The End of Human Trafficking May Begin with Radical Empathy - Julia Flynn Siler

In 19th Century San Francisco's Chinatown only 1 in 10 people were women, and most of them were forced into prostitution, trafficked by criminal tongs. In today’s episode, meet the Scottish sewing instructor Donaldina Cameron and the women she collaborated with and helped escape from sex slavery between 1870 and 1930. This week on Inflection Point: Julia Flynn Siler talks about her new book The White Devil’s Daughters: The Women Who Fought Slavery in San Francisco’s Chinatown. Prepare yourself for bomb scares and bubonic plague quarantines, court cases and crowdfunding efforts. Join us in what is, ultimately, a conversation about standing up to a broken society, and how women can help women rise up.

Recorded at the Bay Area Book Festival in May 2019 as part of their Women Lit programming.

Photo courtesy of Julia Flynn Siler

Photo courtesy of Julia Flynn Siler

“Put down your male fragility”: Scene On Radio’s John Biewen & Celeste Headlee on how men can help fight patriarchy

What’s going on with men? Why is it so hard to negotiate the gender power dynamic in everyday situations, like work meetings? Can masculinity exist without its more toxic forms? And why can men get away with sexual misconduct---and even end up seeming like the “real” victim when they’re accused?

While I’ve taken this season of Inflection Point to focus on what women can do to rise up and have more power, John Biewen and Celeste Headlee of Scene on Radio - MEN have been examining how the patriarchy that we’re rising up against was formed in the first place--and what to do about it.

Today we’re taking a look at the conversations we’ve had over the past seasons of both shows and comparing notes to see if we can find some answers---together.

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Stitch Fix Founder Katrina Lake gives the C-Suite a Makeover

At age 35, Stitch Fix founder Katrina Lake became the youngest female founder and CEO to take a company public in 2017. Stitch Fix is now worth over two billion dollars. She has not only changed the way many of us shop for clothes, but she’s also changing how we think about leaders. Find out she learned to embrace her history-making role as the youngest woman to take a startup to IPO.
 

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TRANSCRIPT

Katrina Lake:                       " I was almost like prickly about being a female CEO in the early days and I think it was at a time when you would see companies like Dropbox and AirBNB and whatever else and I was like, I just want to be a CEO and I don't need to be a female CEO, and I don't need to be the female CEO. "

Lauren Schiller:                  Meet Katrina Lake. If you've got a Facebook feed there's a good chance you've come across her online personal styling company, StitchFix. If you haven't come across this phenomenon it's like having a personal clothing stylist pick out clothes for you, ship them to your house and not complain when you send anything back. At age 35, in 2017, Katrina became the youngest female founder and CEO to take a company public. Stitchfix is now worth over $2 billion, and she got there by breaking the mold of what you might still typically think of when you think of leadership.

Katrina Lake:                       "I think a lot of the things that you think about as an entrepreneur, you think somebody who's like super risky and somebody who's going to stay up for all hours tinkering with something in their garage. Not that I didn't spend all hours doing StitchFix at some point, but you know, I don't think that I had like the typical traits of an entrepreneur. "

Lauren Schiller:                  Katrina has not only changed the way many of us shop with StitchFix, but she's also changing how we think about leaders. For one thing, you may have caught all the press hullaballoo over the picture of her from the Nasdaq IPO when she stood onstage with her young son on her hip unintentionally setting the tone for a new generation of women leaders. Her executive team is as close to a 50/50 gender split as you can get and now she plans to send a message intentionally about the importance of family leave because she's pregnant with her second child and is going to take a full 16-week maternity leave.

Katrina Lake:                       "I had to do the same research of trying to figure out who were the people before me that took a maternity leave when they were a public company CEO? Like, I mean, you can do the math. If I was the youngest female founder and I'm 35, you know, there's not going to be a lot of other examples out there of people who faced that, and so there's not a lot of precedent. So, somebody who now is raising young people and is thinking about like how the world that you see impacts who people become, there aren't great examples."

Lauren Schiller:                  I mean, if you want something done right, you have to do it yourself. Case in point, before starting her own company, Lake was convinced that someone somewhere would have developed a new vision for disrupting retail, but after meeting with hundreds of entrepreneurs she became convinced that the only way to find that company was to start it herself. I spoke with Katrina Lake onstage at Inforum at the Common Wealth Club to find out what makes her tick and how she turned this startup into a successful IPO.

 (LIVE CONVERSATION)

Lauren Schiller:                  I have to make a confession before we really get into it, which is that I had to change my clothes like 14 times before I got here.

Katrina Lake:                       I did too. It's okay.

Lauren Schiller:                  I don't know about all of you, but it was really hard to decide what to wear, especially when sitting down with a fashion entrepreneur such as yourself, but it made me start thinking about what the role of clothing is for women and men and the way that we thinks bout it and how it says who we are, and I'm curious what your thoughts are? Your entire business is around making sure that people are wearing stuff that they look good in and that they're comfortable in. How do you think about the role of clothing?

