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

How do you pivot from building a multi-million dollar e-commerce empire to starting a venture capital fund…and why is AI the ultimate tool for female founders? Iconic entrepreneur and investor Sophia Amoruso (founder of Nasty Gal, Girlboss, and venture capital firm Trust Fund) sits down with Maggie Sellers Reum on Hot Smart Rich to spill all her investing secrets. In this episode, Sophia reveals how she uses AI tools to gain a competitive edge, why "Girlboss" culture evolved, and the naming tip for all her companies. Maggie and Sophia break down high-level business strategy, networking rules, and how to scale brands. Sophia shares how she bootstrapped Nasty Gal to $30M in revenue, built a powerful network that survived bankruptcy, and transitioned into angel investing and venture capital. Plus, she reveals what she looks for in startup founders, why being a "cockroach founder" guarantees survival, and how successful women navigate public criticism while building elite wealth. Get unselfish access to insights that will help you own the room. Sign up now https://linkly.link/2jPXJ ⸻ Timestamps: (00:00) Intro (01:55) Why Someone Should Listen (04:24) Sophia Is a Pioneer (05:44) The Power of Being a Connector (09:40) How to Build an Iconic Brand (16:01) How Sophia Created ‘Girlboss’ (18:40) Why ‘Girlboss’ Is Dead (19:45) Women Can’t Win (23:41) SoFi Ad (25:00) Eight Sleep Ad (26:22) Dealing With Criticism (29:31) Networking Tips (31:15) Building the Right Network (35:07) Creator Investors (37:54) Sophia’s Angel Investing Strategy (39:39) How to Get Ahead With AI (41:30) How Sophia Uses AI (42:12) How to Be Smart With Money (43:35) How Wealth Changed Her Relationships (43:55) Bilt Ad (45:01) Stan Ad (45:57) Three Truths About Success (51:00) Investment and Business 101 (54:24) What to Look for in a Founder (56:14) Rapid-Fire ⸻ Sponsors: SoFi - visit SoFi.com/HSRCrypto and get up to $1000 in cryptocurrency when you open and fund a Crypto account. Eight Sleep - https://www.eightsleep.com/hsr and use code HSR for $350 off Bilt - Sign up at http://Joinbilt.com/HSR Stan - https://ig.getstanley.ai/?ref=hotsmartrich&utm_source=podcast ⸻ Hot Smart Rich: Your Business & Culture Gossip For ambitious women wanting to own the room, gain power, and build wealth. Instagram: https://www.instagram.com/hotsmartrich/ Tiktok: https://www.tiktok.com/@hotsmartrich Maggie Sellers Reum: Instagram: https://www.instagram.com/maggiesellersreum/ Tiktok: https://www.tiktok.com/@maggiesellersreum LinkedIn: https://www.linkedin.com/in/sellersmaggie/ Locker: https://www.wantlocker.com/users/maggiesellers ShopMy: https://shopmy.us/maggiesellers Amazon Storefront: https://www.amazon.com/shop/maggiesellers/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Maggie Sellers Reum?

  If you're starting a business, there are certain things that are so fun to think about. Y'all know I love a mood board, so everything that relates to the creative, the name, the brand, the website, the vision board. But then there are the things that make you pause and ask, am I even doing this correctly? Or do I even want to be doing this? Like forming your business, getting the right documents, keeping your personal information private. This is where our sponsor, Northwest Registered Agent, is so helpful. They're a one-stop shop for founders who want to launch and legitimize their business without turning it into a giant admin spiral. They help you form an LLC or a corporation, act as your registered agent, and give you tools like a business address, operating agreement, website, phone number, professional email, and free guides.

• 0:43Maggie Sellers Reum?

  They also have real corporate guides who know your local laws. Visit northwestregisteredagent.com/hsrfree and start using free resources to build something amazing. Get more with Northwest Registered Agent at northwestregisteredagent.com/hsrfree.

