The Stacking Benjamins Show

Latest Episodes:

Your Path to a Cost-Effective Car SB1651 Mar 03, 2025

Show notes

Ever felt overwhelmed by buying a car or managing your time? You’re not alone. Today, we tackle both topics with expert insights and a few unexpected surprises along the way.

Car buying decoded – Joe sits down with Phil Reed, Senior Consumer Editor at Edmunds, to break down the best strategies for buying new or used cars, leasing vs. buying, and negotiating with dealers like a pro.
The ultimate time management playbook – Paula Pant, Dominique Brown, and returning guest Carrie Smith share real-world productivity hacks—whether you're self-employed, working 9-to-5, or just trying to make better use of your day.
Avoiding social media missteps at work – The team dives into the do’s and don’ts of posting while employed.
Email overload? Phone calls running your life? – Smart strategies to take control of your inbox and stop wasting time on endless calls.
Celebrity wealth secrets and entertainment picks – Because financial wisdom can come from surprising places.
A roadside hawk encounter?! – An unexpected story that proves you never know what’s coming next.

With practical advice, engaging discussions, and a few twists you won’t see coming, this episode packs in everything you need to take control of your finances and your time—without taking life too seriously.

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What's In Your Financial "Go Bag"? SB1650 Feb 28, 2025

Show notes

If disaster struck tomorrow, would your financial essentials be ready to grab and go? Today, Joe—along with contributors Paula Pant from Afford Anything, Jesse Cramer from Personal Finance for Long-Term Investors, and our resident expert OG—assemble the ultimate financial go bag. Meanwhile, Doug handles his usual duties as announcer, trivia master, and general chaos instigator.

The must-have documents – Passports, Social Security cards, insurance policies... what belongs in your bag, and what can stay in the filing cabinet?
Cash vs. digital access – How much should you keep in physical cash? And is gold really a smart emergency asset, or just a really heavy way to slow yourself down?
Estate planning and emergency preparedness – The financial moves today that can make a crisis less stressful later.
Password managers: genius or a liability? – We debate whether your digital keys should be stored in the cloud, on paper, or tattooed in invisible ink.
Trivia showdown: Doug tests the team’s knowledge with a question that (probably) has nothing to do with financial preparedness.
Campus co-op stores and Harvard history—why are we talking about this? You’ll find out.

If you’ve been meaning to get your financial house in order for emergencies, this episode has everything you need to build your own financial go bag—without overpacking.

FULL SHOW NOTES: https://stackingbenjamins.com/your-financial-go-bag-1650

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.

Navigating the Insurance Maze (SB1649) Feb 26, 2025

Show notes

Is your insurance setup rock-solid, or are you unknowingly leaving gaps that could cost you big time? Today, we break down the essentials of managing risk in our no-nonsense (but totally entertaining) insurance guide.

How much coverage do you really need? We tackle the must-haves and the unnecessary add-ons that might just be draining your wallet.
Auto, home, life, and disability insurance—what’s essential and what’s overkill? We walk through the key policies that keep you protected without breaking the bank.
Oddball insurance policies—are they worth it? From pet insurance to that ‘just in case’ coverage you saw on late-night TV, we separate the smart buys from the money traps.
A TikTok minute that perfectly sums up the difference between dogs and cats. Trust us, you’ll relate.
Listener questions: Breaking up with a financial advisor—when it’s time to walk away and how to do it right.
Insurance company showdown: Who’s the biggest player in the game, and does size really matter?
DIY money moves: How to take over your own investment accounts without making costly mistakes.

Stackers, this episode is packed with tips, laughs, and real-world insights to help you protect what matters—without wasting a dime. Don't miss it!

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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A Fresh Look at Budgeting Basics (SB1648) Feb 24, 2025

Show notes

Ever feel like your budget is running you instead of the other way around? Today, we’re bringing in Shaun Morgan from The Teacher Money Show and Kristin Wade, budgeting coach at My Budget Coach, to help you flip the script. They’ll share how tracking your expenses is the first (and easiest) step toward financial freedom, why budgeting shouldn’t feel like punishment, and how to make your money work without the guilt.

