The Most successful female Entrepreneurs-Interview with Sophia Amoruso

The Founder of Girlboss Media talks about the ups and downs of starting her first company, NastyGal, and how she has been able to productize her unique attitude and sense of style.

Before GirlBoss was a book or a Netflix show or a hashtag, Sophia Amoruso was running NastyGal and reticent to even sit on stage and be interviewed. She finally relented, and this was one of the first she’d ever done.

This interview was situated almost exactly between a five-year, almost effortless success story of growth, and a five-year slog that ultimately ended in bankruptcy.

But while NastyGal ultimately didn’t work, Amoruso continues to find ways to productize her unique attitude, style and eye. In addition to executive producing the Netflix show based on her life, she’s recently launched a media company for women called GirlBoss Media.

I have mixed feelings on the show and the direction of her media company, as a woman who doesn’t particularly want to be called “a girlboss.” It’s possible I’m just not the demographic. I wasn’t the demographic of NastyGal either. Regardless, I’ve always respected Amoruso’s hustle and natural talent for building things. I’m not sure the show does it justice. I prefer the story in her words, before she became a feminist millennial icon.

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 You know, it’s interesting, I’ve covered Silicon Valley entrepreneurs for close to 15 years. They always have these stories about how alone and alienated they felt growing up. They’re kind of these stories where they were Anthony Michael Hall from “16 Candles.” They were just the nerdy, nerdy kid who didn’t have any friends, who no one liked.You seem so anti‑central casting of most tech entrepreneurs. In your own way you had a similar upbringing. You weren’t Anthony Michael Hall. You were a little more like Girl with the Dragon Tattoo.

Sophia Amoruso:  Yeah, I’m an only child. I grew up between San Diego and Sacramento, and we moved a fair amount. I’ve just from a very early age been pretty good at isolating myself and been in my own world in ways. I’ve fluctuated between the losers and the cool kids. I have always known how to survive in both groups.

I think that’s served me well in building a consumer brand to cool girls, but not being so cool that the ones who aren’t as cool as the cool girls can’t participate in.

One of the things I think is funny about you is here you’re a total capitalist, you’ve built a company that Forbes estimates is on a $130 million run, right? You’re one of the most promising up and coming companies in LA, you’ve raised $50 million in venture capital, and in your youth you were really quite the anarchist.

Sophia Amoruso: Oh, God, yeah, for a little while. That was another phase. I’ve always tried to find ways to escape whatever has been presented to me whether it was school and the bell that makes you go to the next place and being angry about being trained as a youth to move to different places based on the time that a bell rings. I think that’s a really depressing way to grow up. Unfortunately, that’s the way it happens.

I tried to find every way to escape joining the world that I was supposed to join at a certain age, and I figured out pretty early that it doesn’t work to not join that world in some capacity, then struggled with a bunch of different jobs.

I eventually found myself with the ultimate job of working by myself in a backyard selling stuff on eBay.

You have a lot of great stories about the shitty jobs that you had before Nasty Gal. Tell us about some of them.

Sophia Amoruso: I’ve done everything. I’ve scrubbed ring-around-the-collar off of men’s shirts and separated them by starch level. I’ve worked in bookstores and record stores and photo labs. I watered lawns for a while in some business park. I dragged the hoses and plugged them in and moved them around in wheelbarrows.

I never worked in restaurants, too many people, too much memory keeping. I’m not that organized. None of them last long, like six months. Most of them were about two weeks or four months.

Was that by your choice or someone else’s?

Sophia Amoruso: Usually my choice. I really didn’t get fired that much. I was really good at getting jobs, and I was pretty good at keeping them, but it was really hard to care about the ones that I didn’t care about, like selling $500 shoes to women in Pacific Heights, when I couldn’t afford a single pair of new shoes. It’s a really weird juxtaposition in places like that.

Working in a photo lab, I loved photography. That was exciting. I could run my film for free and sneak looks at other people’s photos, and that was great. They were all interesting in different ways.

Did you think that would just be your life, hopping between random jobs?

