The Stacking Benjamins Show

Swipe right on financial stability or get ghosted by your savings? While Joe's mom yells upstairs about who left the empty milk carton in the fridge (seriously, who does that?), we’re diving into the messy, complicated, and sometimes hilarious world of your relationship with money. Are you in a stable, long-term commitment with your finances, or are you stuck in a toxic on-again, off-again affair with impulse spending?

Special guest Shannah Game, certified financial planner and author of Unraveling Your Relationship with Money, joins us to decode the emotional baggage we bring to our bank accounts. Meanwhile, Doug swears he’s figured out how to “game” the stock market using AI—spoiler alert: it involves a Magic 8-Ball. We also tackle some questionable dating preferences (because who doesn’t want to know if their financial habits make them swipeable?) and unpack the latest market shake-ups.

In this episode:

Will your money habits lead to a lifetime of wealth—or will your wallet break up with you via text? Tune in and find out!

FULL SHOW NOTES: https://www.stackingbenjamins.com/relationship-with-money-financial-habits-sb1642

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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Is automating your finances the key to effortless money management, or a one-way ticket to financial autopilot disaster? Paula Pant, Jesse Cramer, and Doc G join us to navigate the fine line between automation genius and accidental money mayhem.

Done right, automation saves you time and stress. Done wrong? You might be funding a forgotten gym membership for the next five years. 😬

💰 The Power of Automation – How strategic automation can make your financial life simpler, more efficient, and stress-free.

🤖 What to Automate & What to Keep Manual – Should you set bills to auto-pay, or will that lead to mysterious charges on your credit card?

📊 High-Tech Money Tools: Are They Worth It? – Todoist, Notion, and other techy automation tricks—are they game-changers or just digital clutter?

💡 Personal Automation Hacks – How the panel automates their finances like pros (without losing control of their money).

🎭 The Dark Side of Automation – Horror stories of overdraft surprises, vanishing paychecks, and auto-pay regret.

📢 Stacker Debate: Should You Automate Everything? – The great automation showdown—when automation helps and when it hurts.

✨ Special Bonus: The Worst Things to Automate – Some things should NEVER be on autopilot. Find out what financial automation fails made our list.

✅ Automation = Freedom (When Used Wisely). The right balance saves you time while keeping you in control.

✅ Auto-pay is great—until it isn’t. Track subscriptions and bills so you don’t end up paying for things you don’t use.

✅ Manual check-ins keep you financially sharp. Even with automation, you need to review your money regularly.

✅ Tech tools can help—but they’re not magic. The best system is the one you actually use.

🎧 Hit play now and rethink your approach to automation before it outsmarts you!

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What do scammers, fancy doors, and Twinkies have in common? Turns out, more than you think! Today, Joe, OG, and Doug take you on a wild ride through financial scams, fraud prevention, tax implications of dual residency, and... the surprising link between door quality and financial stability. (Yeah, we didn’t see that one coming either.)

🕵️‍♂️ Scams, Scams Everywhere! – From identity fraud to the trendy new "deed theft" scam, learn how to protect yourself before a scammer claims your house faster than you can say "that wasn't in the budget."

💳 Fraud-Proofing Your Finances – Why setting up credit monitoring, checking your bills, and paying attention to sketchy emails can save you thousands in headaches.

🚪 The TikTok Minute: What Do Soft Close Doors Say About Your Wealth? – Is your financial future written in the way your doors shut? Find out why door noises might reveal more about your bank balance than your credit score.

🧾 State Taxes & Dual Residency: The Sneaky Costs of Living in Two Places – Thinking about snowbirding to Florida or keeping a backup home in another state? We break down what you NEED to know before state tax authorities come knocking.

🤖 Password Security & The Quantum Computing Takeover – Is the future of passwords doomed? What you should be doing now to keep your Twinkies—and your bank accounts—safe.

🍕 Pizza Cutting Controversy & Nostalgic Minivan Stories – Because what’s a Stacking Adventures episode without a little debate, a little reminiscing, and a whole lot of questionable opinions on pizza slicing?

🍰 Twinkies Trivia: A Deep-Dive into the Snack That Never Dies – Have scientists unlocked the secret of Twinkie immortality? More importantly, should Twinkies be considered part of a solid financial plan? (Spoiler: probably not, but let’s discuss.)

📢 Stacker Questions & Community Fun – Helping a listener navigate dual residency tax headaches + a special meetup announcement!

✅ If it sounds too good to be true, it’s a scam. Seriously. Trust your gut, not the email from "Prince Jeff of Nigeria."

✅ Your finances need monitoring, just like your snack stash. Set up credit alerts and check your accounts weekly to avoid surprises.

✅ Moving states for tax savings? Do the math first. Dual residency isn’t always the loophole people think it is.

