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.
Key takeaways:
Reinvention requires letting go of external definitions of success
Sophia shares that walking away from her company—after a decade, a best-selling book, and a Netflix series—wasn’t failure, but freedom. She emphasizes that your identity isn’t what you build, what others think of you, or what you accomplish. Reinvention is about shedding the labels and choosing what aligns now—not just what made sense in the past.
Failure isn’t the opposite of success—it’s part of the process
Sophia’s public setbacks didn’t define her—they became the foundation of her next chapter. She argues it’s a better look to do something and fail than to sit on the sidelines overanalyzing. Her story shows that reinvention often begins with a fall—and the courage to keep going.
Redefining ambition means recalibrating what you want and what you’re willing to sacrifice
Both Sophia and I reflect on how our ideas of success have changed. Bigger isn’t always better. If you’re chasing press coverage, funding rounds, or “scalable growth,” ask yourself if you actually want what comes with it—or if you’re just following a script.
You don’t have to build something massive to build something meaningful
Sophia is now thriving with zero full-time employees and a business that allows her to travel, create, and rest on her terms. She warns against glamorizing large teams or fundraising and encourages entrepreneurs to think smaller—but smarter.
Survival mode is temporary—and sometimes, the hard seasons are what shape you most
For anyone stuck in scarcity or failure, Sophia offers perspective: how you feel now isn’t how you’ll feel forever. Every stage—whether it’s a pivot, a pause, or a breakdown—has the potential to become a turning point.
You don’t need to be perfect to be powerful
Sophia urges entrepreneurs to stop wasting time chasing perfection. Put the thing out there. Start messy. Done is better than perfect—and often, the real impact comes from being relatable, not polished.
Notable quotes
“Doing it and blowing it is a way better story than being that person that just fucking navel gazes.”
“If you do what you don’t want to do, you’re suffering. If your goals are in line with your ambition, then nobody suffers.”
“The worst look is saying you’re going to do something and not doing it. It’s a better look to do it and fail.”
Episode-at-a-glance
≫ 02:20 – Sophia on setbacks, reinvention, and learning from failure
≫ 08:03 – The Nasty Gal origin story and lessons from scrappy beginnings
≫ 13:22 – Raising $50M: why Sophia took VC money and what she learned
≫ 18:26 – Leadership, accountability, and trusting your team
≫ 25:50 – Letting go: selling the company and self-preservation
≫ 29:04 – Redefining success: bigger isn’t always better
≫ 30:50 – The “Girl Boss” movement: impact, backlash, and legacy
≫ 33:00 – Double standards for women in business
≫ 35:00 – Advice for women founders pitching VCs
Sophia’s Links:
Website: https://www.sophiaamoruso.com/
Business Class: https://www.businessclass.co/
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Meet Sophia
Sophia Amoruso is the Founder & Managing Partner at Trust Fund, an early-stage venture fund focused on pre-seed and seed stage investments. Sophia made her mark in 2006 as the founder of fashion e-commerce phenomenon Nasty Gal, which she built to over $100 million in revenue. Sophia is also the author of #GIRLBOSS, which spent 18 weeks on the New York Times Bestseller List, sold 500,000 copies, and was adapted into a Netflix series produced by Charlize Theron. Sophia has been featured on Forbes America’s Richest Self-Made Women issue as well as the Forbes 30 Under 30 list, Fortune 40 under 40, and Fast Company’s Most Creative People in Business.
Transcript:
Tori Dunlap:
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 Amoruso, founder of Nasty Gal and the original #Girlboss.
Sophia Amoruso:
The worst look is saying you’re going to do something and not doing it. It’s a better look to do it and fail.
Tori Dunlap:
She is now a successful investor and entrepreneur with her two businesses, Trust Fund and Business Class.
Sophia Amoruso:
Being yourself gives other people permission to be themselves, taking big swings gives other women the opportunity to do the same thing.
Tori Dunlap:
We have a very unfiltered conversation about what success really looks like, about reinvention and failure especially after what might feel like your life completely falling apart.
Sophia Amoruso:
Doing it and blowing it is a way better story than being that person that just fucking navel gazes.
Tori Dunlap:
We talk about the rise and fall of Nasty Gal, everything she wished she knew about being a good leader and how she’s found a new form of freedom by doing business her way.
Sophia Amoruso:
The thing about people knowing your name is it’s less interesting that they know your name, it’s more interesting that there’s something to do with your name.
Tori Dunlap:
She also gets real about surviving public scrutiny and also having the very book and so much of her identity being mocked by society.
Sophia Amoruso:
Not everybody’s going to like what you do and I am not the thing that I wrote in 2013.
Tori Dunlap:
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 Girlboss, we talk about how it started a decade ago and where it’s 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 resiliency and makes you, not only a better business owner, but a better person in general. I learned so much from this episode even as somebody running my own multi-million dollar business and I think, if you have been fed this belief about what success should look like and it’s always felt different to you, you’re going to feel very, very seen by this episode so let’s get into it. But first, a word from our sponsors.
So, Sophia, you made an Instagram post where you took stock of your life and I love how you ended it. You said 40-year-old Sophia is financially free and shocked she pulled any of it off, navigate setbacks with grace and is, quote, proof that you can shoot for the moon, land in the stars, fall back to Earth and be more free, inspired, wiser, happier and hotter than ever. Do you have a falling-back-to-earth moment that you’re most grateful for in hindsight?
Sophia Amoruso:
I think it was when everything shit the fan in late 2016 and it was Nasty Gal fell apart the day Trump was elected and Hillary lost and then this Netflix series came out about my life. This alone is a whole podcast or, I don’t know what, documentary or something. But four months later, this Netflix series came out about my life and I think the hardest part of it all, there’s a lot of hard things that happened this year, I had husband that left me earlier in 2016 was when the series came out and there were headlines like the worst thing about Netflix’s Girlboss was its source material. And I think it was then that I just really realized that my identity isn’t tied to what I do, what I do is not who I am and what other people think I am is not who I am.
