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

Episode Date: August 4, 2025

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

Imagine building a hundred million dollar 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 hashtag girl boss.

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. She is now a successful investor and entrepreneur with her two businesses, Trust Fund and Business Class. Being yourself gives other people permission to be themselves. Taking like big swings gives other women the opportunity to do the same thing. 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. Doing it and blowing it is like a way better story than being that person that just fucking

navel gazes. 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. The thing about people knowing your name is it's like less interesting that they know your name. It's more interesting that there's something to do with your name. She also gets real about surviving public scrutiny and also having the very book and so much of her identity kind of be mocked by society. Not everybody's gonna like what you do. And like I'm not the thing that I wrote in 2013. 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 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 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 multimillion 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. This episode of Financial Feminist is sponsored in part by Squarespace, Rocket Money, NetSuite, and Masterclass. Whether it's for a brand, portfolio, or store, Squarespace makes it easy. Head over to squarespace.com slash ffpod and use code ffpod for 10% off your first purchase. Stop paying for subscriptions you forgot about. Rocket Money finds and cancels them for you. Go to rocketmoney.com slash FF pod to take control of your finances. Running a growing business?

NetSuite helps you manage it all in one place. Download the free CFO's guide to AI and machine learning at netsuite.com slash FF pod. Learn from the best to become your best with Masterclass. Get 15% off any annual membership at masterclass.com slash ffpod. 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, navigates 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, like, falling back to Earth moment that you're most grateful for in hindsight? I mean, I think it was whenever everything should hit

everything shit the fan and late 2016 and it was like the you know nasty girl fell apart the day Trump was elected and Hillary lost and then this Netflix series Came out about my life that this alone is like a whole this Netflix series came out about my life. This alone is like 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 the hardest part of it all, there's a lot of hard things that happen this year. My husband that like left me right, you know, earlier in 2016 was when this series came out

and there were headlines like the worst thing about Netflix's girl boss 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 like, you know, what I do, that like 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. is what I've learned and the rest of it doesn't really matter. Well, what a way to start an interview. When we talk about that sort of theme a lot on this 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 love, we feel like we have to earn respect. And it sounds like through, unfortunately, a very like public, multi 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. Yeah, I think so. If anything would be like easier to accomplish less, like I feel like it's easier to be loved when you're when you're like a trad wife or something. But Well, no, I think that's actually You guys talk about trad wife stuff on this podcast. We do, unfortunately. That's a whole nother... I don't want to devolve the conversation

in the first five minutes into that. I'm so curious. 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, like the poster child of, which is like 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, like 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 I mean, 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. Yeah, I mean, I think like, the thing about people knowing your name is it's like less interesting that they know your name, it's more interesting that there's something to do with your name is it's like 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. Like, I think the runoff of what I've done matters more to other people than it does to me. And that's like a really special thing.

And so I think like, you know, being yourself gives other people permission to be themselves, taking like big swings gives other women the opportunity to, the space to, and also the confidence to do the same thing. And when you fuck up, honestly, like, they fought, they keep following you because they're like, Oh my god, I fucked up too. It's like, no matter what, like, if I fuck up on stage at a conference, they're like, you're so relatable. And so I'm're like, oh my God, I fucked up too. It's like, no matter what, like if I fuck up on stage at a conference, they're like, you're so relatable. And I'm just like, I just wanna be, I wanna do a good job. But so it's like, no matter,

like I think what you do as yourself, like other people are looking at you and being like, oh, actually like that's relatable. And we're really hard on ourselves. And at the end of the day, I think just like, you know, 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 like the big, the thing that people will remember and the thing

that people's changes people's lives is is in your DMs, right? It's in my DMs. And it happened, you know, I wrote that book in 2013, came out in 2014. And, you know, it's like the long-tail effect of doing something that inspires people. It's like worth every minute of it. Yeah. Well, and I'd love to go back to the beginning for people who might not be familiar with like the origin story. So you had a very non traditional path,