But wait—there’s more! We’re diving into creative ways to gamify saving, some unexpected solutions for real estate dilemmas (hint: selling isn’t your only option), and why sometimes renting out your home might be the smarter move. And of course, we sprinkle in some personal stories, real-life lessons, and a few side tangents that may or may not include baseball, beer trends, and an ode to Steve Jobs.

What’s Inside Today’s Episode:

Budgeting Basics: How to make your spending work for you.
Tracking Expenses 101: The first step toward a stress-free financial plan.
Finding the Right Budgeting Tools: What actually works?
Gamifying Your Finances: How to make saving and budgeting fun (yes, fun!).
Accountability & Motivation: Why most people quit budgeting—and how to stick with it.

Turning Real Estate Woes Into Wins: If your house won’t sell, here’s what to do next.
Renting vs. Selling: When keeping your home might be the smarter play.
Running a Business on a Budget: The hidden costs and how to stay profitable.

Community Shoutouts & Listener Feedback: Your wins, your questions, and more.

Random Topic: Cancun adventures and off-the-cuff fun.

Key Takeaways from the Episode:

✔️ Budgeting doesn’t mean restriction—it means intentional spending.

✔️ Tracking your money is like using a GPS—it keeps you from getting lost.

✔️ Real estate has more options than just “sell or stay put.” Renting could be a game-changer.

✔️ You don’t have to budget alone. The right tools and accountability partners make all the difference.

✔️ Even Cancun has budgeting lessons. (Or at least a few good stories.)

Tune in now and take the first step toward mastering your budget—without making it feel like a chore.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-take-control-of-your-budget-1648

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.

Is It Time To Dump International Stocks? (SB1647) Feb 21, 2025

Show notes

Is it time to break up with international stocks? They’ve been underperforming U.S. markets for years, so should we finally call it quits, or is there still hope for a global comeback? On today’s episode, Joe, OG, Paula Pant, and Jesse Cramer dig into the great international investing debate.

Are international funds a lost cause? The panel unpacks why they’ve lagged U.S. stocks and whether diversification still makes sense.
Beyond stocks: Exploring other asset classes—private equity, real estate, commodities, and collectibles (because who doesn’t want to invest in Beanie Babies and vintage lunchboxes?).
The $3 coin mystery: Yep, that was a thing. And yes, it’s as weird as it sounds.
Election results and wooden nickels: The intersection of money, history, and questionable currency choices.
Weekend plans and podcast highlights: Because investing is important, but so is having fun.

Of course, it wouldn’t be a Stacking Benjamins episode without some friendly debate, expert insights, and the occasional off-the-wall tangent. Tune in for a laid-back but insightful conversation on making smart investment decisions!

FULL SHOW NOTES: https://stackingbenjamins.com/is-international-investing-dead-1647

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.

When the Job Crumbles: Preparing for Life's Surprises (SB1646) Feb 19, 2025

Show notes

Ever experienced the gut-wrenching moment of losing a job—or worried about what you’d do if it happened? Today, we tackle how to prepare, what to do immediately, and the smartest moves to protect your finances if your job ever disappears. From building an emergency fund to making the most of employer benefits, we’ll walk you through the steps to keep your financial house in order when life throws a curveball.

But that’s not all. Estate planning gets a shake-up thanks to the new Secure Act 2.0, and we’re diving into what it means for inherited Roth IRAs (hint: the government has new rules, and you’ll want to know them).

And because we can’t resist a good detour, we also explore the real cost of horse ownership (spoiler: it’s more than just hay money) and why tide pooling is more financially educational than you’d think. All that, plus trivia, TikTok wisdom (or nonsense), and plenty of lively discussion from the basement crew.

What’s Inside Today’s Episode:

Job Loss Survival Guide: How to prepare before, during, and after a layoff.
Emergency Fund Essentials: Why you need one (and how much is enough).
Navigating Employer Benefits: Making the most of what’s available before you leave.
Secure Act 2.0 & Estate Planning: The new rules around inherited Roth IRAs.
Trivia & The TikTok Minute: Because questionable financial advice is always worth dissecting.
Horse Stackers & Expensive Hobbies: Ever wonder what it really costs to own a horse? We break it down.
Tide Pooling Adventures: A financial lesson wrapped in sea creatures and crashing waves.

