NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239

Last updated: Jun 2, 2023

The video is an interview with Sophia Amoruso, the founder of Nasty Gal, who shares her rebellious past as a stripper and shoplifter, and how she built a successful online business despite her lack of experience and naivete, but also discusses the challenges she faced with mental health and the downfall of Nasty Gal after 10 years.

The video is an interview with Sophia Amoruso, the founder of Nasty Gal, a best-selling author, and a powerhouse in the entrepreneurial world. Sophia talks about her rebellious past, including being a stripper and a shoplifter, before building her online business. She shares her journey of starting Nasty Gal, which went from making $150,000 a year to doing $150,000 over lunch. Sophia also talks about the challenges she faced as the poster child of entrepreneurship and how her lack of experience led to the downfall of Nasty Gal after 10 years. She also discusses her mental health struggles and how she overcame them. The interview also touches on Sophia's childhood and her desire to escape the suburbs and her unhappy family home.

  • Sophia Amoruso was rebellious from a young age and worked as a stripper before she was 21.
  • She started her online business, Nasty Gal, by selling stolen items on Amazon.
  • She eventually transitioned to selling vintage clothing and grew her business to make $150,000 over lunch.
  • Despite her success, she struggled with the responsibility of being a poster child for entrepreneurship.
  • Nasty Gal fell apart after 10 years due to personal and financial challenges.
  • Sophia discusses the challenges of pulling herself out of a hole when struggling with mental health.
  • Sophia's upbringing and family background had a lasting impact on various elements of who she is today.
  • Sophia was rebellious from a young age, even in middle school.
  • Nasty Gal was a successful online business that Sophia built.

NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 - YouTube

NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 001

Rebellious Past and Building a Business

  • Sophia Amoruso was rebellious from a young age and worked as a stripper before she was 21.
  • She started her online business, Nasty Gal, by selling stolen items on Amazon.
  • She eventually transitioned to selling vintage clothing and grew her business to make $150,000 over lunch.
  • Despite her success, she struggled with the responsibility of being a poster child for entrepreneurship.
  • Nasty Gal fell apart after 10 years due to personal and financial challenges.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 002

Mental Health Challenges

  • Sophia discusses the challenges of pulling herself out of a hole when struggling with mental health.
  • Her confidence has been challenged, and she sometimes feels like she doesn't belong.
  • However, she also sees not belonging as a motivator to do things differently.
  • She discusses the importance of seeking help and taking care of oneself.
  • She also talks about the stigma surrounding mental health and the need to break it down.
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Early Life and Family Challenges

  • Sophia was born in San Diego and moved to Sacramento as a child.
  • She felt isolated and curious about the world while living in the suburbs.
  • Her parents didn't get along, and she often felt like a referee between them.
  • She wanted to escape her family home from a young age.
  • She remembers many silent car rides with her parents and feeling alone.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 005

NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 - YouTube

Call to Action

  • The interviewer asks viewers to subscribe to the channel to help it grow.
  • He notes that the bigger the channel gets, the bigger the guests will be.
  • He thanks viewers for their support and encourages them to enjoy the episode.
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Early Life and Family Background

  • Sophia's parents worked entirely on commission and didn't have a salary.
  • Her mom worked in model homes on weekends and her dad did loans.
  • Money was good when Sophia was younger, but it got tougher over time.
  • Her parents had arguments about money, and Sophia witnessed them cutting up their credit cards and filing for bankruptcy.
  • Generations of Sophia's family were people who ate what they killed.
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Assimilating into Different Environments

  • Sophia learned how to assimilate into different environments despite the challenges she faced when she was younger.
  • She realized that adults were not trained to be parents and weren't any further along with their maturity sometimes than she was at her age.
  • She looked at teachers and thought that they had domain expertise, but they were morally bankrupt and she didn't trust them.
  • Sophia learned to entertain herself independently.
  • She had a real internalized drive to do better and a self-criticism that has worked very well for her.
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Critical Father and Self-Criticism

