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Full transcript: Girlboss CEO Sophia Amoruso on Too Embarrassed to Ask

“Women, it feels like, are beginning to write our own history and our own version of what success can look like for ourselves.”

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Girlboss CEO Sophia Amoruso onstage at a Girlboss Rally Cindy Ord/Getty Images for Girlboss Media

On this episode of Too Embarrassed to Ask, the #girlboss herself, Sophia Amoruso, talks with Kara Swisher and Lauren Goode about launching a new company after her first company, Nasty Gal, filed for bankruptcy. Amoruso says Nasty Gal’s ambitions were right but that she made several “naive” mistakes about fundraising, hiring and her own interests and strengths as a leader.

You can read a write-up of the interview here or listen to the whole thing in the audio player above. Below, we’ve posted a lightly edited complete transcript of their conversation.

If you like this, be sure to subscribe to Too Embarrassed to Ask on Apple Podcasts, Spotify, Pocket Casts, Overcast or wherever you listen to podcasts.

Kara Swisher: Hi. I’m Kara Swisher, executive editor of Recode.

Lauren Goode: And I’m Lauren Goode, senior technology editor at The Verge.

KS: And you’re listening to Too Embarrassed to Ask, coming to you from the Vox Media podcast network. This is a show where we answer all of your embarrassing questions about consumer tech.

LG: It could be anything at all, like whether Kara Swisher will ever have a healthy relationship with her phone, which we discussed last week.

KS: We have a very ... it’s the best relationship I’ve ever had. But go ahead.

LG: I wonder how some people would feel about that.

KS: Send us your questions. Find us on Twitter. Tweet them to @Recode or to myself or to Lauren with the #tooembarrassed.

LG: We also have an email address, and we love your emails. It’s And, a friendly reminder, there are two Rs and two Ss in embarrassed. If you spell it wrong, we’re not gonna get your email.

KS: Exactly.

LG: So, Code Media wrapped up last week, but the content gods keep on giving, don’t they Kara?

KS: Yes they do.

LG: Isn’t that how media is supposed to work these days?

KS: Yes. Most of these are content. Lucas Shaw from Reuters just said that he was upset that I said, “We’re content makers to the core.”

LG: What are we supposed to say? “We’re journalists to the core”?

KS: Journalists. Whatever.

LG: We are journalists.

KS: We’re journalists. So much journalism. Don’t get on our case about that.

LG: But here’s thing, at an event like this, we do a lot of great journalism. And then we have to chop it up into all these tiny bits and distribute it and monetize it in any way we can.

KS: Right.

LG: Which is really just a long-winded way of saying that we’re still giving you interviews based on this conference. Because it’s a fantastic conference.

KS: Yeah. Exactly. We had a lot of people talking about various ways content is changing and journalism is changing and how people get their information — people from Facebook, theSkimm, 20th Century Fox, all kinds of things, talking about where media is going, which has always been changing, and then buffeted and shifted by the internet.

So, today on Too Embarrassed To Ask, we’re delighted to be joined by Sophia Amoruso, who is a Code Media attendee. And, as many of you know, we’ve been talking a lot to Code Media attendees for the podcast. Sophia was better known as the founder of Nasty Gal, an e-commerce company you may have heard of.

She’s also the author of a best-selling autobiography, #girlboss, which was turned into a Netflix series, though it was short-lived. I really liked the show. She’s had a lot of ups and downs in tech and media and commerce in a relatively short amount of time. And we’re gonna ask her about that and more on today’s show.

LG: That’s right. Sophia is also the founder of Girlboss Media, which is getting a new life and fresh funding breathed into it right now as Sophia looks to reinvent her company once again. So, we’re looking forward to asking her all about that. Sophia, welcome to the show.

Sophia Amoruso: Thanks for having me.

LG: Okay. Let’s talk about what’s new first with Girlboss Media, and then we’ll go into the lessons you’ve learned from your past experiences in your time as an entrepreneur, which we all know is dog years, basically. It’s a multiple.

