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StackingBenjamins.com | Cumulus Podcast Network

The Stacking Benjamins Show

Do you dream of conquering your financial goals and achieving true financial independence? In this episode, we’re diving into five BIG mistakes people make along the way to financial glory with money coach Bernadette Joy, who paid off a staggering $300,000 in debt and locked in a work-optional life by age 40.
Along the way, we’ll explore the importance of managing your budget during the notoriously tricky holiday season, share actionable strategies to curate your accounts, and highlight the common mistakes that can derail even the best-laid financial plans. You’ll also hear the wild story of Richard Whitaker, whose pursuit of a too-good-to-be-true 15.25% return serves as a cautionary tale for us all.
Whether you’re looking to tackle debt, sharpen your budget, or avoid financial scams, this episode is packed with insights to help you stack smarter.
Episode Highlights

Kicking off with weekend escapes, Monday blues, and a salute to the armed forces

Nostalgic nods to Chitty Chitty Bang Bang

Welcoming Bernadette Joy and diving into her inspiring journey to financial freedom

Sharing personal stories and struggles that resonate with every money nerd

Breaking through financial barriers on the path to independence

Setting financial goals with inspiration from meeting Simone Biles

Why comparing success stories can derail your progress

The delicate dance between frugality and societal expectations

Staying grounded amidst the curated realities of social media

Avoiding the common mistake of giving unasked discounts

Why accepting debt as a long-term lifestyle is a trap

Choosing financial freedom over fear and hesitation

The importance of diverse perspectives in your financial advisory team

Preparing for the unexpected: Life events that test your financial foundation

Exploring and questioning investment opportunities like Yield Wealth

Understanding the gambler’s mentality and how it can lead to downfall

Practicing due diligence to avoid falling for scams

Lessons learned from the downfall of Yield Wealth and how to protect yourself

Announcements about upcoming events and opportunities to connect

This episode is a mix of relatable stories, practical advice, and lessons learned the hard way. Tune in to start crushing your money goals and avoiding financial pitfalls—one smart decision at a time.
FULL SHOW NOTES: https://www.stackingbenjamins.com/crush-your-2025-money-goals-bernadette-joy-1613
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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Do These 5 Financial Mistakes Sound Familiar? (SB1613)

It’s a Festivus for the rest of us! This week, we’re mixing holiday cheer with must-know insights to keep your season merry, bright, and worry-free. Steve Kerber joins us from the Fire Safety Research Institute, who shares life-saving fire safety tips just in time for all those twinkling lights and candles. Because the best insurance is prevention, right? This year we're chatting about lithium-ion batteries and how explosive (literally) these can be for your holiday season if you aren't careful. We'll also chat about smoke alarms, closing your doors, and having an emergency exit plan in place!
But that’s not all—we’re also diving into why big Wall Street players are taking out loans they don’t need and how you can apply creative financing strategies to your own life. Plus, we answer a listener’s estate planning question that came up during their bedtime reading (we love multitasking). Sprinkle in some holiday trivia, debates over the best Christmas movies, and discussions on revocable trusts, and you’ve got a variety-packed episode that’s as fun as it is informative.
Episode Highlights:

Holiday fire safety tips from Steve Kerber, including new standards for smoke alarms and tips for handling lithium battery hazards.

Why having a solid fire escape plan is the ultimate prevention strategy.

How Wall Street’s creative financing trends can inspire you to rethink debt and financial flexibility.

Strategies for analyzing and managing debt like a CFO, just in time for the New Year.

Listener Q&A on estate planning, with practical advice on revocable trusts and holistic financial planning.

Holiday trivia, featuring quirky debates about the best Christmas movies—spoiler alert: “Die Hard” might come up.

Why You’ll Love This Episode:
It’s not every day you get a mix of life-saving fire tips, actionable financial strategies, and festive fun in one show. Whether you’re looking to keep your home safe, optimize your finances, or just get a good laugh, this episode has something for everyone.
Resource Mentioned:
BatteryFireSafety.org

FULL SHOW NOTES: https://stackingbenjamins.com/fire-safety-tips-2024-steve-kerber-1614
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Don’t Forget:
Tell us your favorite holiday movie! Share your pick in the Basement Facebook group or tag us on social media. Who knows—you might just settle the debate once and for all.
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Holiday Ready? Essential Fire Safety to Save Lives and Cash! (SB1614)