Sophia Amoruso: No. I was super miserable. Of course, you have to pay rent, and you try different things to figure out what works for you in the world. Some of those things I liked more than others, and I think all of those things, by trying so many different things at an early age, it allowed me to be a pretty experienced person by the age that I started Nasty Gal.

I think they all had a place in making me a well‑rounded person, in the same way that maybe college would have, had I had that kind of follow‑through.

Did you decide not to go to college or did you start and then leave?

Sophia Amoruso: I moved to Olympia, Washington when I was 17 and wanted to go to Evergreen, which is an interdisciplinary school, where you don’t actually do anything. You can major in Madonna. I’m not kidding.

I thought that would be so cool to study chaos theory and underwater basket weaving or something.

Minor in Madonna. You don’t want to major in Madonna. You’re not going to get a job with that, but maybe minor.

Sophia Amoruso: After a year of establishing residency in Washington State, I was now old enough, 18, to realize that that’s kind of a crock of shit, and that degree is probably not going to get me anywhere. I can learn that stuff on my own. I ended up taking community college classes in photography, and that’s really what I wanted to do and still what I really love and someday want to pursue on some level.

Beyond that, I took some general ed courses. I was fortunate enough to have parents who helped me for a little while figure it out, but weren’t like, “You need to take general ed classes.” I signed up full time for photo classes, and took a gemology class and a jazz history class, and scooted by until I ended up moving away and not going to school for a while.

It was never like a huge dream of mine. I would like to go back to school someday, because I think now I can make it my own, instead of this stepping stone to me being successful in the world.

I’m totally envious and respectful of people who have the drive, follow‑through, and long‑term thinking to spend four years in school, but I was a very impatient person at that age, so it just wasn’t for me.

Has that changed? Are you more patient now?

Sophia Amoruso: I’ve had to become more patient. When you start a business and you’re doing everything yourself, it’s instant gratification. You take a picture, you edit a photo, and you write something. You sell it, and there’s not that many variables. I sold 25 things a week, initially, on eBay.

You get to see the results of your work so immediately, and I got used to that for a really long time. That’s what fueled the business.

At a certain point, obviously, you have a much larger team. There’s a longer‑term plan and hiring people takes longer, because they’re harder to get or you have more specific needs for them. There’s specialists, rather than, “I’m going to hire someone to do everything and see how it works out.” There’s a lot of reasons why I’ve had to become more patient. It feels good. I think I have a long ways to go.

With all these different interests you had ‑‑ being a vegan, loving meat, being an anarchist, starting a company, admiring Madonna, then basket weaving, and then nothing, working the Fotomat and watering lawns ‑‑ were you always interested in fashion? Was that an undercurrent always…or was that, too, almost out of nowhere?

Sophia Amoruso: I’ve always loved clothes. I’ve always loved personal style. I always loved the way clothes fit and the silhouette of a human and clothes against that human. I was never a fashion freak, which I think is probably a disappointing thing for anyone to hear. I’ve been waiting for someone to ask me that in a setting like this, and I really have no other answer.

I love clothes. I think what has made the business successful is that I’m not a fashion freak, honestly. I like to have an eye and I like to apply that to everything. In the beginning, being creative was taking pictures, editing those photos, finding a model and exalting everything to this level that these things actually aren’t independent of one another.

Our brand has emerged from a necessity of my having to stop and listen to the customer and understand. I didn’t have bunch of money in the beginning to be like, “Hey, I’m going to tell this customer what she wants, and then I’m going to build.”

It was very much feeling it out, touch and go, and very iterative in that way.

How did you first start your eBay store? Were you someone who tended to be on the Internet very much? All the other things you describe doing seem more real‑world than virtual world.

Sophia Amoruso: My last job before this was in the lobby of an art school in San Francisco, checking student IDs. I was essentially a security guard, but their cheaper way of hiring a security guard. I just sat at the desk, checked student IDs, asked people to sign in if they didn’t have an ID, and told them what floor admissions was on.

I had enough down time to hang out on the Internet and whatever. Everyone was on MySpace at the time. I was getting friend requests from vintage eBay stores that were promoting their businesses on MySpace, and decided to check it out.