Yeah. It’s been my whole life. I started Nasty Gal at 22. I like to say that this is the second brand that I’ve started on accident, but the first business that I’ve started on purpose. To do that after 10 years in the trenches, accidentally having a $30 million business before any venture capitalists even showed up to invest. And then, probably raising too much. Probably hiring too many people. A decade later, in the afterlife, it feels like I can’t be killed. It feels like a video game: I can be, but!

LG: The beginning of things is so exciting.

KS: But, you’re an entrepreneur. That happens a lot, doesn’t it?

Yeah. I am. I guess I’ve accepted the fact it is, and I didn’t really stop for a second before I got back up and kept going.

KS: But, explain ... we’re gonna get into your past, but let’s talk about what this is now. What is your latest venture?

Girlboss. And, we dropped the “media” just because the word media, what does it even mean anymore? We’re not doing a ton of journalism. We’re creating content for women about thought leadership. We really wanna be the leader in millennial about thought leadership for women and career resources and entrepreneur resources. Because, as someone who wrote this book four years ago, before so much has happened, and being an entrepreneur was cooler than being a rockstar.

I didn’t find myself in the business book section. I didn’t find the women who weren’t Sheryl Sandberg, who didn’t have the pedigree of education — I have no college education — who are doing things, who are starting businesses, who now have at their fingertips resources that I didn’t have when I started an eBay store, but I did have that resource.

And so, the internet has made it possible for those accidental entrepreneurs to have businesses. And then, the hairstylist becomes the founder of Drybar. The college dropout becomes the founder of Nasty Gal.

LG: So, in December, the Wall Street Journal reported that you’ve raised $3.1 million in funding from Lightspeed, also Slow Ventures, also Gary V., also Troy Carter’s company. It’s quite a list. And this idea of redefining success for women through bits of media. I’m curious what that media actually looks like. If you had to describe an emblematic piece of content right now, what would make Girlboss work? What is that?

I think one of the most highest-performing pieces of content for us was “I’m Depressed and Employed.” Like, here’s how I make it work, here’s how I talk to my employer about it. It’s just like having any other kind of illness. It’s just a mental illness. Other people don’t catch it when you bring it to the office, but it’s contagious in other ways and something that can really prevent us from doing great work.

LG: Was that a written post or video?

It was a written post. Yeah. We do primarily written editorial content. We have a series of videos right now that are behind the paywall that we’re calling Girlboss Academy. It’s like a paywall with a plugin built on a Squarespace website right now. I have an engineer starting in two weeks. She’s joining me from Tinder. And a product designer starting next week.

This is really a first for me in having control of our technology in a way where we can build something totally new. Typical media or publishing looks one way, and that’s what we do look like today. And then, e-commerce is like an out-of-the-box solution. You can’t really mess with it that much. I think what we have the opportunity to do is wide open.

KS: It’s interesting. Lydia Polgreen, who said in Huffington Post, she was talking about the same idea of service journalism, but not in the old traditional sense. A lot of old women-focused media — I’m thinking Cosmopolitan, Glamour, Cosmopolitan more than any of them — where that idea of, here’s what you do. Here’s the tips. Here’s how you get the most out of this.

It’s not to say that there’s nothing new under the sun, but you’re trying to create something where people can have a resource for a variety of things that they experience as a non-pedigree highly ...

Totally. Or, pedigree. I think that the voice is just really approachable. We’re not leaving anybody out. Our audience comes to us for resources. She comes to us to find out what ... We have a very active Facebook group, so some of what I’m talking about, it happens in this Facebook group. They’re gonna be asking one another to find out what kind of attorney they should talk to, to read an equity letter from an employer for the first time.

Or, they have three different options for a business name, like, “Let’s vote on which one you guys think is best.” Or, “Where can I connect in Nashville with Wi-Fi and an outlet to co-work all day if there is no co-working?” Or, “Is there co-working?” They’re traveling. They’re looking for recommendations to do their businesses, freelancing. The mobile digital nomad economy is very much at play. Many of our audience are freelancers. Fifty percent of the women that come to our conference ... We have two conferences.

KS: You do. You have two events. Mm-hmm.

Our next one’s April 28th in Los Angeles. It’s called The Girlboss Rally. Fifty percent of the women who attend that are business owners. A hundred percent of them, when we surveyed them, say that they want to be business owners ...

