Tuesday, 20 September 2016

Gwyneth, Lena, and Jenni Get Down to Business

 
The Entrepreneurship Issue
 
     
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September 20, 2016 | Letter No. 52
 
 
 
 
STORIES
 
Gwyneth,
Biz Guru
 


Lena Dunham and Jenni Konner
 
 
Swivel
Beauty
 


Meena Harris
 
 
Changing
the Culture
 


Shivani Siroya
 
 
Art Baby Hustle
 


Laia Garcia
 
 
Pope the Barber
 


Ben Cooley
 
 
 
 
 
 
  My dearest and most cunning Lennys,

Welcome one, welcome all to Lenny's first entrepreneurship issue. Let me start by saying that I really struggled over whether it was possible, or even right, to build an issue around the most confusing spelling word we have in the English language. I have never once spelled entrepreneurship correctly without the aid of AutoCorrect and took to calling this, in my head, "the poonership issue," which does not connote the seriousness with which we want to tackle the subject of women starting and building their own businesses.

The pop-culture perception of entrepreneurs is a bunch of men in rooms having million-dollar ideas and screaming, "We gotta get this patented!" That, or women dreamily starting their own cupcake emporiums. Meanwhile, as Jenni says, "My concept of entrepreneurship started with Daddy Warbucks, became Oprah, and then it was Shark Tank." (Mark Cuban is the only celebrity I have ever seen her ask for a selfie with, and that's a fact.)

But through Lenny we have spoken to so many remarkable women running businesses who are both independent — often turning to bootstrap financing owing to a lack of institutional support — and revolutionary. They're revolutionary because these businesses were created when one woman had the strength and confidence to bet on herself.

Reimagining what an entrepreneur looks like made me remember a girl I went to college with — let's call her Lisa. She walked around campus in the most adorable, perfect mod outfits you've ever seen. Compared to our collegiate sweats and ironic vintage tees, she was a spread in Nylon Magazine — all quilted minis, go-go boots, and perfect (read: not cheap) little handbags. There was no one at school dressing like her, and I had to assume she had been given an all-access pass to her father's gold card.

Finally one day, as we sat on the grass in a group, I just asked her: "Lisa, you have a new outfit every day. What gives?" Turns out this young woman had honed in on a secret and surprising skill: patchwork. She could design it, sew it, and turn it into hoodies, pants, and weird floppy tote bags for, you guessed it, Phish fans. Was she a Phish fan herself? Nope. But lots of nights of sewing and a few parking-lot sales-a-paloozas at their biggest shows, and she had the cash she needed for full self-expression. Goddess bless Lisa and her slanted, strawberry bangs. At the end of the semester she gave me one of her patchwork hoodies. It was quilted corduroy, with a mushroom and a star set against a gingham night sky, and it sits in my closet to this day.

That Lisa had a mini-industry getting her through college shows how entrepreneurship is also a socioeconomic issue. When Jenni and I started Lenny we had plenty of fears, but we also had well-paying day jobs to fall back on and no college loans to pay. Most Americans do not have these luxuries. They're too busy actually trying to earn. As Andrew Yang wrote in a recent article in Quartz: "Research shows that there's a substantial correlation between a person's socioeconomic background and the likelihood of their starting a company. Too many potentially important companies never come to fruition because startup culture — intentionally or not — marginalizes women, underrepresented minorities, and first-generation college students."

So how can we move toward solutions that make it possible for people born without the kind of connections that yield capital to follow their unlikely dreams? The nonprofit Corporation for Economic Development has some ideas for systemic change that would make it easier for the not-rich to start their own businesses, like providing tax relief and tax credits for the self-employed and providing public funds to support entrepreneurship among community-college students. Voting for politicians who back these kinds of policy changes is a necessary first step.

For our inaugural celebration of women doing business for themselves, Jenni and I interviewed Gwyneth Paltrow, who was so generous with her talent, vision, and medical advice as we started this venture. We were anxious to know how she started and maintains her newsletter and e-commerce juggernaut Goop while also rising above constant criticism. As she recently told me, "I don't have to rise above it, because nothing fucks with my bottom line."

