Latest / Giant Ideas / Girlboss and Nasty Gal Founder, Sophia Amoruso: The Post GirlBoss Era

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Girlboss and Nasty Gal Founder, Sophia Amoruso: The Post GirlBoss Era · Giant Ideas

• 0:00
  SPEAKER_00: I tanked a company.
• 0:01
  SPEAKER_00: Maybe I wasn't the girl boss.
• 0:03
  SPEAKER_00: You know, I was a fraud.
• 0:05
  SPEAKER_00: And there were headlines like, Does the failure of Nasty Gail mean millennials aren't ready to lead?
• 0:09
  SPEAKER_00: And I was like, oh my god.
• 0:10
  SPEAKER_00: The public sees me as the example of millennial leadership.
• 0:15
  SPEAKER_01: Hello, and welcome to Giant Ideas with me, Cameron McLean, and me, Tommy Stadlin.
• 0:20
  SPEAKER_03: We're co-founders of Giant Ventures, which builds and backs purpose-driven companies.
• 0:24
  SPEAKER_01: At Giant, we're lucky to meet extraordinary people with giant ideas that are changing the world.
• 0:29
  SPEAKER_01: This podcast brings you behind-the-scenes access to those ideas and the inspiring stories of the people behind them.
• 0:35
  SPEAKER_03: We explore how one giant idea can kickstart a billion-dollar company, shape culture, and transform life as we know it.
• 1:02
  SPEAKER_03: She lived the Girlboss dream herself, turning a humble eBay store that she started at age 22 into a company with hundreds of millions of dollars in revenue by the age of just 29.
• 1:12
  SPEAKER_03: She was on the cover of Forbes as one of the richest self-made women in the world.
• 1:16
  SPEAKER_03: But later that same year in 2016, Nasty Girl would file for bankruptcy.
• 1:20
  SPEAKER_03: They've been unable to see a capital or a buyer as the gap between growth and profitability widened.
• 1:25
  SPEAKER_03: Not deterred by Nasty Girl's bankruptcy, Amaruzo applied her lessons and founded Girlboss Media, a digital media brand and community aimed at empowering female entrepreneurs.
• 1:35
  SPEAKER_03: She's since put her hand to new pursuits, from her mentorship business to her latest focus, Trust Fund, an early stage mentor fund focused on pre-seed and seed stage investing.
• 1:45
  SPEAKER_03: Today we talk about everything from the death of the Girl Boss to why female founders are treated differently in business.
• 1:56
  SPEAKER_03: Sophia, welcome to the show.
• 1:57
  SPEAKER_00: Thanks for having me.
• 1:58
  SPEAKER_03: Let's start at the beginning.
• 1:59
  SPEAKER_03: Both of your parents, as I understand it, never worked for a salary.
• 2:02
  SPEAKER_03: They were kind of worked for a commission.
• 2:04
  SPEAKER_03: And that seems to have been from what I've read, like a kind of culture in your family, that you've got to go out there and hustle and kind of make make your money by hustling.
• 2:12
  SPEAKER_03: Is that right?
• 2:13
  SPEAKER_03: And do you think that is a big part of why you became an entrepreneur?
• 2:16
  SPEAKER_00: Yeah, I think it is right.
• 2:17
  SPEAKER_00: I don't my parents weren't like, wow, you should be an entrepreneur.
• 2:20
  SPEAKER_00: We really think you should start a business.
• 2:22
  SPEAKER_00: And neither of my parents necessarily started businesses.
• 2:25
  SPEAKER_00: You know, my mom sold homes for a builder, and my dad did loans and worked with like new home developers and stuff like that.
• 2:33
  SPEAKER_00: Um, but they never worked for a salary.
• 2:35
  SPEAKER_00: And, you know, there were ups and downs financially in my family.
• 2:39
  SPEAKER_00: My dad's dad owned a motel that he grew up on with like seven of you know, the kids.
• 2:46
  SPEAKER_00: So um he comes from a really, I don't know, kind of like you have to pull yourself up by your bootstraps kind of uh environment, even though he never quote unquote bootstrapped a business.
• 2:57
  SPEAKER_00: And I think, you know, for me, I never really belonged, I guess.
• 3:03
  SPEAKER_00: There was no career path that I was really drawn to.
• 3:06
  SPEAKER_00: Nobody really explained to me what a career was.
• 3:09
  SPEAKER_00: And that was definitely a disadvantage when I started employing people because I had no idea what they needed to be successful.
• 3:15
  SPEAKER_00: Um, and just kind of landed in entrepreneurship very much accidentally trying to avoid working for other people or working, period, and then I became a CEO, and the rest is history that I guess we'll talk about.
• 3:28
  SPEAKER_03: So it's interesting that that does seem to be a common pattern amongst very successful entrepreneurs like you of school years just really grating against the idea of these rules which seem so arbitrary, often applied by people who you may not feel uh should be in charge of you.
• 3:46
  SPEAKER_00: Yeah.
• 3:47
  SPEAKER_03: Let's fast forward a little bit to your later teenage years, early 20s.
• 3:51
  SPEAKER_03: Reading up on you, it sounds like you had all sorts of wild adventures and got yourself into all sorts of scrapes.
• 3:57
  SPEAKER_03: Tell us about them.
• 3:57
  SPEAKER_03: Tell us about the the fun as a late teenage year person and what lessons you learned from all of that.
• 4:03
  SPEAKER_00: Totally.
• 4:04
  SPEAKER_00: I mean, I hated high school.
• 4:05
  SPEAKER_00: And so I homeschooled in the later years of high school and actually moved out when I was 17 before I got my diploma, moved into a closet for$60 a month.
• 4:17
  SPEAKER_03: A closet, a real closet?
• 4:18
  SPEAKER_00: Yeah, yes, like under some stairs.
• 4:20
  SPEAKER_00: Like you couldn't stand up in it.
• 4:22
  SPEAKER_00: But I put like a sleeping bag down and I got like a carpet remnant and cut like cut it to fit.
• 4:29
  SPEAKER_00: I think actually it it like you know did this.
• 4:31
  SPEAKER_00: It wasn't like perfectly cut.
• 4:33
  SPEAKER_00: You literally slept in a closet.
• 4:34
  SPEAKER_00: Yeah.
• 4:35
  SPEAKER_00: Wow.
• 4:36
  SPEAKER_00: Yeah.
• 4:37
  SPEAKER_00: I was, you know, I didn't really want things.
• 4:40
  SPEAKER_00: You know, it wasn't until I guess I could afford things that I wanted things or had any taste level, or I'm not really sure.
• 4:48
  SPEAKER_00: Um, but that's where I, you know, went at the end of high school.
• 4:51
  SPEAKER_00: My parents had divorced when I was 17, and my mom moved to Oakland, and my dad was like figuring it out in our family home, and it's just not a happy place.
• 5:00
  SPEAKER_00: So I did that, and then I moved to Olympia, Washington.
• 5:04
  SPEAKER_00: I was just very, I was still angsty, very much like an anti-capitalist.
• 5:09
  SPEAKER_00: I like in high school, I went to the anarchist book fair in San Francisco every year.
• 5:13
  SPEAKER_00: Why?
• 5:13
  SPEAKER_03: Why why were you anti-capitalist?
• 5:14
  SPEAKER_00: Because I didn't, I just didn't want to be a quote unquote quote wage slave.
• 5:19
  SPEAKER_00: I didn't want to spend my whole, you know, I thought that work was, you know, submitting to the nine to five and then having these like whiffs of freedom, you know, between, you know, on weekends and that you spend most of your life working.
• 5:32
  SPEAKER_00: I've spent most of my life working now, which wasn't my goal, but I've aligned, you know, naturally kind of like aligned the things that I'm curious about and it got me very far because I was interested in them.
• 5:44
  SPEAKER_00: And, you know, there's times it felt like work and times it didn't feel like work.
• 5:48
  SPEAKER_00: Um, so I moved to Olympia, Washington, did a bunch of like goofy hitchhiking, like up and down the West Coast in like big rigs, so those huge trucks and had a lot of fun, but at a certain point I felt felt like, you know, I'm gonna age out of this.
