Big changes are coming to the tax code—and that could mean big savings if you know where to look. On today’s episode, Joe, OG, and Doug break down the most important updates in the 2025 tax laws and share smart, simple ways to keep more of your hard-earned cash.

Whether you're a spreadsheet-loving tax nerd or someone who still asks, “Wait, do I have to file?”—this episode will help you navigate the new rules like a pro.

Here’s what we unpack:

The 2025 Tax Overhaul: What changed, what stayed the same, and how it affects your bottom line

Credits vs. Deductions: Why that $1 credit might be worth more than a $5 deduction (math, but fun)

Above-the-Line Moves: Claim valuable deductions without itemizing

New Wins for Givers and Drivers: Above-the-line charitable contributions AND (drumroll…) personal auto loan interest is back!

Family Tax Breaks: Expanded dependent care accounts and beefed-up child credits

50 and Thriving: New 401(k) catch-up rules that can help you max out your retirement

Listener Mailbag: JJ asks how to contribute more to his 401(k) after age 50—and we bring the strategies

The TikTok Minute: Because money wisdom can live on the internet too

Doug’s Trivia & Financial Shenanigans™: Of course

You’ll walk away with clear, practical takeaways that could add thousands to your bottom line—without needing to read the tax code (you're welcome).

FULL SHOW NOTES: https://stackingbenjamins.com/upcoming-tax-changes-1714

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 the scariest part of retirement isn’t running out of money—but losing your sense of identity? This week on The Stacking Benjamins Show, we tackle the fears that hold so many people back from financial independence and a joyful, purpose-filled retirement.

Joe Saul-Sehy and Doug are joined by an all-star panel of financial thinkers:

Mark Trautman (Mark’s Money Mind)

Paula Pant (Afford Anything)

Jesse Cramer (Personal Finance for Long-Term Investors)

Together, they unpack the emotional, practical, and strategic side of planning your next chapter—whether you're closing in on retirement or still working toward it.

The biggest fears about retirement: from running out of money to running out of meaning.

The “one more year” syndrome: why it's so tempting to delay and how to break through.

Time freedom vs. financial freedom: how to align your life goals with your money strategy.

Tactics to conquer fear: income layering, diversified portfolios, annuities, and rental properties.

Psychology matters: why no spreadsheet ever solved a midlife identity crisis.

Real stories from the panel: wins, struggles, and lessons from guiding others through retirement transitions.

Planning for healthcare and long-term care: because your body didn’t get the early retirement memo.

Plus, the usual basement mayhem: trivia, playful host banter, and a few unexpected laughs (we won’t call them “funny”—you know the rule).

Mark’s Money Mind podcast

Afford Anything podcast

Personal Finance for Long-Term Investors

AARP: Retirement Readiness & Addressing Fear

Blog post: “Fear Will Hold You Prisoner. A Diversified Portfolio Will Set You Free.”

Retire to something, not just from something. Purpose beats spreadsheets.

Understand your income plan. Know where the money will come from, rain or shine.

Plan for healthcare now, not later. Medicare, long-term care, and medical surprises deserve your attention.

Don’t go it alone. The best plans are ones you understand, but it helps to get advice from trusted sources.

Whether you’re on the cusp of calling it quits or still deep in the grind, this episode will help you prepare—not just financially, but mentally and emotionally—for a retirement you’ll love.

FULL SHOW NOTES: https://stackingbenjamins.com/what-is-holding-you-back-from-reaching-your-goals-1713

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

🎧 Dive deeper, grab resources, and check out past episodes at StackingBenjamins.com

Enjoy!

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What do your financial priorities look like when you're just getting started... or when you're sitting on $100 million? If you’re still stuck trying to figure out how to max out your Roth IRA and also afford dinner, this episode’s going to walk you through what might be coming next—without promising you a yacht by Tuesday.

This week on The Stacking Benjamins Show, Joe Saul-Sehy, O.G., and Doc G (Jordan Grumet) are joined by Nick Maggiulli, Chief Operating Officer at Ritholtz Wealth Management and author of Of Dollars and Data, to talk about lessons from his new book: The Wealth Ladder. Nick breaks down the six wealth levels, from scraping together your first emergency fund to navigating the complexities of generational wealth.

They explore:

Why increasing your income early on trumps frugality (sorry, coupon clippers).

What “wealth plateaus” really look like, and how to recognize when your strategy needs to evolve.

The hidden trap of goal obsession, featuring a cameo from world #1 golfer Scottie Scheffler.