Katrina Lake:                       It was a major point of inspiration to me and I think two different angles. So, one, there are so few other categories where people really thoughtfully think about like oh, I'm coveting this and I want this and you think about something for weeks and you get inspired by it and I mean, there's so few other categories. Food is probably one of them also where you have the same emotional connection to it, but with clothing it's just one of these things that is so important in people's lives, and not in a materialistic way, but in this way that like you thoughtfully decide every day what you're going to put on your body and that means something. And, so, I think that made it very attractive to me because I think it's just this really interesting huge category that people weren't really thinking about what does technology bring to it and what's the next generation of it? I think the second element they're getting to a little bit is like it really does have an impact on who you are. I know this, and this was shared recently, but I'm now, I don't know, four or five months pregnant. I'm in that phase where you're like chubby but not pregnant yet.

Lauren Schiller:                  Nothing fits.

Lauren Schiller:                  Congratulations!

Katrina Lake:                       Nothing fits and it's such a good reminder of the humility of like how much I really appreciate when I have clothes that fit and when I know what I want to wear every day. The reality is if you're feeling great about who you are, if you're feeling confident about who you are, it really does impact all the touchpoints in your day. I think all of us know that feeling of when you're not quite feeling that way or the flip side is when you are and I think how electric that can be and I think in all these little micro moments in your day it can change your life of how kind you are to somebody, how kind you are to your kids, how outgoing you're going to be, how confident you are when you're at work doing something that's really important. For all those reasons I love that apparel was both super meaningful in people's lives and I think in these really small, but meaningful ways has an impact on people's lives every single day.

Lauren Schiller:                  What was happening in your life when you came up with the idea for StitchFix?

Katrina Lake:                       It's hard to say exactly when I came up with the idea, but I guess some history. Growing up as a ten-year-old, if you asked me what I wanted to be when I grew up I would have told you a doctor. It had never occurred to me that I should want to be an entrepreneur, I would be a good entrepreneur. You take all these, I forget what they're called, like a Myers-Briggs test. You take these tests when you're growing up and like zero of them told me I should be a entrepreneur. My mom was a public school teacher here in San Francisco for a long time. My dad was a doctor, but always in the university system. He was here at UCSF for probably over 20 years or so. There was not like an entrepreneurial bone in my body.

Katrina Lake:                       My journey was a little bit of an unconventional one where I worked at a consulting firm. I did that kind of out of indecision because I thought I wanted to be a doctor, but I wasn't ready to do that yet. I worked at a consulting firm and was lucky enough to kind of stumble into the retail and restaurant practice, and that is where both retail and restaurant I love because they're just these big meaningful categories.

Katrina Lake:                       The journey was more like I loved those categories and I was like, I want to work at whatever is going to be the future. I spent a bunch of time looking to join that company, and so I interviewed a bunch of places. I almost took a job at Starbucks. Ultimately, it didn't quite feel like that was exactly it and then I worked at a venture capital firm, thinking, okay, this is going to be a great way for me to meet the person who's going to create the future, so I went and met with 100 entrepreneurs in my two years there and didn't meet the person that I thought was going to be the future of retail, but got to meet 100 people who were all like pretty normal people who were not qualified to be an entrepreneur. I realized that any person could be this, and I think you get exposed to the Mark Zuckerberg and the Steve Jobs of the world and you don't have in your frame of reference that could be me. By meeting 100 people, you meet a lot of different types of people, so I realized I could do it. You know, I was really on this journey of I just want to work at whatever company is reinventing retail in the future and the formation of StitchFix was really just realizing that like, if I believe there is a different future out there, I could start it.

Lauren Schiller:                  Just create it. Just make your own future.

Katrina Lake:                       That was the beginning.

Lauren Schiller:                  Were you always a shopper? I mean, from an intellectual standpoint it was interesting to you, but in terms of your own personal, was that something that you either hated doing or loved doing?

Katrina Lake:                       Maybe both. I have a sister actually who's here. She's not the shopper either, but we have a sister who's the age in between us. She was a shopper and so she was the one who was definitely always the expert. She was the one taking the fashion risks. Natalie and I were probably more the followers in taking her hand me downs. What I still loved, and what I think even people who hate shopping can resonate with is there is nothing better than being able to feel like you have clothes in your closet that you love and there is nothing better than putting on an outfit and being like, this is a great look. Like, there is nothing better than that feeling. I really loved that and I loved the ways that clothing could contribute to that.

Katrina Lake:                       My middle sister literally will like, she would spend her free time looking at like the new arrivals on websites and that's not really how I spend my free time.

Lauren Schiller:                  Now you just have a company that has a combination of machines and people doing that for you.

Katrina Lake:                       Right. Well, and I think that's part of the inspiration too is there are people who love doing this and who are experts and know everything and in their free time love to do this, and wouldn't it be great to be able to create a job for people like that. That actually ended up being part of the inspiration too.

Lauren Schiller:                  How important was going to business school and creating this idea?

