Stop Destroying Your Network: Sophia Amoruso On Killing Girlboss & Building Her VC Fund

Success does paint a target on your back, and I think women kind of can't win. So like, the red lip is in. Red lip sticks out. Go into the office. Work remotely. Make a decision for yourself. Try something. Go 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 NastyGow, 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 could women start using AI to actually get ahead? Like, do you have a favorite promise that you use all the time? That's not what I told you. Stop using M-dashes. It's not this. It's that. Don't ever use that again. Those are the promises I use the most. People feel like there's some silver bullet or big playbook. I think it's important to remember that all it takes is one serendipitous thing to happen, one relationship. What are the frameworks that you would tell people of, like, investing 101? What really gets you excited? Hi, Angels. Did you know that subscribing to our channel is free? It doesn't cost you anything, and it is the simplest way for you to support HotSmart Rich and help us grow, so that we can bring you more of the conversations you love. Just hit the subscribe button below, and thank you. In case you missed it, you're allowed to be hot, smart, and rich, so let's get into it. So, famer or so? 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, but what we're going to talk about today? I don't know, because I have a lot of life experience, and I'm maybe funny. You are fanned. There's probably something to learn here. Usually there is. I know you as a friend, first, but you are the founder of NastyGal, 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 Sophie Emma Rousseau? Sophia Emma Rousseau 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. Boothstrapped a company to 30 million in revenue, called it NastyGal, wrote a book about it in 2014 called GirlBoss, 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 substack. 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 great proximity to Europe. 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. 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. Now when I go back to LA, I know I don't want to 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 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 girlbos. 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 an outside spaces that make them feel like they don't belong. Yeah. 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. Thank you. Yeah, I've had some reinventions, and I think, yeah, my story is, right, the girlbos book was just my story of being a community college dropout starting an eBay store and building a business that did a hundred million dollars 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. And 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 you messaged me in 2022. And you DMed me off of TikTok and Instagram, and I had just started posting there. And I was truly a nobody. And I remember taking screen shots, which I still have on my phone that I'm in a send to my team that we can put in a social post. I've like, oh my god, Sophia Emery, so 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, but yourself, I'm curious. You are such a girls 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 girls girl? No, I'm like a bro. I know. 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 gonna 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 and 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 in a dream who was asking for something in a dynamic where men are the one in power and weird stuff happens when there's, 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, panor to some dude for money. Like, it's just not worth it to me. I 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? Neither. Like, I think, did I get you on a panel for the card that I've been 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 introduce 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, 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 making a customer happy, or hiring great talent, and seeing people work together in a room. It's kind of all the same to me. So 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 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 when 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. It's like, remember they made those embroidered hats at the event. I got one embroidered and 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 in 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 it's important. But I also think that the name of something, I think the name of something's 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. It's memorable. And that's enough, right? And nasty gal was like, is it about being a nasty guy? 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 brands just kind of come out and it's like, great, that, you know, people talk about manifestation. I'm not the expert to talk about that. I can, 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, no, I have to figure it out. After I left nastygal, I was like, I'm doing a conference. I never put on a conference. And I was like, I'm selling tickets and it's sold out. And I was like, oh, shit, what is a production company? How do I do this? Okay, 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 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 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 and 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 like 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 chat GBT is better. Some think that some of these companies are, you know, one's your friend and one's like the death star. Like, you know, and that's