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The Stacking Benjamins Show

Becoming a Financial Badass with Jen Sincero (SB1678)

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

🗓️ 5 May 2025

⏱️ 47 minutes

🧾️ Download transcript

Summary

Joe Saul-Sehy sits down with bestselling author Jen Sincero, the powerhouse behind You Are a Badass and You Are a Badass at Making Money. If you've ever felt stuck in financial quicksand or caught in a loop of scarcity thinking, Jen brings the fire (and the funny) to help shift your mindset and start building wealth from the inside out.

You’ll hear:

  • How Jen went from living in a garage to becoming a seven-figure entrepreneur

  • The mindset shifts that changed her relationship with money—and could change yours

  • Why self-talk and affirmations aren't fluff—they're your financial launchpad

  • Simple ways to start reprogramming how you think, spend, and save

  • The importance of consistent investing—even when you’re not feeling confident

We also touch on:

  • Why your HSA might be a secret investing weapon

  • What to know as tax deadlines approach (and how not to panic)

  • A listener’s creative approach to investing—and how OG and Joe weigh in

  • Plus: marathon filming, TV mishaps, and trivia surprises from Mom’s neighbor Doug

If you're ready to stop playing small with your money and start stacking like a badass, this episode will give you the mindset—and motivation—to get going.


FULL SHOW NOTES: https://stackingbenjamins.com/you-are-a-badass-at-making-money-greatest-hits-week-1678

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

Hey, stackers. Happy Monday. We have a fantastic Monday guest, Jen Cicero. And if you have not heard

0:07.0

Jen Cicero before, she had a huge book called You Are a Badass, and then you are a badass with

0:13.5

and Jen Cicero today is going to help you be a badass with money. She's just another in a great

0:19.7

line of guests that we've had on the

0:22.0

Stacking Benjamin Show. I'm super happy. Jen's been on a couple times. Of course, this year has

0:27.1

been phenomenal. We did two episodes around earning more money to begin the year. We had Jen

0:36.1

and Jill from frugal friends on then to lock down your budget, right? Make more

0:40.6

money. Lock down your expenses. And we just spent a few weeks talking about having more drive

0:48.2

with Molly Fletcher and then how not to invest with financial planner extraordinaire Barry Riddholtz. And then how not to invest with financial planner extraordinaire Barry Riddholtz.

0:57.5

And then we went into career mode where we took more of a macro view,

1:03.5

exploring the career of Taylor Swift and doing a case study.

1:08.6

And then the next week, getting very tactical with the amazing coach, Loretta K. Lee.

1:13.3

Well, this next eight weeks, we are going to begin pivoting more toward investing.

1:19.8

If there's a theme for the next eight weeks, it's going to be investing in your portfolio.

1:24.1

We're going to take a week and talk about international investing. We're going to take a week and talk about international investing.

1:27.8

We're going to take a week and talk about your spend-down plan.

1:32.0

And whether you're 25 or 55 or 75, you want to know what your spend-down plan is going to be.

1:38.8

They call it decumulation plan.

1:41.7

But we're going to, of course, mix it up with some other fun stuff. We're going to talk about

1:45.2

good eating. We'll also talk to the amazing Robert Niles from the Park Insider, who always helps

1:51.1

us kick off summer. So that begins today with this mindset shift with Jensen. Chiro. We're going to

1:58.3

start with investing mindset next week. This is our

...

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