We also talk to the multitalented Grace Miceli about turning her feminist art into a viable small business, and we hear from Shivani Siroya, the CEO of Tala, which makes traditional credit more accessible to underserved markets in developing countries, about redefining what we see as a Silicon Valley CEO. Meena Harris talks to the women behind Swivel, an app bringing new hairstyling resources directly to black women, while Pope the Barber tells us about turning her barbering skills into a lifestyle brand.

I know I finished this issue feeling inspired to finally tackle my vision for a chic pencil-case necklace (huge seller, right?! Do NOT steal this idea).

Go forward in industry, dreaming your wildest dreams!

Love,

Lena
 
 
 
 
 
 
Gwyneth Paltrow, Business Guru
 
 
Gwyneth Paltrow illustration

(Danie Drankwalter)

Gwyneth Paltrow is nothing like you think she is. Gwyneth Paltrow is exactly who you think she is. In the end, none of this fucking matters, because she has never been anyone but herself. Thank God, because here's who Gwyneth is to me: a vital friend, generous with her knowledge and passions. An ass-kicking cook, but you already know that if you follow me — or anyone else — on Instagram, because her recipes are obsessively tagged. An engaged mother who sees the humor and beauty in child-rearing. And a determined businesswoman who demands that no female question her own value in the marketplace.

On that last note, Gwyneth has been our trusted adviser from day one. She took my and Lena's calls day and night to counsel us on foreign concepts like ad sales and back end. She huddled with us in the corners of parties to firmly (like, using a lot of profanity) explain to us what retaining ownership of your own company means, both practically and on a bigger scale. She's been in the newsletter business for eight years, and she imparted every bit of hard-earned wisdom to us as often as we asked. She's also a goddamned delight.

We are so excited to feature her in our entrepreneurship issue because she is the definition of a strong woman running her shit. As she once said to me, she left a perfectly good day job to start Goop. And some days she still wonders why. Which is, of course, her prerogative. And ours is to be so grateful that she did.

Below, Lena and I talked to Gwyneth about the nuts and bolts of starting a business from your kitchen, how to scale up while still keeping your authentic voice, and, of course, steaming your vagina.

—Jenni Konner

Jenni Konner: You told us you sent the first Goop email from your kitchen in London. How did you describe Goop? If someone said, "What is this thing in my inbox?," how would you have explained it then?

Gwyneth Paltrow: I don't know why I started it. There's an aspect of my life where I just follow these threads. I've always been that person for my friends, where they ask me, "I have a guy coming over for dinner. How do I roast a chicken?" Or, "Where do I get a wax below 14th Street?" Or, "Where do I get a cool poster?" I had this incredibly fortunate life where I was getting to travel and work all over the world. I always had notebooks where I'd jot down, like, where's the best pizza? I'm in Naples, let me go try them all. So I had all of this information, and it was originally going to be a tiny database for my friends so they would stop fucking calling me.

Then, some part of me thought maybe there are other people in the world who want answers to the same questions that I want and that my friends want. Then it organically turned into Goop.

I think I would have been absolutely stumped if you asked me "Why are you doing this?" in 2008. I wouldn't have been able to tell you why, and there have been many times over the years that I've been doing that, that I'm like, "Why am I doing this? This is totally excruciating and unrewarding, and really painful, and everyone hates it and hates me."

JK: How many people did you start with?

GP: Just me.

JK: Just you, in your kitchen, writing an email.

GP: Yes, and making the recipes and writing them down and sending them out.

JK: How did it grow?

GP: Very quickly I had a lot of subscribers, and I had a very engaged group of subscribers. I was going along, and then I started getting feedback that I was really changing the financials for companies that I was recommending on the site and having a significant impact on their business. The word really started to get out.

