Real Talk with #GIRLBOSS Sophia Amoruso

Aug 25, 2020

In her early 20’s Sophia Amoruso launched an eBay store selling vintage clothing. A few years later, Nasty Gal skyrocketed to $100 million in revenue and Sophia found herself (for better or worse) as an icon of female entrepreneurship. In this episode, Jeff and Sophia discuss the triumphs and travails of rising in the business world and how to avoid many of the pitfalls new business owners stumble into.

To take Sophia’s new Commune course, Finding Business Clarity, for free, go to

Jeff: We were just discussing the etymology of Sophia's name.

Sophia Amoruso: I thought you were going to say edamame.

Jeff: That's next.

Sophia Amoruso: Okay. I can spell both just for the record.

Jeff: Sophia is Greek, right?

Sophia Amoruso: I'm half Greek.

Jeff: Yeah.

Sophia Amoruso: My name is Greek.

Jeff: Your name is Greek and its origin is wisdom, right?

Sophia Amoruso: Yeah. Sophia means wisdom.

Jeff: Your last name is ... You pronounce it with more gusto than I do.

Sophia Amoruso: I mean, it's Amoruso but it's probably something like Amoruso or some something that sounds kind of drunk in Italian.

Jeff: Yeah. That's an Italian name.

Sophia Amoruso: That's Italian. Yeah.

Jeff: You're a wisdom lover.

Sophia Amoruso: Yeah. Yeah.

Jeff: Do you think that's a fair description of yourself?

Sophia Amoruso: I think so. I think I'm a savant wisdom lover. I don't think I'm a studied wisdom lover.

Jeff: Yeah. I'm not sure. I mean, I'll take your word for it, but you do have a certain evanescent quality or I would say that you're really curious.

Sophia Amoruso: Yeah.

Jeff: You tend to not be at all intimidated by figuring things out that would otherwise seem quite difficult.

Sophia Amoruso: Yeah. I don't know where that came from. I might just be so stubborn that it works out for me. Stubborn enough to believe that I can do things maybe.

Jeff: Well, what's happening in your brain? Give us a window into your brain because there'd be, I don't know, some sort of technical platform that would normally spook the hell out of anyone and they would have to find a specialized expert and hire them at some inflated hourly wage. You might also do that, but that-

Sophia Amoruso: Sometimes.

Jeff: ... but that wouldn't be your first go-to. Your first go-to would be to actually understand it first yourself.

Sophia Amoruso: Yeah. I mean, it's hard to hold people accountable if you have no idea what they're doing. Having a foundation of what it is that someone you hire something to do is doing and understand how difficult it is or not how difficult it is, or just at the very least trying to understand a platform. It feels like we're talking mostly, probably about software here because there's a lot of software that goes into online courses. I'm sure both Communes and then Business Class, the course that I'm building outside of Commune and it's a lot.

Sophia Amoruso: It's a lot of different systems that have to connect to one another and have to tell one another what's happening, who's checking out which email and what you should do about it and who's interested in what and passwords.

Jeff: Yeah. Would that be a bit of advice that you might give an aspiring entrepreneur who maybe has a staff of just themselves? Is that before you hire anyone, figure out how that thing that they're going to do works.

Sophia Amoruso: Yeah. Yes. I mean, when I started my first business, it was an eBay store. Pretty simple. Not every business is that simple to start, but I had software, I had photography, I had Photoshop. I had to understand how to upload files to an FTP server and do a certain amount of HTML to format my eBay listings and my Myspace profile. I learned everything that I needed to know. I learned enough Photoshop to edit photos and design some really basic graphics. I would never have learned Photoshop if it weren't for necessity.

Sophia Amoruso: I didn't have a Photoshop background, but I figured if other people can figure this stuff I can too. Yes. I think that what you can learn at the beginning of your business, you should learn because learning from experience is really different than being told by an expert, whatever expert means. I'm just starting to think a lot about the word expert lately or ... Yeah.