hitchhiking, selling a stolen book to build a fashion empire. Like what were those scrappy early years teaching you about business that no NBA could? Yeah. Well, I think, you know, NBA, you learn from listening and maybe some case studies and maybe, you know, going out and interning, but it's really different when it's your business. 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 NBA. I certainly think that if you don't have an NBA, you it would be helpful to work for someone else. Just even if there's bad leader to be like,

oh, this is what it's like to work for someone else. I had worked in shoe stores, like 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 like massive businesses and like decent company cultures. And it's like, it's hard to kind of categorically shit on, you know, people who are actually literally teed up to do a better job and statistically probably like knock it out of the park. I mean my story is novel because I'm an outlier and that's very cool but like there's a

reason why I'm an outlier and there's a reason why there you know that's I think part of the reason that building a business was really hard for me and part of the reason like NASA y'all didn't work out after 10 years. I mean not a lot of things work out forever. But in the beginning, like, you know, doing the job is the most important. And I think even for startup founders, people with funding or MBA folks, like people who want to hire like three assistants day one, or delegate everything without knowing how to do it, you're gonna have a really hard time holding people accountable because you don't even know what the jobs are to be done. Yeah. Well, and one of the things I say a lot of the reason I think our businesses had success and the thing I wish more people understood is like 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 like, 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? I mean, definitely having things perfect, or things better to just put that thing out into the world. You know, in startup world, it's called a minimum viable product. It's like startup, they're building software that's actually really crappy. And they put it out into 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 there's, I think people can be very, I mean, we're attached to our identities, we're attached to what we say we're going to do and tell people we're going to do. And one word of advice is just like, don't tell people what you're going to do, just go do it, because they're going to be waiting around and asking, like, did you do that? But I think just like not being precious about, you know, 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. 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 have done differently, or what are you really glad you did? Oh, I wish I knew more about leadership. I wish I knew enough to coach people, or even that I should. 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 and like that I didn't do those jobs. I didn't know how to hold those people accountable. I mean, I can't believe I had Google's like what is what is a CPO CFO do? Like those are those are things that like I don't know what their job descriptions actually entail. 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're going to do this in three months and then like four months would pass. And I'd be like, weren't you guys going to launch this thing? Right. 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. Like I was like 27 and they had like 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 like I'm 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. Tell me more. 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 own 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 like, you know, a lot of people hold out to have like the big exit, like we're gonna like, you know, whatever. And my advice often is just like, take the money because you don't know what's going to happen. Because you don't know what's going to happen. So for people listening, because you took money in exchange for ownership in the company, that it sounded like ended up kind of dooming the company, but benefiting you personally? Is that accurate? I guess so. I mean, the bigger...

That's kind of dramatic. I mean, in some ways it doomed me. I mean, in the scheme of doing things, it's like you could say that, you know, it doomed my opportunity to have made a lot more money had I owned 100% of the company. Right. 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 like e-commerce. We didn't have Shopify. I had to have like a software team to build like a shopping website. It was so different. And so it was all just kind of like a shot in the dark and ultimately like venture capitalists, myself included, are like making bets we think are smart based on what we know now. Yeah.

And a lot of that stuff's going to go to zero. That's part of it. And that's like, I've had two companies flame out in a few years of running my fund. And it's like, that's normal, you know, and other ones are going to knock it out of the park. So you said that you didn't need the VC. Is it a simplified question just to ask you why you took it? Was it on the counsel of other people? Like, 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. Like I had jobs in that space. And then the other side, which is like,

now I'm gonna be scrappy and I'm gonna build this. But it sounds like those two intersected at some point. Yeah, I mean, I think if you're starting something, 99% of the time, do not get investors. 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, the type of you know, they may be service providers, they may have like an e commerce brand, like there are other ways to fund your business without investors. And I, I recommend against it for most people. Yeah. 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 experience people around the table.

I heard boards were like a nightmare. So I was like, I don't want it to be complicated. It wasn't because I was controlling. I didn't even know what I was controlling. But it was like, I don't want it to be complicated. 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, have the best creative. And it was awesome building out a world class team, like really, world-class talent and obviously like a beautiful office space and stuff like that that like doesn't matter but like

again I was like 27 and I was like you know I have my own bathroom next to my office. Right. It was like amazing and that stuff doesn't matter part of it was it was just good like I could and there was not a huge from my perspective at the time you know 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 like, who do I need to hire and they're going to diagnose it and do that thing with me, right? 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 in the direction that everybody wants it to. So if I'm listening to you right now, I'm going, don't trust anybody. Like, 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 hardworking. So how do you figure out who you can trust or who do you invest in? Because I don't, I know that we need people, we need support as women entrepreneurs in order to grow what we're trying to grow. I don't know.