LG: How interesting.

... which is just so cool, and such an amazing audience to be creating content for. There’s nothing out there. As far as Cosmopolitan goes, they may be creating evergreen service content about what you should or shouldn’t do, but it’s coming, I think, largely from a place of ... God, I don’t wanna knock Cosmo. But, I think historically women have been ...

LG: Like you need to fix yourself?

Women have been spoken to in a way that is very fear-mongering, and like, “This is what you need to be to get this.”

KS: To get your man.

And we approach this future in this time where women, it feels like, are beginning to write our own history and our own version of what success can look like for ourselves individually; a conversation that we can have collectively as a group, and share ideas, learnings, wins, losses and hacks to define together what that means for us individually.

And that shouldn’t just incorporate work and money, because historically, this version of success that Forbes Magazine created, that men — old white men — created a long time ago, left the rest of us out. And so, what is this new world where we can redefine ourselves? We have these tools at our fingertips, and where women for the first time can think about how either section works and personalize.

KS: That’s right, because the definition of entrepreneur has not meant a young woman, essentially. That hasn’t, especially a young woman of color or anything else. Many of the tips may belong, maybe the tips that entrepreneur stories, do have a lot commonality. I’m thinking.

I was surprised. I just talked to Brit Morin, who was known for other things, more home and things like that. She just ran a cryptocurrency investing conference, which I thought was fascinating. She said she had 15,000 people, because most women are not involved in the current cryptocurrency [craze]. Four percent of the investors are women, which again, another great gold rush largely dominated by white men, which is interesting.

I was like, “Wow, that’s an interesting shift.” She’s like, “No it’s not.” To me, it was interesting that she’s moving in a different direction like that.

I think it is. I think a lot of people are moving in a direction of substance over ... or quality over quantity, especially in publishing. I think women’s publications have a lot of pressure to represent more than just what they have in the past, and to take a point of view on how they can serve their audience beyond inspiring them to look cute and smell good. I think that just raises all ships. I think it’s good for everybody, I think, everything that’s happening right now.

LG: Mm-hmm. It’s good to smell okay too. Kara, you smell okay.

KS: Thank you. I try not to! I make an effort not to smell good! But, there’s been a lot ... It’s really interesting. Lately, in the past month and a half, I’ve heard of at least six different women-focused media companies from various ages, various people and various backgrounds. It’s really an interesting thing, because there had been such a focus on how women should get information, and how it should not ... I think it’s part of the #MeToo movement. Something’s occurring where people feel they need to take control.

They all read #Girlboss. (laughter)

KS: What I’m speaking of, one of the interesting things about you is that, I’ll never forget interviewing you at the height of Nasty Gal. When your book came out, and we were in a bookstore. I think I said something to you that was, you didn’t mind but, was it was crosswise to the audience. It was a tough question about something. And I literally felt the crowd was gonna kill me. They were like these uber fans of yours. It was fascinating. It was almost religious. It felt like they were like, “How could you say that to Sophia!”

That word keeps coming up.

KS: Yeah.

Interesting, really.

KS: Yeah. Interesting. “Religious.” I’m not using the word “cult,” because that’s not the right word. But, they really ... it felt like you had a fan base that was very different than other media fan bases. It was an interesting experience.

Yeah. That was just right when the book was coming out.

KS: Right.

I like to say — I used to say at Nasty Gal — we had an ambitious customer, which is so weird for a fashion brand. But I think I was flattering myself in that, this is ambitious generation. These women have access to more than we ever have, like opportunity feels like it’s at our fingertips.

LG: And, the clothing styles were nonconformist, too. In some ways it would kinda make sense that that aesthetic would appeal to a certain generation of women who are just like, “I don’t really need to wear long skirts and pantyhose to the office.”

I think so. I mean, you think of me, and Nasty Gal ending up looking for the uninitiated, more like a 20-something-going-to-the-club brand. But Nasty Gal in its peak was a brand that made women feel like they could take on the world wearing what they liked and not necessarily fitting in.

