#72 with Sophia Amoruso - GIRLBOSS

This episode is brought to you by Superside, so Superside.com. If you need something designed quickly Go to superside dot com, give'em a try. That was it. Like I didn't have savings. And I went from upgrading from my 87 Volvo to uh a year and a half later fucking Panamera and was like, what is this? I can like buy everyone oysters? That's nuts. What's up? I'm here, Sam's here, and we got special guest, Sophia Amarosa. We're just explaining

what this podcast is and I think we're we're kinda shitty explaining it because Uh most people when they come on a podcast they're like, Okay, cool, these people are gonna interview me And uh we kinda do. We do ask questions'cause 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 um 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. Uh you said that Peter is a national disgrace. You watch The Bachelor. Oh yeah. Yeah. Give me thirty seconds. Why is Peter a national disgrace?

Yeah, my boyfriend was saying last night, he was like, It's okay, like you're into the bachelor. And I was like, I am not into the bachelor and like you watch it every season and 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? Uh, what is that? Like uh Ben Moritz's new buck 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 I think the word is basic. Yeah, basic. I think what people the B word entry level 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 what you want. Why would you want to be that guy? 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. Well I just had just I'm gonna dive deep into all this, but the the first quick question is what type of Porsche do you have?

I don't. That's like that's like many cars ago. What do you have now? 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. And an F type is like a supercar, right?

Or is that the S U. No, it's yeah, it's like a it's like a racy race car. Like the wing it's like the the doors go up. 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 Girl Moss 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. What type of Porsche was it? It's a Panamera. I mean honestly anything other than a Tesla feels like Driving Like an ancient in the past, like why would you pay to

like a hassle with car play or whatever it's called. I I don't know. 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 uh 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, somewhere between thirty and eighty percent of it. And so I got spooked by Dan. I was like okay, I I don't wanna buy this car if this company's not gonna survive uh long term. So that was that was my takeaway. What do you think of that?

Um, I mean I own S Tesla stock and I'm really enjoy the volatility and I'm like in it for the long haul. I yeah, in terms of Tesla being fraudulent, it's like what company isn't at some point. It's like Bake it till you make it. I mean, he's really he's like very much a a liability, but I mean it's just a great product. So also The model X is over six thousand pounds. Which to qualify commercial vehicle, which means you can write it off. Yeah. That's what I ended up doing. I ended up just buying a really big heavy BMW to to write it off.

Yeah. I didn't I didn't know about this. Um so Sophia, uh to the listeners, you I'm gonna give your uh 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 uh I did. I used to work for that TV show called American Pickers. And we would buy buy and sell a ton of old other 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 nasty gal dot com. I mean just like a a proper uh man uh clothing brand. Um, it got quite huge and then it went down as Uh it went down uh As fast as it went up. I mean it was a roller coaster over ride, right?

When you're a lot faster than it. Yeah, it it was a roller coaster. And then you went and launched Girlboss, which uh was a well, it's a whole brand of books and T V shows, but a social networking site and you sold that to uh Nick Bell at Attention Capital, right? Yeah. Um so Joe Marcese, Nick Bell, I don't Nick Bell's not even super involved anymore, so that's interesting. Um, sold the company at the end of last year, um, 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 girl bosses and my biggest supporters, like

but my Android was before I even had a deck, you know, just months after Nasty y'all fell apart, um But yeah, that's the gist of the story. It's a real long story. And when I wrote Girl Boss in twenty fourteen, 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, customers being angry. Um, 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 twenty twenty one. I think I'm calling it tough shit and it's um everything that happened after Girl Boss. So like the two years before uh now so y'all face planted and everything, like a divorce, like everything that could have gone wrong went wrong. It's pretty entertaining. Um How big was Nasty Gal at its peak? Yeah, so we had over a hundred million in revenue and the company was worth like three hundred and fifty million dollars.

Um, so index put fifty million in. I bootstrapped it to twenty eight million profitably. And then adventure investors were like, who is this free? 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 I 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. 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? 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 had a screenshot, like the basic bank America of America, like bank account or And and I and also under it is my personal account and I have something like eight grand. Like I didn't really pay myself. I think the Well the business had a million and you you were all in. 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 50 million on a 350 post. And after that I owned eighty percent of the business. Um where did 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? Yeah, ventures 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 remember how those numbers came about. How did the number'cause 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 what's the valuation? And then they throw out a big number. how totally yeah I mean they wanna own their twenty percent, right? Um and it was a growth.