Sophia Amoruso: Just like things ... I mean, I don't believe anybody can do anything, but I like to think if someone else has the aptitude to do something and if I have the access to the same thing, there's no reason I shouldn't be able to do it.

Jeff: Yeah. No. That's really good advice. I would try to learn something new every month, even if it was like tie my shoe, or I can also-

Sophia Amoruso: Did you figure it out?

Jeff: Barely.

Sophia Amoruso: Looks like it.

Jeff: Barely.

Sophia Amoruso: Did you do that?

Jeff: I did it all by myself.

Sophia Amoruso: Okay.

Jeff: This was two month endeavor. Like one month I was like, "Okay. I'm going to figure out how to run paid Facebook campaigns." I was like, "Yeah. I'm going to upload the custom audiences and make the lookalike audiences and put the pixel in and track the pixel to something." I immediately sucked at it, but did get some sort of insight into actually what it was and the purpose that it served. Then when it came to actually hiring the person that could actually do it I could talk to them like an adult.

Sophia Amoruso: You at least understood the terminology.

Jeff: Yeah.

Sophia Amoruso: Yeah. That's one thing that I'm going to have to start doing when we launch Business Class and that's something I'm not going to learn.

Jeff: Yeah.

Sophia Amoruso:

I have one amazing woman named Audrey who's my digital operations manager and she knows enough to be dangerous, but she's not doing it herself even. That's something where you're spending money. You want your return on investment to be great and your learning curve for something like digital marketing can be more expensive than paying the right person.

Jeff:You're a seria l entrepreneur as am I. That doesn't mean that we make cereal.

Sophia Amoruso: I do like this keto cereal though called Magic School?

Jeff: Magic Spoon.

Sophia Amoruso: Spoon. Yes.

Jeff: They sponsor this podcast.

Sophia Amoruso: Oh, they do?

Jeff: Shut up.

Sophia Amoruso: Oh, that's amazing.

Jeff: That was the most native integrated-

Sophia Amoruso: Naturally integrated ad. Wow.

Jeff: Yeah. We'll have to pull them back in.

Sophia Amoruso: I'll DM them.

Jeff: That'd be great.

Sophia Amoruso: They sent me some cereal.

Jeff: Yeah. I've got it. The problem is it's all in my Hollywood office that we just basically gave up because you don't really need offices anymore.

Sophia Amoruso: Nope. Here we are in your living room.

Jeff: I know.

Sophia Amoruso: You can do so much. I mean, this is not a tiny home, but it's amazing how much work you can get done from home.

Jeff: Yeah. Just to have a rare blip of sincerity and then we can move on from that. I do want to express my really heartfelt appreciation for your trust in working with us and also you just your bravery and courage just to jump into something fresh and new. I guess courage might be a descriptive word for an entrepreneur.

Sophia Amoruso: I think you have to be courageous. I think you have to be stubborn. I can be hasty and make rash decisions. I think this is maybe a quick decision that I made that I'm really excited about and is going to be a really, really great partnership. Sometimes that courage doesn't always work out because I could be more thoughtful about the decisions that I make, which is what finding business clarity is. It's really thinking upfront about what kind of life we want to have, what kind of business we want to have.

Sophia Amoruso: This is something that's a partnership, but I could start a business right now very quickly that would just turn into some massive thing that spirals out. I'm at a stage in my life where, yes, I feel confident making certain decisions and then others I'm actually moving a lot more slowly than I used to. Thank you. I mean, this Commune is incredible, right? I'm in such great company. We've become friends. This is very easy and comfortable. It just feels incredibly natural, so it's one of those things that's like a why not? I didn't really even ask myself that question. It's just a yes.

Jeff: Yeah. I mean, you've started two businesses that have had pretty significant trajectories. Now, you're stepping into a new role for yourself in many ways as a dispenser of wisdom of guidance. Did you have a mentor when you were starting out?