just all the way a company's perceived publicly or in the media or the kind of thought leadership that they put out. I think it's 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. Don't you think it's so much harder to do that, though, as a tech product than it is as a brand? Like, I think her nulla 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, okay, it's a startup out of London. People are starting to hear about it in the US. Somehow they built a product that felt friendly enough where it wasn't like espionage. Like, it is kind of weird how normal it is that you were recording calls and having AI transcribe it for us. But five years ago, I think people would be really mad if they knew that that was happening and now it's kind of normal. I think like the best software does that is where it's like, it's meets you where you are in terms of its marketing, but also shows you a better version of yourself. Like, that's what I did with Nasty Gowt was like, it wasn't a motorcycle jacket. It was, if I buy this motorcycle jacket, I'm going to take over the world. Like, this is a vote for my more confident self, even before it comes in the mail. Like, I just voted for a future that's going to make me so much more hotter, smarter and richer, right? And I think when someone lands on a website for a software product, they should see a version of their self. It's like, I'm going to be move faster. My company is going to be more efficient. I'm going to make more money or I'm going to save money or I'm going to manage my team better or whatever those things are. The website should feel like an unlock to a better version of yourself with a user experience that is as simple as possible. I'm so curious to bring it back to like 2016 era of the Girlboss. How did you come up with Girlboss? I mean, it was just a book. It was, you know, I can only do things if I have it in me. Like, if somebody assigns me a task, like write a second book, which I've tried to do, it's just like, it's not, it's, unless it just comes out, it's not great. And I was like, okay, I've got this story. People seem to think it's pretty novel. There's a lot of things, you know, I had had press, but there was a lot of things that I hadn't talked to the press about that I wanted to tell on my own terms in a book. And it was an unlikely story. And it was, I think kind of like a first of its kind in the business book section where there was a young woman who was kind of cool and edgy and was talking about business and ambition in a way that didn't feel like stale, like the kind of advice your parents would give you. Or someone who had a pedigree who was the chief operating officer at a, you know, multi-billion dollar tech company. It was a time where a lot of people didn't consider themselves business people, a lot of women hadn't seen business women who weren't like wearing the pencil skirt and the hosiery and the pumps and all the things that we thought we needed to look like or emulate in the workplace. Software was emerging for people to be freelancers, work for themselves, the creator economy hadn't even really emerged yet. But there was this burgeoning movement of people who wanted to work for themselves or start businesses. I think it was just like, okay, I'm going to show people what I did and through that I can give them really old school advice. It's like work hard, be nice to people, embrace yourself and be weird if that's who you are. If that advice had been given by your mom and dad, you'd be like, whatever mom and dad, because I was delivering it, I think it landed in a different way and is a very relatable story. It was also a good name. We marketed it really well. Nassiel did put marketing power behind it. We had billboards on the way to Coachella that said, you don't need a wristband to be a girl boss. We had taxi cab toppers in New York that said when 800 girl boss and there was a hotline. I mean, I hired the best PR team in the world that got me on to like every live TV show and podcast and news channel, local news, book tour. I mean, promoting a book is no joke. It was like every possible channel that I could promote the thing on I did. So that's part of it. And then you got to the point where in 2022, you said, please stop using the word girl boss. Thank you. Do you remember it? I mean, oh, funny. I mean, it's just like, what were you 2022? I mean, I think it's just funny. I mean, it got legs, right? Then it ran it ran off like really fast. And it became part of the zeitgeist. I mean, there's baby onesies that said girl boss for every 21 head shirts that said girl boss. Britney Spears is a shirt that says girl boss and it became like shorthand for ambitious woman. And it changed over time, but it was no longer mine. Like after 2014, 15, I don't know, I think 15 was maybe the paperback tour. It became part of the zeitgeist. And I was like, great. I'm the originator of it. But like you can attribute it to me, but like stop blaming for me for whatever permutation. It's become in culture and media because like I wrote a book. And I was part of a period of female founders that were, I don't know, all building things at the same time. But I've had so much time to move on, but people are still examining it. Like, what does it mean? The girl boss industrial complex, the end of the girl boss, girl bosses back, snail girl culture. I don't fucking like, "This is sleeping out of it." - It's just so funny because I think in culture right now, it's so easy to become a creator. - Yeah. - Solopreneur, really like these business intellectual influencers that are coming. There seems to be this resurgence of like the female founder, the girl boss, and I feel like it's getting such a bad rap, whereas for me, I