The true cost of career choices, and why opportunity cost might be the silent killer of long-term growth.

Why content and code are two of the most powerful wealth-building levers available (especially when they scale without needing a lunch break).

Whether you're stuck in Level 1 or fantasizing about Level 6, this episode has practical, perspective-shifting advice on building wealth—and more importantly, how to enjoy the process without losing your sense of purpose along the way.

Stackers don’t just want to make money—they want to master it without letting it become their master. This conversation bridges income, investing, identity, and intention in a way that gives you both clarity and confidence.

You might even stop worrying about skipping that $5 latte… or realize it’s time to start coding that app you keep talking about at parties.

FULL SHOW NOTES: https://stackingbenjamins.com/invest-differently-and-move-faster-1712

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’s the right financial move for you… right now? If you've ever found yourself reading advice meant for a millionaire when you're still trying to crack five figures—or following budgeting tips when your net worth is seven digits—this episode is your custom-tailored financial GPS.

In this installment of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Doug take you rung-by-rung through the wealth ladder—from humble beginnings at $10K all the way to $10 million—and explain how your financial priorities, risks, and strategies evolve as your net worth grows.

As always, the team weaves in laughter, sarcasm, and that unmistakable basement charm—complete with Doug’s new mug, a calendar confusion history lesson, and a household disaster caused by what can only be described as “revenge rain.”

Why You’ll Love This Episode:
If you’re trying to level up without falling prey to the one-size-fits-all advice machine, this episode delivers a realistic blueprint. It’s equal parts roadmap and reminder: where you are right now matters more than where someone else thinks you should be.

Stacker takeaway? Clarity beats comparison. Especially when it comes to money.

FULL SHOW NOTES: https://stackingbenjamins.com/build-your-wealth-ladder-1711

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 you're working hard but getting nowhere? You're not alone—and you might be stuck in a productivity trap, not a purpose-driven plan. In this episode of The Stacking Benjamins Show, we tackle the big one: how to avoid wasting your life. (No pressure.)

Joe Saul-Sehy kicks things off with a tongue-in-cheek nod to all the ways we fritter away time—before pivoting into a power-packed conversation on building meaningful goals and avoiding common life derailers.

He’s joined by two all-star minds in money and behavior:

Paula Pant from Afford Anything, who reminds us that "you can afford anything—but not everything," and

Jordan Grumet from Earn & Invest, who offers the life-and-death perspective (literally—he’s a hospice doctor) on why we need to act now, not later.

Together with OG and Doug, the roundtable unpacks six common ways people unknowingly waste their lives, including:

Being "busy" instead of effective

Letting fear of failure hijack your plans

Overthinking every move

Paralysis from too many choices

Constant hustle with no progress

Indecision dressed up as careful planning

You’ll hear hard-earned lessons, subtle mindset shifts, and tips for creating financial and personal momentum. Plus:

The surprising link between indecision and regret, backed by Dr. Ellen Langer’s research

Smart strategies for eliminating distractions and taking better action

The difference between motion and movement—especially when it comes to your goals and your money

And, of course, we sprinkle in some classic basement banter, a rowdy trivia throwdown, and Joe’s favorite kind of weekend preview (the kind where no one actually follows their own advice).

Why this episode is worth your time:

🎯 You’ll walk away with:

A clearer idea of what’s holding you back

Practical ways to structure smarter financial goals

Permission to stop doing all the things and start doing the right things

FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-waste-your-time-on-stupid-stuff-1710/

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Want to crush your goals and avoid getting crushed by long-term care costs? In today’s episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG are joined by Retired Lieutenant Commander Gary McDermott, a former U.S. Navy officer turned business coach, who brings military-grade discipline to the world of goal-setting and financial success.

Whether you’re working toward a promotion, launching a side hustle, or just trying to stay on track past February, Gary shares a field-tested, civilian-approved approach to achieving your biggest financial and personal milestones. From defining SMART goals to building sustainable habits and multiple income streams, this conversation is all about real results—no fluff, no buzzwords.

But that’s just the first mission. In the second half, Joe and OG dive into one of retirement’s trickiest topics: long-term care insurance. Is it worth it? When should you buy it? How do you know if it’s right for your situation? Consider this your tactical briefing before walking into a battle you didn’t know you were fighting.

You’ll also hear:

Why borrowing someone else’s goals is a recipe for burnout.

The power of structure and accountability (no drill sergeant required).

What “Trump Accounts” are and why you might want to know about them.

How to evaluate long-term care coverage before it sneaks up on your plan.

