Episodes

  • Ready to brave the Black Friday madness? Don’t hit “add to cart” just yet! In this episode, tech guru Bridget Carey from CNET joins us to share her insider tips on navigating the sea of deals and avoiding those flashy-but-fishy doorbusters. Whether you’re hunting for the latest gadgets or trying to resist that smart fridge you probably don’t need, Bridget’s advice will save your wallet (and maybe your sanity).
    But that’s not all! We’re diving into why mortgage rates are still climbing even as the Fed cuts interest rates, what it means for your financial plans, and whether paying off your mortgage early is worth the hype. Along the way, we sprinkle in personalized money moves, tech nostalgia, and even some surprising theme park innovations (hint: the future is now, and it’s a little quirky).
    It’s an episode jam-packed with expert advice, a few detours into saxophone mysteries, and practical tips to keep your finances (and holiday shopping) in check.
    Run of Show

    Black Friday Tech Talk: Introduction and Welcome

    Thanksgiving Prep and Family Traditions (a.k.a. Stuffing Debate #4,567)

    Tech Gadgets You Want vs. Gadgets You Actually Need

    Bridget Carey’s Tech Wishlist and Recommendations

    AI in Everyday Tech: The Good, the Bad, and the Overhyped

    Apple Products and Innovations: Must-Have or Meh?

    Fun and Quirky Tech Toys to Impress Your Inner Child

    Theme Park Tech Updates: The Future of Fun

    Star-Studded Party Details: Who Brought the Mystery Saxophone Player?

    Mortgage Rates and Why the Math Isn’t Mathing

    Homeowner Strategies: To Pay Off or Not to Pay Off?

    TikTok Tips for Saving More This Holiday Season

    Upcoming NYC Meetup and Thanksgiving Wishes from the Basement Crew

    Movie Review: Conclave – Worth Your Time or Skip It?


    FULL SHOW NOTES: https://stackingbenjamins.com/best-tech-deals-2024-1608
    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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  • Ah, the holidays—a time for twinkling lights, warm cocoa, and the yearly hunt for the perfect Black Friday deal. Feeling the mix of cheer and budget-related stress? Don’t worry, we’ve got you covered! Today, Regina Conway from SlickDeals joins us to share insider tips on scoring the best bargains. From stacking deals for maximum savings to finding hidden gems (like book bargains that’ll thrill even non-readers), Regina has the scoop to help you stretch every dollar this season.
    But we’re not stopping at shopping—oh no. We’re tackling the lesser-known world of using your IRA to invest in real estate. Spoiler alert: it’s not as simple as it sounds. We’ll break down the rules, avoidable mistakes, and real estate horror stories that’ll make you think twice before jumping in.
    And because it’s the holidays, we’re sprinkling in a little fun. Think debates over Mariah Carey’s playlist dominance, nostalgic Christmas traditions, and some lighthearted banter that’s as comforting as Grandma’s stuffing (though maybe less calorie-dense). Cheers to smarter shopping and investing that doesn’t leave you out in the cold!
    Run of Show

    Thanksgiving Banter and Warm Holiday Wishes

    Saluting the Troops and Sharing Gratitude

    Black Friday Buzz: Meet Regina Conway from Slick Deals

    Spotlight on Real Estate Investor Horror Stories

    Holiday Traditions: From Playlists to Tech Talk

    Slick Deals’ Top Black Friday Shopping Tips

    Book Deals and the Unexpected Rise of Reading

    Travel Deals and Gift Cards That Pack a Punch

    Memberships, Subscriptions, and Tickets: Hidden Savings

    Utility Items and Home Improvement Must-Haves

    The Slick Deals Community: Smart Shoppers Unite

    How Slick Deals Makes Money (and Keeps the Lights On)