It was always a part of ... The spirit of Nasty Gal was something I’m really proud of, but not something we necessarily owned or played up. I think that’s a dangerous thing in fashion to do. It’s kind of hard to have meaning when you’re running a fashion company. You’re always patting yourself on the back if you’re doing that. So, for our product to be our voice, when the voice was so integral to making Nasty Gal the brand it was.

KS: Today, it’s going to the voice.

Now, I’m just like, my voice is my inventory. This is great.

LG: You also planned additional hosting events. And, in addition to having what you call Girlboss Academy, which is an effective type of paywall, you’re also looking at different types of partnerships, I’ve read, and basically different ways to monetize your media content and not rely on crummy display ads all the time. I think I’ve also read that you’re looking at media advertising.

It seems like a lot of people in media are trying to move away from the crummy display ad model and do different reputable generation things. What area of that has you most excited right now, or do you see as being ...

I think it just feels like it’s wide open.

KS: Events is one. Right?

Events is one. But as far as working with brands — and brands having an appetite for something new, and the world being in a place where nobody really knows what works, and everybody wanting to invest in something that’s meaningful — Girlboss is really well-positioned. We will never have traditional display ads in traditional sizes. We just won’t.

I really admire the Outline. I think Josh Topolsky’s done an amazing thing, and I think their ad product is really beautiful. I have so much to learn about ad serving, tagging and all this stuff that’s totally new.

I think a really good example of how we work with brands is our partnership with Google. So, within the last year, along with Google, we’ve been able to work with Pinterest, L’Oreal, Cadillac, Amex, Equinox, Nike — the best brands in the world in our first year of business, on a Squarespace site, which feels like the emperor, I don’t know, the emperor does have clothes. But the emperor is still building her business, right?

And so with Google, we did something called The Startup Studio at the Girlboss Rally. We had a room of programming all day, and then built up this beautiful space that had our branding, but also incorporated some of Google’s colors. It was a beautiful room with 40 Chromebooks. Chromebooks was really the partner. We had workshops, hour-long workshops all day on everything from building a P&L in Google Sheets to learning how to market yourself to how to deal with email and manage your inbox effectively.

KS: You’re integrating the product ...

We integrated the product into that program at the event. And then, we’ve also distributed the videos of those workshops. After the event, the partnership extended into email, social. That’s one that didn’t touch the podcast, but we do custom podcasts as well. We just sold our first one. That will be launching in the next few months.

LG: What is that called?

It hasn’t been announced yet, but it’s a six- or eight-episode custom.

LG: On some topic, yeah.

On a topic that a brand completely owns. So it’s really just like a singular piece.

KS: It’s hard, because I’ve been brought a bunch of those, and I don’t wanna do that. It’s interesting.

I’m not gonna host it.

KS: Yeah.

The point of Girlboss is not to be the Sophia fan club. This is about building enterprise value and something that’s hopefully really lasting and lasts beyond me and this moment in time that is such a perfect time for Girlboss to be happening. I hope we’re building something that is much more lasting than the time that we’re in, which is such a perfect time and an incredible and important time for women. Something that extends beyond that and isn’t just necessarily riding that.

LG: What about merchandise? We had Taylor Lorenz from The Daily Beast on a couple weeks ago, and she talked about the YouTube culture and how a lot YouTubers, of course, like the millions and millions of followers and get millions of views, but they make a lot of their money off the merch.


LG: With that, Kara and I came up with an ad hoc merch strategy, which we’re trying to get Vox Media to buy it.

Oh yeah?

KS: We have no merch strategy. None. Zero.

LG: But you, obviously, that’s something you have a lot of experience in, right? So talk about how that fits into media companies. Do you think every media company should be looking at merchandising?

I don’t think every media company should be. I think Buzzfeed has done a really good job with Tasty, and I think it’s interesting as these companies grow, get huge, have to figure out to get huger, they’re realizing the power of brands. I think that Girlboss is a brand, which it gives us permission to transact in every which way. I’m not precious about how that looks in our future.

One thing I’ve learned is that focus is incredibly important and just such a challenge for me. And so, merchandise ... I mean, we have a few things on our website that was leftover merch from the last conference. It’s not gonna a big play for us, at least in the next year. If anything, it may be a licensed play. I don’t look forward to having physical inventory again, anytime soon. Maybe ever! But I think as a brand, we can plan a lot of different merchandise categories if we wanted to.

