In short
Reinventing yourself without losing yourself—how to pursue big goals, accept failure, and detach identity from outcomes. Sophia Amoruso reflects on Nasty Gal’s rise/fall, public scrutiny, leadership lessons, and choosing misalignment-free success (including walking away from “successful” paths). She also shares advice for early-stage founders on execution over perfection and when (not) to take investors, plus what she looks for in VC pitches.
Guest background
Sophia Amoruso is founder of Nasty Gal and the original “Girlboss.” She later became an investor/entrepreneur via Trust Fund and Business Class. She experienced Nasty Gal’s collapse after public attention, a Netflix adaptation of her life, and leadership challenges.
Key claims
“Doing it and failing” beats “navel gazing.” Identity isn’t tied to what you do. Leadership requires holding people accountable and knowing job descriptions. Most founders don’t need investors; build a minimum viable product and don’t over-announce plans.
Notable examples
Nasty Gal fell apart around late 2016; Netflix Girlboss headlines criticized the source. She took money off the table after raising $50M (selling 20%). She stepped off the board before Nasty Gal’s chapter 11; the IP was sold to Boohoo UK.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOSophia's Journey and Identity
3:32 to 6:17
Sophia discusses her life experiences and how they shaped her identity beyond her business.
“So Sophia, you made an Instagram post where you took stock of your life and I love how you ended it.”
Public Scrutiny and Women's Fear
6:17 to 9:05
The conversation delves into the challenges women face with public scrutiny and success.
“If anything, it would be like easier to accomplish less.”
Lessons on Leadership from Sophia
9:05 to 13:00
Sophia shares insights on leadership learned through her entrepreneurial journey.
“It's in my DMS and it's, and it, and it happened, you know, wrote that book in 2013, came out in 2014.”
Financial Freedom and Business Growth
13:00 to 14:00
Sophia reflects on her growth and financial strategies that led to her freedom.
“What do you look back on and wish you would have done differently?”
Lessons in Leadership and Accountability
14:00 to 15:44
Learn about the importance of accountability and leadership in business.
“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.”
The Impact of Venture Capital
15:44 to 17:49
Explore the effects of accepting venture capital on business ownership and profitability.
“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.”
Building a Business Without Investors
17:49 to 21:28
Discover why many businesses succeed without external investors.
“But most of the businesses, you know, 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.”
Trusting Others and Leadership Challenges
21:28 to 24:15
Understand the complexities of trust in leadership and team dynamics.
“And, you know, this stage of my life where I'm like, I'm free.”
The Journey of Selling a Business
24:15 to 28:00
Hear about the emotional and practical aspects of selling a business.
“Because I think a lot of people are like really callous, shitty leaders.”
Reflecting on Nasty Gal's Journey
28:00 to 29:10
Sophia discusses the challenges she faced while stepping back from Nasty Gal.
“for letting this go because if this thing is your baby how do you let that go and accept what's happening, but also is accepting that you're not the hundred percent owner of it anymore.”
Show all 21 chapters
Redefining Success in Business
29:10 to 31:50
Exploring the idea that success isn't just about scale, but also personal fulfillment.
“I hired a CEO for the last two years of the business.”
The Trade-Offs of Business Growth
31:50 to 34:20
Sophia shares the sacrifices required for business growth and her current priorities.
“It's like you can have, software gives you so much leverage to have like a really healthy business without a ton of people.”
Navigating the Podcasting Landscape
34:20 to 36:18
Discussion about the challenges of producing quality content in the podcasting world.
“Like I knew that the moment the light went out and I was just like, fuck, okay.”
Fear of Losing the Financial Feminist Impact
36:18 to 37:42
Sophia expresses her desire to avoid pitfalls that impacted the Girlboss movement.
“like right if my mental health is better is it suffering right if this is what you want to do it's not suffering right you know if you do you don't want to do you're suffering Yep.”
The Legacy of Girlboss
39:21 to 40:23
Sophia reflects on the impact and evolution of the Girlboss movement and its cultural significance.
“One thing nobody tells you about running a business, it's not the big decisions that exhaust you.”
The Legacy of Girlboss
40:27 to 42:04
Sophia reflects on the impact and evolution of the Girlboss movement and its cultural significance.
“And these digital platforms were just emerging.”
The Evolution of Girlboss and Feminism
42:04 to 54:49
Explore how the concept of 'Girlboss' transformed and its impact on feminism.
“And it's like, it was a fucking pink book.”
The Evolution of Girlboss and Feminism
54:54 to 55:59
Explore how the concept of 'Girlboss' transformed and its impact on feminism.