Obviously, it matters, I care about what people say when I leave a room, I want them to say nice things but I think the biggest thing I took away from that was probably ended what I do … What I do or haven’t done or what I’ve won and lost or what I have isn’t who I am and that what I get to take with me is what I’ve learned and the rest of it doesn’t really matter.
Tori Dunlap:
Well, what a way to start an interview. When we talk about that theme a lot on the show which is, I think, women are … We define ourselves by our own accomplishments and our identity becomes what our output is or how much we’re able to do and we feel like we have to earn rest, we feel like we have to earn love, we feel like we have to earn respect. And it sounds like, through, unfortunately, a very public, multiple public instances of this, you came to the point where you’re like, “I am okay just being who I am without having to accomplish anything to earn respect or love or glory or whatever that looks like.”
Sophia Amoruso:
Yeah, I think so. If anything, it would be easier to accomplish less. I feel like it’s easier to be loved when you’re a trad wife or something but-
Tori Dunlap:
Well, no, I think that’s actually-
Sophia Amoruso:
Oh, my God. Do you guys talk about trad wife stuff on this podcast?
Tori Dunlap:
We do. We do, unfortunately.
Sophia Amoruso:
Oh, my God, that’s a whole nother … I don’t want to devolve the conversation in the first five minutes into that, I’m so curious.
Tori Dunlap:
No, but it is a good point where I think that is the fear for women and, unfortunately, that is something that I think you have unfortunately been, dare I say plague, the poster child of which is, when you put yourself out there, when you have the audacity to sell a multi, multi, multi-million dollar company, when you have the audacity to get a Netflix series made about the memoir that you wrote, all of these things are very public. And I think one of the things women are scared of is, if I do put myself out there, if I do dare to want more, somebody somewhere will try to take it from me or society doesn’t like women who are successful. So, what was your experience with that? Because you’re 100% right, if you played it safer, one, probably maybe not everybody would know your name but, at the same time, not everybody would know your name.
Sophia Amoruso:
Mm-hmm, yeah. I think the thing about people knowing your name is it’s less interesting that they know your name, it’s more interesting that there’s something to do with your name and what you’ve done. I think the runoff of what I’ve done matters more to other people than it does to me and that’s a really special thing. And so, I think being yourself gives other people permission to be themselves, taking big swings gives other women the opportunity to, the space and also the confidence to do the same thing. And when you fuck up, honestly, they keep following you because they’re like, “Oh, my God, I fucked up too.” It’s no matter what, if I up on stage at a conference, they’re like, “You’re so relatable,” and I’m just like, “I just want to do a good job.”
And so, it’s no matter … I think what you do as yourself, other people are looking out at you and being like, “Oh, actually, that’s relatable,” and we’re really hard on ourselves. And at the end of the day, I think, if you do make big moves, you will be scrutinized and that sometimes feels louder than what it is that other people have learned from your experience but the thing that people will remember and the thing that changes people’s lives is in your DMs, it’s in my DMs and it happened … Wrote that book in 2013, came out in 2014 and it’s the long tail effect of doing something that inspires people, it’s worth every minute of it.
Tori Dunlap:
Yeah. Well, and I’d love to go back to the beginning for people who might not be familiar with the origin story. So, you had a very non-traditional path. Hitchhiking, selling a stolen book to build a fashion empire. What were those scrappy early years teaching you about business that no MBA could?
Sophia Amoruso:
Yeah. Well, I think, MBA, you learn from listening and maybe some case studies and maybe going out and interning but it’s really different when it’s your business. And it’s really different when it’s your business and you can’t afford an NBA. There have been many times I wish I had an MBA, I certainly think that, if you don’t have an MBA, it would be helpful to work for someone else even if they’re a bad leader to be like, “Oh, this is what it’s like to work for someone else.” I had worked in shoe stores, I knew what management was but I didn’t know what leadership was and then I had to be one and that was really hard. When you are doing all of the jobs, you are able to hold people accountable to doing all the jobs, whereas, it’s just a little more theoretical when you’re an MBA. That being said, there are a lot of MBAs that build massive businesses and decent company cultures and it’s hard to categorically shit on people who are actually literally teed up to do a better job and statistically probably knock it out of the park.
My story is novel because I’m an outlier and that’s very cool but there’s a reason why I’m an outlier and there’s a reason why that’s … I think part of the reason that building a business was really hard for me and part of the reason Nasty Gal didn’t work out after 10 years, not a lot of things work out forever. But in the beginning, doing the job is the most important. And I think, even for startup founders, people who have funding or MBA folks, people who want to hire three assistants day one or delegate everything without knowing how to do it, you’re going to have a really hard time holding people accountable because you don’t even know what the jobs are to be done.
Tori Dunlap:
Yeah. Well, and one of the things I say a lot of the reason I think our business has had success and the thing I wish more people understood is done is better than perfect. And I think, again, the fear, the perfectionism seeps in with a lot of women who want to be entrepreneurs is it’s I don’t have the perfect idea, I don’t have the perfect brand. And one thing that I think you did better than anybody else is you’re like, “Yeah, this isn’t perfect but it’s getting done.” So, what are early stage founders often wasting time or energy on that you find doesn’t fucking matter?
Sophia Amoruso:
Definitely having things perfect, I think it’s better to just put that thing out into the world. In startup world, it’s called a minimum viable product and it’s startup, they’re building software that’s actually really crappy and they put it onto the world and they see how people like it and the thing they end up building is often completely different from what it is that they set out to do. And I think people can be very … We’re attached to our identities, we’re attached to what we say we’re going to do and tell people what we’re going to do and one word of advice is just don’t tell people what you’re going to do, just go do it because they’re going to be waiting around and asking did you do that. But I think just not being precious about … Your idea may not work out and that’s okay and the chances of it working out are probably pretty slim. The chance of something working out if you keep going is a lot greater.
