My First Million - #72 with Sophia Amoruso - GIRLBOSS

Episode Date: May 6, 2020

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.

This episode is brought to you by Superside.com. So Superside.com, if you need something designed quickly, go to superside.com. Give them a try. 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 Panamara 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 Emeroso. We're just explaining what this podcast is. And I think we're kind of shit. 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 really the overall vibe of the podcast. And so we can start with whatever. Sam's read your book. I've read your Twitter. I have a question off your Twitter. That's just a, the fun little icebreaker.

I saw that you tweeted a very controversial tweet. Actually, not so controversial because many people would agree. You said that Peter is a national disgrace. You watch The Bachelor. Oh, yeah, yeah. Give me 30 seconds. Why is Peter a national disgrace? 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 I guess what you do is who you are, right? What is that?

Like Ben Horowitz's new book or something? He's like a dupe. He's just like the most generic. I just don't know how you find people that generic. Yeah, there's just like no deviance whatsoever. And that just like creeps me out. I think the word is basic. Yeah, basic.

I think what people. The B word. Like entry level human. This guy's, yeah, he's pretty, he's pretty universal. disliked as the Bachelor. Nobody he dislikes him because he's not controversial. He doesn't do anything necessarily that bad. He doesn't also do anything, period.

He's sort of a non-decision maker, which is what you want. He just like flip-flops and hurts people. Why would you want to date that guy? Not great. Okay, so that's your thoughts on The Bachelor. Sam, you read the book, so I think you have maybe some more interesting questions than I did. Well, I just had, just, I'm going to dive deep in all those.

But the first quick question is, what type of Porsche do you have? I don't. That's like many cars ago. What do you have now? I did the portion. Then I did, 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. Well, an F-type is like a supercar, right? Or is that the SUV? No, it's yeah. It's like a, it's like a racy race car. Right. It's like the wing. The doors go up.

I don't think they go up, but I do have the model. X now and the doors do go out. So I had the F-type and then I had a range rover for like five years. I wrote Girl Boss like seven years ago. So I've been through many cars and now I drive the model X and I like it a lot. What type of Porsche was it? It's a Panama. Worth it or not? I hear mixed things on that. It's a huge car. I mean, honestly, anything other than a Tesla feels like driving like an ancient in the past. Why would you pay to like hassle with car play or whatever it's I was about to buy the Model X 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, like great product, but the company is sort of in dire straits financially. And it's pretty convincing if you end up going down there, like most conspiracies. If you sort of go down that road, you'll end up believing, you know, somewhere between 30 and 80% of it. And so I got spooked by the end. I was like, okay, I don't want to buy this car if this company's not going to survive long term. So that was my takeaway. What do you think of that? 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's 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 the commercial vehicle, which means you can ride it off. Yeah, that's what I ended up doing. I ended up just buying a really big heavy BMW to write it off.

Yeah. I didn't know about this. So, Sophia, to the listeners, you, I'm going to give your, I'm going to tell folks what I know about you, which is that you started as it was nasty gal. Originally, it was a vintage clothes shop, which I did. I used to work for that TV show called American Pickers. and we would 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 nastygal.com.

I mean, just like a proper 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? And then you... We're a lot faster than it. It was a roller coaster. And then you went and launched Girl Boss, 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? Yeah. So Joe Marquezzi, Nick Bell, Nick Bell is 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 Girl Bosses and my biggest supporters, like put money into Girl Boss before I even have. of deck, you know, just months after nasty elf fell apart. But yeah, that's the gist of the story. It's a real long story. And when I wrote Girl Boss 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 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 going to be out until 2021. I think I'm calling it tough shit. And it's everything that happened after a girl boss. So like the two years before Nasty L face planted and everything, like a divorce, like everything that could have gone wrong with. It's pretty entertaining.

How big was Nastygal at its peak? Yeah. So we did over $100 million in revenue. And the company was worth like $350 million. So index put $50 million in. I bootstrapped it to $28 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 $2.

And then you invest like $1.25 and like don't spend more money than you have. Like how else are you going to have a business if it doesn't like produce money? I just didn't. 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 28 million in sales bootstrapped, what were, what was the income off? What's an income off 28 million for that type of business? What was the profit? I don't even remember, honestly. I was just like, at that point, I'd save over a million dollars in just cash in the bank. Like, I have a screenshot, like the basic Bank of America, like bank account where, and also under it is my personal account. and I have something like eight grand.