• 6:03
  SPEAKER_00: I was just like, I got caught stealing, actually.
• 6:06
  SPEAKER_00: Oh what?
• 6:06
  SPEAKER_00: I was oh yeah, yeah.
• 6:08
  SPEAKER_00: And so that was when I was like, you know, yeah, I was like, I don't want to, I want to be in control of my life.
• 6:15
  SPEAKER_00: And if I'm doing things that break the law, I'm actually doing the opposite of what I want.
• 6:21
  SPEAKER_00: So it wasn't like I'm gonna go play the game now, but it was just like I'm gonna go get a solid job at a photo lab and a record store and then a shoe store.
• 6:30
  SPEAKER_00: I didn't know there were careers beyond like retail.
• 6:32
  SPEAKER_00: And I thought that people worked in business were like corporate slaves and um squares, and they all carried briefcases and just like and that's just like a very simplistic view, but I had never, you know, seen what it's like to really be in a workplace.
• 6:50
  SPEAKER_00: And then I was 22 and again still like working these goofy hourly jobs, and my last job was in the lobby of an art school, um, checking student IDs.
• 7:02
  SPEAKER_00: And so the job was just sitting there, and if someone walked in, I'd say, like, hey, can you sign in?
• 7:07
  SPEAKER_00: Can I see your ID?
• 7:08
  SPEAKER_00: And I'd be like, Admissions is on the second floor.
• 7:11
  SPEAKER_00: And that was it.
• 7:12
  SPEAKER_00: That was the entirety of the job.
• 7:14
  SPEAKER_00: But I had a computer.
• 7:16
  SPEAKER_00: I was on MySpace at the time, and I started getting friend requests from eBay sellers who were selling vintage and using MySpace, and you know, had a profile and you know, each week like announced new listings, you know, you could publish that kind of stuff on MySpace and you know, went and clicked through.
• 7:35
  SPEAKER_00: I wore entirely vintage at the time.
• 7:37
  SPEAKER_00: I just liked it more for whatever reason.
• 7:39
  SPEAKER_03: My jacket's vintage, you know, and that you bought offline or online?
• 7:43
  SPEAKER_00: Back then I bought it all offline.
• 7:45
  SPEAKER_00: You know, there wasn't a ton of online shopping.
• 7:47
  SPEAKER_00: There were there was eBay, the marketplace, and then there weren't a lot of like small businesses opening, you know, e-comm shops selling vintage or clothes.
• 7:56
  SPEAKER_00: It was very much like big retailers, you know, eBay, Etsy didn't exist.
• 8:01
  SPEAKER_00: So this is in 2006.
• 8:04
  SPEAKER_00: It was like, oh wow, these auctions are going crazy.
• 8:07
  SPEAKER_00: You know, it wasn't like, you know, place and offer kind of eBay business.
• 8:12
  SPEAKER_00: I don't even know if that was there at the time.
• 8:14
  SPEAKER_00: It was auctions only, and they would start the prices at$9.99, which seemed, I mean, I could buy things for less than that.
• 8:21
  SPEAKER_02: Okay.
• 8:21
  SPEAKER_00: But, you know, a girl in Copenhagen, a girl in Australia, you know, maybe the dollar's strong in, you know, some European country.
• 8:30
  SPEAKER_00: And for them, it's a lot cheaper to buy it from the US.
• 8:32
  SPEAKER_00: And, you know, the auctions just like went crazy.
• 8:35
  SPEAKER_00: And the prices I saw were like way beyond what I'd ever seen vintage go for.
• 8:40
  SPEAKER_00: And I was like, cool.
• 8:42
  SPEAKER_00: I've got, I had like the Dome IMAC.
• 8:45
  SPEAKER_02: Yes.
• 8:45
  SPEAKER_00: And um, you know, got some vintage together and like created my account and named it Nasty Gal Vintage and put my first listings up and they didn't sell right away, you know.
• 9:00
  SPEAKER_03: It took me a while to learn what people wanted, and that's you know, like a whole nother story, but and you're doing this from the job where you're checking people's ID and you're like sitting there on the side selling the stuff on eBay?
• 9:11
  SPEAKER_00: No, I actually quit that I got that job because I needed health insurance.
• 9:15
  SPEAKER_03: Okay.
• 9:16
  SPEAKER_00: And in the US at the time, if you had a pre-existing condition, I had a hernia, you couldn't get individual health insurance.
• 9:25
  SPEAKER_00: The only way to get it would be group health insurance.
• 9:28
  SPEAKER_00: And so I got the job at this like pretty corporate art school in San Francisco.
• 9:33
  SPEAKER_00: You know, had to wait three months for my insurance benefits to kick kick in.
• 9:37
  SPEAKER_00: Uh, got my hernia fixed, got my surgery done, and you know, paid$50 to Kaiser or something.
• 9:43
  SPEAKER_00: And then was like, I don't know what's next, and you know, was kind of bouncing, like living with my boyfriend at the time, and then was like, let me let me see if I can make a few bucks on eBay so I don't have to work for other people.
• 9:56
  SPEAKER_00: And that was it.
• 9:57
  SPEAKER_00: I was just trying to evade work.
• 9:58
  SPEAKER_03: How quickly did it start to really work?
• 10:02
  SPEAKER_00: I mean, I'd say I learned a lot just watching other sellers.
• 10:06
  SPEAKER_00: I didn't do exactly what they did, but it's not hard to reverse engineer something as simple as selling things on eBay and seeing what works and what people are bidding on.
• 10:15
  SPEAKER_00: So I'd say like probably a few months before I started, wasn't exploding yet, but I was like, okay, this is solid.
• 10:23
  SPEAKER_00: And, you know, my customers came back and you know, I'd see the same name and you know, address of someone who had won an auction and you know, started growing the my MySpace audience for Nasty Gal Vintage.
• 10:37
  SPEAKER_00: And this was, you know, before Facebook ads and you know what it what they've built, you know, their entire business on.
• 10:47
  SPEAKER_00: But I had this bot that I had this like illegal bot that I downloaded somewhere.
• 10:53
  SPEAKER_00: And at the time, like, you know, you could scrape people's MySpace profiles.
• 10:59
  SPEAKER_00: They were, you know, all of that data was just whatever, like HTML on the web.
• 11:04
  SPEAKER_00: It wasn't like something like Instagram.
• 11:06
  SPEAKER_00: And I would type in their user ID number on this bot, like say it's like a magazine, like a cool fashion magazine that I know my customers followed.
• 11:14
  SPEAKER_00: I could type that user ID in and then even drill down as far as ages, countries, like and then who they who they were friends with.
• 11:25
  SPEAKER_00: And so I was able to do like really targeted marketing, and the thing would sit there and add friends.
• 11:31
  SPEAKER_00: And every like 10 or so, I would have to sit there and enter a captcha code to prove I was human.
• 11:36
  SPEAKER_00: And then it would add like another 10 friends, and I would just sit there for hours having this bot add really qualified people on MySpace.
• 11:46
  SPEAKER_00: And I don't know if I had like 30,000 or 60,000 friends or whatever they were called on MySpace by the time I left.
• 11:53
  SPEAKER_00: But MySpace was a really big engine for Nasty Gal.
• 11:58
  SPEAKER_03: Um and that kind of approach to growth hacking, presumably, was something that no one else running an eBay store was doing.
• 12:05
  SPEAKER_03: Probably not.
• 12:06
  SPEAKER_03: And w how do you reckon you were someone who figured that out?
• 12:10
  SPEAKER_03: What was it about you that did something like that?
• 12:12
  SPEAKER_03: But then also the brand that you created was just kind of like fire compared to a lot of because the rest of the sites back then who were doing something similar were all quite kind of uh not very exciting, put a little like that.
• 12:24
  SPEAKER_00: Yeah, I mean they would sell stuff that people loved, but it was all very kind of hippy-dippy vintage, and I I would call myself a punk, um, maybe still, but at that time my references were just really different.
• 12:39
  SPEAKER_00: You know, I was into, you know, this woman, Betty Betty Davis, who has, you know, made incredible funk music, and she was, you know, married to Miles Davis for a while and allegedly like too wild for him, and her lyrics were, you know, really edgy.