I remember a few people approaching me: "We really love what you are doing. What are you going to do with it?" There's one woman, her name is Juliet de Baubigny, and she's a partner at a VC [venture-capital] firm in Silicon Valley called Kleiner Perkins. I was at Elizabeth Murdoch's house in London for some garden party, with all these world leaders and shit there, and this woman came up to me and she said, "I really love Goop," I didn't even know what a VC was at that point. I had never heard of Kleiner Perkins.

She said, "I really love what you're doing, this is what I do, and what are you going to do with it? There's really something here." I was like, "I really don't know. I never really thought about it." She said, "You really should start to think about it." She became a guardian angel and started to push me gently toward not necessarily monetization, but thinking about what could it possibly be.

She introduced me to my first CEO, Seb Bishop. He was very excited about the possibility. It was right at the time where there were all these models like Shoe Dazzle, and all the flash-sales sites were happening, so there was a lot of thought about, We could do this, we could do this, we could do this, and I just thought, No. That's not what this is. I recognized early, before I even knew that it could be a viable business at all, that I had trust. I had the trust of my readers, and I had unheard-of open rates.

Lena Dunham: I wonder how you think about growing — scaling up — while still maintaining that trust with your readers. How do you make sure that everything you're doing feels organic to you and feels organic to them?

GP: For me, it was a nonnegotiable part of the thing. For example, when we started taking advertising, there were a lot of brands that I turned down. It just doesn't feel right for us, so I'd rather not have the money than have somebody click on it and be like, "Why the hell is this on here? This feels terrible." We try to do a lot of native advertising, so we're designing it, it's in the look, it's in the feel. If we're choosing a brand that we love, I put things on there that I love or use anyway, so that's a big part of it.

JK: Do you have big regrets? You're not a very regret-y person, but is there something, about which you say, "Oh, I wish I did that slightly differently. I wish I had waited longer on that." Do you have any of those?

GP: When I started, I was so earnest. Sometimes I'll see an early incarnation of a page, and I'll read something I wrote, and I'm just like, "Oh my God." I had to learn as I went. You don't appeal to as broad of a range of people when you're that earnest. You have to be a little bit more savvy about how you communicate. It doesn't mean that I'm not still me, but …

JK: I would say you have an earnestness, but you actually also have a great sense of humor. That's what you were leaving out. The full scope of you.

GP: Right. Exactly. Sometimes that, I'm like, "Oh. I wish I had gotten that piece of it sooner." In a way, I wish that I had more infrastructure sooner, because now I'm eight years in, but I'm really only two years into real monetization of the site, and it's so much fun, and I'm learning so much, and I'm so engaged in what I'm doing. I wish that it hadn't taken me so long to be brave enough to say, "Hey. Let's make this a business."

LD: What it was like for you to go out and pitch the company? It's scary to bet on yourself; it's also scary to ask for money and to ask other people to bet on you. How did you overcome that fear, if you ever had it?

GP: I definitely had it. I'm not that person, intrinsically. I don't like to ask for help, ever. Luckily, by the time I went to raise my little seed round, it was from this incredible group of women. They already knew what I was doing and they loved it, so it wasn't like I was cold-calling like, "I have an idea." Then there's no way.

LD: Something we've talked and thought about a lot, is the way men are encouraged to expand beyond their careers. Ashton Kutcher was on That '70s Show and now he gets to start 57,000 restaurants and be an investor in Twitter and no one says anything. And you're this Oscar-winning person who's been told, "Who told you that you could do this?" I wonder if you've experienced this sort of misogyny as an entrepreneur.

GP: The "stay in your own lane" vibe.

LD: It's constant.

JK: Even just with projects, people say, "Well, how are you going to do a TV show and a movie and Lenny and …" I just don't think anyone's asking J.J. Abrams that.

GP: Of course they're not. They're not asking Ryan Murphy that, and he has more irons in the fire than anyone. Everybody wants you in the caricature of you if you're a woman. You're supposed to be this and I'm supposed to be that. If you start to cast that off, it makes people very uncomfortable, especially if they're projecting a lot onto you and they identify with you.