Katrina Lake:                       For me it was important because I wasn't this super risky entrepreneur type. I was never going to quit my reasonably well-paying job and have a gap on my resume. That was not something I was comfortable doing. For me, it was important because it created this two-year period of time where I could take this risk. I went to business school and my plan was to have a company off the ground, paying myself a salary, paying back my student loans the day I graduated, and if I wasn't able to have a business idea that was good enough that someone was going to give me money, if I wasn't able to have an idea that I wanted to do so that I would want to spend so far seven plus years on, then the worst case scenario is well, I have this MBA and I can go work at a great company. So, I saw it as kind of a risk-reduced way to start a company. For me, it was really important because I have a hard time imagining how else I would have been able to find kind of a two-year time period like that.

Katrina Lake:                       You know, I think that there's a network element that's somewhat valuable. The classes were great. It's so fun. I think, kind of like, probably the reason many of you are in this room, like getting to be an adult and go and learn is just like a really fun experience and getting to choose what you're going to learn. I definitely valued the experience, but the time was actually the part, I think, that was most valuable to me.

Lauren Schiller:                  Well, I'd love to talk a little bit more about this idea of risk because, you mentioned this a few minutes ago, that people have this idea in their head that entrepreneurs are these massive risk takers and anything goes. In fact, I saw a book just earlier today that said, How to Raise An Entrepreneur. It was like, teach them to take risks, like all these things that just go counter to what the actual common wisdom is about how you start a successful business, which is not necessarily to just let it all fly. Can you talk about your mentality around that and what you've run up against in terms of the perception of what an entrepreneur should be?

Katrina Lake:                       First of all, I think I am a good leader and a good CEO. I don't know necessarily that I was a great entrepreneur, to be honest, and, you know, maybe people think of, I mean, I don't know. Like, I just, it wasn't kind of where my comfort zone was. I don't sit back. You'll meet some founders who get to this stage of the company and they year the scrappy phases again and they like the building part. You'll hear that from people. I did like it, and it was really fun and crazy, but I don't know that that's the part that I feel like I thrive in, and we'll probably talk about this later, but you can also argue that I wasn't good at it. We've built a $2 billion company using $40 million of capital, not because I was like, I want to raise as little money as possible. It was because I could not raise more than that much money. In today's world a good entrepreneur is one that can raise the most money and hire the most people and buy the most time. You could argue I wasn't good at those things and ultimately was actually good at creating a company, which is maybe different.

Katrina Lake:                       I hope to be able to be a role model of a different type of entrepreneur because I think there are lots of women and men out there that might be thinking to themselves, that's not for me. I can't see myself being that crazy out-there person, and I felt the same way and I think ultimately like I actually think I'm good at this job and I don't know that I would have discovered it had it not been for kind of the convoluted path that I took.

Lauren Schiller:                  When you talk about StitchFix, I've heard it talked about as a fashion company, a technology company, the intersection of fashion and technology, what is it?

Katrina Lake:                       I mean, it is both. My theory on the whole thing is I think the world is, we are going to a place where like being a technology company will be table stakes for you to exist. You know, the idea of a tech company doesn't make a lot of sense to me. Like, I think Facebook is a marketing company, Uber is a transportation company, AirBNB is a hospitality company and we sell clothes. That is our business model. I think the reality is if you want to be around ten years from now,if you want to be successful ten years from now, all of us are going to have to be technology companies. Technology is certainly what is differentiated about stitchfix. I think what is very special about StitchFix, that at the end of the day the business that we're in is retail apparel. Actually, I just heard that on the analyst side, the investor side that Tesla has now been moved into the auto category for most, which makes sense. They make cars.

Lauren Schiller:                  They make cars. Where were they before?

Katrina Lake:                       They were in technology, and so there's this weird catchall bucket of people who have used technology as a differentiator that, like I think you're going to see more and more of that migrate back into. Even at StitchFix as a stock, we're covered by mostly tech people, actually, and then a couple retail people. I think you'll see more and more people recognizing that like, hey, these businesses are the same businesses they were before, just powered by technology in a way that we didn't see before. You know, I think we're both, but I think the marka tion ten years from now will probably be retail.

Lauren Schiller:                  Yeah. You had these big goals for yourself coming out of business school. Did you meet them right away? I mean, you wanted to pay yourself a salary. You wanted to have a stay-at-home business.

Katrina Lake:                       Not right away, but I really wasn't going to do this if I wasn't paying myself a salary and paying back my student loans. That wasn't an empty promise. Like, I really wasn't going to do it. So, I was very committed. I spent a lot of my second year in business school out here. I spent probably a week or so a month, like sleeping on people's couches. I was able to get a term sheet from Steve Anderson who's a seed investor who's one of the first investors I saw Kevin on. This was all real. Kevin was actually like my reference check for Steve the investor. He was the first investor in Kevin at Instagram. I was lucky enough to meet him early on and so he gave us what would now be considered a very small seed check of a half million dollars and so we closed that. In April of 2011, we started shipping fixes in that month and then I graduated in May and then kind of moved everything out here in June. I guess we closed the money a month before I graduated and so maybe I got in just under the wire. We didn't have a sustainable business model yet at that point, but I was able to pay myself a salary, pay rent, hire some people.

