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SPEAKER_00
That was it, like I didn't have savings and I went from upgrading from my 87 Volvo to a year and a half later, fucking Panamera and was like, what is this? I can like buy everyone oysters, that's nuts.
SPEAKER_02
What's up? I'm here, Sam's here and we got special guest, Sophia Amoroso, we're just explaining what this podcast is and I think we're kind of shitted explaining it because most people when they come on a podcast, they're like, okay, cool, these people are gonna 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 this 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 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 watched The Bachelor.
SPEAKER_02
Give me 30 seconds, why is Peter a national disgrace?
SPEAKER_00
Oh man, my boyfriend was saying last night, he was like, it's okay, you're into The Bachelor and I was like, I'm not into The Bachelor and he's like, you watch it every season, I'm 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, Ben Horitz'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 deviants whatsoever and that just like creeps me out.
SPEAKER_01
I think the word is basic. Yeah, basic. I think what people- I think that is the B word.
SPEAKER_00
Entry level human.
SPEAKER_02
This guy's, yeah, he's pretty universally 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,
SPEAKER_00
which is what you want. Yeah, he just like flip flops and hurts people. Why would you want to date that guy?
SPEAKER_02
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.
SPEAKER_01
Well, I just had, I'm gonna dive deep into all this, but the first quick question is, what type of Porsche do you have?
SPEAKER_00
I don't, that's like many cars ago.
SPEAKER_01
What do you have now?
SPEAKER_00
I did the Porsche and 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.
SPEAKER_01
Well, an F-Type is like a super car, right? Or is that the SUV?
SPEAKER_00
No, it's yeah, it's like a race car.
SPEAKER_01
Right, it's like the wing, the doors go up.
SPEAKER_00
I don't think they go up, but I do have the Model X now and the doors do go up, but so I had the F-Type and then I had a Range Rover for like five years. I rode Girlboss like seven years ago, so I've been through many cars and now I drive the Model X and I like it a lot.
SPEAKER_01
What type of Porsche was it? It's a Panamera. Worth it or not? I hear mixed things on that.
SPEAKER_00
It's a huge car. I mean, honestly anything other than a Tesla feels like driving like an ancient. In the past.
Like why would you pay to like hassle with CarPlay or whatever it's called? I don't know.
SPEAKER_02
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. I 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, some of them 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?
SPEAKER_00
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 as a commercial vehicle, which means you can ride it off.
SPEAKER_02
Yeah, that's what I ended up doing. I ended up just buying a really big, heavy BMW to ride it off.
SPEAKER_01
Yeah. I didn't know about this. So Sophia, to the listeners, you, I'm going to give your, I'm going to tell you folks what I know about you.
And which is that you started as, it was Nasi Gal. Originally it was a vintage clothes shop, which I did. I used to work for that TV show called American Pickers and we went by 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 scale that to just NasiGal.com. I mean, just like a proper, a menu, a 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? One roller coaster, wasn't 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?
SPEAKER_00
Yeah. So Joe Marcazi, Nick Bell, I don't, Nick Bell's not even super involved anymore. So that's interesting.
Sold the company at the end of last year to, you know, Joe's like been a friend of mine for like five or six years, just someone like I really love. He's been one of Girl Bosses and my biggest supporters, like put money into Girl Boss before I even had a deck, you know, just months after NasiGal 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 had 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 Tuff Shin. And it's everything that happened after Girl Boss.
So like the two years before NasiGal face planted and everything like a divorce, like everything that could have gone wrong went wrong. It's pretty entertaining.
SPEAKER_01
How big was NasiGal at its peak?
SPEAKER_00
Yeah, so we had over a hundred million in revenue and the company was worth like $350 million. So index put 50 million in. I had boots dropped it to 28 million profitably.
And then adventure investors were like, who is this brief? Because the only thing I understood was you buy something for a dollar and you sell it for $2 and then you invest like a dollar 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, 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.
SPEAKER_01
Well, and at 28 million and sales bootstrapped, what was the income off? What's an income off 28 million for that type of business?
SPEAKER_00
What was the profit? I don't even remember, honestly. I was just like, at that point I had saved over a million dollars in just cash in the bank. Like I have a screenshot of like the basic bank 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.