Key Takeaways from the Episode:

✔️ Job security is a myth—be ready. Build that emergency fund, update your resume, and keep networking.

✔️ Your employer’s benefits might be your hidden lifeline. Know what’s available before you walk out the door.

✔️ Secure Act 2.0 changes estate planning. If you’re inheriting a Roth IRA, don’t assume the old rules apply.

✔️ Horses aren’t just expensive—they’re financial black holes. But that won’t stop people from trying.

✔️ Tide pooling might be the best investment lesson in disguise. Patience, observation, and avoiding getting pinched—it’s practically a stock market metaphor.

Tune in now to make sure you’re financially prepared—whether it’s for job loss, estate planning changes, or just the unexpected expenses of a very expensive hobby.

FULL SHOW NOTES: https://stackingbenjamins.com/spring-cleaning-your-estate-plan-1646

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.

Innovation, XBox and Your Financial Plan (SB1645) Feb 17, 2025

Show notes

Feeling stuck in your financial plan—or maybe just in life in general? Whether it’s your money, career, or day-to-day habits, a little innovation can go a long way. Today, we’re breaking down how to rethink and restructure your approach to financial planning and work-life balance using lessons from Microsoft (yes, the Xbox folks). Dean Carignan and JoAnn Garbin insights on how to build a system for innovation—because the best financial plans (and lives) aren’t built by accident.

Meanwhile, a woman was scammed out of her savings, and a major financial company had to pay a fine—even though they didn’t actually rip her off. What happened? And what does it mean for how we protect our own money? We’ll break it all down.

Elsewhere in the episode, we discuss why trusted contact forms are crucial for safeguarding elderly relatives’ finances, how OG wants you to rethink your daily money habits, and why the Xbox case study holds lessons for designing a better financial plan. Plus, Doug has thoughts on podcast innovation, trivia, and—because it wouldn’t be a proper basement gathering without it—a hot take or two.

What’s Inside Today’s Episode:

A Woman Gets Scammed, But Who Pays the Price? A big financial firm faces a fine—without actually doing anything wrong.
The Xbox Case Study: What Microsoft’s innovation strategy can teach you about structuring your financial future.
Financial Planning Innovations: Why thinking like an engineer (or a game developer) might help you build a better plan.
Rethinking Your Everyday Financial Habits: OG’s take on how small changes lead to big results.
Trusted Contact Forms & Safeguarding Elderly Relatives: A simple but powerful tool to prevent financial disasters.
Charitable Giving Strategies: How to give smarter, not just more.
Doug’s Trivia Time: A deep dive into financial (and podcast) innovation—because why not?
Building a Network in Retirement: Why relationships matter just as much as money when designing your post-work life.

Key Takeaways from the Episode:

You can’t just wing it with your finances. Microsoft doesn’t build Xbox consoles on a whim—your financial future needs the same level of structured innovation.
Don’t assume big financial firms will protect you. A major company had to pay up even though they weren’t the scammers—learn how to protect yourself before something happens.
Small financial tweaks can make a massive difference. Just like product innovations, incremental changes in your money habits can lead to big wins over time.
Retirement isn’t just about the money. You need a network, a purpose, and a strategy—or you’ll find yourself wealthier but bored out of your mind.

Tune in now to learn how to bring structured innovation into your finances, career, and life!

FULL SHOW NOTES: https://stackingbenjamins.com/the-importance-of-innovation-1645

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.

How Does a Money Nerd Think About "Romance"? (SB1644) Feb 14, 2025

Show notes

Love is in the air—and so are overpriced flowers, extravagant dinners, and some serious credit card regrets. In today’s episode, we tackle the financial pressure of Valentine’s Day and show you how to keep the romance alive without setting your wallet on fire.

