
59 segments available
Sophia Amoruso is an American business woman and New York Times best-selling author of ‘#GIRLBOSS’ which later became a Netflix series of the same name. Topics: 0:00 Intro 02:04 Early context 07:04 Do you know what affected you most as a child? 11:06 Always wanting to rebel 17:33 I'm a little dark 24:47 Being a stripper 29:38 Shoplifting 33:54 Ads 35:50 The start of Nasty Gal 59:34 Dealing with self-doubts 01:08:34 The downfall of Nasty Gal 01:20:18 Advice for aspiring entrepreneurs 01:24:04 Your hardest moment 01:25:37 Would you ever be a CEO again? 01:31:06 Magical thinking 01:32:37 The last guest's question Are you ready to think like a CEO? Gain access to the 100 CEOs newsletter here: https://bit.ly/100-ceos-newsletter Sophia: Instagram: https://bit.ly/3A19HWz Twitter: https://bit.ly/3ocKOEx Join this channel to get access to perks: https://bit.ly/3Dpmgx5 Follow: Instagram: http://bit.ly/3nIkGAZ Twitter: http://bit.ly/3ztHuHm Linkedin: http://bit.ly/3ZFGUku Telegram: http://bit.ly/3nJYxST Sponsors: Huel: https://g2ul0.app.link/G4RjcdKNKsb Zoe: http://joinzoe.com use code ‘CEO10’ for 10% off Airbnb: http://bit.ly/40TcyNr
Sophia Amoruso shares her unconventional journey from being a rebellious young woman, including her experiences as a stripper and shoplifter, to becoming the founder of Nasty Gal. She reflects on how her early life choices shaped her entrepreneurial spirit and led to her eventual success.
"didn't you get an offer to sell the company for 400 million dollars yeah I did what it made you super rich why didn't you say yes you're very good at this Sophia also founder of Nasty Gal A best-selli..."
Sophia discusses the pressures of being a successful entrepreneur and the challenges that come with it. She reflects on her naivete and the responsibilities she faced as the 'girl boss' of Nasty Gal, leading to her eventual downfall after ten years.
"husband of like a year left the headlines weren't nice what is it like from a mental health perspective it's hard to pull yourself out of a hole when you don't want to get out of bed it's challenged m..."
In this segment, Sophia takes us back to her childhood in San Diego and Sacramento, sharing her experiences as an only child and the impact of her parents' tumultuous relationship. She reveals how these early experiences fueled her desire to escape and explore the world beyond her suburban upbringing.
"take me back to those suburbs in San Diego and give me your earliest context wow I was born in San Diego Sharp Memorial Hospital only child eternally and only child I think wound up having the persona..."
Sophia opens up about the challenges she faced growing up in a strict household, including the financial struggles her family encountered. She reflects on how these experiences shaped her understanding of authority and her drive to succeed.
"early age what what did you what did you want at a very early age when you say you wanted out oh yeah what did you want yeah I wanted out of my family home it wasn't happy my parents didn't get along ..."
Sophia discusses the critical nature of her father and how it influenced her self-perception and drive. She shares how the criticism she faced growing up became both a challenge and a motivating factor in her life and career.
"affectionate after like an argument and even then it was like I don't know hand-holding or something they were very strict as well I had to beg to go to a boy's birthday party in sixth grade we weren'..."
In this segment, Sophia reflects on her rebellious nature during her teenage years, including her disdain for conventional life and her exploration of alternative lifestyles. She discusses how this rebellion eventually led to her entrepreneurial journey.
"owned a motel and they all grew up on a motel so there's like generations of my family who wouldn't necessarily call themselves entrepreneurs but they're people who ate what they killed and that's wha..."
Sophia candidly shares her struggles with mental health, including depression and self-doubt. She discusses the challenges of overcoming these obstacles while trying to maintain her entrepreneurial spirit and the importance of self-awareness.
"was like adults were not trained to be parents and weren't any further along with their maturity sometimes than I was at my age you know I looked at teachers and thought wow you know you have domain e..."
