#72 with Sophia Amoruso - GIRLBOSS

Today we hang out with Sophia Amoruso (@sophiaamoruso), founder of Nasty Gal & Girlboss. Her story is bananas. She is a community college dropout who created a company that at its peak was valued over $400M+. She has had highs (sold over 500k copies of her book) & lows (nasty gal eventually crumbled) and we talk about both. I was pretty blown away by her honesty. She wasn't trying to make herself sound good or look good (which ironically, made her sound/look great to me). We start with some fun topics like The Bachelor & her favorite cars she's owned (2:23), About her background and businesses (4:45), The story of Nasty Gal: $30m revenue, Index putting $50M investment and her selling life changing secondary (6:44), Expectations after raising venture capital (11:31), Starting conference businesses (15:54), Being a starter vs. operator (17:16), Downsides of being the CEO (20:52), How she got her book to sell 500K copies (24:54), Her investment portfolio of startups and funds (29:17), What's in store for her in the next 10 years? (32:45), Freemium vs Subscription for content (37:13), Opportunities and trends she's seen in the media + retail space (40:06) and Sam's great book recommendation with a horrible - How to Get Rich by Felix Dennis (43:27) Today's ep is possible because of Superside! Head to www.superside.com to hire a dedicated team of designers for your project! See acast.com/privacy for privacy and opt-out information.

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

• 0:00Sam Parr?

  This episode is brought to you by Superside. So superside.com. If you need something designed quickly, go to superside.com, give them a try.

• 0:07Speaker 01

  That was it. Like, I didn't have savings. And I went from upgrading from my 87 Volvo to a year and a half later, fucking Panamera, and was like, what is this? I can like buy everyone oysters?

• 0:21Shaan Puri?

  What's up? I'm here. Sam's here. And we got special guest, Sophia Amoroso. We're just explaining what this podcast is. And I think we're, we're kind of shit at explaining it because most people, when they come on a podcast, they're like, okay, cool. These people are going to interview me. And we kind of do. We do ask questions because we're curious. But for the most part, the feel of it is, what if the three of us were sort of at dinner and we were just shooting the shit on stuff that's interesting to us and let the conversation go where it may? And that's, that's really the, the overall vibe of the podcast. And so, um, so we can start with whatever. Sam's read your book. I've read your Twitter. Um, I have a question off your Twitter. That's just a fun little icebreaker. I saw that you tweeted a very controversial tweet, actually not so controversial, because many people would agree.

• 1:06Shaan Puri?

  You said that Peter is a national disgrace. You watch The Bachelor?

• 1:10Speaker 01

  Oh, yeah, yeah.

• 1:12Shaan Puri?

  Give me 30 seconds. Why is Peter a national disgrace?

• 1:15Speaker 01

  Man, my boyfriend was saying last night, he was like, it's okay. Like, you're into The Bachelor. And I was like, I'm not into The Bachelor. He's like, you watch it every season. That means you're into it. And I'm like, that is not part of my identity. I am not into The Bachelor. And, um, I guess what you do is who you are, right? What is that? Like, Ben Horowitz's new book or something? Um, uh, he's like a doof. He just like, he's just like the most generic. I just don't know how you find people that generic. Um, yeah, there's just like no deviance whatsoever. And that just like creeps me out. Like,

• 1:48Sam Parr?

  I think the word is basic.

• 1:50Speaker 01

  Yeah, basic.

• 1:51Shaan Puri?

  I think what people-

• 1:52Sam Parr?

  I think that's the B word.

• 1:53Speaker 01

  Like, entry level human.

• 1:55Shaan Puri?

  This guy's, yeah, he's pretty, he's pretty universally disliked, uh, as The Bachelor. Nobody dislikes him because he's not controversial. He doesn't do anything that necessarily that bad. He doesn't also do anything, period. He's sort of a non-decision maker, which is-

• 2:07Speaker 01

  Yeah, he just like flip flops and hurts people. Why would you want to date that guy?

• 2:12Shaan Puri?

  Not great. Okay, so that's your thoughts on The Bachelor. Um, Sam, you read the book, so I think you you have maybe some uh some more interesting questions than than I do.

• 2:19Sam Parr?

  Well, I just had just I'm gonna dive deep into all this, but but the first quick question is what type of Porsche do you have?

• 2:26Speaker 01

  I don't. That's like that's like many cars ago.

• 2:29Sam Parr?

  What do you have now?

• 2:30Speaker 01

  I I did the Porsche and then I did uh I had like the Jaguar F-Type like right when it came out again, which is just like, why am I driving a sports car? Like, I like cars.

• 2:42Sam Parr?

  Well, and and F-Type is like a supercar, right? Or is that the SUV?

• 2:46Speaker 01

  No, it's yeah, it's like a it's like a racy race car.

• 2:49Sam Parr?

  Right, like the wing, it's like the the doors go up.

• 2:52Speaker 01

  Uh, I don't think they go up, but I do have the Model X now and the doors do go up. But um, so I had the F-Type and then I had a Range Rover for like five years. I wrote Girlboss like seven years ago, so I've been through many cars and now uh I drive the Model X and I like it a lot.

• 3:09Sam Parr?

  What type of Porsche was it?

• 3:09Speaker 01

  It's a Panamera.

• 3:11Sam Parr?

  Worth it or not? I hear mixed feelings on that.

• 3:13Speaker 01

  Huge car. I mean, honestly, anything other than a Tesla feels like driving like an ancient.

• 3:19Shaan Puri?

  In the past.

• 3:20Speaker 01

  Like, why would you pay to like hassle with CarPlay or whatever it's called? I I don't know.

• 3:27Shaan Puri?

  I was about to buy the Model X uh a few months ago, but then I got spooked because I'm on Twitter all the time and I ended up in this rabbit hole on Twitter of the people who believe that Tesla is like a giant fraud. Uh, like, great product, but the company is sort of uh in dire straits financially. And it's pretty convincing if you end up going down there, like most conspiracies, if if you sort of go down that road, you'll end up believing, you know, some between thirty and eighty percent of it. And so I got spooked by the end. I was like, okay, I I don't want to buy this car if this company's not going to survive uh long term. So that was that was my takeaway. What do you think of that?

