Sophia Amoruso: The AI Strategy That Runs My Business, Killing Girl Boss, & Facing AI Backlash

Hot Smart Rich with Maggie Sellers Reum

Entrepreneur Sophia Amoruso joins Maggie Sellers Reum to discuss her journey from bootstrapping Nasty Gal to managing a venture capital fund

Key takeaways

• Sophia Amoruso bootstrapped Nasty Gal to $30 million in revenue through online vintage sales.
• Effective networking is about making introductions that create value for both parties, not just 'picking brains'.

Main topics

• Entrepreneurial journey
• Venture Capital strategies

Notable quotes

Stop using em dashes.

Conclusion

A masterclass in resilience and reinvention, showing that success requ

Transcript preview

Speaker 2 (0:00) Success does paint a target on your back, and I think women kind of can't win. It's like the red lip is in, red lipstick's out. Go into the office, work remotely, make a decision for yourself, try something, go Speaker 1 (0:11) watch another podcast, and shut up. We have so much to catch up on. I know you as a friend first, but you are the founder of Nasty Gal, the author of Girlboss, and the founder of multiple other very successful businesses. You've invested in over 50 companies. You have points on the board. I was 22 trying to evade working for other people. Got really good at it. In 2022, you said, please stop using the word girlboss. Thank you. Do you think that people treated you differently? How can women start using AI to actually get ahead? Like, do you have a favorite prompt that you use all the time? That's not what I told you. Speaker 2 (0:47) Stop using em dashes. It's not this, it's that. Don't ever use that again. Those are the prompts I use the most. Speaker 1 (0:54) People feel like there's some silver bullet or big playbook. I think it's important to remember all it Speaker 2 (0:59) takes is one serendipitous thing to happen, one relationship. What Speaker 1 (1:04) are the frameworks that you would tell people of like investing 101? What really gets you excited? Speaker 1 (1:44) Sophia Maruso, are you ready to get hot, smart, rich? I already am. Yes, that is one of my favorite answers. I can't believe you're here. We have so much to catch up on. But before we get into how we know each other, what would you say to someone to get them to stay about what we're going to talk about today? I Speaker 2 (2:03) don't know because I have a lot of life experience and I'm maybe funny. You are funny. And there's probably something to learn here. Usually there is. Speaker 1 (2:12) I know you as a friend first, but you are the founder of Nasty Gal, the author of Girlboss, the founder of Trust Fund, and multiple other very successful businesses. So from your perspective or your point of view, how do you describe Sophia Amoruso? Speaker 2 (2:29) Sophia Amoruso is a cool, funny girl who accidentally started a business when she was 22, trying to evade working for other people, unemployable, started selling vintage online, got really good at it, bootstrapped a company to $30 million in revenue, called it Nasty Gal, wrote a book about it in 2014 called Girl Boss, spent 18 weeks on the New York Times bestseller list. Forbes called me one of America's richest self-made women. Got married, got divorced. Netflix series called Girlboss produced by Charlize Theron that came out a few months after my company had fallen apart. And that was really hard. Angel investor all along the way. Done a good job at it. Has good taste. Started a venture fund because of that called Trust Fund. Invest in startups, software companies, smart founders, and has a sub stack. And now living in London where we are today and loving it with poodles and no car and lots of places to walk and so much coffee and gardens and... flowers. I don't even know who tends to them. And lots of museums and Speaker 1 (3:47) great proximity Speaker 2 (3:48) to Europe. Speaker 1 (3:49) Okay, first of all, we need to talk about London. Are you staying? Are you going? Are you coming back to Los Angeles? Do you hate the States now? What's the vibe? I'm here for good. Speaker 2 (3:57) People are like, why did you leave LA? And my answer is, I moved to London. And I had to leave LA to move to London. But it wasn't like I'm over LA. Speaker 1 (4:06) Now when I go back to LA, I don't. I know I don't want to Speaker 2 (4:09) live there and I don't know if I'll ever want to live there again. I don't like New York and I couldn't live in San Francisco. So I just fell in love with London. Why do I live here? Because I like it. Like that's the complete answer. You Speaker 1 (4:24) are kind of the pioneer. Oh, thanks. Of so many things like fashion, venture capital, being a female in Silicon Valley. I hate to say it, but girl boss. Yeah. And I think that people today are really – what I hope that people take away from this is that they can feel more like an insider maybe in outside spaces that make them feel like they don't belong. I think really understand the power of control, branding, money, and just reinventing yourself and constantly taking like what you've done really well and doing it over and over and over again because you are kind of the pioneer. Speaker 2 (5:04) Thank