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StackingBenjamins.com | Cumulus Podcast Network

Named the Best Personal Finance Podcast by Bankrate.com and Kiplinger, The Stacking Benjamins Show features a light and friendly tone. Hosts Joe Saul-Sehy and OG aim to make financial literacy fun for all as they sit around the card table in Joe's Mom's half-finished basement and talk with experts about personal finance, saving, investing, and important money trends. As Fast Company once wrote, the Stacking Benjamins podcast "strikes a great balance of fun and functional." So join Joe and OG every Monday, Wednesday and Friday as they read your letters, discuss major headlines, and throw in some trivia and laughs for free.

The Stacking Benjamins Show

Want to know what keeps retirees up at night? It's not what they did—it's what they wish they'd done ten years earlier.

Joe Saul-Sehy is joined by Jill Siriani (Frugal Friends), Jesse Cramer (The Best Interest), and Doc G (Earn & Invest), who all pull up chairs in the basement for a powerhouse roundtable on the five regrets that show up again and again when people hit retirement. These aren't hypothetical "what-ifs"—they're real stories from a real CFP, sharing tales about people who wished someone had told them sooner.

From botched investment allocations that left people either too risky or too conservative, to tax mistakes that cost tens of thousands, to the heartbreaking pattern of people who saved everything but never actually enjoyed their money—this conversation gets real about what actually matters when you're trying to retire with confidence (and joy).

The good news? Every single one of these regrets is avoidable. The panelists share what to do now so you don't become one of these stories later, including the estate planning moves that take ten minutes but save your family years of headaches, and why the biggest retirement regret isn't financial at all—it's emotional.

Plus: Doug's trivia challenge pits the panel against each other for bragging rights, because even serious money talk deserves a little competition.

What You'll Walk Away With:

• The five regrets that show up over and over in retirement—and the specific moves that prevent each one

• Why your investment allocation in your 40s and 50s might be setting you up for regret in your 60s

• Tax strategies that keep more money in your pocket (because giving Uncle Sam extra is nobody's retirement dream)

• The simple estate planning steps most people skip—and why your family will thank you for not skipping them

• How to give yourself permission to actually enjoy your money instead of hoarding it out of fear

This Episode Is For You If:

• You're decades from retirement but want to avoid the "I wish I'd known" moments

• You're closer to retirement and worried you've missed something important

• You want to hear top financial minds debate what actually matters (spoiler: they don't always agree)

• You're tired of generic retirement advice and want to hear what real retirees actually regret

• You believe retirement should be about living well, not just having enough

FULL SHOW NOTES: https://stackingbenjamins.com/top-5-retirement-plan-regrets-1758

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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What Retirees Wish They'd Known 10 Years Ago (SB1758)

Here's a question: If everyone's buying annuities right now, does that mean you should too?

Joe Saul-Sehy, OG, and Neighbor Doug tackle that exact question in this week's episode—but first, they're starting with the basics. Because before you can figure out complex financial products, you need to nail the fundamentals. And who better to teach them than Karen Holland, founder of Gifting Sense, who's made it her mission to help kids (and their parents) understand money in ways that actually stick.

Karen breaks down how to teach the next generation about "need vs. want," why middle schoolers need to understand the real cost of "cool," and how financial literacy can be empowering instead of intimidating. Whether you've got kids or just want a refresher on the money basics you wish someone had taught you, this conversation is the reset button you didn't know you needed.

Then things get timely: annuity sales are booming, and everyone's suddenly got an opinion. But are annuities the safe harbor they're marketed as, or just another way to lock up your money with fees you don't understand? Joe and OG cut through the sales pitch to help you figure out when annuities make sense—and when you're better off walking away.

Plus: Doug delivers "life-changing" trivia (his words), there's an iHeart Music Festival giveaway tied to financial literacy, and you'll get your weekly dose of basement wisdom served with laughs.