• 12:54
  SPEAKER_00: And so I named Nasty Gal after an album of hers and also song on that album.
• 12:59
  SPEAKER_00: But I was like, I'm just gonna do it differently.
• 13:01
  SPEAKER_00: And it could have either been, you know, it wasn't it could have been like ew, but it was it was sticky.
• 13:08
  SPEAKER_00: And I think, you know, my mom's my mom writes a lot and gets paid for it.
• 13:15
  SPEAKER_00: Later in her career, really started doing that and wrote for the new local newspaper.
• 13:19
  SPEAKER_00: And so I think words have always been really important to me, and naturally just kind of became a copywriter who, you know, the way I wrote things, whether it's the eBay listing or the description of the product or you know, that week's update, um, and or like my, you know, MySpace profile.
• 13:40
  SPEAKER_00: What what didn't really exist that exists now, and there's agencies that do it all day long, is like a brand that feels like a human, like your friend is talking to you.
• 13:50
  SPEAKER_00: And what I created with Nasty Gal, I don't know how, was, you know, this this kind of world that a woman could see herself kind of stepping into and being like one degree ahead of where she was, like slightly cooler, slightly more sophisticated, slightly more stylish, but not to the extent that I'm alienating her.
• 14:14
  SPEAKER_00: And so, you know, I didn't just dump clothes on a model, I styled it, and she had a handbag and sometimes sunglasses, and she was like, there was movement, she was going somewhere.
• 14:23
  SPEAKER_00: I wasn't a photographer, I wasn't a trained copywriter, I wasn't a trained merchant.
• 14:29
  SPEAKER_00: You know, there was none of those things, you know, were anything that I had learned formally, but just you know, presented it the way I would have wanted to see it.
• 14:42
  SPEAKER_00: And just kept iterating, right?
• 14:45
  SPEAKER_00: Like I was not in a place where someone handed me a business, like a venture capitalist, um, and said, like, okay, like here you go, here's some training wheels, like go iterate, but you might run out of money.
• 14:58
  SPEAKER_00: Like, there was no, there was no way for me to, I couldn't run out of money, you know.
• 15:03
  SPEAKER_00: I didn't have a lot of overhead, but I was like, if I'm gonna do this, I have to sell things that people want.
• 15:09
  SPEAKER_00: And sometimes there were things that I would never wear.
• 15:12
  SPEAKER_02: Okay.
• 15:12
  SPEAKER_00: You know, it wasn't about my style.
• 15:15
  SPEAKER_00: You know, I, you know, imbued everything with a personality that was very much mine and very much a brand, but it was never like about me because the whole idea is that you're selling things that people want to buy, and there was no, you know, backstop for me had I tried to do something that didn't that people didn't want.
• 15:35
  SPEAKER_00: Like that's it.
• 15:36
  SPEAKER_00: You create something that people want and you keep listening, do a better job.
• 15:40
  SPEAKER_00: Yeah.
• 15:41
  SPEAKER_00: And you find product market fit, which I guess I did, you know.
• 15:43
  SPEAKER_03: Yeah.
• 15:44
  SPEAKER_03: And the name comes from this very inspiring, empowered, punk woman.
• 15:49
  SPEAKER_03: And, you know, this kind of, I guess, very cool but ultimately feminist vibe going on there.
• 15:55
  SPEAKER_03: Was that something do you think which really resonated with the customers, or was it more just, you know, you you you you created something very cool, or was there an element of like people were buying this stuff because they bought into that philosophy?
• 16:06
  SPEAKER_00: Yeah, no, they absolutely bought into it.
• 16:08
  SPEAKER_00: Like Nasty Gal was a feeling.
• 16:10
  SPEAKER_00: Like if you bought a motorcycle jacket from Nasty Gal, it was emotional.
• 16:13
  SPEAKER_00: It was like this is a promise to my more confident self.
• 16:16
  SPEAKER_00: It was way more, you know, than a jacket.
• 16:20
  SPEAKER_00: And if an order was late or we shipped the wrong thing, it was like your best friend had, you know, betrayed you.
• 16:29
  SPEAKER_00: It was the level of excitement of getting a package from Nasty Gao was you know beyond, I think, almost any brand that it was it was a phenomenon.
• 16:39
  SPEAKER_00: Um, and that was really cool, you know, and it um I think by its own nature, just kind of being there showed people a level of confidence and uniqueness, individuality, permission to be themselves in a way that hadn't existed in the same way, at least online.
• 17:03
  SPEAKER_03: Um was that a big motivator for you?
• 17:05
  SPEAKER_03: What was your purpose?
• 17:06
  SPEAKER_03: Was it that?
• 17:06
  SPEAKER_03: Was it getting a real kick out of that empowerment?
• 17:09
  SPEAKER_03: Was it money?
• 17:10
  SPEAKER_03: What was driving you on to make this happen?
• 17:13
  SPEAKER_00: It was money.
• 17:14
  SPEAKER_00: Not like I wasn't making a ton in the beginning, but it was just like I cannot work for other people.
• 17:18
  SPEAKER_00: And it was like, this is fun.
• 17:19
  SPEAKER_00: Oh my gosh.
• 17:20
  SPEAKER_00: It was the first time in my life where if I did a better job, the results were better.
• 17:26
  SPEAKER_00: Like you work in a lobby, I was like, I'm not, I don't want to be promoted.
• 17:30
  SPEAKER_00: I don't want to manage people.
• 17:31
  SPEAKER_00: I don't even know what that means.
• 17:32
  SPEAKER_00: You work in a record store, it's like, wow, I'm gonna be the best clerk in this record store.
• 17:37
  SPEAKER_00: Like if I did a better, if I did a better job alphabetizing and filing things and putting a whatever sticker on it when it came in, the result wasn't different.
• 17:46
  SPEAKER_00: So I did kind of bare minimum in the hourly jobs that I had, but it was the first time I'd applied like my talent or intellect or curiosity in a way where, okay, I watch, adapt.
• 17:59
  SPEAKER_00: Oh my gosh, this auction went higher, or you know, there's more people bidding on it, or whatever it is, you know?
• 18:06
  SPEAKER_00: And so that was just really gratifying.
• 18:09
  SPEAKER_03: Give us a sense of how quickly that happened.
• 18:10
  SPEAKER_03: How quickly did it give us an idea of some of the numbers and scale of speed of this thing.
• 18:14
  SPEAKER_00: Yeah.
• 18:15
  SPEAKER_00: So the first year, uh Nasty Gal did I think 75k in revenue.
• 18:19
  SPEAKER_03: Okay.
• 18:19
  SPEAKER_00: And it was just me.
• 18:20
  SPEAKER_00: But I didn't spend it.
• 18:21
  SPEAKER_00: I didn't, I mean, I just ate burritos and like Starbucks chai.
• 18:26
  SPEAKER_00: I didn't, I didn't want anything.
• 18:28
  SPEAKER_00: I had like an 87 Volvo and was just spending my time in thrift stores and at estate sales.
• 18:34
  SPEAKER_00: So I guess I kept the money in the business.
• 18:37
  SPEAKER_00: And the second year was 250k.
• 18:40
  SPEAKER_00: The next year was 1.1, and then it was six and a half.
• 18:43
  SPEAKER_00: And then I think it was like 12 and then 28.
• 18:46
  SPEAKER_00: I have the original deck that I presented to Index in 2012.
• 18:50
  SPEAKER_03: Index Ventures, you became the first venture investor, first outside investor in this business.
• 18:54
  SPEAKER_00: Yeah.
• 18:54
  SPEAKER_00: And so started Nastigal probably December, November, December of 2006.
• 19:01
  SPEAKER_00: And by 2012, I had raised$50 million on a$350 million post-money valuation.
• 19:08
  SPEAKER_03: Wow.
• 19:08
  SPEAKER_03: And before that happened, the the revenue numbers are just surging.
• 19:11
  SPEAKER_03: At that point, are you feeling like you've won?
• 19:14
  SPEAKER_03: Are you feeling giddy from the just incredible success of what you've built, which is extraordinary from nothing?