That’s really where I got the idea for selling vintage on eBay. I certainly didn’t invent it. I think it did it differently in some way and took it a lot further than anyone had.

I think that’s the mystery around your company. Everyone likes to tell this rags‑to‑riches story of you being this girl checking student IDs, and then putting stuff on eBay. Lo and behold, suddenly there’s a massive, multi‑hundred‑million‑dollar a year business.

But this is something people were doing since the dawn of eBay. When you saw other people doing it, who were advertising their businesses, did you think, “I can do that better?” or you just thought, “I can do that, too,” and yours was better?

Sophia Amoruso: I think I was one of those people that always thought I could do things better, but never figured out how. I’m a really competitive person. It was as much like, “Hey, I can do that,” as, “I think I can be more resourceful than them or maybe more creative,” or, “Instead of selling vintage in a really nostalgic way and making people look like they walked out of the 1960s or 1970s, style this stuff for the girl who’s actually buying it, who’s going to mix that with modern stuff.”

That wasn’t a big master plan. It was just with the resources that I had. It was very natural, what happened. I think the brand really emerged as an extension of my personality, not as much my taste level, but the spirit of the brand has encapsulated a lot of my personality and the things that I value, very unintentionally, and the name, also unintentional.

Do you feel almost saddled by the name? Or now are you successful enough that it doesn’t matter? I imagine the first time Forbes calls you to do a story, they’re like, “It’s called what?” I feel in every story, there’s a point where you have to explain the name. You must get sick of that.

Sophia Amoruso: It still happens. I went to a conference a month ago, and these people at the table were like, “Hmm‑hmm, I have my badge on. I’m going to be the one to break the ice. What’s Nasty Gal?” I’m just like, “Ugh.”

Would you have named it that again, knowing it was going to become this big?

Sophia Amoruso: Yeah. I wouldn’t have done this, if I had known it would become this big.

You wouldn’t have?

Sophia Amoruso:  I wouldn’t have known how. It would have not have worked the way that it worked.

What year was it that you started?

Sophia Amoruso: Late 2006.

When did it become lucrative enough that you could quit your other job?

Sophia Amoruso: I quit my other job before I started this.

Really?

Sophia Amoruso: Yeah.

You were like, “This is the full‑time job.”

Sophia Amoruso: Yeah, it started generating money from day one. I hated that job. I needed surgery. That’s why I got that job. I had no health insurance. I don’t know. It just worked.

Tell us how it scaled, though.

Sophia Amoruso: How it scaled? In the beginning, I sold some stuff that was mine, some stuff that I went out and found, figured out how to measure things and clip the measurements to the item and build an eBay listing template, and buy books about it, and all that really basic stuff.

Then figure out enough graphic design to create the first ‑‑ I don’t even know if you could call it a logo ‑‑ graphics. I was on eBay for a year and a half, until mid‑2008. It was a great place for me to learn.

I learned a lot about perceived value from watching things sell at auction. It was a great training ground as a buyer.

I got a little bit tired of sending all the traffic that I was cultivating in social media to this website that wouldn’t even let me own my customer. You scroll down at the bottom of any eBay listing, and you find, “Here’s your competitors, here are similar listings.” There’s a search bar at the top where you can leave.

Leave your store?

Sophia Amoruso: Yeah, leave my store. There’s a lot of opportunities to lose money on eBay, and to not really be able to control the experience. I’m really grateful to eBay for having given me a platform to start the business, obviously.

It was a natural step for me to launch a website. A lot of what’s worked with the business has been promises that I’ve made either myself or publicly to a customer, that I didn’t know before I initiated that process, what it would take to do that, but I was like, “Coming soon, nastygalvintage.com.” It was some way of getting the customer excited by telling them there was a website that was coming. Eventually, I figured out how to do that.

It was a big risk. There are built‑in customers finding you every day on eBay. They don’t let you capture those people’s email addresses or remarket to them in any way that isn’t super templatized.

I was very lucky that when I launched the website, there was some very serendipitous press that occurred because there were editors who were customers of mine on eBay, and they talked about it. It sold out.