What You'll Walk Away With:

• Karen Holland's framework for teaching kids financial literacy that actually changes behavior (not just lectures that go in one ear and out the other)

• Why annuity sales are exploding right now—and the questions you MUST ask before signing anything

• The difference between annuities that solve real problems and annuities that just create expensive ones

• Financial habits that work at any age—whether you're teaching a 12-year-old or retraining yourself

• How supporting financial education can score you iHeart Music Festival tickets (because doing good shouldn't be boring)

This Episode Is For You If:

• You want to teach kids about money but don't know where to start (or worry you'll mess it up)

• Someone's pitched you an annuity and you're not sure if it's brilliant or a trap

• You've heard annuities are "safe" but want to understand what you're actually giving up

• You believe financial literacy is a gift worth giving—to your kids, your community, or yourself

• You want money advice that doesn't talk down to you or assume you already know everything

FULL SHOW NOTES: https://stackingbenjamins.com/raising-money-for-financial-literacy-1757

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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Financial Literacy for Kids + Are Annuities Actually Safe? SB1757

Nobody plans for their finances to get tight. But here you are, staring at your bank account, wondering if you should panic now or wait until next Tuesday. 

Joe Saul-Sehy, OG, and Neighbor Doug are here to talk you off the ledge—and give you an actual plan for when money gets squeezed. Whether you're facing a layoff, dealing with reduced hours, bracing through a government shutdown, or just trying to make your paycheck last until payday, this episode is your financial storm shelter.

The good news? You don't need to have everything figured out perfectly to make it through. You just need to know what to do first, what can wait, and how to keep your head (and your budget) together when everything feels uncertain. From building an emergency fund that actually works for your life to eating well on a ramen budget (spoiler: it's possible), this crew breaks down the practical moves that keep you afloat.

Plus: Doug delivers trivia, the gang tackles the Voices for Good Charity Challenge (because even in tough times, small acts of giving matter), and they dissect a TikTok money tip that's... well, let's just say not all financial advice should be followed.

What You'll Walk Away With:

• The first three moves to make when money gets tight—before the panic spiral starts

• How much emergency fund you actually need (hint: it's probably less than you think to get started)

• Budget-friendly tactics for groceries, utilities, and keeping yourself fed without living on instant noodles

• What to do about insurance and loans when cash flow slows down (and which mistakes cost you later)

• Why small acts of generosity matter even when you're struggling—and how they help you too

• A reminder that financial storms are temporary, but the skills you build weathering them last forever

This Episode Is For You If:

• Money feels tighter than it used to and you're not sure what to do about it

• You want to build a safety net but don't know where to start (or how much is "enough")

• The economy feels shaky and you want to feel prepared instead of panicked

• You're tired of generic advice like "just save more" and want actual tactics

• You need a pep talk wrapped in practical wisdom—because optimism without a plan isn't helpful

FULL SHOW NOTES: https://stackingbenjamins.com/the-importance-of-emergency-funds-1756

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

What to Do When Money Gets Tight SB1756

Pop quiz: What's scarier than a haunted house? Opening your credit card statement after a "just this once" shopping spree turned into a six-month spiral.

Joe Saul-Sehy and Neighbor Doug gather 'round the basement campfire with Doc G (Jordan Grumet from Earn and Invest), Jesse Cramer (Personal Finance for Long Term Investors), and special guest Emily Egashira—AKA Your Friend Em from TikTok and Instagram fame—to share the financial horror stories that still wake them up at night. We're talking ghostly car-leasing nightmares, investment decisions that refuse to stay buried, and the kind of money mistakes that haunt you long after Halloween is over.

But here's the thing about financial horror stories: they're only scary if you don't learn from them. Every tale in this episode comes with the lesson that could've prevented it—the red flag that got ignored, the advice that should've been followed, the moment when "this seems like a bad idea" got drowned out by "but everyone else is doing it."

From impulse purchases that turned into long-term regrets to the financial advice that sounded great... until it didn't, this crew proves that the scariest monsters aren't in the movies. They're in our bank accounts, our retirement plans, and that subscription we forgot to cancel three years ago.

Plus: Doug delivers Halloween trivia with a full-moon twist, because even financial terror deserves a side of fun.