Sophia Amoruso: I didn't initially and then I hired a consultant who is so much more than a consultant. I officiated his wedding, his name's Dana Fried. It was me in a weird little shipyard with a thousand square feet and a bunch of plastic bags and USPS bins on the floors and stinky clothes with snot rags that needed steaming and dry cleaning and had to be shot and put on this website because it was vintage clothing, which is what I was doing. He handed me my first employment handbook and was like, "Here, this cost $50,000 to put together with an attorney. You just white label it."

Sophia Amoruso: Taught me how to hire and fire my first people. Put together my first financials, was really a huge cheerleader for me and a great mentor early on in the business. I really wish I had kept him around after we raised venture capital because they were like, "Okay. We're stepping in here." They were great. I loved my investors at Nasty Gal, but he's a really special person. I'm lucky to have learned from him.

Jeff: Yeah. Someday we'll have a podcast that compares war stories around institutional money, but that is not the subject of this one.

Sophia Amoruso: Yeah. I can talk about that forever.

Jeff: Yeah.

Sophia Amoruso: It'll just make everybody's face sour and they'll just turn the podcast off.

Jeff: Yeah. Yeah. Well-

Sophia Amoruso: It's not inspiring.

Jeff: Yeah. Well, I'll duel you in that particular regard myself. You said something the other day when we were talking that I thought was really interesting and insightful about being an entrepreneur. You said when you're an entrepreneur, you work for the customer, not for a boss. I guess I would ask you this question. It's sort of loaded, is the customer always right?

Sophia Amoruso: No. No. Totally not, but it doesn't really matter. It's like if you're in a relationship and you hurt the other person, even if you disagree you just apologize and move on because it's the result of what happened. Not like your intention sometimes that you have to answer to, right? It's just so much easier to say like, "Wow, I didn't realize this would affect you like that. Here's how I can make it right." So much easier than battling people or customers. People often just want to be heard and it's the same thing with employees, right?

Sophia Amoruso: They come to you and complain. All you have to do is acknowledge people and say, "Hey, I hear you. I understand the impact that you made on your life, your dress is late. You were supposed to wear it to a bachelorette party. I'm so sorry that it didn't get to you before you got to Vegas. Let us overnight you one, or let us overnight one to Vegas or let us give you a generous store credit." Right? That stuff goes so far. Just a little bit of generosity, even if it's just listening to people, but especially taking action.

Sophia Amoruso: Showing people that you really care and make it right for them even if you don't feel like you really did that much wrong, they'll become a loyal customer forever.

Jeff: Yeah. Yeah. I was reading that ... Who was it? It was Marshall Field. Remember Marshall Field's. It was kind of like a Nordstrom theme. I think he coined that. There was another-

Sophia Amoruso: The customer is always right?

Jeff: Yeah. There was another retail giant that also thought that way. That was like, "It didn't matter. Just always do the right thing." It's kind of that protocol at a restaurant. Someone complains about their food. Let's bring them another meal and that's it.

Sophia Amoruso: Yeah. It's cheaper to retain a customer, even if you have to deal with them than it is to acquire another one. It's cheaper to-

Jeff: That's a good point.

Sophia Amoruso: ... retain an employee and develop them and coach them than it is to hire someone new and it sets your company back several months. It's just like it's just way better to invest in people, including your customers.

Jeff: Yeah. Let's talk a little bit about team and leadership because that's, for me, something that I just ... I went to the school of hard knocks on it. I would say for a prolonged period of time, for, to be honest, like a too long period of time, I felt like I needed to be involved in every minuscule decision that happened. It was, in retrospect, really disempowering for the people on my team, but also in the end sucked for me because now that I'm a little bit more of a grownup, I'm so glad I don't have to make every decision.

Sophia Amoruso: I know. I know. That took me a really, really long time. We think we're so special and we know so much more than everyone else and ideas are so much better because we're inspired entrepreneurs, right? That's just not true.

Jeff: Yeah.