✅ Twinkies may last forever, but financial security requires maintenance. A solid money plan beats a stockpile of snacks (but only slightly).

🎧 Hit play now for a mix of financial wisdom, scam-prevention tips, and just the right amount of Twinkie-fueled fun!

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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Retirement planning isn’t about waiting until 65—it’s about setting yourself up for a life you love starting right now! Today, Certified Financial Planner Benjamin Brant joins us to challenge traditional retirement thinking.

✅ Retirement planning starts now, not later – Why waiting to plan is the biggest mistake you can make.

✅ Dream big, but expect some ‘bad data’ – How testing financial plans (and life plans!) helps you refine your future.

✅ Why trust beats performance in financial planning – A new study shows that your advisor’s returns matter less than their integrity.

✅ The Monte Carlo simulation debate – What this financial tool actually tells you (and what it doesn’t).

✅ Childhood dreams, stand-up comedy, and time travel? – How revisiting past joys can shape a meaningful retirement.

✅ Choosing the right financial advisor – The #1 factor to look for before handing over your portfolio.

💡 Retirement isn’t a number—it’s a mindset. The earlier you start thinking about what brings you joy, the better.

💡 Financial planning isn’t perfect science. Bad data, trial-and-error, and adjusting your plan over time? Totally normal.

💡 Trust is your biggest investment. A good financial advisor isn’t just about returns—they’re about guidance you can rely on.

Grab your favorite drink (coffee, bourbon—you choose!) and let’s stack some wisdom for your future self.

🎧 Hit play now and start building your best retirement today!

FULL SHOW NOTES: https://stackingbenjamins.com/find-your-fulfillment-in-retirement-Benjamin-Brandt-1639

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 dreamt of quitting your job early and sipping piña coladas on a beach? Before you tell your boss what to do with that job and start booking your one-way ticket to paradise, today’s roundtable might make you think twice. Join Jesse Cramer from The Best Interest, Paula Pant from Afford Anything, and our own OG as they break down the case against early retirement. The gang’s here to challenge the “quit work, retire early” dream and explore whether it’s really as awesome as it sounds—or if there are a few catches you haven’t considered.

The conversation gets into the nitty-gritty of why early retirement might not be the smooth ride some people think it is. From the psychological toll of too much free time to the unexpected financial hurdles, our panelists share the real stories behind the headlines. What’s the balance between financial freedom and a fulfilling life? Can you really retire early without regret, or does the cost of quitting work too soon outweigh the benefits?

And don’t forget about Doug’s wicked trivia challenge!

FULL SHOW NOTES: https://stackingbenjamins.com/the-case-against-early-retirement-1638

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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See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ever wondered if you’re better off building your own target date fund instead of relying on a one-size-fits-all option? We’re diving into whether crafting your own investment mix is worth the effort, potentially saving you fees and giving you more control over your portfolio.

But even the pros get it wrong sometimes—just ask Vanguard. We’re covering the major settlement they’re facing over misleading statements about taxes and target date funds, proving that even the big guys make costly mistakes.

Meanwhile, a listener asks a great question about balancing tax optimization with financial flexibility—because what good is a perfectly tax-efficient plan if it ties your hands when you need cash? Plus, Doug takes us back to the origins of the gasoline-driven automobile, and there’s even an unexpected run-in with a Supreme Court justice (because why not?).

And of course, we’ve got a TikTok moment that’ll have you questioning life choices and a few financial misconceptions that might just make you rethink your approach to money.

Resources Mentioned in This Episode:

Tune in now and get the insights you need to build a smarter investment strategy—without falling into costly traps.

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What’s really standing between you and your financial goals? In today’s mentor, Jessica Moorhouse—financial counselor, podcast host, and author of Everything But Money—joins Joe to dive into the mental and emotional side of managing money. Jessica shares her journey with therapy, how relationships shape our financial habits, and the role of self-talk in creating a healthier money mindset. Whether you’re feeling stuck or just want a fresh perspective, this interview offers practical tools to help you take control of your financial future.

In our headline segment, we explore the concept of a “no-buy” list—a clever strategy one woman used to pay off $34,000 in debt. Learn how gamifying financial goals can make saving more manageable—and even fun! Whether it’s cutting back on unnecessary spending or finding creative ways to save, this segment will inspire you to rethink how you approach your financial challenges.

Here’s what we cover today:

FULL SHOW NOTES: https://stackingbenjamins.com/changing-your-money-self-talk-jessica-moorhouse-1636

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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Introducing Finding the Best Flight Deals to Anywhere in the World with Scott Keyes from All the Hacks with Chris Hutchins.

Follow the show: All the Hacks with Chris Hutchins

#5: Chris and Scott cover how to get the best deals on flights around the world. They discuss when and how to find and book the cheapest flights, making the most of flight cancelations or delays and lots of travel hacks to maximize happiness on all your trips.