It's threatening to men to have women who are capable of doing so many things and doing them well. I don't think it's consciously threatening and I don't think it's all men, but it really challenges the status quo and how people relate to us. Because I was the first one of this generation to do this kind of thing, I got a lot of shit for it. I sort of welcomed it. Now I'm like, this is why I'm on earth. This is part of my journey, and I'm here to be this person, and that's OK.

I was genuinely surprised at the vitriol. I mean, honestly, I sent this nothing issue from my kitchen that had a recipe and two things in it, or maybe it was just a recipe. I don't even remember. It had nothing in it, and the New York Times wrote maybe a four-page article. It's unbelievable. The response was totally bananas.

LD: And totally different than the response you were getting from your readers, which was one of "Thank you for sharing with me. Thank you for being open." Have you ever let any public reaction to what Goop is shape what Goop became?

JK: Positive or negative.

GP: Not really. There's certain things, I've just gotten savvier as I go, so now if I'm writing an article about someone steaming their vagina, I'm like, "This is going to be a thing." It's fun.

LD: Honestly, my first reaction was like, "I can't wait to steam my vagina."

JK: We need the ghosts of old lovers to leave us.

GP: Originally it would take me by surprise so much when we would publish something and there was a huge reaction to it. I was so perplexed by it a lot of the time. Now, it's pattern recognition. I can tell you, for the most part, what people are going to think about X, Y, and Z.

It's strange to also make that transition from "Oh no, oh no" to "I don't fucking care." I'm very unapologetic about it. I really believe in what I'm doing, and I really love what we're doing, and I love the product we sell. I think it behooves people sometimes to make assumptions or whatever, but we're really just trying to provide the best product and information.

JK: In your criminal mind, what does Goop become five years down the road?

GP: In my criminal mind, I want to continue to get better and better at what it is we're doing, which is making a really exciting product that, I hope, will slightly disrupt the direct-to-consumer model that exists now, which is on more of a mass scale, with product that is more aspirational but coming to the customer at a direct-to-consumer price point.

I always want to curate other stuff and I'm hoping that we'll always be able to do that, and that the voice will be very cohesive. I would like to see growth in all areas. I really hope that, whether it's in how many subscribers we have, or our ad-sales business, that year after year, are able to realize our vision: We want to make every choice count. We want to be the most trusted source on the web for us and our friends, and our friends' friends, and concentric circles out.

Again, I think the business will dictate to us what direction it's going to go in. Like, are we going to continue to grow in each vertical across all the verticals? Or in ten years are we only going to be a beauty business? Who knows? My hope is that we are a truly modern lifestyle brand and that nobody remembers that I started it.

This interview has been condensed and edited.

Lena Dunham and Jenni Konner are the co-founders of Lenny and are steaming their vaginas right now.
 
 
 
 
 
The Best Friends Behind Swivel, a New Platform for Black Hair
 
 
Hair salon illustration

(Danie Drankwalter)

Historically left out of mainstream consumer markets, black women who have built businesses based on their unique needs are in many ways some of America's original entrepreneurs. This is especially true for the hair-care industry, which was revolutionized in the early 1900s by Madam C.J. Walker, widely recognized as the first woman self-made millionaire in the United States. As one of the pioneers of modern hair care, Walker not only inspired generations of black women to go into business, but she also was an early and passionate advocate for women's economic independence: "Don't sit down and wait for the opportunities to come. Get up and make them!"

Following this credo, and carrying Walker's legacy into the digital space, are two women who recently launched Swivel Beauty, a beauty-review and booking app that caters exclusively and authentically to the hair needs of black women. After they came up with the concept and began to build their business, co-founders Jennifer Lambert and Jihan Thompson became the quintessential part-time entrepreneurs so many of us with a day job and a side passion can relate to, spending countless hours before and after work and over weekends trying to turn a good idea into something real. What follows is a conversation with the two about the need for a platform like Swivel, the challenges of the side hustle, and what it's like to start a business with your best friend.

Meena Harris: How did you come up with the idea for Swivel?