Sophia Amoruso: You can have entrepreneurs within your organization who are just as inspired as you and better at certain things than you are. I mean, you have a team of entrepreneurs here. You weren't standing across from me when we filmed this entire course, but I'm sure that everything that you wanted was carried out without you being here. That's leadership, right? That's you taking what it is that you understand that you want, that you know is right for your business, and really deputizing people to take that and fulfill on it so that your business can then scale and you can scale yourself without actually having to do more work.

Jeff: Yeah.

Sophia Amoruso: That doesn't work.

Jeff: Yeah. Well, I think that's a great point that you make and by empowering other people, it creates more space for you to then empower and grow yourself. I mean, I would say for five years personally, I was in a place of intellectual paralysis because I was so involved in the weeds and I didn't grow at all. For you, I wonder though, because .... And it's not unique to you, but it is representative of the position that you hold, where you, Sophia, are so representative and inextricably tied to the brand that you represent.

Jeff: I wonder what the upsides and pitfalls of that are, and then how you gracefully or potentially sometimes ungracefully manage that.

Sophia Amoruso: Yeah. I think it's really challenging. It's great. It's a blessing. I'm so lucky to have a generation of women who have followed the trajectory of my career and read my books and followed me and supported me through ups and downs of my career. It's also come with its fair share of criticism and that's because I was like, "Ta-da." The poster child of entrepreneurship in 2014, when I wrote this book called Girlboss, and was on the cover of business magazines. That also set me up to be a target, so when I made mistakes, they were really loud mistakes.

Sophia Amoruso: They were the same mistakes that every other founder makes, same things that happen in every other company, but because I had built this millennial utopia of expectation that Nasty Gal was the perfect company and that I was the perfect leader because I was so celebrated, the backlash was big when I made mistakes. I think that there's huge upsides to having a personal brand. There's so much more gravity, right? People connect with people. People don't necessarily connect with a brand. That's why brands have endorsements and they pay people a lot of money to make it sound like their brand has a brand voice.

Sophia Amoruso: That's just something that's natural to me that I've lent to my brands, but as an individual, that's just me, which also in terms of scaling myself, I know I can't delegate copywriting. I have help here and there sometimes, but my voice is very specific. There's a lot of things that only I can do because otherwise it feels like I phone things in, but most of that is about marketing and creative and things that I really enjoy anyway.

Sophia Amoruso: There are certain things that I'm going to have to do because everything that I'm building really is coming from what I care about and what I actually believe. That's not something anyone can really be clairvoyant about or invent.

Jeff: Yeah. No. You said something, I think maybe it was the first time we spoke, that has stuck with me around vulnerability on social media. You obviously being very front forward in your brands, but also just in your personal brand. That you are very honest and vulnerable and you offer a window into your life which people resonate with and appreciate, but that sometimes that vulnerability has to be curated, I think what you call-

Sophia Amoruso: Yeah. Performative, right?

Jeff: Yeah. There's probably parts of your life you're just like, "Well, actually, that part is off limits." I wonder how you manage that. How do you delineate between being vulnerable and open and then this is just my private life?

Sophia Amoruso: Right. Yeah. I'm pretty open about most things. I learned that there are certain things that if you announce them, "Oh wow. I'm going to talk about my experience of this really challenging thing." It's like, "Okay." For example, about a year ago I had a miscarriage, right? I haven't talked about it and I have enough distance now that I don't need to. It's not like a big thing. No one's going to reach out to me. If I was talking about it while it was going on, it's enough to just move past something and grieve something and then to have other people culturally feed it back to you and be like, "I'm so sorry that happened to you."

Sophia Amoruso: It's like, "Fuck. I wasn't thinking about that. Why are you reminding me of this?" There's things you can put out into the world that might help other people and share your story and might maybe help process stuff for you. Even a few people I told there'll be time ... There was a time where I was like, "Oh." I told one of my investors and we went to lunch and she was like, "I'm so sorry about the miscarriage." I'm just like, "Shut up. What? Just, we're going to lunch. Don't bring that up." Even with people that I knew, not necessarily social media followers, it was just like, "Wow, I wish I had told a few less people actually."