Like I didn't really pay myself. I didn't even want that. Well, the business had a million and you were all in. I just like, I mean, I was all 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 100% of the company until index came in in 2012 and invested 50 million on a 350 post. And after that, I owned 80% of the business. So that's correct. 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 taken off? Let's go talk to her about venture capital. 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? So I, you know, I didn't, we didn't need the capital, but I was like, whoa, 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 to remember how those numbers came about? How did the number? Because 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 I'm like, what? Okay, seven million. That sounds good. What was the valuation? And then they throw out a big number.

Totally, yeah. I mean, they want to own their 20%, right? And it was a growth. It was the first money you own 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 I think growth rounds are, you know, people aren't looking to, you know, play small bets. They want to own, they want to own a significant amount of the 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, like a like an estate sale. And I was like, no, this much for this much. And that was like, that was it. Right. It took some money off the table. That was totally life changing. Can you say how much? No. No. 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 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? You just picked the number. Yeah, because the company didn't 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 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 diluted 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 Nasty Dow. 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. And I went from, you know, driving like, you know, upgrading from my 87 Volvo to a Nissan

Marano to like, you know, a year and a half later fucking Panama and was like, what is this? I can like buy everyone oysters. That's that. Would the company have thrived had it not taken any money? I don't know. What do you think? 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 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. Yeah, I think so. Like, I think I probably would have

sold the company for, like, a fair amount of money. I mean, at one point, there was an urban clothing retailer that offered over $412 million on, like, a piece of paper when I owned 80% 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 going to 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 go big or go home, you know. If they invest at 350 and it returns at 400, that's not a win. That's an opportunity.

lost. They could have been betting on something else. Yeah, they're like, why bother? And from that point on, when we did needs 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 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 it and 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, you like totally ghosted what happened. And they were like, yeah, 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. when we could have had, you know, much better terms, two years or 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 what's happening. So why did you raise money again then for Girl Boss? Why? Honestly, I don't know. Because I, like, I, like, wanted to do a conference and it wasn't, the conference was initially profitable, 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 a paycheck for the rest of my job.

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 groundswell behind the brand because, you know, I founded it in 2017. That was whatever, fortune three years after, you know, the book was a bestseller. The hashtag's been used 29 times on Instagram. And then I started the business because I knew there was like this. I, I had our first conference a month before the Netflix series came out, which was going to put the name Girl Boss and do 150 million homes in 195 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 haven't, I didn't sell a company for like a bazillion dollars, whatever. So my company, the hustle, you know, I don't, I don't, I don't idea if you knows or not and it doesn't 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 remember the last I need to read books it's like a thing it's like how much right uh so we started it as hustle con 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 on 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? 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 30 countries flew out for the last one in like 41 states or something. It's just the awareness of Grobos 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 L.A. 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. 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 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 in Sean as well in that it seems like you're a very creative. You're a pretty good business person, but you're more so creative than anything. And do you, 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

Nastygal later on, were you? I didn't for the last, like, couple years. 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. just by the sheer nature of having founded companies. I'm not very good at it. 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. 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 happen to build, like, big businesses. But more than all, I'm probably like a voice and a brand, you know, creative and a marketer. Do you think that that, a lot of people 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 famous entrepreneurs are still the CEOs.

In some cases, I don't know if that's actually the reality. Like, they have strong operators. 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? 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. 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 to the- No, I don't give a fuck how it's perceived. I'm saying a lot of people inaccurately, like, 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 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 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. Because I just never, it was like never a goal of mine, right? So like I don'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 it just, I think it's fallen into the background because I've been like frowned upon like plenty of times, much less. more loud in a much more loud way than having stepped down, like for much bigger reasons or noisier. What's an example of those frowned upon moments? 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.

And the skin is thick now or has been? Pretty thick. Yeah. Was it always that way? No. No, I don't think so. I mean, it was until, you know, and then 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, 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, 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. 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 long 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 other people feel as, you know, can't argue with people's feelings, right?

And you, you're kind of like, I mean, you're kind of famous. Like, this TV show is quite popular. You have a book all over the place. It seems like you got a pretty big personal audience on 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 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. Well, I think with TMZ, it was like, if the Amrers, it would call it to quits like a girl boss pays acts of pittance. I had a great pre-in-up. Because that's weird, right? Like, you're, that's kind of mainstream. My story is a rare one, which has made things a lot more difficult for me.