Katrina Lake:                       I think the other part that was important to me too in the investor thing is yes, it was important to raise money, but I think it's also important to have somebody who believes in you invested in the business. There's a lot of, I think, confidence and credibility that comes from the fact that an investor who's met a lot of entrepreneurs and seen a lot of companies, believes in the business. I think one of the things that you can do as an entrepreneur is delude yourself into really, really believing in something. Sometimes that's great and sometimes it's not reality. Having investors involved I think also helps to build confidence that like this thing is real and it's possible.

Lauren Schiller:                  How many nos did you have to hear before he said yes?

Katrina Lake:                       I mean, the seed was relatively easy I would say of just like, I think fundraising at StitchFix has always been either really hard or really easy and nothing in the middle. With him, I had worked with this woman Sue Kenderson-Cassidy who had been an advisor of mine and mentor of mine and she introduced me to him and so that part worked out well. Basically, he gave a term sheet for $750,000. He was going to put in $500,000, and he said, "Go find whoever else to fill in the rest of the $250,000. I probably talked to, I don't know, 20 or so people and everybody else said no, and I was very freaked out, like is he going to get cold feet when I go back to him and say nobody else wanted to. He actually said, and I think he meant it, he was like, "I'm glad that nobody else did. I'm happy to put in the other quarter million." I was, great.

Lauren Schiller:                  That's amazing.

Katrina Lake:                       And so, you know, he was like, "It just makes me even happier to see something when other people don't see it," is kind of the way he put it. That round we got done. Later rounds, I think, were a little bit more difficult.

Lauren Schiller:                  Did he tell you what it was he saw, I mean, what it was that made him believe in you?

Katrina Lake:                       I mean, at that stage anybody can come up with this idea. Anybody can come up. StitchFix has this great product market fit because when you tell people, wouldn't it be great if you could fill out a style profile and have a stylist who would send things to your home and then you could try things on at home and just pay for what you keep. The concept is so strong itself that I think we benefit from having a lot of just natural product market fit from it, but the flip side of that is anybody can think of that and anybody can pitch that to an investor. And so, I think with Steve it was really about am I going to be the right person to do it and honestly I had no experience that should have led him to believe that I was credible. Like, I had no entrepreneurial experience whatsoever. I had no network of engineers and whoever else to draw from, but for whatever reason he felt like I was going to be the one to be able to do it.

Lauren Schiller:                  Well, congratulations to him and to you for that. I want to go back to you maybe being a doctor at some point when you were ten. I understand that your mom came to America from Japan to go to graduate school. Did she have that immigrant mentality that my daughter must achieve absolutely everything to live up to the expectations of our new American family? Did you run into any of that growing up?

Katrina Lake:                       I'm looking at my sister. I don't know really.

Lauren Schiller:                  Keep her honest.

Katrina Lake:                       I think academics were very important in my family. Both of my parents really believed that succeeding in school, that having a great education would open doors and so I think that element was definitely very much ingrained and growing up, my mom immigrated here from Japan for graduate school and so we spoke Japanese growing up. In San Francisco there are schools you can go to so that you can keep up with the Japanese curriculum because Japan has a national curriculum and so every Saturday until I was in seventh grade I think, every single Saturday and then every day in the summer I went to Japanese school. I mean, that's like a lot of days of school if you think about it.

Lauren Schiller:                  That is.

Katrina Lake:                       Of 365 days, like, the vast, vast, vast majority of them were spent. I basically had every Sunday off. That's right.

Lauren Schiller:                  That's a lot of school.

Katrina Lake:                       I had 52 days off of school in a year.

Lauren Schiller:                  Did you resent that?

Katrina Lake:                       Well, yes. The reality is there wasn't like anything better that I should have been doing. It was so funny, too, because it was in the nineties and so everybody thought Japanese was going to be so useful. It's still useful when I'm in Japan or occasionally in a Japanese restaurant in San Francisco, but it wasn't quite the business onlot people thought it would be.

Lauren Schiller:                  It's not over yet.

Katrina Lake:                       It's more just like I do feel like they instilled the importance of education in us, so we definitely worked hard in school and definitely liked succeeding in school, and on the family side, I don't think I've realized this until being an adult and actually really in the last few years, I had a lot of exposure to women in my family who had done amazing things. Part of it was my mom immigrating here and not knowing English and she didn't learn to drive until she had had two kids in San Francisco and she was like, "Well, the bus isn't going to work anymore," and had to figure out how to drive. I mean, all of that is kind of amazing. The longer story is my mother's mom, so my grandmother, was actually the one who really desperately wanted to be an American. She had grown up in Japan at a time. She grew up during the war when Japan was in a very difficult place and she just always dreamed. She would see American movies or posters or God knows what the influences were, but she just desperately wanted to be an American. She was growing up in a time when women weren't driving. They had very little opportunity. She was in an arranged marriage. She actually ultimately did follow my mom. After my mom moved here she followed my mom here and she did actually ultimately become an American.