Sophia elaborates on the balance between self-criticism and self-acceptance. She reflects on how her upbringing instilled a drive for self-improvement while also challenging her confidence, leading to a complex relationship with her own self-worth.
"ways I don't know in some ways hold myself accountable because I'm always I almost want to say second guessing myself but also very um in a very I guess someone said Jesuit way at one point but a way ..."
In this segment, Sophia discusses her journey towards self-acceptance and the realization that her past experiences, including her struggles with mental health, have shaped her into the person she is today. She emphasizes the importance of understanding one's own narrative.
"talking about your funnel there yeah he would critique you yes when you say critique do you mean oh that's that's naughty don't do that no no like that's not how you do something or why why'd you do i..."
Sophia Amoruso discusses her childhood experiences with ADHD and depression, explaining how her environment influenced her mental health. She reflects on being diagnosed as a child and the misconceptions she had about her condition, emphasizing the importance of seeking treatment and understanding one's mental health struggles.
"the way we view the world as a survival mechanism and he says one of the things that happens when we're in a where you were a young child and we're in a house where there's lots of arguing and lots of..."
In this segment, Sophia opens up about her darker personality traits and lifelong struggles with depression. She shares how her childhood experiences shaped her outlook on life and her skepticism towards happiness, revealing the challenges of maintaining a positive facade while dealing with internal battles.
"think we're all struggling to be a well-rounded person I don't know some people seem to like have these parents that teach them that and they come out and they're like yeah you know and it's not you k..."
Sophia reflects on her feelings of being lost and her search for a sense of belonging. She recounts her experiences moving frequently during her youth and how this transience influenced her identity, ultimately leading her to create her own community and embrace her individuality.
"when you were 16. oh I went to see a psychiatrist when I was like 10. I mean I was in therapy when I was like 10 11. with what's trying to be diagnosed like what's wrong with her why can't she stay on..."
Sophia shares her journey after moving out at 17, including her experiences with homeschooling and her aspirations for college. She discusses her desire to find a place that resonated with her values and how her early life shaped her path towards entrepreneurship.
"mail I thought the like most embarrassing thing would be would be to wear the cap and gown I was like what is that I don't understand what's the tassel why do you have to wear a robe what is this robe..."
In this segment, Sophia describes her feelings of being lost in her late teens and early twenties. She talks about her search for a 'tribe' and how her experiences in various cities contributed to her sense of isolation and the eventual realization that she needed to forge her own path.
"even state tuition was expensive so I lived in Washington state for a year to get state to get residency so I could go to that school and by the time I got residency I was like this school's not gonna..."
Sophia discusses her time as a stripper, describing it as a period of self-discovery and empowerment. She shares her experiences in the industry, the fun she had, and how it helped her become more comfortable with her body, while also acknowledging the complexities of that lifestyle.
"because it's forced me to make my own and force me to stay creative thinker and also I don't know I this isn't fair but the people in some of those communities like peaked and never left it's like you..."
In this candid segment, Sophia recounts her experiences with shoplifting, sharing her rationale and the thrill of evading capture. She reflects on how these actions were a form of rebellion and a misguided attempt to navigate her financial struggles, ultimately leading to a court date that changed her perspective.
"yeah they say I've read a new book where you said that you believe you hold the world record for having the most shitty jobs like back to back throughout that period of your life they say you know I'v..."
Sophia shares a pivotal moment in her life when she faced the consequences of her rebellious actions, including a court date related to shoplifting. She reflects on the lessons learned from this experience and how it shaped her understanding of authority and personal responsibility.
"so I'm like 20. Maybe 19. and I went to the sliding scale Women's Clinic and but but it was the only day I could get in but it also happened to be the day of my court date because I had gotten arreste..."
In this humorous yet reflective segment, Sophia discusses the thrill of stealing and her rationale behind it. She shares anecdotes about her shoplifting escapades, emphasizing the absurdity of her actions while also acknowledging the deeper issues that drove her to such behavior.
"you know doesn't it doesn't ever go that low there's clearly um a slight issue here with authority and it feels to me like the ultimate Authority which is the law eventually was like he can't [ __ ] w..."
