The Stacking Benjamins Show

Latest Episodes:

How To Use Our #1 Key To Money Management Success (SB1641) Feb 07, 2025

Show notes

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. 😬

What’s Inside This Episode?

💰 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.

Takeaways for Smart Stackers:

✅ 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!

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.

Yet Another Insurance To Avoid (SB1640) Feb 05, 2025

Show notes

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.)

What’s Inside This Episode?

🕵️‍♂️ 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!

Takeaways for Smart Stackers:

✅ 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!

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.

Redefining Retirement with Benjamin Brandt (SB1639) Feb 03, 2025

Show notes

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.

What We Cover:

✅ 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.

Key Takeaways:

💡 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!

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.

The Case Against Early Retirement (SB1638) Jan 31, 2025

Show notes

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!

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.

Unpacking a Rare Vanguard Target Date Fund Problem (SB1637) Jan 29, 2025

Show notes

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.

What’s Inside Today’s Episode:

Vanguard’s Costly Mistake: The settlement every investor should know about.
Understanding Mutual Fund Taxes: How taxes sneak up on your investments.
DIY Target Date Funds: Pros, cons, and when to consider building your own.
Trivia Time with Doug: The surprising story behind the gasoline-driven car.
The TikTok Minute: Financial advice that may (or may not) be worth your time.
Financial Flexibility vs. Tax Optimization: Finding the balance in your strategy.
Community Announcements & Meetups: Where to find us next.

Episode Highlights:

Vanguard’s Legal Trouble: What happened, and what it means for investors.
Mutual Fund Taxation: Avoiding unexpected tax bills.
Should You Build Your Own Target Date Fund? We break down the numbers.
Listener Q&A: How to stay tax-efficient while keeping access to your cash.
Doug’s Trivia: Who REALLY built the first gasoline-powered car?
An Unexpected Supreme Court Encounter: Because that’s just how things go around here.

Resources Mentioned in This Episode:

Learn more about Vanguard’s target date fund settlement in our show notes: https://www.stackingbenjamins.com/vanguard-target-retirement-trouble-1637
Read up on mutual fund tax strategies and more by signing up for our 201 newsletter! https://stackingbenjamins.com/201

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

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.

Is Your Brain Blocking Your Financial Goals? (with Jessica Moorhouse) SB1636 Jan 27, 2025

Show notes

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:

Saluting our troops—and wondering why Doug still doesn’t have a Navy Federal mug
Meet Jessica Moorhouse: Financial counselor, podcast host, and author of Everything But Money
Unlocking the connection between your money mindset and financial success with Jessica
How Jessica’s personal journey and therapy shaped her healthier money mindset
Unpacking how emotions and relationships impact financial habits
Understanding rational vs. irrational guilt—and how it affects your money decisions
Recognizing irrational guilt and why it’s critical to tackle it
Celebrating financial wins and overcoming the fear that holds you back
Jessica’s book Everything But Money—and why it’s a must-read for anyone improving their financial mindset
Sneak peek: What’s next on the More Money Podcast with Jessica Moorhouse
Doug’s historical trivia: Financial lessons from the past
Gamifying financial goals: Make saving and investing fun and rewarding
Real-life success stories: The No Buy Challenge and how it helped pay off $34,000 in debt
Join our community: Upcoming meetups and ways to get involved
Final thoughts and takeaways: Simple actions you can start today to improve your financial mindset

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!

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.

These Are Our Community's Biggest Money Monsters (SB1635) Jan 24, 2025

Show notes

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).

What’s Inside Today’s Episode:

Meet the Contributors: Paula, Jesse, and Dr. Grumet join the crew.
Index Fund Concentration: Are index funds too risky? The panel weighs in.
Addressing Financial Fears: From market scams to fraud and manipulation, here’s how to keep your cool.
Trivia Challenge Kickoff: A brand-new Stacking Benjamins tradition begins.
Market Efficiency and Insider Trading: Can you really beat the market?
Asset Allocation Obsession: Why overthinking your portfolio can be your worst enemy.
Upcoming Episodes: What’s next on the Stacking Benjamins calendar?

Highlights from the Episode:

Index Fund Concentration: The crew discusses whether having too much of the market in a few big players is a recipe for disaster.
Financial Fears: Practical advice for keeping anxiety at bay when market volatility hits.
Market Scams and Frauds: How to spot them and protect yourself.
Trivia Time: A heated debate over billionaire counts, complete with unforgettable banter.
Asset Allocation: Tips for avoiding paralysis by analysis and focusing on long-term strategies.

Resources Mentioned in the Episode:

Learn more from Paula Pant at Afford Anything.
Explore Jesse Cramer’s insights at Best Interest.
Dive into Dr. Jordan Grumet’s conversations at Earn and Invest.

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.

