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StackingBenjamins.com | Cumulus Podcast Network

Named the Best Personal Finance Podcast by Bankrate.com and Kiplinger, The Stacking Benjamins Show features a light and friendly tone. Hosts Joe Saul-Sehy and OG aim to make financial literacy fun for all as they sit around the card table in Joe's Mom's half-finished basement and talk with experts about personal finance, saving, investing, and important money trends. As Fast Company once wrote, the Stacking Benjamins podcast "strikes a great balance of fun and functional." So join Joe and OG every Monday, Wednesday and Friday as they read your letters, discuss major headlines, and throw in some trivia and laughs for free.

The Stacking Benjamins Show

It's the most wonderful time of the year in the basement, and we're kicking off the holiday season with our biggest, most packed episode yet.

Joe Saul-Sehy, OG, and Neighbor Doug welcome Joel Larsgaard and Matt Altmix from the How to Money podcast for a year-end celebration of everything that mattered in money during 2025. Think of this as the holiday parade of personal finance episodes. There's a lot happening, it's all connected, and you'll want to stick around for the whole thing.

First up, Joel and Matt join the crew for their Top 5 Lessons from the Events of 2025. From AI's real impact on everyday work to market surprises nobody saw coming, this segment unpacks the money moments that actually changed how we think about our finances. These aren't just headlines rehashed. They're the insights that'll help you make smarter moves in 2026.

Then the show shifts to a fascinating trend everyone's noticing but nobody's quite figured out yet. Why is everyone suddenly betting on everything? Prediction markets are exploding, retail investors are taking bigger risks, and the line between investing and gambling feels blurrier than ever. Joe, OG, Joel, and Matt dig into what's driving this shift, whether it's brilliant or reckless, and how to think about risk when it seems like the whole world just discovered the casino.

But wait, there's more. Nick from Alaska calls in with a real-world budgeting challenge that proves even the most prepared Stackers face seasonal money surprises. His situation sparks the kind of practical, helpful conversation this show does best.

And because this is a holiday kickoff episode, we're wrapping with big news about the Stacking Benjamins Vault, the new tool designed to help you organize and protect your most important financial documents without the headache.

This episode has everything. Big ideas, real questions, legendary guests, surprise calls, and the energy of a show that knows the best episodes are the ones where there's almost too much good stuff to fit in. Welcome to the holiday season, Stacker style.

What You'll Walk Away With:

• Joel and Matt's Top 5 Money Lessons from 2025 that actually matter going forward

• How AI really affected work and income this year in practical, not theoretical, ways

• Why prediction markets and betting culture are suddenly everywhere and what it means for investors

• Whether the shift toward riskier investments is smart adaptation or dangerous groupthink

• Nick from Alaska's budgeting challenge and the solutions the crew offers in real time

• An inside look at the Stacking Benjamins Vault and how it helps you organize what matters most

• The perfect energy boost heading into holiday episodes and a new year of smarter money moves

This Episode Is For You If:

• You want the year-end money recap that feels like a celebration, not a lecture

• You've noticed everyone's suddenly betting on elections, sports, and markets and wonder what's going on

• You love episodes with special guests, surprise calls, and enough happening to keep you engaged the whole way

• You want to head into the holidays feeling smarter about money, not more anxious

• You're ready to kick off the season with the Stacking Benjamins crew at their absolute best

After You Listen, Share This:

What was your biggest money lesson from 2025? And have you noticed yourself (or people you know) getting more comfortable with risky bets lately? Drop your thoughts in the Spotify comments or the Basement Facebook group because this episode kicks off our holiday run, and we want to hear what's on your mind heading into 2026.

FULL SHOW NOTES: https://stackingbenjamins.com/year-end-lessons-with-the-runners-up-of-the-charity-challenge-1777

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

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The Holiday Kickoff Special: 2025 Lessons, Risky Bets, and an Alaska Surprise (SB1777)

Before you charge into a new year with fresh goals, shiny spreadsheets, and unrealistic optimism, it's worth doing the one thing most people skip. Looking back honestly at what just happened.