• 4:01Speaker 01

  Um, I mean, I own Tesla stock and I'm really enjoying the volatility and I'm like in it for the long haul. I, you know, in terms of Tesla being fraudulent, it's like, what company isn't at some point? It's like. Fake it till you make it. I mean, he really, he's like very much a liability, but I mean, it's just a great product. So also, the Model X is over 6,000 pounds, which qualifies as a commercial vehicle, which means you can write it off.

• 4:31Shaan Puri?

  Yeah, that's what I ended up doing. I ended up just buying a really big, heavy BMW to write it off.

• 4:36Speaker 01

  Yeah.

• 4:36Sam Parr?

  I didn't, I didn't know about this. So Sophia, to the listeners, you, I'm gonna give your, I'm gonna tell you folks what I know about you, and which is that you started as, it was Nasty Gal. Originally, it was a vintage clothes shop, which I dig. I used to work for that TV show called American Pickers, and we would buy, buy and sell a ton of old leather jackets and things like that. So that's one of the reasons why I was interested in you early on, years ago. And then you scaled that to just nastygal.com, I mean, just like a proper menu, clothing brand. It got quite huge, and then it went down as, it went down as fast as it went up. I mean, it was a roller coaster of a ride, right?

• 5:15Speaker 01

  It went down a lot faster than it.

• 5:19Sam Parr?

  It was a roller coaster. And then you went and launched Girlboss, which was a, well, it's a whole brand of books and TV shows, but a social networking site. And you sold that to Nick Bell at Attention Capital, right?

• 5:31Speaker 01

  Yeah. So Joe Marquez, Nick Bell, I don't, Nick Bell's not even super involved anymore, so that's interesting. Sold the company at the end of last year to, you know, Joe's like been a friend of mine for like five or six years, just someone like I really love, who's been one of Girlboss's and my biggest supporters, like put money into Girlboss before I even had a deck, you know, just months after Nasty Gal fell apart. But yeah, that's the gist of the story. It's a real long story. And when I wrote Girlboss in 2014, that was, you know, that was, I wrote that when I was like at my peak, and I was like naive and like on a high. And I'd experienced adversity, but like a warehouse melting down

• 6:14Speaker 01

  and customers being angry, but not to the extent that, you know, it was coming for me. And so I'm writing a book right now that's, you know, it's not gonna be out until 2021. I think I'm calling it tough shit and it's everything that happened after Girlboss. So like the two years before Nasty Gal face planted and everything like a divorce, like everything that could have gone wrong went wrong. It's pretty entertaining.

• 6:44Sam Parr?

  How big was Nasty Gal at its peak?

• 6:46Speaker 01

  Yeah, so we did over a hundred million in revenue and the company was worth like three hundred and fifty million dollars. So Index put fifty million in. I bootstrapped it to twenty eight million profitably. And then venture investors were like, who is this freak? Because the only thing I understood was you buy something for a dollar and you sell it for two dollars and then you invest like a dollar twenty five and like don't spend more money than you have. Like how else are you gonna have a business if it doesn't like produce money? I just didn't, you know, I'm a community college dropout, so it's like buy something for more, sell something for more than you buy it for, and then don't spend all your money. Like it's pretty basic.

• 7:24Sam Parr?

  At twenty eight, well, and at twenty eight million in sales bootstrapped, what were, what was the income off? What's, what's an income off twenty eight million for that type of business?

• 7:33Speaker 01

  What was the profit? I don't even remember, honestly. I was just like, at that point I had saved over a million dollars in just cash in the bank. Like I have a screenshot of like the basic Bank of America, like bank account where, and I, and also under it is my personal account. I have something like eight grand. Like I didn't really pay myself. I didn't even want that.

• 7:53Sam Parr?

  Well, the business had a million and you, you were all in.

• 7:57Speaker 01

  I just like, I mean, I was all in in that like I, there wasn't like equity. I just like was a small business owner of a business that got big. It was like a mom and pop shop that got big. So to me, it wasn't like, oh, high risk. I don't have, you know, a lot of stock. There was no stock. And so I owned a hundred percent of the company until Index came in in twenty twelve and invested fifty million on a three fifty post. And after that, I owned eighty percent of the business. So that's great.

• 8:25Shaan Puri?

  Where'd Index come from? So were you out like, hey, I need to go raise money? Or did somebody say, hey, this thing is taking off. Let's go talk to her about venture capital?

• 8:32Speaker 01

  Yeah, venture started like sniffing me out like they started coming to me and I was like, you know, I had an advisor who was like, just build it as big as you can because then you'll sell less for more. And also, simple math, right? Um, so I, you know, I didn't, we didn't need the capital, but I was like, whoa, if someone gives my company that much money and all I have to give up is like, and I still control the whole thing and I have two.

• 8:57Shaan Puri?

  How those numbers came about? How did the number, because I I've done this before when you raise money and you know, sometimes you go in looking for two and they're like, how about seven? And what, okay, seven million, that sounds good. What was the valuation? And then they throw out a big number.

• 9:08Speaker 01

  Totally, yeah. I mean, they want to own their 20%, right? Um, and it was a growth. It was the first money one was out of a brand new growth fund.

• 9:16Shaan Puri?

  Right.

• 9:17Speaker 01

  It was like the second investment out of that after like their big investment in Dropbox at the time. So I think growth rounds are, you know, people aren't looking to, you know, place small bets. They want to own, they want to own a significant amount of money and then or the business. And I I didn't like game it, like I didn't, I was just like, whoa, that's crazy. You think it's worth $350 million and we're making like 30 million in revenue? Whatever. I didn't like, you know, have more than one term sheet. I never, I mean, I think I might have like bartered the way you'd barter at like, you know, a like a, like an estate sale. And I was like, no, this much for this much. And that was like, that was it.