I guess this was never the plan, but I had cultivated a large following on MySpace at the time, and told everyone on MySpace, “Hey, this is where you can go,” rerouted all the links on the MySpace page, and started posting different bulletins. People started coming to this other website.

What did you learn about social marketing in those early days? You probably didn’t call it social marketing. What do you think worked about that?

Sophia Amoruso: What’s always worked for us is just talking to people like they’re people. That’s what people are doing on social media. I think a lot of bigger businesses that are like, “Oh my gosh, we have this much money in our budget to invest in social media. We’ve been talking to the customer in this very luxury marketing way for 50 years. Now we have to figure out how to be transparent.”

I was a girl in a room with a keyboard and a MySpace profile. It was very easy for me to feel out how the customers wanted to be communicated with. It came naturally to me because that’s how I write. That’s how I talk. I wasn’t trained in writing creepy marketing messaging or whatever.

Before you could buy Facebook ads that were targeted to people who were fans of your competitors or of a certain demographic, I downloaded some illegal MySpace friending app, and was like, “I’m going to add all the friends of ‘Nylon’ magazine that are in LA, New York, Sydney, and Copenhagen, that are between the ages of this and this.”

I just pushed a button, and it would add those friends. It was free. That was a long time ago. It worked.

Other than getting someone to build a website, how did your business change when you moved off of eBay?

Sophia Amoruso: When you sell things at auction, you can do a 3‑day, or 7‑day, or 10‑day auctions, or you can do it at a fixed price and leave it on there until someone buys it. I did 10‑day auctions starting at $9.99 with no reserve.

There was 10 days where I knew that I wasn’t going to have to replace the stuff that was in the eBay store. That was nice. I would put it all in at once, people would bid on it, it would sell, I would put more stuff in.

When you have a website with 150, unique, one‑of‑a‑kind items, and you don’t have multiple sizes or any depth in inventory of those items, 150 people show up and buy them, and your store is empty. It takes a while to shoot that stuff, write a description about it.

I realized that as high as the margins were in vintage, and still are ‑‑ and I love vintage ‑‑ it was the next natural step for us to start carrying new designers and things where people who didn’t even understand what vintage is would stop asking me, “Do you have this in a small? Can you get another one of this?”

It’s like, “No, it’s vintage. There’s only one.”

For those people, and for my own peace of mind, we went to our first trade show. About a month after I launched the website, I had my first employee, Christina, who is still here. We started going to trade shows and showrooms.

Was she a friend of yours?

Sophia Amoruso: No. I put an ad on Craigslist, and she was the only person interviewed. I liked her, so I hired her. She was just awesome. She had worked at a boutique on Hyatt Street, worked with some of these vendors, and knew the ins and outs of that a little bit, which was really beneficial.

We explored that together and started buying stuff. Not everything worked in the beginning. It was like, “The new stuff is going to be kind of high‑end,” so we bought $300 dresses. Our customers were like, “No, I’m not buying this.”

We didn’t go out with a big, “This is our strategy.” It was, “I think maybe they are willing to pay that,” and learn, “Nope, actually, this is what our customer wants.” We felt everything out. We watched every order come through. We didn’t have an open to buy or something that said, “This is how many you sold.” It was, “Oh, I remember seeing…”

Literally, we would see the person’s name, and address, and the things that they bought, and over time registered, “These are things that are selling. Last week, we bought six. Let’s buy 12 this week. Remember that one sold out? Let’s buy 40.” Then 40 became 400.

Did it feel scary when that was ramping up? Did it feel like at some moment, this is going to end, or that jump between 40 to 80 isn’t going to work?

Sophia Amoruso: You always wonder if that’s going to happen, but I didn’t have anything to lose. There was no one breathing down my neck to tell me that I had to be successful. I’m good enough at that to make things happen, and was naive enough to just keep doing what I was doing.

You don’t see a lot of bootstrapped ecommerce companies. There’s a lot of laws of gravity with ecommerce. You’re shipping stuff. You’re holding inventory. When you’re going to trade shows, and you’re placing orders, there’s different capital needs.

How did you start to manage all that without investors?