• 1:06Speaker 01

  The action's on the court. And as the official beer sponsor of the NBA, Michelob Ultra is getting fans closer to the game with a chance to win courtside seats, merch, and more. Visit michelobultra.com/courtside to enter. Michelob Ultra Courtside, 26 to 27. No purchase necessary. Open to U.S. residents 21+. Begins on October 1st, 2026 and ends on June 30th, 2027. Multiple entry periods. See official rules at michelobultra.com/courtside for free entry, entry deadlines, prizes, and details.

• 1:33Speaker 02

  Success does paint a target on your back, and I think women kind of can't win. It's like if a 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 then shut up.

• 1:47Maggie Sellers Reum?

  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 Girl Boss, and the founder of multiple other very successful businesses. You've invested in over 50 companies. You have points on the board.

• 2:02Speaker 02

  I was 22, trying to evade working for other people. Got really good at it.

• 2:07Maggie Sellers Reum?

  In 2022, you said, "Please stop using the word 'girl boss.'" 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?

• 2:19Speaker 02

  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 prompts I use the most.

• 2:28Maggie Sellers Reum?

  People feel like there's some silver bullet or big playbook.

• 2:31Speaker 02

  I think it's important to remember, all it takes is one serendipitous thing to happen, one relationship.

• 2:37Maggie Sellers Reum?

  What are the frameworks that you would tell people of like investing 101? What really gets you excited?

• 2:47Maggie Sellers Reum?

  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 Hot, Smart, 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.

• 3:07Maggie Sellers Reum?

  In case you missed it, you're allowed to be hot, smart, and rich. So let's get into it.

• 3:17Maggie Sellers Reum?

  Sofia Emmerusso, are you ready to get hot, smart, rich?

• 3:20Speaker 02

  I already am.

• 3:22Maggie Sellers Reum?

  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?

• 3:36Speaker 02

  I don't know, because I have a lot of life experience and I'm maybe funny.

• 3:41Maggie Sellers Reum?

  You are funny.

• 3:41Speaker 02

  And there's probably something to learn here. Usually there is.

• 3:46Maggie Sellers Reum?

  I know you as a friend first, but you are the founder of Nasty Gal, the author of Girl Boss, the founder of Trust Fund, and multiple other very successful businesses. So from your perspective or your point of view, how do you describe Sofia Emmerusso?

• 4:03Speaker 02

  Sofia Emmerusso 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 Girl Boss, produced by Charlize Theron, that came out a few months after my company had fallen apart, and that was really hard.

• 4:48Speaker 02

  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.

• 5:23Maggie Sellers Reum?

  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?

• 5:30Speaker 02

  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 don't, 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.

• 5:57Maggie Sellers Reum?

  You are kind of the pioneer.

• 5:59Speaker 02

  Oh, thanks.

• 6:00Maggie Sellers Reum?

  Of so many things, like fashion, venture capital, being a female in Silicon Valley. I hate to say it, but girl boss. 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.

• 6:23Speaker 02

  Yep.

• 6:23Maggie Sellers Reum?

  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.

• 6:38Speaker 02

  Thank you. Yeah, I've had some reinventions. And I think, yeah, my story is, right, the Girl Boss 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.

• 7:17Maggie Sellers Reum?

  So 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, Sofia Emmerusso 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.

• 8:00Speaker 02

  Thanks.

• 8:01Maggie Sellers Reum?

  And I'm curious, have you always identified as a girl's girl?

• 8:05Speaker 02

  No, I'm like a bro.

• 8:06Maggie Sellers Reum?

  I know.

• 8:07Speaker 02

  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 there's, when power is skewed.

• 8:49Speaker 02

  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... Pay in or to some dude for money like it's just not worth it to me.

• 9:13Maggie Sellers Reum?

  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?

• 9:42Speaker 02

  Neither like I think did I get you on a panel for the card event 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 gonna 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 gonna 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 gonna 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

• 10:24Speaker 02

  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 scour, 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

• 11:09Speaker 02

  great talent and seeing people work together in a room like it's kind of all the same to me.

• 11:13Maggie Sellers Reum?

  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 gonna become my hottest, smartest, richest self and like that's what I'm gonna 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.

• 11:32Speaker 02

  Oh, my God.

• 11:32Maggie Sellers Reum?

