May 1, 2017 · 10 minutes

In the last week I’ve binge-watched and cringe-watched two anticipated new shows, both based on the work of people Pando has conducted long interviews with, and both women who I admire.

I’ve binge-watched Hulu’s The Handmaid’s Tale. I’ve cringe-watched Netflix’s Girl Boss.

Let me emphasize: The one that didn’t have me cringing was a slightly too-close-to-now world where women are stripped of all rights and a patriarchal society exerts total control over their uteruses; the one where a child was ripped out of her mother’s arms. The one instead that had me shaking my head and saying, “Why? Why? WHY?” was the navel-gazing dramatization of the life of Sophia Amoruso, founder of the new defunct NastyGal.

The latter show has been about as widely panned in the press as the Handmaid’s Tale has been lauded, so neither is my intention here. I am squarely not the audience for “#GirlBoss”, the book or the movie, nor was I the demographic for NastyGal. But that’s never kept me from admiring Amoruso and what she built even if ultimately it would all go belly up.

Even now, I admire her resilience. Failure of her business hasn’t stuck to her the way it does to a lot of ecommerce CEOs and a lot of female leaders. She is building a new media company for women. That’s the fourth time she has productized herself, if you count the clothing line, the book, and the Netflix show.

No one is that natural of a commodity. That takes work. She’s not at the Oprah and Martha Stewart level, but few women entrepreneurs have successfully been their own product in so many mediums. That takes talent. That takes individuality. It takes hustle. But it also takes restraint and judgement.

And here’s what the show about her gets so wrong. It captures the madcap and irreverent aspect of Amoruso but not her judgement, her discipline in teaching herself every aspect of her business, her caution. This is a woman who turned down venture capital repeatedly, before very cautiously trusting and giving a board seat to Danny Rimer. If raising too much capital and going for mass growth was part of NastyGal’s ultimate undoing, the reason she built it into a $100 million revenue business to begin with was that sense of caution.

I haven’t spoken to Amoruso in years. But I did one of the first on stage interviews with her ever at a 2012 PandoMonthly. It took months to talk her into it. She was very restrained in the interview, carefully picking her words on stage.

I knew getting her to open up would be a challenge. We’d had dinner the night before, and she was fixated on early IMs of Mark Zuckerberg that had been leaked as part of the Winklevoss case. She was worried about accidentally making a flippant remark that might be used against her and her business for the next decade or more. She was terrified of someone taking her words or actions out of context.

But it seems to me that’s exactly what she’s allowed Netflix to do just five years later.

None of that caution or restraint or judgement comes across in the character of Sophia, and that makes the show utterly unbelievable. Because it wasn’t her eye for vintage fashion that made NastyGal so powerful, and that’s really all that Sophia the character has.

Sophia the character is also an asshole. Not just an asshole, but the kind of asshole that Gen X folks like to tell themselves millennials are. She spends an entire episode agonizing over whether she should add her best friend back into her MySpace top eight, instead of a bunch of celebrities and brands like Oprah and Vogue.

Another episode revolves around trying to get a wedding dress to a bride just moments before she walks down the aisle. It’s only cut so close because Sophia wouldn’t overcome her fear of bridges and the courier service won’t drive it to Marin that late. Even in a pre-Uber world there are a million ways of solving this problem. Asking a friend, jumping in a taxi. Instead she gets wasted, passes out, misses the courier and has to run it over the bridge making it just in time. Her relief is very clearly not saving the wedding. It’s avoiding a negative rating on her eBay store.

I’ve spent a week thinking about this juxtaposition: How the same woman with an ascendant business at her back and everything in her favor was so paranoid about saying the wrong thing in a wonky startup interview that only a few thousand people would ever see…. How just a few years later that same woman executive produces a major Netflix drama that strips all of the best of her out of her character, just after her company has gone bankrupt, and she is hoping to relaunch her brand as an aspirational media company for young women.

She’s invited all the unkind things that people have mostly not said about her: That NastyGal was a fluke, that she was a shitty CEO, that she never deserved the success to begin with. It’s one thing to present as an accidental success when you are still successful. It’s a staggering risk when your company has gone bankrupt.

Put another way: Startup folks obsess over “the right way” to fail. This show doesn’t even show a “right way” to succeed.

Sure, she has said the character was only loosely based on her. But her name flashes on the screen as an executive producer. People took “The Social Network” to be the true story of Mark Zuckerberg, even though he had nothing to do with the book or the movie and it was widely fictionalized. Of course, people assume the character Sophia is at least a version of Sophia that Sophia herself is cool with.