Joe’s high-speed review of the new Formula One movie (spoiler: he’s not drafting behind the popcorn).

Packed with tactical advice, unexpected laughs, and practical strategies, this episode delivers a full-stack toolkit for Adventurers looking to thrive—financially and personally—in the second half of 2025 and beyond.

FULL SHOW NOTES: https://stackingbenjamins.com/how-to-set-and-achieve-your-goals-gary-macdermid-1709

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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Still on track to crush your 2025 goals? Or has the year felt more like a Super Mario Kart banana peel moment?

In this special mid-year review episode of The Stacking Benjamins Show, Joe Saul-Sehy and OG take a pause from the summer sprint to look back at the most impactful lessons, conversations, and themes from the first half of 2025. Whether you’re rethinking your budget, fine-tuning your risk tolerance, or just trying to remember where you wrote down your resolutions, this is your nudge to hit the financial reset button—with style.

From Alex Hormozi’s take on embracing risk and skill-building to JL Collins' wisdom on why buying happiness with money is a flawed formula, this episode pulls powerful insights from our brightest guests so far. We revisit career advice from media powerhouse Bonnie Hammer, dig into intentional spending habits, and reflect on the subtle connection between mindset and long-term success.

Oh—and don’t miss a moment of Joe and OG’s always-wise, occasionally-weird banter as they break down topics like:

If you’ve felt a little off-course—or just want a chance to recalibrate without the guilt trip—this episode delivers practical steps and encouraging reminders to help you make the second half of 2025 your strongest yet.

Got goals? Let’s reset ‘em. And if not, we’ve got a few ideas for those, too.

FULL SHOW NOTES: https://stackingbenjamins.com/our-review-of-first-half-2025-1708

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 house full of stuff you thought you needed… but haven’t touched since the Obama administration? In this game show-style episode, we're helping you clean house and bulk up your bank account at the same time.

Joining Joe in the basement are Paula Pant from Afford Anything, OG, and the man, the myth, the TikTok-famous legend’s grandpa’s best friend: Len Penzo (or as Doug calls him, “America’s Most Unexpected Influencer”). Together, they go head-to-head in a raucous showdown, each offering hot takes on everyday items you should stop buying if you want to save money and ditch the clutter.

We dig into:

Why some exercise equipment becomes expensive coat racks

The hidden costs of seasonal decorations

Periodicals, subscriptions, and other budget vampires

And a few “who knew?” items that quietly drain your cash

You'll also get a dose of trivia, debates about Google's "search decay," and a few personal stories that might sound a little too familiar.

Whether you’re decluttering your budget or just here for the basement chaos, this episode is full of laughs, lightbulb moments, and ideas to help streamline your spending.

FULL SHOW NOTES: https://stackingbenjamins.com/decluttering-your-financial-life-greatest-hits-1707

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 your money could bring you more joy—and less stress? Today, we welcome Ken Honda, Japan’s bestselling personal development guru, to the basement. He introduces us to his concept of “Happy Money,” where gratitude replaces fear, and your relationship with money becomes… well, happier. From early lessons in emotional finance to wisdom from his own mentors, Ken shares how small mindset shifts can lead to big life changes.

But before we get zen with our Benjamins, Joe and OG shine a light on the latest investigation into real estate commissions. Are hidden fees quietly draining your wallet when you buy or sell a home? The Justice Department seems to think so. We dive into what’s happening—and what you can do about it.

Also in the episode:

HSA contribution limits are rising—are you using your health savings account the smart way?

A listener wonders if hiring their kids can unlock Roth IRA opportunities (spoiler: it’s not as simple as “just write them a check”).

Doug moonshines a trivia question that may or may not involve death (but definitely involves Doug).

Whether you’re looking for practical strategies or a new perspective on money itself, this episode brings both insight and inspiration.

FULL SHOW NOTES: https://stackingbenjamins.com/happiness-with-ken-honda-greatest-hits-1706

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 home packed with emotional baggage... and maybe a few fondue sets you haven’t touched since 2003? Organizational expert Tracy McCubbin joins us to talk about the emotional side of clutter—why it builds up, how it weighs us down, and what to do when your sentimental stuff is quietly running the show.

Meanwhile, Joe and OG dig into another kind of mess: the billions retirees lose by claiming Social Security too early. Timing isn’t just everything—it’s the difference between thriving in retirement and wondering where all the money went.

In this episode, we cover:

Plus: a listener question, some truly questionable fashion choices, and one more reason not to hoard your retirement benefits—or your holiday dishes.

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