Retirement Roadblocks & Resilient Planning: The Squirrels Gone Wild Edition (SB1676)

The Stacking Benjamins Show

Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP

Business, Financial Planning, Cfp, Education, Personal Finance, Retirement, Investing, Money

4.4 • 2K Ratings

🗓️ 30 April 2025

⏱️ 63 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Retirement might be the goal, but the journey? Full of curveballs. On today’s episode, Joe Saul-Sehy is joined by special guest co-host Len Penzo of LenPenzo.com, along with OG and Neighbor Doug, for a no-holds-barred look at what really derails retirement plans—and how to build a strategy that can handle the chaos.

From unexpected job loss to rising long-term care costs, adult kids moving back home, and even changing relationship dynamics, this episode dives into the often-overlooked risks that can chip away at your retirement dreams.

Inside the episode:

What to consider when evaluating long-term care insurance
How job instability late in your career can throw off your timeline
The growing trend of adult children impacting their parents’ retirement
Grandparents becoming full-time caregivers—and the financial toll that brings
Relationship shifts and widowhood in retirement
Downsizing, austerity planning, and staying financially flexible

Plus, our TikTok Minute features Gary V on why taking a step backward might be the smartest move forward. And as always, Doug brings the trivia heat—this time, with a nostalgic nod to a certain potato-headed toy.

With Len Penzo in the basement, the insights (and squirrel references) are extra sharp. Prepare to laugh, learn, and rethink what “retirement ready” really means.

FULL SHOW NOTES: https://stackingbenjamins.com/four-things-that-can-derail-your-retirement-plan-1676

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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Transcript

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0:00.0	Hey, this is Joe's sister Nikki.
0:03.1	I think I might be the only girl in the world who has a brother who spends his entire day in the basement, pretending he has an internet radio show.
0:17.8	Live from Joe's mom's basement, it's the stacking Benjamin show.
0:27.4	I'm Joe's mom's neighbor, Doug, and what could possibly derail your retirement plans? Today, we'll present
0:39.3	four culprits and how you can protect against them. But that's not all. Are you thinking
0:45.9	about that side hustle you've always wanted to do, but don't have the courage to pull the trigger?
0:50.7	We have a TikTok minute that'll hopefully get you moving.
0:56.1	And of course, I'll be sure to give you a heaping helping of my
0:57.7	delectable trivia. And now
0:59.9	three guys who are taking a break from
1:01.8	filming the next season of Squirrels Gone Wild,
1:04.6	it's Joe, OG, and Len
1:07.2	Pappenzo.
1:18.6	Music And Len Pappenzo! Pappenzo! Hey there, Stackers, and happy Wednesday. You're right.
1:19.6	It was, we were just getting to the part where, I don't know, what are we calling them,
1:23.6	Len, Squirrel A and Squirrel B.
1:25.6	Squirrel A is having a, really a conipion, his mom calls it. Yeah, and Squirrel B is about doing the same thing. So you should see Squirrel C. Just wait to see Squirrel C. When Squirrel C see Squirrel A and B together, I can't, well, that's going to be. Did you get them to sign the releases this time? Get them into the back of the RV and get them to sign the releases before you're filming them. You should see the contract language, Dag. They sign anything. People are brand new to the show going, what the hell? Is this a money show? Welcome back to Stacky Benjamin, sit back and relax because we've got an hour of fun and, man, some super helpful conversation today.
2:03.2	If you've ever dreamt about retirement, what could make it go the wrong way?
2:07.2	Well, one guy is going to make sure it goes the right way.
2:09.7	He's also here today.
2:10.7	Mr. O.G. is here.
2:11.8	Tear yourself away from squirrels gone wild, man.
	...

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