And it’s not the only puzzling decision she’s made around her image recently. Buzzfeed put their finger on her dilemma in covering Amoruso’s March “Girlboss Rally” and the launch of her company Girlboss Media. She’s said the world needs women to collaborate more than ever post election, but explicitly doesn’t want this media company around women to appear in any way political. Huh?

From Buzzfeed:

Girlboss, though, has no plans to embrace politics in a significant way, Amoruso said. The company already has name recognition and Amoruso's loyal follower base (450,000 followers on Instagram alone) to get it going. But can it succeed without reflecting the tectonic shift the election wrought for its audience?

 

That depends on what happens to mainstream feminism next: whether it slides back into careerism, the place #Girlboss flourished, or whether it maintains the political urgency brought on by President Trump. And that means, once again, Amoruso has found herself at the center of feminism's evergreen identity crisis, a murky, tangled, infinite jungle she never intended to enter.

The story brilliantly captures a sort of stuck-in-time feminism that seems to have caught both Sheryl Sandberg and Amoruso by surprise. The “careerism” feminism was mostly an individual journey, and one that spoke to and worked best for married, educated, white women in Sandberg’s case or scrappy, DGAF young white women in Amoruso’s case. A few years ago, these women were comparatively radical for talking about their gender at all in the business world. Today, that kind of feminism is seen as part of the problem, when it comes to intersectionality and the fractured feminist movement of the past.

I recently saw a Tweet saying white women who are embracing feminism now need to start with explaining what took them so long. Women of color are pissed that only now we’re enraged, and I get it. I recently showed up here myself, and explain at length in my book what took me so long and why I’m not proud of my previous views on the subject. How does this world not change you if you’re worried about women’s issues, gay issues, transgender issues, race issues, immigration issues? How does a more radical world not make you more radicalized?

Strangely, while her message may be trapped in time, Amoruso’s audience has changed. The original NastyGal was more suicide girls than millennial pink. The original NastyGal wouldn’t have attended a Girlboss Rally, where the gift bag alone “worth the price of the ticket.”

So who is this loyal tribe anymore? It’s not the original NastyGal, nor is it the TeenVogue crowd. And professional women building companies-- the tribe Amoruso is now part of-- isn’t a fit either.

Again, contrast that to the Handmaid’s Tale: Something published 1985 that has proven not only timeless but an absolutely prescient feminist and political screed of the dangers of the world we are in right now.

Somehow Amoruso’s and Sandberg’s brand of feminism has becoming jarringly outdated, while Atwood’s is so timeless it has gained more relevance. This seems to come down to truth. The Handmaid’s Tale will always look prescient anytime a patriarchy gains strength, because its core truth is about patriarchy’s obsession with controlling women’s uteruses. That’s true in China where women were forced into having nine-month abortions, and that’s true in parts of America where Planned Parenthood is defunded citing the spectre of women having nine-month abortions. The two seem opposite. In reality, they are the same. Handmaid’s Tale is only a more extreme telling of that.

But Atwood is a novelist, so of course she has more freedom to make us stare straight into the face of truth. We all know that Amoruso and Sandberg don’t love the Trump administration and its stated intentions and policies around women’s rights. We know they too were likely horrified at all the accounts of sexual assault that came out before the election, and his “defense” that the women were too unattractive for him to have sexually harassed.

So why don’t either of their current projects and platforms and statements unequivocally say so? We get it with Sandberg-- she has massive fiduciary duty issues.  Since the last time I criticized her abandonment of this issue, she has acknowledged she should have done more and has done more. Amoruso on the other hand has little to lose and is supposed to be the madcap, unrestrained, free spirit of the two. The one who in the opening of the show says she never wants to grow up because “adulthood is where dreams go to die.”

She’s happy to look selfish, childish, petulant, and uncaring in this show, but draws the line at “political” in a time where so many other women-- both from my peer group and the TeenVogue crowd-- are finding their political voice.

Of these three women who are seen as feminists at a time when feminism has never been more needed who each have a new project, Atwood has come out on top with the most relevant statement of feminism today. Sandberg has mostly adeptly side-stepped the issue, by beautifully and authentically writing about grief and finding happiness instead. Amoruso is the one whose strategy and message confounds me.

She admitted after the Rally to Buzzfeed that she could have done a better job on incorporating politics into things. What she has always excelled at is listening to her audience and giving it what it wants. She has always had an almost uncanny mind meld with “her girl.” So either that stance will adjust or Amoruso will be building some sort of bizarro world TeenVogue army that really wants to just stay focused on the mascara in the gift bag.