Sophia Amoruso: Culture really projects itself back on you. Something as exciting as getting engaged or married, for example, I'm now divorced. I got engaged. I got married. As soon as you get married ... Well, as soon as you get engaged, "Do you have a date?" It's like, "What? I just got engaged. I'm not in a hurry." Then you get married, "Where's the baby?" It's just like, "I don't know man. Stop projecting all this shit onto me. This is my life and my timeline. Where did you guys get all this?" It's just like, I've never had pneumatic ... Sorry, this is me complaining.

Sophia Amoruso: It's like I've accomplished so much that the amount of congratulations I got for picking somebody and betrothing myself to them for the rest of my life ... This is just off topic, I thought was really bizarre. Like that's an accomplishment. It's just so strange. Yeah.

Jeff: Yeah.

Sophia Amoruso: It wasn't much of an accomplishment, but-

Jeff: Well-

Sophia Amoruso: It was a beautiful wedding. That was an accomplishment. It was great party.

Jeff: I don't doubt it. Everything you do is tasteful and beautiful.

Sophia Amoruso: Thank you. Thank you.

Jeff: To the detriment of my own vanity. Just kidding. I want to talk to you just also a little bit about the role of business in general, and then also your business and the impact that you want to create with it. As I survey society and I look at the crumbling, traditional institutions of government and science and media and all of this, I feel like it's more and more incumbent on businesses and the private sector to actually move society forward. I think we've seen in the last, at least four years, business leaders take more of an active stance on social issues.

Jeff: I'm wondering how you see the role of the private sector or businesses generally around the notion of social impact. Then, more personally, what does that impact mean for you and where are you positioning your legacy within that?

Sophia Amoruso: Yeah. Now, somehow naturally I've made an impact just by selling dresses that made people feel more confident. That just happened somehow and that was probably the beginning of what that felt like, but it was very unintentional. I've put that energy out into the world a lot, but it's fashion. It's stuff. It's not super sustainable. That was part of my life for a long time. Okay. I believe that businesses can make a huge impact. I believe it's the imperative of every business to make an impact.

Sophia Amoruso: A responsibility of anyone who is fortunate enough to have a business, if they can afford to in whatever way they can because not everybody can make an impact beyond impacting their own lives and feeding their families. It used, and to be like you said, it's the last few years, right? I built a company called Nasty Gal, an edgy, progressive, provocative fashion brand. When I wanted to do a program where we donated a part of the proceeds to Planned Parenthood, my entire executive team and marketing team ... and this was, I don't know what, six/seven years ago, eight, a long time ago.

Sophia Amoruso: They were like, "Oh no, no, no. You're going to alienate half the population." It's a different era.

Jeff: Totally.

Sophia Amoruso: That's just table stakes. It's totally okay. It was so polarizing and frowned upon for businesses to take any position in anything politically, culturally, environmentally. We've trickled into it so I think it's really interesting. I think a lot of it can be performative, but I also would rather companies pretend than not do anything at all. I think over time businesses will be held accountable. We see more and more of that. As a marketer, things like employer brand, impact that you make as an employer to your team or environmental impact, or caring about hiring for diversity.

Sophia Amoruso: These are all things that usually companies historically held close to the vest, didn't necessarily publicized. Consumers didn't care. They were like, "Cool. I like Coke. I like this thing. Cool. You sold me this thing. Your ad worked." Now, it's the integrity of companies that's selling things, right?

Jeff: Yeah.

Sophia Amoruso: People care about what Uber's like on the inside. Then they'll book an Uber. 10 years ago that wasn't the case. I think that's an incredibly powerful thing.


Jeff: You almost can't talk about this topic right now without talking about diversity and inclusion. Any company with any moral rudder at all, believes in diversity and inclusion. And it is one thing to make a declarative or performative statement about diversity and inclusion.