If your bank account is thriving, but your soul feels bankrupt, are you really living your best life?
Today we dive into the deep end of personal finance, tackling life's biggest questions. The discussion starts with festive neighborly rivalries (think over-the-top decorations and holiday antics) but transitions pretty quickly into an emotional exploration inspired by a powerful piece written by Jonathan Clements for his Humble Dollar blog. Reflecting on his cancer diagnosis and thoughts on mortality, Clements’ writing serves as a springboard for a candid roundtable chat about regrets, risk, and how to make the most of our limited time.
With additional insights from Paula Pant and Doc G, this episode is all about helping you live purposefully while keeping your financial house in order.
Why You’ll Love This Episode:

Explore how to balance financial strategies with meaningful life choices.

Gain perspective on managing regrets and making peace with life’s uncertainties.

Discover why generosity and appreciating the little things are the ultimate forms of wealth.

Episode Highlights:

Holiday hilarity: Over-the-top decorations, fish sticks, and birthday antics.

Jonathan Clements’ reflections on mortality and embracing the present moment.

Paula Pant and Doc G’s insights on purposeful living and financial balance.

Strategies for managing risk, reward, and estate planning challenges.

The transformative power of generosity and savoring simple joys.

Trivia Fun:
It’s the final trivia showdown of the year! Can OG claim victory, or will this be another epic trivia blunder? Tune in for the the guesses, and a few surprising facts.
Takeaways to Ponder:
Jonathan Clements’ reflections remind us that while building wealth is essential, so is living a life filled with purpose, generosity, and connection.
Resources Mentioned:

Jonathan Clements’ Humble Dollar Blog Post: The C Word

Stacking Benjamins Book Club is Open!

Join the Basement Facebook Group

Let’s Keep the Conversation Going:
What’s your secret to balancing finances with a life well-lived? Share your thoughts with us in the Basement Facebook group, or tag us on social media.
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What Truly Makes a Life Worth Living? SB1615

Ever feel like you’re your own worst enemy when it comes to reaching a goal? Today, we sit down with Thais Gibson from the Personal Development School to explore how self-sabotage sneaks into our lives and—more importantly—how to kick it out for good. While you've maybe heard Thais on Mel Robbins or other shows, what you haven't heard is what we talk about today - how specifically she walks Joe through limiting beliefs and then outlines how it's done. Whether you've followed Thais' huge social media presence consistently or it's your first time with her, we know this will help you kick self-sabotage to the curb and get to work. From aligning your conscious and subconscious goals to overcoming limiting beliefs, this conversation is packed with actionable insights to help you get out of your own way.
But that’s not all. We also dive into a financial hot topic: influencer-backed crypto scams. Learn how a viral coin duped investors last week and why speculation isn’t the same as smart investing.
Of course, it wouldn’t be a Stacking Benjamins episode without some holiday flair. Joe, OG, and Doug share festive mall memories, debate the best holiday tunes, and throw in some trivia to keep things lively.
Why You’ll Love This Episode:

Practical tips to recognize and overcome self-sabotage.

Eye-opening lessons on speculative investments and influencer-driven hype.

A nostalgic take on holiday mall culture. Remember that?

Episode Highlights:

Kicking off with holiday concerns and a satirical take on seasonal trends.

Festive mall memories: shopping chaos, holiday tunes, and the art of people-watching.

Thais Gibson’s insights on aligning conscious and subconscious goals to beat self-sabotage.

Turning resistance into opportunities and tackling the emotional costs of inaction.

Practical steps to rewire limiting beliefs and visualize success.

Lessons from a viral influencer’s crypto scam and the dangers of speculative investing.

Speculation vs. investing: Why it matters and how to avoid costly mistakes.

Holiday trivia fun and laughs with the Basement crew.

What You’ll Take Away:
Whether you’re looking to improve your mindset, steer clear of financial pitfalls, or just enjoy some holiday tunes, this episode offers a little something for everyone. Walk away with tools to set yourself up for success—mentally, financially, and maybe even musically (if Doug’s favorite holiday tune is your jam).
Keep the Conversation Going:
Have a story of self-sabotage you’ve overcome or a holiday memory to share? Join us in the Basement Facebook group to swap tips, laughs, and maybe a little holiday cheer.
FULL SHOW NOTES: https://www.stackingbenjamins.com/stop-self-sabotaging-thais-gibson-1616
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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Ever Wondered Why Success is Just Out of Reach? (SB1616)

Feeling like your wallet’s taking a holiday beating? Don’t sweat it. We’ve got eight clever strategies to keep your spending in check and set yourself up for a financially stronger new year.
But wait—there’s more! We uncover the mind-blowing story of a 29-year-old living large in a mansion filled with luxury cars and Elton John's piano. What's his secret? (Hint: It’s not what you’d expect.)
And because we love answering Stackers' burning questions, we tackle a double feature:

Pensions: Are they still worth the hype?