• 19:20
  SPEAKER_00: I think so, but I just I hadn't had a lot of recognition for it.
• 19:23
  SPEAKER_00: I was just doing my job.
• 19:25
  SPEAKER_00: Um Was it strange to you?
• 19:27
  SPEAKER_03: Was it kind of, you know, having been checking these ID cards a very short time later, you're running this business which was turning over$28 million?
• 19:33
  SPEAKER_00: Yeah.
• 19:34
  SPEAKER_00: I mean, I was clueless.
• 19:35
  SPEAKER_00: I started hiring people.
• 19:38
  SPEAKER_00: I mean, before I had raised money, I had a COO for a little while.
• 19:41
  SPEAKER_00: I'd hire an HR person.
• 19:43
  SPEAKER_00: There's no gusto or just works.
• 19:46
  SPEAKER_00: You know, it was like, you know, everything was very manual and rubbing two sticks together.
• 19:51
  SPEAKER_00: And I know had to hire a guy to process returns and someone to ship things.
• 19:56
  SPEAKER_00: And I had done all those things.
• 19:58
  SPEAKER_00: So it made it a lot easier.
• 19:59
  SPEAKER_00: I think when I started hiring people, at least for the essential things to get the job done at the time, I was able to train people on my voice and customer service.
• 20:08
  SPEAKER_00: You know, hi, of course, not sure.
• 20:11
  SPEAKER_00: You know, don't call it sparkly, call it glitter.
• 20:14
  SPEAKER_00: I don't know, just stuff like that that I remember, you know, sitting with people who eventually wrote product descriptions or answered customer service inquiries, um, or shipped stuff and like here's how you slap a label on it.
• 20:25
  SPEAKER_00: Whatever it was, I had already done it, which made that easy to kind of hand over to other people.
• 20:31
  SPEAKER_00: I think the styling, photography, editing of the photography, and yeah, that and and buying, like curation was something that I held on to v for a long time.
• 20:43
  SPEAKER_00: Like that was the thing that I was had was in most in the weeds of for the longest time until I hired like a creative director or something.
• 20:51
  SPEAKER_00: I think I was really excited about it, but I just didn't, I don't think I had much perspective.
• 20:55
  SPEAKER_00: And I was like, you know, it was definitely holy shit.
• 20:58
  SPEAKER_00: You know, I remember in, you know, one holiday season uh we were doing in like a day what we were doing the month a year prior.
• 21:08
  SPEAKER_00: These are all like kids in their 20s that are, you know, shipping stuff, and we're all doing like, you know, manual, pretty basic work.
• 21:16
  SPEAKER_00: I remember being like, okay, if we hit these numbers, we're gonna get a bounce house and put it in here.
• 21:22
  SPEAKER_00: And it was like this.
• 21:23
  SPEAKER_00: A bouncy castle.
• 21:24
  SPEAKER_00: Yeah, but it was an upside-down horse.
• 21:27
  SPEAKER_00: So when you jumped in it, the horse legs kind of like moved around and the head like bobbed.
• 21:33
  SPEAKER_00: It was I think I might have a photo of it somewhere, but that was, you know, so they'd ship packages and then go jump in the bounce house and rented it.
• 21:40
  SPEAKER_00: Phenomenal wasn't there forever, but that was my idea of like a company park.
• 21:45
  SPEAKER_03: Amazing.
• 21:46
  SPEAKER_00: Yeah.
• 21:46
  SPEAKER_03: It sounds like you were having great fun.
• 21:48
  SPEAKER_00: It was really fun.
• 21:49
  SPEAKER_00: It was the most fun.
• 21:50
  SPEAKER_00: Yeah.
• 21:51
  SPEAKER_00: I mean, I got to buy a all the vintage, I didn't keep any of it for myself because I my job was to sell it.
• 21:58
  SPEAKER_03: Yes.
• 21:58
  SPEAKER_03: Don't get high on your own supply.
• 22:00
  SPEAKER_00: Exactly.
• 22:01
  SPEAKER_03: What were you most proud of with Nasty Girl?
• 22:03
  SPEAKER_00: I think uh the way it influenced women and their level of confidence.
• 22:09
  SPEAKER_00: I wasn't like, wow, I'm gonna create a feminist brand.
• 22:12
  SPEAKER_00: But you know, I think um being yourself, which I was being, gives other people permission to be themselves.
• 22:20
  SPEAKER_00: There was a CMO, who's like the CMO at Patagonia, I think, that said to me a long time ago that the best brands give people permission to be themselves.
• 22:30
  SPEAKER_00: Um, and a lot of women identified plus plus with Nasty Gown and were like, wow, you know, I could see myself being as cool as that model.
• 22:41
  SPEAKER_00: She's not too pretty.
• 22:42
  SPEAKER_00: She's pretty, but she's friendly, you know, and she's done like alien luxury kind of, you know, runway model.
• 22:48
  SPEAKER_00: So there's a lot of things where, you know, I met the customers where they were and then challenged them enough for it to feel aspirational.
• 22:58
  SPEAKER_03: I want to come back and talk in depth about the effect on women of both Nasty Girl and Girl Boss.
• 23:03
  SPEAKER_03: But you mentioned their uh index ventures and venture capital.
• 23:07
  SPEAKER_03: And so that feels like a kind of cru couple of crucial moments where they came in, um, invested at a very high valuation, you were profitable before, then you get kind of flooded with venture capital money, and not long afterwards things take a turn for for the worse.
• 23:22
  SPEAKER_03: I guess they also I've I've heard advised you not to sell the business for$400 million.
• 23:27
  SPEAKER_00: Yeah.
• 23:27
  SPEAKER_03: Um so two kind of pivotal moments.
• 23:29
  SPEAKER_03: You're a venture investor now.
• 23:31
  SPEAKER_03: I I obviously uh co-founded giant, a venture firm.
• 23:34
  SPEAKER_03: So we I I assume both believe that venture capital can be a real force for good.
• 23:38
  SPEAKER_03: Yeah.
• 23:38
  SPEAKER_03: But it but it's not right for every business.
• 23:40
  SPEAKER_03: And how do you look back at the involvement of venture capsule with your business?
• 23:45
  SPEAKER_00: I mean, it completely changed the business like overnight.
• 23:48
  SPEAKER_00: I no one had ever set expectations for my business before.
• 23:52
  SPEAKER_00: I hadn't really set expectations.
• 23:53
  SPEAKER_00: It was like, yeah, cool, we'll hit this number, but I was just knocking out of the park.
• 23:57
  SPEAKER_00: I didn't even know how fast it would grow.
• 24:00
  SPEAKER_00: And I was just trying to keep up with demand.
• 24:02
  SPEAKER_00: So it wasn't like, great, we're gonna hire 50 people and accelerate growth and invest in this.
• 24:07
  SPEAKER_00: It was like, oh shit, stuff's selling out.
• 24:09
  SPEAKER_00: Let me go buy more of it.
• 24:11
  SPEAKER_00: And it kept selling.
• 24:12
  SPEAKER_00: It was pretty simple, just buy things that people want, sell them for more than you paid for them, and don't spend all the money.
• 24:18
  SPEAKER_00: That's how you build a profitable business.
• 24:20
  SPEAKER_00: That was literally all I knew.
• 24:22
  SPEAKER_00: And index came in, yeah, and plowed 50 million into it.
• 24:25
  SPEAKER_00: I took some money off the table.
• 24:27
  SPEAKER_00: So the first money in was out of a growth fund.
• 24:29
  SPEAKER_02: Okay.
• 24:30
  SPEAKER_00: And at that point, it was like I owned 80% of it after I raised$50 million, which was kind of wild.
• 24:37
  SPEAKER_00: So on paper, I was like worth a lot of money, but again, I didn't even, I don't know.
• 24:40
  SPEAKER_00: It was it changed my life very, very materially.
• 24:44
  SPEAKER_00: Um, I think I was like I was like 27 or 20.
• 24:47
  SPEAKER_00: 27.
• 24:48
  SPEAKER_00: Yeah.
• 24:48
  SPEAKER_00: Wow.