    Celebrating 25 Years of Slick Deals

    Historical Trivia: The Origin of Coupons

    Essential Holiday Shopping Tips for the Savvy Stacker

    Using Your IRA for Real Estate: The Dos and Don’ts

    Monthly Update on the Benefits Guide

    Holiday Season Reflections and Final Thoughts


    FULL SHOW NOTES: https://stackingbenjamins.com/black-friday-deals-2024-1607
    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 feel like life is one long, chaotic to-do list? Maybe it’s time to grab the reins and start living with intention. In today’s episode, Joe Saul-Sehy, Paula Pant, and Doc G team up with special guest Candy Valentino to help you cut through the noise, focus on what matters, and make purposeful choices that align with your goals.
    We’ll explore the power of saying “no” (because sometimes your calendar deserves a break), the magic of setting three non-negotiables, and how small, thoughtful shifts can lead to massive wins. Whether you’re a business owner plotting your empire or a 9-to-5er trying to reclaim your time, this episode offers practical tips to help you design the life you want.
    And just when you thought it was all deep thoughts and purpose, we take a detour to discuss Blackbeard’s treasure (yes, that Blackbeard) and debate its true value. Spoiler alert: The answer might surprise you—or at least make you re-evaluate your treasure-hunting strategy.
    Grab a seat, Stackers—it’s time to get intentional.
    Run of Show

    Opening Scene: Can You Fly This Plane?

    Welcome to the Stacking Benjamins Show

    Getting Intentional About Your Life

    Meet the Guests: Candy Valentino Joins the Crew

    Candy on The 9% Edge

    Why Intentional Living is Your Secret Weapon

    Trivia Time: Digging Into Blackbeard’s Treasure

    Debating the Value of Pirate Booty

    The Final Answer Revealed: Was It Worth It?

    Deep Dive: Intentionality and Finding Purpose

    Setting Intentions and Dodging Distractions

    How Small Shifts Can Spark Big Changes

    Learning to Say No Without Guilt

    Podcast Highlights and Wrap-Up


    FULL SHOW NOTES: https://stackingbenjamins.com/all-about-intentional-living-1606
    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 how to steer clear of trouble with your investments? Today, we’re diving into an SEC investigation that’s rattling one fund and discussing what you need to know to protect yourself. We’re also unpacking the benefits of passive investing and index funds—because simplifying your approach to the stock market might just be the smartest move you make.
    In our TikTok Minute, we’ll take a look at a quick clip that highlights a common financial misunderstanding, and along the way, we’ll sprinkle in a bit of British charm (no spoilers, but it’s classic).
    Finally, we’re tackling a listener question from a soon-to-be parent who’s wondering how to plan for their child’s financial future. From custodial accounts to financial aid strategies, we’ll walk through the best options to ensure your kids have a strong start. Add in Doug’s trivia, some thought-provoking discussions, and a peek at upcoming events, and you’ve got a packed episode full of actionable insights.
    Run of Show

    Introduction and Opening Remarks

    Kickoff and Today’s Topics Overview

    Discussion on the SEC Investigation and What You Need to Know

    Monitoring Your Money Effectively

    Sponsor Messages and Lighthearted Banter

    Headline: Western Assets Bond Fund in Trouble

    Debating Active vs. Passive Management

    TikTok Minute: A Quick Look at Financial Missteps

    Listener Call and Doug’s Trivia Break

    Listener Question: Financial Planning for a Newborn

    Custodial Accounts vs. Other Savings Options

    Tax Implications and Financial Aid Considerations

    Upcoming Events and Community Meetups

    Doug’s TV Show Reviews

    
    FULL SHOW NOTES: https://stackingbenjamins.com/when-good-funds-go-bad-1605
    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 feel like life keeps throwing curveballs your way? The truth is, it doesn’t actually get easier—you just get better at hitting those pitches. This week, we’re tackling financial challenges head-on with financial behavior psychologist Dr. Brad Klontz and TikTok star Adrian Brambila. Together, they deliver some much-needed “virtual slaps” to help shift your financial mindset from poor to rich.
    We’re diving into practical tips like automating your finances, avoiding debt traps, and embracing tough love to overcome obstacles. In our headline segment, we’re revealing the U.S. cities with the highest and lowest non-mortgage debt. More importantly, we’ll discuss how to manage your financial health no matter where you live. It’s all about learning to play the game the right way.
    And, of course, stick around for Doug’s trivia, humor, and possibly a questionable bread recommendation.
    Run of Show

    Monday Morning Toast Ritual

    Debate Over the Best Bread Choices

    Salute to the Troops

    Introduction to the Stacking Benjamins Show

    Meet the Monday Mentors: Brad Klontz and Adrian Brambila

    Brad and Adrian Share Harsh Truths About Wealth Building

    The Psychology of Wealth and Financial Mindset Shifts

    Automation: The Secret Hack to Building Wealth

    The Poor vs. Rich Mindset: How to Change the Way You Think

    Investing Wisely: The 4% Rule

    Book Promotions and Special Offers from the Guests

    Doug’s Trivia and Humor Break

    Coaching and Motivational Strategies to Stay on Track

    Headline Segment: Debt in American Cities (Highest and Lowest)