Katrina Lake:                       It's like an amazing thing to think that of all the things that you think are hard in life, imagine growing up in Japan in that moment and being able to think to yourself, some day I'm going to be an American and make that happen is like amazing. The other one is on my American side, actually, or on my Caucasian side. My greater grandmother, so it was my grandfather, my grandfather was raised in this very unusual household where my grandfather, basically his mom and her sister both lost their husbands. This was before welfare. It was before there were social services that were available. So, what these two sisters did was they were like, "Well, we're just going to create a household." I think they had, I need to fact check. I think they had four or five kids between them and they were like, we're just going to combine our households and one of us is going to go to work and one of us is going to stay home with the kids and two sisters are going to raise these kids together. So, my grandfather was the youngest of those. He had been raised by these two strong women. He had never even known his dad. To be able to have these examples in your life of like people doing ...

Katrina Lake:                       Anything that I achieve is never going to be as amazing as the things that they did. It's just a great example to be able to have in your life because I think it opens up kind of what's possible in a way that I really appreciate.

Lauren Schiller:                  Yeah. Do you think that changed his world view?

Katrina Lake:                       It totally did. My grandfather was the one. He like taught me to use a computer. He taught me to drive. I look back now and I can recognize those things as being really cool things that he did, but like, I think he came from a place where, oh, yeah, of course women are going to do these amazing things and of course my three granddaughters are going to do whatever they want to do and learn how to do the stuff on a computer. He definitely had a different perspective than I think a lot of people in his generation did.

Lauren Schiller:                  What advice would you give to someone who wants to start a new business? What's the one thing you wish you had known that nobody bothered to tell you, or the ten things?

Katrina Lake:                       Oh, God. There's so many. There's a bunch of things. I think one, this is a very permanent decision and so as much as you can do of like learning and validating along the way I think is really valuable. I do think there are times when you can delude yourself into like well, it's just one more product change and then everybody's going to love it or it's just one other thing. I think the more you can really get like concrete points of validation and I think it's called lean startup now, which is basically like how to build a shell of what you're going to create and then see if people like it. What do they like about it and then iterate from there rather than trying to have like a build-it-and-they-will-come approach. You know, I think that's definitely a big one. This is my personal philosophy, but I don't believe in entrepreneurship for the sake of entrepreneurship. You devote a lot of time and energy and a lot of your life to this and you really have to love it. So, not to sound like I'm discouraging entrepreneurship, but I think really making sure you have that like one thing that you really want to devote a lot of your life to. I think, I don't know, people can rush to imperfect ideas and, I don't know. I think that's one thing.

Katrina Lake:                       The last thing is just surround yourself with people who are smart that you learn from. That's true if you're an entrepreneur or just a regular person in your career like I was. You know, I think to be able to surround yourself with people who challenge you, to be able to feel like ... There's nothing worse than stasis and staying the same. It's a hard thing, actually, these days in how little I think we get exposed to other perspectives these days, but if you try to think about when was the last time I really changed my mind about something important? Like, it's a hard question to answer, and I love being proven wrong, and at work I get proven wrong probably more than anywhere else, and I learn from it. The only way that you grow is through learning and so I think that's just the best advice of like as you're building a team, as you're building a board, as you're thinking about your advisors of just really holding the bar high for people who are going to challenge you, people that you're going to learn from and people who are going to help you stay on this really steep learning curve.

Lauren Schiller:                  As the CEO of a public company it's kind of this high wire act. Like, almost anything you say could affect the share price, and you don't necessarily know what that thing is going to be. So, everyone is listening all the time. I'm wondering, as you think about the values that you want to instill in the company and what's important to you and where your priorities are, how do you balance that sort of like, "we've got to pay attention to what the shareholders want," versus, "We've got to pay attention to what's right for the company?" Maybe sometimes they don't always match up.

Katrina Lake:                       Yeah. I mean, I might have like a Pollyanna view on it and maybe we're early at this. We've been public for three quarters, but I really believe that what the right thing is going to be for the shareholders is also going to be what's right for the company, and you know, I don't look at the stock price on a daily basis. For better or for worse, I don't know what the fluctuations are or what causes them. Where we go in the longterm is definitely important and I think a lot of the things that we do are really looking at how can we make sure that we can create the most value for ourselves, for our shareholders, for our clients and the other brilliant thing about our model that I love is that there's this amazing alignment. Like, in our business model the more I can send you clothes that you love, the happier you are and the better our business is. There's like really, really great alignment that you don't always have. Like, if you think about Google's business model, for example, the more ads they can show the more ads they can get people to click on, the better their business is.

