Hitchhiker to CEO: How Sophia Amoruso became Forbes' richest self-made woman
TQD: Issue 10
Welcome to The Quest Digest 👋🏼
Read the thoughts of Justin Kan, the co-founder of Twitch 🧠 , scout opportunities to work with us, access episode summaries, and connect with our amazing and driven community!
Know anyone that would love to join over 20,000 smart, curious, and interesting listeners?
In this issue:
Quest Minutes - takeaways from our episode with Sophia Amoruso, ‘the Cinderella of tech’
Justin’s brand new show: OnlyFriends! Join JK and his friends as they celebrate Justin.tv’s 14th annivesary
The Quest YouTube channel is live - catch up on full-length episodes, or save them to snack on later
JK x Coffeezilla: a conversation about online ‘success’ scammers
👠 Quest Minutes: Sophia Amoruso
Catch the full conversation here:
Rebel With a Cause:
Sophia Amoruso is “the Cinderella of tech.” 1 Her story is about fearlesslesly and relentlessly going against the grain and operating against the status quo. As a complete outsider to the tech world, she has been battling expectations all her life.
Founder of Nasty Gal, a women’s fashion retailer that raised millions
Forbes Cover - ‘richest self-made woman’, and then losing it all
Feature of Girl Boss, a Netflix show based on her life
Sophia turned her resilience into a superpower. From becoming a rich CEO and married, to having it all crumble away within months; she never gave in and remained a rebel at heart.
The Hitchhikers Guide to Becoming a CEO (3:56)
“I did the eBay thing for like a year-and-a-half and realized, ‘holy shit I'm building a brand on eBay,’ which is totally weird… I [eventually] left and launched Nasty Gal and it sold out overnight.”
At 22 years old, Sophia was far from the status quo. To make ends meet, she hitchhiked along the West Coast and resorted to dumpster diving and stealing. Finding initial success in flipping vintage clothing on eBay, Sophia quickly boostrapped her online business and founded Nasty Gal which raised millions.
Fall of Nasty Gal (29:08)
Sophia was living the life, sipping Chardonnay in superyachts and infinity pools. Unfortunately, her lack of experience as a CEO started to weigh down on the company, compounded with a cluster of wrong hires. In the span of a couple of months, Sophia’s life completely fell apart.
“Ultimately it was Hail Mary after Hail Mary…Within six months it was, Forbes Cover, dude (husband) bails, company files for Chapter 11. And while all of this is happening, there's a Netflix series being made about my fucking life. It comes out four months after bankruptcy, telling 150 million households that I'm the founder of a fucking E-bay store called Nasty Gal. For the first time in 10 years, I'm trying to move on from Nasty Gal.”
Success 101 (50:05)
There is no textbook routine that will bring you success. Take it from someone who has been at the top, and picked herself back up from rock-bottom. Sophia doesn’t subscribe to the ‘status-quo’ of successful personalities on the Internet. They’re not as perfect as they make themselves out to be, and you shouldn’t expect yourself to be either. Rely on your resilience, passion, and instinct - they’ll get you where you need to go.
“Slack is important because it's really easy to beat yourself up over not doing all the well-rounded things that younger millennials have figured out.”
Extra lessons:
Venture capital is a double-edged sword: when you raise, know what you are signing up for. A big valuation sets high expectations, and if your watermark is too high you can't raise and will starve when things go bad.
Have a plan: when you become an entrepreneur, learn from others so you have a basic understanding of things like board advisors, profit-loss statements, and culture.
🎙 OnlyFriends
Join Justin Kan, Emmett Shear, Jaime Quint, and Tikhon Bernstam as they celebrate Justin.tv’s 14th anniversary! 🥂 🎉 🥳
OnlyFriends is a place where JK and three of his crazy successful buddies shoot the shit about their lives, the latest tech drama, and behind-the-scenes stories. Stay tuned on Justin’s YouTube channel for more episodes coming!
Tweet Feature: #StopAsianHate
Quest HQ and Quest Fam community members are deeply saddened and disgusted by the surge of anti-Asian violence in recent weeks. It is heartbreaking to hear that a few of our community members have felt the repercussions firsthand.
Quest HQ is honored to be able to provide a safe space for individuals to share their experiences with our community and provide support for one another. We’re here to makes these trying times a little less trying.
It is our collective responsibility - not just for those in the Asian community, but as global citizens to stand against ignorance and hate. Click above to support AAF (Asian American Federation), and spread the word. This is everyone’s fight #StopAsianHate. ✊🏼
📺 The Quest YouTube Channel
If you’re new to The Quest, you might have missed our episodes from Season 1! Check out our brand new YouTube channel to find our catalogue of full-length episodes - we’ll continuously update this until we catch up to our latest releases. Make sure you’re subscribed with notifications on! 🔔
🤑 Justin Kan x Coffeezilla: Calling out scammers selling success
Join JK and Coffeezilla as they discuss the cesspool of Internet ‘success gurus’. You’ve seen them everywhere: scams, pyramid schemes, bad business opportunities, junk programs, and promises of easy financial success. Steel your mind and stay sharp! 🗡
👀 Coming up next…
Cameron Yarbrough: Cofounder and CEO of Torch Leadership Labs, a leadership development company built on principles of psychology and management best practices.
Episode drops Tuesday 23rd March @ 9AM PST. See you there 👋🏼
Perlroth, Nicole. "Naughty in Name Only". The New York Times.