think it's okay for women to be ambitious, to be driven to like go and try to achieve things that the men have never had a problem doing. But I'm curious for you as someone that is on the inside and did develop the word girl boss, like how do you feel about where we're at in culture right now for women? - Honestly, I think women kind of can't win. I think if you work too hard, you're overly ambitious or you're propagating hustle culture, but that doesn't work for everybody. So how dare you represent yourself and non-clude everybody in the conversation? And if you're talking about the way you do things, and it's not the way other people want to do things, just because you're in a public position or people are watching you, and maybe they don't relate or don't want that, they're gonna be like how dare you. But it's like, just figure it out for yourself. If being a hot smart rich or being a girl boss or working hard or hustling, isn't for you, then just do something different. I think the narrative of women having to be ambitious or having to work hard or women wanting to have a softer life and not wanting to grind, like all of those things are fine, they can all happen at the same time. I don't think the way women live their lives needs to be a trend, right? And I think this comes in cycles and it's never ending. It's like if the red lip is in, red lip sticks out, go buy red lipstick, it's just like people are gonna sell us the same thing over and over to tell us how we should be. And I think it's just kind of the history of being a woman and it's what we haven't been told to do is what's right for ourselves. And I'll take some responsibility as you know, I've looked at the book since it was published and it's like, I am telling people how to be and how to work. It also says to take this with a grain of advice and make decisions for yourself. If it's not right, people don't want that. People want to cling to frameworks. It's why religion is so popular, it has been forever. People don't want to think for themselves. And they want to go cling to someone else's story and emulate it or they want to buy a book that tells you, if you do these things, you're gonna have success. Don't go into the office, go into the office, work remotely, right? Like, make a decision for yourself, try something. Change your mind. It's not the heart, right? You're gonna have an opinion, not everybody has to listen. Go watch another podcast and shut up. Like that's it, like chill. This is my life. It's not your responsibility. You're just one voice among many and if it lands great and people will be inspired by you. And if it doesn't work for them, that's okay. But they don't have to feel bad about themselves. They don't have to angry about it. They just go find another podcast. Go for read another book. I love you. I've always understood why people are interested in crypto but I'll be so real. 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Especially if you have a partner that sleeps in your bed with you. For me, I'm complicated. I fall asleep when I'm freezing. I ends up getting burning hot at night and then I wake up freezing again. So having a temperature controlled mattress like my eight sleep pod is critical. So I want you to try it for yourself at 8sleep.com/HSR and use code HSR for up to $350 off your order. That's what I've always loved and respected about you is like you really do things early and again for grain and then even when you're met with something, you're like don't care, don't listen to it. But it's very hard to do that in practice. Is that what you were like as a kid? I think so. I mean, things hurt, right? People have said a lot of things about me. They've said a lot of things about girlboss and I'm going to girlboss my way to the sun or blah, blah, blah. And, you know, she's amazing. The poster trial for entrepreneurship and she's a failure. And, you know, whatever. And it's like, it's not like those things don't land. Like, I've had a lot of hard times and I still feel like an imposter plenty of the time, right? I'm a venture capitalist right now. And people are asking me about like enterprise AI and orchestration layers. And I'm like, I can't answer all of those questions. Like, actually last minute ditch to podcast recently because I saw the brief moments before and I was like, I'm going to choke. I can't fake my way through answers about this. And I would rather do that. I feel awful. I was like crying like I'm such a loser. But I've never done that. But, you know, we find success in different places. And it's not like I haven't listened to what's been said about me. It's not like I haven't read the criticism of whatever it is than that flex series or the book or girlboss over the 12 years since it was published or, you know, and I still feel it and it can hurt. But just as many people are like stoked to chat with me. Yeah. And I still have the access that I always had. And I still have all the things that I learned. It's like what I know and the value I have created and can continue to create is only something that I know. Like, the people can be like, when I have girlboss, but my DMs 12 years later are full of women being like, oh my god, thank you, I read you. When you're chasing me into the grocery store, like getting up from a cafe table, like I saw this girl clock me in my neighborhood walking by this restaurant with like cafe tables. And I went into the grocery store where I'm probably pajamas and this person appears and she's like, oh my god, it's just, it's like, nobody's writing a headline about that. But like, I know the impact that I've made and it's still really gratifying. So I get to see that. And I see it more than any kind of like, flack that I've