Sophia Amoruso: I didn’t spend money on myself. I dumped all the profit back in the business. When you’re buying vintage stuff for years that it cost $5, $10, $15, $50 and you’re selling it for $100, $200, $1,000. I’ve bought things for $8 that I’ve sold for $1,000. That’s really good cash flow.

I didn’t know what that word even meant, but it looked really good in the bank.

I wouldn’t fly down to LA. I would stay with friends. I would drive my old‑ass Volvo down and back from the Bay Area, and all of those things made it a really cheap business to run. When you have one employee, or two, including myself, and there’s that much ‑‑ you’re growing 400 to 700 percent a year, every year ‑‑ those things, it wasn’t even a question.

You didn’t even use debt? It was strictly out of the cash you had just made off of sales?

Sophia Amoruso: Debit cards. I still have to beg for credit cards.

They don’t think you’re a good credit risk?

Sophia Amoruso: Amex is like, “We’ll give you a starter Amex, and then you can get the Amex that you want, because you’ve never had one.” Are you fucking kidding me? I’ve raised $50 million.

 All of this early phase of the company was being done in the Bay Area, which obviously is the biggest startup hub in the world, and yet you weren’t raising money. You weren’t running in those circles. Did you know any other entrepreneurs?

Sophia Amoruso: I started the business in San Francisco and then had it in Marin County for a couple of months and then I moved out to Pleasant Hill which is by Walnut Creek which is like an hour from San Francisco and an hour from all my friends.

When you’re 22 and you move out to the suburbs when that was the place you ran screaming from four years prior, that’s pretty intense, and I had nothing to do out there.

Why did you move there?

Sophia Amoruso: Because it was cheap, because I could park and go to the post office and not be accosted by bums.

We’ve left a litany of leases in our wake. It’s been from 1,000 square feet to 17,000 square feet to 75,000 square feet. I remember the day when I said, “We’re going to outgrow this,” and I was told by my long‑time trusted consultant, “Oh, you’re never going to outgrow this.”

A year later we were busting at the seams, moving to LA into 30,000 square feet, and that lasted a year, and now we’re in 500,000…I’m talking about fulfillment center space, but it’s been insane.

Yeah, we started in the Bay Area, but I did not know [the startup] world existed. My friends were broke in Oakland and in the Mission before the Mission became what The Mission is now, all the people with their layers and their iPods.

I saw people in San Francisco and I didn’t know what they did until recently. Now I get it. I go back there and I’m a part of that world, but when you’re not part of that world, it’s a very weird place to live.

How were you scaling, as a CEO, during that time?

Sophia Amoruso: Anything that I’ve ever wanted to learn I’ve Googled or YouTubed. I’ve YouTubed what the proper shelving for a warehouse is, because I’m not going to pay some consultant to pick out boxes for me or how to label things on a shelf. There’s free education all over the Internet.

If I’m worried about something or think I don’t understand it, there’s a lot of ways to learn about that stuff without going out and schmoozing and hoping someone answers your call. No matter how experienced or educated or awesome someone is, I’m always going to question the fact that they have one set of experience and what we’re doing is totally different from that. I always reduce things into having to find my own answers for them, and I’ve been pretty resourceful in doing that.

I’ve hired people who respect what I built before they joined the company. I was never desperate to keep anyone or so clueless that I had to believe every piece of advice that I was given, but I also hire people to trust them. I hire people, and I let them run.

What’s it been like since you guys did start getting a lot of press, now that you have funding, now that you’re high‑profile?

Sophia Amoruso: Mercenaries haven’t really made their way through our door. They have for interviews. [But] if you come to an interview and I’m like, “Why do you want to work for Nasty Gal?” and they’re like, “Well, I like to work for venture‑backed companies,” and that’s the first thing that comes out of their mouth…

I’m like, “I built this.” I owned 100 percent of the business until one year ago. That was five years after starting the business.

The venture capital piece is nice to have, but I’m very wary of people who are super‑excited to join a venture‑backed business specifically because it’s a venture‑backed business or the fact that women run the business.

