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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

Be honest: When someone's talking to you, are you actually listening—or just waiting for your turn to speak? Joe Saul-Sehy and OG welcome executive coach Katie O'Malley, who's here to expose how terrible most of us are at paying attention—and more importantly, how to fix it. Whether you're trying to connect with your spouse, navigate a tough conversation with your kid, or just survive Thanksgiving dinner without the crypto uncle derailing everything, Katie's got the framework that makes you a better listener (and weirdly, a better decision-maker too).

Here's the thing: better listening doesn't just improve your relationships. It improves your money decisions. When you're actually present instead of distracted, you catch the details that matter. You ask better questions. You make choices that align with your values instead of reacting on autopilot. Katie breaks down the reflective listening technique that changes every conversation—at work, at home, and yes, even about money.

Joe and OG also dig into financial literacy for younger Stackers (because the skills you wish you'd learned earlier are the ones you should be teaching now), plus new research on all-stock portfolios and whether they're brilliant or just reckless depending on your risk tolerance.

And Doug? Doug's got Halloween-adjacent music trivia and commentary that reminds you not everything needs to be taken seriously.

What You'll Walk Away With:

• The reflective listening framework that immediately improves how you communicate (with everyone)

• Why "listening to respond" instead of "listening to understand" sabotages your conversations

• Simple techniques to break free from distraction loops—especially the ones involving your phone

• How better communication leads to better financial decisions (they're more connected than you think)

• What the research actually says about all-stock portfolios and whether they fit your risk tolerance

• Ways to teach young people the financial skills they need—even if nobody taught you

• Strategies for staying present during stressful family moments (holiday season, we see you)

Before You Hit Play, Ask Yourself:

• When was the last time you listened to understand instead of just waiting for your turn to talk?

• What relationships in your life would improve if you were actually present instead of mentally writing your grocery list?

• Are you teaching the young people in your life the money skills you wish someone had taught you?

• Does your investment strategy match your actual risk tolerance—or just what sounded good on TikTok?

• What uncomfortable conversations are you avoiding because you don't know how to navigate them?

Got a communication breakdown you're trying to fix—financial or otherwise? Drop it in the comments. The basement's got your back.

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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How to Actually Listen (Not Just Wait to Talk) SB1763

Pop quiz: If your health insurance premiums keep climbing, should you just go catastrophic and pocket the savings?

Joe Saul-Sehy, OG, and CFP Anna Allem tackle that exact question, along with a handful of other money decisions that keep Stackers up at night. From navigating healthcare coverage gaps to figuring out when (and how) to withdraw from a 529, this Monday mailbag episode is packed with the practical advice you need, served with the basement humor you've come to expect.

The health insurance conversation gets real: what catastrophic plans actually cover (spoiler: less than you think), how to plan for the gaps, and whether gambling on your health is ever a smart financial move. Then Anna breaks down the 529 withdrawal strategy that saves you headaches at tax time, and the crew tackles a listener who's spooked by market volatility and wondering if it's time to bail.

But it wouldn't be Monday without some chaos—Joe's cat decided to add drama to the morning, Doug brings trivia about counterfeit currency (because of course), and the gang updates you on the charity challenge where Stackers can support financial literacy and maybe win some prizes in the process.

Plus: OG delivers movie reviews to help you figure out what's actually worth your streaming time this week.

What You'll Walk Away With:

• The truth about catastrophic health plans—when they make sense and when they'll leave you exposed

• How to handle healthcare coverage gaps without gambling your financial future

• The smart way to withdraw from a 529 so you don't accidentally trigger taxes or penalties

• Why market volatility isn't a reason to panic—and what to do instead of bailing on your portfolio

• How diversification and rebalancing keep you sane when the headlines get scary

• A reminder that financial planning (like cat wrangling) rarely goes exactly as planned

This Episode Is For You If:

• You're staring at rising health insurance premiums and wondering if there's a better way

• You've got a 529 but aren't sure how to actually use it without screwing up

• Market dips make you nervous and you want to know if you should be doing something

• You're tired of generic financial advice and want real answers to your specific questions

• You believe learning about money should involve at least a few laughs (and maybe some cat stories)

Got a Question for the Basement?