you. Yeah, I've had some reinventions. And I think, yeah, my story is, right, the Girlboss book was just my story of being a community college dropout, starting an eBay store and building a business that did $100 million in revenue. It's like, if that's not relatable, I don't know what is. And so I've kind of found my way in the back door, side door, I don't know, to so many things. And that's what makes it fun. It's like... I found myself qualified, but I didn't start qualified. Nobody really starts qualified. So, yeah, hopefully people take away from this that no matter where they start, they can find their way and do something that they're not qualified for because it's very possible. So Speaker 1 (5:44) you messaged me in 2022 and you DM'd me off of TikTok and Instagram and I had just started posting there and I was truly a nobody. And I remember taking screenshots, which I still have on my phone that I'm going to send to my team that we can put in a social post of like, oh my God, Sophia Amoruso just liked my post and has like messaged me. I think though that what surprises me about you is like you are, and you might not think this about yourself, I'm curious. You are such a girl's girl because for you to reach out and to give me the platform and like even post my stuff and. To feel like someone was above me to grab my hand and, like, help me get there, like, I will always credit you for that. And I'm curious, have you always identified as a girl's girl? No. I'm like a Speaker 2 (6:32) bro. I know. Like, I'm way more comfortable hanging out with dudes. I, you know, it's like, yeah, I've been the only girl in the room in a lot of places in my career, but, and I can hang. You know, it's like I can hang at the poker table, but I'm going to raise money at the poker table. Right. And it's not. Because I'm a girl, I just kind of like don't see myself as one. But there's also, I think, a privilege to that in that I didn't come up in a corporate environment. When I raised money for my company, I had already built it to 30 million in revenue. I was never someone with like a hope and a dream who was asking for something in a dynamic where men are the one in power. And weird stuff happens when power is skewed. I think because I like entered the world of... business and men and venture capital and money and power from a place of power. My experience has been different and I can bro down because I don't need I don't need anything. I'd rather just have a smaller venture fund than like pander to some dude. for money. Like, it's just not worth it to me. I Speaker 1 (7:39) do think, though, that it is still worth noting that it is the anomaly. Like, I don't think that it is the norm, because when people gain access to power, it's so easy to just use that for a self-fulfilling prophecy and a self-fulfilling mission, where what I constantly see you doing, whether it's me or other people, is like inviting them to the poker table, inviting them to the party, inviting them to the thing that you're putting on. Is that because that happened for you or is it because it didn't happen for you when you were building your businesses? Speaker 2 (8:08) Neither. Like, I think, did I get you on a panel for the Carta event at LA Tech Week? I hardly knew you. It's because it made me look good. So I wouldn't have done that if you weren't going to show up and be awesome. I think when you surround yourself with great people, it doesn't matter at what part of the food chain they are, how far along in their career they are. If somebody's impressive and you... can qualify them for the thing that you're bringing them into, which isn't necessarily going to be everything. But I knew you would be successful in that place. Or if I introduced you to somebody, for example, it's like, I'm not going to do anybody. I'm not doing anybody any favors. It's just like, it's fun to connect dots that make everybody happy and creates value for everybody. And that's what I do as an investor. And it's free. And if I can. If I can do that with something as simple as an introduction, then like everybody wins. And I get to think about my past in a way where it's like, wow, I've accumulated all these relationships, influence, expertise, right? Like a platform. And I get to be as resourceful as I always was, you know, scouring thrift stores for vintage. But now what I'm doing is seeing how far I can get with my taste in people or in a startup. and the connections I can make. And that's not that different to me than selling fashion or, you know, making a customer happy or, you know, hiring great talent and seeing people work together in a room. Like, it's kind of all the same to me. So Speaker 1 (9:40) that day we have to talk about, because I don't even think you know this, but when you asked me to speak on that panel. I had made one video to date that was like, I'm going to become my hottest, smartest, richest self. And like, that's what I'm going to do. But when they, at the day of the panel, asked me, what is the name of your company? I blanked and I went Hot Smart Rich. Oh my God. And so the first piece of merch that we can put into the video, I have a picture of it, is like, remember