Should you pay off your mortgage before retirement?

Sprinkle in some holiday stress hacks, thoughts on budget-friendly gift-giving, and why Tony the Tiger has something to do with the Grinch, and you've got a show packed with financial wisdom you can actually use.
Episode Highlights

How the Grinch Really Stole Christmas

Welcome to the Stacking Benjamins Show

Is Your Holiday Budget Already on Thin Ice?

8 Strategies to Tame Holiday Expenses

A Mansion, Luxury Cars, and Elton John’s Piano?

Handling Holiday Stress Without Losing It

Travel Plans & Navigating Holiday Spending

How to Leverage Debt (the Smart Way)

Get Kids Involved in the Budget—Yes, It’s Possible

Starting a 529 Plan? Why Family Might Help

Gift Strategies That Won’t Break the Bank

Today’s Date in History: Because Why Not?

TikTok Minute: The Mansion Story That Broke the Internet

Listener Questions: Pensions vs. Mortgages

Corrections Dept: Football Teams Need a Map

Final Thoughts and Big Takeaways

Whether you're taming holiday expenses, dreaming of mansion living, or just trying to get through December with your finances intact, this episode's got something for you. Tune in, take notes, and finish the year strong.

FULL SHOW NOTES: https://www.stackingbenjamins.com/sticking-to-your-financial-goals-during-holidays-1617/
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Eight Strategies to Conquer Holiday Budget Overload (SB1617)

As 2024 winds down, we’re taking a look back at the year that was—its challenges, its surprises, and the financial lessons we’ve all had to learn (sometimes the hard way). Whether you’re strategizing for big goals in 2025, making sense of unpredictable markets, or just trying to stay one step ahead of inflation, this episode has you covered.
We’ve assembled a powerhouse panel of financial thinkers—OG, Paula Pant, and Jesse Cramer—to break it all down. Together, they tackle everything from the unpredictable influence of AI on markets and investing to the surprising resilience of real estate in the face of rising interest rates. Plus, they explore the year’s most intriguing (and occasionally jaw-dropping) headlines, like the impact of significant economic shifts and even the infamous United Healthcare CEO murder.
Why You’ll Want to Tune In:

Discover how 2024’s biggest events, including the AI revolution and shifting inflation trends, impact your wallet.

Learn why patience and adaptability are critical tools for navigating market volatility.

Get actionable strategies for tackling real-life financial challenges, like managing interest rates and planning for 2025.

Episode Highlights:

Reflecting on the big financial lessons of 2024: From AI in market behavior to Bitcoin’s latest chapter.

How the crypto craze evolved this year—and what it means for the future.

The ongoing unpredictability of investing and how to stay grounded.

Surprising lessons from corporate America’s headlines, including shocking events like the United Healthcare CEO murder.

Inflation, real estate, and housing market realities: What it all means for your plans in 2025.

How AI is reshaping everyday life, job markets, and even podcasting.

Our Panel’s Key Takeaways:
OG shares portfolio management strategies to help you ride out market uncertainty.
Paula Pant unpacks real estate trends and the importance of designing a life you love.
Jesse Cramer dives into how behavioral finance plays into today’s fast-changing landscape.
Looking Ahead:
As we close out another exciting year of The Stacking Benjamins Show, we want to thank you, our loyal Stackers, for joining us on this journey. In 2025, we’re bringing even more fresh takes, insightful interviews, and, of course, the best money advice disguised as good conversation.
What’s Coming in 2025:
We’ll dive into the latest financial trends, explore groundbreaking stories, and keep helping you make smarter money moves while keeping it entertaining. Stick with us as we continue stacking those Benjamins—and maybe even have a little fun along the way.
Thank you for being part of the Stacking Benjamins community. Here’s to another year of learning, laughing, and leveling up your financial life!
FULL SHOW NOTES: https://stackingbenjamins.com/2024-year-end-review-1618
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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Did 2024 Just Rewrite the Rules of Investing? (SB1618)