Drop it in the comments or send it our way—you might just hear Joe Saul-Sehy, OG, and Anna tackle it in an upcoming mailbag episode. And if you want to support financial literacy while competing for prizes, check out the charity challenge details in the show.

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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Should You Actually Use a Catastrophic Health Plan? (& more questions from YOU!) SB1762

Ever feel like you're doing everything "right" with money—but still barely getting ahead? You're budgeting. You're saving what you can. You cut the subscriptions, meal prep on Sundays, and skip the daily latte. So why does it still feel like you're spinning your wheels?

In this Greatest Hits episode, Joe Saul-Sehy welcomes Erin Lowry (Broke Millennial), Paula Pant (Afford Anything), and Greg McFarlane (Control Your Cash) to tackle the question nobody wants to ask: What if the problem isn't your spending—it's your income?

Erin shares her journey from broke and stressed to financially stable and empowered, and the crew digs into why so many families struggle even when they're following all the "rules." Sometimes extreme budgeting isn't the answer. Sometimes you need to earn more. And yes, that's easier said than done—but this episode gives you the roadmap.

From practical strategies for saving for retirement when cash is tight, to negotiation tricks that lower your monthly bills, to the hilariously strange side hustles people actually do for extra money (you'll never look at classified ads the same way), this conversation is packed with ideas you can use today.

Plus: Classic basement banter, a "Spider Pig" serenade, Tony Romo's birthday, and all the tangents that make Stacking Benjamins feel like hanging out with friends who happen to know a lot about money.

What You'll Walk Away With:

• Why you might feel behind even when you're doing everything the experts tell you to do

• Erin Lowry's framework for moving from "broke" to financially confident (and why it's not just about willpower)

• When to focus on cutting costs vs. when to focus on earning more—and how to know the difference

• Practical retirement savings strategies that work even when your cash flow is tight

• Negotiation scripts for lowering your internet, phone, and other monthly bills (yes, they actually work)

• Creative (and sometimes bizarre) ways people make extra money that you've probably never considered

This Episode Is For You If:

• You're exhausted from budgeting and feel like you're sacrificing everything but still not getting ahead

• You wonder if you're just bad with money—or if something else is going on

• You've cut expenses as far as they'll go and need new strategies

• You're curious about side hustles but don't know where to start (or what's actually worth your time)

• You need a reminder that struggling financially doesn't mean you're doing it wrong—sometimes the system is just rigged

FULL SHOW NOTES: https://stackingbenjamins.com/stop-worrying-start-saving-greatest-hits-week-1761

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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Why You Feel Broke Even When You're Doing Everything Right (SB1761)

Here's what nobody tells you about building wealth: it's not about finding the perfect investment or timing the market. It's about doing boring things consistently until they're not boring anymore—they're just your life.

In this Greatest Hits episode, Joe Saul-Sehy and OG revisit a 2023 conversation with Jonathan Clements, the beloved former Wall Street Journal personal finance columnist and founder of Humble Dollar who passed away recently. We're resharing this episode to honor Jonathan's legacy, his gift for making complex ideas simple, and the joy he brought to every conversation about money.

Jonathan's book, My Money Journey, features 30 real stories from real people who built financial freedom—and the lessons are surprisingly simple (which doesn't mean easy). In this conversation, Jonathan breaks down what separated the people who made it from the people who kept spinning their wheels: steady habits, ruthless simplicity, and the kind of resilience that lets you keep going when life throws curveballs.

From emergency funds that actually saved people to the rent vs. buy debate that reveals more about your priorities than your budget, this conversation cuts through the complexity to show you what actually matters. Jonathan's wisdom feels even more valuable now—a reminder that the best financial advice isn't about chasing trends, it's about building a life that works for you.

Joe and OG also tackle listener questions, including whether to relocate for a better job and how to balance saving for tomorrow without sacrificing today. Plus: Doug's trivia, a Key & Peele-inspired TikTok minute, and proof that the best financial teachers leave lessons that last long after they're gone.