It was the first money one was out of A brand new growth fund. Right. It was like the second investment out of that after like their big investment in Dropbox at the time. So think growth grounds or you know, people aren't looking to, you know, play small bets. They want to um 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 three hundred and fifty million dollars and we're making like thirty million in revenue? Whatever. I didn't like, you know, have more than one term sheet. I never And I think I might have like bartered the way you 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. Right. Um, it took some money off the table. That was totally life changing. Um you say how much?

Nah. No. How'd you decide to do that?'Cause 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 soak sheets every night either. So how did you decide the amount?

Just pick the number. Yeah,'cause the company didn't need need money. They were just like I didn't know what secondary was and They were like Yeah, like we'll You know, the company doesn't need fifty million, so yeah, we're with the majority of it.

But into the business, but you know, more than half into the business, but um a lot into my bank account'cause it was just it was still it's just just the same stock. Like they have the same position regardless. And you know, at at the growth. you know, stage, especially when Yeah, 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 diluted to the point where you own like ten percent 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 uh 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 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 uh 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? D would the would the company have thrived had it not taken any money?

I don't know. What do you think about it? 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 back 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. The offered over four hundred It's like four hundred and twelve million dollars on um like a piece of paper. when I owned eighty percent of the business and my investor told me to ask for more and it went away.

Fuck. How uh That's Well hold on hold on. We can't change topics. That's amazing. Uh what was that like? 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 bo go big or go home, you know? 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 getting on something else. Yeah, they're like, Why bother? And uh from that point on when we did need to raise capital after that or try to raise capital after that. Or other people like largely when other people came in and were like, Hey, we want to invest out of 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 teet 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 kinda disappear.

For some reason and I didn't really connect the dots. And at a certain point, you know, I six months later, I'd reach out to that person and be like, Whoa, you like totally ghosted what happened? And they're like Yeah, you're 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 uh 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 I didn't know was happening. So why did you raise money again then for Girl Boss? Why I see. And like I could in our 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 Girl Boss is a really powerful brand. It's an amazing opportunity. There was like

so much ground swell behind the brand'cause you know, I s I founded it in twenty seventeen. That was Fourteen three years after you know the book was a bestseller. The hashtag's been used twenty million times on Instagram. And then I started the business'cause I knew there was like this I I had our first conference a month before the Netflix series came out, which was gonna put the name Girl Boss 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 MIT that like catches all that awareness'cause like I can capitalize on that.

Um, and it and I did, um, but not to the point of like, you know, I haven't I didn't sell the company for like Uh Bazillion dollars. So My my company, The Hustle, you know, I don't you I don't I have no idea if you know this or not in Done Matter, but we started as a conference. So I started it Did you read Sam's book? Yeah. Have you read have you have you Googled me? No. I need to read books. It's like a thing. It's like Uh so we started it as HustleCon and so uh 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 on conferences. It gives you a little high too.

They're quite challenging to scale to be very large, um, but it is possible. Um, did you like the conference business? 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 and Women from thirty countrys flew out for

the last one in like forty one states or something. It's just the awareness of Grow Boss 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 um very like broad Um broad like awareness. Um 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. Um, 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. You um you and I are uh 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 uh 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 th 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 uh were you running I don't think you're running Nasty Gal later on, were you? I didn't for the last like couple years. I I like opted out. I was like I wanna be I just don't wanna 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, all of those things are important to me.

the bottom is general management. Like w at the the the bottom. Um So I've had to be an operator in just 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. Um, and I can drive revenue. 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, it 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, um but more than all I'm probably like a voice and a brand you know, creative and a marketer. Do you think that that's the same thing?

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 the famous entrepreneurs are still the the CEOs Um in some cases, I don't know if that's actually the reality, like they have strong operators like uh Uh that it's I think it's more common than people realize. But The 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? 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 brower roll is how I felt. 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. As a negative event when it happens. I mean whatever. I mean, yeah, I thought about how it would be perceived and it was just 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? 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. Um 'Cause I just never it was like never a goal of mine, right?