  • Sophia's dad was half Italian and half Portuguese, and his dad was a mean guy.
  • Her dad had a lot of pressure on him when Sophia was young, and he didn't really have the best model of what a great parent looked like.
  • Sophia's dad was critical, and it instilled in her an unfortunate but also very fortunate always peeling back another layer of the onion examining herself.
  • She has a real internalized drive to do better and a self-criticism that has worked very well for her.
  • It has been challenging and has challenged her confidence over time, but it has also been a superpower in some ways.
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Conclusion and Personal Reflection

  • Sophia's upbringing and family background had a lasting impact on various elements of who she is today.
  • Her self-criticism has been both a challenge and a superpower.
  • She is a self-aware person and challenges her doubts and ego.
  • Sophia is proud of the things she's great at and recognizes the advantages she has.
  • She reflects on the criticism she experienced early on in life and how it has shaped her into the person she is today.
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Rebellious Past

  • Sophia was rebellious from a young age, even in middle school.
  • She went to the anarchist book fair in San Francisco and was against capitalism.
  • She didn't want to work in an office and wasn't ambitious.
  • Her lack of desire to live a conventional life turned into ambition and curiosity.
  • She eventually built a successful business.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 012

Childhood and Education

  • Sophia felt like she was being trained for something mediocre in high school.
  • She was sure she was being taught to memorize things and sit at a desk.
  • She was rebellious and didn't want to conform to societal norms.
  • She felt like she was being prepared for a life she didn't want.
  • She had a nature, rather than nurture, tendency to be rebellious.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 014

Criticism and Mental Health

  • Sophia's dad was critical of her and would critique her.
  • She learned how to turn criticism into something more balanced.
  • She faced challenges with mental health and had to take medication.
  • She struggled with anxiety and depression.
  • She had to learn how to take care of herself and prioritize her mental health.
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Downfall of Nasty Gal

  • Nasty Gal was a successful online business that Sophia built.
  • The company grew too quickly and Sophia wasn't prepared for the challenges.
  • She made mistakes and didn't have the experience to handle them.
  • The company filed for bankruptcy after 10 years.
  • Sophia learned from the experience and is now focused on building a new business.
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Challenges with Mental Health

  • Sophia talks about taking Adderall for her ADHD
  • She was diagnosed with depression as a child and has struggled with it her whole life
  • She describes herself as a "little dark" and not a bubbly person
  • She went to therapy and saw a psychiatrist as a child to try to diagnose her behavior
  • She was a curious and independent thinker who didn't fit into traditional educational environments
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Rebellious Past

  • Sophia shares that she was a stripper and shoplifter in her youth
  • She dropped out of community college and worked odd jobs before starting Nasty Gal
  • She started selling vintage clothing on eBay and eventually launched her own website
  • She had no business experience and learned as she went along
  • She was naive and made mistakes, but was able to grow her business to $400 million
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 019

Downfall of Nasty Gal

  • Sophia talks about the challenges of managing a rapidly growing business
  • She admits to making mistakes and not being prepared for the success of Nasty Gal
  • The company faced financial difficulties and filed for bankruptcy in 2016
  • Sophia stepped down as CEO and the company was sold to Boohoo
  • She reflects on the lessons she learned and the importance of taking responsibility for her mistakes
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Lessons Learned

  • Sophia emphasizes the importance of being true to yourself and your vision
  • She encourages people to take risks and not be afraid of failure
  • She acknowledges the challenges of entrepreneurship and the need for resilience
  • She talks about the importance of mental health and seeking help when needed
  • She reflects on the impact of her experiences and how they have shaped her as a person and a businesswoman
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Teenage Years and Moving Out

  • Sophia was diagnosed with ADHD and prescribed Ritalin in high school.
  • She moved out of her parents' house at 17 before graduating high school.
  • She lived in a closet under the stairs for $60 a month with musicians and artists.
  • She moved to Olympia, Washington to get residency for state tuition at Evergreen State College.
  • She described this chapter of her life as being very lost and looking for her tribe.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 023

