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 si...
Aug 22, 2025•59 min
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 generos...
Aug 20, 2025•1 hr 12 min
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 essenti...
Aug 18, 2025•58 min
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...
Aug 15, 2025•59 min
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...
Aug 13, 2025•1 hr 2 min
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...
Aug 11, 2025•59 min
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...
Aug 08, 2025•52 min
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 r...
Aug 06, 2025•1 hr 13 min
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 ...
Aug 04, 2025•1 hr 18 min
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...
Aug 01, 2025•1 hr 3 min
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, bes...
Jul 30, 2025•1 hr 21 min
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 ...
Jul 28, 2025•47 min
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 emotion...
Jul 25, 2025•58 min
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 Managemen...
Jul 23, 2025•1 hr 15 min
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 financi...
Jul 21, 2025•1 hr 5 min
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-s...
Jul 18, 2025•1 hr 6 min
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-...
Jul 16, 2025•1 hr 15 min
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 ...
Jul 14, 2025•1 hr 15 min
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 ...
Jul 11, 2025•59 min
What if your money could bring you more joy—and less stress? Today, we welcome Ken Honda, Japan’s bestselling personal development guru, to the basement. He introduces us to his concept of “Happy Money,” where gratitude replaces fear, and your relationship with money becomes… well, happier. From early lessons in emotional finance to wisdom from his own mentors, Ken shares how small mindset shifts can lead to big life changes. But before we get zen with our Benjamins, Joe and OG shine a light on ...
Jul 09, 2025•1 hr 11 min
Is your home packed with emotional baggage... and maybe a few fondue sets you haven’t touched since 2003? Organizational expert Tracy McCubbin joins us to talk about the emotional side of clutter—why it builds up, how it weighs us down, and what to do when your sentimental stuff is quietly running the show. Meanwhile, Joe and OG dig into another kind of mess: the billions retirees lose by claiming Social Security too early. Timing isn’t just everything—it’s the difference between thriving in ret...
Jul 07, 2025•1 hr 3 min
Happy Independence Day, Stackers! While fireworks boom and flags wave, we're lighting a spark under your financial life. This episode isn’t about tea in harbors—it’s about burning down debt, revolting against lifestyle creep, and rallying your family for a better money future. Joining Joe and Doug in the basement for this full-on financial insurrection: Dorethia Kelly , TikTok titan and money coach, shares how she raised her financial flag as a single mom and became a force for smart money choic...
Jul 04, 2025•1 hr 2 min
What does it take to turn a bold idea into a billion-dollar brand? Julie Wainwright, founder of The RealReal, joins us to share how she did just that—after enduring some pretty public failures (hello, Pets.com). She talks about navigating the startup world, tackling ageism head-on, and why your past doesn’t define your future. Julie’s story is packed with wisdom on risk-taking, confidence, and what it really means to build something new when everyone else is telling you no. From the boardroom to...
Jul 02, 2025•1 hr 6 min
How much can you really spend in retirement without running out of money—or worse, running out of fun? In this deeper-than-usual dive, Joe Saul-Sehy and OG examine the classic 4% retirement rule and whether it’s time for an upgrade. With new commentary from Bill Bengen, the original architect of the 4% rule, the team explores emerging research that suggests a withdrawal rate closer to 5.5% might be possible—if you’ve got the right mix of investments, a solid plan, and a bit of courage. But we do...
Jun 30, 2025•52 min
Can you really build wealth with a simple formula? Do you need a budget to succeed financially? Should you cut up all your credit cards, or is that just a dramatic TikTok trend? In this episode of The Stacking Benjamins Show , Joe Saul-Sehy is joined by Paula Pant, Doc G (Jordan Grumet), and Jesse Cramer for a roundtable discussion that peels back the truth behind popular advice from so-called financial “gurus.” The conversation is rooted in a provocative blog post by Christine Luken that calls ...
Jun 27, 2025•54 min
What’s the best way to save for a house without wrecking your retirement plan? That’s just one of the big questions Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle in this packed episode (number 1700!) of Stacking Benjamins . Whether you're trying to figure out where to park your emergency fund, how to handle inherited IRAs, or how to financially plan as a single adult with big responsibilities (hello, aging parents!), this episode is full of relatable scenarios and actionable strategies. Stac...
Jun 25, 2025•58 min
The robots aren’t just coming—they’re already here. And if you’re not paying attention, they might not just take your job… they could take your personal data too. In this episode of The Stacking Benjamins Show , Joe Saul-Sehy, OG, and Doug dive into the rise of artificial intelligence, exploring whether it’s a threat, a tool, or something in between. If you’ve been wondering how AI will impact your work, your privacy, and your future, this episode is a must-listen. They kick off with a surprisin...
Jun 23, 2025•53 min
So you’ve scaled the mountain, built the nest egg, and maybe even shouted “I’m done!” across a pristine beach... now what? In today’s Stacking Benjamins episode, Joe Saul-Sehy convenes a roundtable of heavy-hitters to tackle the most misunderstood phase of money management: decumulation —a.k.a. the art of spending what you’ve worked so hard to save. Whether you're staring down retirement or already deep into your golden years, you'll hear candid, practical insights from three financial thought l...
Jun 20, 2025•1 hr 24 min
What if the most important part of your retirement plan had nothing to do with your 401(k), IRA, or stock portfolio? In this episode of The Stacking Benjamins Show , Joe Saul-Sehy and OG are joined by filmmakers Pete Davis and Rebecca Davis, creators of the thought-provoking documentary Join or Die . They explore how community connection, not cash, may be the ultimate retirement strategy . Drawing inspiration from the late political scientist Robert Putnam ( Bowling Alone ), the Davises reveal w...
Jun 18, 2025•1 hr 4 min
You can’t plan a great retirement if you haven’t first planned what you’re retiring to. In this episode, Joe Saul-Sehy, OG, and Neighbor Doug open up Retirement Week in the basement with a Monday that’s equal parts insight, weekend recap, and questionable vehicle decisions. 🚪 Start with the most overlooked part of retirement: your lifestyle vision . What are you actually going to do all day—and will it make you happy? 📊 Then they dive into financial strategy , from coordinating pre-tax, Roth, ...
Jun 16, 2025•53 min