Tori Dunlap:
So, your first business grew very quickly and I know firsthand that this can be very disorienting. What do you look back on and wish you would’ve done differently or what are you really glad you did?
Sophia Amoruso:
Oh. I wish I knew more about leadership, I wish I knew enough to coach people or even that I should and, like I talked about, knowing what the jobs are to hold people accountable. When you have a chief financial officer and a chief technology officer and a chief people officer and in-house counsel and a team of accountants, I didn’t do those jobs, I didn’t know how to hold those people accountable. No leader has done-
Tori Dunlap:
Candidly, I had googled what does a CPO, CFO do. Those are things that I don’t know what their job descriptions actually entail.
Sophia Amoruso:
And sometimes they give you bad advice and sometimes they don’t do what they say they’re going to do. So, I didn’t understand holding people accountable, I didn’t understand what they needed to do but just, at the very least, be like, “Oh, you said you were going to do this in three months,” and then four months would pass and I’d be like, “Weren’t you guys going to launch this thing?” And as a CEO, I didn’t realize that I had to hold the hands of people whose careers were longer than the entirety of my own life at that point, I was 27 and they had 20, 30-year careers doing what they were doing and they still needed to be, one, told what to do and then I had to check in and make sure … Nobody checked in with me, nobody was holding me accountable but I am an entrepreneur for a reason.
I learned the hard way by not holding people accountable that you should hold people accountable as a leader and I think that was a big lesson. That’s something I wish I’d done. And then the thing I’m glad I did was take money off the table.
Tori Dunlap:
Tell me more.
Sophia Amoruso:
So, we raised $50 million in 2012 and the company was super-duper profitable. The company didn’t need the money and that’s why I own a house and have financial freedom because I owned 100% of the company. So, some of that went to my pocket and the company became less profitable after we raised venture capital and that’s a much longer story. But I think a lot of people hold out to have the big exit, we’re going to whatever and my advice often is just take the money because you don’t know what’s going to happen.
Tori Dunlap:
So, for people listening, because you took money and exchange for ownership in the company, it sounded like it ended up dooming the company but benefiting you personally. Is that accurate?
Sophia Amoruso:
I guess so. The bigger-
Tori Dunlap:
That’s dramatic but …
Sophia Amoruso:
In some ways it doomed me. In the scheme of doing things, you could say that it doomed my opportunity to have made a lot more money had I owned 100% of the company.
Tori Dunlap:
Right, right.
Sophia Amoruso:
The company was doing $30 million in revenue a year profitably when we raised from venture capitalists. But I think, ultimately, fashion brands are not venture scalable and it was a different time, it was 2012, it was not called direct to consumer, it was called e-commerce. We didn’t have Shopify, I had to have a software team to build a shopping website, it was so different. And so, it was all just a shop in the dark and, ultimately, venture capitalists, myself included, are making bets we think are smart based on what we know now and a lot of that stuff’s going to go to zero, that’s part of it. And I’ve had two companies flame out in a few years of running my fund and that’s normal and other ones are going to knock it out of the park.
Tori Dunlap:
So, you said that you didn’t need the VC. Is it a simplified question to just to ask you why you took it? Was it on the counsel of other people? I think that, again, if I’m somebody listening who wants to start a business, I think there’s two camps. There’s the startup world of you need capital, you need investors, you need people backing you, I had jobs in that space and then the other side which is, no, I’m going to be scrappy and I’m going to build this but it sounds like those two intersected at some point.
Sophia Amoruso:
Yeah. I think, if you’re starting something, 99% of the time, do not get investors.
Tori Dunlap:
Yeah.
Sophia Amoruso:
And then, even once you’ve built something, 99%, you don’t need investors. Unless you’re building software, you’re first to market and speed’s important or you’ve got really expensive R&D then maybe you should raise money from day one. But most of the businesses, even the business I started and the majority of people who follow me and probably you on Instagram, they may be service providers, they may have an e-commerce brand, there are other ways to fund your business without investors and I recommend against it for most people.
When I raised $50 million, I sold 20% of the company and so I controlled the board, I had two board seats, my investor had one, I wish I had built an actual board with more smart, experienced people around the table but I heard boards were a nightmare so I was like, “Ah, I don’t want it to be complicated, I’ll just” … It wasn’t because I was controlling, I didn’t even know what I was controlling but it was like, “Oh, okay, cool, we can supercharge the business, we can grow it faster and hire the best creative director and have the best creative.”
And it was awesome building out a world-class team, really truly world-class talent and, obviously, a beautiful office space and stuff like that that doesn’t matter but, again, I was 27 and I was like, “I have my own bathroom next to my office, this is amazing.” And that stuff doesn’t matter, part of it was it was just because I could and there was not a huge, from my perspective at the time, there wasn’t a huge trade off.
And these very experienced investors were very, very convinced that I was going to build a billion-dollar business which was never what I had planned to do, I was happy with my $30 million a year business. I was like, “Okay, if that’s what you think I can do, great,” just who do I need to hire and they’re going to diagnose it and do that thing with me. And like I said, with holding talent accountable, it’s a lot more than just getting good talent on board, there’s a bigger job that’s yours to knit everything together and make sure that it all works and keeps moving the direction that everybody wants it to.
Tori Dunlap:
So, if I’m listening to you right now, I’m going, “Don’t trust anybody.” Okay, that there’s people out there who say they’re experienced but might not be and I have personal experience of that too of bringing people on because they said they’ve known what needs to happen and then they don’t. And at the same time, I don’t think I’d be where I am right now if I didn’t have also people who were really good at their jobs and really hard working. So, how do you figure out who you can trust or who do you invest in? Because I know that we need people, we need support as women entrepreneurs in order to grow what we’re trying to grow.