“Built for every industry, ready for every boardroom, netsuite.ai slash ffpod.”
Exploring Business Class and Its Impact
56:04 to 1:00:05
Learn about Sophia Amoruso's online course Business Class and its transformative effects on entrepreneurs.
“I love what you're doing with business class.”
Overcoming Challenges and Finding Perspective
1:00:05 to 1:02:00
Discover insights on navigating feelings of scarcity and survival mode while pursuing personal growth.
“I mean, if we're doing it for the plot, it's, it's a great plot point.”
Concluding Thoughts and Final Reflections
1:02:00 to 1:02:41
Hear the final reflections from Tori and Sophia, emphasizing the importance of impact and community.
“Uh, what else do you want to plug my friend?”
Transcript
Automatic transcript. May contain errors.0:00Tiffany Aliche: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 Hashtag Girlboss. 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.
0:32Being yourself gives other people permission to be themselves. Taking like big swings gives other women the opportunity to do the same thing.
0:40Tiffany Aliche: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 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.
1:10Tiffany Aliche: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 going to 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 gonna 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.
1:48Tiffany Aliche: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. This episode is sponsored by Squarespace, and we've appreciated their support of the Financial Feminist Podcast since 2021, the first season of the show. And we appreciate you supporting them too, because they are my default recommended website platform. You can offer services on Squarespace.
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3:48Tiffany Aliche: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 shit, 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.
4:27And then 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 hardest part of it all, there's a lot of hard things that happened this year. My husband that like left me right, you know, earlier in 2016 was when the 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 like realized that, you know, 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.
5:06Obviously, like 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, 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.
5:33Tiffany Aliche: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 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.
6:17Yeah, I think so. If anything, it 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, do you guys talk about trad wife stuff on this podcast? We do. We do. Unfortunately, that's a whole nother, I don't want to like devolve the conversation from the first five minutes into that. I'm like, so curious.
6:42Tiffany Aliche: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. 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.
7:29Tiffany Aliche: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 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.
8:22And when you fuck up, honestly, like they fall, 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 said and I'm just like I just want to be I want to 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.
9:04But like the, the big, the thing that people will remember and the thing that people's changes people's lives is like in your DMS, right? It's in my DMS and it's, and it, and it happened, you know, wrote that book in 2013, came out in 2014. And, you know, it's like the long tail effect of, of doing something that inspires people is like, it's worth, it's like worth every minute of it.
9:31Tiffany Aliche: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 MBA could? Yeah. Well, I think, you know, MBA, 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 MBA. There have been many times I wish I had an MBA.
10:07I certainly think that if you don't have an MBA, you, it would be helpful to work for someone else. Just 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 and 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.
10:41And 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 nasty y 'all didn't work out after 10 years. I mean, not a lot of things work out forever. Um, but in the beginning, like, you know, doing the job is the most important.
11:17And I think even for startup founders, people of 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 going to have a really hard time holding people accountable because you don't even know what the jobs are to be done.
11:33Tiffany Aliche: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.
12:06I think it's 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. One word of advice is just like, don't tell people what you're going to do.
12:35Just 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.
12:57Tiffany Aliche: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. You know, 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 um I mean candidly I had Google like what is what does a CPO CFO do like those are those are things that like I don't know what their job descriptions actually entail.
13:51And 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? 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 20, 30 year careers doing what they were doing and they still needed to be one told what to do.
14:26And then I had to check in and make sure nobody checked in with me. You know, 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 sold, I owned 100 % of the company.
15:06So 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 going to like, you know, whatever. And my advice often is just like, take the money because you don't know what's going to happen.
15:29Tiffany Aliche: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, 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. 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.
16:15And 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 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 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. And other ones are going to knock it out of the park.
16:53Tiffany Aliche:So you said that you didn't need the VC. is it a simplified question to just 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 going to be scrappy and i'm going to 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.
17:34And then even once you've built something, like 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, you know, 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 recommend against it for most people. Yeah. When I raised$50 million, I sold 20 % of the company.
18:14And so I controlled the board. I, you know, 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 yeah i heard boards were like a nightmare so i was like i don't want it to be complicated i'll just it wasn't like because i was controlling i didn't even know what i was controlling um but it was like oh okay cool we can like supercharge the business we can grow it faster and hire like the best creative director and have like the best creative and And, you know, it was awesome building out a world-class team, like really, truly world-class talent.
18:52And 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 just because, like, I could and there was not a huge, from my perspective at the time, you know, there wasn't a huge tradeoff. 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 dollar a year business.