The holiday season is here, and while it’s a time for celebration, it can also throw a curveball at your health and financial goals. In this episode, we’re joined by Angelo Poli from MetPro, who shares his no-nonsense approach to managing holiday indulgences without sacrificing all the progress you’ve made. Think of it as building a resilient portfolio—you can enjoy the party but still limit the downside.
From understanding your metabolism to navigating holiday feasts and weight loss medications like Ozempic, Angelo offers practical strategies to keep your health on track while enjoying the season. But we’re not stopping there. We also dive into estate planning essentials, including a cautionary tale about a video will gone wrong (yes, even your estate plan needs a solid foundation).
And what’s a holiday episode without some laughs and trivia? We round out the show with listener questions, Nick from the North’s budget dilemma, and a fun discussion about flying around the world.
What You’ll Learn Today:

Smart strategies for balancing holiday cheer with health goals, including tips for managing alcohol and indulgent foods.

How to leverage your metabolism for better weight management.

The truth about weight loss medications and their real-life impact.

Why estate planning matters more than ever in the digital age—and how to avoid common pitfalls.

Practical advice for navigating holiday spending without blowing your budget.

Episode Highlights:

Reflecting on how fast time flies and gearing up for the holidays.

Angelo Poli’s top tips for keeping holiday indulgences in check.

Breaking down myths about weight loss medications and the importance of behavior over quick fixes.

Estate planning essentials, including lessons from a case where a video will was invalidated.

Fun banter, trivia, and Nick from the North’s relatable holiday budget dilemma.

Why You Should Listen:
This episode is a must for anyone juggling holiday festivities with long-term goals. Whether you’re strategizing for your health, wealth, or estate plan, you’ll find actionable advice wrapped in a festive package. Plus, it’s always good to know how to enjoy the season without feeling like you’ve set yourself back.
Take control of your holiday season and start stacking those Benjamins—without sacrificing the things you enjoy most.

FULL SHOW NOTES: https://stackingbenjamins.com/balancing-holiday-cheer-with-your-long-term-goals-1619
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

Balancing End of Year Cheer With Your Long Term Goals (SB1619)

What happens when Doug gets visited by three ghosts in the basement? A classic holiday story gets a Stacking Benjamins twist in this special episode. Inspired by A Christmas Carol, we explore lessons from the past, present, and future to help you make smarter money moves.
From learning to avoid past financial missteps to balancing life’s experiences with your financial goals, this episode blends memorable storytelling with practical advice. Along the way, Joe, OG, and Doug serve up clever banter, unexpected insights, and strategies you can put into action to ensure your finances stay merry and bright.
What You’ll Learn Today:

How reflecting on financial mistakes can help shape smarter decisions.

The importance of balancing money with life experiences in the present.

Why intentionality and automation are the secret weapons for future financial success.

Practical strategies to avoid the consequences of inaction.

Episode Highlights:

The team kicks off by debating the best versions of A Christmas Carol.

Doug’s journey begins with a visit from the Ghost of Christmas Past, offering lessons on overcoming financial missteps.

The Ghost of Christmas Present emphasizes being mindful of your current financial habits and enjoying life without overindulgence.

The Ghost of Christmas Future shows why planning and automating your finances now can save you from future regret.

Practical advice on setting short- and long-term goals, creating financial intentionality, and balancing fun with financial responsibility.

Why You Should Listen:
If you’ve ever felt haunted by past money decisions, unsure about how to balance saving with spending, or overwhelmed by future financial planning, this episode is for you. It’s a thoughtful, engaging, and surprisingly relatable take on holiday classics—with plenty of tips to ensure your financial wellness story has a happy ending.
Gather around, grab some eggnog, and join us for a holiday tale that’ll leave you inspired to tackle your finances with clarity and purpose.
FULL SHOW NOTES: https://www.stackingbenjamins.com/doug-and-the-three-ghosts-1620
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

Doug and the Three Ghosts: A Financial Holiday Tale (SB1620)