KS: All right. Let’s talk about that, about your experience, because you say you don’t want merchandise ever again. What did you learn? This is from Jason Del Rey, who is a reporter for Recode and editor of Recode. He covered your company, its ups and downs. “What did you learn about being a venture-backed company and taking money from VCs? How has that changed how you’re running this new company?” Maybe you need to go back in terms of what happened.

Gosh. When I raised for Nasty Gal, we were doing about $30 million a year. We thought we were on a runway to 130 million. We raised ... the first money in was out of Index growth funds.

KS: Right. I remember.

And, it was $40 million dollars in 2012. From there, the mandate was hire 100 people, grow by $100 million in the next year.

KS: Not easy.

We were just pulling numbers out of a hat. This is a time when I was meeting with Jeff Jordan from Andreessen, and he was passing on us, because was the pinnacle of e-commerce.

KS: I remember that.

It was such a different era. I think the best practices in eCommerce have come a long way since 2012. There’s a lot more executives with experience in e-commerce, because at the time I was hiring people who were either from a pure-play business that Bryan Lee might’ve started — ShoeDazzle — or someone who’s a veteran merchant who hasn’t really been in digital.

KS: Right, which is really different.

Finding the right leadership for Nasty Gal in the time that it came about was really challenging. And I was a young, naïve founder. I think I thought I could hire C-level executives who would just do their jobs, write their job description for themselves, hold themselves accountable. At the end of the day, I think scientifically, we’ve proven that an observed object behaves differently than when it’s not observed.

The same is the case for everybody. It doesn’t mean I lead the company now breathing down people’s necks. I have a firmer grasp today at the end of the day — the way the company spends its money, when the company becomes profitable, how ready we are for a series A. I’ve never raised a seed round before. I just did my first seed round after 10 years of entrepreneurship. All the things that I need to back into now, plan for, understand what my success metrics are that are actually reasonable and not just pulling numbers out of the sky.

KS: Yeah. You found they made things up. What a surprise.


LG: Because you feel like you were interviewing the VCs this time as much as they were grilling you about your business?

I think both. Yeah, I think both.

LG: What were you looking for in terms of looking for strategic partners and things like that?

I knew it was a bit of a party-round, so Lightspeed led, but everyone from Gary V to the founder of Product Hunt and Dribbble, and Troy Carter, Joe Marchese, Allen Debevoise, Bryan Lee and all these amazing people invested. I had this great network. I network anyway, but people who actually have had literal interest in this company doing well who know every brand that we might wanna work with, who know every suitor who may wanna acquire us, who know every other investor who may want to invest ...

KS: So, not as haphazard?

Much less haphazard. When I raised from Index — and I still love Danny Rimer. I’ve cried in front of him, and been back to Index’s offices, which is such a healing experience after losing so much of their money.

KS: It’s okay. They’ll get more.

We failed each other. I think we both agree on that. We both made some bad choices. But, when I raised from Index, I had read all these horror stories of boards just taking over. And I had this company where I was able to still own so much of it. I think I owned 80 percent after they invested 40 million. It was 350 post on a $30 million revenue at the time. It was just bonkers. How do you live up to that? Even if we hit a million dollars, that multiple is, in private equity standards, it’s like, what? You’re not turning a profit anymore?

Anyway, I chose this one investor because I was just like, I can have two seats and you can have one, and I’ll just control my empty seat. Less conversations, great. But at the end of the day I really do feel like having more people looking at the business ...

KS: Who holds everybody accountable.

... who don’t have competing priorities. It’s really important, and I do lean on our ...

KS: I do like that you feel that, because most male entrepreneurs who lose their money could give a fuck.

If Index ever invested again, it would be a coup. It would be so exciting. I just saw Damir and I was like, “Do you think Index would invest again?”

KS: Yeah. But at the same time, you feel badly. Very few entrepreneurs feel badly about any losses they go through.

I really try to keep my promises. I made a lot of mistakes along the way, and a promise can be hiring someone and getting excited about our beautiful future together. And then realizing, wrong person, wrong time.