SPEAKER_01
Well, the business had a million and you were all in.
SPEAKER_00
I just like, I mean, I was all in in that like, 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 great.
SPEAKER_02
Where did the index come from? 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.
SPEAKER_00
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 two things.
SPEAKER_02
How did these 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's the valuation? And then they throw out a big number.
SPEAKER_00
How did they know? Yeah, I mean, they want to own their 20%, right? And it was a growth. It was the first money one was out of a brand new growth fund. It was like the second investment out of that after like their big investment in draw box at the time.
So think growth grounds or, you know, people aren't looking to, you know, place small bets. They want to own, they want to own a significant amount of money and then, or the business. And I didn't like game it.
Like I didn't, I was just like, whoa, that's crazy. You think it's worth $350 million? 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 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.
SPEAKER_02
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 cool with it if you have momentum, but they're also like, look, we're not, we don't want you sort of sleeping in silk sheets every night either. So how did you decide the amount? You just picked a number?
SPEAKER_00
Yeah, cause 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. Cause it was just, it was still, it's just the same stock. Like they have the same position regardless.
And, you know, at the growth, you know, stage, especially when the entrepreneurs, you know, still owns a significant amount of the company. Like you're incentivized, even if you do take a lot of money off the table, if you're not deluded to the point where you own like 10% of the company and like, you know, have like, fuck you money, then like that's a different position. But for me to have that big of a statement in nasty gal.
And, and yeah, like be able to like not worry about, you know, their whole thing is like, we don't want you to like worry about money. Which at the time was like, I had a paycheck, but like that 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 Murano to like, you know, a year and a half later, fucking Panamera and was like, what is this? Like, and like by everyone oysters, that's nuts.
SPEAKER_01
Would the company have thrived? Had it not taken any money?
SPEAKER_00
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-backed businesses and, you know, understand, you know, wild expectations that, you know, when it was a bootstrap business, we just didn't have it all.
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.
SPEAKER_02
How, that's... Well, hold on, hold on. We can't change topics.
That's amazing. What was that like?
SPEAKER_00
It was like whatever, you know, they were convinced that they were like, no, it's 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 go big or go home, you know?
SPEAKER_02
If they invest at 350 and it returns at 400, that's not a win. That's an opportunity lost.
SPEAKER_00
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 at this valuation, that was still like a healthy retail valuation. I was cock-blocked.
Like they didn't have control, but there would be side conversations, you know, after like I teed someone up and they were totally bought in, they'd be like, great, I'd love to talk to your board member. And I love this guy, always love this guy. And after like 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 started us out for a long time when we could have had much better terms, two years, a year and a half before Nasty Gal fell apart.
I just, you know, that was stuff that I wasn't, I didn't know what's happening.
SPEAKER_01
So why did you raise money again then for Girl Boss?
SPEAKER_00
Why? I don't know, honestly, I don't know. I was 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 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 grounds well behind the brand because, you know, I founded it in 2017, that was whatever, fortune three years after, you know, the book was the best seller, the hashtag has been used 20 million times on Instagram.
And then I started the business because I knew there was like this, I had our first conference a month before the Netflix series came out, which was gonna put the name Girl Boss into 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 didn't sell a company for like a bazillion dollars.
SPEAKER_01
So my company, the Hustle, you know, I don't know, I have no idea if you know this or not and done matter, but we started as a conference. So I started it.
SPEAKER_02
Did you read Sam's book?
SPEAKER_01
Yeah, have you read, have you Googled me?
SPEAKER_00
No, I'm not gonna go last, I need to read books.
SPEAKER_01
It's like a thing. It's like how much? That's all right. So we started it as HustleCon.
And so we get up until the stupid stuff going on now, tens of thousands of attendees. And I use like 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?
SPEAKER_00
As a business, no, but as like an event, yeah. Like it's really fun. It's really fun to see these women from our community coming out and meeting one another.
Women from 30 countries flew out for the last one in like 41 states or something. It's just the awareness of GroBoss 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 it's still largely in LA and New York, but very like broad, broad like awareness.
