Our Cover Story With #Girlboss Sophia Amoruso


She got game.

An “anarchist misfit” and “unlikely businesswoman” is how entertainment directory IMDb describes the main character of Girlboss – the new Netflix comedy series that’s based on the life of Sophia Amoruso. And, it’s a pretty accurate description of this fashion entrepreneur.

An angst-ridden, dumpster-diving teen who, at the age of 22, started an eBay store in 2006 selling ‘pre-loved’ items (the first thing she ever sold on eBay was a shoplifted book), Sophia had never planned to go into e-commerce. Yet, she has managed to cram a lifetime’s worth of success (and challenges) into the past decade. That small eBay boutique turned into a bootstrapped e-tail fashion empire, Nasty Gal, and transformed the former op-shopper into a self-made millionaire – and superstar author.

She connected with customers over MySpace, scouted young models online and paid them with burgers. Her book, #Girlboss, became a New York Times sensation – and a social movement. Part memoir and part call to action, it documented her rise to the C-suite with unflinching advice for female leaders (one chapter is called ‘Money looks better in the bank than on your feet’).

In 2012, Nasty Gal leased a 45,000 square metre distribution centre and received US$40 million in investment funding. Three years later, Nasty Gal reportedly surpassed US$300 million in revenue, tripling sales in three years. It topped the list of 500 top e-commerce performers, beating Apple and Amazon with a 92.4 per cent five-year compound annual growth rate.

But in 2016, the same year Sophia’s marriage ended, Nasty Gal filed for bankruptcy. Revenue had been sharply dropping and Sophia, who had a 55 per cent stake in the company and stepped down from CEO to executive chair in 2015, described the decision as the most responsible option to prevent closure. In February 2017, after years of layoffs and lawsuits, the brand’s intellectual property was acquired by the UK fashion website Boohoo for just US$20 million. That same month, Sophia received a notification that she had been removed as an admin from the Facebook page of the company she had built with her bare hands. Nasty Gal continues to operate, but without Sophia’s involvement.

The rise and fall – and rise again – is all part of this entrepreneur’s journey and cultish likeability. A few months after the bankruptcy announcement, more than 500 women in Los Angeles came together for the Girlboss Rally, a day of talks and activations to inspire women to rise up and redefine success for themselves.

Far more than just a snappy book title, Girlboss Media is now a media company that enables women to connect across social, digital and experiential platforms to share knowledge about their careers, finance, relationships and businesses, and empower each other. To date, the #Girlboss Foundation has awarded more than US$120,000 in financial grants to women in the worlds of design, fashion, music and the arts to help fund their passion projects.

The femmepreneur, who overshares, swears, and isn’t afraid to be flawesome, has filled a gap, not only in what she does but how she does it. She’s a role model for leaders who don’t wear a power suit, play golf or conform. As Girlboss launches on Netflix to loosely retell her Nasty Gal journey, Sophia the businesswoman is redefining success in an era where career paths are rarely linear.

She recently sat down with Lisa Messenger to discuss it all.

Lisa Messenger: The last time we caught up was for dinner in Sydney, two days after you announced Nasty Gal’s bankruptcy. But I have to say, despite every hurdle, you are still an extraordinary woman and the ultimate Girlboss.

Sophia Amoruso: Wow, thank you, it’s been a ride, a real ride.

So how were things in retrospect?

It was terrifying when that was happening, because you don’t know whether the world is going to think you are a piece of sh*t or equate you to Donald Trump, because he went bankrupt, or disregard all the things that you accomplished over the last 10 years, or say that your book is total bullsh*t.

You’re so extraordinarily open about everything you’ve experienced…

It’s always scary to stumble publicly. What I’ve found with being open about it – and I think I can be a lot more open about it – it takes publishing a book to do it more completely; you can’t just dip in and out of something that’s so big and such a story I guess.

It’s complex.

Complex, yeah. Someone stumbling very publicly and pretty honestly, there’s not enough people doing that, I guess. We’re all flailing in different ways and stumbling in different ways, the rest of the world just doesn’t hear about it. But, to us, it feels like that’s all that’s happening. So to see someone who you may have thought had it ‘figured out’ totally start over is probably very refreshing, and puts your life
into perspective in some way.

You can only hope that the stuff you’re stressed out about today becomes stuff that [you] would laugh at two years from now. You find yourself growing and looking back and thinking, ‘Oh my god, I can’t believe how much energy I put into that thing’ that I had to learn or do. That experience that now feels like total child’s play. So I think that’s the goal.

Have you had a chance to take it all in?

It’s going to take me at least a year to process it all. Because I’m such an entrepreneur, I got right back up. I know that there’s such a window of opportunity [with] this Netflix series, and it’s a time in the world that needs great women in media. Not that I don’t plan on reflecting on what’s happened, it’s just that spending a year licking my wounds doesn’t sound like the smartest thing at 32-years-old right? It’s something I’m still digesting.

Like a Girlboss, you’ve really bounced forward rather than just bouncing back. What does that term mean to you now?

I used to say Girlboss is about being the boss of your own life. And it’s true, it’s about all the things in your life, it’s about being deliberate in not just your work and your goals and your personal finance, but in what you eat, how you live, how you travel and who you surround yourself with. It’s a very holistic thing.

[But] the goal of Girlboss [the company] is to re-frame this concept of success. I found myself on the cover of Forbes magazine, no happier per se. But that was never my goal. The concept of success being financial or something that has to do with your career, yes, that’s important… but success can mean a range of things. And the model of success today is something that is very much built on this vision of a bunch of white men. I don’t have the answer, but I’m asking the question, what is success?