• 9:52Shaan Puri?

  Right.

• 9:53Speaker 01

  Um, it took some money off the table. That was totally life changing.

• 9:57Shaan Puri?

  Can you say how much?

• 9:58Speaker 01

  Nah, no.

• 10:00Shaan Puri?

  How'd you decide to do that? Because me and Sam have both been through this where we're trying to decide how much and, you know, investors are are cool with it if you have momentum, but they're also like, look, we're not, we don't want you sort of sleeping in silk sheets every night either. So how did you decide the amount?

• 10:15Shaan Puri?

  You just picked a number?

• 10:16Speaker 01

  Um, yeah, because the company didn't need, need money. They were just like, I didn't know what secondary was. And they were like, yeah, like, well, you know, the company doesn't need 50 million. So here we'll put the majority of it.

• 10:28Shaan Puri?

  Right.

• 10:29Speaker 01

  Into the business, but you know. More than half into the business, but a lot into my bank account because it was just, it was still, it's just the same stock, like they have the same position regardless. And, you know, at the growth, you know, stage, especially when the entrepreneurs, you know, still owns a significant amount of the company, like you're incentivized, even if you do take a lot of money off the table, if you're not deluded to the point where you own like 10% of the company and like, you know, have like fuck you money, then like that's a different position. But for me to have that big of a stake in, in Nasty Gal and, and yeah, like be able to like not worry about, you know, their whole thing is like, we don't want you to like worry about money, which at the time was like, I had a paycheck, but like that

• 11:13Speaker 01

  was it. Like I didn't have savings. Um, and I went from, you know, driving like, you know, upgrading from my eighty seven Volvo to a Nissan Murano to like, you know, a year and a half later, fucking Panamera and was like, what is this? I can like buy everyone oysters?

• 11:30Sam Parr?

  Would the, would the company have thrived had it not taken any money?

• 11:36Speaker 01

  I don't know.

• 11:38Sam Parr?

  What do you think?

• 11:39Speaker 01

  I think the expectations would have been, there weren't expectations. It was just like, great. Like we won't spend more money than we have. And I never would have, honestly, like I wouldn't have known how to control like a company's finances, but I did have great people who were the kind of people that had built profitable businesses. They weren't the operators that come in from venture backed businesses and, you know, understand, you know, wild expectations that, you know, when it was a bootstrap business, we just didn't have it all. Um, yeah, I think so. Like I think I probably would have sold the company for like a fair amount of money. Um, I mean, at one point there was an urban clothing retailer that offered over four hundred and it was like four hundred and twelve million dollars on, um, like a piece of paper.

• 12:24Speaker 01

  When I owned eighty percent of the business and my investor told me to ask for more and then it went away.

• 12:31Sam Parr?

  Fuck. How, uh, that's.

• 12:34Shaan Puri?

  Well, hold on, hold on. We can't change topics. That's amazing. Uh, what was that like?

• 12:38Speaker 01

  Like, whatever. You know, they were convinced that they were like, no, this is gonna be a billion dollar business. I mean, to them, it's just like a drop in the bucket. It's not like, you know, if it doesn't work out, I mean, it's just like, but go big or go home, you know?

• 12:50Shaan Puri?

  If they invest at three fifty and it returns at four hundred, that's not a win. That's an opportunity lost. Uh, they could have been betting on something else.

• 12:58Speaker 01

  Yeah, they're like, why bother? And from that point on, when we did need to raise capital after that, or tried to raise capital after that, or other people, like largely when other people came in and were like, hey, we want to invest at this valuation, that was still like a healthy retail valuation. I was cock blocked. Like, they didn't have control, but there would be side conversations, you know, after like I teed someone up and they were totally bought in. They'd be like, great, I'd love to talk to your board member. And I love this guy. Always love this guy. And after like, like a few, like they just like kind of disappear for some reason. And I didn't really connect the dots. And at a certain point, you know, at six months later, I'd reach out to that person and be like, whoa,

• 13:41Speaker 01

  you like totally ghosted what happened. And they're like, yeah, your, your investor told me to like not even show up unless I paid this much. And that just happened like behind the scenes over the course of like, just like starved us out for a long time. Um, when we could have had, you know, much better terms, two years, a year and a half before Nasty Gal fell apart. I just, you know, that was stuff that I wasn't, I didn't know was happening.

• 14:06Sam Parr?

  So why did you raise money again then for Girlboss? Why?

• 14:09Speaker 01

  I don't know. Honestly, I don't think so. No. Cause like, I like wanted to do a conference and it wasn't prop, the, the conference was initially profitable. Um, but it wasn't like profitable enough to build a business because I had seen what enterprise value can do. And like, I could enter paycheck for the rest of my life, or I could go like build another business that's worth more than the revenue that's coming in. And Girlboss is a really powerful brand. It's an amazing opportunity. There was like so much groundswell behind the brand. Cause you know, I said, I founded it in twenty seventeen. That was. Whatever, fourteen, three years after, you know, the book was a bestseller, the hashtags been used twenty million times on Instagram. And then I started the business because I knew there was like this.

• 14:51Speaker 01

  I had our first conference a month before the Netflix series came out, which was gonna put the name Girlboss into a hundred and fifty million homes in a hundred and ninety-five countries. So I was like, oh shit, like I better build the mitt that like catches all that awareness. Because like I can capitalize on that. And I did, but not to the point of like, you know, I didn't sell a company for like a bazillion dollars.

• 15:17Sam Parr?

  So my, my company, The Hustle, you know, I don't, I don't, I have no idea if you know this or not, it doesn't matter, but we started as a conference. So I started it.

• 15:24Shaan Puri?

  Did you read Sam's book?

• 15:25Sam Parr?

  Yeah, have you read, have you, have you Googled it? No.

• 15:28Speaker 01

  I don't remember the last, I need to read books. It's like a thing.

• 15:31Sam Parr?