Sophia Amoruso:
I don’t know.
Tori Dunlap:
Sure.
Sophia Amoruso:
I still don’t know. I think the only way I’ve learned to trust people is by trusting them and I’m probably too trusting. But I’ve spent months courting potential C-level talent and then they quit their job and it’s two months later and then they start working for you and it’s week one and you’re like, “Oh, my God, this is a shit show.” So, it’s really hard to vet upfront, I think there’s a lot of … Andrew Wilkinson, all these guys have frameworks for how they hire people and I want to be that guy but I’m still not that guy and I could be a better … I think I’m actually now a better leader than I am a manager.
The people around you can only be as good as what you give them to be successful and the consistency that you show up with as a leader or a manager. And this stage of my life where I’m free, I moved to London and I’m not a girl boss anymore and I’m travelling, it doesn’t really lend itself well to leading a team and I don’t have a team. I have zero full-time employees now and one contractor and that’s fine because I don’t have an answer, honestly.
Tori Dunlap:
I think it’s one of the most difficult things, I would agree with that.
Sophia Amoruso:
It is.
Tori Dunlap:
I’m trying to think if I have an answer. I think for me it is the classic, when people show you who they are, believe them. And I think, for me, and I’ve talked to my COO who’s my right-hand woman about this, is because we care about people and because we assume positive intent, we are often giving people second and third and 16th chances because we’re always thinking, well, maybe something’s going on with them, maybe they didn’t understand, maybe we didn’t communicate well and sometimes that’s the case.
Most of the time, if there’s a problem, it’s not on us and it’s taken years and still we have to remind ourselves that you saw that problem six months ago, you need to handle it six months ago, you can’t wait six months to handle it. And I think that’s the thing I’ve learned is there are some people who come in and promise a lot and you might not be able to see through that but you need to be able to move quickly once you’ve discovered and once you start to have inklings about what’s going on.
Sophia Amoruso:
I don’t want my story to sound like don’t trust anybody. I think [inaudible 00:21:49] you know.
Tori Dunlap:
That’s what I want to prevent, yeah.
Sophia Amoruso:
No, almost everybody around me stuck with me when the shit hit the fan. I would say the number of people … I try to think about betrayal, that’s not a theme in my life. I’m not a litigious person, nobody’s really, really fucked me over. So, the number of people that have come in and out of my life, hundreds of employees and 50, 60 whatever million dollars and $1 million with talent and really smart people, there are people who don’t take responsibility for what they’ve done or didn’t do no matter how much you coach them or give them guidance. And most of them, most people I can tell, well, they want to do a good job, sometimes it’s just not a match but then there are the people who really just will not accept that they are blowing it. And if they do blow it, they’re angry and they’re like … I’ve had people just be like, “It’s you.”
And when you are an empathetic person who’s always trying to learn and not the leader who’s like, “Whatever, I’m right all the time,” I listen to all of it and I think it’s really hard to sort through what I have responsibility for and what other people have responsibility for because I think a lot of people are really cow shitty leaders and I think everything is an opportunity to learn. But I don’t want what I learned to teach me to tolerate other people’s failures of responsibility so it’s a tough one.
Tori Dunlap:
Yeah, totally. If you’re anywhere in a leadership position, whether as a business owner or as someone who manages teams, that last few minutes probably hit real hard. It’s certainly something I struggle with too. When we come back, we’re talking with Sophia about how to get over the fear of disappointing people when the cost on the other side is losing yourself, what it can mean to build a business that is successful for you and not anyone else and we also get into Sophia’s feelings about being the original #Girlboss. Stay tuned.
When you think about selling the company, do you feel like you had people that made you believe you had to keep caring for it? Was there a sense of you’re a bad person for letting this go? Because if this thing is your baby, how do you let that go and accept what’s happening but also accepting that you’re not the 100% owner of it anymore?
Sophia Amoruso:
Yeah. Nasty Gal sold in Chapter 11 so I didn’t even sell it, I stepped off the board so I wasn’t involved with the sale. I turned down a $400 plus million offer from an outfitter of urban clothing when I owned 80% of the company and I have that piece, I have it in my Dropbox, I have red lines, I still have it. And a company doesn’t go bankrupt overnight, there was a series of Hail Marys and acquisition offers but also meddling and new investors came in and, at that point, I really was … I’d been out of my league for a long time. The Girlboss thing happened, I was travelling a lot, the Netflix series was happening, I was writing a second book so I had stepped off. I had moved out of CEO, I hired a CEO for the last two years of the business, I didn’t want that job, I didn’t like it for all the reasons that we’ve discussed, I guess, but-
Tori Dunlap:
We just talked about, yeah.
Sophia Amoruso:
But I think there’s leadership and then there’s spiritual leadership. I did the selfish thing and I was like this has been so brutal already. I could be here as a spiritual leader for the team as people are getting laid off and the company is essentially getting shut down, the intellectual property was sold to Boohoo here in the UK but I’ve been through so much, I put 10 years in at what point can I protect myself and give myself what I need to just get through this and keep going. I don’t think it was the best example of leadership but there’s a certain point where you need to preserve yourself and you’re going to disappoint other people no matter what but I think I probably disappointed a lot of people doing that. For me, when I left the company, it was devastating but it wasn’t a surprise and, also, there had been years where I was like, “I can’t quit and I can’t be fired, this thing’s huge, I’ve raised money. What am I going to do? Shut it down. I don’t like this anymore.”