Jenny Lambert: About a year and a half ago, Jihan came up with the brilliant idea to start a blow-dry bar for black women, so that they could fit into the new trend of express hair services, which women who have our unique hair needs haven't really been able to take advantage of.

MH: Does that mean Dry Bar isn't good for black women?

Jihan Thompson: It can be good. The issue is that you don't always know if the stylist you're seeing can do kinkier, curlier curl patterns. While there are some great stylists out there who are able to, you can't just walk in and see anybody and expect the same result each time. We wanted an experience where you could drop in and go to any stylist and know that your hair would turn out awesome.

JL: When you book an appointment with Dry Bar, you can make a specific request by noting that you have kinky, curly hair, or that you're black and would like a stylist having experience with your hair type. But they can't guarantee that's what you'll actually get when you go in for your appointment. I've gone a few times, and I've actually been pretty lucky, in that even when I had someone who wasn't black, she could handle my hair. My hair may have turned out great, but there have been times when a white stylist said things like, "Wow, your hair blows out really straight!," because she's surprised. Uncomfortable experiences like that happen.

MH: Here's what Dry Bar had to say: "Our 3,000-plus stylists … go through extensive training on all hair types and textures. Even so, when a client lets us know about her particular type of hair when making an appointment, we do our very best to pair them with the right stylist."

JT: We found that, for express hair services, black women still end up doing their own research. Because they're not able to just walk in, beforehand they look for recommendations to go to a specific person who's known to do a great job on black hair. There isn't a single place where all of that information is categorized and where you can read reviews with essential details.

Dry Bar has a lot of great people, so we don't want to say that the whole experience is bad, but we thought about how we could build on the concept to make it more inclusive of different hair types and textures. That was our initial idea at least, basically to start a Dry Bar for black women.

JL: But after looking at the numbers and evaluating our respective skill sets, we realized that we weren't the best team to start a brick-and-mortar establishment, especially given some of the financial requirements, like paying rent.

JT: We didn't have a lot of up-front capital to rent a place for five or ten years. Then we began getting into the weeds of, how do we find these stylists? How do we train them and create a program for quality control? With all of those considerations, we knew we needed to choose a different direction, especially because there are a ton of great stylists already here in New York City and across the country; they just need an easier way for clients to find out about them.

MH: Why can't black women reliably use Yelp for hairstylist reviews?

JL: Yelp probably is the best alternative to Swivel, but we want to focus more on the information that we know women are looking for when they are reading Yelp reviews. Such as: How talented is the stylist? How long am I going to be waiting there? What's the general salon experience? We want that condensed in a way that's useful and uniform so that customers can more quickly glean the information they're looking for. Yelp now has too much information, so you can search for "black hair salon" and get results for salons where they'll dye your hair black. Having a platform that's exclusively about black hair salons filters the subsets.

MH: There seems to be less information available to black women looking for stylists who serve natural-hair needs. Given that natural hair is a well-established trend, is it just a lack of information, or is the community still pretty small, but growing?

JT: In the natural community, there's been a lot of emphasis on DIY. We believe that's a consequence of women just not knowing where the stylists are, because there definitely are a lot of them. Also, a lot of natural-haired women tell us they are protective of their curls and that they can't risk getting a bad haircut or a bad blowout. Because women with natural hair don't have time for the trial and error that comes along with doing the typical research we discussed earlier, they would rather not go at all than go and have a bad experience. They don't want to risk damaging their hair that has taken two years to finally grow out!

MH: You are childhood friends. How did you become business partners?

JL: We're always surprised when we meet people who say they dream of being an entrepreneur but that they need to think of an idea first. For us it was seeing a problem that existed and wanting to build something to fix it.

JT: I don't know if I can honestly say I always had the entrepreneurial bug. But as an editor and a writer, I've spent years interviewing people — and in particular female founders — who followed their passions and started their own businesses. Many of them would say, "I just decided one day I was going to do this." When you're around that so much, you stop thinking, I can't do this, and you start asking, Why not? Why couldn't I be the one to start this? Especially because if someone else created Swivel, I'd definitely use the service.

