Sep 16, 2026 · 25 min · 12 segments
Why do so many capable women believe they're "bad with money"? Jessica Brady, a financial adviser who built and sold her own firm, and Caitlin Judd, entrepreneur and business coach, join us from…
Caitlin JuddGuest
Brooke RobertsHost
jess let's start with you you're a former financial advisor a business owner a money educator and now an author what prompted you to write this book
What I hear a lot from people is, oh, I'm just bad with money or investing is too scary or I don't know where to start.
And what I need people to remember is if you've never actually learned anything about this, it is really unfair to label yourself as quote unquote bad with something because you've never done it before.
And so I think that that's the big thing that I want people to know is you can change your belief system.

And Caitlin, you're an entrepreneur, you've founded an entrepreneurial community, you're a business coach, and now you're an author as well.

Yeah, the good girl effect is a result of the systems and the institutions that we grow up in and how they influence us to stay good, to be good, in order to feel safe, to feel loved, to feel welcome and that therefore impacts how we show up in the world and it can hold us back and it can permeate all different domains of our lives from love to health, business, finances.

So I wrote a book that was all about how to untangle from that good girl, how to learn the scripts that you've perhaps inherited when you were young and then how to reclaim your power and your agency to rebuild or build a life that you love off the back of the fabulous person that you already are.

You know, Caitlin, you've actually, you know, you've had quite a portfolio career.

Can you tell us a bit about, you know, what that means for you and how that shows up?

I have a background in marketing and business and I went out at the age of 25, which I think is quite young, very naive, didn't know what to expect.

And I think that, you know, starting a business and working for yourself is the greatest lesson in who you are.

jess let's start with you you're a former financial advisor a business owner a money educator and now an author what prompted you to write this book
What I hear a lot from people is, oh, I'm just bad with money or investing is too scary or I don't know where to start.
And what I need people to remember is if you've never actually learned anything about this, it is really unfair to label yourself as quote unquote bad with something because you've never done it before.
And so I think that that's the big thing that I want people to know is you can change your belief system.

And Caitlin, you're an entrepreneur, you've founded an entrepreneurial community, you're a business coach, and now you're an author as well.

Yeah, the good girl effect is a result of the systems and the institutions that we grow up in and how they influence us to stay good, to be good, in order to feel safe, to feel loved, to feel welcome and that therefore impacts how we show up in the world and it can hold us back and it can permeate all different domains of our lives from love to health, business, finances.

So I wrote a book that was all about how to untangle from that good girl, how to learn the scripts that you've perhaps inherited when you were young and then how to reclaim your power and your agency to rebuild or build a life that you love off the back of the fabulous person that you already are.

You know, Caitlin, you've actually, you know, you've had quite a portfolio career.

Can you tell us a bit about, you know, what that means for you and how that shows up?

I have a background in marketing and business and I went out at the age of 25, which I think is quite young, very naive, didn't know what to expect.

And I think that, you know, starting a business and working for yourself is the greatest lesson in who you are.
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