Joining us are financial pros Jesse Cramer, Sarah Catherine Gutierrez, and Len Penzo, who help us break down:

The shocking reality of Valentine's Day spending – Who’s dropping the most cash, and is it really worth it?

Avoiding post-holiday financial heartbreak – Strategies to celebrate without swiping yourself into debt.

Creative alternatives to overpriced traditions – Ditch the $200 steak dinner and try these fun, budget-friendly ideas instead.

The cost of love – From babysitting fees to restaurant markups, where is your money really going?

Romantic gestures that don’t break the bank – Because a handwritten note might just score you more points than a last-minute gas station bouquet.

The key to financial harmony in relationships – Talking money before someone drops a fortune on a gift they think you’ll love (but don’t).

Listener tips and budget-friendly adventures – Stackers share their best ideas for a Valentine’s Day that’s memorable and affordable.

Plus, we’ve got trivia, technical mishaps (because what’s love without a little chaos?), and some surprise financial wisdom that might just save your next date night.

Stack your love life and your Benjamins—tune in now!

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Wall Street Creates (Yet Another) Hilariously Bad Investment Product (SB1643) Feb 12, 2025

Show notes

Just when you thought Wall Street had run out of ways to package up risky investments and slap a shiny label on them—here we go again. Today, Joe and OG break down yet another overcomplicated, high-fee, and completely unnecessary financial product. Whether it’s preying on investor fears, promising market-proof returns, or just outright nonsense, we’ll help you spot the warning signs before you end up with a portfolio full of regret.

But that’s not all. A viral TikTok tip about hiring your family members for tax benefits has been making the rounds, so we’ll dive into whether this is actually a genius tax strategy or just another case of the internet handing out half-baked financial advice.

Plus, a listener asks about breaking into financial planning, and we lay out what it really takes—beyond the certifications and credentials (spoiler: sales skills matter). And Doug brings us a trivia question about one of the greatest art heists in history, proving that sometimes the best investment is knowing how to disappear with the Mona Lisa.

Also: Joe saw ‘Wicked’ and has thoughts—mostly about how much better Wonka was.

What’s Inside Today’s Episode:

The Latest Wall Street Gimmick: A financial product you definitely don’t need.
Understanding Risky Investments: How to tell if an ETF, structured note, or annuity is actually worth your time.
Hiring Family for Tax Benefits: A TikTok tax hack that might actually work—if you follow the rules.
Trivia Time with Doug: One of the most famous art heists in history.
Breaking Into Financial Planning: What it takes to switch careers and make it in the industry.
Community Feedback & Upcoming Episodes: A sneak peek at what’s coming next (including our Valentine’s Day special).

Episode Highlights:

What’s in a Name? The ridiculous branding that makes bad investment products sound good.
Bitcoin Meets Structured Protection: The ETF that no one asked for but someone, somewhere, will buy.
Hiring Your Kids for Tax Savings: A loophole with some very real fine print.
How to Become a Financial Planner: Beyond certifications—why understanding people (and sales) matters.
Doug’s Trivia: If you could steal any piece of art, what would it be? Asking for a friend.
Joe’s ‘Wicked’ Review: Spoiler: Wonka was better.

Huge Resource Mentioned in This Episode:

Want to learn more about structured investments? (Just kidding, you really don’t.)

Tune in now and learn how to dodge the latest Wall Street nonsense while making smarter money moves.

FULL SHOW NOTES: https://stackingbenjamins.com/new-crypto-etfs-1643

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.

Are You On Speaking Terms With Your Wallet? (SB1642) Feb 10, 2025

Show notes

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:

🏈 Super Bowl takeaways and why Doug insists commercials count as “investing research”
💰 Your financial habits might just be the biggest red flag in your dating life
🎙️ Shannah Game on money, mindset, and making smarter choices
💔 Rollercoaster relationships—with your wallet and beyond
🧐 Money manifestos: How to rewrite your financial story (without Mom intervening)
🤖 AI's impact on investing, and why OG isn't buying it (literally)
📈 How to keep your portfolio from ghosting you
🤯 Hidden track: Doug’s latest deep dive into bizarre facts—this time, dinosaur vomit

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!

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.

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