  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? 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.

• 12:01Speaker 02

  Yeah.

• 12:02Maggie Sellers Reum?

  I wanna talk a little bit about branding because I think you are a queen of branding.

• 12:07Speaker 02

  Thank you.

• 12:07Maggie Sellers Reum?

  How important is it to be polarizing and to stand out when you're thinking about naming anything in today's world?

• 12:15Speaker 02

  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, like it's memorable and that's enough, right? And nasty gal was like, is it about being a nasty? It's 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

• 13:00Speaker 02

  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 well 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.

• 13:44Speaker 02

  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? What do I, how do I do this? Okay, I gotta get sponsors. I wasn't in the media company business, but just it's like you say it and you figure it out.

• 13:58Maggie Sellers Reum?

  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? It's 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?

• 14:32Speaker 02

  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 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 like the kind of things

• 15:15Speaker 02

  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 Claude is better, some people think chat GPT is better, some think that some of these companies are, you know, one's your friend and one's like the death star. It's like, 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.

• 15:58Maggie Sellers Reum?

  Don't you think it's so much harder to do that though as a tech product than it is as a brand?

• 16:03Speaker 02

  Like I think Urnola 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, we're 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. And 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 gal.

• 16:48Speaker 02

  It was like, it wasn't a motorcycle jacket. It was if I buy this motorcycle jacket, I'm gonna 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 gonna 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 where it's like, I'm gonna be move faster, my company's gonna be more efficient, I'm gonna make more money, or I'm gonna save money, or I'm gonna manage my team better, whatever those things are, the website should feel like an unlock to

• 17:29Speaker 02

  a better version of yourself with a user experience that is as simple as possible.

• 17:34Maggie Sellers Reum?

  I'm so curious to bring it back to like 2016 era of the girl boss. How did you come up with girl boss?

• 17:43Speaker 02

  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

• 18:24Speaker 02

  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

• 19:09Speaker 02

  wanted to work for themselves or start businesses. I think it was just like, okay, I'm gonna 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, but 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. Nasty gal 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, 1-800-GIRLBOSS and there was a hotline.

• 19:51Speaker 02

  I mean, I hired the best PR team in the world that got me onto 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.

• 20:13Maggie Sellers Reum?

  And then you got to the point where in 2022, you said, please stop using the word girl boss. Thank you.

• 20:19Speaker 02

  Do you remember? I mean, oh, funny. I mean, it's just like, what year, 2022?

• 20:25Maggie Sellers Reum?

  2022.

• 20:26Speaker 02

  I mean, I think it's just funny. I mean, it got legs, right? Then it, and it ran off like really fast. And it became part of the zeitgeist. I mean, there's baby onesies that said, Girl Boss. Forever 21 had shirts that said, Girl Boss. Britney Spears has a shirt that says, Girl Boss. And it became 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.

• 21:10Speaker 02

  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. I'm like, what does it mean? The girl boss industrial complex, the end of the girl boss. Girl boss is back. Snail girl culture. I don't fucking like, just leave me, leave me out of it.

• 21:37Maggie Sellers Reum?

  It's just so funny because I think in culture right now, it's so easy to become a creator.

• 21:41Speaker 02

  Yeah.

• 21:42Maggie Sellers Reum?

  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?

• 22:14Speaker 02

  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 not include everybody in the conversation? And, you know, 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 going to be like, how dare you? But it's like, just figure it out for yourself.

• 22:54Speaker 02

  If being hot, smart, rich, or being a girl boss, or working hard, or hustling, like, isn't for you, then just go to do something different. I, I think the narrative of women having to be ambitious, or having to work hard, or women, you know, 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 is, this comes in cycles and it's never ending. It's like, the red lip is in, red lipstick's out. Go buy red lipstick.

• 23:34Speaker 02

  It's just like, people are going to 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, I'll take some responsibilities. 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.

• 24:13Speaker 02

  It's why religion, it's so popular, 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 going to 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 that hard. Right? You're going to have an opinion. Not everybody has to listen. Go watch another podcast and shut up. Like, that's it. Like, chill.