Katrina Lake:                       As a consumer you don't really want to see all the ads. You just want to use Gmail. There's this interesting, I think, kind of dance that a lot of executives have to walk of just like what's good for the business versus what's good for the customer? I have this amazing advantage where it's very aligned in a lot of the cases and so it helps us in prioritizing because if we can just focus on how can we help people to find what they love and how can we help people to find more of what they love? It just makes it really clear of what we need to do to create value. So, I'm hopeful that they are the same thing and that we won't have to feel like a lot of conflict of short-term versus longterm, but I think so far we've been, when we talk to investors we spend time with investors and it is actually in a lot of ways just like being a private company. There are investors that we can talk to at certain times and hear their perspectives. I think it's my job to make sure that everybody knows what that longterm vision is and to make sure that people all see it and believe it.

Lauren Schiller:                  We have so many entrenched ideas about how a company should be run because they've mostly been run by men of a certain age and hair color or hoodie, but Katrina Lake has been finding lots of ways to disrupt business as usual whether she intends to or not, and her vision for StitchFix has paid off so far. But it also comes with a spotlight on her every move.

Katrina Lake:                       Like, there are just these weird conversations around like well, what do you do with earnings when you're on maternity leave?

Lauren Schiller:                  That's coming up after the break.

Lauren Schiller:                  Before we get back to the conversation, I want to turn you on to a podcast that I just love. It's called Reckonings and it explores how people change their hearts and minds. Episodes have ranged from a deeply-conservative congressman who made a dramatic shift on climate change to a white supremacist who transcended a life of hate and became a force for nonviolence to two teenagers who managed to overcome bullying. In a time that feels so polarized, it's refreshing and hopeful to see people capable of such monumental shall we say reckonings. You can find in Reckonings on your preferred podcast app and at www.reckonings.show.

Lauren Schiller:                  I'm Lauren Schiller. This is Inflection Point. This conversation with Katrina Lake, the founder and CEO of StitchFix, was recorded live at Inforum at the Common Wealth Club.

Lauren Schiller:                  I mentioned at the very beginning of this the iconic photo at the Nasdaq with you and your son on your hip, and it was a head turner. Are you tired of headlines that focus on taking your company public and being a new mom or just recently there was a headline, StitchFix CEO Katrina Lake talks about leading a public company and her upcoming maternity leave?

Katrina Lake:                       My perspective on it has changed over time. I had some pride about me, I think, that prevented me from embracing that early. This is more on reflection of looking back and thinking, why did I not think I could be an entrepreneur and now I just think it's so important. And so, even if it's just like I'm just an example, like I think it's good and I'm happy to be that example and like I said, I hope there's going to be many more people after me that can be ... Like, it's totally normal. There are just these weird conversations around like well, what do you do with earnings when you're on maternity leave and you're a public company CEO? There are all these things that like, I don't really know what the right answers are and I'm going to try to figure it out. There just needed to be more, I think, just having more examples of what different types of stories look like and different possibilities look like is super important.

Lauren Schiller:                  Yeah. I mean, it's one of those sort of can't-win situations in some ways, right, because like Marissa Meyer got dinged for only taking a couple of weeks of maternity leave, and you're probably going to get dinged for taking the entire maternity leave. I mean, it's like ...

Katrina Lake:                       Well, and these situations are all really different because I think when Marissa Meyer was in her place, I think she had like active shareholder issues. She had a company on fire situation, and so was that the right thing to do when your company is on fire? This is the problem is that there's so few examples. Actually, I was with a public company CEO literally last week who he has a six-week old at home and he is taking his paternity leave. He was happy to meet me at brunch wearing golf clothes and shorts and he was on his paternity leave. I think all of these situations are unique. You can't fault, I think, one person for having a different choice, but the challenge is that there's really only two situations now that you're going to be able to look back on and I think for many other men there's hundreds. Hopefully, this can add to what people think of as what are my options when I'm in this situation?

Lauren Schiller:                  Where is your husband in all of this? Does he like ... It used to be, like I remember, I don't know 10, 15 years ago, like Carly Fiorina, when she was running HP that whole story was on her husband was at home taking care of the baby and that's how they made it possible because they invested the typical relationship. So, do you and your hubby ever talk about divvying up the responsibilities so you can both do your thing?

Katrina Lake:                       Yeah, we definitely do, and he's not at home taking care of the kids as his job full time. It's not. We have a nanny and she's wonderful. But, that being said, I think to myself like am I being sexist in thinking this because it's less about this year. I travel quite a bit, but I think about next year and I think about we're going to have two kids and one's going to be a toddler and one will be an infant, and I have this enormous guilt around that seems really hard for me to be traveling and leaving him to deal with two kids at night, even though he's not taking care of them during the day. It's a lot of work in the nights and the mornings. I would think to myself, am I sexist in thinking that because there's many, many men before me that had wives that traveled and left their two kids with their wife and probably didn't think twice about it. I still haven't figured out like how are we going to do that next year?