Um 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'cause I've been like frowned upon like plenty of times much more loud in a much more loud way than having stepped. Like for a much

bigger reasons or noisier. What's an example of those front pun moments? I mean getting sued, going bankrupt, like laying people off, toxic culture. I mean like a Netflix show being like pan um T M Z covering my divorce, like I don't know. Some stuff. And the the skin is thick now or or has been always pretty thick, yeah. Was it was it always that way? Yeah. No, I don't think so. I mean it was until

You know. And 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 t same time I have to first assume that everything is true.

and then we'd out the things that aren't true. Because if I don't consider that things that are said about me are true. 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 your how how other people feel as or you know can't argue with people's feelings, right? Um and you

You're kinda like uh I mean, you're kinda famous. Like you this T V show is quite popular, you have a book all over the place. It seems like you got a pretty big personal audience on uh 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 T M Z and shit like that. I mean, that's like mainstream stuff.

Um, well, I think with T M Z it was like I had a great green up. Um An error yeah. Um that's weird, right? Like you're that's kinda. 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 at community college drop out 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 privil privilege that I started out with, but you know, education and even work working in office or having a manager was not one of them. Like I started a business with the tools that most of 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 don't know what supply chain was or like we weren't I wasn't 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 read the book. So I think it inspired um the rest of the

you know, world or the rest of women who, you know, may be accidental entrepreneurs or have side hustles. um, 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 wanna be like, I give a generation hope, but in some ways I think my story has. Alright, this episode is brought to you by Super Side. So here's the deal. Um I'm incredibly impatient. Like horribly impatient. I get an ide an idea on midnight and on

Eight AM the next day, I want it done. And unfortunately hiring people to get that stuff done is really time consuming. It takes forever. So supersight.com here's what it does. You go to supersight.com, they already have a team of designers ready to go. You tell them what you want and they get it done. It's twenty times faster than traditional hiring and fifty percent more affordable than agencies. If you need something designed and need it done well and fast, Try'em out, super side dot com. I've used them before, love'em. Tell tell us a little bit about the book. So um

Books are a funny thing, right? You y you know, getting one made is this like weird process and then you know, the the point from where you have a story to it sitting in every airport on the you know, on the display stand as like buy this thing. Um, 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 can kind of engineer a lot of the the growth. So how does the book get so popular? How did your book get so popular? Yeah. Um I mean I tried to drive as many pre orders as possible and not see I have a two million person email lists at the time. And for me, this was an opportunity to market our story. It 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 these things felt like marketing coups, not like opportunities to market myself, or it's 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 wow, 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 and spent twenty weeks on the New York Times bestseller list. I do know that you know, Growboss 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 uh if your book doesn't have merit. Um is is five hundred million or sorry, five hundred thousand uh five hundred million would be great, but five hundred thousand book sales, is that a meaningful revenue driver for you? Or that that was good money. Like the the royalty's 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. What's a what's a typical advance for that? Like half a million dollars or something? Oh God now. Uh more or less. I have no idea. That like A lot of editors, you know, even women came to the room, read my um my proposal, whatever you call it, and we're like We think this is too niche. We don't think like that many women like wanna start businesses. They wanna 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 Colin, 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 it 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'cause I don't do a good job. Um Yeah.

And um Uh yeah, there was an advance, but I think it I don't remember. It was like maybe one fifty. Like I don't know. I don't remember, but like 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 this Yeah, I less 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 gonna 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 about it now, but um Basically if you sell five hundred K five hundred thousand dollars worth of books, like, you know, your break even if you sell two hundred and fifty thousand dollars of books, like if you try to know do another book deal, you'll be held accountable to that. So it kinda 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'cause it's easy to be like, cool, I made money, great. All right, about Yeah. Have you so, um uh Tim Ferris was one of our angel investors and we're not I'm not terribly close with him, but w I shoot the shit with him every once in a while. And he has said something like his book was uh great uh like revenue wise at the time, but he goes, My podcast is significantly bigger uh in terms of revenue. And

my angel investing has been way bigger beyond that. Um have you ventured into that world of of uh startup and investing in the early stage companies? 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 money. I don't know if they work only work with like people who they think Wait. At least net worth on paper is like outrageous and mine was like two hundred and eighty thousand million, whatever. Is is iconic Mark Zuckerberg's thing or is I think he yeah, I think that's he's part of it, but it's not his. He's but I