Sophia connects her past experiences with shoplifting to her entrepreneurial journey, highlighting how her early misadventures informed her business mindset. She reflects on the lessons learned from her rebellious youth and how they contributed to her eventual success in building Nasty Gal.
"and when I did get caught I had like a George Foreman grill I think a basketball organic tampons some food really nice shower curtain rings they were metal and then they had like ceramic they were hea..."
In this segment, Sophia discusses the role of fear in her shoplifting experiences. She explains how hesitation can lead to failure, drawing parallels between her past actions and broader life lessons. This reflection on fear and confidence highlights her growth and the mindset that propelled her into entrepreneurship.
"I would go into Barnes and Noble and they had a no chase policy like I knew what the policies were at these places because if their employees Chase someone shoplifting it's gonna cost them way much mo..."
Sophia recounts the beginnings of her eBay store, which eventually evolved into Nasty Gal. She describes her motivation to create a business that aligned with her interests and independence. This segment illustrates her transition from a rebellious youth to an aspiring entrepreneur, setting the stage for her future success.
"like who's carrying a huge stack of books I was right in the front of the store and I just like walked my car and I'd put them on Amazon for 10 cents less than all the other resellers I'd sell them ov..."
Sophia explains her passion for vintage clothing and how it influenced her decision to sell on eBay. She reflects on the unique market dynamics of vintage fashion and how her love for style drove her entrepreneurial spirit. This segment emphasizes the importance of personal interests in shaping business ventures.
"way I never stole from individuals that was like not on thesis for me no I couldn't justify it I would never feel comfortable doing it um but big box retailers I was like over the last couple of how l..."
In this segment, Sophia discusses how her curiosity and resourcefulness played a crucial role in her success on eBay. She highlights her ability to reverse engineer successful strategies and improve upon them, showcasing her innovative approach to entrepreneurship. This reflection underscores the value of curiosity in business.
"paying attention to this podcast will know why I've sat here with some incredible Health experts and one of the things that's really come through for me which has caused a big change in my life is the..."
Sophia reflects on her unique approach to selling on eBay, emphasizing her commitment to quality and creativity. She contrasts her methods with those of typical sellers, highlighting her focus on excellent copywriting, styling, and photography. This segment illustrates her determination to stand out in a crowded marketplace.
"been having it here in La for the last couple of weeks and it's a game changer ladies and gentlemen our newest brand partnership will come it's no surprise to regular listeners on this podcast the fir..."
Sophia discusses the irreverent spirit of Nasty Gal and how it differentiated her brand in the vintage clothing market. She reflects on the cultural context of her business and the importance of authenticity in her entrepreneurial journey. This segment captures the essence of her brand's identity and its roots in her personal experiences.
"podcast you can read up about everything they're doing and you can pre-order your Zoe program at joinzoe.com and they've been kind enough to offer an exclusive 10 off code CEO 10. so you can put that ..."
Sophia Amoruso discusses her approach to building Nasty Gal by reverse engineering what others did and improving upon it. She emphasizes the importance of first principles thinking, which allowed her to innovate rather than simply copy competitors. This segment highlights how her unique perspective and resourcefulness set her apart in the eBay marketplace.
"successful at that time I'm not sure a lot of people saw that price Arbitrage and they didn't build a nasty girl so when you reflect on why and how you were particularly successful how did you diagnos..."
In this segment, Sophia explains the edgy and irreverent branding of Nasty Gal, contrasting it with the more conventional vintage sellers of her time. She shares the inspiration behind the name, drawn from Betty Davis's album, and how this bold identity helped her cut through the noise in a crowded market. The discussion reveals the significance of brand spirit in business success.
"filtering out convention they can kind of see throughout the truth whereas convention like is safety it's Comfort it's it guarantees you a pre-tried blueprint so people follow that but then these othe..."
Sophia reflects on the balancing act between naivety and convention in entrepreneurship. She shares her experiences as a young founder, highlighting how her lack of experience led to both innovative ideas and significant challenges. This segment underscores the importance of understanding both traditional business practices and the fresh perspectives that come with youth.