    Conclusion and Final Thoughts on Getting Better, Not Easier


    FULL SHOW NOTES: https://stackingbenjamins.com/tough-love-money-lessons-brad-klontz-1604
    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 many personal finance rules does it actually take to keep your financial house in order? Book after book, podcast after podcast—everyone seems to have "the" set of rules you need. But one intrepid blogger asked himself, "How much do I really need to know to keep my financial health on track?" Today, we dive into his answer: the four laws of financial health, as explored by our lively roundtable crew.
    Joining Joe and OG are Paula Pant, who's made it her mission to Afford Anything, and Jesse Cramer from The Best Interest podcast. OG’s here with a sports injury story (with a twist!), Paula’s got thoughts on ramping up savings, and Jesse dives deep into the need for a solid safety net. Get ready for laughs, valuable insights, and practical tips to help you set, track, and knock out your financial goals with confidence.
    Plus, we’re treating you to some of Doug’s legendary trivia, and revisiting Oprah’s unforgettable weight loss reveal moment. Buckle up for a mix of fun and insight straight from Mom's basement!
    Run of Show

    Introduction and Opening Remarks

    Meet the Hosts and Guests

    OG's Sports Injury Story (with a twist)

    Paula’s Early Voting Adventure

    Diving into the Four Laws of Financial Health

    Trivia Time with Doug

    Oprah’s Weight Loss Reveal: Guessing Game

    Different Theories on Oprah’s Weight Loss

    Answer Reveal and Lessons Learned

    Importance of Cash Reserves

    Building and Maintaining an Emergency Fund

    Systematic Saving and Investing Strategies

    Weekend Plans and Podcast Updates

    Closing Remarks and Takeaways

    
    FULL SHOW NOTES: https://stackingbenjamins.com/the-four-laws-of-financial-health-1603
    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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  • Curious about how AI might sneak its way into your financial plan? Today, we bring you the latest scoop on this hot topic with our guest, Robert Farrington from The College Investor. Together, we’ll break down the research on AI’s potential impact on your financial life (spoiler: it’s not here to pay your credit card bills). Plus, we tackle a listener question from someone who might've spent a bit too much time binging Better Call Saul.
    Get ready to have your assumptions challenged as we throw in a TikTok Minute that’ll shake up everything you thought you knew abouthuge companies and their projections of the future. It isn't that we don't believe Goldman Sachs...it's just that the cost of being wrong may outweigh the gains of ignoring the strategy altogether. And, of course, stick around for trivia that’ll make you the star of your next gathering—Mom says you should be prepared to impress!
    Join hosts Joe Saul-Sehy, OG, and the always-insightful Robert Farrington for an episode packed with practical financial wisdom, a few chuckles, and as always, a lot of basement charm. You know...because we're charming.
    We're coming to NYC on December 12th! Join Joe, OG, Paula Pant AND Doc G for an amazing gathering of personal finance fans. Head to https://stackingbenjamins.com/nyc to sign up before spots are gone.

    Run of Show

    Introduction and Opening Remarks

    Welcoming Robert Farrington

    Casual Banter and Health Tips

    Deep Dive into AI and Finance

    AI in Everyday Life and Financial Planning

    Challenges and Limitations of AI

    Using AI for Specific Financial Tasks

    The Future of AI in Financial Planning

    Personalized Advice and Experience

    Asking the Right Questions (to AI and yourself!)

    Where to Find More Information

    AI in Personal Finance

    Trivia Time with Doug

    Investment Strategies and Market Predictions

    Upcoming Events and Announcements - We're coming to NYC!

    Halloween Fun and Candy Tax


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  • Have you ever thought about the intersection of health and wealth? Today we start by sharing personal anecdotes about an unexpectedly painful break, leading into a robust chat with mentor Alua Arthur, a death doula who helps people find purpose through preparing for the end of life. The conversation dives deep into practical tips about setting financial goals while staying grounded, and the importance of balancing spending with saving, all while holding onto life’s deeper purposes.