Got it. At some point they manage his money, I don't know who they work with now. Um And um and I was invited to invest in their fund. Um, so I'm an LP in their fund. I put like five hundred K in. Um I put like 150k into indexes fund. This was all back in like 2013, maybe. Um, 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

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 uh bad idea, but Brian Mehan, his CEO is like a great friend, invested in my businesses. Um, and then I've done some angel investing, so I just invested in public dot com. Yeah, I just signed up for it last night. Yeah. So I'm there, I'll follow you. I'll I'll look at it. Your stocks. Um so I'm an advisor and uh

Um an 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 angel investor. So I feel good about that. Um, I invested in something called Blue Land. That's um

Sustainable, yeah, cleaning products where instead of using single use pro 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. So the only thing you buy over and over again is the tablet. Um so the founder Sarah um Paigi U is super um impressive. What else? I invested in Passport, which is like a international logistics company. They just raised a series

A um I'm an advisor there, invest in company called Show House. Um Oh, I invest in liquid death. Um And drinking. What has been the uh most lucrative angel investment you've made? I mean, none of them have returned anything yet. But I think first it is probably like, you know, they've gone on to raise several rounds.

Um, the iconic investment has, you know. They I don't know, there's like Black Line and Alibaba and like a bunch of stuff I invested in back in like twenty twelve, twenty thirteen 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 pay those capital gains, put that shit in the bank just cash, like for now. And then I still have like I have a lot in my house, which is stupid. I'm s overexposed in real estate, but I live here. It's awesome. And um And then 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.

Nice. And w w you know you've done a whole bunch of stuff and I I feel like your your story's cool'cause 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 h you've hiked up this mountain and you're like, wow, okay, I see a whole bunch of other possibilities now. What's like I I don't know, not like a ten 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? 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 Grow boss 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 the all my scars from Nasty Gal by you know building something that Yeah, feels better. Um, 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 fourteen 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. 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 sh we should all be

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 to 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 I 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. 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 wanna have more choices. Like I you know, I I

I at some point wanna just work on a smaller I I don't wanna start a company ever again. So there's that. Um Wait, wait, wait, you don't want to start a business again? No. 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. I never wanna raise money, issue equity, um, or like build a large team again. So do you have

D what do you do now? I mean, uh are you working at Girl Boss? Yeah, I'm working at Girl Boss. 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 an a one one check. for a year long deal. that was signed on you know the CFO's desk for counter signature and then

Again. Okay. So This shit's really affected our business. I have a great operator, I have a great P of Finance, there's obviously attention capital who was super dug in. But the fate of Girl Boss 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.

Um no investor is just gonna indefinitely fund a business that's like m 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 Girl Boss, 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 stand ups, 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 wanna think or talk about what's next because, you know, of course we think about the first place we go when um our future's uncertain is like, you know But it's natural and human.

Just be like oh shit. was me 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 brands.

personally and Um what else? Like books and there's other things. Can I ask you a question about Girl Boss's business model? Like I think that for a minute it was like a social n it was almost like a uh a community. Yeah, it was like a community. Now it's kinda 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 the this community. It seems like it would take a little bit of a initial idea. So

Venture's interesting, right? You take advice and Um it was built. There's a there's a paywall that we already built that we were gonna launch with and then That would be a a great business. But she's pointing out it's not a venture scale business. I I just so disagree with that. 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 didn't you know, we were like tight 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 revenue has has been from brand partnerships outside of ticket sales for the conference. Um, all of our effort went into building something that would be sexier to venture capitalists. Because media wasn't, right? Like no longer are they've already invested in BuzzFeed and Vice and everything else refinery like everything. Those guys took all the money and then the world changed and be building media companies unless you're transacting with your consumer directly.

Which you guys have done such an amazing job at. Um, you're, you know, you're reliant, you're beholden to to whatever's happening with brands in 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 who paid to put themselves up. who paid for a conference t conference ticket to give them the opportunity to connect with one another and to bring our community online is a really special thing and

Yeah, there's people who couldn't afford thirty bucks a month. So it felt good to bring something Truly democratic. Um 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.