"when you start a business and you don't need to survive you might have more time to Naval gaze or you might do things super conventionally but when you need to survive there are certain things that ot..."
In this segment, Sophia recounts the explosive growth of Nasty Gal, going from $150,000 a year to $150,000 a day. She discusses the challenges of scaling quickly, including the need for structure and experienced leadership. This narrative illustrates the complexities of managing a rapidly growing business and the lessons learned from her journey.
"send me to the Grave it happened so fast that's a quote um it was shocking how fast it all happened nasty girl went from doing 150 000 a year to doing 150 000 a day and then 150 000 over lunch yeah 15..."
Sophia shares her insights on hiring practices and leadership as a young entrepreneur. She reflects on her early mistakes of hiring inexperienced staff and the eventual need for seasoned professionals to stabilize the company. This segment emphasizes the importance of balancing youthful energy with experienced guidance in building a successful organization.
"really well they got bought out within six months so they got a big return but good job yeah what do you attribute at such a young age I'm just gonna interview you for a second because you couldn't ha..."
Sophia narrates her transition from selling on eBay to launching her own website, Nasty Gal Vintage. She details her revenue growth and the strategies that led to her success, including understanding her customer base and curating products that resonated with them. This segment highlights the entrepreneurial journey from a side hustle to a thriving business.
"present which is why you want to hire a 16 year old that gets Tick Tock or whatever and you also need to hire someone that's maybe double their age experienced in client services and understands the o..."
In this segment, Sophia discusses the impact of venture capital on Nasty Gal's growth. She explains how a $60 million investment changed the dynamics of her business, allowing for rapid expansion but also introducing new complexities. This narrative sheds light on the challenges and opportunities that come with external funding in entrepreneurship.
"eventually you know 28 million dollar run rate super profitably I would never have known and so yeah year two left eBay about halfway through and launched my own website nastygalvintage.com and did 25..."
Sophia reflects on the pressure that comes with significant investment and growth expectations. She shares her experiences of managing a rapidly expanding team and the challenges of integrating new hires into the company culture. This segment highlights the realities of scaling a business and the importance of maintaining a cohesive team.
"with a 28 million run rate yeah you're profitable at that time significantly pretty significantly I have a 10 or 20 nothing I don't know I don't know I didn't even look at that I was I I never had to ..."
Sophia discusses the recognition and accolades that came with Nasty Gal's success, including being featured in Forbes. She reflects on how this attention impacted her and the company, emphasizing that her focus was never on glory but on building a sustainable business. This segment explores the intersection of personal achievement and business growth.
"what did it break hmm I mean we no longer had to live within our means that's what investor money does unless you maintain profitability and keep that money in the bank for you know another time or po..."
Sophia Amoruso reflects on the difficulties of integrating a diverse team into a rapidly growing company. She discusses the lack of established processes and intentional culture at Nasty Gal, highlighting the chaos of managing a large group of people who don't share a common language or understanding.
"story where uh people are building this Tower or something but they all speak different languages and I I could be completely wrong I don't think I am but none of them get along or understand one anot..."
Amoruso shares her feelings about suddenly having a valuation of $280 million and the pressure that comes with it. She describes the excitement of being featured in Forbes and the mixed emotions of public recognition, emphasizing the disconnect between her perceived success and her internal struggles with self-doubt.
"how does that make you feel when you you know then they put you in the front cover of Forbes yeah how does that make you feel it was a blast um I didn't do any of it to have Glory or go on a Victory l..."
Sophia discusses her experiences with imposter syndrome and how it motivates her. She reflects on feeling like an outsider in high-stakes environments and how this perspective can be a superpower, allowing her to make unique connections and learn from her experiences.
"you know and she was like what you wouldn't be here if that wasn't the case what what are you talking about you're great but I get nervous right um I get nervous on stages and I'm still like you know ..."
Amoruso contemplates the role of self-doubt in her life and whether she would choose to eliminate it if given the chance. She argues that challenges and struggles contribute to her identity and self-awareness, making her journey richer and more meaningful.