• 24:49Maggie Sellers Reum?

  This is why I love you.

• 24:50Speaker 02

  It's not your responsibility. 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 be angry about it. They just like, go find another podcast.

• 25:11Speaker 02

  Go read another book.

• 25:13Maggie Sellers Reum?

  I love you. I've always understood why people are interested in crypto, but always so real. A lot of trading platforms make the whole thing feel more complicated than it needs to be. If I'm going to explore something financial, I don't want to feel like I've downloaded some random app that I barely understand. I want it to feel simple. And I want it to be through a company I actually trust. That's why today's sponsor, SoFi, is interesting to me. SoFi is the first nationally chartered bank where you can buy, sell, and hold cryptocurrency all from one simple app. You can access over 25 cryptocurrencies on a federally regulated platform with the safeguards of a bank. And because it's all in the same SoFi app, you can manage your crypto alongside your

• 25:58Maggie Sellers Reum?

  SoFi checkings and savings and investments. If you're keen to get started, SoFi has in-app guidance to help you learn as you go, so you can trade smarter. Of course, crypto is inherently risky, and you need to make sure it's right for your financial situation. But if you're ready to explore crypto with SoFi, visit sofi.com slash HSR crypto and get up to $1,000 in cryptocurrency when you open and fund a crypto account. That's sofi.com slash HSR crypto.

• 26:33Maggie Sellers Reum?

  Hi, angels. This is new, but also kind of not, because most of the guests that I have had on Hot Smart Rich have been recommending one product in their top 10 every single week. And it is the Eight Sleep. So I was very curious. I had to get one. And then they became a sponsor of our show. And it makes sense now that I've been sleeping on it for a few months. It is a game changer. You guys know that I am obsessed with getting eight hours of sleep, especially being a female entrepreneur. Why being a female entrepreneur? Because we have a different set of considerations than male entrepreneurs do. We have our hormones fluctuating.

• 27:17Maggie Sellers Reum?

  We go through so many different stages in one month period, that having a mattress that can acclimatize to your temperature is key. 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 end 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 eightsleep.com slash 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,

• 28:02Speaker 01

  The action's on the court. And as the official beer sponsor of the NBA, Michelob Ultra is getting fans closer to the game with a chance to win courtside seats, merch, and more. Visit michelobultra.com/courtside to enter. Michelob Ultra Courtside, 26 to 27. No purchase necessary. Open to US residents 21 plus. Begins on October 1st, 2026 and ends on June 30th, 2027. Multiple entry periods. See official rules at michelobultra.com/courtside for free entry, entry deadlines, prizes, and details.

• 28:30Speaker 03

  This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense. Indeed sponsored jobs can help carry the load. It boosts your job post to help it reach quality talent fast. Cut through the chaos with Indeed sponsored jobs. Get a $75 sponsored job credit at indeed.com/podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed sponsored jobs.

• 28:59Maggie Sellers Reum?

  You really do things early and against the 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?

• 29:10Speaker 02

  I think so. I mean,

• 29:13Speaker 02

  Things hurt, right? People have said a lot of things about me. They've said a lot of things about Girlboss and, you know, I'm gonna Girlboss my way to the sun or blah, blah, blah. And, you know, she's amazing. I post her child 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, I actually last minute ditched a podcast recently because I saw the brief moments before and I was like, I'm gonna choke.

• 29:58Speaker 02

  I can't fake my way through answers about, about this. And I would rather do that. I felt 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, the Netflix series or the book or Girlboss over the 12 years since it was published. Or, you know, and, and I, and I still feel it. And it can hurt. But just as many people are like stoked to chat with me.

• 30:43Maggie Sellers Reum?

  Yeah.

• 30:43Speaker 02

  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, wow, my Girlboss. But my DMs 12 years later are full of women being like, oh, my God, thank you, I read you. Women are 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 wearing probably pajamas and this person appears and she's like, oh, my God, it just, it's like,

• 31:27Speaker 02

  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, 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 you share your story and it makes them happy or 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.

• 32:09Speaker 02

  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. 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.

• 32:52Speaker 02

  And he saw 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?

