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Ever feel like you're stuck in a rut, spinning your wheels, or just running low on motivation? Today, we crack the code on sustaining drive and avoiding complacency with former sports agent Molly Fletcher, who’s worked with some of the biggest names in sports and has been dubbed the female Jerry Maguire. She breaks down the fine line between contentment and coasting, plus shares keys to staying at the top of your game—from managing energy to embracing adversity like a pro.
But wait, there’s more! Len Penzo (yes, of LenPenzo dot com fame!) joins us as guest co-host, bringing his usual mix of wisdom, dry wit, and probably a few thoughts on sandwich prices.
And if you think motivation is tough, try navigating the world of credit—because while ambition is great, bad credit can still trip you up. From student loan pitfalls to practical credit repair tips, we cover what younger folks (and honestly, all of us) need to know about keeping those numbers in check.
In this episode:
Molly Fletcher on Peak Performance – Lessons from a top sports agent on how to stay motivated without burning out.
Complacency vs. Contentment – Are you stuck or simply satisfied? Molly breaks it down.
Managing Energy Like a Pro – Tom Izzo swears by it, and so should you.
Credit Crash Course – What happens when student loans go delinquent, and how to fix the damage.
The Living Without Credit Debate – Is a debt-free life possible, or just a financial myth?
Doug & OG’s Ski Slope Disaster – A story of poor decisions, gravity, and bruised egos (hilarious in retrospect).
Len Penzo's Tips for Improving Credit Scores – Because nobody budgets quite like Len.
Whether you need a motivation boost, a credit check-up, or just a good laugh at Doug’s expense, this episode has you covered.
🎧 Tune in for wisdom, financial hacks, and some après-ski storytelling you won’t want to miss!
FULL SHOW NOTES: Add show notes url here. Be sure to please include https://www at the beginning of the show notes url that makes it clickable on YouTube
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 start a new financial goal feeling unstoppable, only to lose momentum when life gets in the way? Staying motivated isn’t just about working harder—it’s about working smarter.
Today, Joe and OG take a deep dive into Dynamic Drive, the key to keeping your financial momentum going without burnout. We’ll break down the seven essential pillars—mindset, energy, discipline, curiosity, resilience, connection, and confidence—so you’re ready to hit the ground running when we welcome former sports agent Molly Fletcher on Wednesday.
💰 In this episode:
Why motivation fizzles out—and how to make it last
The seven keys to Dynamic Drive (and how to apply them to your finances)
How milestones and energy management keep you on track
Tax strategies for selling shares—FIFO, LIFO, or average cost? Which method helps you keep more of your hard-earned Benjamins?
What cowboy fencing teaches us about peak performance (yes, that’s a thing)
Plus, Doug serves up a sports trivia challenge—because what’s financial motivation without a little fun?
👉 Listen in now and get fired up—without burning out!
FULL SHOW NOTES: https://stackingbenjamins.com/how-to-create-a-sustainable-drive-1657
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 guilty about that $7 airport coffee or the mystery fees that somehow turn your $15 DoorDash order into a $40 financial regret? You’re not alone. This episode, Joe Saul-Sehy is joined by Paula Pant (Afford Anything) and Justin Peters (The Struggle Is Real) to unravel the sneaky ways convenience drains our wallets.
In this episode:
Airport Food: The Ultimate Financial Heist – Why does a sad turkey sandwich cost more than a steak dinner? We investigate.
Concert Tickets & Junk Fees – You found $50 tickets… but somehow the total is now $127? Yep, we’ve been there.
The True Cost of Convenience – From Uber Eats to express shipping, when is paying extra worth it—and when are we just being lazy?
Trivia Time: Pie Day Special! – Who knew McDonald's pie sales could spark heated debate? Well, now we all do.
Wedding Costs Gone Wild – Creative ways to cut costs without making your guests eat ramen.
The Ben Franklin Effect & Social Hacks – Want better connections without breaking the bank? Turns out, old Ben had some wisdom on that, too.
All this, plus some hilarious personal finance confessions that will make you feel better about your last impulse buy.
