Steven Bartlett - Sophia Amoruso

1) Sophia Amoruso talks about her upbringing and the influence it had on her. She describes how her parents worked entirely on commission and how money was good at first, but then things became tough, leading to them filing for bankruptcy. This experience taught her the importance of assimilating into different environments and helped her develop a real internalized drive to do better. Sophia's father's criticism was challenging but has worked well for her and challenged her self-confidence, which has become a superpower for her.

2) Sophia speaks about her rebellious nature from a young age and how it was a combination of both hereditary and environmental factors. She mentions how as children, we are like narcissists, and everything seems to center around us, but being in a household with a lot of arguing and drama teaches us to survive in certain ways. She talks about how her behavior was rebellious when she moved out of her parents' house, and even in middle school, she defied her teacher's orders to throw away her apple, which earned her the attention of her entire class. She was sure capitalism was the worst thing, and her lack of desire to live a conventional life ultimately turned into ambition, leading her toward building a successful business.

3) Amoruso talks about her struggles with attention deficit disorder (ADD) and depression, which she has dealt with her entire life. She initially thought that her inability to focus was due to her environment, but eventually sought treatment for it. Sophia sees a psychiatrist and practices holistic methods to help manage her conditions. She also discusses how she has always been a bit dark and skeptical, which may have contributed to her struggles growing up in a traditional educational environment. Despite this, she has built a successful fashion empire and continues to work on being a well-rounded person.

4) Sophia discusses her teenage years and early twenties, where she felt lost and struggled to find a place to belong. From homeschooling to moving from place to place, Sophia was constantly searching for people like her. She was diagnosed and prescribed antidepressants at 16 and moved out when she was 17 before graduating high school. Sophia moved into a closet under the stairs with friends she met through music. Her plan was to go to the Evergreen College, but she found it wasn't worth it after obtaining residency. Sophia worked as a stripper but didn't know precisely how long. She was happy that she did not find any permanent or comfortable place in these communities as it forced her to remain a creative thinker.

5) Sophia discussed her experience as a stripper and how it helped her become comfortable with her body. She also mentioned that every job teaches you something and that there are transferable skills that can be applied to business. For example, she learned how to entertain people and be charismatic as a stripper. However, she also mentioned that taking shortcuts and breaking rules can put you in other people's hands, such as being arrested for shoplifting, which resulted in her missing her court date. This taught her a lesson about not cutting corners and being in control of her environment.

6) Sophia talks about how she started selling vintage clothes online and how she got the idea from eBay sellers who friended her on MySpace. She loved vintage clothing and saw that eBay sellers were making good money selling vintage items. She was working in the lobby of an art school while waiting for health insurance and used the downtime to start her own eBay store selling vintage clothes, eventually growing it into the successful business that became Nasty Gal.

7) Sophia talks about how she started in the vintage clothing business by selling clothes on eBay with her own unique twist. She says that she reverse-engineered everything that her competitors were doing and did it 10 times better with the help of resourcefulness, creativity, and independence. She also notes her resistance to authority and the feeling that school was stifling her natural curious and motivated nature. Sophia emphasizes that her success came from her ability to think critically and avoid blindly following convention, and this mindset allowed her to create a genuine, unique representation of herself and her brand rather than a manufactured, assigned version.

8) Amoruso, talks about the importance of balancing naivety with convention when starting a business. She explains how her unconventional and edgy style stood out in the vintage clothing market on eBay, but ultimately, she knew that she needed to learn from the success of others in order to survive. She shares how her naivety caused her to make mistakes when managing her team and how she had to learn the importance of holding people accountable. Despite her lack of experience in leadership, she was able to succeed by showing up, delivering on her promises, and reflecting on her mistakes.

9) Sophia discusses the challenges of managing a young and inexperienced workforce during her company's early days, and how bringing in experienced adults helped balance out the team. She shares her belief in the importance of understanding both present and future approaches to business, and how she made mistakes along the way, almost going under multiple times. Amoruso details the growth of the company from its beginnings on eBay to being valued at $350 million with a $60 million investment from index Ventures in 2012, which marked a turning point in the company's profitability.

10) Amoruso talks about the impact of receiving a large amount of investment money on her company and herself. She recalls how the company grew so fast and hired 100 people as it aimed to increase its revenue from $28 million to $128 million. Sophia admits that she hired the wrong people and it was like a family business that just got big, with little processes and no intentional culture that had been established. Despite this, she suddenly found herself worth $280 million on paper after being valued at $350 million, and how the book she wrote turned into a phenomenon.

11) Sophia Amoruso reflects on how her upbringing and lack of acceptance led to a lack of confidence in decision-making. She also talks about the negative press she received when NastyGal fell apart and how she was seen as a caricature of the American dream. Sophia discusses the responsibility she had as a symbol for entrepreneurship and how she struggled with the negative press as it did not align with who she believes she is.

12) Sophia talks about the struggle of being associated with a company or a persona that no longer represents who she is, especially when there is a PR campaign highlighting her past. Despite having mental health challenges and facing criticism for her company's failure, she maintained her mental health by starting new ventures like Girl Boss and focusing on her community of supporters. Amoruso also shares how Nasty Gal's valuation, which reached $350 million, ended up being the nail in the coffin for the company, and how the lack of a playbook and experienced executives hurther e-commerce business in the early days.

13) Sophia discusses the challenges she faced when dealing with venture capitalists who valued her company at over $350 million. She admits to not negotiating well, having only received one term sheet, and not realizing that her interests were not necessarily aligned with her investor's. Amoruso also reflects on the dynamics of her company and how she only knew about 10% of what was happening with her employees, making her accountable for everything that took place.

14) Sophia shares advice for young founders looking to start companies. She recommends validating your idea with the simplest, ugliest product and talking to potential customers before raising money or marketing. She also advises founders to listen to their gut and maintain their intuition, which may have gotten them where they are as a founder in the first place. She reflects on her hardest day, which surprisingly was not related to her business, but rather when her husband left, despite having agreed to take a bigs wing in her personal life.

15) Sophia talks about her experience dealing with personal issues as the CEO of a large company, and how it has influenced her current business approach. Amoruso explained how she doesn't plan on being a large company CEO again, because she enjoys being an early stage founder who plays to her strengths. Shedescribed the benefits of her current businesses, Business Class and Trust Fund, which are profitable, relatively self-led, and require little human capital compared to running a large company.

16) Amoruso talks about her perspective on success and how she balances her personal life with her business ventures. She emphasizes the importance of staying nimble and not rushing to solve problems by pouring money into them. Sophia describes her belief in "magical thinking," which involves thinking beyond the obvious and believing in one's capabilities to achieve things that may seem unattainable. She opens up about her proudest moment, which was paying off her mother's marriage, and shares her uncertainty about what her future proudest moment will be.