• 33:36Speaker 02

  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.

• 33:49Maggie Sellers Reum?

  Do you agree with that saying, then, your net worth is your network?

• 33:53Speaker 02

  Kinda. Kinda, I hate saying, you know, it's like, but yeah, yeah. I never hang out with people because of their net, their net worth. I think 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.

• 34:36Speaker 02

  Um, 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-mm.

• 34:58Maggie Sellers Reum?

  You just posted a video saying, everyone tells you how to build your network, but no one talks about how you destroy it.

• 35:05Speaker 02

  Hmm.

• 35:06Maggie Sellers Reum?

  How does someone destroy their network?

• 35:09Speaker 02

  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, you know, my friend Frederique is actually a rocket scientist, but she invests, she invests out of Google Ventures and you should probably...

• 35:34Maggie Sellers Reum?

  Love her, Frederdeam.

• 35:34Speaker 02

  Yeah, yeah.

• 35:35Maggie Sellers Reum?

  We have co-invested in Alara together.

• 35:37Speaker 02

  Okay, cool. 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 can, you're trying to prove your, 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 wanna have a second phone call or isn't interested in what they're doing or doesn't wanna have a first phone call, honestly,

• 36:22Speaker 02

  then you're wasting that person's time. You're wasting the other person's time. You're getting their hopes up. And, you know, ultimately, it like erodes your reputation because the next time you try to make an introduction to that person, you should, you know, they're, they're, they're absolutely gonna say no. So it's your job to protect the interests of the people in your network who 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.

• 37:04Maggie Sellers Reum?

  I hate when people say, I wanna pick your brain. Like, about what, though? Like, I wanna protect my brain?

• 37:11Speaker 02

  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?

• 37:41Maggie Sellers Reum?

  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 this person's name, age, always. But with yours, it's actually like, what does Sofia and Maruso do now? And that was actually what I was like so excited.

• 38:07Speaker 02

  Cool.

• 38:07Maggie Sellers Reum?

  To talk about because I feel like, yes, you're known for nasty gal and Girlboss, 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 and the frameworks and like the companies. And so I wanna start the conversation with something that like just only Sofia and Maruso 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 and everybody wanting to get on cap tables when they're like famous?

• 38:46Speaker 02

  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 this 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 shill a product, right? And they're gonna have a much longer approach to how they can support that company.

• 39:29Speaker 02

  I mean, I think Stephen'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 can, 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 going to be too. So everybody wins. You're not just promoting a thing because some brand came to you with an RFP saying,

• 40:13Speaker 02

  "We want one reel, three stories, and we want you to repost it to TikTok with 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.

• 40:28Maggie Sellers Reum?

  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, Lovable. These are all who I would think of as winners in their category. A lot of people are going to start thinking about investing in 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?

• 41:03Speaker 02

  I mean, Lovable is like a rocket ship. I mean, Lovable is making it possible for anybody to build anything by chatting. And it's crazy because I still know people where I mentioned Lovable or even, you know, ChatGPT 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. Lovable is 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,

• 41:48Speaker 02

  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 a product description and list a vintage item and start a business. And so I'm very, very excited about where that's headed.

• 42:13Maggie Sellers Reum?

  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?

• 42:23Speaker 02

  I 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 it. 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 were like 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 statistic. 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.

• 43:07Speaker 02

  And actually, if you're not using it, I do think you're going to 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.

• 43:45Speaker 02

  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 Cat GPT, right? Like she's, she was on the podcast.

• 44:00Maggie Sellers Reum?

  That's why I was asking, because her, 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?

• 44:17Speaker 02

  That's not what I told you.

• 44:20Speaker 02

  Stop using M dashes. It's not this, it's that. Don't ever use that again. But I already told you that. What the fuck? Like, that's, those are the prompts I use the most. As, 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.

• 44:46Maggie Sellers Reum?

  How do you recommend women be smart about money?

• 44:51Speaker 02

  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 because 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. Like 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 what kind of income that you have, or maybe you feel more secure, you can figure out what to do with it.