It’s crazy to say, “Oh, my God, this successful thing and all this attention and whatever it is,” but it’s a lot, it’s a lot. You can only hope that what it is that you set out to do is successful but you inherit things you could never have expected. And those are fun problems to solve but, when you’ve got hundreds of people, it’s a really different game. And I think, off topic, I inspired a lot of people to go big, whatever, and it’s, yeah, go big but bigger isn’t always better and investors aren’t usually the way and press is not the thing. There’s a whole picture that I think I was part of creating this, I don’t know what it was, prototype or something for what … Inspiring, yes, but also, oh, this is what I need to do and a lot of them were I need to raise money and I need a big team and this thing has to be this successful and it’s-
Tori Dunlap:
And I need magazine covers.
Sophia Amoruso:
… actually, you have a really awesome, profitable, manageable business and you get to go home at the end of the day to a certain … Run a business, it’s not a 9:00 to 5:00 especially with what we have digitally now to operate a business that you know better than anybody, you can have … There’s software that gets you so much leverage to have a really healthy business without a ton of people and it doesn’t have to be a million, $100 million business, it can be way more fun.
Tori Dunlap:
One, I think that you don’t need this from me but I think that shows so much maturity because I felt that way too in my early 20s and even talking with other entrepreneur friends who are a little bit further than me or a little bit older than me who have been like, “No, I’m okay at 300K a year. I’m okay at 200K a year. I’m okay at 150K a year. That’s enough for me to live my life the way I want to live it.” And that has caused a lot of friction, good friction in my life where I’m like, “No, I want to sell out arenas. I don’t know what I’m doing in those arenas but I’m going to sell out arenas and I’m going to, yeah, covers of magazines and I’m going to be everywhere.” It’s like, “Okay, but are you willing to do all of those things and also give up every single night and weekend?” and the answer is no.
The answer was yes for a while but I got older, my priorities shifted. I love the idea that I can take a random Wednesday off if I want to take a random Wednesday off. And I still think part of my business still isn’t there where there’s so much of my business that is way smaller than Nasty Gal ever was but that I don’t have total freedom around, I can’t take six months off but I can take maybe a month off. And so, that’s something that I think a lot of business owners discover is, yeah, if you want all of the big stuff, great, that’s not going to come without sacrifice.
Sophia Amoruso:
Mm-hmm, that’s true. This is why I don’t have a podcast right now. Girlboss Radio had 22 million downloads in 20 … I started it in 2015, it was 10 years ago and I couldn’t take off next week if I wanted to because someone would be in London who is only going to be here for two days and we booked it two months ago and now I have to be in London this week because I’m interviewing somebody on a podcast and I’m like … You can do yours remotely, a lot of people do theirs in person and so, with everything that you do, just think about what it tethers you to and how that might look, what that sacrifice is. And I literally won’t have a podcast because I want to be able to take off whenever I want, that’s literally the only reason. But you do it virtually, a lot of people don’t do that anymore and [inaudible 00:30:45]-
Tori Dunlap:
Well, our show suffers for it.
Sophia Amoruso:
Really?
Tori Dunlap:
My light just went out. My light in the office in my house just went out and it’s like, “Do the listeners care?”
Sophia Amoruso:
[inaudible 00:30:57] as well. Oh, you don’t think it will?
Tori Dunlap:
No, this is on … If you’re watching on YouTube which, yes, by the way, we have a YouTube channel, yeah, the video’s not going to perform as well, I knew that the moment the light went out and I was just like, “Fuck, okay.” And actually, that’s a perfect example of we could have the most interesting conversation in the world that is super impactful, that is very valuable, that is very vulnerable and there’s going to be some people who hear it and listen to it and respond to it and that’s great. But you’re fighting against algorithms, you’re fighting against having an in-person setup that looks really sophisticated, that costs tens and hundreds of thousands of dollars to produce and so, if the tree falls in the middle of a forest, it doesn’t make a sound. Again, we could do the best thing in the world right here but, if the algorithm’s not pushing it or if I’m not wearing the right color which, by the way, Sophia, is a real thing. If I show up in black, the video doesn’t perform as well, fucking crazy.
Sophia Amoruso:
I understand thumbnails more than anybody.
Tori Dunlap:
Right, right.
Sophia Amoruso:
I started on eBay. I started on eBay, it’s like [inaudible 00:32:05].
Tori Dunlap:
So true. So, it’s those things where, I don’t know, it’s what am I willing to do. Am I willing to fly out to LA or New York every other week so that I can film in person? No, I’m not willing to do that. Does the business suffer for it? Yeah, it does but those are the trade-offs you have to make.
Sophia Amoruso:
Yeah, but suffers, it could always be better, you can always do more. So, it’s is it suffering? How are you breaking-
Tori Dunlap:
Right. If my mental health is better, is it suffering? Right.
Sophia Amoruso:
If this is what you want to do, it’s not suffering.
Tori Dunlap:
Right.
Sophia Amoruso:
If you do what you don’t want to do, you’re suffering.
Tori Dunlap:
Yup.
Sophia Amoruso:
If your goals are in line with your ambition, then nobody suffers.
Tori Dunlap:
Yeah, totally. I wanted to ask you a question and you can tell me you don’t want to answer it. But something that candidly I’ve thought about a lot that I’ve always wanted to talk to you about is how it feels to have this thing that was part of your identity but also was something you produced become a joke or satirical. And again, super candidly, one of the things that I literally had conversations with my book editor about, my friends about is I said I don’t want financial feminists to ever be what Girlboss has turned into now and it feels really scary to admit that to you straight to your face. But how did that feel? How does that continue to feel? Because I know that there was parts of Girlboss and part of that movement that we can look back on and be like, “Eh, there were parts of that that probably might’ve been different if it was” … Definitely would’ve been different if it was in 2025. However, that would just break my heart, that would make me so sad.
Sophia Amoruso:
Yeah.
Tori Dunlap:
That’s probably the scariest question I think I’ve asked anyone on the show. When we come back, Sophia talks about her feelings around Girlboss now. We also get into her work now in VC, what she’s looking for when companies pitch her for funding and what successful business owners know that others don’t. We’ll be right back.