    Al Pacino's financial mishaps also serve as a cautionary tale about the importance of being an active CEO of your personal finances. The episode wraps up with advice on navigating the future as veterans from OG, insights into helping children understand finances, and more. You may go look for community, but there is only one that leaves you feeling satisfied: Stacking Benjamins. 
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  • Today, we'll dive into navigating life's awkward money moments with a fantastic round table discussion. We'll cover topics like how to handle unexpected spills at a friend's house, splitting the bill during social outings, contributing to group expenses, and even first-date etiquette. Plus, we discuss how to wisely use a financial windfall, the benefits of maximizing your retirement contributions, and the potential pitfalls of paying off your mortgage early. Get ready for practical advice, insightful stories, and plenty of laughs as we tackle these everyday financial dilemmas.

    Introduction and Joe's Favorite Things

    Upcoming Episodes and Special Guests

    Guide to Workplace Benefits

    Sponsors and Show Kickoff

    Round Table Discussion: Awkward Money Situations

    Handling the Check: Etiquette and Stories

    Birthday Dinners and Social Norms

    First Dates and Financial Expectations

    Road Trips and Gas Money

    Guessing the 1933 Minimum Wage

    Trivia Results and Reactions

    Listener Question: What to Do with Extra Money?

    Panel's Personal Updates and Announcements

    Post-Show Banter and Fun


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  • You asked for details on Joe's son's real estate adventure, and today you get it! This episode takes you to CampFI Midwest, where Joe's 29-year-old son, Nick, shares his journey toward financial independence through real estate investment. Starting in 2020, Nick began buying and renovating properties, primarily in Detroit, while living in Seattle and working at Microsoft. Learn about his strategies, the challenges he faces, and the importance of diversification in building a solid financial plan. The episode includes insights on finding deals, managing properties remotely, and the significance of making and learning from mistakes in the path to financial independence.


    Introduction to Greatest Hits Week

    Introducing Camp FI and Nick's Journey

    Nick's Real Estate Empire

    The Stacking Benjamins Podcast Vibe

    Nick's Detroit Real Estate Adventures

    Nick's Real Estate Strategy and Challenges

    The Importance of Diversification

    Concluding Thoughts and Advice


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  • Today, we look at the other side of financial independence: being able to travel the world! Our new Stacking Adventures show is off the ground, and we're giving you a peek at the latest episode. This show highlights YOUR experiences traveling, and when it comes to Japan, you share the best, worst, and in-between. From puking in your bosses' wife's shoes to riding the bullet train, we hear stories from Adventurers and share our own comments. You'll hear tips on packing, organizing luggage storage, theme parks to attend, places to find good food, navigating transportation, and more.
    You'll find more episodes wherever you're listening to Stacking Benjamins, OR you'll find blog posts, trip reports, packing lists, and more at StackingAdventures.com.
    Do you have travel stories about Peru, Chile, ghost tours, or New Orleans? Share those stories at StackingAdventures.com/MyStory
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  • Today, we'll discuss the pitfalls of overly conservative retirement planning and how it could delay your financial independence and retirement dreams. In this show which was originally aired on our "brother" show Earn & Invest, Doc G, and guest Jesse Cramer from the Best Interest podcast delve into the importance of finding a balance, exploring the impacts of stacking conservative assumptions related to social security, investment returns, and inflation. Jesse shares practical tips on re-evaluating your retirement assumptions, emphasizing the significance of flexibility and ongoing adjustments to avoid unnecessarily prolonging your work life.