Jeff: Then it's a whole other challenge to actually execute that as a leader within your company of how you actually create a team that is reflective of a pluralistic society. I don't know. This is a very complicated conversation.

Sophia Amoruso: Yeah. You're like, "Sophia answer this. Can you solve this problem?"

Jeff: Yeah. I mean, I'll just give you just a small window into the processes that I've thought about where so often in small companies, because they're small, you're hiring because you know people and your friend knows someone and they're like, "Oh, they'd be great for this." There's no poor intention there of hiring a friend of a friend who is actually very qualified, but what that precludes is a broader and wider process that opens that role up to as many people as you possibly can.

Jeff: That's one thing that I've committed to in my businesses, where, as tempting as it is just to ... Because I honestly don't love hiring. It's not a favorite pastime of mine.

Sophia Amoruso: Yeah. Yeah. I actually really like it, but I get what you mean. It's like, you can interview 50 people or you can be like, "Oh cool. My white friend's white friend."

Jeff: Right. Yeah. I don't know if there's any other windows into wisdom that you have around this topic. I think it's right out there and I think people are trying to figure out clumsily how to best deal with it.

Sophia Amoruso: Yeah. It's incredibly important I think for business. Businesses have to set examples from the inside out of what they want their audiences to look like. It benefits everybody to have a broader customer base, right? To serve a variety of people. When you hire people inside your company that don't look like you, they're going to represent a broader culture within your organization and help you speak to communities that you may not naturally. Whatever, HBR has statistics that are like diverse teams perform much better, right?

Sophia Amoruso: I view it as cross training where if you just run straight forward and it's like your body's not going to get used to a variety of movements. If you just do pushups, your ankles are going to get weak. Not that I do any of these things. You're really laying a foundation and shocks for building a business that will live in society and probably be more sustainable long-term, than one that starts from a very myopic point of view. It's a challenging thing, right? Most of my friends are white. I really would prefer to work with people I've already worked with and not all of them are white.

Sophia Amoruso: I think we did a really good job hiring for a diverse team at Girlboss, but it means going outside of my social circle. It means making sure that we're casting a very wide net for positions that could be really, really easy to fill with someone who's close by or someone who knows someone. On top of that, companies are being held accountable to it. People are asking. I'm sure people are asking you, what does your team makeup look like?

Jeff: All the time.

Sophia Amoruso: I'm not even part of Girlboss anymore and people asking me for statistics.

Jeff: Yeah.

Sophia Amoruso: I'm proud of what they were when we had more than five people. I'm going to be proud of what our team looks like once I have more than one employee at Amoruso&Co, my new company.

Jeff: Yeah. Let me ask you about you right now and the process that you're going through and the person that you're stepping into, because I've always thought that you don't really know how much you know, until you teach it.

Sophia Amoruso: Totally.

Jeff: I wonder if you're going through a process right now, as you're generating all this curriculum around business and how to make one of like, "Holy shit. I know a lot."

Sophia Amoruso: I know stuff.

Jeff: Yeah.

Sophia Amoruso: I know stuff and it's exhausting. I'll age with it. It's showing up on my face, so I might as well make money off of it. Yeah. Right. I know a lot and I've expressed it really piecemeal in interviews and in Instagram captions, but I've never really digested it into any kind of resource that's the kind of resource that I would want. Finding business clarity is that Business Class will be that. 14 years of huge successes and total face plants is like, "I better make use of this. I better help. I'm so tired." I said this a little bit earlier.

Sophia Amoruso: It's like I spent the last 14 years of my career learning by trial and error. Now I want to help people not have to learn by trial and error. Like, "Please just save yourself the pain. You'll make plenty of your own mistakes, so at the very least just take these data points and do what you will with them because I have a lot of them." It's great. It's like I'm moving into this almost coach like educator space, which is like, I didn't even go to college. I never had coaches. I don't even really gravitate to that space very much and I have this expectation of myself.