gotten. But no, I've always been, I've always felt like an outsider, but it doesn't necessarily get easier. But when you find where your talent lands and you create value for people and share your story and it makes them happier, they learn something and you get that feedback loop, then you start to feel like you belong a little bit more. I think it's important to remember that all it takes is one relationship. All it takes is one serendipitous thing to happen. It could be, it doesn't have to be in a meeting. It doesn't have to be at an Andreessen Horowitz cocktail event at LA venture week. It can be at dinner with some friends and some other person tags along that's doing something interesting and you say, hey, look to learn about that. Or you just become friends. and then you meet other people and they're like, "Hey, let me show you this world, right?" Like, as you put yourself out there, the world opens up to you, but you have to put yourself out there, right? Like, I had this boyfriend that did a lot of DMT, which is a psychedelic, and he said he saw probability cats. And he saw that's crazy. - Probability cats. And it was like cats jumping in every direction. It's like each cat spawns more probabilities. And so I've always had this kind of visual of, yeah, like you do one thing, and you have no idea how many more probabilities that creates. You do two things. How many more possible things can that spawn? And it could be that you learn something, it could be that you meet someone. If you don't say yes, or you don't show up, whether you're invited or uninvited, or whatever it is, try different things, you're not gonna find where you land, you're not gonna find your people, opportunities aren't gonna open up for you. If you don't DM that person, if you don't put yourself out there, and show who you are, that person's not gonna DM you, right? I wouldn't know you if you hadn't done that. You wouldn't be here if you hadn't done that, right? And it's just like, it's bit by bit, and nobody starts as an insider. - Do you agree with that saying, "Men, your net worth is your network?" - Kind of, kind of. I hate it, you know, it's like, but yeah, yeah. I never hang out with people because of their net, their net worth. Being like, networks are important, hanging out with someone powerful, or influential, definitely opens doors. But if I don't like somebody, I'm not gonna go hang out on their boat, hoping they invest in my venture fund, it would be torture. I'm just, I can't pretend, I'm not, I cannot pretend to like someone or enjoy myself, and I'm not willing to do it enough to get more or extract value from people. So that's the place where I would say, like, don't do that. Just make sure that you like the people who might open doors to opportunities, and don't put yourself around people that aren't nice, or treat you like shit, or fucking weird, right? I'm like the wrong kind of weird. There's like weird, and then there's like fucking weird. And when I say that, I mean, like, mm-hmm. (laughs) You just posted a video saying, everyone tells you how to build your network, but no one talks about how you destroy it. How does someone destroy their network? I mean, you destroy your network by making introductions that aren't qualified, right? Like, I'm not gonna introduce you to, I don't know what a rocket scientist and say, hey, you guys should do something great. Maybe they have a startup, like, I'm not saying, my friend Frederique is actually a rocket scientist, but she invests out of Google Ventures, and you should probably-- - A little better team. - Yeah, yeah. - We have co-invested in Alara together. - Okay, cool. - Yeah. - Yeah, she's amazing. You don't need an intro to her. But, you know, it's like, but is this gonna create value on both sides? It doesn't do anything for anybody to make introductions or connect people who aren't actually gonna connect. If the person is not ready for the introduction, that's so nice. You're a really nice person to make, to offer an introduction, and maybe you're trying to prove your value by putting somebody in touch with a more powerful person, but if that resource doesn't land, or whoever it is that they want an intro to, doesn't want to have a second phone call, or isn't interested in what they're doing, or just want to have a first phone call, honestly, then you're wasting that person's time, you're wasting the other person's time, you're getting their hopes up, and ultimately it erodes your reputation, because the next time you try to make an introduction to that person, you should, you know, they're absolutely gonna say no. So it's your job to protect the interests of the people in your network, you know, the people who are coming up, and who you could help by making those introductions, but just know where it's going to create value. You know, it's like even if someone is in a position where it's like, I don't wanna introduce people to just pick each other's brains. - I hate when people say I wanna pick your brain. I'm like about what though? Look out, we wanna protect my brain. - Yeah, I mean, I just, I say no to most intros, like even warm intros. It's like, hey, this person is starting a business where you can virtually try on clothes. Like I did e-commerce for 10 years, nobody's figured that out, right? I'm sorry, like, I'm a girl's girl, but no, like, it's not gonna go anywhere, so why waste anybody's time? - Okay, speaking of that, because I love, before I interview someone, I actually go to Google and I'm like what are, what are people searching for? And it's so funny, most people is often like, person's name, parents, person's name, wife, person's name, net worth, person's name, whatever. It's the person's name, age, always. But