Katrina Lake:                       I think I'm very, very lucky and grateful that I have a husband that's very supportive and a husband that probably takes more of the mornings and nights than I do, and I do think in this world it does take somebody who is willing to kind of put in a little bit more, I think. I don't think it's necessarily that you need somebody who's going to be like a complete kind of stay-at-home parent or anything, but I do think the reality is that it's hard. You know, the reality is there's sacrifices that one or the other is going to be making every single day and then just trying to figure out how you can do that and have a healthy relationship with your kids and a healthy relationship with your spouse and it's all puzzle pieces that aren't super easy.

Lauren Schiller:                  Yeah. Wow. Well, it sounds like you've surrounded yourself with a great team that come from a variety of big-brand backgrounds and Netflix and Google and Lulu Lemon was in there somewhere. Do you have a mentor? Do you have that one person you can turn to and be like, I can't ask anyone else this question?

Katrina Lake:                       I do, and I've had many throughout my journey and I would say I have different people that I turn to for different topics, and so actually one of the things that I think has been really fun and unexpected about being a public company is that it's not like I had lots of public company CEO's that I knew. I had met a couple. I really didn't know any. It was really amazing how people kind of came out of the woodwork and helped. You know, now it's all water under the bridge, but our [inaudible 00:38:10] show process, the process to getting public was difficult. It's like in the bucket of when I say fundraising has either been really hard or really easy. The IPO process was really hard, and we weren't kind of seeing the traction we wanted to see. We weren't getting people bought into the story in the way that we needed to. And I had a public company CEO who, through an investment banker, was like, "Hey, if she needs to talk, tell her to call me. It was somebody I'd never met before who had been through the process and kind of knew exactly how I was feeling in that moment. There's been others also who have kind of reached out since.

Katrina Lake:                       I think that was network that I didn't necessarily knew existed and where I didn't feel like I was part of it before. That just kind of emerged to be helpful. That's been great. You know, I think I have, my board actually, I have a lot of great people on board who I turn to a lot and over the course of the last seven years I've bene lucky enough to kind of build a network of, in a lot of cases, other CEOs, the people who are in the space and not in the space who are going through similar things that I can talk to and get advice from and you know, I think I've been very fortunate that there are a lot of women that I've met also along the way who are very happy to make time for me whenever I ask. It's certainly something that I hope to be able to repay the favor for.

Lauren Schiller:                  What do you look for, because I know you're involved in a few things that are female-focused in terms of investments and the female investment fund, something called Moving Forward, which is about diversity. In terms of when you now look at other companies that are looking for investments, what do you look for?

Katrina Lake:                       What do I look for? I mean, I don't do a ton of investing, but I mean it is really important to me that founders that I meet and kind of companies I'm involved in are committed to building diverse teams. That has a women angle, but I think it's much broader than a women angle of like, I think one of the things that StitchFix that has made the company great is the diversity of team and perspectives that we have and so the fact that we have data scientists who are sitting next to stylists and being like, why are you picking that one? Wait, why did you not pick that one? I don't understand. What's going on in your mind? They're just fascinated and really have this great respect for the job that they do, and I think part of what's amazing about StitchFix is I don't know if there's every been like a data scientist who sat down with a stylist and gone into their brain about why they're choosing clothes. I think we've really benefited from the diversity of people and perspectives that we have. I think it's really important for founders to start like that.

Katrina Lake:                       I think one of the bigger challenges of why we see so little diversity at the top and the technology companies is because so often founding teams are built by repeat founders who go back to their network to build the team. So, they're just perpetuating this kind of lack of diversity that has existed in the industry for 20 years. No one's putting up a job posting for a cofoudner. Like, you're just drawing from people in your network. So, as I have the chance to meet with founding teams, I push on it a lot. I push in with their board. I push on it with, you know, I've noticed you don't have any women on your founding team. What is your commitment on that? I think that's an area that I think helps to make companies better and I think also kind of creates a better ecosystem for all of us.

Lauren Schiller:                  Well, let's talk about your team and how the values that you're espousing are playing out inside your company around diversity. So, your executive team is 50/50, men and women. I actually went to your website and I counted. It's true. It really is true. Most of your on-the-ground employees are women, I think 86%. Is that right?

Katrina Lake:                       The number is a little hard because we have a 3,500 stylist organization and the vast majority of our stylists are omen. These are women who are working part time and mostly work from home. So, that skus the number to make it 80-something overall company wide, but then we also have 1,500 warehouses where it's about 50/50. Our headquarters I think is about 60/40 women to men. So, if you put in the 3,500 stylists into our 6,000 employee figure, then it becomes very skued sounding, but on average it's a little over parody where we have women a little more represented than men.

Lauren Schiller:                  One of the things I've been thinking about is we already know what the downsides are of a culture dominated by men and so I'm just thinking about what happens when you have a company that's kind of dominated by women? What's the outcome there?

Katrina Lake:                       I mean, first of all I would contest that culture dominated by women. Our management team is 50/50. Our board is 60/40 women. Like, I don't think that's dominated by women and I don't think that you would ask a male CEO who is progressive enough to have a 50% female management team. Like, you would never ask him about a culture that's dominated by men.