Joe Saul-Sehy, OG, Neighbor Doug, Paula Pant (Afford Anything), and Jesse Cramer (Personal Finance for Long Term Investors) gather for an end-of-year roundtable to unpack the financial, personal, and behavioral lessons that 2025 handed us. Sometimes those lessons arrived gently. Sometimes they shoved us face-first into reality. Either way, this episode isn't about predictions for what's coming. It's about understanding the patterns from what already happened.

The team digs into what diversification actually meant this year when some of the old rules stopped working the way they used to. They explore why emotional reactions to headlines still cost investors real money, even when everyone knows better. And they examine how policy noise (tariffs, political drama, market freakouts) reminded us once again that short-term chaos rarely deserves long-term decisions.

Along the way, the conversation touches on housing lessons learned, family priorities that got re-examined, and AI's quiet but growing influence on work, productivity, and opportunity. The thread running through it all? Financial planning only works when it serves the life you're trying to build, not the other way around.

This episode balances big-picture thinking with real-life reflection. It's the kind of honest look back that actually helps you move forward smarter instead of just louder.

What You'll Walk Away With:

• The most important financial lessons 2025 taught investors, whether they actually listened or not

• How AI quietly changed work, productivity, and opportunity in ways that matter for your money decisions

• Why diversification looked different this year and what investment principles still held up under pressure

• How market volatility exposed emotional blind spots you might not have known you had (and how to fix them)

• What the housing market taught us about patience, expectations, and timing

• Why year-end reflection beats year-end predictions every single time

• How family dynamics, personal values, and money planning intersect more than anyone likes to admit

This Episode Is For You If:

• You want to learn from 2025 before setting goals you'll abandon by February

• You made some money decisions you're proud of and some you'd rather forget

• Market headlines changed your behavior this year and you're wondering if that was smart

• You're tired of prediction content and want actual reflection on what already happened

• You believe getting smarter about money means being honest about what you got wrong

Before You Hit Play, Think About This:

What money decision in 2025 are you most proud of, and which one taught you the biggest lesson? Going into 2026, what one financial habit would make the biggest difference if you actually stuck with it? Bring those thoughts into the Facebook group or drop a comment because your reflections might help another Stacker avoid learning the same lesson the hard way.

FULL SHOW NOTES: https://stackingbenjamins.com/top-money-lessons-of-2025-1776

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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What 2025 Taught Us About Money (And What Actually Matters for 2026) SB1776

What if "giving back" isn't about writing bigger checks but about using what you're already great at? Most people think philanthropy is reserved for people with their names on buildings. That assumption keeps them from realizing they already have something valuable to give.

Joe Saul-Sehy, OG, and Neighbor Doug welcome John Studzinski, managing director at PIMCO and founder of the Genesis Foundation, for a conversation about generosity, purpose, and impact that actually applies to everyday Stackers. John challenges the whole concept of "philanthropy" as something for the ultra-wealthy and reframes giving as a muscle anyone can build using time, talent, and intention instead of just cash.

The conversation reveals how you can create meaningful impact right now, regardless of your bank balance. Whether you're great at organizing, teaching, listening, or solving problems, those skills matter more than you think. John breaks down how to identify your personal talent for impact and why intentional giving beats reactive charity every single time.

Then the show shifts to retirement planning, specifically how to design a glide path that works with your behavior instead of fighting it. Joe and OG break down how to manage risk as you age, why annuities keep showing up in retirement conversations, and why smart planning focuses less on chasing perfect returns and more on creating stability you can actually live with. Because the math might say one thing, but your ability to sleep at night matters just as much.

Along the way, the crew takes a detour into ChatGPT's potential future, explores a few behavioral finance truths that hit uncomfortably close to home, and wraps with a pop culture review reminding us that money decisions never happen in a vacuum. This episode is about aligning your resources (financial and otherwise) with the life you actually want to live.