What You'll Walk Away With:

• The money habits that showed up in almost every success story from Jonathan's book (spoiler: none of them are sexy)

• Why simplicity beats complexity in investing—and how to stop overcomplicating your portfolio

• The rent vs. buy question reframed: it's not just about math, it's about what kind of life you want

• How to balance aggressive investing with the safety net you actually need (not the one Instagram tells you to have)

• Why emergency funds and health insurance are the unsexy heroes of every financial success story

• What "margin for error" really means—and why it's the difference between surviving setbacks and being destroyed by them

This Episode Is For You If:

• You're tired of chasing the next "hot" investment strategy and want to know what actually works

• You feel like everyone else has figured out money except you (spoiler: they haven't)

• You want to hear real stories from real people, not just theory from talking heads

• You're trying to balance living well now with saving for later—and feeling stuck in the middle

• You believe the best teachers are the ones whose lessons outlive them

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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Jonathan Clements: Why Simple Beats Complicated Every Time (SB1760)

Here's a wild idea: What if the thing holding you back isn't your bank account, your age, or your circumstances—it's just the story you've been telling yourself?

Joe Saul-Sehy and OG sit down with Colin O'Brady, four-time world record holder and endurance athlete who's done things most people would call impossible: solo trek across Antarctica, row across the Drake Passage, and yes, take a 12-hour walk that changed his entire perspective on what humans are capable of.

Colin's not just here to tell adventure stories (though those are incredible). He's here to talk about the mental game—the part where you convince yourself to take the first step even when the finish line seems impossibly far away. Sound familiar? Whether you're staring down a cross-country expedition or trying to figure out if you'll have enough saved for retirement, the challenge is the same: push past the voice that says "I can't" and prove to yourself that you can.

Then Joe and OG bring it back to the basement with a listener question about Roth vs. Traditional 401(k) contributions—because financial endurance is just as important as physical stamina. They break down how to think long-term about taxes, flexibility, and building a retirement plan that actually fits your life.

Plus: Neighbor Doug delivers trivia that proves even world record holders have to earn their laughs in the basement.

What You'll Walk Away With:

• What Colin O'Brady's 12-Hour Walk reveals about breaking through your mental limits (and how it applies to money decisions too)

• The mindset shift that separates people who attempt big goals from people who actually achieve them

• Smart strategies for balancing Roth and Traditional 401(k) contributions based on your timeline and tax situation

• Why flexibility matters as much as discipline—whether you're planning an expedition or planning retirement

• Permission to set goals that scare you a little (because that's usually where the good stuff happens)

This Episode Is For You If:

• You've been telling yourself you "can't" do something but wonder if that's actually true

• You want inspiration that comes with actual tactics (not just motivational fluff)

• You're trying to figure out the Roth vs. Traditional 401(k) question and want a clear answer

• You believe your best life is out there, but you're not sure how to build toward it

• You need a reminder that big transformations start with small, intentional steps

FULL SHOW NOTES: https://stackingbenjamins.com/conquer-your-mount-everest-greatest-hits-week-1759

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 a 12-Hour Walk Teaches You About Money (And Life) SB1759

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!

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

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!

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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

Tessa West has seen lots of people in the wrong careers. Either the job has drifted from what they'd initially thought, or maybe they're a leader at work, but they're passed over for promotions or raises. There are many reasons why people feel the malaise of a job that doesn't work anymore, but the effect is nearly always the same. Either you stagger through the work, wasting your life, or you dream about early retirement. What if there was another answer? What if the job that lights you up is actually out there? You need to know the tools to go find it. That's what Tessa Woods gifts us on today's show. You'll learn how to throw off the ennui and find meaning at work by either rebooting your current career or finding a new job elsewhere. We'll talk about how to engage in effective networking, how to assert yourself as a leader in your field, and why changing fields isn't a bad idea--even if you're an older worker. While many of us think that we wouldn't qualify for jobs against seasoned pros who've already had experience in the given area, Tessa shares how and why employers often want someone with a fresh perspective. You have to know how to sell your strengths, and we'll share some keys today.

In our headline segment, we'll review how Mark Cuban saved his fortune from disaster when everyone else lost money in the 2000-2002 tech wreck. We'll share the tools he used and how it all went down. Plus we'll answer the question: should YOU also use this strategy to avoid losses? It's a great question, and we tackle it head-on! We'll cover options, market declines, and the financial planning reasons Cuban executed this strategy.
FULL SHOW NOTES: https://stackingbenjamins.com/find-a-job-you-love-1549
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

Find The Work You'll Love (plus how Mark Cuban avoided losses during a market collapse)

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