🎧 Tune in, laugh, and learn how to keep more of your Benjamins!
FULL SHOW NOTES: https://stackingbenjamins.com/places-we-know-were-overpaying-1656
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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Choosing the Best Tax Software for Your Needs
Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution.
Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year.
H&R Block’s virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to.
Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions.
Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table.
Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix.
Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations.
If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence.
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 if working for yourself could be the game-changer your finances need? Grant Sabatier thinks so, and today, he’s diving into the realities of entrepreneurship—from smart strategies to potential pitfalls.
Where to start if you’re considering entrepreneurship – Not every side hustle is a winner, so how do you know if this path is right for you?
The power of systems and constraints – Why guardrails and structure matter more than unlimited freedom.
Pricing strategies and finding customers – Because even the best ideas need paying customers.
Entrepreneurial misconceptions – Spoiler: It’s not all Ferraris and private jets.
Can your wedding be a tax deduction? – We explore the entertaining but highly questionable ways some people try to make this work.
Meanwhile, Doug serves up trivia on the highest-grossing console game ever (bet you won’t guess it). And if you stick around long enough, let’s just say there may or may not be a discussion about a comedy movie that turns financial struggles into pure entertainment. But, you know… no promises.
If you’ve been toying with the idea of starting your own thing, this episode is packed with insights, real talk, and a few surprises along the way.
FULL SHOW NOTES: https://stackingbenjamins.com/unlock-your-inner-entrepreneur-with-grant-sabatier-1654
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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Feeling the pressure to constantly tweak your investments? Today, we uncover the surprising benefits of financial inaction with insights from CFP Dana Anspach, Len Penzo, and OG. We dive into the wisdom of sometimes doing nothing—because, as it turns out, sitting on your hands (financially speaking) can be a power move.
Why lazy portfolio management might be the smartest strategy you’ll ever adopt (spoiler: it involves less work).
The power of downtime—turns out, stepping away from your money might actually make you richer.
Why your future self will thank you for setting up auto-pay (hint: fewer late fees, more naps).
The sneaky ways peer pressure messes with your finances—and how to keep the Joneses from running your budget.
When rebalancing your portfolio is necessary…and when it’s just a fancy way to micromanage yourself.
A wildly unexpected insurance claim (because finances are never boring in the basement).
Oh, and Doug’s got a trivia question about a particularly controversial activity that was banned—because, apparently, not everything fun is legal.
Stick around for weekend plans, final thoughts, and maybe even a surprise or two (because we like to keep you on your toes).
This episode originally aired on June 10, 2022. Please disregard any mention of current events.
The original show notes can be found here.
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 great financial plan isn’t just about numbers—it’s about creating a roadmap that turns dreams into reality. Today, Joe and OG take a trip down memory lane, reflecting on their favorite parts of building a great financial plan. Whether you're tackling long-term goals, fine-tuning your tax strategy, or simplifying complex decisions, they’ll walk you through the key elements that turn financial chaos into a well-oiled machine.
Breaking down big goals into bite-sized wins – Because climbing a financial mountain is easier when you focus on one step at a time.
The magic of tax strategies – Why a little planning now can keep more Benjamins in your pocket later.
Risk management done right – Avoiding financial pitfalls so your plan stays strong, no matter what life throws your way.
The power of simple solutions – Complexity doesn’t always mean better. Sometimes, the best financial strategies are the easiest to execute.
The role of a financial guide – Whether you DIY your plan or bring in an expert, knowing when to get guidance is a game-changer.
Meanwhile, Doug tackles a ‘Winnie the Pooh’-inspired predicament (honey jars may or may not be involved) and drops some surprising trivia on the massive market value of antidepressant drugs.
If you’re ready to streamline your financial life and celebrate your progress along the way, this episode is packed with insights, strategy, and a few unexpected twists.
This episode originally aired on January 18, 2023. Please disregard any mention of current events.
The original show notes can be found here.
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 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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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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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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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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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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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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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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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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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!
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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!
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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. 😬
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!
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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.)
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!
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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.
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!
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