What You'll Walk Away With:

• Real financial horror stories from people who lived to tell the tale (and learn from it)

• The common thread in most money disasters—and how to spot it in your own life

• Why car leases, "great investment opportunities," and "everyone's doing it" should always make you pause

• How to turn your own financial frights into lessons instead of letting them haunt you forever

• The confidence to say "no" when something feels off, even if you can't explain why

This Episode Is For You If:

• You've ever made a money decision you immediately regretted (welcome to the club)

• You want to learn from other people's expensive mistakes instead of repeating them

• You've got a financial skeleton in your closet and need to know you're not the only one

• You appreciate brutal honesty wrapped in humor—because laughing at financial pain is cheaper than therapy

• You're ready to face your money fears instead of hiding from them until tax season

FULL SHOW NOTES: https://stackingbenjamins.com/money-nightmares-wallet-portfolio-credit-1755

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Tales of Financial Horror (and how we exorcised them) SB1755

You know what's truly terrifying? Realizing you and someone you share money decisions with have completely different ideas about finances—and you're both convinced you're right.

Joe Saul-Sehy and OG welcome Doug and Heather Bonaparte, a CFP and business partner duo who've mastered the art of not killing each other over finances. And when you work together AND live together? Let's just say they've had plenty of practice navigating the financial frights that haunt any relationship where money's involved.

Whether you're married, dating, splitting rent with a roommate, or partnering on a business venture, the same money monsters show up: the "fair split" debates, the family expectation zombies that won't stay dead, and those vampiric spending habits that drain shared accounts when you're not looking. Doug and Heather share what actually works—the timing tricks, the tone shifts, and the teamwork strategies that keep financial conversations from turning into horror shows, no matter who you're talking to.

This isn't about becoming perfect financial partners overnight. It's about exorcising the money demons before they possess your most important relationships—romantic, professional, or otherwise.

Plus: Joe and OG stir the cauldron with Halloween movie talk and trivia, because even the scariest conversations are better with a little basement humor.

What You'll Walk Away With:

 How to start money conversations without summoning the spirits of past arguments (works for spouses, roommates, business partners, you name it)

 Doug and Heather's hard-won strategies for navigating disagreements when money and relationships overlap

 Why "financial transparency" isn't about policing every purchase—it's about understanding each other's money ghosts

 The three things any financial partnership needs to align on before the little stuff stops haunting you

 Permission to be messy while you figure this out (even CFPs have money fights)

This Episode Is For You If:

 You share financial decisions with ANYONE—a partner, roommate, business associate, or family member

 Money conversations feel like walking through a haunted house blindfolded

 Someone else's financial habits make you want to scream louder than a horror movie victim

 You're tired of being cast as the villain every time you want to discuss shared expenses

 You need proof that even professionals who literally do this for a living still have to work at it

FULL SHOW NOTES: https://stackingbenjamins.com/money-communication-horror-stories-1754

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Banishing Money Monsters: How to Talk Money With Anyone (Partners, Roommates, or Coworkers) SB1754

What's scarier than a haunted house? Looking at your retirement account after ignoring it for five years.

Joe Saul-Sehy, OG, and Doug welcome back Chuck Jaffe (Money Life with Chuck Jaffe) for his legendary annual Halloween visit—and this year, he's bringing two treats to the basement.

First up: Chuck's Halloween Money Game for kids. Picture this: trick-or-treaters can take one piece of candy and walk away... or they can play a game where they might win more candy, actual money, or lose it all. It's economics wrapped in a Snickers bar. Chuck breaks down how each choice teaches kids (and parents) about risk, reward, delayed gratification, and why sometimes the safe bet is actually the smart bet. If you've got kids—or just want a genius way to gamify money lessons—you'll want to steal this.

Then things get spooky. Real Stackers share their most bone-chilling financial horror stories: the credit union error that nearly cost someone their house, the coworker's "advice" that turned into a disaster, and the procrastination that haunted someone for years. These aren't fictional frights—they're real mistakes that real people are still recovering from. And every story comes with the lesson that could've prevented it.

Plus: Doug's trivia takes a Halloween turn (naturally), and Joe and OG debate whether government incentives are more trick or treat.