19:25I was like, OK, 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, you know, holding talent accountable, it's a lot more than, you know, just getting good talent on board. there's a bigger job that's yours to knit everything together and make sure that that it all works and keeps moving the direction that everybody wants it to.
19:54Tiffany Aliche: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 know that we need people, we need support as women entrepreneurs in order to grow what we're trying to grow.
20:36I 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. Right. So it's like, it's really hard to vet up front. 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.
21:13And 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 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.
21:50Tiffany Aliche: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. 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.
22:38Tiffany Aliche: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.
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23:15I think that's what I want to prevent you know 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 mean I try to think about like betrayal like that's not a theme in my life I'm not like a litigious person sure like nobody's really really like fucked me over so you know the number of people that have come in and out of my life, hundreds of employees and 50, 60, whatever million dollars and, you know, million dollars with talent and really smart people. Like 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.
24:02And most of them, most people like intend, well, they want to do a good job. yeah sometimes it's just not a match but then they're the people who like really just like will not accept that they are blowing it and if they do blow it they're angry and they're like you know i mean i've had people just be like you know it's it's you right and when you're a an empathetic person who's always like trying to learn and and not the kind of leader who's like whatever i'm right all the time like 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.
24:41Because I think a lot of people are like really callous, 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 such a tough one.
24:58Tiffany Aliche: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.
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27:47Tiffany Aliche:when you think about selling the company do you feel like you had people that made you believe you had to like keep caring for it like was there a sense of like 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 is accepting that you're not the hundred percent owner of it anymore. 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. There was a bunch there, you know, I turned down a 400 plus million dollar offer from an outfitter of urban clothing.
28:33And when I owned 80 % of the company and, And, you know, I have that piece. I have it in my Dropbox. Like I have red lines. Like I still have it. Yeah. And, you know, before, you know, company doesn't go bankrupt overnight. There was a series of Hail Marys and like acquisition offers. But also like meddling and new investors came in. And at that point I really was kind of, I mean, I've been out of my league for a long time. The girl boss thing happened. I was traveling a lot. You know, 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.
29:13I 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. The intellectual property was sold to Boohoo here in the UK. okay but like I've been through so much I put 10 years in like at what point am I can I like protect myself and give myself what I need to just like get get through this and keep going I don't think it was like the best example of leadership but there's you know a certain point where you need to preserve yourself and you're gonna disappoint you're gonna disappoint other people no matter what but I think I probably disappointed a lot of people doing that for me when the company, when I left the company, um, it, it's, it was devastating, but it wasn't a surprise.
30:24And 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 like, Oh my God, this is, you know, the successful thing and all this attention and whatever it is, but it was like, it's a lot. It's a lot, you know, 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 kind of off topic, I inspired a lot of people, go big, whatever.
31:05And 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 you know i need a big team and this thing has to be this successful it's like i need magazine So you can have like a really awesome, you know, profitable, manageable business. And you get to go home at the end of the day to certain extent.
31:46I mean, you know, run a business. It's not, you know, 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, software gives 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.
32:08Tiffany Aliche: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 a year. 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 gonna sell out arenas and I'm gonna yeah covers of magazines and I'm gonna 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.
32:57Tiffany Aliche: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 Calibre 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. It's true. I mean, this is why I don't have a podcast right now.
33:37Like 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 like someone would be in London who, you know, is only going to be here for two days yeah i booked it two months ago yeah and now i have to be in london this week because i'm interviewing somebody on a podcast and i'm like you know it's like you can do yours remotely a lot of people do theirs in person and so it's like you know with everything that you do just think about like 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
34:32Tiffany Aliche:went out like my light and my my you know the office in my in my house just went out you know and it's like do your listeners care uh you don't think it will no it's this is on if you're watching on 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, is actually, that's a perfect example of like, um, we could have the most interesting conversation in the world that is super impactful. That is, you know, very valuable. That is very vulnerable.
35:07Tiffany Aliche:And there's going to be some people who hear it and listen to it and respond to it. And that's great. And, uh, but you're fighting against algorithms. You're fighting against, you know, 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 a forest, doesn't make a sound like, 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 um 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 uh 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 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 it's like suffers like it could always be better right like you can always do more so it's like is it suffering like what you're like right if my mental health is better is it suffering right if this is what you want to do it's not suffering right you know if you do you don't want to do you're suffering Yep.
36:29Like if your goals are in line with your ambition, then nobody suffers.
36:34Tiffany Aliche:Yeah, totally.
37:04Tiffany Aliche: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 yeah i know that there was parts of you know girl boss 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 have been different if it was definitely would have been different if it was you know in 2025 however that 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.
37:59Tiffany Aliche: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.