KS: So, we’re here with Sophia Amoruso, the founder of Girlboss, and we have more questions for her. But first, we’re gonna take a quick break for a word from our sponsors. Lauren?

LG: #money #content.


KS: We’re back with Girlboss founder Sophia Amoruso who’s attending Code Media this week in Huntington Beach, California, where Lauren and I happen to be.

LG: We just talked a lot about Sophia’s current and future plans for her media company Girlboss, where she’s also the host of Girlboss Radio. We also wanted to ask her what she’s learned from her previous ventures and takeaways for other entrepreneurs who are trying to keep a startup alive. She has a lot of experience in that.

We’ve talked a little bit about Nasty Gal. We’ve talked about how your whole experience has changed your new approach to your new company. At one point, Nasty Gal was valued at ... how many millions of dollars was it valued at, 250 million you would say?

Nasty Gal?

LG: Yes.

At our peak, it was 350.

LG: 350 million. And at some point, you had to step back as CEO and file for bankruptcy.


LG: What happened there? What did you learn? What was the biggest takeaway you had from that?

I stepped down as CEO a year, a year and a half before Nasty Gal filed. That was a choice I made, because the day-to-day interactions, the CEO dropped, everyone was like, “Yeah! I wanna be a CEO.” Actually, I’m not really sure I wanna market that as a hope and dream for people, because it’s not that fun of a job.

LG: What wasn’t fun about it?

It was a lot of meetings with people who were amazing, but a lot of deliverables, deadlines, implementations, and just a lot of the guts of the organization. I’m really a creative at heart. I’m a brand leader. I’m a marketer. I know how to combine things that other people wouldn’t combine and to make something new.

I don’t think that at that stage when a company has a few hundred employees, that’s the job that I’ll want, even in this company. Maybe if I figure out someday I’ll hire an amazing Chief of Staffer. I don’t even know what I would need to do that job well. So I stepped down as the CEO, and promoted someone who was our chief product officer. At the time in our business, it was the chief merchandise officer into the CEO world. Sherry Waterson, who had run product at Lululemon, she was the CEO for the year and a half or so prior to the company filing.

LG: What happened, basically?

What happened? We raised at a 353 valuation when we were doing $30 million in revenue. Pulling numbers out of a hat. Hired 100 people. Spent a lot of money hiring 100 people. Got a really big office. Somebody signed a 500,000-square-foot fulfillment center space.

KS: You got ahead of yourselves.

Got a little bit ahead of ourselves. When you hire that many people that fast, there’s companies that do it and do it well. At Nasty, I felt like the Tower of Babel. I’ve said a lot about, and almost made it seem very sexy to start a company on accident. But the domino effect, or how you scale something that wasn’t organized to begin with, I think you can guess what that looks like.

KS: Was that the biggest lesson you learned as a manager, or just that you weren’t a manager, you were a creative? What was the lesson? If you had to give any of these people you’re giving advice to would say, what would be yours?

I think the lesson is, hire great people and, yes, trust them. But always know what their success metrics are. Know what your success metrics are and hold them accountable to it. Don’t be slow about course correcting.

LG: How much projection of the market you’re in do you think people should be doing?

Don’t raise at too high of an evaluation, because it really fucks you in the end. There’s less options for you. It’s great you own your company, but what does that mean if you’re too expensive to buy? We became valued in private equity multiples and not e-commerce multiples. E-commerce just became brilliant and sexy for several years. I think people are still a little hesitant to touch it, even though there’s a playbook and a lot of companies with these incredible brands that are launching and doing a good job.

KS: You also did a Netflix of Girlboss, which was a really good show, actually, but you had just one season there. Can you talk about that experience, because it was actually really good. Why did you do that? You were doing a lot of things all at once.

I know. Yeah. It was bit much. I mean, if Charlize Theron shows up and says, “I wanna do a show about your book, and we have a star writer who wrote ‘Pitch Perfect’ and ‘Pitch Perfect II’ ready to be a showrunner. And Ted Sarandos’ daughter read your book.”

LG: Ted Sarandos at Netflix?

Yeah. And, all of that conspires to get a yes from Netflix, I don’t know. I think you’d say yes.