Sophia Amoruso:
You can only hope that what you create becomes part of the zeitgeist. You create something and you give it away. And when Girlboss took off and people called it a movement and, even today, I read your book, I quit my job, I started a business, it was there was lean in and then, a year later, there was Girlboss and there was nothing else like that. And these digital platforms were just emerging and there was no example that anybody had seen at that stage of some non-college at all educated girl starting on a digital resale marketplace and building something as sizable as I did. And so, the impact of Girlboss is something that is always going to be louder to me than whatever other people ran off with and did and so … It’s in the Merriam-Webster dictionary as of a year ago.
Tori Dunlap:
I didn’t know that, that’s crazy.
Sophia Amoruso:
Yeah, it’s actually a word. I think a journalist told me that, I didn’t know it until pretty recently, it might’ve been two years ago or something. It was no longer mine a long time before that and it’s something I did but I was 28 or it was 30, I think, maybe when it was published. And so, I’ve always been referenced as the creator of the word and wrote the book but, over the years, it just became its own thing. And so, it was more about the founders who came after me and became this calling card for a whole bunch of things like the rise of the girl bosses, the fall of the girl bosses and that whole thing. The reason it became satirical is the same reason that ambitious women get taken down.
Tori Dunlap:
Yes. That was going to be my next question for you, yup.
Sophia Amoruso:
Yeah. So, have at it guys but it’s just feeding the same thing and it’s you’re outdated actually. And it was a fucking pink book. I didn’t talk about being a woman, it was a pink … It’s a pink book I wrote when I was 28, I don’t take myself that seriously. So, I don’t know, I don’t know. That’s not that big of a thing to me because, again, every day I get emails and DMs from people who are like, “Oh, my God, your story inspired me, your book inspired me,” whatever it is, the Netflix series which I’m like, “That was a comedy but I’m glad it inspired you, I didn’t even write it.”
Tori Dunlap:
The impact, yeah.
Sophia Amoruso:
But that’s just always been so much louder to me. But I think the gift that you give people is something that is no longer yours and they can take and do what they want with. And when Girlboss was the thing and super inspiring, that was a gift. And when it became something that people could hold in contrast as a shorthand for feminism and capitalism, whatever, this bigger conversation that emerged and became more complex, that’s also a gift and that is an important conversation. So, if that’s what it became, then I’m also fine with that.
Tori Dunlap:
Yeah. Oh, I want to cry in a good way, I’m just like … Again, I hate to use the word mature but it’s a very wise response. I don’t know if I’d be able to do the same.
Sophia Amoruso:
Thanks.
Tori Dunlap:
I’d be so bitter, dude. I’d be so bitter, I’d be so angry.
Sophia Amoruso:
But you wouldn’t be when you’re walking to yoga yesterday in fucking London and some lady stops you on your line bike and is like, “Are you Sophia Amoruso? Oh, my God, I read all your books, I’m so inspired by what you’ve done.”
Tori Dunlap:
Yeah, yeah. Which I get all the time too.
Sophia Amoruso:
That’s what you go home … Yeah, exactly.
Tori Dunlap:
Totally, totally.
Sophia Amoruso:
Yeah, but had you gone through this and been bitter or whatever. But if that’s what happens when you’re fucking riding a bike to yoga, that’s not what I’m thinking about, I’m thinking about kinds of other dumb bullshit. It was so long ago, I’m thinking about, I don’t know what, UK taxes or something and how small my apartment is and what I’m going to do with three poodles.
Tori Dunlap:
Yeah, totally.
Sophia Amoruso:
That’s not what … Yeah.
Tori Dunlap:
And I think you make a good point and I’m not going to harp on it too much because I have actually discussed it in previous episodes especially, I don’t know if you know, Katie from Money with Katie but we talked about it is this societal pandemic that, when a successful woman becomes successful or when a woman becomes successful, it’s so easy to take her down, it’s so easy. And I think we really saw that in the 2010s and into this decade where, again, to your conversation we started with, when you put yourself out there, you’re out there and there’s a double standard, there’s a different standard for women entrepreneurs and women leaders than there is for men. And the example I brought up with her is Steve Jobs is praised and lauded as this incredible innovator but he was a terrible person, a terrible boss, screamed at people, abused people, didn’t shower for weeks on end and yet we seem to allow that sort of behavior when we don’t for women.
Sophia Amoruso:
Yeah. Can you think of any brilliant women who are assholes who are remembered who are just brilliant and it doesn’t matter that they were an asshole? Brilliant and iconic but they’re an … There’s probably actors-
Tori Dunlap:
The one we brought up was Martha Stewart but she literally went to jail so it’s-
Sophia Amoruso:
But she’ll do [inaudible 00:40:44]-
Tori Dunlap:
And went to jail for something that wasn’t insider trading which again proves the point which is you can be brilliant and difficult to work with and you will continually be targeted if you’re a woman. But if she was a man, it would just be very different, she would be lauded for the same traits but-
Sophia Amoruso:
It would be unfair-
Tori Dunlap:
Right, right.
Sophia Amoruso:
… if it was a guy and for her it’s how dare you.
Tori Dunlap:
Right. It’s just interesting to me and it continues to show up which is so shitty. And again, if I’m somebody listening who wants to be a business owner, who wants to put myself out there, that goes in the list of reasons to not do it. So, I don’t know if you have anything to say to that but I have to believe that-
Sophia Amoruso:
No, look at the impact. It’s the impact. Again, not everybody’s going to like what you do and I am not the thing that I wrote in 2013.
Tori Dunlap:
Totally.
Sophia Amoruso:
But the impact of this thing that I cast out into the world and gave to people to do whatever the fuck they wanted with is not me. It continues to make an impact.
Tori Dunlap:
That’s what matters.