Sophia Amoruso: It's like, "Sure. I'm wearing orange and I can talk on camera, kind of, with a prompter, kind of. I can do interviews, whatever, if someone asks me questions." I'm not like rah-rah. I'm not a born coach. I don't wake up every day to just turn on a camera and start spouting inspirational shit. I really feel like I'm supposed to be that person moving into this. Yeah. I'm courageous and whatever. I'm doing courageous things, but at the end of the day, I think we're all a little insecure about what we're doing. I just feel like ... I'm like, "Wait, I'm totally not qualified to do this."

Sophia Amoruso: These people have been coaching their whole lives. They just flip on a camera and they're like, "Yeah. You can do anything." I'm just like, "Man, maybe you can because I can't. Here's what I know, but take it with a grain of salt." I don't even know if that sells shit.

Jeff: Yeah. Well I think the demonstrable difference between what you're doing and what a lot of business coaches are doing is that you actually have the experience of running businesses.

Sophia Amoruso: I hope that's the difference. I hope someone cares.

Jeff: Because you could just be a coach for being a coach for being a coach.

Sophia Amoruso: I know.

Jeff: I mean, I feel a sense of kinship to you because we've been there on day zero.

Sophia Amoruso: In the trenches.

Jeff: You know, we've been part of the excitement, the best part for me, which I sense is the best part for you, which is that escalator at the beginning when things are catching. Then we've been there in the maintenance days and in the shaky days. There's just no replacing that experience, and hopefully experience leads to Sophia to wisdom.

Sophia Amoruso: Wisdom? I think so. There's wisdom and then there's doing something with it.

Jeff: True.

Sophia Amoruso: You can be an academic and you can be a philosopher, but if you're Nietzsche but you're miserable I don't really care about your philosophy.

Jeff: He was miserable.

Sophia Amoruso: Yeah. If you're a miserable person spouting philosophy, it's coming from ... You know what I mean? There's so much out there written by miserable people that we're supposed to learn from, but it's like eating food that was made by someone who hated making that meal. It's got to be imbued with a bunch of bullshit you're passing along. They're passing along some psychic garbage, even if their words ring true, whatever.

Jeff: Yeah. Well-

Sophia Amoruso: Go find some happy people to learn from.

Jeff: Yeah. Well, I have a very good friend who's a tremendous painter and visual arts is also something that often gets attributed to that the best work gets made out of this lonesome pain. He was like, "No. Fuck that. I make my best art out of joy."

Sophia Amoruso: This such a played out passé thing, that whole pose. It's such a pose. It's just like, "Okay. Okay, sad, white guy. Well, life is so hard for you. Wow. You contemplated existence and it bummed you out. Join the club. You're not special."

Jeff: Yeah. Well, whether you are aware of it, and I know you are aware of it on some level, but I'll just reinforce the notion that you have the ability to inspire a lot of people, sail a lot of ships.

Sophia Amoruso: Yeah.

Jeff: I mean, I can just see from an observational perspective, just on your social media, how much people look to you for guidance and for inspiration and for joy. In some ways that's a lot of responsibility, but in another way that's a great gift to be in that position.

Sophia Amoruso: Yeah. It's a gift if I leave this planet having helped anybody, right? I've done my job. I think, and thank you, it's also a lot of pressure. It's like, "Wait, you're projecting all this stuff onto me because I wrote a book seven years ago and you're saying I helped you. Only you can help yourself." You read a book. I actually played no role and now you should at least own and be proud of what you accomplish because I didn't change your life, right? Only people can change their lives and they love to give their power away. Legacy is important to me.

Sophia Amoruso: I want to leave a smear, whether it's a canceled Netflix series or a Forbes cover where my company is going bankrupt. I just want to look back in, I don't know how many years, another 30/40, whatever years I'll live, 50, and show a grandkid or something and be like, "Yeah man, I don't know how I pulled that one off."

Jeff: That's your next book? Sophia Amoruso's Great Smear.

Sophia Amoruso: Yeah. Yeah. Just leave a mark.

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