• 45:35Speaker 02

  But the earlier you start saving, the better. And I would say, don't get carried away with Birkin bags. Like, that's, it'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 is worth the money. I generally just say that coffee is worth the money.

• 46:08Maggie Sellers Reum?

  10 years ago, you were named one of the richest self-made women in the world by Forbes.

• 46:13Speaker 02

  I know.

• 46:14Maggie Sellers Reum?

  That's crazy.

• 46:15Speaker 02

  It is crazy.

• 46:16Maggie Sellers Reum?

  Do you think that people treated you differently?

• 46:19Speaker 02

  No. I don't know. I mean, I employed most of the people that I was around, so probably.

• 46:28Maggie Sellers Reum?

  You know that rent and mortgage payments have got to be the least sexy thing we spend our money on, but they're a necessity. You have to pay them whether you like it or not. And with our sponsor, Bilt, you can earn points on rent and mortgage payments to put towards the nicer and finer things in life, like flights, hotels, that hot yoga class you've been putting off, and more. And I love that idea because it's kind of like your housing payment takes care of the responsible stuff and Bilt gives you a little something for the fun stuff. Bilt can make other parts of where you live more rewarding too. Just download the Bilt app, link a debit or a credit card, and ask the neighborhood concierge pretty much anything.

• 47:11Maggie Sellers Reum?

  It can tell you about exclusive benefits at restaurants, fitness studios, and more around your home. Download the Bilt app and join the membership for where you live at joinbilt.com slash HSR. That's J O I N B I L T dot com slash HSR. And make sure to use our URL so they know that we sent you. Hot take incoming. Making more money as a creator doesn't actually require you to have more followers. I see so many creators getting this wrong. And this is part of the reason why I love what our show partner Stan is doing with their V2 of their funnels and order bumps. Because if someone is already buying from you, that's a completely different moment than someone casually watching your content.

• 47:55Maggie Sellers Reum?

  It means that they trust you, they're paying attention, they're already in checkout mode. So instead of sending everyone to one link and hoping for the best, Stan helps you create a smarter buying journey. And with order bumps, someone can add something extra at checkout with one click. If you are building a creator business, this is the kind of thing you should be obsessed with, like every brand founder is. I'll let you in on one secret. The top earners on Stan all do this. 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/meggie.

• 48:33Speaker 01

  The action's on the court. And as the official beer sponsor of the NBA, Michelob Ultra is getting fans closer to the game with a chance to win courtside seats, merch, and more. Visit michelobultra.com/courtside to enter. Michelob Ultra Courtside, 26 to 27. No purchase necessary. Open to U.S. residents 21-plus. Begins on October 1st, 2026 and ends on June 30th, 2027. Multiple entry periods. See official rules at michelobultra.com/courtside for free entry, entry deadlines, prizes, and details.

• 49:01Speaker 03

  This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense. Indeed sponsored jobs can help carry the load. It boosts your job post to help it reach quality talent fast. Cut through the chaos with Indeed sponsored jobs. Get a $75 sponsored job credit at indeed.com/podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed sponsored jobs.

• 49:31Maggie Sellers Reum?

  You're 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.

• 49:43Speaker 02

  Okay.

• 49:44Maggie Sellers Reum?

  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?

• 49:58Speaker 02

  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, you know, maybe they've outsourced a little bit of

• 50:18Speaker 02

  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 like 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 like 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

• 51:03Speaker 02

  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 Gal. If their package came late or we sent them the wrong thing, it was like their friend 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

• 51:46Speaker 02

  of what the girl boss should be, whatever that was that people projected onto me, certainly, certainly put me in a place where, you know, I was ripe for criticism because when you stand for something or you're almost like a caricature of what, of a thing, which was like girl boss. And something happens that stands in contrast to it.

• 52:13Speaker 02

  People will hold it against you. And I think a lot of female founders experience it. I don't, 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, it's probably going to happen to you. What's the headline? Whatever. It'll sell something, right? Like I sold magazines when I was the 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?

• 52:58Speaker 02

  Like, am I the what? Just because I didn't pull it off or I wasn't perfect? Does that, that means that an entire generation, what? Right? So somebody's always making money somewhere by saying some kind of bullshit.