Sophia Amoruso:
And if you’re going to be egotistical about it, suck it, it’s still impactful and people are still fucking talking about it. When I blew it, people were inspired. The worst look is saying you’re going to do something and not doing it. It’s a better look to do it and fail. Doing it and blowing it is a way better story than being that person that just fucking navel gazes. Nobody [inaudible 00:42:20]-
Tori Dunlap:
Sophia, I was just going to say it’s a better story. Okay, it doesn’t work out, well, cool.
Sophia Amoruso:
Yeah, cool.
Tori Dunlap:
You have one precious life, you have a dope story to tell now.
Sophia Amoruso:
Well, guess what? You get to take that with you.
Tori Dunlap:
The learnings, yeah.
Sophia Amoruso:
I don’t have a warehouse full of clothing I have to put on sale, I’ve got fucking decades of wisdom that I get to sell at 100% margin for the rest of my life. That’s what I got.
Tori Dunlap:
Yeah. Which is priceless.
Sophia Amoruso:
And I don’t need a warehouse and … Yeah, it’s fucking priceless.
Tori Dunlap:
Yeah. So, you’re in the VC space now where you’re writing checks. So, what should founders, especially women, know going into a room where they’re about to pitch a venture capitalist for money?
Sophia Amoruso:
I can tell you what I look for in a founder.
Tori Dunlap:
Yeah, right.
Sophia Amoruso:
I look for someone who has experienced the problem that they’re trying to solve because they’re going to have a lot of empathy for the end user and who they’re building their product or service or software for. So, somebody, if they don’t have actual domain expertise, then the next thing is they have domain expertise and they’ve worked in that area or they’ve worked at a company where they’re solving similar problems or have done similar engineering or brought a product to market that is in the same realm or industry that they’re planning to build in. Having a solid plan, honestly, having a team, having a solid co-founder. If you’re building something technical, having a solid co-founder. Not expecting a wild valuation, having your expectations in line with where you are in your business especially if you’ve done nothing.
I invest in founders that just have a deck, okay, and two of the best companies in the fund are the companies that hadn’t built anything, they’re the ones that have broken out and raised subsequent sizable rounds from really top tier VCs but, again, most people don’t need to talk to investors until after they’ve done something. So, put something out to the world, get some idea that you’re solving a real problem that’s not just your own and be able to, I guess, articulate what it is that you plan to build, how it’s going to make money. A lot of people, I have an online course called Business Class and there’s a lot of folks in there who are like, “I want to build a community,” and it’s like, “What’s that?” Is that a business? Is it a membership? Is it an app? Is it an online course? But it’s like, “I want to build a community for women.” And I think I’m just, at this point, I’m just like-
Tori Dunlap:
What does that mean?
Sophia Amoruso:
… “I don’t want to talk about that. I did that kind of.” My second business was Girlboss, it was a media company and we had huge conferences, whatever, doing brand partnerships and all that shit but it’s like, “But what’s the business? What’s the business model?” You don’t build a thing and then figure out the business model, you think about the business model first.
Tori Dunlap:
Yeah. What do you feel like successful entrepreneurs know that the rest of us don’t?
Sophia Amoruso:
What’s a successful entrepreneur? Well-
Tori Dunlap:
Maybe that’s a good first question. Your definition of success has clearly changed so is mine. So, maybe it’s is it traits of … I think, just listening to your story, one is knowing what you actually want and knowing that that changes. I think, even in the hour 45 minutes I’ve been talking to you, that’s clearly something that you know now that maybe you didn’t know when you started and that’s so important.
Sophia Amoruso:
Yeah, it’s so important. I’m 41 though, it took a really long time and it took doing it to figure out that I didn’t want to do all those things. But when you haven’t done it, it’s not the worst advice to say just go do it especially when you’re young. So, if you can tolerate working really hard and not burn out and be miserable and you’re having fun and you’re learning and it’s working out, that is the most fun path to go down. But if it’s coming at the expense of things that you do know that you want, then that’s something to think about.
What is successful? I think they persevere, they just keep going, they’re willing to solve problems, they’re willing to pivot their business, they’re willing to lay people off, start back up from scratch, build something else. Whatever needs to happen for them to achieve what they have set out to do or what they really, really, really believe could be successful or make an impact. I think it’s the founders that keep going that are more successful than the rest of us.
Tori Dunlap:
Thank you for listening to the incredible sponsors that allow this show to run for free for you. So, when we come back, we’re closing out our conversation with Sophia by talking about her business coaching program and her advice for those of us who have just gone through a lot of failure on how to keep on trucking. Stay tuned.
I love what you’re doing with Business Class, I truly don’t know anybody who’s as good at branding as you.
Sophia Amoruso:
Thanks.
Tori Dunlap:
I saw that landing page and I was like, “Oh, God, this is so good.”
Sophia Amoruso:
Thank you. Thanks.
Tori Dunlap:
It looks so good, it’s such a good name, it’s just fantastic.
Sophia Amoruso:
Thanks.
Tori Dunlap:
So, talk to me about what’s going on in Business Class. What are people learning? What are the takeaways? What transformations are you seeing for largely, I’m assuming, women that join Business Class?
Sophia Amoruso:
Business Class in an online course I created during COVID, actually, in 2020 when I left my second company Girlboss, it was like, “I want a digital business, I want something that can scale, that’s outsized to its footprint.” I’d been doing a media company and conferences and had 25 people at my second company, it was like, “I can do this super nimbly. What’s this thing called Kajabi?” Okay, email marketing, automation.” I understood marketing and I understood a lot of this stuff already but there was a fucking playbook so I was like, “All right, I have all this knowledge, everybody’s always asking me questions, how can I scale that? How can I give it to as many people as possible without” … I can’t consult for everybody. So, create a Business Class which you can’t hear the branding on this podcast or see it but it’s aviation themed. So, Business Class, you’re on a plane and you’re in business class but it’s Pan Am, it’s like me dressed as-
Tori Dunlap:
It’s so good.