How can kindness and a little math transform not just a company but an entire outlook on life? In this episode, we’re joined by James Rhee, who shares his remarkable journey from venture capitalist to CEO of a company dedicated to inclusivity and empowerment for plus-size Black women. James opens up about the values instilled by his Korean immigrant parents, the challenges of reviving a struggling business, and how empathy and cultural understanding can create impactful, lasting change.
James also shares his leadership philosophy, emphasizing the power of kindness in decision-making and the surprising role of math in driving meaningful progress. From the red helicopter story to his thoughts on the importance of liberal arts education, James’ perspective is a refreshing reminder that true success starts with leading from the heart.
On the financial side, Joe and OG tackle a listener’s question about mortgage recasting, explaining the differences between lowering monthly payments and paying down principal, and why understanding your financial goals is crucial. They also dive into wedding spending trends, including tips for managing costs without sacrificing the celebration.
And because it’s the holiday season, the episode wouldn’t be complete without warm, festive stories. Joe and OG reminisce about early Christmas mornings, favorite holiday traditions, and the unexpected joys of giving (and receiving).
What You’ll Learn Today:

Leadership lessons from James Rhee, including the role of kindness and cultural understanding in personal and professional success.

How recasting a mortgage works, when it makes sense, and how to align it with your goals.

Practical strategies for managing wedding budgets and navigating the financial burden of attending events.

Why intentionality is the key to handling major financial milestones.

Episode Highlights:

James Rhee’s journey from venture capitalist to CEO and his focus on empowering plus-size Black women.

The power of kindness and math in leadership, with personal stories from James’ upbringing and career.

Wedding spending trends, budgeting tips, and financial advice for planning big events.

Joe and OG’s take on mortgage recasting and how to approach it strategically.

Festive Christmas morning memories and holiday traditions.

Why You Should Listen:
Whether you’re looking for leadership inspiration, practical financial advice, or just a little holiday cheer, this episode has something for everyone. James Rhee’s story will leave you inspired to lead with kindness, while Joe and OG’s financial insights will help you tackle your goals with confidence—and maybe a few laughs along the way.
Kindness and intentionality can change your finances—and your life. Tune in to this inspiring episode and make it a holiday season to remember.
FULL SHOW NOTES: https://www.stackingbenjamins.com/beyond-the-numbers-james-rhee-success-through-kindness-greatest-hits-1621/
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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Beyond the Numbers: James Rhee's Recipe for Success through Kindness (SB1621)

For this next installment to this edition of our Greatest Hits Week, we throw it back to a conversation Joe had with Zoe Chance about how to make influence your superpower.
Do you ever feel like you just don’t have much influence over others? Not in a negative way, but in a way where you wish people would truly hear you. Sometimes we just need to take a step back and re-evaluate what we are trying to accomplish. Zoe Chance is an expert in influence and is an Assistant Professor at Yale. She joins us today to share her secrets to positive influence and happiness. She talks about the power of ‘no’, charisma, and my favorite, the Kindly Brontosaurus technique.
During our headline segment, we dive into longevity in financial planning. As people start living longer, what adjustments need to be made to financial plans? We talk about retirement planning and allocations as it relates to living longer lives. We also help answer Jenna’s question about saving or spending HSA dollars and Doug shares his influential trivia.
This episode originally aired on February 23, 2022. Please disregard any mention of current events.
FULL SHOW NOTES: https://www.stackingbenjamins.com/make-influence-your-superpower-greatest-hits-week-1622/
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

Zoe Chance Shows You How Influence Is Your Superpower (SB1622)

How do you go from a struggling actor to the top of the real estate world? Rounding out our greatest hits week of epic shows, we time travel back to when Ryan Serhant, star of Million Dollar Listing New York and the new Netflix series Owning Manhattan, shared his journey from rock bottom to building a billion-dollar real estate empire. In this episode, Ryan reveals how juggling multiple priorities, embracing initiative, and even practicing improv can transform your sales game and your life.
But that’s not all! We also dive into using reward points for 529 plans, the risks of banking perks, and how to balance saving for college with planning for retirement. Along the way, we sprinkle in stories, insights, and a little basement-style charm to keep you engaged.
Here’s what we cover:

Ryan Serhant's pivot from struggling actor to real estate mogul

Sales tips, including the art of listening and making friends quickly

Why improv can make you a better salesperson

Insights from Ryan's new Netflix series, Owning Manhattan

Lessons from Tiger Woods and other high performers

Reward points and their role in funding 529 plans

The potential pitfalls of banking perks

Balancing college savings with retirement goals

Emergency funds and FAFSA tips

Whether you’re looking for career inspiration, financial insights, or a reason to laugh, this episode has you covered. Tune in and stack your knowledge with us!
FULL SHOW NOTES: https://www.stackingbenjamins.com/zero-to-million-dollar-listings-ryan-serhant-greatest-hits-week-1624/
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

Building a Billion Dollar Empire with Ryan Serhant (SB1624)

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