But at the same time, you know, I'm a community college dropout from Sacramento. Every other business book or anyone, any other story. even of women for the most part that you hear, they have like a leg up in some way. Not to say that, you know, 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 don't know what supply chain was or like, We weren't, I was in 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, 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 Gabe, 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. All right, this episode is brought to you by SuperSide. So here's the deal.

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It's 20 times faster than traditional hiring and 50% more affordable than the agencies. If you need something designed and need it done well and fast, try them out. Superside.com. I've used them before. Love them. Tell us a little bit about the book. So books are a funny thing, right? 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 growth. So how does a book get so popular?

How did your book get so popular? Yeah. I mean, they tried to drive as many pre-orders as possible and not see how to two million person email. 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, which isn't like, oh, wow, I never knew that putting myself on

the cover of a book when 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 20 weeks on the New York Times bestseller list. I do know that, you know, Girl Boss 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. Is 500 million, or sorry, 500,000, 500 million would be great, but 500,000 book sales. Is that a meaningful revenue driver for you? That was good money. 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? What's a typical advance for that? Like half a million dollars or something? Oh, God, no. More or less.

I have no idea. Less. Less. Like, I mean, I was just like an unproven author with the story that like a lot of editors, you know, even women came to the,

room, read my proposal, whatever you call it, and we're 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 Colon, who was at Penguin at the time, she's at Audible now, was like, yeah, I get it. Awesome. And she was kind of, I mean, she made the book better, but she wasn't.

She didn't try to make the book what she thought she wanted to be. she just let me run and write a book. And that's when I do my best. I cannot be told what to do because I don't do a good job. And yeah, there was an advance, but I think I don't remember. It was like maybe 150. 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. Yeah, I still don't think that I've done a good job with my existing book deal. and I'm 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 500K, like you make that 250 on top of a 250K, you know, let's see, like, I don't know, I'm about it now. But basically, if you sell 500K,000 dollars worth of book, like, you know, year break even. If you sell $250,000 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 make the same amount of money and actually be incentivized out-earn your advance if it's not that big because it's easy to be like, cool, I made money. Great. I don't write about, you know. Have you, so 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. Have you ventured into that world of startup investing in the early-stage companies? Yeah. So back when I got that like big windfall of money, I worked with Iconic, like Mike Anders and those guys like awesome money. I don't know. They've worked, only worked with, like, people who they think who's at least network on papers, like outrageous. And mine was like $2,000,000,

whatever. Is iconic Mark Zuckerberg's thing? Or is I kind of like? Yeah, I think that's, he's part of it, but it's not his. But they, at some point they manage this 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 their fund. I put like 500k in. I put like 150k into indexes fund. This was all back in like 2013 maybe. I put like 150k into first dibs back then. I was invited to invest in blue bottle at the time and I was 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 bad idea. But Brian Meehan, the CEO is like a great friend invested in my businesses. And then I've done some angel investing. So I just invested in public.com. Yeah, I just signed up for it last night. Yeah. So I'm on there. I'll follow you.

I'm, yeah. Your stocks. So I'm an advisor 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. I invested in something. called Blue Land. It's like sustainable. Yeah, cleaning products where instead of using single-use plastics where you're buying like

Windex and 80, 90% 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

Paiji Yu is super impressive. What else? I invested in Passport, which is like an international logistics company. They just raised it series A. I'm an advisor there. I invested in coming called Chill House. Oh, I invested in liquid death. I've been drinking it.

What has been the most lucrative angel investment you've made? I mean, none of them have returned anything yet. But I think First Tibbs 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 was 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 going to like pay those 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 over exposed in real estate. But I live here. It's awesome. And, and then I have. Are you an. I'm a bunch in like Morgan Stanley now. He manages that stuff. I'm in L.A. I'm up in the hills. It's really great. 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. Yeah. What's like, I don't know, not like a tenure plan, but like what do you see yourself doing going forward? Like, are you going to start more businesses?

What do you want to do? 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 girl 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 all my scars from nasty gal by you know building something that you know feels better um but I didn't you know things I put things into the world that just like have momentum and then that's my life.

It's been 14 years since I founded Nastygal. I did that for a decade. And this quarantine thing has had me being like, wow, like this is really different. 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. I mean, of course we should. We should. 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 into the world just catch fire in that way. But that leads me to in some ways just being like be holden to the opportunity, which is like,

oh, boo-hoo, right? It's like, I 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. And I'm feeling like, you know, in the future I want to have more choices. Like I, you know, I, at some point want to just work on a smaller, I don't want to start a company ever again. So there's that. Wait, wait, wait.