Yeah, I uh I I I hear everything you're saying. It it it's it's you're kinda put in a in a hard place here. Um and that's a bummer because I think that this I'm looking at now, I think that uh I I think it it it can it's it's great and it can be even better and uh it sucks that That business model was

people persuaded otherwise'cause I think that actually the original thing could be awesome. Yeah, we were gonna build an app this year and that's just kind of on hold, I think we were gonna keep growing it. You um so you have a huge network, you have your hand in the mix and a lot of different things. What opportunities uh b in business models and spaces do you think uh or are you spending a lot of your time or you're looking at you're like oh my gosh this this is gonna be uh this is is something incredibly fascinating. You already said the uh cleaning company blue what was it called Blue Land? Blue land, yeah. So I think sustainability, you know, is something else I I'm looking at called cloud paper. That's um It's like A hundred percent bamboo toilet paper. So they cut down like zero trees.

Um They're they're they're raising, they have a weed. no we got in touch with me and I'm just not sure about it. But I think sustainability, I think I mean I I'm not super deep on fintech, but there's another company called Main Street that's super fascinating who are raising, um, who I don't know how to describe it, but usually like government incentives are just this super like opaque world where Um big companies know what a uh whatever opportunity zone is, but like, you know, small businesses and venture back startups. It's just this like you're piecing together this

all of these um possible grants and um Yeah, stop that is out there for small businesses and so Main Street actually consolidates all of that and works directly with Gusto and your um 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. Um, and so they're kind of like your um central hub for those kind of government And incentives and um just navigating that world which is I can just

very challenging for small businesses. I'm looking at it now. This is awesome. Yeah, it's cool. Yeah, I like it. What what do you forget about even startups, like those are great uh 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 wanna read more about that, or I wanna talk to people who know about this. Is there anything that's got your Curiosity.

Yeah. I mean, I'm kind of interested in people who build personal brands'cause 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. Um, I just like the lean startup. Like good degree. 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. Um 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 fourteen 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 can 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 want to read about business again anytime soon. Um 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 w 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? Mm-hmm.

He's kinda like He's British. He's dead now. He died of cancer about ten 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 title, but bear with me. The description was great, but as soon as you say if you had said the title up front, I don't. I try not telling people the title because it's it's so off putting. It's called what's the title, Sean? Is it uh How to G How to Get Rich? How to get rich. Doesn't it. It's horribly titled, but the I know it's like offensive or something. But it's like He he i it's w it's exactly what you're saying you're not interested in, these like sort of business books. 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 ta 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 I 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 um hire people. But it's all woven in this kind of like rock star like uh interesting book. Uh I would highly recommend reading that. It's super interesting. I use it as a reference book now on how to manage people. But uh It sounds like that book, that guy solved a lot the problems that you uh 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. Yeah, I have to commit to actually read I'm like I skim through books like I

Let the mic uh the scent. I just let the scent walk up. And I'm like It's like a candle. 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. Yeah. It just like Solidify something that's important to you. Like I'm

I'm gonna pay certain amount of attention to this even if it's buying a book that sits on my bookshelf. When I fly, I take Xanax because I hate flying and I 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 two hundred dollars worth of books'cause I'm a little like hopped up and I'm like, Oh the best books are at the airport. You're like, Oh, this looks awesome. This look and I come back with a massive bag of books. Not talking about me anymore. Okay. Um Sean, is there anything else you want to go over?

Uh no, this has been good. I I Gotta say, you are incredibly candid and uh appreciate that. You know, I I I get it. Honest, I think is a better way of saying it. Um because Mo you know, we we have some people on here and actually we stopped bringing on guests for a while because I was like, What's the point? I don't want this person's infomercial Um, 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 weaknesses. But 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 what to me was like a conversation of

If we were, you know, whatever at the bar just having drinks, uh, this is that conversation, but but on a podcast. So I actually really feel grateful that That we had this conversation. So I'm around. Feel free to reach out. I think you have my email. Um If you d if you I think you do.

Um But yeah. This has been a blast.

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