What You'll Walk Away With:

• Why "giving" is a better word than "philanthropy" and why that shift in language actually matters

• How to identify your personal talent for impact even without significant wealth

• Why generosity works best when it's intentional and strategic rather than reactive

• How retirement glide paths actually work and why your behavior matters more than the math

• The role annuities can play in reducing retirement anxiety without sacrificing everything

• Why percentages can be misleading, real dollars tell better stories, and context is everything

• How fear, FOMO, and age quietly shape your investment decisions in ways you might not notice

• Permission to build a retirement plan around stability instead of maximum growth

This Episode Is For You If:

• You want to give back but think you need more money before you can make a real difference

• You're approaching retirement and tired of advice that ignores how you actually feel about risk

• You've wondered if annuities deserve their bad reputation or if there's something there

• You want your money decisions to reflect your values, not just optimize for returns

• You believe purpose and planning should work together, not compete

Before You Hit Play, Think About This:

What's a talent you already have that could create more impact than money alone? And when it comes to retirement investing, what decision do you know is emotional but still struggle with? Drop your answers in the comments because John's perspective on giving and the crew's take on retirement planning might shift how you think about both.

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How to Give Back Without Being Rich + Building a Smarter Retirement Plan (SB1775)

Some episodes help you protect your money. Some help you protect everything your money makes possible. This episode does both.

Joe Saul-Sehy and OG welcome fire safety expert Steve Kerber from UL's Fire Safety Research Institutes, who delivers simple, practical, "do this today" steps that dramatically increase your home's safety. From upgrading outdated smoke alarms to understanding lithium-ion battery risks to spotting hidden hazards most people walk past every single day, Steve gives everyday Stackers the tools to keep their homes and families safer. This isn't scare tactics. It's straightforward guidance from someone who's spent his career studying what actually prevents fires and saves lives.

Then the show shifts gears for the headline segment. Joe and OG unpack T. Rowe Price's latest Global Retirement Survey to explore what savers around the world are most anxious about right now. How are people adapting to inflation? Are retirement expectations shifting across different countries? What can you learn from how others are handling the same fears you probably have? The data reveals patterns that might surprise you and insights you can actually use to build more confidence in your own retirement planning.

Between these two segments, you'll get Doug's trivia throwdown, a TikTok detour through airport lounge mythology, and a few classic basement moments that remind you why this show mixes serious topics with serious fun. It's a wide-ranging episode packed with actionable takeaways and a good reminder that your financial plan works best when your home, your health, and your long-term outlook are all protected.

What You'll Walk Away With:

• The small home safety upgrades that make the biggest difference in fire prevention

• Why smoke alarms fail more often than you think and how to pick the right replacement

• Lithium-ion battery safety covering where to store them, what to avoid, and which myths to ignore

• How real-world fire prevention thinking overlaps with smart financial planning habits

• What savers around the world worry about most when it comes to retirement

• How inflation, longevity concerns, and economic uncertainty are reshaping retirement expectations globally

• Practical steps to feel more confident about your long-term retirement plan based on what the data reveals

• Permission to take simple safety steps today that your future self will thank you for

This Episode Is For You If:

• You can't remember the last time you checked your smoke alarms (or know they're overdue for replacement)

• You've got lithium-ion batteries around the house but aren't sure if you're storing them safely

• You're curious what retirement worries look like around the world and how yours compare

• You want retirement insights based on actual data instead of just one expert's opinion

• You believe protecting what you have is just as important as growing what you're building

Before You Hit Play, Ask Yourself:

When's the last time you actually tested your smoke alarms or checked their expiration dates? And what's your biggest retirement worry right now? Drop both answers in the comments because Steve's fire safety tips and the global retirement data might address fears you didn't even realize were universal.

FULL SHOW NOTES: https://stackingbenjamins.com/holiday-fire-safety-tips-steve-kerber-1774

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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The Fire Safety Steps You're Skipping (Plus: What the World Worries About in Retirement) SB1774

Does more money make life easier, or does it just give you more expensive problems to solve? Most people assume that once they start earning more, their financial life will finally calm down and organize itself. Then they get the raise or the promotion or the business success, and somehow things feel just as chaotic as before, just with bigger numbers involved.