  That's right. So we started it as HustleCon and so we get up until the stupid stuff going on now, tens of thousands of attendees. And I use like the, about the first half a million that we made off the first event or two as our seed money. So I hear you in conferences, it gives you a little high too. They're quite challenging to scale to be very large, but it is possible. Did you like the conference business?

• 15:56Speaker 01

  As a business, no, but as like an event, yeah. Like it's really fun. It's really fun to see these women from our community coming out and meeting one another. Women from thirty countries flew out for the last one in like forty-one states or something. It's just the awareness of Girlboss is super distributed because the book was in every airport and bookstore in the country. So it didn't like start in the cities or, you know, it's still largely in LA and New York, but very like broad, broad like awareness. And so to see just like all these awesome women descend on Los Angeles and New York and get so much out of it is a great feeling.

• 16:37Speaker 01

  I'm not an extrovert, so getting on stage is like, I don't love it, but it's like part of my job. So there was that part, but I loved everything else about it.

• 16:47Sam Parr?

  You, you and I are from, you know, I feel like I know you. And even though you have no idea who I am, because I've listened to your podcast and read your book. So I feel as though we're a little bit similar and Sean as well in that it seems like you're very creative. You're pretty, you're a pretty good business person, but you're more so creative than anything. And do you, what, what was, what's your whole take on operating the company and like running it versus starting it? And working on like weird projects like, were you running? I don't think you're running Nasty Gal later on, were you?

• 17:20Speaker 01

  I didn't for the last like couple of years. I, I like opted out. I was like, I don't want to be, I just don't want to be a CEO. I'm not creative anymore. I'm stuck in meetings all day. I'm not a great operator. I'm like the worst operator, like I've done stuff with my executive coach. And at the top is like entrepreneurial creativity, like autonomy. And all of those things are important to me. The bottom is general management, like at the bottom. So I've had to be an operator and by the sheer nature of having founded companies. I'm not very good at it. I'm, I've gotten a lot better at building culture. I don't think I'm a great business person, honestly. Like I think I can build excellent brands and I can drive revenue.

• 18:03Speaker 01

  I think I'm an excellent business person when it's like very hand to mouth. I don't think I am when there's just like, I don't know, just with venture, just expectations. And it's just floating in the ether. Like you know, your business model works when you start a company and makes money and pays for itself. Like that's still, I think what I'm still like a small business person that happened to build like big businesses. But more than all, I'm probably like a voice and a brand, you know, creative and a marketer.

• 18:33Sam Parr?

  Do you think that that, a lot of people don't, don't do that as much, or at least people in the, like the Silicon Valley pop culture type of realm. They think that hiring a CEO is actually silly because you see folks like the, the, the famous entrepreneurs are still the CEOs. In some cases, I don't know if that's actually the reality. Like they have strong operators like uh uh I think it's more common than people realize. But the whole idea of hiring a CEO or hiring someone to run the company is still a little bit frowned upon. I've done it. You did it. Do you think that that was a good move? And do you tell people to do that?

• 19:10Speaker 01

  I don't feel like it was frowned upon. I mean, the headlines were like that I stepped down, but I like stepped up into like a broader role is how I felt.

• 19:18Sam Parr?

  But that's what I'm saying. That is frowned upon. Like, like what I don't say, I'm not saying it's actually frowned upon, but a lot of people view it as something that you shouldn't do.

• 19:26Shaan Puri?

  As a negative event when it happens.

• 19:29Sam Parr?

  Yes.

• 19:30Speaker 01

  I mean, whatever. I mean, yeah, I thought about how it would be perceived and it was.

• 19:34Sam Parr?

  No, I don't give a fuck how it's perceived. I'm saying a lot of people inaccurately like they they think you shouldn't do that. And when I'm, in my opinion, I think a lot of people should. And what I'm asking is, do you think that other people should as well?

• 19:45Speaker 01

  Totally. I mean, I think it's individual. I think pretty much every entrepreneur who's raised venture capital like had a head start. Like I had never worked in an office or had a manager. Like my last job was in the lobby of an art school. So um I was probably never qualified to be a CEO and you're a CEO by the sheer nature of being a founder. But being a founder and a CEO, you inherit that title. To me, like, I don't care about titles. Like, I don't, I tried to name everyone in the company a co-founder, but they just like didn't catch on. Like, I was like, cool, you're all co-founders. Put that on your LinkedIn. Like, I don't care. Cause I just never, it was like never a goal of mine, right?

• 20:24Speaker 01

  So like, I don't, I didn't, I don't, I feel like in terms of like what I remember and how that was received and whether it was frowned upon or not, I've had so many other things that were frowned upon that were much more noisy than that, that it just, I think it's fallen into the background because I've been like frowned upon like plenty of times, much more loud, in a much more loud way than having stepped down, like for much bigger reasons or noisier.

• 20:52Shaan Puri?

  What's an example of those frowned upon moments?

• 20:54Speaker 01

  I mean, getting sued, going bankrupt, like laying people off, toxic culture. I mean, like a Netflix show being like canned, TMZ covering my divorce, like, I don't know, just some stuff.

• 21:07Shaan Puri?

  And the the skin is thick now or or has been?

• 21:09Speaker 01

  Pretty thick, pretty thick, yeah.

• 21:11Shaan Puri?

  Was it, was it always that way?

• 21:13Speaker 01

  No, I don't think so. I mean, it was until, you know, and I'm writing about this in the book. It's just like when people don't know you and they have, they judge you. It's just kind of like they're totally unqualified, but uh, and people, you know, it's great on a conference stage to say like, I don't care what other people think. And it's like great on Instagram to be like, I don't care what other people think. Once you don't care about what people think, it's like, how do you learn? And even if it's like totally wrong and coming from something, someone who's totally uninformed. Like I, I, I do have thick skin, but at the same time, I have to first assume that everything is true. And then weed out the things that aren't true. Cause if I don't consider that things that are said about me are true,

• 21:56Speaker 01

  like it's not an opportunity to learn. So as painful as that is, and as wrong as so much of it is, like I do think that caring about not what other people think, but what I guess like what you're, how, how other people feel as, you know, can't argue with people's feelings, right?