And so to see just like all these awesome women descend on Los Angeles and New York and get so much out of it is a great feeling. 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.
SPEAKER_01
You and I are from, you know, I feel like I know you and even though you have no idea who I am because I've listened to your podcast and read your book. So I feel as though we're a little bit similar and Sean as well in that it seems like you're a very creative, you're a pretty good business person, but you're more so creative than anything. And 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 were running Nasty Gal later on, were you?
SPEAKER_00
I didn't for the last like couple of 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 in 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 happened to build like big businesses. But more than all, I'm probably like a voice and a brand, you know, creative and a marketer.
SPEAKER_01
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 like, 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?
SPEAKER_00
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.
SPEAKER_01
But that's what I'm saying, that is frowned upon. Like, 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.
SPEAKER_02
As a negative event when it happens. Yes, no, no.
SPEAKER_00
I mean, whatever. I mean, yeah, I thought about how it would be perceived and it was just-
SPEAKER_01
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?
SPEAKER_00
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 don't, I tried to name everyone in the company a co-founder but they just like didn't catch on. Like I was like, cool, you're all co-founders. Put that on your LinkedIn.
Like I don't care. Cause I just never, it was like never a goal of mine. Right? So like I don't, 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.
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 down. Like for much bigger reasons or noisier.
SPEAKER_02
What's an example of those frowned upon moments?
SPEAKER_00
I mean, getting sued, going bankrupt, like laying people off, toxic culture. I mean, like a Netflix show being like hand TMZ covering my divorce, like I don't know, just some stuff.
SPEAKER_02
And the skin is thick now or has been in the ways?
SPEAKER_00
Pretty thick, pretty thick, yeah.
SPEAKER_02
Was it always that way?
SPEAKER_00
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 judge you, it's just kind of like, they're totally unqualified, but, and people's, 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 do have thick skin, but at the same time, I have to first assume that everything is true and then weed out the things that aren't true. Cause if I don't consider the 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, no, 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?
SPEAKER_01
And you, you're kind of like, I mean, you're kind of famous. Like you, this TV show is quite popular. You have a book all over the place.
It seems like you've got a pretty big personal audience on a 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, why do you think like they're writing about you on TMZ and shit like that? I mean, that's like mainstream stuff.
SPEAKER_00
Well, I think with TMZ, it was like, so the embers would call it to quit so the girl boss pays ex-affidants. I had a great green up. An area.
Cause that's weird, right? Like you're, that's kind of- Like 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 at 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 have, 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, I was manufacturing things. I just had access to stuff that everyone has access to.
And I had probably less of an education than most of the people who wrote the book. So I think it inspired the rest of the, you know, world or the rest of women who, you know, maybe accidental entrepreneurs or have side hustles who didn't feel qualified. And that someone who was totally unqualified on paper was able to pull off what I did.
I think gave like, in some ways, I don't want to be like, I give a generation hope, but in some ways I think my story has.
SPEAKER_01
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SPEAKER_02
Tell us a little bit about the book. So books are a funny thing, right? You, you know, getting one made is this like weird process. And then, you know, the point from where you have a story to it's sitting in every airport on the, you know, on the display stand as like by 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 the book get so popular? How did your book get so popular?
SPEAKER_00
Yeah, I mean, I tried to drive as many pre-orders as possible and I see how to 2 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 too. Like all of 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 books sold books, and like my story, which isn't like, oh, 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 20 weeks on the New York Times bestseller list. Like, do you 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.
SPEAKER_01
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 or?
SPEAKER_00
That was good money. Like the the royalties like trickle in now, but for those first few years, that was like meaningful for me, which I did not expect. Like I earned out my advance like by multiples, you know.
SPEAKER_01
What's a typical advance for that, like half a million dollars or something?
SPEAKER_00
Oh, God, no. 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 an 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.
SPEAKER_02
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.
SPEAKER_00
Like, it's 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 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 bad at math.
But basically, if you sell 500K, $500,000 worth of books, like, you know, you're break even. If you sell 250,000 dollars of books, like if you try to do another book deal, you'll be held accountable to that. So it kind of doesn't really matter.
You'll say make the same amount of money and actually be incentivized to out earn your advance if it's not that big. Because it's easy to be like, cool, I made money, great. And I write about, you know.