Can You Find More Cheddar By Navigating Volatile Markets? (SB1634) Jan 22, 2025

Show notes

Feeling like the stock market is a high-stakes game of pinball lately? Not sure how to steady your hand when it comes to retirement accounts? In this episode, we tackle the rollercoaster of market volatility with actionable strategies to keep your retirement plans on track. Learn how to create an Investment Policy Statement, whether a Roth IRA still deserves a spot in your portfolio, and smart ways to withdraw from retirement funds without triggering costly mistakes. Plus, discover why trying to time the market is like predicting the weather with a Magic 8-Ball.

Doug shares a tale involving a Chinese couple and some financial advice that’s worth sticking around for. Whether you’re building financial independence or refining your retirement strategy, this episode has you covered.

What We Cover Today:

Market Rollercoaster Madness: Stock, Bitcoin, and why patience pays off.
Creating an Investment Policy Statement: Stay calm and strategy on.
Listener Q&A: Chris from Georgia asks about retirement withdrawals.
Roth IRA Reboot: Is it still a go-to for your portfolio?
Financial Headlines: Why tuning out the noise can save your sanity.
Trivia Time with Doug: A historical nugget tied to financial wisdom.

Highlights from the Episode:

Market Volatility Analysis: Stocks and Bitcoin – what’s up, what’s down, and what you should do about it.
Listener Question: Tapping retirement accounts – the dos, don’ts, and what-ifs.
Investment Philosophy: Why having a policy statement is the ultimate stress reliever.
TikTok Minute: A social media take that’ll have you rethinking the advice you see online.
New Year’s Resolutions: Money nicknames, quirky goals, and strategies for staying on track.
Closing Remarks: Key takeaways to help guide your financial decisions.

Resources Mentioned in This Episode:

Sign up for our Free Weekly Newsletter for insights, tips, and resources: https://stackingbenjamins.com/201
Join us at our Upcoming Meetups to connect and learn more: https://stackingbenjamins.com/meetup.

FULL SHOW NOTES: https://stackingbenjamins.com/stock-market-volatility-beginning-of-2025-1634

Tune in now and take the first step toward turning market madness into financial confidence.

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.

Navigating Debt, Crypto Scams, and Social Media's Wild West (with Natalia Brown) SB1633 SB Jan 20, 2025

Show notes

Feeling overwhelmed by debt or unsure how to navigate the fast-paced world of financial advice online? We’ve got you covered! This episode features Debt Relief Advocate Natalia Brown from National Debt Relief, who shares practical tips to climb out of financial trouble and steer clear of predatory practices.

But that’s not all—we dive into the Wild West of TikTok crypto advice, where nearly 70% of content is misleading enough to derail your financial plans. Joe and OG break it all down with their trademark insight, helping you sort fact from fiction in the world of digital finance.

Here’s what you’ll learn:

Tackling Debt: Natalia Brown’s strategies for overcoming financial stress and avoiding common traps.
Crypto Caution: Why TikTok might not be the best place for your financial advice (and what to watch out for).
Credit vs. Stability: The difference between obsessing over credit scores and focusing on long-term financial health.
Digital Disclaimers: How transparency (or lack thereof) online can impact your wallet.

And of course, no episode is complete without Doug’s trivia to keep things lively and unpredictable. Whether you’re tackling debt, dabbling in crypto, or just trying to stay informed, this episode will leave you with actionable advice and a fresh perspective on navigating today’s financial challenges.

Tune in and take the first step toward a more confident financial future!

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-eliminate-debt-once-and-for-all-natalia-brown-1633

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

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

Our Magic 8 Ball Predicts Our Financial Future (SB1632) Jan 17, 2025

Show notes

Ready to ring in the new year with a twist? On this episode of Stacking Benjamins, we consult the one and only Magic 8-Ball to make our bold predictions for 2025. Will the stock market be riding high, or is it headed for a tumble? What’s next for Bitcoin, and can Taylor Swift’s love life predict the future? Join Joe, OG, Len Penzo, and Mindy Jensen as they tap into the 8-Ball’s mystical power (or maybe just have a laugh trying) to forecast the year ahead.

But before we get too caught up in the crystal ball, we take a look back at last year’s predictions. The 8-Ball hit some big marks, like predicting Nvidia’s rise, but it also missed a few. Along the way, Mindy shares her early (and hilarious) experience with Berkshire Hathaway, sparking a fun conversation about investing wisdom. And of course, Len brings his signature humor, diving into everything from crypto to drones to the wild world of Taylor Swift fandom.

If you’re in the mood for financial insights, pop culture predictions, and a whole lot of fun, this episode is for you. Whether the Magic 8-Ball is on the money or way off the mark, you won’t want to miss our 2025 forecast. Grab your popcorn, sit back, and join us for an episode packed with surprises!

FULL SHOW NOTES: https://stackingbenjamins.com/magic-8-ball-2024-recap-2025-predictions-1632

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

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