KS: I think in your lifetime, if Forbes says they wanna put you on the cover even though you’re not sure what the next six months looks like for your company, you just say, yes. And, if they wanna make a show about your life, you just say, yes.

But all that happened in a year’s time. I was on the cover of Forbes. My marriage of a year went away. This guy bounced.

LG: Did he really bounce?

He bounced after a year. He was just like, “Never mind!”

LG: And then your company files for bankruptcy.

Oh, you release a book, and then you’re promoting in Australia at the same time your company is filing for bankruptcy. And then a Netflix show about your life 10 years ago comes out and tells people, a few months later, and tell everybody about the person you were 10 years ago and the company you used to work at while you’re in a new relationship trying to start a new business, trying to tell a new story but don’t even know what it is and haven’t processed. It’s just like, I’m pretty proud of not letting that affect me and just being like, “It’s a cool legend.”

KS: That’s a lot.

LG: You wrote when the show was canceled that you were proud of the work that everyone did but you were looking forward to controlling your narrative from here on out.

KS: What does that mean?

It was a real challenging time. I’d never seen, because I went on this crazy press story for my first book. I have never, and hopefully never again, experienced the amount of press that comes with a television show. TV is just like another beast. And so, given that the company had filed for Chapter 11 four months before the show came out, Nasty Gal was no longer, but here’s this show telling a story about a business that just became acquired out of bankruptcy by some people in the U.K.

KS: Were you relieved?

It’s really confusing to know who you are when people are like, “Is she actually like that girl on the show?” At a certain point, people have walked up to me and said, “Are you as rude as the girl on the show? You seem really nice.” I’m like, “Oh gosh!” I actually didn’t think the character was that awful, but that was some of the criticism. So yeah, it’s hard to have a character of yourself out marketing who you are, were or weren’t. At any stage, no matter what happened, or whether your company whatevered, it’s just really strange.

LG: It’s like the show was focused on your dumpster-diving shoplifting days when you were well beyond that at that point, and you had to watch that.

Yeah. It’s weird to have a story told about the last 10 years of your life when you’re starting a new chapter.

KS: Let’s finish up talking about the idea of success. You’ve been through a lot in a very short amount of time still. When you’re talking about defining success, what would you tell entrepreneurs right now looking into getting into the media business or the e-commerce business? I hate to do tips, but they do help.

At this stage in my life, be really buttoned up. Have an incredible brand, even if you have to pay someone to invent it — call Red Antler or whatever. Be really buttoned up. Find advisers who have an incredible network. I’ve just begun advising companies for the first time, which is really exciting because I have this amazing network of investors and advisers. That’s really, really important, because you can’t even get in the door to those meetings without those relationships.

Have, I don’t know, audacious aspirations. I think I put that we wanted to be “Oprah for millennials” and “Supreme with boobs” in our deck. I think that kind of, “Okay, this is big! This may be big.” We need to get into retail and things like that.

KS: How did that go over, “Supreme with boobs”?

It was fine. If a dude wrote it, I think it would not be fine.

KS: No. That’s true. That’s a fair point. That’s a very fair point.

Frank Goldberg cannot write that.

KS: No. Not at all.

LG: What advice would you give to female entrepreneurs specifically, especially given that we know the dismal numbers around female entrepreneurs. But not only female entrepreneurs, but getting investments from VCs and all of that. Is there anything specific you would say to female entrepreneurs?

Yeah. I’d just say, “Do it.” The more of us who do it, the more room there is for the rest of us. I’d say, “Don’t be a shrinking violet.”

LG: What does that mean, “Don’t be a shrinking violet?” What’s an example of how it happens?

Don’t sit on the side of the table. Lean into the conversation. Interrupt people if you have to. Don’t see yourself as the exception in the room. That goes for all kinds of people, not just women. If you’re seeing yourself from the point of view as someone who is other than, even if you are other than, there’s a psychic voodoo that you put on to the world that really can cause blocks for you.

So I just was like, I didn’t really consider that I had a vagina at any point when I entered a room. I think that is a position of privilege in that, I bootstrapped my company totally, totally different. Because a lot of women — and especially women of color — can’t even get into those conversations. But when you do, don’t operate from a place of fear or lack. Just operate from a place of power and whatever you need to do. If that is a power pose, or reading some Elizabeth Gilbert, whatever it is to get there, just get there and fake till you make it.