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40:34i mean it you can't control i mean you can only hope that what you create becomes part of the zeitgeist like you create something and you and you give it away and when girl boss like you know took off and like people called it a movement and like 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 girl boss 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, you know, non-college at all educated girl starting on like a digital resale marketplace and building something as sizable as I did.
41:18And so, you know, the impact of Girlboss 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 um i know i think like a journalist told me that i didn't i didn't know it until like pretty recently it might have been like two years ago or something um 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 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 yeah i mean the reason it became satirical is the same reason that ambitious women get taken down yes like that was going to be my next question for you yeah yeah so 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.
42:46And 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, I don't, it's like a pink book I wrote when I was 28. Like, I don't take myself that seriously.
42:58so I don't really like I don't know I don't know that was like that's like not 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 like 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 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 like, you know, is no longer yours and they can take and do what they want with.
43:39And when Girlboss was the thing and super inspiring, like 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.
44:12Tiffany Aliche:Yeah. Oh, I want to cry in a good way. I'm just like, um, that's a, again, I hate to use the word mature, but it's like a very, like, it's a very wise response. Um, 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 it's like, are you Sophia Maruso? Oh my God. I read all your books. Like I'm so inspired by what you've done, which i get i get all the time too that's what you go home yeah exactly like totally 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 doing all kinds of other dumb bullshit but so long ago i'm thinking about like you i don't know what like uk taxes or something right right right like you know how small my apartment is and what I'm going to do with three poodles like that's not what you know yeah 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 um Katie from money with Katie but we talked about like it it is uh this societal pandemic that when a successful woman becomes successful or when a woman becomes successful, it's, it's so easy to take her down.
45:41Tiffany Aliche: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, like, 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 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.
46:25Yeah. Can you think of any like brilliant women who are assholes who will remember, who are like just brilliant and it doesn't matter that they were an asshole like brilliant and like iconic but they're not i mean there's the one we brought up was martha stewart but like she
46:41Tiffany Aliche:literally went to jail so it's like and went to jail for something that wasn't insider trading but which again proves the point which is like you can be brilliant and quote unquote 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 allotted for very different for the same it would be like it would be like unfair right 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 uh show up which is so shitty and again if i'm somebody listening uh who wants to be a business owner who wants to put myself out there um 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 like i have to believe it's like like look at the impact like it's the impact it's like you know again like not not everybody's gonna like what you do and like i'm not the thing that i wrote in 2013 totally but like the impact of this thing that i cast out into the world and like gave to people to do whatever the fuck they wanted with is not me yeah you know it continues to make an impact and if you're gonna be egotistical about it it's like suck it like it's still impactful and people are still fucking talking about it when i blew it people like 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 like a way better story than being that person that just fucking navel gazes.
48:20Tiffany Aliche:Sophia's 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 I have to put on sale. I've got like a fucking decades of wisdom that I get to sell at a hundred percent margin for the rest of my life. Like 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?
49:11I mean, I can tell you what I look for.
49:15Tiffany Aliche:Yeah, great. a founder, I look for someone who's 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, I mean, you know, then the next thing is like, 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 kind of engineering or brought a product to market that is in the same kind of like realm that you know or industry that you know 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 like done nothing.
50:14I invest in founders that just have a deck. Okay. And like two of the best companies in the fund are the companies that hadn't built anything. They're the ones that have like 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 problem that's not just your own and be able to I guess articulate what it is that you that you plan to build how it's going to make money yeah um 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 what does that mean talk about I don't want to talk about that like I did that kind of like I you know my second business was girl boss it was media company and we had huge conferences whatever delivery and 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 yeah what do you feel like
51:43Tiffany Aliche:successful entrepreneurs know that the rest of us don't like what's a successful entrepreneur art um well maybe that's that's a good first question what your definition of success has clearly changed so has mine so yeah maybe it's is it traits of like i mean i i think just listening to your story one is like knowing what you actually want and knowing that that changes i think even in the 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, it took a really long time.
52:27And it took doing it to figure out that I didn't want to do all those things, you know? 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, you know, it's like, if you can tolerate working like really hard and not burn out and be miserable and you're having fun and you're learning and it's working out and like, that is the most fun path to go down. You know, 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. What is successful? I mean, I think it's they like persevere, like they just keep going.
53:05They'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 like that keep going that are that are more successful than the rest of us.
53:32Tiffany Aliche: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.