• 22:12Sam Parr?

  What, and you, you're kind of like, uh, I mean, you're kind of famous, like you, this TV show is quite popular. You have a book all over the place. It seems like you've got a pretty big personal audience on a, a variety of social channels. But you said you're introverted and you didn't start this shit to become famous. You started it because it was a cool, it was just like a, a cool hobby that made money and it spiraled into something, you know, bigger. What, uh, why do you think like they're writing about you on TMZ and shit like that? I mean, that's like mainstream stuff.

• 22:44Speaker 01

  Um, well, I think with TMZ, it was like, the Amherst would call it to quit, so the girl boss pays X of pigeons. I had a great prenup. Um, and yeah.

• 22:57Sam Parr?

  Cause that's weird, right?

• 22:58Speaker 01

  What?

• 23:00Speaker 01

  Mainstream. My story, um, is a rare one, which has made things a lot more difficult for me. But at the same time, um, you know, I'm, I'm a community college dropout from Sacramento. Um, every other business book or anyone, any other story, even of women, for the most part that you hear, they have like a, a leg up in some way. Not to say that, you know, I, I've. You know, plenty of privilege that I started out with, but you know, education and even working in office or having a manager was not one of them. Like I started a business with the tools that most, pretty much everybody has, which is like a digital camera and a laptop and access to estate sales and thrift stores, right? Like, you know, there was no like, I

• 23:42Speaker 01

  didn't know what supply chain was, or like, we weren't, I was manufacturing things. I just had access to stuff that everyone has access to. And I had probably less of an education than most of the people who wrote the book. So I think it inspired the rest of the, you know, world or the rest of women who, you know, may be accidental entrepreneurs or have side hustles, who didn't feel qualified. And that someone who was totally unqualified on paper was able to pull off what I did, I think gave like, in some ways, I don't want to be like, I give a generation hope, but in some ways, I think my story has.

• 24:20Sam Parr?

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• 24:54Shaan Puri?

  Tell us a little bit about the book. So, books are a funny thing, right? You, you know, getting one made is this like weird process. And then, you know, the point from where you have a story to it's sitting in every airport on the, you know, on the display stand as like, buy this thing. There's a lot that goes into that, some of which you control, some of which other people control, some of which is just luck. So how did your book get so popular? Was that something that, do you feel was like, like the easy answer is, I don't know, people just liked it. Word of mouth, it just spread. And then there's another side of the business where the right publisher with the right kind of footing can get you, can kind of engineer a lot of the, the growth. So how does a book get so popular? How did your book get so popular?

• 25:35Speaker 01

  Um, I mean, I tried to drive as many pre-orders as possible and now see how the two million person email list at the time. And for me, this was an opportunity to market our story was content marketing. I got someone to pay for us to put the logo of my company on the cover of a book. Like that felt like a marketing coup, like all of these things felt like marketing coups, not like opportunities to market myself. Or for me to have a personal brand. And instead of the book selling clothes, the book sold books. And like my story, um, which isn't like, oh, whoa, I'd never knew that putting myself on the cover of a book would like whatever. But I also had no idea, you know, it would go on to sell half a million copies and be published in like a bazillion languages.

• 26:18Speaker 01

  And spent 20 weeks on the New York Times bestseller list. I do know that, you know, Girlboss had an impact on the initial pop to get us on the list. But you don't stay on the list that long if your book, you know, if your book doesn't have merit.

• 26:30Sam Parr?

  Is is 500 million, or sorry, 500,000, uh, 500 million would be great, but 500,000 book sales. Is that a meaningful revenue driver for you or?

• 26:40Speaker 01

  Uh, that was good money, like the, the royalties like trickle in now, but for those first few years, that was like meaningful for me, which I did not expect. Like I earned out my advance like by multiples, you know?

• 26:52Sam Parr?

  What's a typical advance for that, like half a million dollars or something?

• 26:55Speaker 01

  Oh, God, no.

• 26:57Sam Parr?

  More or less, I have no idea.

• 26:58Speaker 01

  Less, like, I mean, I was just like an unproven author with a story that like a lot of editors, you know, even women came to the room, read my, um, my proposal, whatever you call it, and were like, you think this is too niche? We don't think like that many women like want to start businesses. They want to buy clothes or like, I don't know what they were, but like I got turned down by, you know, a handful of publishers. And then Carrie Colan, who was at Penguin at the time, she's at Audible now, um, was like, yeah, I get it. Awesome. And she was kinda, I mean, she, she made the book better, but she wasn't, she didn't try to make the book what she thought she wanted to, to be. She just let me run and write a book. Um, and that's when I do my best. I cannot be told what to do because I don't do a good job. Um.

• 27:44Speaker 01

  And uh yeah, there was an advance, but I think I don't remember. It was like maybe one fifty like I don't know. I don't remember, but like.

• 27:52Shaan Puri?

  Did you do a good job in your opinion now of negotiating the book deal because publishers have a lot of leverage? It's almost like venture capital, but even worse like it's.

• 28:01Speaker 01

  Yeah, I still I still don't think that I've done a good job with my existing book deal and I am working on the next one. The thing about advances is that like you can get a big advance, but if you don't earn out your advance, no one's going to publish your next book like everybody sees the performance of your book. So you either earn back your advance. You know, on top of your, you know, if you make five hundred K like you make that two fifty on top of a two fifty K, you know, let's say like. I don't know. I'm bad at math, but um basically if you sell five hundred K

• 28:34Speaker 01

  five hundred thousand dollars worth of books, like, you know, you're break even if you sell two hundred and fifty thousand dollars of books like if you try to do another book deal, you'll be held accountable to that. So it kind of doesn't really matter. You'll say make the same amount of money and actually be incentivized to out earn your advance if it's not that big because it's easy to be like, cool, I made money. Great. All right. But, you know.

• 28:54Sam Parr?