with yours, it's actually like, what does Sophia and Marisa do now? And that was actually what I was like, so excited to talk about, because I feel like yes, you're known for nasty gal and girl boss, but actually what you're doing in the investing world is like so fascinating. And it's one of the questions that I get asked the most, like, is like investing in the frameworks and like the companies. And so I wanna start the conversation with something that like, just only Sophia and Marisa could answer in the best way I think, because you've navigated entertainment, venture capital, retail. Are you feeling the same sense of like, this ground swell of like, creator investing and celebrity investing in everybody wanting to get on cap tables when they're like famous? - I mean, I see it for sure. I think it's great. I think it's great that people are building brands that can help amplify a startup and create value for them and get to participate in the upside. You know, it's like Hollywood, brand partnerships, things have been transactional for so long and they're one off. It's like, great, you get paid to talk about the thing, but if a creator or celebrity is actually really excited about investing in something, they're gonna put more into it than, you know, getting paid to shell a product, right? And they're gonna have a much longer approach to how they can support that company. I mean, I think Steven's a pioneer in that, right? And he's built a whole media company to, yes, entertain people, but also he's investing in companies that he can use his platform to support. And there's just, there's a whole ecosystem around that. And, you know, if you build a personal brand or you put yourself out there and people follow what you do and there's trust with your audience, you should absolutely use it to every advantage that you have to support the things that you're interested in. And if you're interested in them, the chances are that your audience is gonna be too. So everybody wins. You're not just promoting a thing because some brand came to you with an RFP saying we want one real three stories. And we want you to repost it to TikTok. It was 30 day, you know, paid usage and 90 day organic usage and some kind of bullshit. It's like, it has legs in a way that brand partnerships don't. - But as someone that's written a million dollars personally into angel companies, so you've done my favorites that I picked out eight sleep, superhuman, public, liquid death, loveable. These are all who I would think of as winners in their category. A lot of people are gonna start thinking about investing these private companies and not know how to pick winners. And so it becomes actually like a really hard way to make money. So for you, first of all, out of those companies, who do you think will go all the way? - I mean, loveables like a rocket ship. I mean, loveable is making it possible for anybody to build anything by chatting. And it's crazy 'cause I still know people where I mentioned loveable or even, you know, chat GPT or whatever. It's like they don't know you can build websites by having a conversation with AI. They're still using AI like a search engine, right? Like perplexity, which was a search engine, felt like kind of a search engine. Like you can build like complete apps in it. Loveables not the only place that you can do it, but what they're doing for people who are building software, even e-commerce business owners have to build software, even if their primary business is in physical goods, is what eBay did for me. Like it's so powerful to me what AI is doing and personal to me because it democratizes opportunity for people in a way that like an early marketplace did for me by giving me a place to like punch in product description and list of vintage item and start a business. And so I'm very, very excited about where that's headed. Women are unfortunately adopting AI at 25% less rates than men. What would you want every woman listening to this that isn't using AI to do tomorrow to actually get ahead? I'm posted about that and I got so much blowback. What is this? Is this a cabal? Mel Robbins posted about it, Reese Witherspoon posted about, is this some kind of like evil AI thing where, you know, don't tell women what to do, honestly? Like, I am so done telling women specifically what to do. But in terms, like, it's, I got like skewered. Women really, and I think 11,000 people unfollowed me when I made my first post about AI. And it was, you know, I found out this to, I hadn't seen Reese Witherspoon's thing. I wasn't getting paid for it. They were like, who's paying you for this? You need to be transparent about it. And I was like, no, I'm just using it. And actually, if you're not using it, I do think you're gonna fall behind. That's an opinion that not everybody necessarily shares. But I feel like I can share the way I use things and how it's getting me ahead. And people are fine. If I say, look, I built this thing. If I said women should build this thing, they'd be like, fuck off. So the way people can get ahead, and because your audience is women, and my audience is women, if I talk about it, right? The people who self-select and find it interesting, might listen, is just use it. You know, follow newsletters about AI, like follow me, follow people who are talking about it in a way that's really relatable. You don't need to follow the most like technical people, follow @gbt, right? Like, she was on the podcast. That's why I was asking because one of her episodes is one of the top performing, and the number one save clip that we have is her number one AI prompt. Do you have a favorite prompt that you use all the time? Stop using M-dashes. It's not this, it's that. But I already