they made those embroidered hats at the event? Speaker 2 (10:06) I Speaker 1 (10:07) got one embroidered Speaker 2 (10:08) and Speaker 1 (10:08) it was like Hot Smart Rich. And from that day forward, the company was branded Hot Smart Rich. So you have a very big influence. Influence and me, I think, accepting and wanting to push against the grain and really be polarizing. And I think that's true from even the way that you branded both Nasty Gal and even your venture capital fund being called Trust Fund. Yeah. I want to talk a little bit about branding because I think you are a queen of branding. Thank you. How important is it to be polarizing and to stand out when you're thinking about naming anything in today's world? I think Speaker 2 (10:42) it's important. Speaker 1 (10:44) But I also think Speaker 2 (10:45) that the name of something, I think the name of something is important, but I think it's more important that you do something great. Ultimately, you want a brand that's memorable. Every venture fund is named something fund or something ventures. And to just name it trust fund, people are like, what does it mean? And I'm like, what do your tattoos mean? They don't mean anything. It's just funny. Like, it's memorable. And that's enough, right? And Nasty Gal was like. Is it about being a nasty? Like, no, I was never like, oh, I mean, there was a I'm a nasty gal. It became part of people's identities, but it wasn't because anybody was actually nasty. It was just like a word that was in front of gal that was kind of polarizing. And if you took your grandma to nastygal.com before we bought it, you would have landed on some like pretty gnarly stuff. So I guess that makes it memorable, too. Or I guess, you know. Getting a package in the mail to your office that says Nasty Gal on it, people are thinking you're buying sex toys. They hadn't heard of it. So it was polarizing and it was funny. Girlboss is the name of a film. It's like called Girlboss Gorilla. It's like a Japanese female revenge film where they're like knife fighting in the streets and riding motorcycles and like, you know, terrorizing men. Good Speaker 1 (11:52) brands just kind of come out and it's like, great, that. Speaker 2 (11:55) You know, people talk about manifestation. I'm not the expert to talk about that. I can will a lot of things into being and sometimes just naming them or announcing them. I'm starting a media company. It's like, oh, shit, now I have to figure it out. After I left Nasty Gal, I was like, I'm doing a conference. I never put on a conference. And I was like, I'm selling tickets. And it sold out. And I was like, oh, shit, what is a production company? How do I do this? OK, I got to get sponsors. I wasn't in the media company business, but just like. You say it and you figure it out. We Speaker 1 (12:24) actually had an AI specialist come on and we did a little exercise where we said, what would you say for advice for Maggie to build a business today? Like you're just starting from scratch to the AI. And then what would I do? And the AI actually said, sell the thing before you have it. Like put the ad out and see if you have a market or create the content with that tagline the same way I did with my first video of Hot Smart Rich. It went viral. to my level of virality. And I was like, oh, there's something here. I must make this into something. Who do you believe has some of the strongest branding in the marketplace today? I mean, the best brands Speaker 2 (13:00) become part of someone's identity. And I did that twice with I'm a nasty gal. Like people said that I'm a nasty gal. And then people said, I'm a girl boss, right? That's the ultimate kind of aspiration for a brand. I invested in Liquid Death. And it's a canned water company. And on the cover, it looks kind of heavy metal. It kind of looks like a beer can. But at the end of the day, they're selling something. You can buy all kinds of clear water in a bottle. And the water is very good. But if you can turn clear liquid into a brand that people identify with, I think that's pretty impressive. In terms of brands that have emerged, I'm just thinking about the kind of things that I wear and use. You know, anything that becomes a calling card for, you know, who you are, your taste or how you operate with software. It's like some people think Cloud is better. Some people think ChatGPT is better. Some think that some of these companies are, you know, one's your friend and one's like the Death Star. Speaker 2 (14:06) You know, and that's just all the way a company is perceived publicly or in the media or the kind of thought leadership that they put out. I think in some ways the way people used to wear logos on their sweatshirts, it's now the way we talk about the software that we use, which I think is really interesting because it was no one was like, oh, my God, I use Gmail. Speaker 1 (14:25) Don't you think it's so much harder to do that, though, as a tech product than it is as a brand? Like, Speaker 2 (14:30) I think Granola became cool because it felt. Somehow like a secret. And I don't think that was intentional. I don't think that was, you know, a marketing thing. I think it was, OK, it's a