What You'll Walk Away With:

 Chuck Jaffe's brilliant Halloween Money Game—how to teach kids about risk, reward, and smart decisions using candy

 The economic principles hiding in every trick-or-treat choice (and how to explain them without killing the fun)

 Real Stacker horror stories: the financial mistakes that haunt people for years

 The red flags that could save you from starring in your own money nightmare

 Why the scariest financial advice often comes from people who mean well

This Episode Is For You If:

 You want a creative way to teach kids about money that doesn't involve a boring lecture

 You've ever made a financial decision you wish you could take back

 You want to learn from other people's mistakes instead of making them all yourself

 You've got a money skeleton in your closet and want to know you're not the only one

FULL SHOW NOTES: https://stackingbenjamins.com/frightening-halloween-stories-with-chuck-jaffe-1753

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Real Money Horror Stories (And How Not to Star in Your Own) SB1753

Here's a question nobody in the FIRE movement talks about: What if you reach financial independence... and don't want to quit?

Joe Saul-Sehy, OG, Paula Pant (Afford Anything), and Doc G (Earn & Invest) tackle the idea of Reverse FIRE—people who've hit their number but choose to keep working anyway. And before you roll your eyes, hear them out.

Because it turns out that having enough money doesn't automatically make you happy. And for a lot of people, walking away from work means walking away from purpose, identity, and the structure that kept them sane. The question isn't just "can I afford to retire?"—it's "what am I retiring to?"

This conversation gets real about the hidden costs of quitting too soon, why some financially independent people feel guilty for wanting to work, and how to think about retirement not as a finish line but as a design problem. Whether you're sprinting toward early retirement or secretly wondering if you'd be bored out of your mind, this episode will make you rethink what freedom actually looks like.

Plus: Doug's T-shirt trivia takes a weird turn (as always), and the crew proves that the best financial conversations happen when nobody's trying to sell you a course.

What You'll Walk Away With:

• Why "enough money" doesn't equal "enough purpose"—and what to do about it

• How to think about work after financial independence (hint: it's not all or nothing)

• The identity crisis nobody warns you about when you stop working—and how to avoid it

• What financially independent people actually do with their time (spoiler: many keep earning)

• Permission to want both: financial security and meaningful work

Before You Hit Play, Think About This:

If money wasn't an issue tomorrow, would you keep doing what you're doing? If the answer is "no"—why are you still doing it? And if the answer is "yes"—what does that tell you about retirement?

Drop your take in the comments. The basement wants to know: Are you racing toward FIRE, or are you building something you never want to leave?

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices

You've Got Enough Money to Quit. Should You? SB1752

Here's the secret nobody tells you: your money problems probably aren't math problems.

Joe Saul-Sehy and OG sit down with Carl Richards—financial planner, New York Times columnist, and the guy behind those brilliant "Sketch Guy" drawings that make money actually make sense. Carl's spent his career helping people untangle their relationship with money, and his big insight? Most of us are overthinking it.

Your financial plan shouldn't feel like a calculus final. It should feel like a map you can actually follow. Carl breaks down why emotions (not spreadsheets) drive most money mistakes, how to cut through the noise that keeps you paralyzed, and why the simplest plan is usually the one you'll actually stick to. If you've ever felt like you're "doing it wrong" because your strategy doesn't involve leveraged ETFs or cryptocurrency mining, this conversation will be a relief.

Then Joe and OG dive into the options trading debate. Is it a legitimate tool for managing concentrated stock risk, or just financial cosplay for people who watch too much CNBC? They break down when options might make sense, when they're just expensive complexity, and how everyday investors should think about them (if at all).

Plus: travel stories, Neighbor Doug's trivia (where he definitely brags about something), and proof that you can get smarter about money without wanting to take a nap.

What You'll Walk Away With:

 Carl Richards' framework for simplifying your financial life—and why "The Behavior Gap" matters more than your rate of return

 Why the emotions behind your money decisions matter more than the math (and how to work with them, not against them)

 How to filter out financial noise and focus on the handful of things that actually move the needle

 The truth about options trading: when it's a smart risk management tool and when it's just expensive gambling

 Permission to keep your plan simple—even if it feels like everyone else is doing something fancier

This Episode Is For You If:

 You feel like everyone else has figured out money except you

 Financial jargon makes you want to hide under a blanket

 You've got a solid income but still feel anxious about your money decisions

 You'd rather learn through real stories than get lectured by a guy in a suit

 You want to finally understand why you make the money choices you do (good and bad)

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-manage-your-money-goals-and-life-with-carl-richards-1751

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Your Money Problems Aren't Math Problems (They're People Problems) SB1751

You've got questions. We've got two CFPs and a former planner ready to hash it out.