Joe Saul-Sehy is joined by Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and OG to explore why "more" isn't always "simpler." The crew digs into early money mistakes they'd all like to forget, the weird psychological traps that show up as income grows, and why your brain doesn't automatically upgrade its money management skills just because your paycheck did.

The conversation gets real about the hidden mental challenges that come with wealth growth. Decision fatigue gets worse, not better. Lifestyle creep sneaks in wearing a very convincing disguise. And suddenly you're agonizing over choices that used to be simple, because now you can afford multiple options and none of them feel obviously right. If you've ever wondered why your financial life didn't magically self-organize the moment you started earning more, this roundtable has your answers.

The crew also tackles listener questions about building budgeting habits that actually stick, finding genuine financial confidence, and creating systems that scale with your life instead of working against it. Because the goal isn't just to make more money. It's to build a life that feels manageable and intentional at whatever income level you're at.

Plus, Doug delivers a trivia showdown featuring fierce competition, questionable strategy, and what might be the most overthought trophy dilemma in basement history.

What You'll Walk Away With:

• Why more income doesn't automatically reduce financial stress and often creates new complications

• The hidden mental traps people fall into as their wealth grows and how to spot them early

• How Paula, Jesse, OG, and Joe think about building lasting financial confidence at any income level

• Practical budgeting strategies that work whether you're making $50K or $500K

• Why simple pleasures matter more (not less) as your money grows

• The surprising ways earning more actually complicates everyday decisions

• Listener Q&A on habits, organization, and creating systems that smooth out financial chaos

• Permission to admit that making more money didn't solve everything like you thought it would

This Episode Is For You If:

• You're earning more than you used to but somehow don't feel more in control

• You assumed financial stress would decrease with income but it just shifted to different problems

• You're stuck between multiple good options and can't figure out why that's so paralyzing

• You want to hear successful people admit that more money created complications they didn't expect

• You're building wealth but want to make sure you're also building a life that feels good

Before You Hit Play, Think About This:

What's one financial decision that got harder (not easier) as you started earning more money? Drop your answer in the comments because this roundtable proves you're definitely not the only one experiencing this paradox.

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Does More Money Actually Make Life Easier? (Spoiler: Not Really) SB1773

Walking away from a secure city government job to eventually run one of the world's most recognizable handbag brands sounds like fiction. For Lew Frankfort, it became his career story, and the path between those two points is exactly what makes this conversation so valuable.

Lew joins Joe Saul-Sehy and OG in the basement to break down how a combination of discipline, curiosity, and what he calls "magic and logic" shaped his journey from city hall to the corner office at Coach. This isn't just inspiration for aspiring executives. Lew's insights about making better decisions, taking calculated risks, and building a meaningful life apply whether you're 25 or 55, whether you're climbing the ladder or considering jumping to a different one entirely.

Lew shares how preparation became his secret advantage, why curiosity beats confidence during major transitions, and what he learned about leadership while helping transform Coach into a global powerhouse. His framework for balancing intuition with analysis gives the Confident Explorer a practical lens for evaluating their own big moves, career pivots, or midlife reinventions.

Then Joe and OG shift gears to tackle a different kind of transition. The first year of retirement. When excitement runs high and "go-go" energy meets newfound freedom, spending can spiral in ways that derail decades of careful planning. They break down the crucial financial decisions retirees face right out of the gate, why that first year can be surprisingly dangerous, and how to set yourself up for long-term stability without killing the joy of finally having time to live.

Plus, Doug delivers trivia involving time travel and underwear, because even episodes about CEO wisdom and retirement planning need a reality check from the basement.