Sure. Like, I still don't know, you know. I think the only way I've learned to trust people is by like trusting them. And I'm probably too trusting, you know, but it's like I've spent, you know, months courting potential C-level talent and then they like quit their job and it's two months later and then they start working for you and it's like week one and you're like, oh my god, this is a shit show. So it's like, it's really hard to vet upfront. I think there's a lot of, you know, Andrew Wilkinson, like all these guys have like frameworks and like for how they hire people and like I want to be that guy, but I'm still not

that guy. And I could be a better, like 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 you know this this stage of my life where I'm like, I'm free, I moved to London and like, you know, I'm not a girl boss anymore and I'm, you know, traveling. It's like, it doesn't really lend itself well to leading a team and I don't have a team. Like, I have zero full-time employees now. Yeah. And one contractor, and that's fine. Yeah.

Because I don't have an answer, honestly. I think it's one of the most difficult things. I would agree with that. It is. I'm trying to think if I have an answer. I mean, I think for me, it is the classic, like, when people show you who they are, believe them. And I think for me, and I've talked to my COO, who's like 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, like, 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, like, 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. I mean, I don't want my story to sound like don't trust anybody. I think that's what I want to prevent. No, I mean, almost everybody around me like stuck with me when the shit hit the fan.

I would say like the number of people I'm trying to think about like betrayal, like 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 million dollars 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 people can tend well, they wanna 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, right? And when you're an empathetic person who's always trying to learn and not the kind of 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's shitty leaders and I think everything is an opportunity to learn. But I don't want that, what I learned to teach me to tolerate other people's failures of responsibility. So, it's a tough one. Totally. If you are 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 hashtag girl boss. Stay tuned. This podcast is brought to you by Squarespace. One of the biggest things I hear from people who want to be business owners is they don't know where to start. They're like, I don't know what to do. I'm so overwhelmed. I want to start this business, but I need a logo and I need brand colors. And they make a million excuses to prevent them from getting started

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Yeah. I mean, 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. Sure. And when I owned 80% of the company. And I have that piece, I have it in my drop box. I have red lines, I still have it. And before, 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 kind of... I mean, I'd been out of my league for a long time. The Girlboss thing happened. I was traveling 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. But I think like, you know, there's leadership and then there's like 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's essentially getting shut down and the intellectual property was sold to Boohoo here in the UK. But like, 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? can't quit and I can't be fired. This thing's huge. I've raised money. What am I gonna do? Shut it down.

I don't like this anymore. It's crazy to say like, oh my God, this successful thing and all this attention and whatever it is, but it was like, 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 like, you know, kind of off topic, like I inspired a lot of people like go big, whatever and it's like, yeah, go big, but bigger isn't always better. And investors aren't usually the way. And press is not the thing, you know, there's a whole kind of like picture that I think I was part of like creating this. I don't know what it was like prototype or something for like what inspiring.

Yes, but also, oh, this is what I need to do. And a lot of them are like, I need to raise money and I need a big team and this thing has to be this successful. And it's like, actually, you can have a really awesome profitable, manageable business and you get to go home at the end of the day to a certain extent. I mean, run a business, it's not a nine to five, especially with what we have digitally now to operate a business that you know better than anybody. It's like you can have, there's software gets you so much leverage to have like a really

healthy business without a ton of people. And it doesn't have to be a million, a hundred million dollar business. It can be way more fun. 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, like 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 like 300k a year. I'm okay at 200k a year. I'm okay at 150k. Like that's enough for me to live my life the way I want to live it.

And that is, uh, 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 like, I'm going to sell out arenas and I'm going to, yeah, covers of magazines and I'm going to be everywhere. And 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 was 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 Caliber was, but that I can't, 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. Yeah, if you want all of the big stuff, great. That's not going to come without sacrifice. It's true.