• 53:15Maggie Sellers Reum?

  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 like 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 in 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.

• 53:59Maggie Sellers Reum?

  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 10 years. Maybe it does, maybe it takes a bit longer. But there's so many different chapters that we're all going to have. And I think 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

• 54:44Maggie Sellers Reum?

  for the last few years, like, what are the frameworks that you would tell people of like, investing 101? What really gets you excited? And then what are the absolute red flags of things where you're like, immediately I will never invest money in your company?

• 54:59Speaker 02

  Uh huh. 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. 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. Once 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.

• 55:44Speaker 02

  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 that'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. With angel investing, it's just important to start small, right?

• 56:25Speaker 02

  And just because, I mean, some companies will say the smallest check we'll take is $10,000. If you can't afford $10,000, don't get all hyped up and dump 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, I'm like, it's fine. You don't, like, Nasty Gal happened 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.

• 57:06Speaker 02

  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, oh, 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. Maybe it's not, maybe it's better that they put their money somewhere else.

• 57:50Speaker 02

  If the existing investors aren't continuing to invest, that can be a red flag. And that happened to me at Nasty Gal. It made it really hard to fundraise.

• 57:57Maggie Sellers Reum?

  When you're investing in a founder, what are the three things that you absolutely look for that they have to have to invest money in them?

• 58:02Speaker 02

  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 customer is having or what that opportunity might be and have a clear vision of how they want to solve that. 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 like graduated. But in early-stage companies, you need to be using every resource that you have. And I invest because I'm a resource and it's really fun and I want to flex that.

• 58:47Speaker 02

  And I want to, because it's very gratifying for me to use my experience and see what connections I can make. So why 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. Like, I'm not going to be offended if you don't do what I suggested. I think that's like, it's crazy when people behave like that. But they have to be open. Like, so the first question was, they kind of have to be a visionary and hell-bent, 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,

• 59:33Speaker 02

  hear from people who might have more experience to help them see around corners. They 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.

• 59:48Maggie Sellers Reum?

  I agree. Okay, Sophia and Marissa, we have to ask you some rapid fire.

• 59:52Speaker 02

  Okay.

• 59:53Maggie Sellers Reum?

  What is the last thing you put on your credit card?

• 59:56Speaker 02

  Everything.

• 59:57Maggie Sellers Reum?

  What's the last thing?

• 59:58Speaker 02

  Coffee.

• 59:59Maggie Sellers Reum?

  Love life. What's your order?

• 1:00:02Speaker 02

  A cappuccino with whole milk.

• 1:00:04Maggie Sellers Reum?

  What's the last most expensive thing you put on your credit card?

• 1:00:07Speaker 02

  Maybe this ring, Snelly Kocolin ring, my friend's brand. It was expensive.

• 1:00:14Maggie Sellers Reum?

  Yeah, it's gorge.

• 1:00:15Speaker 02

  Yeah, thanks.

• 1:00:16Maggie Sellers Reum?

  What's the company you passed on investing in that you regret?

• 1:00:18Speaker 02

  It was Substack. So Andrew Chen from Andreessen introduced me to the founder. They were raising a round 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 something. It would have been an angel check, but I didn't. And I don't know if they've fundraised since, that's not the point, but they've, I know they're killing it, right? I know something's gonna happen there. So shame on me.

• 1:00:51Maggie Sellers Reum?

  What's the most amount of money you've ever put into one deal? Cause you just had a hundred K there.

• 1:00:54Speaker 02

  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 into a void. 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.

• 1:01:38Speaker 02

  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, wow, you scammed us for free equity. But like, that's what happened, that what can happen over 10 years.

• 1:02:10Maggie Sellers Reum?

  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.

• 1:02:33Speaker 02

  For sure.

• 1:02:34Maggie Sellers Reum?

  And like, I have here that Nasty Gal was once 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.

• 1:02:53Speaker 02

  And because I can pick winners.

• 1:02:55Maggie Sellers Reum?

  Yeah.