    RUN OF SHOW

    Introduction and Topic Overview

    The Cost of Being Too Conservative

    Interview with Jordan Grumet and Jesse Kramer

    Workplace Benefits Guide Announcement

    Earn and Invest Podcast Begins

    Jesse Kramer's Background and Career Shift

    Conservative Assumptions in Retirement Planning

    Introduction to Conservative Retirement Assumptions

    Guest Introduction: Jesse Cramer

    The Impact of Conservative Assumptions on Retirement

    Strategies to Avoid Overly Conservative Assumptions

    Revisiting and Adjusting Retirement Plans

    The 4% Rule and Its Implications

    Balancing Conservatism and Aggressiveness in Retirement Planning

    The Consequences of Overly Conservative Planning

    Practical Tips for Retirement Planning

    Exploring the 'Die With Zero' Philosophy

    Dealing with Loss Aversion Anxiety

    Conclusion and Final Thoughts

    Post-Interview Discussion


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  • To kick off a contentious week for the USA, we share one of our FAVORITE stories about the thread that binds us, our goals, our dreams, and yes, even our money. Laura Schroff was a high-powered executive in Manhattan when her life was changed forever by an 11-year old boy. It's a story you won't soon forget. Plus, we're thrilled that Scott Trench, BiggerPockets CEO joins us as guest co-host. We talk about crypto, athletes, and their money. It's our favorite way to discuss how your own money decisions could be better made. We also dive into non-compete contracts. That world has been changing quickly, and we've got you covered.
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  • Have you ever felt overwhelmed by your finances? Do you find yourself either making purchases as "retail therapy" or avoiding looking at your statements and online accounts? Or maybe, on the other end of the spectrum, you find yourself hoarding cash because you don't know when the next "rainy day" is going to arrive? In all of these cases and more, you might be experiencing financial trauma, a topic that is the focus of today's Stacking Benjamins live round table at FinCon 2024 in Atlanta, Georgia. Hosted by Joe Saul-Sehy and featuring licensed family and marriage therapist Wendy Wright, certified financial planner Lawrence Sprung, and Afford Anything's Paula Pant, the discussion dives into the deep-seated emotional aspects of money. You'll learn about the signs of financial trauma, such as neglecting finances, overspending, and hoarding, and how these behaviors can impact your life. The panel offers insights into addressing and overcoming these issues, emphasizing the importance of compassionate curiosity and seeking professional help when needed. Whether you're living paycheck to paycheck or have a significant net worth, this episode will guide you on the path to better financial health and well-being.
    RUN OF SHOW

    Opening Banter and Introduction

    Live from FinCon 2024

    Meet the Panelists

    Diving into Financial Trauma

    Signs of Financial Trauma

    Scarcity Mindset and Personal Stories

    Cultural and Individual Financial Trauma

    Judgment and Financial Secrecy

    Inherited Wealth and Emotional Struggles

    Behavioral Finance in Financial Planning

    Building Compassionate Financial Relationships

    Recognizing Financial Trauma: Hoarding

    Societal Views on Hoarding vs. Saving

    Personal Stories of Financial Extremes

    Balancing Financial Planning and Living in the Present

    Diagnosing Money Hoarding and Anxiety

    Steps to Address Financial Anxiety

    Exploring False Connections with Money

    The Importance of Financial Planning and Adjustments

    Tracking Spending and Financial Awareness

    Principles of Financial Therapy

    When to Seek Financial Therapy

    Conclusion and Resources

    FULL SHOW NOTES: https://stackingbenjamins.com/overcoming-financial-trauma-1595
    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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  • Today, we're joined by funeral director Scott Mueller, who shares invaluable advice on pre-planning your final expenses. Scott elucidates on the importance of making arrangements ahead of time and the benefits it brings to both you and your loved ones during emotionally charged times. Avoid common pitfalls and choose wisely to avoid turning your financial planning into a horror show. Trick or treat? More like protect your assets or weep!
    In our headline segment, we delve into optimizing your homeowner's insurance with critical features like replacement cost coverage, special personal property endorsements, and umbrella policies. Discover how these essential elements can guard your castle and your treasures from life's unexpected frights. Finally, we lighten the mood with Doug's hilarious trivia and some fun Halloween anecdotes, ensuring you end this episode both smarter and happily haunted.

    RUN OF SHOW

    Introduction to the Witching Hour

    Halloween Special: Stacking Benjamin Show

    Meet the Funeral Director: Scott Mueller

    The Importance of Pre-Planning Funeral Expenses

    Personal Stories and the Emotional Impact

    Trust Issues with Funeral Directors

    Avoiding Funeral Scams and Making Informed Decisions

    Pre-Planning: Burial, Cremation, and Other Options

    Final Thoughts and Resources

    Iconic Horror Movie Lines

    Halloween Trivia and Chat GPT

    Funeral Planning Stories

    Umbrella Liability Insurance

    Halloween's BEST Jokes and Wrap-Up


    FULL SHOW NOTES: https://stackingbenjamins.com/final-expenses-planning-with-scott-mueller-1594
    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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  • Today, we'll dive into an exciting financial education idea brought to us by award-winning columnist and host of The Money Life Show, Chuck Jaffe. Do you think Halloween's kinda boring for kids and just a sugar rush? Not at Chuck's house! Discover Chuck's innovative 'cash or candy' concept, transforming Halloween into a fun and educational game that teaches kids about probability, risk management, and decision-making. This unique approach blends Halloween fun with critical financial lessons, making it a memorable learning experience for children and parents.
    In our headline segment, we explore some chilling retirement regrets shared in a compelling Business Insider article, highlighting common pitfalls and how to avoid them. We also discuss key strategies for better retirement planning, such as potentially delaying social security and being prepared for unforeseen emergencies. If you're worried about not having enough for financial independence, this may be the segment for you.
    Lastly, we wrap up the episode with Doug's intriguing Halloween-themed trivia and a lively discussion about the NFL's global expansion efforts, including a look at watching football games in Germany. Join us for a fun and educational journey into the world of Halloween-fueled financial literacy!
    RUN OF SHOW