I mean, this is why I don't have a podcast right now. Like Girlboss Radio had 22 million downloads and like, you know, 20, I started in 2015. It was like 10 years ago, you know, and it's like, I would have, I would, I couldn't like take off next week if I wanted to because someone would be in London who is only going to be here for two days. I 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.

So it's like with everything that you do, just think about what it tethers you to and how that might look, what that, what that sacrifice is. And I literally won't have a podcast because like, I want to be able to like take off whenever I want. You know, that's like the one, that's literally the only reason. But you do it virtually. Like a lot of people don't do that anymore. And well, our show suffers for it, but my light just went out. Like, my light, my, my, you know, the office in my, in my house just went out, you know, and it's

like, but do your listeners care? Uh, you don't think it will? No, it's, it's, this is on, if you're in Washington, YouTube, which yes, by the way, we have a YouTube channel. Um, yeah, the video is not going to perform as well. Like I knew that the moment the light went out and I was just like, fuck, okay, you know, and that's actually, that's a perfect example of like, we could have the most interesting conversation in the world that is super impactful, that is, you know, 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 it's like if the tree falls in the middle of the forest, it doesn't make a sound. Again, we could do the best thing in the world right here. But if the algorithm is not pushing it, or if I'm not wearing the right color, which by the way, Sophia is a real thing. Like if I show up in black, the video doesn't perform as

well. Like fucking crazy. I mean, I understand thumbnails more than anybody. Right, right. I started on eBay. I started on eBay. So true. Yeah. So it's like, it's those kind of things where, I don't know, it's like, what am I willing to do? Like, 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 like those are the trade-offs you have to make. Suffers like it could always be better. Right. You can always do more. So it's like, is it suffering? Like what you're like, how is it suffering? Right. If this is what you want to do, it's not suffering. Right.

You know, if you do what you don't want to do, you're suffering. Yep. Like if your goals are in line with your ambition, then nobody suffers. Yeah, totally. I wanted to ask you a question and you can tell me we, you don't want to answer that. But something that candidly I've thought about a lot that I've always wanted to talk to you about 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 kind of become a joke or like 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 like girl bosses turned into now.

And it feels really scary to admit that to you straight to your face. But like, how did that feel? How does that continue to feel? Because I know that there was parts of, you know, Girlboss and part of that movement that we can look back on and be like, ah, there were parts of that that, you know, probably might've been different if it was, definitely would've been different if it was, you know, in 2025.

However, that would just break my heart. Like that would make me so sad. 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. It is an interesting time to run a business. Between talks of tariffs and trade policies and supply chains and just the talk of the recession coming, it's just a lot.

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who was a better teacher for teaching me how to use a knife properly than the chef himself, the king of chefs. Right now, our listeners get an additional 15% off any annual membership at masterclass.com slash FF pod. That's 15% off at masterclass.com slash FF pod. Masterclass.com slash FF pod. I mean, you can't control, 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 like, 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, you know, the impact of

girl boss is something that is always going to be louder to me than like whatever other people ran off with and did. And so, I mean, it's in the Merriam-Webster dictionary. Like it's as if like a year ago. That's crazy. Yeah, it's like actually a word. I know, I think like a journalist told me that. I didn't know it until like pretty recently. It might've been like two years ago or something. Like it was no longer mine like a long time before that.

And I like, it's like something I did, but I was like 28 or I was like 30, I think maybe when it was published. And so I, you know, 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 just became its own thing. And so it was more about the founders who came after me and became this kind of 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. I mean, the reason it became satirical is the same reason that ambitious women get taken down. Yes, that was going to be my next question for you. Yeah, so have at it guys, you know, but it's all it's just feeding like the same thing.