• 1:02:55Speaker 02

  And because I can make an impact on them too. But yes, I will forever be riding in the coattails 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 gonna disappoint 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.

• 1:03:41Speaker 02

  But when you have exhausted every avenue to make your investors whole on their money, grow revenue, you just, 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.

• 1:04:03Speaker 02

  It's okay to disappoint people.

• 1:04:05Maggie Sellers Reum?

  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?

• 1:04:11Speaker 02

  Never moving houses again.

• 1:04:14Maggie Sellers Reum?

  What fashion trend do you hope comes back?

• 1:04:18Speaker 02

  Like, are high-waisted pants out?

• 1:04:22Maggie Sellers Reum?

  Yeah, you can bring those back.

• 1:04:23Speaker 02

  I just, are they always out?

• 1:04:25Maggie Sellers Reum?

  No, you can bring them back.

• 1:04:26Speaker 02

  Here and there. But 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.

• 1:04:34Maggie Sellers Reum?

  Love. What's a luxury brand that's overrated?

• 1:04:38Speaker 02

  Honestly, the quality of Miu Miu bags, walking into their store. I was like pretty kind of disappointed, so I went to Balenciaga.

• 1:04:47Maggie Sellers Reum?

  Okay. Paris or London Fashion Week?

• 1:04:50Speaker 02

  London. I don't like Paris. I'm not a Paris fan.

• 1:04:56Maggie Sellers Reum?

  That's crazy.

• 1:04:57Speaker 02

  Yeah.

• 1:04:58Maggie Sellers Reum?

  What is a fashion trend you would end right now?

• 1:05:02Speaker 02

  The teenagers wearing giant sweatpants. Like, just like slobby 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.

• 1:05:17Maggie Sellers Reum?

  Okay.

• 1:05:18Speaker 02

  Yeah.

• 1:05:19Maggie Sellers Reum?

  Okay, if you were to title this season of your life, what would it be called?

• 1:05:22Speaker 02

  Lime Bike.

• 1:05:24Maggie Sellers Reum?

  Lime Bike.

• 1:05:25Speaker 02

  Lime Bikes and, um, what else do I do a lot? I don't know. Lime Bikes and Euro Summer.

• 1:05:35Maggie Sellers Reum?

  Love it. Okay, if you told yourself one HSR love note for the rest of your life, what would it be?

• 1:05:40Speaker 02

  You're always gonna land on your feet.

• 1:05:42Maggie Sellers Reum?

  Love that. Sophia and Maruso, thank you so much. Where can people find you and how can HSR help you?

• 1:05:49Speaker 02

  Sophia and Maruso, at everything, um, 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.

• 1:06:07Maggie Sellers Reum?

  Love it. Thank you so much.

• 1:06:09Speaker 02

  Thank you.

• 1:06:20Maggie Sellers Reum?

  If you're starting a business, there are certain things that are so fun to think about. Y'all know I love a mood board, so everything that relates to the creative, the name, the brand, the website, the vision board. But then there are the things that make you pause and ask, am I even doing this correctly? Or do I even want to be doing this? Like forming your business, getting the right documents, keeping your personal information private. This is where our sponsor, Northwest Registered Agent, is so helpful. They're a one-stop shop for founders who want to launch and legitimize their business without turning it into a giant admin spiral. They help you form an LLC or a corporation, act as your registered agent, and give you tools like a business address, operating agreement, website, phone number, professional email, and free guides.

• 1:07:03Maggie Sellers Reum?

  They also have real corporate guides who know your local laws. Visit northwestregisteredagent.com/hsrfree and start using free resources to build something amazing. Get more with Northwest Registered Agent at northwestregisteredagent.com/hsrfree.

• 1:07:24Speaker 04

  When fall comes back around, there's a sense of a reset. And new pieces from Lululemon's fall drop are an inspiration to push your goals and elevate your routines. As your calendar fills, easy-to-layer styles meet the demands of your day. And as you challenge yourself to try even more, versatile sets transition with you. The Lululemon fall lineup brings new levels of comfort and confidence, whether you're starting something fresh or starting something over. Check out the latest arrivals in store and on lululemon.com now.