You don't want to start a business again? No. You don't want to start a company or a business? It doesn't mean she won't. She just doesn't want to. I never want to raise money. money, issue equity, or like, build a large team again. So do you have, what do you do now?

I mean, are you working at Girl Boss? Yeah, I'm working at Girl Boss. I mean, right now, it's like we can't do our conference. Most of our brand partnerships fell through. 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 counter signature and then fucking COVID. So this shit's really affected our business.

I have a great operator, have a great VP of finance. There's obviously attention capital who are 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? 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.

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 like operating the business day to day, I actually have 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 our future's uncertain is like, you know, it's natural and human to just be like, oh, shit, what does this mean to me? You know, and the fact is I'll be fine. I, I, I, do well with what I, you know, between speaking engagements and working with brands personally

and what else, like books and there's other. Can I ask you a question about Girl Bosses? business bottle. Like, I think that for a minute, it was like a social, it was almost like a community. Yeah, it was like a community. Now, it's kind of like a media company, or at least that's what it looks like from the outside. Why don't you guys just charge these people like 30, 50 bucks a month or something to be part of this community? It seems like it would be. That would be the initial idea. So venture is interesting, right? You take advice. And it was built. There's, There's a paywall that we already built that we were going to launch it. That would be a great business.

But she's pointing out it's not a venture scale business. I just so disagree with that. Before we launched, 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 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 the media business, which is what we started out with, all of our revenues has been brand partnerships outside of ticket sales for the conference. 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 be building 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 whatever's happening. happening with brands and 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 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 in 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. Yeah, I hear everything you're saying. It's, you're kind of put 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 think it can, 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. Yeah, we were going to build an app this year and that's just kind of unfolded. We were going to keep growing it. So you have a huge network. You have your hand in the mix and 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 it? You're like, oh, my gosh, this is going to be, this is something incredibly fascinating.

You already said the cleaning company. What was it called Blue Land? Blue Land. Yeah. So I think sustainability, you know, something else I'm looking at called cloud paper. That's, it's like 100% bamboo toilet paper. So they cut down like zero trees. 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 fast. fascinating who are raising, who I don't know how to describe it, but usually like government incentives are just the super like opaque world where big companies know what a, whatever

opportunity zone is, but like, you know, 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 whatever your payroll system is and with you directly to just basically they save like on average companies they work with like 30,000 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. I'm looking at it now. This is awesome.

Yeah, it's cool. Yeah. You're just like mind sitting around, you know? 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? 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 leave the house. and I don't know what I'm supposed to post about. 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 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. 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 as shit that's like I can apply this right now.

Like and I want to read things that like benefit me personally or maybe spiritually or my, you know, I can become a well-rounded person and I never figured that out. 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. I'm in the similar boat with you. I've been reading a lot of fiction, just like American classics, like Catcher in the Rye, just like stuff we used to read in grade school. But I want to recommend something to you because I, like I said,

I think you and I have a little bit similar personalities where like chaos is kind of like the comfortable place to live in. 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 Felix Dennis. Have you heard of this guy? he's kind of like he's British he's dead now he died of cancer about 10 years ago he uh he started maxin magazine he also started a 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 rolling stones like he's kind of 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 it's yeah you just can't tell her the title the description of 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 so off-putting. It's called, what's the title shot? Is it, how to get rich? How to get rich. That's the name. It's horribly titled, but that I know. Trust me. Like, offensive or something. But it's like, he, 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, and he, like, tells funny stories about, it's. It's kind of like, like I said, it's like going on tour, like with the Rolling Stones. That's kind of like what I feel this guy's life is similar to. But he has a lot of amazing 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 almost like a fiction way 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 walked up and i'm like it's 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

and do like I'm I'm going to 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 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 with the 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 and I come back with a massive bag. I do that with magazines and just like not talking about me anymore I'm kidding. Sean, is there anything else you want to go over?

No, this has been good. I got to say you are incredibly candid and I appreciate that. You know, I, not even candid, honest, I think is a better way of saying it. Because, you know, 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. 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 story that's like I had adversity and I overcame. And it's like, yeah.

My biggest weakness is that 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, to me, was like a conversation of if we were, you know, whatever, at the bar, just having drinks, this is that conversation, but on a podcast. So I actually really feel grateful that that we had this kind of.

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