I love Sophia Amoruso! She’s hot, young and oh so ‘real’. She pioneered a vintage eBay store into a fast-growing $85 million online business. But this fairy tale did not end happily: The once-trendy etailer hit a wall, filed for bankruptcy, and ended up selling its brand to Boohoo.com of the U.K. for just $20 million.

End of story.

She’s also the author of the 2014 New York Times bestseller #GirlBoss, host of a popular podcast and executive producer of a Netflix TV show, all bearing the same brand: GirlBoss. ( I binge watched her Netflix series in one Saturday!)

Rags-to-riches-to-rags stories are certainly not uncommon in the entrepreneurial world. Nevertheless, the Nasty Gal saga provides three key takeaways that resonate across the business realm.


  1. Cashflow:

As with so many founders, Amoruso had a knack for everything about her business, except for business itself. After raising venture capital, she moved the company into lavish L.A. headquarters, opened two brick-and-mortar stores, leased a dedicated distribution center and spent a fortune on marketing.

That’s an enormous leap in burn-rate for a startup that didn’t have enough of a track record to prove its business model was sustainable at scale. When funds began to dry up, so did the company’s marketing. Sales took a dive, cash flow went south, and that, my friends, is what you call a death spiral.


2. Starting is easy, scaling is hard.

Mark Zuckerberg may be Facebook’s product visionary, but the company’s ability to execute flawlessly at scale is the work of Sheryl Sandberg, who Zuck recruited early on as his chief operating officer. I’m not sure if the social network would have flopped like MySpace if not for Sandberg, but she is responsible for its stellar growth.

We all have weaknesses, but a CEO must have enough self-awareness to recognize that, and hire a talented executive team with complementary skills. That’s what it takes to effectively scale a business.

3. Success is not a goal, it’s a way of life.    

The good entrepreneurs love what they do, know how to run every aspect of their business, and are executing well at scale. They’re in it for the long haul, so there’s a good chance they’ll be successful over the long haul.

I’ve met countless ‘wantrepreneurs’. So many just want to get in, make a quick million or two, and get out. That’s just not how it works. Gary Vaynerchuck speaks about his success being in “playing long term”, it’s the truth!

This Girl Boss, despite her business failing, will land on her feet and sometimes it is those who fail who have the most to teach us! Here are some of my favourite, Sophia Amoruso quotes to inspire you:

 “You don’t get what you don’t ask for!”


“Fortune favours the bold who get shit done!”


“Doubt kills more things than failure ever will!”