Stripping and Being Lost

  • Sophia moved around a lot after leaving her parents' house, living in Seattle, San Francisco, Oakland, and Portland.
  • She was a stripper during this time and felt lost.
  • She was looking for a place to belong but never found it.
  • She believes that not finding a comfortable community forced her to be a creative thinker.
  • She is glad she didn't find a comfy place and that it's been uncomfortable since then.
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Starting Nasty Gal

  • Sophia started selling vintage clothing on eBay in 2006.
  • She named her store Nasty Gal after a Betty Davis album.
  • She grew her business through social media and word of mouth.
  • She wrote a book called #Girlboss about her journey and the lessons she learned.
  • She sold Nasty Gal in 2017 after facing financial difficulties and lawsuits.
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Mental Health and Self-Care

  • Sophia struggled with mental health issues throughout her life.
  • She believes that self-care is important and that taking care of yourself is not selfish.
  • She recommends therapy and meditation as ways to take care of your mental health.
  • She also believes that it's important to take breaks and not work all the time.
  • She encourages people to be kind to themselves and to prioritize their well-being.
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Rebellious Past

  • Sophia worked as a stripper for five months when she was under 21, using someone else's ID to work there.
  • She enjoyed the job because she didn't have to engage with anybody and got comfortable with her body.
  • She learned that exposure therapy helped her become comfortable with her body.
  • She got arrested for shoplifting and had to have the Women's Clinic write an excuse to the court telling them why she couldn't make it to her court date.
  • She learned that breaking some rules puts you in other people's hands and that she wasn't as autonomous as she would have liked to have been.
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Transferable Skills

  • Sophia believes that every job teaches you something that can be applied to business.
  • She learned from stripping that even though she didn't have the upper body strength to be the traditional one upside down swinging around, what she could do was enough to entertain other people.
  • She learned to be comfortable with her body, which helped her with exposure therapy.
  • She learned that breaking some rules puts you in other people's hands and that she wasn't as autonomous as she would have liked to have been.
  • She learned that cutting corners could lead to not being in control of her environment or getting stuck in jail.
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Mental Health Challenges

  • Sophia faced mental health challenges during the downfall of Nasty Gal.
  • She felt like she was losing her identity and didn't know who she was anymore.
  • She had to go through a lot of therapy to figure out what was going on.
  • She learned that it's important to take care of yourself and that mental health is just as important as physical health.
  • She realized that she needed to step away from the business and take a break.
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Downfall of Nasty Gal

  • Nasty Gal grew too fast and didn't have the infrastructure to support it.
  • The company had a lot of debt and wasn't profitable.
  • Sophia stepped down as CEO and the company filed for bankruptcy.
  • She learned that it's important to have a good team and to delegate responsibilities.
  • She realized that she needed to focus on her strengths and let other people handle the things she wasn't good at.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 032

Rebellious Past

  • Sophia Amoruso was a stripper and a shoplifter in her youth.
  • She would steal from big box retailers like Fred Meyer and grocery stores.
  • She would use a razor to cut off the sensors and pile a shopping cart high with stolen items.
  • She furnished apartments with stolen items like rugs and shower curtain rings.
  • She learned from people who were professionally trying to avoid participating in capitalistic culture.
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Building an Online Business

  • The first thing Sophia sold online was stolen.
  • She would go into Barnes and Noble and stack the most expensive books with the least pages.
  • She would sell the books on Amazon for 10 cents less than other resellers.
  • She would ship the books overnight and pay her $350 a month rent.
  • She was scared but believed that hesitation leads to failure.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 034

Challenges with Mental Health

  • Sophia faced challenges with mental health during the success of Nasty Gal.
  • She was diagnosed with ADHD and depression.
  • She struggled with addiction and self-medication.
  • She felt like she was living in a fishbowl and couldn't escape the pressure.
  • She eventually stepped down as CEO of Nasty Gal.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 035