I had no background for this, but I wanted it to exist in the world, so I made it happen. I still really loved what I was doing full-time, though, so I decided to try it out first as a side business and see where it went. If it didn't work out, I was fine with that. I've talked to so many women who had "side hustles" that turned into real things, and so many whose part-time ventures turned into nothing. It's a matter of whether you're willing to put the effort in, to wake up early before work, do it all weekend long.

MH: Swivel launched just this summer. What's been the state of the business until now?

JT: For the last year, we worked on the concept, thinking about where we wanted to see it grow. We built a website last summer on WordPress, which kind of looked like the first version of what we wanted it to be. It allowed us to make it feel real, but it didn't do everything we wanted. It also gave us a chance to start meeting with salons and stylists, to hear what they needed and also to share our vision. That time period was a lot of weekend hours, before work, talking to people on the phone, and catching them on a Saturday morning.

But it was really after we attended the Rent the Runway Project Entrepreneur one-day conference last year in New York when we got motivated. We left asking ourselves what the real next step would be and how we would stop talking about the business and really build it. We hadn't yet found an engineer, which everyone knows is super-hard to do, so first we found a developer team, and we decided that we were going to move forward. We were ready to bootstrap it, to self-fund, and build the first version of our app that would allow women of color to find and book appointments with stylists and salons that cater to their hair texture.

We've been working with coders whom we found on Facebook, and the team is based in Vietnam, so the time is completely flipped. When we got home from work, we started talking to them during their morning, when they were getting into work. I was waking up at 4 a.m. to answer emails, as they were nearing the end of their day, because I wanted to respond to them before they went to sleep. While they slept, I was at my "day job." In one way it was sort of crazy, and in another, it was kind of perfect.

MH: For most of the time that you've worked on Swivel, both of you have been the classic "nights and weekends" entrepreneurs. I suppose I am, too, and from personal experience I know that it's exhausting to do it well. What has that experience looked like for you? What advice do you have for women starting off with a side venture?

JT: It's very hard to give it your all on nights and weekends. It's not impossible, but we were giving over 100 percent to our day jobs, because we don't have traditional nine-to-five jobs. There would be weeks that would go by and we would do nothing on Swivel, because I was closing a magazine issue, or Jenny was dealing with something really intense at work that was time-consuming.

We had to get comfortable with the fact that this was probably going to take us longer to do while we had full-time jobs. You have to have that sort of patience. You can get easily frustrated, and I see why people give up, because it's not moving as quickly as we hoped. We knew that we were in it for the long haul and that eventually we would get to a point where we could work on it more fully.

JL: Something that I'm still working on is finding the discipline to set aside time that's exclusively focused on Swivel. As you know with law-firm jobs, no day is the same, so even finding the energy and staying the course is hard. But one amazing thing about working with your best friend is that it's great to work together. Not only do you not want to quit on the business, but you also don't want to quit on each other.

This interview has been condensed and edited.

Meena Harris is a former lawyer and now manages tech policy at Slack. She is also the creator of I'm an entrepreneur, bitch, a brand that supports and promotes women's economic empowerment.
 
 
 
 
 
Changing Silicon Valley Entrepreneurship Culture from the Inside Out
 
 
Silicon valley illustration

(Danie Drankwalter)

A few months ago, I was at a conference, chatting with a guy friend of mine who runs a tech startup. After catching up about our companies, we somehow got onto the topic of his running a marathon, and I shared my obsession with high intensity interval training, or HIIT, workouts. This shocked him. Maybe because I'm on the small side, or maybe because my voice is a little quiet, he had pegged me for a yogi — he hadn't expected to learn that I prefer to jump around to loud hip-hop and raise 25-pound sandbags over my head.

He told me that he didn't realize it before but that perhaps I was a ruthless competitor after all. "Maybe you really will take over the world someday," he offered. Just because he now knew that I love short bursts of high intensity exercise.

I'm pretty sure he meant this as a compliment, but I didn't take it that way. I was disappointed and mildly insulted to think that my workout regimen — more than our company's groundbreaking technology and vision — would be seen as a harbinger of future success. But I shouldn't have been all that surprised.