"radical would you remove that self-doubting voice if I put a button in front of you and said you press this you'll never doubt yourself again no that's so boring I had a coach recently and he was love..."
Sophia shares her approach to decision-making, influenced by her upbringing and the voices of her parents. She discusses the importance of being deliberate in her choices and how her past experiences shape her current decision-making framework.
"opportunity to gain self-awareness do you think it's additive to your performance or reductive I think it can slow me down and I can make really slow decisions because I doubt myself but beyond that I..."
Amoruso reflects on her childhood experiences and how they shaped her self-perception and decision-making. She discusses feeling misunderstood and the impact of her parents' differing views on her upbringing, leading to a lack of confidence in her choices.
"and it's seven days with no phone no Internet no books no music you're with 30 other people and you're going through this process of mapping your patterns from your childhood against your parents and ..."
Sophia talks about the pressures of being a public figure and the misconceptions that come with it. She shares her feelings about the media's portrayal of her journey, particularly during the rise and fall of Nasty Gal, and how it affected her identity.
"advice in that Retreat did you did you have to sort of like go upstream and figure out where that belief started is that the point of that Retreat did you figure it out did you go Upstream what a good..."
Amoruso describes the whirlwind of events surrounding her rise to fame, including the success of her book and the Netflix series. She reflects on the challenges of maintaining her identity amidst the public's expectations and the rapid changes in her life.
"that I'm mostly not what have you been told you are oh gosh um so nasty y'all fell apart after 10 years it was it was a quick rise and it was it was it was a it was a slow rise and it was a relatively..."
Sophia discusses the downfall of Nasty Gal and the media's reaction to it. She reflects on the unrealistic expectations placed on her as a representative of her generation and the impact of her company's failure on her personal and professional identity.
"who had built a toxic culture or just no intentional culture at our all that like warped into something that wasn't perfect but wasn't I still don't think it was the worst and now this person this con..."
Amoruso shares how she maintained her mental health during the tumultuous period following Nasty Gal's decline. She emphasizes the importance of her supportive community and how her experiences resonate with others facing their own challenges.
"be you're someone who's as you said you've had a long history with mental health challenges what is it like in like in that 12-month period what's going on from a mental health perspective I had falle..."
Sophia reflects on the insights gained from her failures and how they have shaped her understanding of entrepreneurship. She discusses the importance of learning from mistakes and how her journey can inspire others to embrace their own challenges.
"is face planting in private and in the same way that watching some random Community College Dropout from Sacramento start a business with an internet connection and a computer gave them license to you..."
Sophia discusses the overvaluation of Nasty Gal at $350 million and how it contributed to the company's eventual downfall. She explains the unrealistic expectations set by investors and the challenges of operating in a rapidly evolving e-commerce landscape, emphasizing the lack of a clear playbook during that era.
"you go oh okay [ __ ] you have all of this new information about which is corrected your hypothesis so when you if we go back and think about that fundraise for example um a lot of people will hear th..."
In this segment, Amoruso reflects on the deceptive nature of success in business. She describes how the appearance of thriving operations can mask underlying issues, and how the reality of layoffs revealed deeper problems within her company. She emphasizes the challenges of being a CEO and the limited visibility into organizational dynamics.
"were no Ecom veterans or you know Performance Marketing people who had been in those jobs for even very long I was hiring Executives who had worked at like Macy's right um nobody had like econ it wasn..."
Sophia discusses the heavy burden of accountability that comes with being a CEO. She highlights the disconnect between her knowledge of company operations and the expectations placed on her, illustrating the complexities of leadership and the impact of employee experiences on her reputation.
"that because everything was going so well you know we're harder to notice and you know it's hard to be a CEO it's hard to be a founder I think something a lot of people don't realize is that you only ..."
Amoruso reveals a pivotal moment when she was offered $400 million for Nasty Gal. She reflects on the advice she received from her investor to hold out for more, discussing the misalignment of interests and the potential consequences of that decision. This segment explores the intricacies of business negotiations and the emotional weight of such offers.
