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The Stacking Benjamins Show

5 Steps to Your Best Retirement (with Jeremy Keil, CFP) SB1742

The Stacking Benjamins Show

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

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

4.42K Ratings

🗓️ 1 October 2025

⏱️ 65 minutes

🧾️ Download transcript

Summary

Think your retirement plan is bulletproof? Think again. In this eye-opening episode of The Stacking Benjamins Show, Joe Saul-Sehy, OG, and Neighbor Doug are joined by certified financial planner Jeremy Keil, CFP® to walk you through the steps to building a retirement plan that won’t crack under pressure. From mapping out your spending before you ever leave the workforce to crafting a tax strategy that keeps more money in your pocket, this conversation is your blueprint for making your golden years actually golden.

But just when you think you’ve got retirement handled, we throw a curveball: private equity. With giants like Goldman Sachs and T. Rowe Price trying to slip these complex investments into your 401(k), it’s time to ask whether “more opportunity” is really a good thing — or a trap for the unprepared. Joe and OG break down the risks, the realities, and what you need to know before you sign on the dotted line.

As always, we serve it all with a side of basement banter — from Doug’s trivia about the first issue of Playboy to a TikTok football moment you didn’t know you needed — plus real-life stories that prove retirement planning is as much about mindset as it is about math.


What You'll Learn In Today's Show:

  • The five key steps to building a retirement plan that works for you, not just a generic spreadsheet.

  • Why starting with your spending habits (not investments) can make or break your retirement success.

  • How to prepare for the emotional side of retirement — including those pesky “what now?” questions.

  • The surprising risks of private equity creeping into your 401(k) — and how to decide if it’s worth it.

  • Smart tax strategies to make your retirement money last longer.

  • How long-term care, market volatility, and unexpected expenses should factor into your plan.


    Questions to Ponder During the Episode (and discuss with other Stackers!)


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Transcript

Click on a timestamp to play from that location

0:00.0

What a filthy job. Could be worse. How? Could be raining.

0:05.7

Bhrush.

0:07.0

Live from Joe's Mom's Basement, it's the Stacking Benjamin's show.

0:30.3

I'm Joe's mom's neighbor, Doug, and how's your retirement plan coming along?

0:34.6

Looking for a succinct step-by-step approach, we'll outline five steps to a better plan on

0:40.1

today's show featuring CFP Jeremy Kyle.

0:44.1

And in our headline segment, as Mom says, the future is now.

0:48.7

Money management is a changing as T-Rope Bryce and Goldman Sox join forces to market.

0:55.4

Goldman Sox.

0:56.5

I heard that too.

0:57.7

Goldman has some socks.

0:59.4

Why did I?

1:00.1

I said the word.

1:01.4

I keep on moving on with the rest of the sentence.

1:03.3

And in my head, I'm hearing myself say, why did you say socks?

1:06.7

It's not socks.

1:08.1

O.G.'s going to say, why did you say socks?

1:10.1

Well, keep bringing it, man. Let's go. Okay. I'm going to back up and say, and Goldman Sachs join forces to market more investments to you. But are these in your best interest? We'll share. And speaking of share, I'll also share a talk talk minute. And then I'll share some incredible money themed trivia.

1:28.8

I'm killing it today, aren't I?

1:30.3

And now two guys who still owe me for the last round ice cream plus interest.

1:35.5

It's Joe and oh, Jujujuj, Jee.

1:40.8

Hey there, Stackers.

...

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