What You'll Walk Away With:

• How Lew Frankfort pivoted from city government work to leading Coach and what that path teaches about career reinvention

• The "magic and logic" framework anyone can apply to big decisions and career moves

• Why curiosity and thorough preparation matter more than confidence when making your next leap

• Leadership lessons from someone who helped build a global brand from the inside

• What retirees absolutely must understand about spending during that crucial first year

• Why the "go-go years" of early retirement can wreck your finances if you're not careful

• Strategies for aligning your early retirement excitement with long-term financial stability

• Permission to reinvent yourself at any age, armed with both inspiration and practical wisdom

This Episode Is For You If:

• You're considering a career change but worried you're too far along to pivot

• You want to understand how successful people actually made their big moves

• You're approaching retirement and want to avoid the spending traps that catch most people

• You're curious how to balance intuition with analysis when making major life decisions

• You believe it's never too late to build something meaningful or try something new

Before You Hit Play, Think About This:

What's one career move or life transition you've been thinking about but haven't pulled the trigger on yet? What's actually holding you back? Drop your answer in the comments because Lew's story might be exactly the perspective shift you need to take that next step.

FULL SHOW NOTES: https://www.stackingbenjamins.com/https-stackingbenjamins-com-lou-frankfort-bagman-1772/

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

Enjoy!

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

Magic and Logic: How Lew Frankfort Built Coach (Plus: Don't Make This Retirement Mistake (SB1772)

Holiday parties make you want to hide behind the cheese tray. Gift-giving season makes your budget cry. This episode is your survival guide for both.

Joe Saul-Sehy, OG, and Neighbor Doug welcome Pulitzer Prize-winning author Charles Duhigg to turn holiday small talk from awkward endurance test into something you might actually enjoy. Whether you're facing the office party, a family gathering with that cousin who won't shut up about crypto, or the neighborhood potluck where you know exactly three people, Charles reveals how to walk into any room with confidence, even if you're an introvert who'd rather be home watching movies.

The secret? Super communicators aren't the loudest people in the room. They're the ones asking better questions, reading the conversation correctly, and making others feel heard. Charles breaks down the skills that turn painful small talk into genuine connection, and why introverts actually have hidden advantages at holiday gatherings (yes, really).

Then the crew tackles the other holiday stressor of gift-giving that doesn't demolish your December budget. Joe, OG, and Doug explore the rising trend of secondhand gifting. It's not just about saving money (though your wallet will thank you). It can be more meaningful, more creative, and kinder to both your finances and the planet. From thrifted treasures to thoughtful "found" gems, they share how to give smarter instead of just spending more.

Plus, Doug's toilet paper trivia arrives right on schedule (because what's a holiday episode without something unexpected?), along with stories about neighbors behaving badly and a brief tour through apps you forgot you're still paying for.

What You'll Walk Away With:

• Charles Duhigg's framework for turning small talk into actual connection without feeling fake

• Why introverts have secret advantages at holiday parties and how to use them

• Smart, budget-friendly gifting strategies that feel thoughtful rather than last-minute or cheap

• The case for secondhand gifts and how to do it in a way that feels special

• How to avoid blowing your holiday budget without looking (or feeling) stingy

• Creative ways to personalize gifts without overspending or resorting to gift cards

• Why communication skills affect both your happiness and your financial decisions

This Episode Is For You If:

• Holiday small talk feels like torture and you'd rather shovel snow

• You want to give meaningful gifts but refuse to wreck your January budget doing it

• You're an introvert dreading the season of forced social interaction

• You're tired of generic gift guides telling you to "just spend less" without actual ideas

• You believe better conversations and smarter spending are both learnable skills

Before You Hit Play, Ask Yourself:

What's the most meaningful non-new gift you've ever given or received? Think about why it mattered. That's the kind of gifting Charles and the crew are talking about. Drop your story in the comments because we're building the anti-Amazon holiday gift playbook together.

FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-actually-enjoy-holiday-small-talk-1771/

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

Enjoy!
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How to Actually Enjoy Holiday Small Talk (And Give Better Gifts for Less) SB1771

Here's the problem with most frugality advice: it makes you feel like a monk who's taken a vow of joylessness.

Joe Saul-Sehy and Neighbor Doug gather the roundtable crew—Paula Pant (Afford Anything), Jesse Cramer (Personal Finance for Long-Term Investors), and Andy Hill (Marriage, Kids, and Money)—to prove that frugality isn't about deprivation. It's about designing a life that feels good and costs less.

