The Stacking Benjamins Show

What separates people who build lasting wealth from people who just chase the next hot investment? David Greene from BiggerPockets has a clear answer, and it's not what most people want to hear.

Joe Saul-Sehy and OG revisit a standout 2023 conversation with David that still resonates today. His story isn't about shortcuts, hacks, or getting lucky. It's about skill building, discipline, and learning to turn everyday work into long-term opportunity. From scooping ice cream at Baskin Robbins to building a successful real estate career, David breaks down what actually creates momentum over time and why "passive income" still requires serious intention.

This episode showcases the kind of conversation that belongs in the vault. David explains what makes work feel worth it, how to develop skills that compound, and why the unsexy fundamentals matter more than the flashy strategies everyone's talking about. If you're tired of hype and ready for substance, this interview delivers.

The show also tackles two critical protection topics. Adam Barowy from UL's Fire Safety Research Institute joins to explain the real (and often overlooked) risks of lithium-ion batteries in e-bikes, scooters, and everyday devices. He shares practical steps every family can take to reduce fire risk without panic or overreaction.

Then Joe and OG field a listener question about keeping family property in the family. The discussion explores estate planning tradeoffs, communication challenges, and how to think through shared ownership without creating future conflict.

Every segment connects to the same core idea. Building a life that's not only financially strong but resilient, safe, and meaningful.

What You'll Walk Away With:

• David Greene's framework for building wealth through skill mastery, not investment shortcuts

• Why "passive income" is never truly passive and what actually makes work sustainable long term

• Practical fire safety guidance for lithium-ion batteries you probably already own in your home

• Simple steps to reduce household fire risk based on real research, not fearmongering

• Thoughtful estate planning insights for preserving family property across generations

• How to think about money not just as growth but as protection and stewardship

This Episode Is For You If:

• You're tired of wealth-building advice that sounds too good to be true

• You want to hear how someone actually built success through discipline and skill development

• You've got lithium-ion batteries around the house and never thought twice about fire safety

• You're thinking about how to pass property or wealth to the next generation without creating conflict

• You believe the smartest money moves involve both growing and protecting what you have

Before You Hit Play, Think About This:

What's one area of your financial life where you're focused on growth but might need more protection or structure? Share your thoughts in the Spotify comments or bring the discussion into the Basement Facebook group because this episode tends to spark great follow-up conversations.

Sometimes the smartest money move isn't about earning more. It's about keeping what you've built safe and aligned with what matters most.

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Is the constant push to be great quietly making life (and money) harder than it needs to be?

This vault-worthy episode from 2023 hits differently, especially during a season when expectations run high and energy can run low. Joe Saul-Sehy is joined by Len Penzo, Paulette Perhach, Diania Merriam, and special guest Stephanie O'Connell Rodriguez for a candid roundtable about ambition, procrastination, perfectionism, and the surprising freedom that comes from choosing good over exhausting.

Instead of chasing flawless systems or ideal outcomes, the conversation explores what actually moves the needle in real life. Building momentum. Removing friction. Letting go of the idea that every decision has to be optimized. Whether it's money habits, career goals, or simply getting unstuck, this episode offers a calmer, more sustainable way forward without lowering your standards or your future.

Along the way, the group shares personal stories, practical strategies, and a few moments that only happen when smart people stop pretending they've got it all figured out. It's thoughtful, honest, and exactly the kind of perspective many Stackers didn't know they needed.

What You'll Take Away from This Episode:

• Why perfection often slows progress more than fear or lack of knowledge

• How "good enough" can be a powerful financial strategy, not a compromise

• Practical ways to break through procrastination without burning out

• When delegation and automation actually help and when they just add complexity

• How to balance ambition with contentment without feeling like you're settling

• Why consistency beats intensity in both money and life

Questions Worth Sitting With:

Where are you chasing "perfect" when "done" would be better? What would improve immediately if you lowered the bar just a little? Which money habit could become easier if you stopped optimizing it?

We'd love to hear your take. Share your thoughts in the Spotify comments or bring the conversation into the Basement Facebook group, especially if this episode gave you permission to ease up without giving up.

Sometimes the best financial move isn't pushing harder. It's choosing progress that actually fits your life.

This one's a quiet classic, and those tend to age the best.

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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One snowy Christmas Eve in Texarkana, Neighbor Doug settled into bed in his snazzy Superman Footie PJs (Amazon affiliate link), still buzzing on Joe’s Mom’s eggnog…

Today’s special holiday episode recounts a completely original tale of Doug and the money lessons learned when he’s visited by three ghosts—past, present, and future.

Especially when it comes to past credit mistakes, what’s done is done. Whatever method works best for you (debt snowball or debt avalanche), do that one. Come to terms with your bad money habits and realize that you can’t outearn them. It’s on you to fix the bad money habits of your past. Focus on what’s current and fix what needs fixing today.

Don’t get caught in the trap of lamenting your past nor only planning for the future. Our only truly limited resource is time. Balance living for today with planning for the future. Remain in the present – especially when spending time with your loved ones – while keeping a vision in mind for your longer-term future plans. Be intentional about your plans and actions today and timeline what you want to achieve in what time you have remaining.

Communicate on a regular basis with your “team” (loved ones) about your financial goals, progress, and situation. We recommend scheduling a weekly Family Budget Meeting. Automate as many of your financial decisions as possible today so you never have to think about them again in the future. Commit to paying off that mortgage early, ramp up those retirement savings contributions, stack those Benjamins for your kids’ college savings. Decide where you want to be financially in the future; face reality of where you are currently (we like our sponsor, Monarch Money, to track where you are); and take the necessary step to make that future a near certainty.

Remember that time is the one commodity that’s finite for all of us. Value your time and experiences while staying responsible to your present and future self. Remember and learn from the sins of your past to build on your strengths; focus on living in the present and building your financial foundation; and head into the future with more confidence than Joe’s Mom’s Neighbor Doug during the annual Sun’s Out, Guns Out El Camino Competition at the Sizzler.

FULL SHOW NOTES: https://stackingbenjamins.com/doug-and-the-three-ghosts-2025-holiday-special-1778

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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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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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 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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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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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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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.

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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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