• 24:49
  SPEAKER_03: And on and on paper at that point, you're worth like 300 million dollars.
• 24:52
  SPEAKER_03: Like 280 or something.
• 24:54
  SPEAKER_00: And then, you know, the expectation, you know, I brought in like a whole suite of C-level executives and a chief people officer and a CTO.
• 25:03
  SPEAKER_00: Like, there was no Shopify.
• 25:04
  SPEAKER_00: Like we had to build our e-comm site in like Cold Fusion.
• 25:08
  SPEAKER_00: I'm not a, you know, an engineer, but it was like at that time, it was even like ancient technology.
• 25:14
  SPEAKER_00: Um, had to have a whole product team to just build a regular shopping app.
• 25:18
  SPEAKER_00: It was, it became a really expensive enterprise.
• 25:22
  SPEAKER_00: And, you know, I remember sitting at a table with Danny Reimer and the COO I had hired at the time.
• 25:31
  SPEAKER_00: And it was like, okay, we're doing 28 million this year.
• 25:34
  SPEAKER_00: Did like, I don't know if it was six or twelve or it could have been more.
• 25:38
  SPEAKER_00: I the deck I looked at that I presented them was actually the growth was bigger than I've feel like I've been saying on podcasts for a long time.
• 25:46
  SPEAKER_00: It's just like also triple error.
• 25:47
  SPEAKER_02: Yeah.
• 25:48
  SPEAKER_00: Um, and so we rounded up by 100 million.
• 25:50
  SPEAKER_00: I was like, these are like grown-ups that have built business, you know, Danny had hadn't built a business, but he's seen, you know, insides of enough businesses to where I was like, okay, these people know what they're doing.
• 26:01
  SPEAKER_00: And, you know, of of course he does.
• 26:04
  SPEAKER_03: And he was your investor up there.
• 26:05
  SPEAKER_00: Yeah, he was my investor.
• 26:06
  SPEAKER_00: I had one board member.
• 26:08
  unknown: Okay.
• 26:08
  SPEAKER_00: I had two seats and he had one, and the other one of my seats was empty almost until the end.
• 26:13
  SPEAKER_02: Yeah.
• 26:14
  SPEAKER_00: Which wasn't a good choice.
• 26:15
  SPEAKER_02: Okay.
• 26:16
  SPEAKER_00: But we sat there and rounded up by a hundred million.
• 26:18
  SPEAKER_00: And then your full cost?
• 26:20
  SPEAKER_00: Yeah.
• 26:21
  SPEAKER_03: Okay.
• 26:21
  SPEAKER_00: Just round, just that was it like based on, I don't know, explosive growth.
• 26:26
  SPEAKER_00: But and then it was like, okay, well, to do that, we need to hire, I don't know, a hundred people.
• 26:32
  SPEAKER_00: Um, and I was really ill-equipped to run a to hire a hundred people.
• 26:38
  SPEAKER_00: Right.
• 26:38
  SPEAKER_00: And, you know, to build processes.
• 26:40
  SPEAKER_00: And, you know, it just became this kind of like, you know, tower of babel cluster of, you know, people showing up and duplication of efforts and people bumping into eat one another.
• 26:51
  SPEAKER_00: And it was just not something I was like able to manage.
• 26:55
  SPEAKER_00: It was a really good recruiter, and everybody wanted to work for Nasty Gal.
• 26:59
  SPEAKER_00: I can imagine that.
• 27:00
  SPEAKER_00: Um, but it was a major step change, and that's usually a good word.
• 27:05
  SPEAKER_02: Right.
• 27:06
  SPEAKER_00: Um, in the business and the expectations of me as like a CEO and a leader, and I have to get up and inspire people.
• 27:13
  SPEAKER_00: Like, I'm an introvert, like I have a personality, but it's not my nature to get up and like rah-rah.
• 27:19
  SPEAKER_00: Like I cannot put on a smile unless I actually think something is funny.
• 27:23
  SPEAKER_02: Yeah.
• 27:24
  SPEAKER_00: Um, so I had no idea what leadership was.
• 27:28
  SPEAKER_00: Like I kind of understood management, but people needed to be told what to do, inspired to do it, and then told what to do, even C-level executives.
• 27:39
  SPEAKER_00: And then I had to make sure that they actually were doing it.
• 27:43
  SPEAKER_00: And I was like, I'm sorry.
• 27:44
  SPEAKER_00: You know, these people have had careers for longer than I've been alive, some of them.
• 27:48
  SPEAKER_00: You know, 25-year veterans, whatever.
• 27:51
  SPEAKER_00: And I thought they'd show up and diagnose the business and all work together and, you know, figure out a plan and, you know, grow the thing because they had, you know, built other companies and built teams before.
• 28:04
  SPEAKER_00: And that wasn't necessarily the case.
• 28:07
  SPEAKER_00: I didn't always check in and make, okay, well, you said this is going to be two months.
• 28:11
  SPEAKER_00: And it's like, this person's paid like a few hundred grand a year.
• 28:14
  SPEAKER_00: Just do what you say you're gonna do.
• 28:16
  SPEAKER_00: I show up and do what I say I'm gonna do.
• 28:19
  SPEAKER_00: I do what I think the business needs, and I don't have any other choice.
• 28:24
  SPEAKER_00: But I had never, you know, been an employee and I had no example of what leadership looked like, so I had absolutely no, I guess I want to say empathy's tough.
• 28:34
  SPEAKER_00: Like I can't say I didn't have empathy.
• 28:36
  SPEAKER_00: I don't know what the word is, but I had no playbook for what my job had very quickly become.
• 28:42
  SPEAKER_03: Did you feel at the time like you were losing control?
• 28:46
  SPEAKER_00: No, which is probably the problem.
• 28:49
  unknown: Okay.
• 28:50
  SPEAKER_00: Yeah.
• 28:51
  SPEAKER_00: I mean, I didn't really see under the hood until late, you know, later on.
• 28:56
  SPEAKER_03: How do you look back now at the decision not to sell the business for$400 million and the advice you got around that?
• 29:01
  SPEAKER_00: Urban outfitters um isn't historically acquisitive.
• 29:07
  SPEAKER_02: Okay.
• 29:07
  SPEAKER_00: And I think whatever the deal would have been, I think integrating the company into their, I mean, family business really, um, would have been really challenging.
• 29:19
  SPEAKER_00: And I 99% of deals just don't get done anyway.
• 29:22
  SPEAKER_00: Okay.
• 29:23
  SPEAKER_00: So I, you know, I don't want to be like, wow, a hundred percent that would have happened and God, I regret it so much.
• 29:30
  SPEAKER_00: It's an example of me taking advice from people who I would say are greedier than I am and have LPs to answer to and would rather lose the money than mark it down or just hold it at cost.
• 29:41
  SPEAKER_00: Like I didn't know, I didn't know they had bosses and they had to go put on a, you know, you know, aver you know, annual kind of AGM for their investors and be like, rah, rah, look, you know, if they had had to mark nasty gal down or sell it at cost, it wouldn't have looked good, but holding it at cost is not not so bad.
• 30:04
  SPEAKER_00: Um and so, you know, I didn't know for a long time that, you know, as much as supportive as my investors were, our interests just were not aligned.
• 30:18
  SPEAKER_00: And that's something that is um, I think an important thing to talk about and important thing for founders to understand, um, because I learned that the hard way.
• 30:28
  SPEAKER_00: Um, and like I said, I didn't have a board because I had heard from other people that boards are just pissing contests and people disagreeing and people having egos.
• 30:39
  SPEAKER_00: And so I was like, I don't want to deal with that.
• 30:41
  SPEAKER_00: But had I had other voices around the table, advisors, you know, other investors, because I raised from Index and Thrive.
• 30:49
  SPEAKER_00: I think Thrive put in a million.
• 30:51
  SPEAKER_00: Okay.
• 30:51
  SPEAKER_00: It's like Josh Kushner and Will Gabrick with like crackly voices.
• 30:54
  SPEAKER_00: They were like kids.
• 30:55
  SPEAKER_00: And I was like, who gave you this money?
• 30:57
  SPEAKER_00: This is crazy.
