Building Wealth Through Every "Era" of Your Life

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

🗓️ 18 April 2025

⏱️ 59 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Some people master reinvention. They move from one stage of life to the next with confidence, purpose, and an eye on long-term success. What if your financial plan could do the same?

In today’s roundtable, Joe is joined by Alyssa Maes, Roger Whitney (The Retirement Answer Man), and OG to talk about what it takes to build wealth that lasts—not just through one season of life, but through all of them.

🎯 Inside the episode:

What starting strong in your 20s and 30s really looks like
How to fight lifestyle creep and sharpen your personal brand mid-career
Why simplifying cash flow in retirement can be a game-changer
The power of habits, automation, and adaptability across all stages
And what consistent, thoughtful choices can do for your long-term success

The thread running through it all? Knowing who you are, where you're going—and letting your financial decisions reflect that.

We also sneak in a bit of trivia involving the most expensive comic book ever sold and a certain pop icon with a track record of breaking records (you can probably guess who).

This episode is about more than music or money—it’s about making every era of your life count.

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

Click on a timestamp to play from that location

0:00.0	Is this your place?
0:01.4	No.
0:01.9	No, no, no, no, no.
0:03.4	No, I live with my mom.
0:04.8	Oh.
0:05.4	Yeah.
0:05.9	You hungry?
0:07.0	Hey, Ma!
0:07.9	Can we get some meat loaf?
0:13.5	Live from the basement of the YouTube headquarters.
0:16.9	It's the Stacking Benjamin Show.
0:19.5	Oh!
0:20.2	No! No! Oh! No! It's the Stacking Benjamin Show.
0:37.4	I'm Joe's mom's neighbor, Doug, and all this week we've been diving into the career of Taylor Swift to help you make better financial and career decisions. Today, let's talk about the sheer
0:39.7	longevity of Swift's reign at the top of the music industry. Like Swift, you want to win through
0:46.1	all of your eras, don't you? What does it take to notch those money victories? We'll answer
0:51.7	that question today. But that's not all, of course.
0:55.2	We'll also share a trivia question to see if we can't narrow the gap in our year-long
1:00.1	challenge.
1:01.0	And now, a guy who when you say challenge, he says, you've got this.
1:06.5	He's never once said that to me.
1:08.3	It's Joe Saul Cahy.
	...

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