  Have you? So um uh Tim Ferriss was one of our angel investors and we're not I'm not terribly close with him, but I shoot the shit with him every once in a while and he has said something like his book was a great like revenue wise at the time, but he goes, my podcast is significantly bigger in terms of revenue. And my angel investing has been way bigger beyond that. Um have you ventured into that world of of startup and investing in the early stage companies?

• 29:23Speaker 01

  Yeah. So back when I got that like big windfall of money, I um I worked with iconic like Mike Anders and those guys like awesome like money. I don't know. They've worked only worked with like people who they think. Who's at least net worth on paper is like outrageous and mine was like two hundred and eighty thousand million, whatever.

• 29:45Sam Parr?

  Is iconic Mark Zuckerberg's thing or is like?

• 29:48Speaker 01

  Yeah, I think that's he's part of it, but it's not his. He's but they.

• 29:51Sam Parr?

  Got it.

• 29:51Speaker 01

  At some point they manage his money. I don't know who they work with now. And and I was invited to invest in their fund. So I'm an LP in their fund. I put like five hundred K in. I put like one fifty K into indexes fund. This was all back in like twenty thirteen, maybe. I put like a hundred and fifty K into first dibs back then. I was invited to invest in Blue Bottle at the time and. It's like I didn't drink coffee yet, so I was like, I can't invest in things I don't understand. I like furniture. And so a bad idea, but Brian Meehan, the CEO is like a great friend, invested in my businesses.

• 30:33Speaker 01

  And then I've done some angel investing, so I just invested in public dot com.

• 30:38Sam Parr?

  Yeah, I just signed up for it last night.

• 30:39Speaker 01

  Yeah, so.

• 30:40Sam Parr?

  Are you on there? I'll follow you. I'll I'll look.

• 30:42Speaker 01

  I am, yeah.

• 30:43Sam Parr?

  Your stocks.

• 30:44Speaker 01

  So I'm an advisor and and an investor. So if I get advisor shares, then it gets me up to a point where I have a significant. Stake in the business, at least for an angel investor. So I feel good about that. I invested in something called Blue Land. That's um. Sustainable, yeah, cleaning products where instead of using single use plastics where. You're buying like Windex and eighty ninety percent of what's in that bottle is water and you throw the plastic away. They send you these really beautiful reusable bottles. And you fill it with water and you drop a tablet into it. The only thing you buy over and over again is the tablet. So the founder Sarah Paigiu is super impressive. What else?

• 31:29Speaker 01

  I invested in Passport, which is like an international logistics company. They just raised a series A. I'm an advisor there. Invest in something called Chill House. Oh, I invested in Liquid Death and drinking it.

• 31:44Sam Parr?

  What has been the most lucrative angel investment you've made?

• 31:48Speaker 01

  I mean, none of them have returned anything yet, but I think First dibs is probably like, you know, they've gone on to raise several rounds. The iconic investment has, you know, they, I don't know, there's like Blackline and Alibaba and like a bunch of stuff I invested in back in like 2012, 2013. And that stuff like got dumped into fidelity or however it works. And I just pulled all of that out. I made enough money on it to be like, all right, I'm gonna like potatoes, capital gains, put that shit in the bank. It's just cash like for now. And then I still have like, I have a lot in my house, which is stupid. I'm overexposed in real estate, but I live here. It's awesome. And, um, and then I have

• 32:28Shaan Puri?

  Are you in LA?

• 32:29Speaker 01

  I have a bunch in like Morgan Stanley now. Um, who manages that stuff. Um, I'm in LA, I'm up in the hills. It's really pretty.

• 32:37Shaan Puri?

  Nice. And, you know, you've done a whole bunch of stuff and I feel like your, your story's cool because you're like, okay, I didn't sort of expect to go down this path, but probably every few years you look around and you're, you've hiked up this mountain and you're like, wow, okay, I see a whole bunch of other possibilities now.

• 32:51Speaker 01

  Yeah.

• 32:51Shaan Puri?

  What's like, I don't know, not like a 10 year plan, but like, what do you see yourself doing going forward? Like, are you gonna start more businesses? Do you, what do you want to do?

• 32:58Speaker 01

  It's such an interesting question because I, in some ways, like what I've done wasn't a choice because I'm a person who's like, oh my God, opportunity. Like Girlboss is the only thing I can do after Nasty Gal. It's like the opportunity to redeem myself. If I do a good job, I can build a happy culture. I can build and sell a business and exit and like, kind of like heal my, all my scars from Nasty Gal by, you know, building something that, you know, feels better. But I didn't, you know, I, things, I put things into the world that just like have momentum and then that's my life. Um, been 14 years since I founded Nasty Gal. I did that for a decade. Um, and this quarantine thing has had me being like, wow, like this is really different.

• 33:42Speaker 01

  I, I like working from home. I've done my best work solo. So I started an eBay store by myself and then it became this big thing. I um, you know, I wrote a book alone and it became this like big thing. And then I'm like, I have to catch all the, I mean, of course we should, we should all be, and I am so grateful that any thing I put out into the world, not anything, but like the things, some of the things I put out into the world just catch fire in that way. Um, but that leads me to in some ways, just being like beholden to the opportunity, which is like, oh, boo hoo, right? It's like, oh, I like to just raise money again and, you know, build a business. But at the same time, my lifestyle is not something I've ever thought about until recently.

• 34:25Speaker 01

  So when you're an entrepreneur, you don't work for yourself, you work for your business. And that comes, you know, just like, what you do is like what the business demands. Um, and I'm feeling like, you know, in the future, I want to have more choices. Like I, you know, I, I, I at some point want to just work on a smaller, I, I don't want to start a company ever again. So there's that. Um.

• 34:50Sam Parr?

  Wait, wait, wait. You don't want to start a business again?

• 34:52Speaker 01

  No.

• 34:53Sam Parr?

  You want, you don't want to start a company or a business? It doesn't mean she won't. She just doesn't want to.

