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The Stacking Benjamins Show

Create Goals that Stick (with Ret. Lt. Cdr. Gary MacDermid)

The Stacking Benjamins Show

Joe Saul-Sehy | Cumulus Podcast Network

Investing, Business, Self-improvement, Education

4.2 • 1.9K Ratings

🗓️ 16 July 2025

⏱️ 81 minutes

🧾️ Download transcript

Summary

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

Transcript

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0:00.0

This episode is brought to you by Navy Federal Credit Union. Navy Federal can help you find

0:03.9

and finance the right vehicle with ease. With Navy Federal's car buying service, powered by True

0:08.9

car, you can find the vehicle that's right for you as you search through inventory and compare

0:13.8

models. And you could get an amazing rate when you finance with Navy Federal. Visit

0:18.9

NavyFederal.org slash Truecar to learn more.

0:22.5

Navy Federal Credit Union, our members, are the mission.

0:25.9

Navy Federal is insured by NCUA, credit and collateral subject to approval.

0:30.2

Small business owners, State Farm's there with small business insurance to fit your specific

0:35.9

needs.

0:36.8

Whether you're starting a new venture or growing an existing one, State Farm helps you choose

0:41.3

the right coverage to protect what matters most.

0:44.3

Working with a local State Farm agent helps you understand your coverage options, offering

0:48.3

local support to help you achieve your goals.

0:51.0

Focus on turning your passion into a thriving business knowing your insurance can change

0:55.9

as your business grows. Stay Farm, here to help you succeed with your business. Like a good neighbor,

1:02.1

stay farm is there. Bring out you dead. Bring out your dead. There's one. I'm not dead.

1:11.6

What?

1:12.6

Nothing.

1:13.6

He has your nine puts.

1:14.6

I'm not dead.

1:15.6

Here.

1:16.6

He says he's not dead?

...

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