The Stacking Benjamins Show

Think the American Dream is slipping out of reach? Think again. In this episode of The Stacking Benjamins Show , Joe Saul-Sehy , OG , and Neighbor Doug tackle one of the biggest financial questions of our time: how much does it really cost to live the life you want — and is it still possible? Spoiler alert: it is, but it takes more than a paycheck and a Pinterest board. We break down fresh researc...

What if tweaking just a few “knobs” in your 401(k) could mean the difference between retiring with confidence or wondering if you’ll ever stop working? In this spirited episode of The Stacking Benjamins Show , Joe Saul-Sehy , OG , and Neighbor Doug are joined by three of our favorite money minds — Paula Pant from AffordAnything , Jesse Cramer from Personal Finance For Long Term Investors , and Lac...

What if the secret to enjoying your job isn’t grinding harder but stepping back and rethinking how work fits into life? In this episode of The Stacking Benjamins Show , Joe Saul-Sehy , OG , and Neighbor Doug welcome special guest Shemin Nurmohamed to unpack the Paris Paradox: balancing work and leisure without sacrificing ambition. From cultural perspectives on downtime to the productivity perks o...

Ever make a money move in the heat of the moment and wish you could take it back? That’s exactly why a rock-solid Investment Policy Statement (IPS) might be your most underrated financial tool. In this episode, Joe Saul-Sehy , OG , and Neighbor Doug peel back the layers on IPSs—why they matter, how they save you from your own impulses, and the role they play in making sure your investment strategy...

What happens when you throw a bunch of money nerds into one room, add microphones, and sprinkle in a little economic chaos? You get this live recording from FinCon in Portland , where Joe Saul-Sehy , Paula Pant , Jesse Cramer , and Matthew Tarr tackle today’s most pressing financial questions head-on—with plenty of laughs along the way. From housing headaches to healthcare hurdles, nothing is off...

What happens when you stop playing it safe and start playing it smart? In this episode, Joe Saul-Sehy , OG , and Neighbor Doug sit down with David Gardner , co-founder of The Motley Fool , to explore how breaking traditional investing “rules” can sometimes lead to the biggest wins. From his early career to building a community of investors who think differently, David shares the lessons that shape...

What really derails retirement dreams? Spoiler alert: it’s not always the stock market or your 401(k). Sometimes it’s sneaky habits—like leaning too hard on your house as a retirement plan or ignoring how long you might actually live—that quietly gnaw away at your financial future. In this episode, Joe Saul-Sehy , OG , and Neighbor Doug dig into the most common middle-class retirement killers and...

If having more money guaranteed happiness, we’d all just set our financial targets, cash the checks, and live joyfully ever after. But as Joe Saul-Sehy , OG , Paula Pant ( Afford Anything ), and Joel Larsgaard ( How to Money ) unpack in this lively roundtable, life’s richest rewards often have little to do with your net worth. They explore why some wealthy people still feel miserable, how Benjamin...

What can you learn about leadership from someone who’s served four U.S. Presidents, navigated some of the most intense moments in American politics, and still believes the future depends on building more leaders, not fewer? In this Greatest Hits Week replay, Joe Saul-Sehy , OG , and Neighbor Doug welcome David Gergen —former White House advisor, Harvard professor, and author—to the basement for a...

Not all financial advisors are created equal—and some will steer you straight into the rocks while smiling the whole way. In this episode of The Stacking Benjamins Show , Joe Saul-Sehy , OG, and Neighbor Doug share the top five warning signs your advisor may not have your best interests at heart. From shady investment recommendations to fee structures that deserve a magnifying glass, we unpack the...

Ever celebrate paying off a credit card…only to watch your credit score drop? Or ditch your budget for “simplicity” and find yourself ordering takeout three nights in a row? On this week’s episode of The Stacking Benjamins Show , Joe Saul-Sehy , OG , and Neighbor Doug welcome Paula Pant ( Afford Anything ) and Jesse Cramer ( Personal Finance for Long-Term Investors ) to explore why even the “right...

What happens when you hand the mic to Stackers? You get a mailbag episode loaded with real-life money challenges, surprising lessons, and a few “wait, what?” moments. Joe Saul-Sehy , OG , special guest Anna Allem (a CFP® with her own winding journey into the profession), and Neighbor Doug dig into your most pressing financial questions—no fluff, no jargon, and definitely no shortage of basement-st...

Labor Day might be about rest, but in the basement, we’re getting to work on busting some of the most persistent myths in personal finance. Joe Saul-Sehy and OG welcome insurance pro Tony Steuer to unpack the shiny marketing around infinite banking and velocity banking. Spoiler: sometimes “be your own bank” really means “make your insurer rich.” From permanent life insurance pitfalls to the real m...

Why wait until your knees creak louder than your rocking chair to start enjoying life? In this episode, Joe Saul-Sehy, OG, Paula Pant (AffordAnything) and Neighbor Doug welcome Jillian Johnsrud—author of Retire Often —to share why sprinkling your life with mini-retirements might be the smartest, healthiest, and most joyful move you make before your “official” retirement date. Think of it as giving...

If you’ve been running on fumes, juggling work deadlines, family obligations, and maybe even a neglected 401(k) or two, this episode is your permission slip to stop, breathe, and recalibrate. Joe Saul-Sehy, OG, and Neighbor Doug welcome Dr. Danielle McGeough—professor, transformational strategist, and champion of intentional living—into the basement for a conversation that’s part burnout intervent...

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 sche...

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....

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...

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 i...

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 aimin...

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...

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. St...

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 st...

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”...

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 dri...