    Halloween Costumes and Banter

    Salute to the Troops and Halloween Plans

    Halloween Week Episode Introduction

    Halloween and Money Lessons with Chuck Jaffe

    Halloween Games and Economic Lessons

    Chuck Jaffe's Halloween Tradition

    Money Life Show and Financial Insights

    Disturbing Ways to Make Money

    Trivia Question: a Murderer's Profession

    Pineapple Drinks

    Headline: Retirement Regrets

    Discussion on Retirement Savings

    Client's Early Retirement Story

    Janice's Regrets and Future Plans

    Automating Savings and Easy Listening

    Community Engagement and Reviews

    NFL's International Games

    Fun with German NFL Commentary

    Christmas Movie Horror Parody


    FULL SHOW NOTES: https://stackingbenjamins.com/halloween-money-lessons-with-chuck-jaffe-1593
    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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  • Are you on the same page with your significant other? Financially speaking, of course! Given that money is the leading cause of divorce in the US, it's a topic worth working on together. And money talks in relationships don't just apply to romantic relationships - it can extend to include parent/child, etc. relationships. We're talking money and relationships on today's roundtable. Pull up a chair with Paula Pant from Afford Anything, OG, and special guest Doug Cunnington from the Mile High FI Podcast. This is an episode you don't want to miss!
    In the second half of the show, we dive into the sensitive topic of what to do when you and your spouse can't agree. You won't want to miss this!
    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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  • Today we share a fresh perspective on personal and financial risk, featuring the always insightful Len Penzo (LenPenzo.com). Joe, OG and Len will dive into the complexities of managing your 401k and understanding the risk tolerance required to meet your goals. We'll share pivotal strategies for effective retirement planning and hopefully help you grasp why taking enough risk is crucial, especially for younger investors who have time to recover from potential losses. Listen in as we explore investment behaviors versus portfolio performance and how emotional decisions during market fluctuations can impact your financial journey.
    We don’t just tackle numbers here. We'll also examine whether widening your approach to include career risks and the often-overlooked social risks that can open doors to new opportunities is a good strategy. We'll talk about on growing your employment opportunities, ensuring long-term wealth, and balancing financial and emotional satisfaction. Plus, there just may be a slight amount of banter about Halloween treats, the joys of IRS conundrums, and the misconceptions of viral TikTok financial advice.

    To top it all off, we may or may not share stories about Joe’s adventures learning craps in Las Vegas, revealing the thrills and lessons of gambling. If you're searching for lessons, it may include the importance of knowing when to walk away, and the camaraderie forged at the casino tables. Whether you’re tuning in for practical financial strategies or just to enjoy some relatable stories and laughs, this episode is packed with takeaways on looking at risk differently in every facet of your life.