Downfall of Nasty Gal

  • Nasty Gal filed for bankruptcy in 2016.
  • The company grew too quickly and couldn't keep up with demand.
  • There were issues with inventory management and quality control.
  • The company also faced legal issues and lawsuits.
  • Sophia learned from the experience and is now focused on her new company, Girlboss.
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Sophia's Early Jobs

  • Sophia worked in shoe stores, record stores, photo labs, Subway, dry cleaners, and bookstores.
  • She enjoyed alphabetizing things and mailing things.
  • Her last job was in the lobby of an art school in San Francisco.
  • She got the job for health insurance because she had a pre-existing condition (a hernia).
  • She had to wait three months for health insurance to kick in.
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Selling Vintage Clothes on eBay

  • Sophia started selling vintage clothes on eBay in 2006.
  • She loved vintage and thrifting.
  • She saw other eBay sellers selling vintage clothes for high prices.
  • She started selling stolen vintage clothes.
  • She eventually stopped selling stolen clothes and started her own vintage clothing business called Nasty Gal.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 039

Building Nasty Gal

  • Sophia started Nasty Gal as an eBay store in 2008.
  • She had no business experience and learned as she went.
  • She used social media to promote her business.
  • She eventually moved Nasty Gal to its own website.
  • The business grew rapidly and was worth $400 million at its peak.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 040

Challenges and Downfall of Nasty Gal

  • Sophia faced mental health challenges and was diagnosed with ADHD and depression.
  • She stepped down as CEO of Nasty Gal in 2015.
  • Nasty Gal filed for bankruptcy in 2016.
  • Sophia wrote a book called "Girlboss" about her experiences.
  • She started a new business called Girlboss Media.
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Starting an eBay Store

  • Sophia Amoruso waited three months for her health insurance to get fixed before starting an eBay store.
  • She saw an opportunity to sell vintage clothing at a higher price point.
  • The customer determined the price, and the items were selling for much more than what Sophia paid for them.
  • She connected her curiosity, independence, creativity, and resourcefulness to something legitimate that made money.
  • She started Nasty Gal selling vintage out of her boyfriend's apartment.
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Challenges with Authority

  • Sophia Amoruso has always had a challenge with authority.
  • She decided to stop going to school and was polite about it, but she didn't like being assigned things.
  • She couldn't be assigned something; it either came out or it wasn't there.
  • She believes that everyone is lazy, and you should be lazy for things that you hate doing.
  • She is only motivated by things she's curious about.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 044

Reverse Engineering Success

  • Sophia Amoruso reverse-engineered everything everyone else did and did a better job with her signature on it.
  • She did it with excellent copywriting, great styling, great models, and increasingly better photography.
  • She was extremely resourceful and would buy stuff on eBay and sell it for more than she paid for it.
  • She did things ten times better with a totally different spirit.
  • She thinks most people who start an eBay store are copying what other people are doing, but she did it differently.
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Thinking in First Principles

  • Sophia Amoruso thinks that her default to thinking in terms of first principles has been part of the reason why her eBay store was successful.
  • She did what other people were doing but did it 10 times better with a totally different spirit.
  • She was a first principle thinker who kind of thinks first about what she knows to be true.
  • She was really good at filtering out convention and could kind of see throughout the truth.
  • She was extremely resourceful and would buy stuff on eBay and sell it for more than she paid for it.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 047

Starting Nasty Gal

  • Nasty Gal was named after an album by Betty Davis, a stylish woman who put out incredible records in the 70s.
  • The spirit of Nasty Gal was irreverent and edgy, which was different from other eBay sellers at the time.
  • The company grew quickly, from doing $150,000 a year to $150,000 a day.
  • Naivety made Nasty Gal interesting, but it also sent the company to the grave.
  • When starting a business, it's important to learn from others and make your own way.
NastyGal Founder: I Was A Stripper! A Shoplifter! Then Built A $400m Business! Sophia Amoruso | E239 048

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