"because there's truth to almost everything didn't you get an offer to sell the company completely for 400 million dollars yeah I did I owned 80 of it so that would have made you you know quick maths I..."
In this segment, Sophia shares her top advice for aspiring entrepreneurs, emphasizing the importance of validating ideas before seeking investment. She encourages founders to bootstrap their ventures as much as possible, highlighting the benefits of building a solid foundation before raising capital.
"look into the data room and due diligence yeah and then copy yeah exactly yeah so we didn't get that far I don't regret it um but yeah that was a big thing you know for me that would have been a lot o..."
Amoruso discusses the significance of maintaining a reasonable valuation when raising funds. She explains how inflated valuations can lead to challenges in securing future investments and the importance of aligning expectations with market realities, providing insights into the current venture capital landscape.
"you just had an idea and were asking for a check when you do raise money having a reasonable valuation is important and a lot of Founders optimize for price because bigger price an investor pays the m..."
Sophia emphasizes the importance of listening to one's gut as an entrepreneur. She warns against solely relying on external advice and stresses the need to cultivate personal intuition, which is often what drives founders to success in the first place.
"the money I've as an angel investor I have three of these right now and it's like Hail Mary's two of them have figured out how to survive ones like we have another term sheet I mean I've been there wh..."
Amoruso reflects on the hardest day of her life, which coincided with her husband's departure. She shares the emotional turmoil she experienced and how it impacted her perspective on personal and professional commitments, illustrating the intersection of personal struggles and entrepreneurial challenges.
"first place which day was your hardest day over the last since you were since you first started that store on eBay is there a day you look back and go do you know what that period or that day was just..."
In this segment, Sophia discusses her decision to step back from being a CEO of a large company. She explains her preference for early-stage ventures and the fulfillment she finds in helping new businesses grow, contrasting it with the challenges of managing larger organizations.
"why I don't I just I don't want to that's not the job I want I'm an early stage founder I'm a master at creating brands that cut through the noise what happens though if one you know you're running a ..."
Amoruso talks about her current projects, including her entrepreneurship program, Business Class. She highlights the importance of creating sustainable business models that allow for personal engagement without the burdens of traditional CEO responsibilities, showcasing her approach to modern entrepreneurship.
"throughout the year and two weekly calls with students and post in the lounge which is our community keeping it that's it no yeah I'm playing I'm I'm I'm not playing small with business class I'm play..."
Sophia emphasizes the importance of intentionality in defining her version of success. She reflects on the pitfalls of external expectations and the need to create a business model that aligns with her personal values and lifestyle, ensuring that she remains true to her vision as her ventures grow.
"I have a 50 million dollar fund I can do that with a few people um and I'm using the assets that I have I'm the product my relationships and my network and my access to dealflow is my product my exper..."
In this segment, Amoruso defines 'magical thinking' as the belief in possibilities beyond the obvious. She uses the metaphor of Indiana Jones to illustrate the concept of trusting in unseen opportunities and encourages aspiring entrepreneurs to embrace their potential, even when they feel unqualified.
"yeah no no I I have had the Pearl Village of knowing what's on the other side of success and that a lot of it is not what you sign up for and that when you are successful you're stuck in it so I spend..."
Sophia reflects on her proudest moment of paying off her mother's mortgage and contemplates what her future proudest moment might be. She discusses the significance of finding meaningful pursuits in life and the uncertainty of what those might be, emphasizing the importance of self-discovery.
"like Indiana Jones where there's the vast where's this there's the vast Chasm between whatever and the Holy Grail and he has to trust that there is a an invisible bridge and he grabbed some gravel and..."
In the closing segment, Sophia expresses gratitude for the opportunity to share her journey and insights. She acknowledges the impact of her experiences on her current projects, Business Class and Trust Fund, and reflects on the importance of vulnerability and honesty in her storytelling.
"Sophia thank you so much for your time and thank you for the inspiration you've been an inspiration for me for many many years and that's why I reached out to you to sit here with you and you are abso..."