It’s cool, women doing cool shit, but it’s not why we’re doing it. We’re not really patting ourselves on the back in some weird way over that. It’s not why we’re here. It’s fine. It’s a byproduct of awesome women who understand what the business is about coming to the table and having really great talent, but it’s not, in and of itself, any reason that someone should be joining the business.

Did you ever feel at any point along this journey, being a woman was a detriment in being successful?

Sophia Amoruso: No. I didn’t emerge from the corporate world, so I’ve never been a part of that. I’m sure there are reasons that these sentiments are out there, but I’m also not someone who hadn’t proven anything before I asked for, I didn’t even ask for venture capitalists to be involved.

I was like, “Yo, I did this. Do you want to play? Cool. I like you.”

Why did you decide you were going to take venture capital at this point?

Sophia Amoruso: Index had called for a while. A couple of other people had called and then they snoozed. They were like, “Oh, we want to invest in companies that are $10 million in revenue and bigger.” We went from $6 million to $30 million.

I’ve gotten everything that I’ve gotten by asking for it, from writing people on LinkedIn, from hassling people, from getting a no and saying yes, and this is why, and convincing people. That’s hustling.

There’s a lot of VCs that expect to be invited guests to the table and wait for you to open up your realm to them. That’s one way to do it if you want whoever to give you the highest valuation, but from you it was really like I had spent five years building something that I’ve very proud of that I want to be a legacy.

I’ve found a very rare fit in Danny Rimer of Index, who didn’t dance around anything, didn’t ask any stupid questions, just saw what I had built, really got it and trusted me and said, “Hey, let’s do this.” He leaned in.

You always talk about this personal connection with your customer. You talk about her, and this girl, and this customer. Do you have the same customer now that you did five years ago?

To the degree it’s been built off your aesthetic, over that period of time, you’ve probably changed a great deal. As you get bigger, does it worry you at all that the brand becomes more diluted, or that girl changes?

Sophia Amoruso: Yeah. I would like to grow with our customer. I think protecting the brand is really important because what’s made it successful, I want to honor at every opportunity in the future. I think it’s what’s going to make us successful in the future.

It’s important that we don’t alienate our customer. That’s a difficult thing in America as a corporation to continue to stay friends with our customer, which we always have been.

It’s a very high priority of mine, but it’s really hard to control all the moving pieces of a business with close to 300 hundred employees, and buying thousands of…I don’t even know if it’s tens of thousands or whatever SKUs throughout the year.

Making sure that’s all right, and every person who answers the phone is doing a good job, and no customer feels like they’re wrapped up in some really big machine.

On some level, a big company, that’s what it is. I think there are ways of humanizing that at every opportunity. That’s something that I’m interested in.

There’s one thing that you hate that other ecommerce companies do, according to our conversation last night. Celebrity endorsements.

Sophia Amoruso: OK. I don’t hate it. I just think it’s a very different way of having a successful business.

You went on like the most emotional rant about this last night.

Sophia Amoruso: I was drinking.

You were like, “It is so cynical and it is men’s attempt to try to act like a woman is telling other women what they can wear.”

I think what you said was, “Our customer does not read ‘People Magazine’ and if it does, it’s when she’s getting her nails done, and she’s not proud of it and she would never admit it and she would never buy anything a celebrity told her to buy.”

Sophia Amoruso: I hope our girl’s out there.

If someone were looking at you, what would you hope they were inspired by? What do you consider the thing you’re most proud of in having built this company?

Sophia Amoruso: I’m proud of having built this company without having any mercenary relationships and without having to be friends with people that I don’t like, or have investors who I know will help but actually annoy the shit out of me, or hire people because I know they’ll get the job done but, shit, I hate being in the same room with them.

I really think the people piece of this business is my greatest achievement, and that I want to be in the same room with people and that everyone is actually aligned on doing awesome shit, beyond being a retailer, beyond creating content or beyond buying stuff or designing stuff or shooting photos or whatever.

There is really a spirit inside the business and outside the business with the amazing customer that we have that is very unspoken that has just somehow emerged and just works. I feel very, very proud of that and very grateful to the people who continue to make that possible.