SPEAKER_01
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 out 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 and investing in the early stage companies?
SPEAKER_00
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 only worked with like people who they think who's at least networked on papers, like outrageous and mine was like 280,000 million,
SPEAKER_01
whatever at this time. Is Iconic Mark Zuckerberg's thing? Or is I kind of like?
SPEAKER_00
I think he's, yeah, I think that's, he's part of it, but it's not his, he's, but they. Got it. At some point they managed his money.
I don't know who they work with now. And I was invited to invest in their fund. So I'm an LP in 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 BlueBottle at the time. And it's like, I didn't drink coffee yet.
So I was like, I can't invest in things they don't understand. I like furniture and to a bad idea, but Brian Mehan, 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.
SPEAKER_01
Yeah, I just signed up for it last night. Yeah. So I'm. You want it there?
SPEAKER_00
I'll follow you.
SPEAKER_01
I'll look at your stocks.
SPEAKER_00
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 per angel investor. So I feel good about that.
I invested in something called Blue Land. That's sustainable, yeah, cleaning products, where instead of using single use plastics, where you're buying like Windex and 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, Paiju 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.
Invested in coming called Chill House. Oh, I invested in Liquid Death. Been drinking it.
SPEAKER_01
What has been the most lucrative angel investment you've made?
SPEAKER_00
I mean, none of them have returned anything yet. But I think first dibs is probably, they've gone on to raise several rounds. The iconic investment has, there was like Black Line and Alibaba and a bunch of stuff I invested in back in like 2012, 2013.
And that stuff 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 pay those capital gains with that shit in the bank.
It's just cash for now. And then I still have like, I had a lot in my house, which is just stupid. I'm just over exposed in real estate, but I live here, it's awesome.
And then I have- Are you in LA? I'm a bunch in like Morgan Stanley now. Manages that stuff. I'm in LA, I'm up in the hills.
SPEAKER_02
It's really pretty. Nice. And you've done a whole bunch of stuff and I feel like 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've hiked up this mountain and you're like, wow, okay, I see a whole bunch of other possibilities now. What's like, I don't know, not like a 10 year plan, but like, what are you see yourself doing going forward? Like, are you gonna start more businesses?
SPEAKER_00
Do you, what do you wanna 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 an 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 kind of like heal all my scars from nasty gal by building something that feels better. But I didn't, you know, things, I put things into the world that just like have momentum and then that's my life.
Been 14 years since I founded nasty gal. 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 wrote a book alone and it became this like big thing. And then I'm like, I have to catch all the, I mean, of course we should all be, and I am so grateful that any thing I put out into the world, not anything, but like the things, some of the things I put out into the world just catch fire in that way. But that leads me to, in some ways, just being like befolded into the opportunity, which is like, oh, boo-hoo, right? It's like, I like just raise money again and 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, just like what you do is like what the business demands.
And I'm feeling like, in the future, I want to have more choices. Like, I, at some point, I want to just work on a smaller, I don't want to start a company, I'm from Ken. So there's that.
SPEAKER_01
Wait, wait, wait, you don't want to start a business again? No. You don't want to start a company or a business?
SPEAKER_02
It doesn't mean she won't, she just doesn't want to.
SPEAKER_00
I never want to raise money, issue equity, or like build a large team again.
SPEAKER_01
So do you have, what do you do now? I mean, are you working at Girl Boss?
SPEAKER_00
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 go through.
That's, I mean, we had something signed that was like four times last year's revenue. That would have been a one check for a year long deal. And that was signed on, you know, the CFO's desk for counter signature, and then back in COVID.
So this shit's really affected our business. I have a great operator, I have a great VP of finance. There's obviously a tension 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? No investor's 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 standups, 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 when our future's uncertain is like, you know, that it's natural and human just be like, oh shit, what is this mean for me? You know, and the fact is I'll be fine.
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.
SPEAKER_01
Can I ask you a question about Girl Boss's business model? 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.
SPEAKER_00
That would be an initial idea. So venture is interesting, right? You take advice and it was built. There's a paywall that we already built that we were going to launch with and then.