Lauren Schiller:                  I might now. I might now. I mean, maybe not five years ago, but now I definitely would. I'm just curious. I'm not saying that's what your situation is, but just sort of philosophically speaking, if there's any sort of up sides or down sides to having, even jut having at 50/50 is, in a sense, more dominated by women than it has been in the past.

Katrina Lake:                       Unquestionably, it is more so. I don't know. I mean, I think the down side is I get questions like that not in an insulting way, but in a way that like it's not obvious to other people, like that it's not something people are experiencing all the time, so it becomes something that is unusual. I think that's unfortunate, because I think there's a lot of up side to it. I think there's a lot of upside to it just like having different perspectives in diversity. I think there's also, we were just talking about parenting, so it's top of mind for me, I think there's also a lot of upside from the perspective of people who are men and women who are trying to live a life and work. I think there are a lot more conversations and there's a lot more empathy that happens when you see both sides of the equation every day at work. I don't know. I think, it's also all I know. I can't speak to the downsides or the upsides, but I think we've been able to create a place that people love to work and that has been able to take kind of this what people academically talk about is being important, and diversity and actually show, this is what it looks like and this is how it works and this is an example of it in a way that I don't know that we've had a lot of examples before.

Lauren Schiller:                  All right. I have one last question for you, which is an Inforum tradition, which is your 60-second idea to change the world?

Katrina Lake:                       I don't know that I have a specific idea, but like, I think that one of the things that has been a real challenge, and you can see it in kind of the political landscape also and loss of community. So, I think even just like this group of people getting together to do something like this in an evening is a really great part of that. I think there's been just kind of a loss of humanization of a lot of things that we do. So, when w'ere buying things, the way that we engage with each other, like a lot of it has been kind of dehumanized in a way that I think has taken away from communities. So, I don't know what the exact ID is, but ways that you can bring more commerce into communities, ways that you can make things like buying clothes a more human experience and a more human-to-human experience I think brings back the humanness that connects us a country and as a community.

Katrina Lake:                       I think a lot of, especially in eCommerce, it's become very anonymous and very transactional and I think that the harms of that are greater than what we're seeing in terms of the impact that it's having on how we think about each other and how we think about the space that we occupy together. So, I'd love to see anything that kind of just brings back a sense of community and brings communities together in more human ways.

Lauren Schiller:                  Katrina Lake's company StitchFix is often described as being at the intersection of fashion and technology, but at the end of the day she's using technology to solve one of the oldest problems in the book, what am I going to wear, and she's doing it by putting people first. It's bigger than just how we shop for clothes. She sees a problem with the lack of diversity in tech and makes sure her company is an example of how diversity makes good business sense. She sees a problem with the lack of parental lave and has made it her dedication to family as much a part of her public identity as her extraordinary success. I look forward to the day when Katrina's success and her dedication to a diverse and family friendly workplace is no longer extraordinary. It's just how business is done.This is how women rise up. This is Inflection Point. I'm Lauren Schiller.

What Happens When Sexual Assault Goes Unpunished: Sarah Delia, Host of “She Says”



When radio journalist Sarah Delia heard a story about the sexual assault of one of her listeners, “Linda” (not her real name), she knew it was a story that needed to be told. It’s also a story about how one survivor took matters into her own hands when the police department she turned to for help seemed to be failing to help her. And it’s a story about how our criminal justice system handles sexual assault cases nationwide--and what needs to change to make violence against women the exception rather than the status quo.

Sarah turned Linda’s story into a new investigative podcast series called “She Says”. Listen to our conversation about the courage it takes to tell your story of sexual assault--and keep telling it---until you are heard by someone who can help you get justice. And also--what it takes to be the person who takes on the “second-degree trauma” of listening to and reporting on stories of sexual assault.

To learn more about what to expect from the criminal justice system in cases of sexual assault--and how you can help advocate for better policies, you can check out these resources on the Rape, Abuse & Incest National Network (RAINN).

She Says also has a list of resources on their website.

And if you or someone you know is a victim of sexual assault and need to talk about it with someone, call the National Sexual Assault Hotline: 800-656-HOPE.

TRANSCRIPT

Sarah Delia  Photo by Logan Cyrus

Sarah Delia

Photo by Logan Cyrus

Do haters deserve our compassion? Sally Kohn, Author of "The Opposite of Hate"

Can you find compassion in your heart for the haters in your life? CNN political commentator and first-time author Sally Kohn says if we keep on hating the haters, the cycle of hate will never end.  She’s believes compassion to be one of the keys to breaking the cycle of hatred that pervades our culture in today’s divisive world. 

The question is, how can compassion defeat a system fueled by hate? 

Listen in on my conversation with Sally Kohn, author of “The Opposite of Hate” on what she’s learned from her own missteps as a former school bully and, paradoxically, as a well-meaning liberal, breaking the cycle of hate, and cultivating compassion for her perceived enemies.
 

Photo by Paul Takeuchi

Photo by Paul Takeuchi