Scott Keyes (@smkeyes) is the founder of Going, a service that helps over two million members find incredible deals on flights around the world. He is also the author of the bestselling book Take More Vacations: How to Search Better, Book Cheaper, and Travel the World.

Full show notes available at: https://allthehacks.com/cheap-flights-scott-keyes/

Partner Deals

For all the deals, discounts and promo codes from our partners, go to: allthehacks.com/deals

Resources Mentioned

Connect with Scott Keyes: Twitter | Instagram

Scott's Book: Take More Vacations

Sign up for Scott's Flight Deals: Going

Best Search Engine for Flights: Google Flights

Find Nonstop Flights from any Airport: Flight Connections

Find Train, Bus and Ferry Routes: Rome2Rio | Seat61

Full Show Notes

(00:46) Scott’s Background and How He Got the Best Flight Deal in His Life

(03:50) The Power of More Vacations: Boosting Happiness and Success

(5:45) Living in the Golden Age of Cheap Flights: Why It's Possible

(7:09) Flexibility: The Key Areas for Scoring Cheap Flights

(9:47) Flight Deal Insight: Small vs. Large Airports

(13:39) Where to Look for Your Ideal Cheap Flights

(19:04) The Cost of Budget Airlines: Is It Worth It?

(22:05) Flight Delays and Cancellations: Navigating Challenges

(27:28) When Do You Want to Book Your Flights

(31:11) The Greek Island Strategy: Saving Big on International Trips

(34:51) Two Search Tools: Finding Nonstop Flights and Ferries, Trains and Buses

(37:48) Scott's Approach to Travel Insurance

(39:03) Change and Cancellation Policies: What You Should Know

(52:38) Leveraging Flight Schedule Changes for Advantage

(42:44) Business Class: Worth the Splurge?

(45:17) Optimal Timing for Activities to Maximize Happiness

(47:14) 24-Hour Rule: Sealing the Deal on Cheap Flights

(49:56) Group Travel Savings: Strategies for Multiple Passengers

Connect with All the Hacks

All the Hacks: Newsletter | Website | Membership | Email

Chris Hutchins: Twitter | Instagram | Website | LinkedIn

Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

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DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to [email protected].

Do financial boogeymen haunt your dreams? You’re not alone. Today, we’re diving into the worries that keep even the most seasoned finance nerds up at night. From concerns about index fund concentration to the fear of market manipulation and obsession with asset allocation, this episode tackles it all with insight and a healthy dose of perspective.

Joining Joe and OG in the basement is an all-star panel: Paula Pant from Afford Anything, Jesse Cramer from Best Interest, and Dr. Jordan Grumet from Earn and Invest. Together, they’ll share strategies to conquer financial fears by staying calm, focusing on the big picture, and sticking to sound investment principles.

And don’t miss the kickoff of the year-long Stacking Benjamins Trivia Challenge! It’s packed with brain-busting questions, lively debates, and, yes, the occasional cat butt reference (because it’s still the basement, after all).

Resources Mentioned in the Episode:

FULL SHOW NOTES: https://stackingbenjamins.com/financial-worries-and-what-to-do-about-it-1635

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

Enjoy!

Tune in now and learn how to leave your financial fears in the dust while keeping your money goals on track.

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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Introducing 11 Habits To Transform Your Life In 2025 from The School of Greatness.

Follow the show: The School of Greatness

Join me for a powerful solo episode where I dive deep into the 11 fundamental habits that have transformed my life and can revolutionize yours too. From creating a clear vision to mastering the art of breathing, I share personal stories and scientific insights about how these practices have shaped my journey to happiness. If you're tired of waiting for happiness to find you and ready to create it intentionally, this episode provides actionable strategies backed by research and real-world experience. I break down each habit with practical examples and implementation tips that you can start using today.

In this episode you will learn:

• How creating a clear vision eliminates aimlessness and provides direction for sustainable happiness
• Why maintaining a positive attitude during adversity is crucial for personal growth and success
• The scientifically-proven connection between serving others and reduced stress levels
• How practicing daily gratitude can rewire your brain for increased happiness and abundance
• The importance of setting healthy boundaries for both relationships and personal routines

For more information go to https://www.lewishowes.com/1709

For more Greatness text PODCAST to +1 (614) 350-3960

More SOG episodes we think you’ll love:

Dr. Caroline Leaf – greatness.lnk.to/1481SC

Dr. Andrew Huberman  – greatness.lnk.to/1455SC

Nedra Tawwab – greatness.lnk.to/1085SC

Get more from Lewis! 

Pre-order my new book Make Money Easy

Get The Greatness Mindset audiobook on Spotify

Text Lewis AI

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DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to [email protected].