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54:25Tiffany Aliche:And if you have a question, you can just ask and it'll help come up with the answer for you. NetSuite is customized for a variety of industries. So it supports the way that your business truly works. And it's one of those things I'm so excited to continue investing in as we grow HFK and as we continue solving new problems in our business. For the first time ever, you can try NetSuite Next for free. If your revenues are at least in the seven figures, go to netsuite.ai.ffpod. Built for every industry, ready for every boardroom, netsuite.ai slash ffpod. One thing nobody tells you about running a business, it's not the big decisions that exhaust you.
55:06Tiffany Aliche:It's all the tiny pieces of information you're constantly trying to hold on to. A conversation with a client, feedback from your team, an idea that comes up during a strategy session, the next step you promised to follow up on. Individually, none of those things feel like a lot, but together, they're exhausting. For years, I thought I just needed a memory. Turns out I needed a better system. That's why I've been using the Plod note pin. During our leadership retreat at Her First Hunter K, we spent entire days talking about the future of the business. And instead of trying to write everything down while also participating in the conversation, Plod captures it for me with everyone's consent.
55:40Tiffany Aliche:Afterwards, I get summaries, action items, searchable transcripts, and the ability to ask questions about past conversations and get answers back in seconds. No more digging through notebooks, no more searching slack, no more wondering, wait, what did we decide? Honestly, it's one of those tools that truly makes me feel like I have a better operating system for my business. If you've been curious about it, this is probably the best time to try it. Go to plaud.ai slash ffpod for 10 % off. That's p-l-a-u-d dot a-i slash ffpod.
56:11Tiffany Aliche:I love what you're doing with business class. I truly don't know anybody who's as good at branding as you. 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.
56:52You know, I'd been doing like, you know, a media company and conferences and had, you know, 25 people at my second company was like, I can do this like super nimbly. You know, what's this thing called Kajabi? Okay. Email marketing automations. I mean, I understood marketing and I understood, you know, 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 know, you can't hear the branding on this podcast or see it, but it's aviation themed.
57:30So 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, like 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.
58:19Even if it's like your friends and family and grandma talk about mapping your competition. Then we talk about marketing and earned, owned, paid, and, 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 like 300 pages of worksheets. We do weekly co-working sessions and have different hosts. And sometimes I interview people. That's like exclusive to the community. And so there's something called the lounge, which is our digital community with 3 ,500 entrepreneurs in there.
59:02And everyone's just kind of 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 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 like, you know, zero to, you know, selling out in the first few weeks. You know, 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 a select few that I think can build like a billion-dollar business, really.
59:42But 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 are shooting for the stars and might actually land and stay there.
1:00:06Tiffany Aliche: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 um just like everything changes like you're just not going to be there forever yeah like 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 like the hardship you're experiencing now you might even laugh at in a year you know so like have perspective you know and you've asked me a lot of questions that you know you're like i would be bitter you know it's like 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, you know, less interesting to me than being like, ha ha.
1:01:03No, you're so right. I mean, if we're doing it for the plot, it's, 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
1:01:34Tiffany Aliche: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 public scrutiny like whatever yeah even if you don't end up doing the thing thing you said you're going to do, it can all work out. Yeah, totally. You know, even if it falls apart, it can all work out. Yep. Nope. It's so wise. Um, thank you. Thank you for being here. Business class. Uh, what else do you want to plug my friend?
1:02:09Trust fund, my venture fund, if you're, you know, going to go build the next Uber or something, um, businessclass.co. I don't No, yeah, no, I really, I've watched your career and, you know, 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.
1:02:37Tiffany Aliche: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, sophiaamaruso.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 to spark a conversation, these two things are the best things you can do to help support this show.
1:03:08Tiffany Aliche: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 slash quiz for a free personalized money plan.
1:03:42Tiffany Aliche:Financial Feminist is hosted by me, Tori Dunlap Produced by Kristen Fields and Tamisha Grant Research by Sarah Shortino Audio and video engineering by Alyssa Midcalf Marketing and operations by Karina Patel and Amanda Lefieux Special thanks to our team at Her First 100K Caitlin Sprinkle, Masha Baknikeva, Sasha Bonar, Ray Wong Elizabeth McCumber, Daryl Ann Ingman, Shelby Duclos, Megan 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.
1:04:29Should she say that about the kisses? Is that weird? She doesn't care. She presses send. This is the love story of real hinge couple Daniel and Roisin, written and read by me, Rufy Thorpe. Listen to the free audiobook now.
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From the publisher
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'll give you the crash course in reinvention you didn’t know you needed.
Sophia’s links:
Website: https://www.sophiaamoruso.com/
Business Class: https://www.businessclass.co/
To get more resources including any freebies mentioned in this episode, head to https://herfirst100k.com/ffpod
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