subscriptions, and other budget vampires And a few “who knew?” items that quietly drain your cash You'll also get a dose of trivia, debates about Google's "search decay," and a few personal stories that might sound a little too familiar. Whether you’re decluttering your