Sophia Amoruso (part II)

This is part two of my notes from Sophia Amoruso’s conversation with Tim Ferriss. If you missed part one, you can find it here. There we answered:

– Why start small?

– Why have to have some skills and more importantly why to develop them?

– How to learn quickly?

– What is the most important thing?

These notes will pick up where we left off.



5- Be different. Why was Nasty Gal named Nasty Gal? Because Windblown Lilies of the Valley was already taken. Or something like that.

Amoruso writes that there were other vintage clothing sellers on eBay, but they had names, “so bohemian it hurt.” “So the contrarian in me grabbed the keyboard and named my shop-to-be Nasty Gal Vintage.”

It’s entirely possible that Amoruso would have ended up like all the other vintage clothing stores if she wasn’t different – but she was, and her difference helped.

It wasn’t just a difference in name, but in attitude and quality. Amoruso writes in #Girlboss:

“The bin to my right had all of the vintage items that had just sold and needed to be shipped out. I’d grab an item and inspect it to make sure it was in good shape. I’d zip zippers, button buttons, and hook hooks, then fold it and slide it into a clear plastic bag that I sealed with a sticker. I’d print out a receipt and a Photoshop-hacked note reading “Thanks for shopping at Nasty Gal Vintage! We hope you love your new stuff as much as we do!”— even though “we” was just me. Then I’d put it in a box and slap a shipping label on. Only I didn’t slap anything— I took a lot of pride in how carefully I affixed those labels.”

A different name. A different attention to detail. A different brand too. Nasty Gal meant something. She recalls getting emails from fans who said that they looked at her pictures before going out at night as a way to get style ideas. Amoruso wasn’t just selling clothes.

She succeeded in the way that Peter Thiel suggests: “All happy companies are different: each on earns a monopoly by solving a unique problem. All failed companies are the same: they failed to escape competition.”

Nasty Gal escaped the competition.

Note, you don’t need a lot to be different. Dan Ariely and James Altucher talked about the Significant Objects Project where people gave rich histories to objects on eBay and saw the scales skyrocket. Sometimes you can be different in one important one.

This is what Amoruso did. She was different because her brand told a story that people were eager for.

You have to be different. If you really want to succeed, you can’t be the 100th pizza place in town. Morgan Housel spoke about being different in investing. Judah Friedlander spoke about being different in comedy. Michael Mauboussin spoke about being different in business.


6- Push boundaries and grey areas until you get pushed out. Nasty Gal succeed despite breaking the rules of eBay. Before explaining what they did, let’s set the stage with a matrix of rule following:


Laws & Rules Follow spirit Break spirit
Follow letter No trouble Maybe trouble (could get off on technicality)
Break letter Maybe trouble (could get off on public support) Trouble

We move in and out of these boxes all the time. Follow the speed limit? No trouble box. Keep up with traffic? Maybe trouble box. This box – “I was just keeping up with traffic officer” – is where Amoruso operated on eBay. She writes:

“For example, it was against eBay policy to link to an outside website, social media or otherwise, from your listings. However, it was common practice among sellers to link to their MySpace pages— almost everyone did.”

For vintage clothings sellers on eBay, the letter and spirit of the law were two different lines. You could cross one but not both. Amoruso nudged the line, then the line moved.

That’s the thing with the spirit of the law, it can move on you. It’s one thing to keep up with traffic on I-95 on Labor Day weekend. It’s another to speed through a school zone. You can also get outed by others. This is what happened to Amoruso, someone in the vintage clothing community reported her to eBay, and she was gone.

This entire experience reminded me of bananas, specifically Philip Zemurray the Banana King. In the wonderful book, The Fish That Ate the Whale we see all the grey box things Zemurray did. One example of this type of thinking was when one of his competitors lobbied the government for bridge regulations that would keep Zemurray from getting his bananas from one side of a river to another. Zemurray circumvented the letter of the law (don’t build a bridge) by building building two (very) long barges.


7- Keep a low overhead. When you’re buying used clothing to sell on your eBay store it’s easy to keep overhead low. When you’re running a business with employees that’s one of the fastest growing in fashion it isn’t – but that’s exactly what Amoruso did.

Step by step, she slowly scaled up. First she lived in a pool house with no kitchen. “There was shit on top of shit,” Amoruso writes, “boxes balanced on top of a toaster oven on top of a mini-fridge like a game of household-object Jenga.”

From there she went to a 1,000 square foot loft, away from everything. The best parts were that the space was bigger and had the inherent advantage of being away away from her friends in the city. Amoruso doesn’t come out and say it, but it seems like the lack of distraction helped her work her butt off. Each upgrade in space was just big enough.

Finally Nasty Gal had made it and everyone got Herman Aeron chairs. This was it. They had arrived.  

WAIT WAIT WAIT. That’s not what happened.

“There was no way that I was going to have interns rolling around on these things!” Amoruso writes. “It sent the wrong message to the company to preach frugality while balling out on twelve grand worth of chairs. You can’t act like you’ve arrived when you’re only just receiving the invitation. We couldn’t return the Aeron chairs, but after we were settled in our new LA offices, our poor office manager, Francis, spent six months selling them . . . on Craigslist.”

The low overhead (Amoruso calls it frugality) mindset can be very helpful. Ezra Klein got a writing fellowship because he didn’t have bills to pay. Jerry Seinfeld, Jay Leno, and Sarah Silverman – as they said in Sick in The Head – each kept their expenses low so they could do the work they wanted.

Low overhead is a form of optionality.


8- Know thyself. Amoruso isn’t the CEO of Nasty Gal anymore. “The things I think I’m good at,” she says, “aren’t the skills a CEO needs.” But it wasn’t always this way.

Early on this mean that if she knew she didn’t know something, Amoruso had to learn it. Hence why she bought the book eBay for Dummies. She also recognized that while her modeling and photography skills were good – they weren’t great. She knew this and hired/bartered for people with those skills.

Michael Lombardi calls this “management of self” the most importance management there is. To know what we don’t know and to act wisely on that. How do we start to figure out this sort of thing? Experimentation.

Naval Ravikant, Scott Adams, and Gretchen Rubin all advocate for self experimentation with habits, foods, and even routes to work.

Amoruso has figured out her limits and abilities thanks to living and breathing (experimentation with what works and didn’t) Nasty Gal for the past decade (2006-2016).


9- Life’s natural state is hard. Now that Amoruso is not the CEO, she’s not off on a beach. “It doesn’t get easier,” she tells Ferriss, “it’s the same but with different stuff.” In essence, there’s no finish line.

You don’t feel content to be done if you’re doing things. There’s no permanent finish line.

Marcus Aurelius wrote: “People who love what they do wear themselves down doing it, they even forget to wash or eat.”

That’s where Amoruso is, she’s worn down because she loves what she’s doing. It seems right to end with this Casey Neistat video:

Thanks for reading, I’m @mikedariano on Twitter. If you want more from me, you can get updates on my Survivor’s Bias project here.

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