The conversation gets real fast: what's the difference between thoughtful frugality and soul-crushing penny-pinching? How do you cut spending without cutting joy? And why do some people thrive on frugal challenges while others just end up resentful and burnt out?

The crew shares their own tactics, from "shopping your fridge" (a shockingly high-ROI habit most people ignore) to the power of frugal sprints instead of permanent deprivation mode. They break down how to align your spending with your actual values instead of society's expectations, why raising income often beats shaving another $3 off your grocery bill, and how to turn frugality into something your kids actually want to participate in (no guilt trips required).

You'll also hear about the expenses each of them refuses to cut no matter how frugal they get, because smart money management isn't about eliminating everything; it's about keeping what matters and ditching what doesn't.

Plus: stories about mystery freezer leftovers, subscription fees that sneak in like cat burglars, and Doug's perspective on... well, whatever Doug decides matters that day.

What You'll Walk Away With:

• The difference between frugality that improves your life and penny-pinching that just makes you miserable

• Why "shopping your fridge" might be the highest-return grocery habit you'll ever adopt

• How to design spending around your actual values instead of just cutting blindly

• The power of "frugal sprints"—short-term challenges that work without long-term burnout

• How to involve your kids in frugal habits without making them feel deprived

• Why focusing on raising income often matters more than obsessing over tiny budget cuts

• Which expenses the pros refuse to cut—and why knowing your "worth it" list matters

This Episode Is For You If:

• You want to save money but refuse to live like you're broke when you're not

• Traditional frugality advice makes you feel guilty about things that actually bring you joy

• You're trying to cut spending but can't figure out where to start without feeling deprived

• You want to model smart money habits for your kids without making them fear spending

• You're tired of finance advice that assumes everyone should want the same lifestyle

Before You Hit Play, Think About This:

What's the one expense you refuse to cut, no matter how frugal you get? And what does that tell you about what actually matters to you? Drop your answer in the comments—we want to know what's on everyone's "worth it" list.

FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-save-money-without-making-your-life-miserable-sb1770/

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

How to Save Money Without Making Your Life Miserable (SB1770)

Here's something nobody tells you: knowing how to make money is easy compared to knowing how to spend it well.

Morgan Housel, bestselling author and one of the sharpest minds in personal finance, is back in the basement with Joe Saul-Sehy, OG, and Neighbor Doug to tackle the question most financial advice completely ignores: why do we spend the way we do, and how can we get better at it?

This isn't about budgeting apps or cutting lattes. It's about understanding the psychology underneath every swipe of your card. Morgan shares stories from his early days working valet for the ultra-wealthy—the spending patterns he observed, the misery he witnessed, and the lessons that changed how he thinks about money forever. Turns out, having more money doesn't automatically make you better at spending it. In fact, it often makes you worse.

The conversation digs into what actually creates happiness (spoiler: it's not more stuff), why contentment matters more than your net worth, and how true financial independence isn't about the size of your portfolio—it's about the freedom to make choices that align with your actual values. Morgan also breaks down what Warren Buffett's retirement announcement reveals about staying grounded while building wealth, and why comedians might understand money better than most economists.

Plus: Doug takes a trivia detour to a surprisingly risqué national park (because of course), and the crew wraps with binge-worthy recommendations for your next couch night.

If you're tired of chasing more and ready to figure out what enough actually looks like, this episode is required listening.

What You'll Walk Away With:

• Why spending money well is a psychological skill, not a math problem—and how to develop it

• What Morgan learned about wealth and misery from parking cars for millionaires in their driveways

• The hidden drivers behind your financial decisions (and how to spot them before they derail you)

• Why contentment—not consumption—is the real key to long-term happiness

• What true financial independence actually means (hint: it's not a number in your bank account)

• How Warren Buffett's approach to retirement reveals timeless principles about money and legacy

• Simple guiding principles to help you spend smarter and live calmer

This Episode Is For You If:

• You've hit financial goals but still don't feel satisfied

• You're tired of spending money on things that don't actually make you happier

• You want to understand why you make the money decisions you do (even the questionable ones)

• You're curious what actually separates people who enjoy their money from people who just have it

• You believe there's more to financial success than just accumulating more

Before You Hit Play, Think About This:

What's one purchase you made that brought way more joy than its price tag would suggest—and can you figure out why? That's the kind of spending Morgan's talking about. Drop your answer in the comments—the basement wants to hear what actually brought you happiness.