    Introduction to Debt Management

    Welcome to the Stacking Benjamin Show

    Discussing Risk with Len Penzo

    The Fortune Cookie Incident

    Understanding Risk Tolerance

    Career and Social Risks

    Halloween Treats and Risks

    Stocking Up for Halloween

    Diving into Risk Management

    TikTok Minute: Career Success

    Doug's Trivia: Understanding 1031 Exchange

    Listener Question: Employer-Sponsored IRA Plans

    Vegas Stories and Gambling Tips


    FULL SHOW NOTES: https://stackingbenjamins.com/len-penzo-halloween-1591
    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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  • Grab your coffee mug and join us for a journey full of strategic insights and valuable life lessons. Business legend Seth Godin joins us to share his wisdom on financial strategy and personal success. From college applications to wedding planning, Seth's advice on using a strategic compass over an outdated map will help you navigate big decisions and avoid wasting time and potential. Plus, we explore the balance between effortless yet intricate service and strategic pricing, advocating for value over cutting costs like Walmart because, sometimes, the tension in the experience is what makes it memorable and rewarding. There are plenty more actionable takeaways in our discussion with one of the most prominent gurus in marketing. Mainly, we delve into why having a well-thought-out strategy for life and personal finance can make all the difference. Learn from Seth's rich experience—from guiding startups to success to creating impactful strategies.
    We also explore the historical strategies that have shaped businesses like Yahoo and Google. Seth emphasizes the importance of vocalizing strategies, balancing personal agency with systemic constraints, and the essential threads of strategy: time, empathy, games, and systems. Using personal finance as a lens, Seth helps you understand complex concepts in a relatable way, underscoring how strategic thinking can transform everything from wedding expenses to retirement planning.
    Of course, that's not all. In our headline segment, we share the results of a recent study by Harvard, Vanguard, and others on 401k plan "leakage." New rules allow people to take annual withdrawals from their retirement plans. Will people abuse this new rule? The results of this study are surprising, to say the least. We discuss how to use 401k loans, why we don't favor them, and strategies to plug leaks so that your financial boat doesn't sink.
    On top of that, we also share trivia from Doug and much, much more! This may be your favorite Monday on Stacking Benjamins!

    Run of Show

    Morning Optimism and Weekend Plans

    Saluting Our Troops

    Special Guest: Seth Godin on Strategy

    The Importance of Strategy in Personal Finance

    College Applications and Life Strategies

    Seth Godin's Background and Achievements

    Understanding Strategy: Time, Empathy, Games, and Systems

    Walmart's Competitive Edge

    Freelancing on Upwork: A Race to the Bottom

    Justifying Higher Prices

    The Power of Peer Groups

    Mentorship vs. Peer Groups

    Personal Experiences with Peer Groups

    Trivia Time with Doug

    401k Loans and Retirement Plan Leakage

    The Importance of Cash Reserves

    Upcoming Events and Meetups

    Consulting Firm Anecdote

    FULL SHOW NOTES: https://stackingbenjamins.com/create-you-life-strategy-with-seth-godin-1590
    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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  • Have you ever met someone whose retirement was wrecked by poor tax planning? While tax planning is essential, one big-named figure in the financial community who's a tax expert says that tax planning may be over-emphasized. But is it? Today, we're joined by experts Deb Meyer (Beyond Budgets podcast), Sean Mullaney (FI Tax Guy YouTube Channel), and the guy behind the Earn & Invest podcast, Doc G. Our financial experts will debunk common tax myths and provide actionable insights for a secure financial future. They'll explore the essential differences between marginal and effective tax rates, and you'll learn how effective tax planning can positively impact your retirement. Discover how to leverage tax calculators to avoid dreaded tax surprises and understand the nuances between Roth and traditional retirement accounts. Our enthusiastic experts bring humor and real-life examples into the mix, making complex tax strategies accessible to everyone, whether you're an entrepreneur or planning for retirement. In the second half of our discussion, we shift focus to practical financial advice. Discussions revolve around the temptation to overly optimize tax shelters and the importance of balancing tax efficiency and accessible funds. We cover concerns about the 'tax torpedo' affecting Social Security taxes and highlight the nuanced approaches required for better tax planning in an investor's journey. The insights shared aim to demystify tax planning for listeners, helping them shape sound financial strategies tailored to their personal circumstances.
    At the midway point, we'll pause for Doug's trivia question, today focused on a BIG tax case: Al Capone's run-in with the IRS. We'll share stories about his untaxed empire and discuss Walt Disney's clever tax maneuvers. We think you'll laugh through valuable tips on diversifying tax statuses and recovering tax bases. Hopefully, you'll leave with a better grasp of maximizing your tax efficiency and preparing for a financially stable future.


    Ignition Sequence and Lift-Off

    Introduction to the Stacking Benjamin Show

    Meet the Hosts and Guests

    Tax Talk and Trivia Teasers

    Welcoming the Financial Experts

    Diving into Tax Planning

    Effective vs Marginal Tax Rates

    Tax Planning for Entrepreneurs

    The Importance of Tax Diversification

    Trivia Challenge Begins

    Al Capone's 1931 Income Mystery

    Guessing Al Capone's Untaxed Income

    Revealing the Real Answer

    Financial Nerds and Tax Concerns

    The HSA Debate

    Annuities and Tax Gotchas

    Cash Value Life Insurance

    Podcast Highlights and Farewells

    S-Corp vs Sole Proprietor


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