Joe Saul-Sehy, OG, Doug, and CFP Anna Allem tackle the money decisions you're actually losing sleep over—and here's the thing: they don't always agree on the answer. That's the point.

Should you drain your emergency fund to pay off debt? Is whole life insurance for your kids a smart move or an expensive mistake? How much life insurance do you actually need (not what some calculator tells you)? And when life throws you a curveball—layoff, surprise expense, major purchase—what's the move?

With Joe Saul-Sehy's 16 years in financial planning, OG's CFP perspective, and Anna's insights, you'll hear how experienced voices think through these decisions differently—and why your answer might be different than all of theirs. Because the real skill isn't finding THE right answer; it's learning how to make YOUR right call.

This episode is for anyone who's ever stared at their bank account thinking, "I know I should do something... but what?"

Plus: Doug delivers trivia about the first auto insurance policy (because of course), the gang weighs in on athlete endorsements and reverse mortgages, and there's a TikTok money tip that sparks some debate.

What You'll Walk Away With:

• How experienced financial minds approach the emergency fund dilemma differently—and what that means for your situation

• The whole life insurance debate: when it makes sense for kids and when you're better off elsewhere

• A framework for figuring out how much life insurance you actually need—and why the "rules of thumb" don't always work

• What to do when your financial plan meets real life (layoffs, surprise bills, major purchases)

• The confidence to make a decision even when experts would handle it differently

Before You Hit Play, Ask Yourself:

What's the one money question you keep Googling but still don't feel confident about? If you're second-guessing your emergency fund, your insurance, or a big financial move, this episode is your permission to stop spinning and start deciding.

Got a question we didn't cover? Call in to the show! StackingBenjamins.com/Voicemail

FULL SHOW NOTES: https://stackingbenjamins.com/answering-your-burning-financial-questions-1750

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750

Think some people just have all the luck? Think again.

Joe, OG, Paula Pant (Afford Anything), and Chris Luger (Heavy Metal Money) break down what separates people who catch breaks from those who don't...and spoiler alert: it's not about being in the right place at the right time.

It's about what you DO when opportunity shows up. And before that: how you create the conditions for opportunity to find you in the first place.

This episode digs into three moves that make luck happen: staying curious (even when you think you know the answer), being generous (yes, it pays off financially), and staying flexible when life throws you a curveball. Whether you're stuck on a money decision, feel like you're missing opportunities, or just want to stop watching other people win, this conversation will shift how you see "luck."

Plus: Doug's trivia gets weird (what even IS a buttload?), the gang debates pumpkin spice season, and you'll hear stories that prove the best financial wins rarely go according to plan.

What You'll Walk Away With:

 The one thing "lucky" people do that creates more opportunities—and how to start doing it today

 Why helping others might be your best financial strategy (and the science behind it)

 How to spot opportunities you're currently walking past

 What to do when your financial plan falls apart (hint: the flexible win)

 Permission to try something new, even if you're not sure it'll work

Before You Hit Play, Think About This:

What's one time something good happened to you? ...not because of random chance, but because you were curious, helped someone, or said yes to something outside your comfort zone? That's the kind of "luck" we're talking about.

Got a story? We want to hear it. Drop it in the comments or share it in your podcast app.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-find-more-luck-with-your-money-1749

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

Enjoy!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

What Lucky People Do Differently With Money (SB1749)

Choosing the Best Tax Software for Your Needs
Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution.

Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year.

H&R Block’s virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to.

Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions.

Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table.

Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix.

Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations.

If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence.

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!
Learn more about your ad choices. Visit podcastchoices.com/adchoices

The Best Tax Prep Software of 2025 (SB1655)

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