• 34:57Speaker 01

  I never want to raise money, issue equity, um, or like build a large team again.

• 35:03Sam Parr?

  So do you have, what do you do now? I mean, uh, are you working at Girlboss?

• 35:09Speaker 01

  Yeah, I'm working at Girlboss. Um, I mean, right now it's like, we can't do our conference. Most of our brand partnerships fell through. Um, that's, I mean, we had something signed that was like four times last year's revenue. That would have been a one, one check for a year long deal. That was signed on, you know, the CFO's desk for countersignature and then fucking COVID. So this shit's really affected our business. I have a great operator, I have a great VP of finance. There's obviously Attention Capital who are super dug in, but the fate of Girlboss is really uncertain. And so like everybody else, I've had to think about like, oh shit, what happens if we don't like make it through this?

• 35:54Speaker 01

  Um, no investors just going to indefinitely fund a business that's like, may not be viable for the long term, even though I sold it. Like I don't have control over what happens next. And I'm writing my next book and I'm, you know, doing my stuff like on weekends. Um, but like day to day with Girlboss, I'm really more in a leadership position with the team and spending time with our team and having individual calls with people. We have our daily standups. I'm on those. But like the mechanics of, of like operating the business day to day, I actually have um, a great team who's doing that. So what's next? I really don't want to think or talk about what's next because, you know, of course, we think about the first place we go and um, our future's uncertain is like,

• 36:36Speaker 01

  you know, it's natural and human to just be like, oh shit, what does this mean for me? You know, and um, the fact is I'll be fine. Um, I, I, I do well with what I, you know, between speaking engagements and um, working with friends personally and um, what else? Like books and there's other.

• 36:56Sam Parr?

  Can I ask you a question about Girlboss's business model? Like, I think that for a minute, it was like a social, it was almost like a, a community.

• 37:05Shaan Puri?

  LinkedIn.

• 37:06Sam Parr?

  Yeah, it was like a community. Now it's kind of like a media company. Um, or at least that's what it looks like from the outside. Why don't you guys just charge uh, these people like thirty, fifty bucks a month or something to be part of this community? It seems like it would.

• 37:20Speaker 01

  That would be the initial idea. So venture is interesting, right? You take advice and um, it was built. There's a, there's a paywall that we already built that we were going to launch it and then.

• 37:32Sam Parr?

  That would be a great business.

• 37:34Shaan Puri?

  But she's pointing out it's not a venture scale business.

• 37:37Sam Parr?

  I, I just so disagree with that.

• 37:39Speaker 01

  Before we launched, um, you know, I had a phone call with my investors and they were like, you know, don't reinvent a business model that already works. No one has launched a social network that, you know, you have to pay for. You have to like at least prove yourself first, make it free and then add, you know, premium features. And so a month before launch, and we didn't have great cash flow. We, you know, we were like tied on cash already, launched something that didn't drive revenue because it would be sexier uh, for venture investors and they'd like understand, you know, something that, you know, isn't like a subscription, social network that we've never seen work before. And so um, the media business, which is what we started out with, all of our revenues has been from brand partnerships outside of ticket sales for the conference.

• 38:24Speaker 01

  Um, all of our effort went into building something that would be sexier to venture capitalists because media wasn't, right? Like. No longer or they've already invested in BuzzFeed and Vice and everything else with binary and like everything, those guys took all the money and then the world changed. And rebuilding media companies, unless you're transacting with your consumer directly, which you guys have done such an amazing job at, you're, you know, you're reliant, you're beholden to, to whatever's happening with brands and, you know, media world. So I wanted to build the community that we had offline, online, because it was just so massive and so special. And to be able to connect the women from all the countries that flew in for the rally,

• 39:09Speaker 01

  who paid to put themselves up, who paid for a conference ticket, to give them the opportunity to connect with one another and to bring our community online is a really special thing. And, you know, there's people who couldn't afford 30 bucks a month. So it felt good to bring something truly democratic forward, but it wasn't a great business decision. It hasn't, I mean, obviously it hasn't generated revenue for us, but it's something I'm incredibly proud of.

• 39:35Sam Parr?

  Yeah, I, I, I, I hear everything you're saying. It's, you're kind of put in a, in a hard place here. And that's a bummer because I think that this, I'm looking at it now, I think that, I, I think it, it can, it's, it's great and it can be even better. And it sucks that, that business model was, people persuaded otherwise, because I think that actually the original thing could be awesome.

• 39:59Speaker 01

  Yeah, we were going to build an app this year and that's just kind of on hold at the time being. So we were going to keep growing it.

• 40:05Sam Parr?

  You, so you have a huge network. You have your hand in the mix in a lot of different things. What opportunities in business models and spaces do you think, or are you spending a lot of your time or you're looking at, you're like, oh my gosh, this, this is going to be, this is something incredibly fascinating. You already said the cleaning company, what was it called, Blue Land?

• 40:25Speaker 01

  Blue Land, yeah. So I think sustainability, you know, something else I am looking at called Cloud Paper. That's. It's like a hundred percent bamboo toilet paper, so they cut down like zero trees. They're, they're, they're raising, they have a lead. The lead got in touch with me and I'm just not sure about it, but I think sustainability, I think, I mean, I'm not super deep on fintech, but there's another company called Main Street that's super fascinating who are raising, who, I don't know how to describe it, but usually like government incentives are just this super like opaque world where big companies know what a, whatever opportunity zone is, but like, you know,

• 41:06Speaker 01

  small businesses and venture-backed startups, it's just this like you're piecing together this, all of these possible grants and, you know, stuff that is out there for small businesses. And so Main Street actually consolidates all of that and works directly with Gusto and your, I don't know, whatever your payroll system is and with you directly to just basically, they, they save like on average companies they work with like thirty thousand dollars a year, I think. And so they're kind of like your central hub for those kind of government and incentives and just navigating that world, which is often just very challenging for small businesses.

• 41:51Sam Parr?

  I'm looking at it now. This is awesome.

• 41:52Speaker 01

  Yeah, it's cool.

