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Financial Feminist

246. How to Reinvent Yourself (Without Losing Yourself) with Sophia Amoruso

Financial Feminist

Her First $100K

Self-improvement, Education, How To, Business

4.7 • 6.2K Ratings

🗓️ 4 August 2025

⏱️ 64 minutes

🧾️ Download transcript

Summary

What happens when you build a $100 million brand, become the face of a cultural movement, and then watch it all come crashing down—publicly? In this episode, I sit down with the iconic Sophia Amoruso—founder of Nasty Gal, originator of #Girlboss, and now a seasoned investor and entrepreneur—to talk about what it really takes to reinvent yourself without losing who you are. We get raw about failure, public scrutiny, and why walking away from something “successful” might actually be the most powerful move you can make. Whether you’re pivoting careers, or simply redefining what success looks like, Sophia’s insights are the masterclass in reinvention you didn’t know you needed. Sophia’s links: Website: https://www.sophiaamoruso.com/  Business Class: https://www.businessclass.co/  Read transcripts, learn more about our guests and sponsors, and get more resources at https://herfirst100k.com/financial-feminist-show-notes/reinventing-yourself-sophia-amoruso/ Looking for accountability, live coaching, and deeper financial education? Check out our exclusive community! Join the $100K Club: https://herfirst100k.com/100k-pod   Our favorite travel and cash-back credit cards, plus other financial resources: https://herfirst100k.com/tools Not sure where to start on your financial journey? Take our FREE money personality quiz! https://herfirst100k.com/quiz Special thanks to our sponsors: Squarespace Go to www.squarespace.com/FFPOD to save 10% off your first website or domain purchase. Indeed Get a $75 sponsored job credit to get your jobs more visibility at Indeed.com/FFPOD. Rocket Money Stop wasting money on things you don’t use. Cancel your unwanted subscriptions by going to RocketMoney.com/FFPOD. Quince For your next trip, treat yourself to the luxe upgrades you deserve from Quince. Go to Quince.com/FFPOD for free shipping on your order and 365-day returns. Netsuite If your revenues are at least in the seven figures, download the free e-book Navigating Global Trade: 3 Insights for Leaders at NetSuite.com/FFPOD. Saily Get an exclusive 15% discount on Saily eSIM data plans! Go to Saily.com/FFPOD download the Saily app and use code 'FFPOD' at checkout. Masterclass Get at least 15% off any annual membership at masterclass.com/FFPOD. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

Imagine building a $100 million brand, writing a bestselling book, and have a Netflix series made about your life, and then burning it all to the ground. If you've been playing small, trying to avoid failure, or disappointing the people in your life, this episode is for you. Because you can get the life you want, but you're going to have to disappoint some people to get it. We're joined today by Sophia Amaruso, founder of Nasty Gal and the original

0:21.2

hashtag Girl Boss. The worst look is saying you're going to do something and not doing it. It's a better

0:25.5

look to do it and fail. She is now a successful investor and entrepreneur with her two businesses,

0:30.7

trust fund and business class. Being yourself gives other people permission to be themselves,

0:35.5

taking like big swings, gives other women the

0:38.4

opportunity to do the same thing. We have a very unfiltered conversation about what success really

0:43.7

looks like, about reinvention and failure, especially after what might feel like your life

0:48.1

completely falling apart. Doing it and blowing is like a way better story than being that person

0:53.0

that just fucking navel gazes.

0:55.0

We talk about the rise and fall of nasty gal, everything she wished she knew about being a good leader,

1:00.0

and how she's found a new form of freedom by doing business her way.

1:03.0

The thing about people knowing your name is it's like less interesting that they know your name.

1:07.0

It's more interesting that there's something to do with your name.

1:10.0

She also gets real about surviving

1:11.4

public scrutiny and also having the very book and so much of her identity kind of be mocked by society.

1:18.8

Not everybody's going to like what you do. And like, I'm not the thing that I wrote in 2013.

1:25.5

But also how to walk away from things, even though they might feel, quote unquote, successful, but not aligned with what you actually want to do. And of course, we talk about Girl Boss. We talk about how it started a decade ago and where it is now. There is one guarantee in life, and it's that you're going to come up against failure time and time again. But it's how you handle it and how you respond that builds your

1:44.4

resiliency and makes you not only a better business owner, but a better person in general. I learned

1:49.0

so much from this episode, even as somebody running my own multi-million dollar business. And I

1:53.5

think if you have been fed this belief about what success should look like and it's always felt

1:58.2

different to you, you're going to feel very, very seen

2:01.5

by this episode. So let's get into it. But first, a word from our sponsors. This episode of

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