And it's like, you're outdated, you know, actually. And it's like, it was a fucking pink book. I didn't talk about being a woman. It was just like, it was like a pink, it's like a pink book I wrote when I was 28. Like I don't take myself that seriously. So, I don't really like, I don't know, I don't know. That was like, that's like not that big of a thing to me because again, like every day I get emails and DMs from people who are like, oh my God, like your story inspired me, your book inspired me, whatever it is, Netflix series, which

I'm like, that was a comedy, but like, I'm glad it inspired you, you know, like I didn't even write it. But like, you know, that's just always been like so much louder to me. So but I think like, you know, 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 to, you know, have as a shorthand for feminism and capitalism, like whatever this bigger conversation that, you know, emerged and, you know, became more complex and like, 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. Yeah. Oh, I want to cry in a good way. I'm just like, that's it. Again, I hate to use the word mature, but it's like a very, like, it's a very wise response. I don't know if I'd be able to do the same. I'd be so bitter, dude. I'd be so bitter. I'd be like so angry. But you wouldn't be when like you're walking to yoga yesterday in fucking London and some lady stops you on your line bike and is like, are you Sophia Marousso?

Oh my God, I read all your books. Like I'm so inspired by what you've done. Which I get all the time too. That's what you go home. Yeah, exactly. Like, yeah, but you know, had you gone through this and been like bitter or whatever, it's like,

but if that's like what happens when you're fucking riding a bike to yoga, like that's not what I'm thinking about. I'm thinking about all kinds of other dumb bullshit. But so long ago, I'm thinking about like, I don't know what, like UK taxes or something. And like, you know, how small my apartment is and what I'm gonna do with three poodles.

Like, that's not what, you know, yeah. And I think you make a good point and I'm not gonna 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, like, 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, you know, 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 it's like Steve Jobs is praised and lauded as this incredible innovator. But like, he was a terrible person, like a terrible boss, like he 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. Yeah, can you think of any like brilliant women who are assholes who are remembered remembered, who are just brilliant, and it doesn't matter that they were an asshole, brilliant and iconic, but they're not, I mean, they're probably actors. The one we brought up was Martha Stewart, but she literally went to jail.

So it's like, and went to jail for something that wasn't insider trading, which again, proves the point, which is you can be brilliant and 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 very different, for the same traits. It would be like unfair. Right. If it was a guy and for her it's like, you know, how dare you? Right. It's just interesting to me.

And it like 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- No, it's like the, like, look at the impact. It's the impact. It's like, you know, again,

not everybody's gonna like what you do. And I'm not the thing that I wrote in 2013. Totally. 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. And if you're going to be egotistical about it, it's like, 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. Sophia was just going to say it's a better story. Okay, it doesn't work out.

Well, cool. You have one precious life. You have a dope story to tell now. Well, guess what? You get to take that with you. Like I don't have a warehouse full of clothing now. Well, guess what? You get to take that with you. I don't have a warehouse full of clothing I have to put on sale. I've got like fucking decades of wisdom

that I get to sell at 100% margin for the rest of my life. That's what I got. Yeah. And I don't need a warehouse. And yeah, it's fucking priceless. 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? I mean, I can tell you what I look for. Yeah, great. A founder. 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, you know, software for.

So somebody, if they don't have actual domain expertise, then the next thing is like they have domain expertise and they've worked in that area or they worked at a company where they're solving similar problems or have done similar kind of engineering or brought a product to market that is in the same kind of like realm that, or industry that they're planning to build in. Having a solid plan, I mean, honestly, having a team, like having like a solid co-founder,

if you're building something technical, having a solid co-founder, not expecting like 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, like most people don't need to talk to investors until after they've done something. So like put something out to the world, get some idea of like what, that you're solving real problems 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, you know, I do, 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? You know, that's, is that a business? You know, 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 like, at this point, I'm just like, I don't want to talk about that. Like I did that kind of like, you know, my second business was Girlboss and it was a media company and we had huge conferences, whatever, doing grand partnerships and all that shit.