• 30:59
  SPEAKER_00: Um, you know, had I had more like former operators around, or maybe had I raised money from an a former operator, I think it would have been really different.
• 31:08
  SPEAKER_03: Agreed.
• 31:09
  SPEAKER_03: So 2016, you've built this incredible business.
• 31:12
  SPEAKER_03: It's starting to go perhaps a little bit wrong, but the outside world doesn't know that.
• 31:16
  SPEAKER_03: You've written this incredible best-selling book, Girl Boss, which has been then turned into a Netflix show.
• 31:21
  SPEAKER_03: You've sh the show has been shot.
• 31:23
  SPEAKER_03: You're the hero of the show.
• 31:25
  SPEAKER_03: And just before it comes out, things start to really fall apart in the business.
• 31:29
  SPEAKER_03: Tell us about that year and what it was like living through it.
• 31:32
  SPEAKER_00: Yeah.
• 31:33
  SPEAKER_00: So 2016, I would say, is the hardest year of my life.
• 31:37
  SPEAKER_00: Um, we had had some layoffs in 2015.
• 31:40
  SPEAKER_00: It was not the best.
• 31:42
  SPEAKER_00: I wrote the book at the beginning of, it was published at the beginning of 2014.
• 31:47
  SPEAKER_00: Right.
• 31:47
  SPEAKER_00: So it's been 11 years, which is wild.
• 31:50
  SPEAKER_00: And, you know, we had had some layoffs in 2015.
• 31:55
  SPEAKER_00: Open a couple stores, you know, try to go offline.
• 31:59
  SPEAKER_00: And at the beginning of 20, I had hired a CEO for the last two years.
• 32:06
  SPEAKER_00: I was like, I don't like this job.
• 32:07
  SPEAKER_00: I want to do the creative stuff.
• 32:08
  SPEAKER_00: So I had moved into just the chairman role, but was still very involved.
• 32:13
  SPEAKER_00: At the same time, the success of the book was something that was, it was just like a runaway success.
• 32:18
  SPEAKER_00: And Girl Boss, the book, the philosophy, the word, the hashtag, uh, the movement that people called it was almost louder than Nasty Gal, which was like the business that I had built to over 100 million in revenue, by the way.
• 32:32
  SPEAKER_00: I think that's probably important to mention.
• 32:35
  SPEAKER_00: Um and eventually kind of ran out of it.
• 32:39
  SPEAKER_00: But it became harder to fund the business because, you know, like I said, similar to the acquisition offer I'd gotten, it was in my investor's best interest not to, you know, take a haircut or do a down round and just say, like, all right, figure it out, figure it out.
• 32:58
  SPEAKER_00: We, you know, took on some venture debt and just kind of kicked something that didn't have to be inevitable, but the inevitable down the road.
• 33:10
  SPEAKER_00: Is that what you say?
• 33:11
  SPEAKER_02: Right.
• 33:11
  SPEAKER_00: Um, colloquialisms are different here.
• 33:13
  SPEAKER_00: So I'm gonna start like my American colloquialisms are gonna start atrophying.
• 33:17
  SPEAKER_03: We'll try to do that.
• 33:18
  SPEAKER_00: I'm gonna say things like uh I can't be arsed.
• 33:21
  SPEAKER_03: Like, what?
• 33:22
  SPEAKER_03: You've only been here a month.
• 33:23
  SPEAKER_03: You're a quick learner.
• 33:24
  SPEAKER_00: I know, I'm dating an English man, so there's that.
• 33:26
  SPEAKER_00: Very good.
• 33:27
  SPEAKER_00: And so in, you know, things were already tough.
• 33:30
  SPEAKER_00: There had been headlines about toxic culture, you know, we'd had layoffs.
• 33:34
  SPEAKER_03: Was that toxic culture?
• 33:36
  SPEAKER_00: Probably.
• 33:38
  SPEAKER_00: Um, I don't think I was toxic.
• 33:40
  SPEAKER_00: I think I didn't give people a chance, so I would just like fire them and be like, that's not okay, you should know better.
• 33:46
  SPEAKER_02: Okay.
• 33:46
  SPEAKER_00: Um, so I think I would have been a better leader had I helped people like get there or given them opportunities to improve.
• 33:56
  SPEAKER_00: But I would have had to know what they don't know to do that, and I didn't know what they needed to do to, you know, to a certain extent.
• 34:05
  SPEAKER_00: So, you know, that's hard.
• 34:06
  SPEAKER_00: But every founder experiences that.
• 34:08
  SPEAKER_00: I just think some founders are probably better than others at it.
• 34:11
  SPEAKER_00: Um, and yeah, I mean, you lay off the PR team and they're gonna, they it's their job to yap.
• 34:18
  SPEAKER_00: Right.
• 34:19
  SPEAKER_00: So not not that I don't take responsibility for, you know, everything that happened in the company.
• 34:26
  SPEAKER_00: The fact is that the CEO knows 10% of what's happening in their company.
• 34:31
  SPEAKER_00: Sure.
• 34:31
  SPEAKER_00: There's just, I don't know what boss is being a dick to some junior employee.
• 34:36
  SPEAKER_00: I don't know who's saying weird shit.
• 34:38
  SPEAKER_00: Yeah.
• 34:38
  SPEAKER_00: You know, you know, and people in a room saying things like that's not on brand.
• 34:43
  SPEAKER_00: And, you know, other employers like feel bad about themselves, and there's like, you know, it was a fashion company, and I wasn't clicky, but you know, people working at Nasty Al was very cool.
• 34:54
  SPEAKER_00: Right.
• 34:55
  SPEAKER_00: And, you know, there were people who thought very highly of themselves because they were there and they were in positions of power, and you know, I think that can just get really ugly.
• 35:05
  SPEAKER_00: It's you know, it's the companies that people have a lot of affinity for that you see in the headlines when things don't go right.
• 35:12
  SPEAKER_00: It's it's there where, you know, there's this schism between the utopia the employees think that, you know, they've signed on for because, you know, they're working at this cool company, but actually it's like any other company, and you can only employ people when there's b the business to support it.
• 35:28
  SPEAKER_00: But it was similar to a customer getting, you know, an order late and being like, oh my God, you know, it was like a personal assault on somebody who was who's removed from the company because you know, they identified so much with being a part of Nasty Gal and the culture, which is what you want, but it's also, you know, if you get fired from Verizon, you know, or I don't know, Thames Water, like I don't think you're gonna be like, oh my god, I'm not part of this thing that you know, when I went out to a bar and I said I worked at Nasty Gal, people thought I was cooler.
• 36:01
  SPEAKER_00: Like, so laid people off, whatever, not whatever.
• 36:05
  SPEAKER_00: But um, in 2016, I'd gotten married in 2015.
• 36:10
  SPEAKER_02: Okay.
• 36:10
  SPEAKER_00: To someone I had dated for like four years before that and actually met when I was 19.
• 36:15
  SPEAKER_00: And by 2016, um, in in I think June of 2016, I was on the cover of Forbes.
• 36:22
  SPEAKER_00: Um, they said I was richer than Beyoncé um on paper.
• 36:28
  SPEAKER_00: Uh and by July, my husband of like a year-ish, was like, see ya.
• 36:36
  SPEAKER_00: And I was like, what?
• 36:37
  SPEAKER_00: Like, he didn't even like argue.
• 36:39
  SPEAKER_00: Can you at least argue before we get there?
• 36:41
  SPEAKER_00: It was just like, you know, a big surprise.
• 36:44
  SPEAKER_00: And I had a solid prenup, so whatever.
• 36:47
  SPEAKER_00: He got like 50 grand in a Volvo.
• 36:49
  SPEAKER_00: Loser.
• 36:50
  SPEAKER_00: Um, he didn't work for like the last like three years, you know, he had like my credit card.
• 36:55
  SPEAKER_00: It's like whatever.
• 36:56
  SPEAKER_00: I was like, I'm a generous person.
• 36:58
  SPEAKER_00: I'm just like, you know, if it was like some dude that had made a bunch of money and his girlfriend was working for 50 grand a year, he'd probably just be like, listen, like you I don't even get to see you because you're grinding away at this job.