told you that. What the fuck? Like, that's, those are the prompts I use the most. As amazing as AI is, I'm still yelling at it, and I'm like, we already talked about that. Reference the other thread. AI can be frustrating. I do feel like sometimes it can make things take more time than just doing it. How do you recommend women be smart about money? I think being smart about money is saving money. I think debt is, I just, I have a credit card, but it's only so I can get points, and it's more secure than spending with a debit card 'cause it's connected to your bank account, but I've never been in credit card debt. So I would say use a credit card like cash, pay it off every month, where you can, own your business, don't prove reliant on other people for money, and then you'll put yourself in places where you can make decisions. I think saving money early is important, and then once it's saved or you're further along in life and you know kind of income that you have, or maybe you feel more secure, you can figure out what to do with it, but the earlier you start saving the better. And I would say don't get carried away with Birken bags, like that's fine. Like it's okay to splurge on things here and there that make you feel like a better version of yourself, but getting wrapped up in the optics of being of wealth, I think is a really dangerous thing to do, and definitely not worth spending your money on. I would say coffee's worth the money. I'm generally just saying that coffee's worth the money. - 10 years ago, you were named one of the richest self-made women in the world by Forbes. - I know, that's crazy. - It is crazy. - Do you think that people treated you differently? - No, I don't know. 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Sign up today to set up your funnels and order bumps and get started with a 30 day creator pro-trial at link.stan.store/necky. You were probably one of the youngest, richest self-made women in the world. And I loved the post that you just did about the eight things that people don't tell you when you're successful early on. I wanted to ask you about three of them. Success paints a target on your back. Proximity to power isn't the same as friendship. And success amplifies who you already are. What do those three mean to you? Yeah, I think success does paint a target on your back because people are looking at you. They're looking to you as an example. When you're successful, people think that you've got some secret that they don't. And they're looking for all of the clues. And maybe they've outsourced a little bit of their story and their way of getting there because they think that if they emulate you, that's going to get them there. And you can be inspired by other people. You can't replicate somebody else's story. We're all going to have our same story. But when people build you up to be this icon and you disappoint them and they're like, oh my God, the girl boss, her employees said that it's a toxic workplace. It's like, okay, some people didn't have a great time working at my company, but it doesn't mean that I'm not a great person or I didn't do my best. When you're put on a pedestal the way I was and you're seen as the millennial poster child of entrepreneurship or the female millennial poster child of entrepreneurship and you let people down, they're like, who do we look to? Or you, this is personal, like, you were my north star. So if I don't have that, like, where am I going to look now? In the same way that when someone's really excited about a brand, like, people were obsessed with Nasty-Gow. If their package came lead or we sent them the wrong thing, it was like their friends stabbed them in the back. Like the level of anger people have when they are like hyped up on something. And it doesn't work out or they don't get what they thought they were going to get is like personal. And so me not being the example at every moment of what the girl boss should be, whatever that was that people projected onto me, certainly put me in a place where I was ripe for criticism because when you stand for something where you're almost like a caricature of a thing which was like, girl boss. And something happens that stands in contrast to it. People will hold it against you. And I think a lot of female founders experience it. I don't think it's uncommon. I don't think it's necessarily something that we're all going to escape. I think it's just a matter of knowing that that can come with the territory. And hopefully people have seen this enough to know that at some point they're coming for all of us. Like at some point, if it hasn't happened to you, probably gonna happen to you, what's the headline? Whatever, it'll sell something, right? Like I sold magazines when I was a girl boss and fast company sold clicks for advertisers when the headline was, does the failure of nasty-gal mean millennials aren't ready to lead? Like am I the what? Just because I didn't pull it off or I wasn't perfect. That means that an entire generation, what? Right? So somebody's always making money somewhere by saying some kind of bullshit. - That one just stuck out to me because even yesterday, I remember I was on the phone with my team and I was like, I'm held to a higher standard than other people. And whether it's because Steven invested or because of even the family that I'm a part of, I do feel like there is like I'm held to a higher standard than other people and that scares me because I think the people that I want to emulate or that I find inspiring are the people that like when they're at the top, they're constantly reinventing themselves. Like, they don't get comfortable with what they've done the past, they're always trying to push the envelope. But when you