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

The Stacking Benjamins Show

Joe Saul-Sehy | Cumulus Podcast Network

Investing, Business, Self-improvement, Education

4.2 • 1.9K Ratings

🗓️ 30 April 2025

⏱️ 64 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! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	I'm making a robot head with an Amazon box.
0:03.0	I've painted it silver and Daddy helped me make it.
0:05.0	At Amazon, we're actually using paper bags for more of our deliveries.
0:08.0	And now I'm making a paper hot air balloon
0:11.0	and I even made a little brown basket
0:13.0	and I'm making a dog that looks just like Monty.
0:16.0	Just one of the ways we've reduced the weight of our packaging by more than 40% since 2015,
0:20.0	which is still good for playtime.
0:22.6	Mom, where's the scissors?
0:25.6	To learn more, visit aboutamason.co.cote.U.K. forward slash sustainability.
0:29.6	The autopilot order. Now, informal.
0:32.6	The strong urge felt at the ordering kiosk or drive-through that takes over the entire body and mind and results
0:38.3	in a person ordering a Big Mac without even having to think. Related phrases, looks like I've
0:43.1	ordered a Big Mac again. The autopilot order at McDonald's.
0:48.0	Serves from 11am, subject to availability. Hey, this is Joe's sister Nikki. 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.
1:08.0	Live from Joe's mom's basement, it's the stacking Benjamin show.
1:17.5	I'm Joe's mom's neighbor, Doug, and what could possibly derail your retirement plans today we'll
1:29.0	present four culprits and how you can protect against them but that's not all are you
1:35.7	thinking about that side hustle you've always wanted to do but don't have the courage to
1:39.9	pull the trigger we have a tic-tock minute that'll hopefully get you moving. And of course,
1:45.3	I'll be sure to give you a heaping helping of my delectable trivia. And now, three guys who are
1:51.1	taking a break from filming the next season of Squirrels Gone Wild, it's Joe, OG, and Len Pappenzo! Hey there, Stackers, and happy Wednesday.
	...

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