• 37:11
  SPEAKER_00: So maybe that would have been normal.
• 37:13
  SPEAKER_00: But and I tried to just do what seemed normal, like we're building a life together kind of thing.
• 37:18
  SPEAKER_00: But I don't know how that works the other way around.
• 37:21
  SPEAKER_00: Anyway, so by July he had like bounced.
• 37:24
  SPEAKER_00: By November, Nasty Gal had filed for chapter 11.
• 37:29
  SPEAKER_02: Okay.
• 37:29
  SPEAKER_00: And so it was a series of potential acquisitions.
• 37:33
  SPEAKER_00: We did do a down round, you know, Ron Johnson from like Apple, JC Penny came in and, you know, tried to fix things and brought his cronies in, and you know, was like, We're yes, we're gonna s you know, have this strategic acquisition.
• 37:49
  SPEAKER_00: And I just remember walking up to one of like one of his guys and saying, What's the chance this happens?
• 37:55
  SPEAKER_00: And his answer was a hundred percent.
• 37:57
  SPEAKER_00: And that's where I was just like, Oh fuck.
• 37:59
  SPEAKER_00: Like, I know that's not like if you don't know that that is very unlikely to be true, then I'm really scared for the future.
• 38:09
  SPEAKER_00: And at that point, I was just so far in over my head to a certain extent I had checked out.
• 38:15
  SPEAKER_00: And we could have re-capitalized the business, you know, after bankruptcy, we could have like you know, started again.
• 38:24
  SPEAKER_00: But I was like, I did this for 10 years, I'm not gonna start the thing.
• 38:27
  SPEAKER_00: I already started.
• 38:28
  SPEAKER_00: Um, and it was like the first point where I was like, I'm gonna be selfish about this.
• 38:32
  SPEAKER_00: And when we did file for chapter 11, it was like, I have to say, like a little bit of a relief because when you raise 50 million dollars, it's really hard to quit, and it's uh with a brand like Nasty Galls really hard to be fired.
• 38:46
  SPEAKER_00: So I was like, oh my god, I'm out.
• 38:49
  SPEAKER_00: It was devastating, but it was also like a big exhale at the same time.
• 38:55
  SPEAKER_03: And at the same time as all this is happening, you are literally all over the wild on Netflix.
• 39:00
  SPEAKER_03: Or your character is.
• 39:01
  SPEAKER_03: Yes, you're the hero of the show.
• 39:03
  SPEAKER_00: November, the company files for chapter 11 while this show is being made called Girl Boss about who I was when I was 22 years old, starting an eBay store in San Francisco.
• 39:13
  SPEAKER_00: Four months later, five months later, I think in April of 2017, Netflix, you know, releases a show called Girlboss, streams it into 130 million homes in 195 countries in almost every language.
• 39:32
  SPEAKER_00: And I, this was four months after, you know, Trump had just been elected.
• 39:36
  SPEAKER_00: Hillary had lost, like the whole conversation around women had totally changed.
• 39:40
  SPEAKER_00: Things became way more political.
• 39:43
  SPEAKER_00: Um, and it was just like a goofy kind of scripted comedy.
• 39:48
  SPEAKER_00: But it was, you know, oh like a girl.
• 39:52
  SPEAKER_00: Why would we need to be called girl bosses?
• 39:54
  SPEAKER_00: I'm just a boss, you know.
• 39:55
  SPEAKER_00: It just was like, it was just the name of a book.
• 39:58
  SPEAKER_00: Like, you know, it it it and the timing was just bad because then I was like, you know, I tanked a company, but maybe I wasn't the girl boss.
• 40:09
  SPEAKER_00: You know, I was a fraud.
• 40:11
  SPEAKER_00: And there were headlines like, does the failure of Nasty Gail mean millennials aren't ready to lead?
• 40:15
  SPEAKER_00: And I was like, Oh my god, like the public sees me as the example of millennial leadership.
• 40:22
  SPEAKER_00: I didn't even know that that's was the case.
• 40:26
  SPEAKER_00: And so it was really devastating.
• 40:29
  SPEAKER_00: The hardest part was when the Netflix series came out because there's this huge the public just really conflated the character, what happened on the show.
• 40:38
  SPEAKER_00: She was kind of abrasive, you know, things, you know, they wrote stuff into the show that like didn't actually happen.
• 40:44
  SPEAKER_00: I thought it was like kind of a cute show, like outside of depicting me.
• 40:48
  SPEAKER_00: I didn't have influence over the script or how I was depicted.
• 40:51
  SPEAKER_00: I was like, here's some vintage, don't make her look lame and get that band poster off the wall in her bedroom.
• 40:57
  SPEAKER_00: That was that's like the that was the extent of my influence.
• 41:00
  SPEAKER_00: Um, and so there's this like huge conflation between like Sophia the leader, the girl boss that we loved, like someone responsible for a lot of employees and a lot of you know money, and this character that, you know, had been totally made up, and it's like which one of those is she?
• 41:18
  SPEAKER_00: And so it wasn't really any of that, I wasn't any of them.
• 41:23
  SPEAKER_00: Because I'm a complex person that's like nobody, nobody who could no stranger who writes something about me could ever know.
• 41:31
  SPEAKER_00: Um so that was that was really, really hard.
• 41:35
  SPEAKER_03: Were you treated differently as a female founder who failed compared to how a man would be treated?
• 41:41
  SPEAKER_00: Yeah.
• 41:42
  SPEAKER_03: In what way?
• 41:43
  SPEAKER_00: I mean, there's just no I mean, if you look at the history, I mean, of women, you know, there's so there's so few of us leading.
• 41:53
  SPEAKER_00: And if you look at just like across the board institutionally, like the disparity like between men and women historically, and like we've just kind of always been way behind and also in the workplace, and so there's few of us, and there's few of us to point to.
• 42:10
  SPEAKER_00: And I was the example, the poster child of female millennial leadership.
• 42:16
  SPEAKER_00: And um and so the my megaphone was big, there was a lot more eyes on me.
• 42:22
  SPEAKER_00: But um, I think in most areas of life and the way people are perceived and women are treated, it's all very much based on other people's perception of our identity, whether that's your religion or your gender or your color.
• 42:41
  SPEAKER_00: It's like you're walking into the room with some privilege, you know, there's you know, I think it's there's a whole whatever intersectionality and ranking of those things.
• 42:50
  SPEAKER_00: But there's no way that I couldn't have been, because that's just the way the world works.
• 42:54
  SPEAKER_00: It's not even like specific to business.
• 42:57
  SPEAKER_03: There was a lot of over-intellectualization about um about girl boss, right?
• 43:02
  SPEAKER_03: So it was like, well, it it shouldn't be people said it should be women boss, not girl boss, right?
• 43:07
  SPEAKER_03: Why they call girls not women?
• 43:09
  SPEAKER_03: People said there shouldn't be as you said, there shouldn't be girl boss, it should just be boss.
• 43:13
  SPEAKER_03: And yeah, lots of intellectualizing about it.
• 43:16
  SPEAKER_03: How do you feel about some of that criticism?
• 43:18
  SPEAKER_00: It was a pink book.
• 43:20
  SPEAKER_00: It was a pink book that was like, go get him, you know, it was it was I I was in my twenties.
• 43:27
  SPEAKER_00: It was a book that was simple.
• 43:31
  SPEAKER_00: Um, some of it was maybe even like naive.
• 43:34
  SPEAKER_00: I had written it when everything was going great.
• 43:38
  SPEAKER_00: So uh, you know, I think it would have been different had I experienced more adversity in the business before I wrote it.
• 43:46
  SPEAKER_00: Um, but the book had kicked off, you know, this amazing, you know, I'm a girl boss, right?
• 43:52
  SPEAKER_00: I built two businesses where people said I'm a nasty gal and I'm a girl boss.
• 43:57
  SPEAKER_00: Like I don't think it gets any higher as far as the brand.
• 44:00
  SPEAKER_00: Goes to have people actually start, you know, put I am in front of the name your brand, right?
• 44:05
  SPEAKER_03: Amazing.
• 44:05
  SPEAKER_00: Yeah, it was amazing.