But it's like, you know, but what's the business? What's the business model? You know, you don't build a thing and then figure out the business model. You like think about the business model first. What do you feel like successful entrepreneurs know that the rest of us don't? Like what's a successful entrepreneur? Well, maybe that's a good first question. Your definition of success has clearly changed. So has mine. So maybe it's, is it traits of, like, I mean, I think just listening to your story, one is it's like, knowing what you actually want, and knowing that that changes. I think even in the hour 45 minutes I've been talking to you, like, that's clearly

something that you know now that maybe you didn't know when you started. And like, that's so important. It's so important. I'm like 41 though, 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 think, just go do it, especially when you're young. So, it's like 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 and 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, you know, that's something to think about. Um, what is successful? I mean, I think it's, they like persevere, like they just keep going. They're willing to solve problems. They're willing to pivot their business. Like 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. 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. When you're a business owner, you need to hire people. That is one of my top tips for business owners, is we think we can do it all and we can't. We have to hire people in order to grow.

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Just go to indeed.com slash FFPOD right now and support our show by saying you heard about Indeed on this podcast. Indeed.com slash FFPOD. Terms and conditions apply. Hiring? Indeed is all you need. We all love a European summer. We love traveling, especially internationally.

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Like I saw that landing page and I was like, oh God, this is so good. It looks so good. It's such a good name. Like it's just fantastic. 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? Business class is an online course I created during COVID actually in 2020. When I left my second company, Girlboss, I was like, I want a digital business. I want something that can scale that's outsized to its footprint. You know, I've been doing like, you know, a media

company and conferences and had, you know, 25 people. My second company was like, I can do this super nimbly. What's this thing called Kajabi? Okay, email marketing and automations. I mean, I understood marketing. 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 like, I can't consult for everybody, right? 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, like you're on a plane and you're in business class, but it's like kind of Pan Am. It's like me dressed as a 1960s flight attendant teaching it.

And every module is called a flight. There's like flights and legs and, you know, layover weeks where we take a break. And it's just super, super fun and funny and punny and makes learning fun, which I just always think it should be. And so, you know, 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 like your friends and family and grandma. We talk about mapping your competition, then we talk about marketing and earned, owned, paid, you know, certain amount of funnels and we have some bonuses on things like negotiating. We go through like 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. And everyone's just kinda talking all day long about what it is that they're building and asking questions.

They're putting their mood boards together or their branding together, 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 they're already links broken. And so yeah, we've had founders go from like 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 like,

I do the venture thing with companies that are select few that I think can build like a billion dollar business really. But then there's like the rest of us, myself included, who are building a different kind of business. 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. 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? Just like everything changes. Like, you're just not going to be there forever. Like I don't have advice on how to solve your problem right now. Everybody's problems different, but just know that how you feel now is not going to be how you feel in two years. And like the hardship you're experiencing now, you might even laugh at in a year.

So like have perspective, and you've asked me a lot of questions of, you're like, I would be bitter. But I can like laugh at all this stuff. It's like at the end of the day, it's like, that's so funny that there's a Netflix series about my life, whether the press liked it or not is like, less interesting to me than being like, haha. No, you're so right. I mean, if they're doing it for the plot, it's a great plot point.

Yeah, that's it. It's just like, yeah, it's kind of like, but also, yeah, if you're feeling stuck, it's like, also, just like, try different things, you know, 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. Right. This is actually such a poetic interview for me. So thank you.

Um, no, I just like, it's just a reminder to me of like, 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. Like, and even if you don't end up doing the thing thing you said you were going to do, it can all work out. Yeah, totally. You know, even if it falls apart, it can all work out. Yep, no, it's so wise. Thank you, thank you for being here. Business class, what else do you wanna plug, my friend?

Trust fund, my venture fund, if you're gonna go build the next Uber or something. Businessclass.co, I don't know. Yeah, no, I really, I've watched your career and you create content and you 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. So thanks for letting me be part of it. Thank you. I appreciate it.

Thanks for being here. Thank you to Sophia for joining us. You can find more information about Sophia and business class at her website, sophiamaruso.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 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 herfirsthundredk.com slash quiz for a free personalized money plan. Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristin Fields and Tamesha Grant. Research by Sarah Shortino. Audio and video engineering by Alyssa Midcalf. Marketing and operations by Karina Patel and Amanda Lafue. Special thanks to our team at Her First 100K. Kaylin Sprinkle, Masha Bakhmageva, Sasha Bonar, Ray Wong, Elizabeth McCumber, Darrell Ann Ingman, Shelby Duclos, Megan Walker, and Jess Hawks.

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