• 41:54Shaan Puri?

  Yeah.

• 41:55Speaker 01

  It's just like money sitting around, you know?

• 41:56Shaan Puri?

  What, what are you, forgetting about even startups, like those are great actually examples. But in addition, like what are you just interested in learning about? Like what are you like just curious about where you're like, oh, I want to read more about that. I want to talk to people who know about this. Is there anything that's got your curiosity?

• 42:11Speaker 01

  I mean, I'm kind of interested in people who build personal brands because it's just like super weird, but I think it's something like I should be doing more of. But like, I don't need the house and I don't know what I'm supposed to post about. I just like the lean startup, like good and great. Like I just fucking donated all of those books because I'm like, I'm never raising venture capital again. Like I'm, I'm just like so happy to get rid of those books and like, I've got, you know, I've got some meditation books and some design books and some like weird witchy books and books about like building habits.

• 42:47Speaker 01

  I think I'm just, I'm interested in, you know, I've only read nonfiction that like benefits me like right now to build my business. Literally like in 14 years, like all I've read is shit that's like, I can apply this right now. Like, and I wanna read things that like benefit me personally, um, or maybe spiritually, or my, you know, I could become a well-rounded person and I never figured that out. Um, so I think just like things that have less to do with business. Like, I don't really wanna read about business again anytime soon. Um.

• 43:18Sam Parr?

  I, uh, I, I'm in the similar boat with you. I've been reading a lot of fiction, just like American classics, uh, like Catcher in the Rye, just like stuff we used to read in grade school. But I wanna recommend something to you because I, like I said, I think you and I have a little bit similar personalities where like, uh, chaos is kinda like the comfortable place to live in. And, uh, but anyway, there's this great book. It sounds like a horrible book, but your personality is very similar to this guy. His name is, uh, Felix Dennis. Have you heard of this guy?

• 43:47Speaker 01

  Hmm.

• 43:48Sam Parr?

  He's kinda like, he's British, he's dead now. He died of cancer about 10 years ago. He, uh, he started Maxim Magazine. He also started, uh, Micro Warehouse, which was a large publicly traded company. He, if I had to describe him, I would say he's like Richard Branson, but more vulgar and admits to being like a cokehead and like a, and like a Rolling Stones, like, he's kinda like Mick Jagger, if Mick Jagger was like a little bit more responsible and in business. And he's got this great book. It's horribly titled, but bear with me. It's-

• 44:13Shaan Puri?

  Yeah, you, you just can't tell her the title. The, the description was great, but as soon as you say, if you had said the title up front-

• 44:18Sam Parr?

  I don't. I try not telling people the title because it's so off-putting. It's called, what's the title, Sean? Is it, uh, How to, How to Get Rich?

• 44:26Shaan Puri?

  How to Get Rich. That's the name-

• 44:26Sam Parr?

  It's horribly titled, but the, I know, trust me-

• 44:29Speaker 01

  It sounds like offensive or something.

• 44:31Sam Parr?

  But it's like, he, he-

• 44:32Shaan Puri?

  It's, it's exactly what you're saying. You're not interested in these like sort of business books.

• 44:37Sam Parr?

  I know, but he doesn't write that way. He writes in a very, he like, he like loves poetry and he's just such an interesting person. And he, and he like tells funny stories about, it's kinda like, uh, like I said, it's like going on tour, like with the Rolling Stones. That's kinda like what I feel this guy's life is similar to. But he has a lot of amazing, um, advice on how to delegate to your employees- How to hire people, but it's all woven in this kind of like rock star like interesting book. I would highly recommend reading that. It's super interesting. I use it as a reference book now on how to manage people. But it sounds like that book, that guy solved a lot of the problems that you seem to struggle with. It's super interesting, but it is businessy, but it's written in a, in a, in almost like a fiction way.

• 45:21Speaker 01

  Yeah, I have to commit to actually read. I'm like, I skim through books like I let them like the scent. I just let the scent walk up. And I'm like, cool, I get it. Like, I get enough of it. I don't need to finish this book. And honestly, like buying books is like enough of a statement about like, oh, this matters to me. Like, I know it's like spending money, but it's just like, oh, this, it just like solidifies something that's important to you. Like, I'm, I'm going to pay a certain amount of attention to this, even if it's buying a book that sits on my bookshelf.

• 45:52Sam Parr?

  When I fly, I take Xanax because I hate flying and I don't drink alcohol, but I take like a fair bit of Xanax when I fly. And every single time I go to the airport, I leave with $200 worth of books because I'm a little like hopped up. And I'm like, oh, the best books at the airport. You're like, oh, this looks awesome. This like, and I come back with a massive bag.

• 46:09Speaker 01

  I do that with magazines and just like not talking about me anymore.

• 46:16Speaker 01

  I'm kidding.

• 46:17Sam Parr?

  Sean, is there anything else you want to go over?

• 46:20Shaan Puri?

  Uh, no, this has been good. I, I gotta say you are incredibly candid and I appreciate that. You know, I, or I, not even candid, honest, I think is a better way of saying it. Because most, you know, we, we have some people on here and actually we stopped bringing on guests for a while. Cause I was like, what's the point? I don't want this person's infomercial. They're sort of, you know, you try to talk about anything that was difficult or messy. And then they give you kind of like the, the story that's like, I had adversity and I overcame. And it's like, yeah.

• 46:49Speaker 01

  My biggest weakness is that I.

• 46:52Shaan Puri?

  I care too much. Yeah. And so I actually, anytime there's like a guest episode, I'm like, okay, like I get it. You know, I wish we could just have the conversation offline. Honestly, it'd be way more interesting. This was, to me, was like a conversation of if we were, you know, whatever, at the bar, just having drinks. This is that conversation, but, but on a podcast. So I actually really feel grateful that, that we had this conversation.

• 47:13Speaker 01

  Me too. I'm around. Feel free to reach out. I think you have my email. Um, if you, I think you do. But yeah, this has been a blast.