Sophia Amoruso:
… a 1960s flight attendant teaching it and every module is called a flight. There’s flights and legs and layover weeks where we take a break and it’s just super, super fun and funny and punny and mixed learning fun which I just always think it should be. And so, we start with finding your strengths which we call your jet fuel and figuring out where you need to augment those strengths and just understanding that you aren’t necessarily going to be the person that has to do everything. And then auditing your idea, putting it out into the world, putting that MVP or minimum viable product out into the world, seeing what people have to say about it even if it’s your friends and family and grandma. We talk about mapping your competition then we talk about marketing and earned, owned, paid and certain amount of funnels and we have some bonuses on things like negotiating. We go through intellectual property and money and some legal stuff and leadership and brand loyalty and a whole lot of things.
So, it’s an eight-hour course, there’s 300 pages of worksheets, we do weekly co-working sessions and have different hosts and sometimes I interview people that’s exclusive to the community. And so, there’s something called The Lounge which is our digital community with 3,500 entrepreneurs in there-
Tori Dunlap:
Cool.
Sophia Amoruso:
… and everyone’s just talking all day long about what it is that they’re building and asking questions and they’re putting their mood boards together or their branding together or asking what people think about it or dropping the link to their website and asking other people to test it and give them feedback if there are any links broken. And so, yeah, we’ve had founders go from zero to selling out in the first few weeks. The testimonials are on the website but it’s mostly bootstrap founders so it’s not a lot of venture backed companies. It’s I do the venture thing with companies that are a select few that I think can build a billion-dollar business, really, but then there’s the rest of us, myself included, who are building a different business because I don’t want to do that again. I love working with both the bootstrap founders and small business owners and then also the software venture-backed guys who were shooting for the stars and might actually land and stay there.
Tori Dunlap:
So, my last question for you. You’ve been through a lot of survival mode, what’s your advice to someone feeling stuck in that scarcity or in that survival mode but know that they’re destined or that they want more?
Sophia Amoruso:
Just everything changes, you’re just not going to be there forever. I don’t have advice on how to solve your problem right now, everybody’s problem is different but just know that how you feel now is not going to be how you feel in two years and, the hardship you’re experiencing now, you might even laugh at in a year so have perspective. And you’ve asked me a lot of questions, you’re like, “I would be bitter,” but I can laugh at all this stuff. At the end of the day, it’s that’s so funny that there’s a Netflix series about my life whether the press liked it or not is less interesting to me than being like, “Haha.”
Tori Dunlap:
No, you’re so right. If we’re doing it for the plot-
Sophia Amoruso:
That’s crazy.
Tori Dunlap:
… it’s a great plot point.
Sophia Amoruso:
Yeah, yeah, that’s it. It’s just, yeah, it’s like … But also, yeah, if you’re feeling stuck, also, just try different things, don’t blow all your savings on it but something might land and it might not be the thing that you expect it to and don’t be so precious that you’re not going to identify that and don’t be so rich that you don’t have to go for it.
Tori Dunlap:
Right. This is actually such a poetic interview for me so thank you.
Sophia Amoruso:
Good.
Tori Dunlap:
No, it’s just a reminder to me about, yeah, what’s actually important. Is it important that you did the thing you said you were going to do and that it hopefully makes an impact, those are the things that are important.
Sophia Amoruso:
And even if you don’t end up doing-
Tori Dunlap:
Public scrutiny, whatever.
Sophia Amoruso:
Yeah. And even if you don’t end up doing the thing you said you were going to do, it can all work out.
Tori Dunlap:
Yeah, totally.
Sophia Amoruso:
Even if it falls apart, it can all work out.
Tori Dunlap:
Yup. Nope, it’s so wise. Thank you, thank you for being here.
Sophia Amoruso:
Yeah.
Tori Dunlap:
Business Class. What else do you want to plug, my friend?
Sophia Amoruso:
Trust Fund my venture fund if you’re going to go build the next Uber or something, businessclass.co, I don’t know. Yeah, no, I’ve watched your career and you create content and be best in class at what you do and I wish I could be the machine I once was and you are and I really admire what you’ve built and think what you’re doing is really important and thanks for letting me be part of it.
Tori Dunlap:
Thank you, I appreciate it. Thanks for being here.
Sophia Amoruso:
Yeah.
Tori Dunlap:
Thank you to Sophia for joining us. You can find more information about Sophia and Business Class at her website, sophiamoruso.com. Thank you for supporting feminist media, thank you for being here, team. I don’t plug as much as I used to but, if you would like to subscribe to the show, I would really appreciate it, your brain would really appreciate it. If you want to send this episode to someone in your life, just spark a conversation, these two things are the best things you can do to help support this show even when it’s very, very difficult in general to run a feminist media company especially in the United States right now. So, we appreciate all of the support you can give us to continue making this show for you. Thank you so much, we’ll see you back here very soon. Okay, bye.
Thank you for listening to Financial Feminist a Her First 100K podcast. For more information about Financial Feminist, Her First 100K, our guests and episode show notes, visit financialfeministpodcast.com. If you’re confused about your personal finances and you’re wondering where to start, go to herfirst100k.com/quiz for a free personalized money plan.
Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristen Fields and Tamisha Grant. Research by Sarah Sciortino. Audio and video engineering by Alyssa Midcalf. Marketing and Operations by Karina Patel and Amanda Leffew. Special thanks to our team at Her First 100K, Kailyn Sprinkle, Masha Bakhmetyeva, Sasha Bonar, Rae Wong, Elizabeth McCumber, Daryl Ann Ingman, Shelby Duclos, Meghan Walker, and Jess Hawks. Promotional graphics by Mary Stratton, photography by Sarah Wolfe, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First 100K community for supporting our show.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over five million women negotiate salaries, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of over 2.1 million on Instagram and 2.4 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