FULL SHOW NOTES: https://www.stackingbenjamins.com/the-art-of-spending-money-with-morgan-housel-1769/
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Morgan Housel: Why You Spend Money (And How to Do It Better) SB1769

Let's be honest: taxes feel like that thing you're supposed to understand but somehow never learned, and now you're too embarrassed to ask.

Joe Saul-Sehy, OG, and Neighbor Doug welcome Hannah Cole—artist-turned-tax-pro and author of the brand-new book Taxes for Humans—to finally explain taxes in language that doesn't require a CPA license to understand. Hannah's built her career translating tax code for freelancers, side hustlers, and small business owners who just want to know what they can deduct, what'll get them audited, and how to stop drowning in shoebox receipts.

She breaks down the real difference between a legitimate business expense and wishful thinking, how to track startup costs without losing your mind, and why the bookkeeping system that works is the one you'll actually use (spoiler: it doesn't have to be fancy). Whether you're launching a side gig, running a creative business, or just trying to keep the IRS from ruining your holiday season, Hannah's got the roadmap.

Then Joe and OG shift gears to tackle the "AI bubble" conversation everyone's having—is this tech hype justified, or are we watching 1999 all over again? They break down how to think about market froth without panicking, why smart investors don't build their strategy around TikTok prophets predicting doom, and how to prepare your portfolio for volatility without making fear-based moves.

Plus: Doug delivers trivia about Richard Pryor's Blazing Saddles days, because even tax talk deserves a palate cleanser.

What You'll Walk Away With:

• Tax basics explained in actual human language (finally)—what counts as a deduction and what's just wishful thinking

• How to set up simple, sustainable bookkeeping systems for side gigs or small businesses that you'll actually maintain

• The smartest way to track startup expenses without drowning in receipts or spreadsheets

• Why the IRS isn't as scary as you think when you've got your basics covered

• How to think about AI market hype without getting swept up in either the euphoria or the panic

• Smart strategies for preparing your portfolio for volatility without making emotion-driven decisions

• Why the right tax and investing systems buy you back time, creativity, and peace of mind

This Episode Is For You If:

• You've been winging it on taxes and know you're probably missing deductions (or making mistakes)

• You run a side hustle but have no idea what you can actually write off

• Tax season makes you anxious because you're never sure if you're doing it right

• You're hearing AI bubble talk everywhere and wondering if you should be worried about your investments

• You want systems that are simple enough to actually follow, not perfect enough to abandon by February

Before You Hit Play, Think About This:

What's the tax mistake you wish you could warn your younger self about? Drop it in the comments—we're all learning here, and sometimes the best lessons come from what we got wrong the first time.

FULL SHOW NOTES: https://www.stackingbenjamins.com/tax-basics-for-side-hustlers-ai-market-tips/

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The Tax Basics You Should've Learned Years Ago (But Nobody Taught You) SB1768

We're finishing this week strong with today's rewind episode. Featuring Joe, Len Penzo, and Paula Pant, this roundtable has our group looking back at their 20's. What sort of money education would have made their lives easier? Later on the show, the group asks themselves: what's the deal with tipping? And should you tip the takeout host? When is it appropriate to leave a tip? The gang answered all that, and more, on today's episode.
PLUS, in our FinTech segment, we talked to Ross Kimbarovsky from Respect. Worried about elder care for your relatives? Ross and his team rolled out some new systems to address the issues in elder care. 
We'll be back on Monday with a whole new batch of fresh episodes. See you then!
 
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Things We Wish We Knew About Money When We Were 20 w/ an intro to Respect (SB RWD 83)

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