KS: Lastly, how do you look at the impact of ... are you figuring the MeToo movement into this? Now we have the MeToo Movement, and the backlash, and then the backlash to the backlash. Do you imagine it changing the equation? I don’t imagine it won’t change. I hope it will change.

Do you think it’s just a bunch of noise?

KS: I sometimes do, because it feels like I’ve been through it 90 times and the progress is so slow. I thought Ellen Pao would change things and it didn’t. I was hoping the Uber thing would change things and it didn’t quite.

I think change takes a really long time. I think we’re in this point, we’re ripping limb from flesh, and culture’s just totally fucked. There’s gonna be room to write something new.

I think, when I was in high school, the girl who was gonna go into college and become a sorority girl would never have gone to a women’s march. The women’s march is full of teenagers and full of young people. It’s not for people with hairy armpits and hairy legs. That was super fringe when I was 18 years old. I had hairy armpits and hairy legs. I wouldn’t let people open the door for me, which I now insist my boyfriend do, poor guy!

LG: Everybody!

KS: Everybody opens the door for Sophia!

The world is really different. If you didn’t choose a gender it was super weird, and I knew people like that who lived in anarchist houses in Seattle. But that’s a global, a huge conversation now.

KS: So, what do you imagine happening? What would you like to see happen? And what do you think will happen?

Oh God. Come on!

KS: I don’t know. Come on!

Fucking Nostradamus?

KS: Yes. You’re fucking Nostradamus! Thank you.

Is that why you have people on this podcast?

KS: Yes! That’s why I have you here!

What do I think the future holds?

KS: Yeah.

LG: You’re answering on behalf of all of us. You’re looking into your crystal ball.

I think that if Girlboss does its job well, does our job well, the future becomes a place where more women see opportunity, don’t see roadblocks, are met with open arms, are given a fair shot, are also honest with themselves about their shortcomings and don’t use that as an excuse for not getting to where they get. I think a lot of what needs to happen is the individual taking responsibility for themselves, and then in what they believe in. Hopefully, culture changes along with it.

KS: Yeah. I think we have to take everything by force.


KS: I think we have to not get ... People are talking about, you see a little bit of, maybe we should do the truth in reconciliation part. We’re at the truth part. And now we should reconcile. I don’t think we should reconcile at all.

LG: I think it has to be a two-pronged approach.

KS: No. I don’t think we should reconcile.

LG: But I like the idea of personal responsibility and owning too.

KS: Women always forgive. Now we can say, “Okay, now we can move on.” I don’t wanna move on until ...

No. I don’t think we’re gonna move on.

KS: That’s what I wonder.

Yeah. Time’s always gonna be up.

KS: Well, that is a good ending. All right, Sophia Amoruso at Girlboss Media. That’s the last question, because we did have one question from someone about the word “girl,” speaking of which. They didn’t like the word “girl.” I don’t mind it. Did you get a lot of push-back for using “girl”? Or is there a Womanboss?

Once in a while, people like to be really literal! So, if you were really literal, and didn’t do your homework, the word feminist would mean you think women are better, which is not really what it means.

No. That’s not what a feminist is. There’s lots of uncreative people who’ll take things super literally. Being a Girlboss is much more of a philosophy than it is a literal statement about being a woman who’s a boss. I think being a girl is coming from a place of wonder and room to grow. I don’t want dudes calling me a girl. But this is a company founded by a woman for women, and I don’t think that there’s anything offensive by saying Girlboss. Ladyboss sounds stupid. Womanboss sounds dumb. Vaginaboss isn’t gonna work. It’s a good brand name, and it’s working.

KS: Yep. I like it.

LG: Kara says Ladyboss.

KS: Ladyboss.


KS: All right then. I’ll start Ladyboss and see what happens!

Someone already did! There’s a whole industry of ...

KS: I think it’s a great name. Anyway, it’s been another great episode of Too Embarrassed to Ask. Sophia, thank you for joining us.

LG: Thank you so much for joining us.

Thanks for having me.

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