SPEAKER_02
That would be a great business. But she's pointing out it's not a venture scale business.
SPEAKER_01
I just so disagree with that.
SPEAKER_00
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, 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, we've never seen work before. And so the media business, which is what we started out with, all of our revenues has been from brand partnerships outside of ticket sales for the conference. 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 Bison, everything else with binary, like everything, those guys took all the money and then the world changed and we 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, to whatever's happening with brands and, you know, media world.
So I wanted to build the community that we had offline, online because it was just so massive and so special and to be able to connect the women from all the countries that flew in for the rally, who paid to put themselves up, who paid for a conference ticket to give them the opportunity to connect with one another and to bring our community online is a really special thing. And, you know, there's people who couldn't afford 30 bucks a month. So it felt good to bring something truly democratic forward, but it wasn't a great business decision.
It hasn't, I mean, obviously it hasn't generated revenue for us, but it's something I'm incredibly proud of.
SPEAKER_01
Yeah, I hear everything you're saying. It's, you're kind of putting it 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.
SPEAKER_00
Yeah, we were going to build an app this year and that's just kind of on hold. So we were going to growing it.
SPEAKER_01
You, 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, 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?
SPEAKER_00
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, they're, they're raising, they have a lead. The lead got in touch with me and I'm just not sure about it, but I think sustainability, I think, I mean, I'm not super deep on FinTech, but there's another company called Main Street that's super fascinating who are raising, who, I don't know how to describe it, but usually like government incentives are just this super like okay 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 you're, I don't know, whatever your payroll system is and with you directly to just basically, they save like on average companies, they work with like $30,000 a year, I think. And so they're kind of like your central hub for those kind of government incentives and just navigating that world, which is often just very challenging for small businesses.
SPEAKER_01
I'm looking at it now, this is awesome.
SPEAKER_00
Yeah, it's cool. Yeah, I like it.
SPEAKER_02
It's just like my thing 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 or I want to talk to people who know about this. Is there anything that's got your curiosity?
SPEAKER_00
I mean, I'm kind of interested in people who build personal brands because it's just like super weird, but I think it's something like I should be doing more of, but like I don't need the house and I don't know what I'm supposed to post about. I just like the lean startup, like good degree. Like I just fucking donated all of those books because I'm like, I've never raised a 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 of Red is 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.
SPEAKER_01
I'm in the similar boat with you. I've been reading a lot of fiction, just like American classics like Catcher and the Ride, 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.
And 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 started Maxin Magazine. He also started Micro Warehouse, which was a large publicly traded company. 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 tile, but bear with me.
SPEAKER_02
It's, yeah, you just can't tell her the title. The description was great, but as soon as you say, if you had said the title up front,
SPEAKER_01
I don't, I try not to tell 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? It's horribly titled, but I know.
SPEAKER_00
It's like offensive or something,
SPEAKER_02
but it's like, he, it's, it's exactly what you're saying. You're not interested in these like sort of business books.
SPEAKER_01
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.
Interesting. And he like tells funny stories about, 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, in almost like a fiction way.
SPEAKER_00
Yeah. I have to commit to actually read. I'm like, I just came through books, like I let them like, I just let the scent walk up.
And I'm like, cool, I get it. Like I get enough of it. I don't need to finish this book.
And honestly, like buying books is like enough of a statement about like, oh, this matters to me. Like, I know it's like spending money, but it's just like, oh, this, it just like solidifies something that's important to you. Like I'm, I'm going to pay certain amount of attention to this, even if it's buying a book that says I'm able to show.
SPEAKER_01
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.
And you're like, oh, this looks awesome. This like, I come back with a massive bag.
SPEAKER_00
I do that with magazines and just like, not talking about me anymore. Bam. Bam. Get it.
SPEAKER_01
Sean, is there anything else you want to go over?
SPEAKER_02
No, this has been good. I gotta 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.
SPEAKER_00
And it's like, you know, I care too much. My biggest weakness is that I want to fly. I care too much.
SPEAKER_02
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 we had this conversation.
SPEAKER_00
Well, me too. I'm around, feel free to reach out. I think you have my email.
If you, I think you do. But yeah, this has been blast.