do feel like there's a target on your back or like, people are watching you. It is harder to keep pushing yourself. And I think that's like, truthfully what drew me to like, you in the first place. Like, yes, of course, it was nasty gal, but it's also like everything that you've done since then. And I think especially with the investing side of things, the companies that you're in, the fact that you've invested in over 50 companies, like, you have points on the board. You have all these winners. It's like, that's the story that I find so interesting and so inspiring because life is long, right? And like, hopefully your first business sells within the first seven to ten years. Maybe it does. Maybe it takes a bit longer, but there's so many different chapters that we're all going to have. Like, on the investing side, that's the question that I get asked the most, truthfully, from like the dedicated angels, they are like, what is the framework? What are the red flags? And so what? I have an expert in the chair of like, someone who's lived and breathed this for the last few years. Like, what are the frameworks that you would tell people of like, investing one on one? And then what are the absolute red flags of things where you're like, immediately, I will never invest money in your company. I think number one with investing is don't invest more money than you are willing to lose. So if you're an angel investor, you're probably investing in an early stage company that is unproven. And even if it is kind of proven, anything can happen. It doesn't matter how big a company is. And these are high risk investments, right? It's not putting money in the stock market. Your money is going to be locked up for a long time. There is no liquid market for private company shares. You invest in this company, expect it to be stuck there for 10 years. You can't pull it out. You're not going to invest that $10,000 in a house three years from now. It's stuck there until everybody gets their money back. And that company has to sell or go public. And that usually takes a long time to happen. Invest in things that you understand, invest in things that you would use. I mean, when you're getting started, it's like, okay, if you would be the customer, then it's definitely a green flag. I think founders are really, really important, especially at the early stage, because a great founder can pivot. I like second-time founders a lot. You're looking for someone who's either worked on the problem or they've been inside a company where they're seeing people experience the problem and they know they have an idea of how they can solve it. The angel investing is just important to start small, right? I mean, some companies will say the smallest check will take its $10,000. If you can't afford $10,000, don't get all hyped up and don't money that you don't have or can't afford into a company. So I think be mindful and start slow. And red flags is like the overconfident founder who's just like, I don't know. Someone who gets on the phone and knows nothing about me, like I've had people and like, it's fine. You don't, like, Nasty will happen a long time ago. You might be 25 years old. That's fine. But don't get on the phone with anybody that you haven't done some research on. So I think that's a red flag. When there is a valuation that they invented, but there's no lead and they're just kind of gaming people off each other, like all these people are interested, but they can't name who they are, they won't name who they are. The valuation keeps creeping up. Okay, you said it was 50 million last time, but now it's 60 million why. And then if somebody already has investors and they're going to raise a subsequent round, if those investors don't want to continue investing, it can be a red flag that there's something that they see and they don't want to keep putting their money into the business because they're like, you know, they're monitoring it. It's not maybe it's better that they put their money somewhere else. The existing investors aren't continuing to invest that can be a red flag and that happened to me at Astigal. It made it really hard to fundraise. When you're investing in a founder, one of the three things that you absolutely look for that they have to have to invest money in them. They are hell-bent on solving a problem that they've either experienced personally and want to fix, or they've been inside a company and seen the challenges that the customers having or what that opportunity might be and have a clear vision of how they want to solve them. I like founders who are like cockroaches who are just never going to go away. They're going to keep showing up whether they're asking me for money and I haven't invested in them or if I have, they're going to keep asking me for things. Ideally, there's a point where the company's much bigger and they don't need me and they've graduated. But in early stage companies, you need to be using every resource that you have. I invest because I'm a resource and it's really fun and I want to flex that and I want to because it's very gratifying for me to use my experience and see what connections I can make so I wouldn't you use me. That's the whole reason you're taking my money. The third thing is founders who are willing to take advice. They don't have to take all of my advice. I'm not going to be offended if you don't do what I suggested. I think that's crazy when people behave like them, but they have to be open. The first question was they have to be a visionary and hellbent but they also have to be someone who's malleable enough to listen to their customers, change the plan based on what they might be hearing, hear from people who might have more experience to help