I remember Forbes listed your net worth as US$280 million… 

I wish [laughs].

So what does success mean for you in this moment?

Right now, making sure that I’m tending to my personal life and not delegating that to a dog sitter or a house-keeper, and really spending time in my backyard. Seeing my friends beyond a catch-up or a brunch, that’s success. Nourishing my body, taking care of myself.

And then coming to work with amazing women who understand that there’s no right way, and that we are all learning together. What we do today becomes an anniversary tomorrow. So the processes we put in place to get the work done, and the conversation we have around how we work together and how to make that better, is something that, if we start that today, this can be a much better culture than the culture I built in my last company. So that’s success to me.

That, and being profitable. Not being in debt, having a healthy business – but not at all costs.

I love that, it sounds like getting the foundations right for a healthy build. What does Girlboss look like right now?

So last week I was sitting here with four other people, and today I’m sitting here with six other people. We have one writer in-house, an editor, we have a president in New York, who’s overseeing the revenue side of the business and seeing how we can partner with brands, one social producer, an art director, my assistant, an intern and an account manager. We’re just doing two stories a day, and we’re almost at three. Our traffic doubled month over month just because we started publishing more regularly and had the dedicated resources to actually push ‘publish’ on Facebook. We were writing stories but we weren’t even sharing every one of them – which does not drive traffic to your website.

You also have the Netflix show, Girlboss. How did it come about?

I wrote #Girlboss in 2014, so it will be almost three years to the date, because it came out May 6th of 2014. I work with WME [William Morris Endeavour agency], I have a literary agent there, and Charlize Theron got her hands on the book and loved it, and she has a production company called Denver and Delilah. It was kind of just like all the stars aligned, it wasn’t a difficult thing to put together. It definitely took a little while – Netflix is very picky – but that was a good two years ago probably. We were all there, we pitched Netflix and they loved it and it just went from there.

The show is just great – it’s funny and it’s self-deprecating. What’s it like trying to cast for yourself?

There was probably over 400 castings… seeing people try to play you is really interesting. Some people came in with wigs on and with sayings; it’s just pretty entertaining, I’ve got to say. And there were people who were well known, they came in and read, so just seeing that was fascinating. It was funny to have moved to LA six years ago and have no idea what all these people at coffee shops were doing; they are writing scripts, they are in-between castings, I’ve just never really seen the inside of how that side of town works. We started casting, and the first casting just had to be the character of Sophia, it’s just such an important role. She’s in almost every shot and almost every scene. So finding someone who had a great level of experience as an actor, who wasn’t a newbie, has been on set, who knew the ropes, and also wasn’t someone that had been branded in some other way, who was a bit, I don’t want to call Britt [Robertson, who plays Sophia in Girlboss] a blank canvas, but this is a very different role for her, so it was nice to work with someone who we could shape.

Is it hard for you looking back on that since you’ve kind of left Nasty Gal behind? Or is it an extraordinary legacy?

It’s always difficult to be in the public eye. I know that there are people who worked at a real company called Nasty Gal, who had different experiences, who may not understand that this is comedy and that this is fiction created from reality. So I’m hoping that everyone takes this show with a grain of salt and feels comfortable laughing at the last 10 years of my life and who I am. At this point, I have a pretty strong stomach lining, and have been through it in terms of the public eye and I just kind of take it as it comes.

It’s an amazing legacy, my parents are very proud and it’s an exciting opportunity to be an executive producer for the first time – something I’d like to do again, maybe not for a show that’s about my life. I just don’t take myself seriously enough to worry too much.

You seem to have just become stronger and stronger from telling your story as it unfolds. What do you feel like you’ve learnt over the last few years?

The biggest lesson I’ve learnt would be to grow thoughtfully. I was doing millions of dollars in revenue and people were like, ‘You’re going to be doing hundreds of millions’, or, ‘You’re going to be a billionaire.’ When you’re in your mid-twenties, early twenties, and people are telling you things like this, you think, ‘Cool, maybe that’s the goal, okay.’ It was a ride; you do your best with the experience and skills that you have at any given time. That was a company that I never really meant to start and then, halfway through, I was like, ‘Oh, this is a company’. With what I’m doing today [with Girlboss], I’m very intentionally starting something.

It’s so true, you have to mindfully set things up from the start.

I do believe in stumbling into opportunity but, at the same time, as early as you possibly can, organise yourself around it and what your goals are, and what kind of a culture you want to have with your team. I think that’s incredibly important. Nasty Gal, for the first few years, I was like, ‘I’m going to hire people that I like, and have good style.’ It was a fashion brand, so there was that piece to it. But I had no idea, I had never worked in a company.

What [else] did I learn? Building a company is really hard, when you’re in the role of CEO or you’re at the top, if things happen in your company, people expect you to know everything that’s happening, just because of your position. They think, ‘How could you let that happen?’ There’s often no opportunity for you to resolve those things, because you don’t know [about it]. So I want to figure out how to create a company where I’m not disconnected in that way. It’s very easy for executive leadership to be focused on really big things and not [go] deep with the team as much as they could be, and so that’s an opportunity.

How is starting a company different the second time around?

Being a second-time entrepreneur is really great because it’s not like, ‘What’s an employee handbook, what do I do?’, ‘How do I identify talent?’ I’m not perfect by any means, but this feels very different and it’s really nice.

This interview is an extract from Collective Hub Issue 45.

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