Create Goals that Stick (with Ret. Lt. Cdr. Gary MacDermid)
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.
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1:21:29
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1:21:29
Mid-Year Financial Reset: Key Takeaways from the First Half of 2025 (SB1708)
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:
Why goal setting isn’t just for January—and how to mid-course correct before December sneaks up on you.
Risk management in real life (not the textbook version).
Why mindful consumption isn’t about cutting back, but tuning in.
What makes retirement joyful beyond the spreadsheets.
How your community can be the most underrated part of your portfolio.
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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1:20:48
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1:20:48
The Stuff You Should Stop Buying (and Why Your Wallet Will Thank You) SB1707
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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1:05:06
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1:05:06
Happy Money, Hidden Fees, and Hiring Your Kids (SB1706)
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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1:17:15
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1:17:15
Want More Money? Cut The Clutter (with Tracy McCubbin) SB1705
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:
Why sentimental clutter is more than just "stuff"—and how to finally let it go.
How donating intentionally can breathe new life into your old things (and clear some mental space).
The tough conversations adult kids need to have with parents about downsizing and letting go.
Strategies to help you avoid making costly Social Security decisions.
A surprisingly thoughtful take on the Taco Bell Hotel (yes, it’s real... and yes, it sold out in minutes).
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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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.
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