them see around corners see know that they don't have to be an expert in everything day one. So that's the combination of things and generally just someone I want to be around. I agree. Okay. So, Femura, so we have to ask you some rapid fire. Okay. What is the last thing you put on your credit card? Everything. What's the last thing? Coffee. What's your order? A cappuccino with whole milk. What's the last most expensive thing you put on your credit card? Maybe this ring, snelly cacao ring, my friends brand, this is expensive. Yeah. That's gorgeous. Yeah, thanks. What's the company you passed on investing in that you regret? It was a sub-stack. So Andrew Chen from Andrewson introduced me to the founder. They were raising around that was I think flat to the round prior. This was a few years ago and I could have probably gotten like a hundred K check in or so I would have been an angel check, but I didn't and I don't know if they fundraised since that's not the point, but they've I know they're killing it, right? I know something's going to happen there, so shame on me. What's the most amount of money you've ever put into one deal because you just had a hundred K there. The biggest check I've written is $250,000 of my own money. I'd say the best deal I ever did. I didn't even invest. I got advisory shares in 2017 in a company called Passport Shipping and it was just two guys that reached out to me cold. I don't even remember what their background was, but they were like we want to build the software layer that makes it easier for e-commerce businesses to track international orders because and for a decade at nasty gal, we would send something internationally and it just went to avoid like it was one carrier handed it off to another carrier and then it was like where is it? There was no way to figure that out. It was awful for customers, it made us look awful for customer service and so I was like I don't really angel invest, I don't know, but they gave me some advisory shares. It took nine years 2016 now and I just made 500 grand just like making some introductions along the way. I mean they're grateful, I actually did put in work and they're happy, they weren't like why are you scammed us for free equity, but like that's what can happen over 10 years. But I think that's the most interesting thing because I don't think you would have gotten those advisory shares, had you not been the founder of nasty gal, right? And even though it's like you've said a lot in this interview or even as a friend, you've said like oh well, I was the poster child and then I wasn't what people lived up to but actually what you're doing now is all partly because of your time at nasty gal, and like I have here that nasty gal was one's valued at 350 million and you owned 80% of the company which technically made you worth on paper $280 million. Obviously that went away, but you're still making half a million dollars because you were the founder of nasty gal and that's just one thing that you're doing. And because I can pick winners. Yeah, because I can make an impact on them too. But yes, I will forever be writing in the co-tails of what I did at 22 years old. And so to see like the fruits of my labor that I never thought would be fruits because I just had my head down is extremely rewarding. And you only get to experience that after a lot of time has passed. But there is a time where you know that it's time to move on and I think it's just a matter of listening and knowing that you're going to just point people, you could lose people's money. You might have to lay people off. It's the worst. But at the end of the day, it is your life. You do have choices, you should keep your promises as much as you're capable of. But when you have exhausted every avenue to make your investors hold on their money, grow revenue, you know, decrease costs, build an amazing brand, whatever those things are, when you've exhausted all of those things, whatever those things might be, it's okay to throw in the towel. It's okay to disappoint people. You have to pick one for the rest of your life. You're never moving houses again, or you have to move every single year. Never moving houses again. What fashion trend do you hope comes back? Like, are highways should pants out? Yeah, you can bring those back. I just, are they always out? No, you can bring them back. You're in there. But I wear a low, I wear low waisted pants, but I just have so many high waisted pants that out of laziness I would like for that to come back. Love. What's a luxury brand that's overrated? Honestly, the quality of mimeo bags, walking into their store, I was like pretty kind of disappointed. So I went to Balenciaga. Okay. Paris or London Fashion Week? London, I don't like Paris. I'm not a Paris fan. That's crazy. What is a fashion trend you would end right now? The teenagers wearing giant sweatpants, like just like sloppy style that ruins somebody's like physique. Like why would you ruin your physique with just because you're following a trend? Like, I don't know. Okay. Yeah. Okay. If you were to title the season of your life, what would it be called? Lime bike. Lime bikes and what else do I do a lot? I don't know. Lime bikes and Euro summer. Of it. Okay. If you tell yourself one, age or love note for the rest of your life, what would it be? You're always going to land on your feet. Love that. Sophia Emmerizo, thank you so much. Where can people find you and how can it ages are help you? Sophia Emmerizo at everything. Trustfund.vc, pitch me. How can you help me? I don't know. Get cool founders to pitch me and make some content that I can share because it's really hard and hopefully this throws off a lot of clips. Love it. Thank you so much. Thank you.