• 44:06
  SPEAKER_00: I think it became this, I mean, it entered the zeitgeist uh in a way that was completely out of my control.
• 44:14
  SPEAKER_00: And again, you can only hope that the things you create have that kind of impact.
• 44:20
  SPEAKER_00: Um, but at a certain point it no longer became mine.
• 44:24
  SPEAKER_00: And people kind of used it as a shorthand for, you know, sometimes really great, like, I'm a girl boss.
• 44:33
  SPEAKER_00: And then sometimes, like, you know, oh, girl boss is kind of this oversimplification of female capitalism and whatever, and it's just like, I don't know, I wrote a pink book, and you know, that was my experience, and why am I responsible for all women?
• 44:49
  SPEAKER_00: And you know, people were you know asking me to talk about the wage gap, and it's like, I don't know, I never experienced that because I never like had a job in an office.
• 44:59
  SPEAKER_00: It was weird, um, but also it was just no longer mine in a way that is really cool.
• 45:05
  SPEAKER_00: Um that what you create becomes this um, you know, again, shorthand for something, even if it's politicized or uh overintellectualized, um that you know, people can use to um have an important conversation.
• 45:25
  SPEAKER_00: And I do think there are a lot of important conversations that where the word girl boss was used, but I also think um people are really giddy about taking down women, and I think that was part of it where it was like, you know, and there's the the 2020 kind of like slaughter of every female founder, and I don't know if you like were witness to that, but that was like the end of the girl boss is a good thing, like there's you know, just so many headlines, and it's like Glossier is toxic, and you know, away is toxic, and the founders of Refinery29 are awful, and the founder of Ref Reformation's racist, and you know, it's like the the wing completely went under, right?
• 46:10
  SPEAKER_00: A women's co-working space.
• 46:11
  SPEAKER_00: And so I think like I said, um, you know, people work for companies.
• 46:16
  SPEAKER_00: If a company stands for something, you know, they expect the company to cure things that exist everywhere and permeate all parts of society, you know, just because a woman founds a brand and tries to do good for women doesn't mean that things that, you know, exist everywhere aren't going to sneak into the company and affect the employees.
• 46:41
  SPEAKER_00: But there's like this expectation that it's gonna be this place that just, you know, heals all disparity and everyone's gonna have like a great experience, and you know, those kinds of things aren't going to exist.
• 46:52
  SPEAKER_00: And I think when you stand for something, and I don't know if this has happened with you because you make, you know, you invest in impact-focused businesses, there will be people who say, like, well, that's not good, you know, EVs have batteries that are bad, or whatever.
• 47:08
  SPEAKER_00: People will poke holes in anything you try to do that's good.
• 47:12
  SPEAKER_00: And I think that was like a you know, that's a big part of why that happened.
• 47:17
  SPEAKER_03: Talking about female founders, do you, do I have a responsibility to proactively go out there and try to back as many strong female founders as possible, or is it more about just making sure the process is fair and not trying to, you know, impact the number of women who come through the door?
• 47:34
  SPEAKER_03: How do you feel about that in terms of our responsibility as investors?
• 47:37
  SPEAKER_00: I think it's a nuanced like question or answer because you know, I see less female founded companies.
• 47:49
  SPEAKER_00: Um, there are less of them.
• 47:52
  SPEAKER_00: There's also less second-time female founders.
• 47:56
  SPEAKER_00: Um, so if you know five or ten years ago, you know, there were way less female founders, like the guys who built those companies have built shops that as someone who's going to give someone money to build a business, something that makes you feel more comfortable sometimes.
• 48:12
  SPEAKER_00: Doesn't always mean that they're great at what they did and maybe they failed, um, but they have some experience.
• 48:19
  SPEAKER_00: Um, that's something I I mean I like second-time founders because I did so much, you know, I was such a better leader in my second company.
• 48:28
  SPEAKER_00: I was a clueless first-time founder.
• 48:31
  SPEAKER_00: I also see a lot of female founded businesses that are consumer businesses, and I don't invest in consumer.
• 48:38
  SPEAKER_00: So that makes it harder.
• 48:41
  SPEAKER_00: Um, you know, there's it feels like there's you know a lot more women who want to start brands, and you know, m my hist my background is in consumer and brands, but that's not what I want to spend the second half of my career doing because I blew it in the first half of my career.
• 48:59
  SPEAKER_00: And I also don't think that consumer, most consumer businesses are venture backable or can have venture-sized outcomes.
• 49:08
  SPEAKER_00: Um, yes, I have responsibility, but I can do a better job.
• 49:12
  SPEAKER_00: But like if you look at my portfolio, there aren't enough female founders.
• 49:16
  SPEAKER_00: Um and I think that's just by the nature of like the deals I've seen and what I've found conviction for.
• 49:27
  SPEAKER_00: And it's my job as someone who's investing other people's money to optimize for that um over I think giving people a shot.
• 49:41
  SPEAKER_00: It's not angel money, like it's venture money.
• 49:44
  SPEAKER_00: And um, I have bosses, and my job is ultimately to make money for them.
• 49:50
  SPEAKER_03: We've backed at least one company together.
• 49:52
  SPEAKER_00: Yeah.
• 49:53
  SPEAKER_03: Tell me and the listeners about what you look for in entrepreneurs now that you are a venture investor.
• 49:58
  SPEAKER_00: I look for founders that have domain expertise who have, you know, spent time in companies that are solving similar problems or problems that are parallel in some way, or founders who have experienced the problem that they are trying to solve personally, um, and have, you know, again, like empathy for the end user and just understand the problem on a cellular level.
• 50:26
  SPEAKER_00: I like second-time founders.
• 50:29
  SPEAKER_00: I like founders who aren't egotistical.
• 50:32
  SPEAKER_00: Like you get on the phone with some of these really confident guys, and sometimes they like build companies, but it's just the way they talk is sometimes so entitled and just like cringy.
• 50:48
  SPEAKER_00: It doesn't happen a lot, but I definitely avoid the people that seem overconfident.
• 50:54
  SPEAKER_00: I think being a zealot is different than being overconfident.
• 50:58
  SPEAKER_02: Yeah.
• 50:59
  SPEAKER_00: So I want to hire zealots who are like committed to building the thing, who I think can lead and get people behind them.
• 51:07
  SPEAKER_00: You know, if you're investing money in a in a founder, you also need to know that they're gonna be able to go raise subsequent rounds, or ideally maybe they, you know, become profitable.
• 51:18
  SPEAKER_00: But if they do want to or um raise subsequent rounds, there has to be some talent that they can go pitch people and raise money.
• 51:26
  SPEAKER_00: You know, so you I also have to believe that they can keep doing other things as a founder that aren't in relation to the product they're building or aren't even in relation to leadership.
• 51:34
  SPEAKER_00: Like that's a whole nother part of what comes with building a venture-backed business.
• 51:38
  SPEAKER_03: We could go on forever, but we have time for one more question, which is we we ask all of our guests this.
• 51:43
  SPEAKER_03: What is it about you that has created all of the enormous success which we've just talked about?
• 51:49
  SPEAKER_00: I think it's that I'm a really curious person and I thrive in environments that I don't technically belong in.
• 51:57
  SPEAKER_00: And I found a way to make imposter some syndrome something that works in my favor because when I hear or feel that I don't belong, it actually means that I'm just doing something different and I have a different perspective, and I'm brave enough to bring that to the table, and it tends to cut through the noise.
• 52:17
  SPEAKER_00: So I think for anybody who's you know afraid to do that, it's important to know that that can also be your superpower.
• 52:28
  SPEAKER_00: It's not that hard, you just be yourself.
• 52:30
  SPEAKER_00: It's like I'm just lazy.
• 52:33
  SPEAKER_03: Very powerful.
• 52:34
  SPEAKER_03: Sophia, thank you so much for sharing your giant idea.
• 52:36
  SPEAKER_00: Thanks for having me.
• 52:37
  SPEAKER_03: Appreciate it.
• 52:37
  SPEAKER_03: If you like the episode, don't forget to like, subscribe, and follow the show, and you can find many more giant ideas wherever you get your podcasts.