Those of us who are trying to build tech companies know that Silicon Valley favors a certain kind of entrepreneur, usually a white man with an outsize, bloodthirsty personality. We've all read the book/seen the movie/watched the news story about the CEO who works his teams into the ground, wears pajamas to pitch his company, adopts obsessive personal habits like eating nothing but fruit, and still manages to inspire confidence and trust from the industry. Before too long, we're led to believe that success in Silicon Valley is predicated on this kind of persona, and we start to use it to decide which people — and which companies — get to be successful.

The problem with this definition is that it excludes all the many, diverse forms that ambition can take and makes it harder for those of us on the outside to work our way in. We outsiders are just as wildly obsessive about changing the world as our white male counterparts, just as dogged in pursuit of our goals, and just as brashly creative. But because we don't conform to the typical entrepreneur mold, and because our companies often serve underserved populations (including other women!), we face a lot of bias. I've thought a lot about how to best position our company for growth and success. I've started joking that I should take meetings at the gym. But the reality of what we're up against, as women and minority tech leaders, is a lot more complicated and even contradictory.

Here's what I mean. Our company works in East Africa and Southeast Asia building credit scores out of mobile data so that people outside the financial mainstream can get access to credit and other critical financial services. This focus on low-income populations outside the United States, combined with my ethnicity and gender, places our company easily in the "outsider" bucket. Most of my industry peers have no reason to use — and certainly don't need — our product. We can't be described as "Tinder for dog sitters" or "Uber for artisanal soap" or … you get the idea.

It also means that, most of the time when I'm pitching investors or speaking at conferences or even just at a cocktail party in San Francisco, I have a lot more explaining to do up front. I have to explain, often to an audience of mostly white men, that my interest in emerging markets isn't a charity project; that, yes, a good portion of people in these markets have smartphones and purchasing power and business acumen; that, no, they don't have access to traditional banking, let alone credit cards. I have to undo the perception that Africa and Southeast Asia are places that depend on aid and replace it with the fact that they are now, increasingly, places to do business. I have a lot more work to do just to prove that I — and my company — deserve to be in the room.

The irony is that if I borrowed from the boys and rolled up to meetings or conferences in a hoodie, I'm not sure I would be taken seriously. If I were loud and combative, if I had dropped out of school instead of studying econometrics and working in banking and emerging markets, would anyone believe that I was capable of building a company that can take on the global financial sector?

I've met women who are worried that they're too pretty to get coveted engineering jobs, or worried that they're not pretty enough to get attention as CEOs. I've talked with women who downplay their compassionate company culture in meetings with investors, and women who've been told they're too rough around the edges to ever be good leaders. And then there are the women who design technologies and products for women, and who are driven mad trying to explain their innovation to a room full of men. We outsiders bond over these biases and double standards in the dark corners of cocktail parties and events and conferences, and we mostly all agree on one thing: the industry, and the kind of culture it fuels, isn't changing anytime soon. But the more we can stop worrying over what the industry does or doesn't expect of us, the more we can start paying attention to the type of leaders we want to be and the companies we want to build — and start proving the value of our unique approaches.

There's a recent wealth of data and studies and reports showing that women-led companies tend to outperform those led by men, and that diverse companies outperform their less-diverse peers. And there's a small but growing list of male investors who are proudly, publicly bragging about the success of the female-led companies in their portfolios — and acknowledging the barriers and biases they face. I was heartened earlier this year to read Mark Suster's passionate defense of uBeam founder Meredith Perry after a particularly ugly media storm. And I continue to be inspired by a growing cohort of female peers who are all daring to do things their own way, from Google alum Kim Scott's showing us how radical candor can make us better leaders to Anu Duggal's leading a fund for women founders to Girls Who Code founder Reshma Saujani's urging young women to be brave and not perfect.

Sure, I like HIIT workouts, but I think I'm a good leader because I listen to and learn from the people around me, and I worked like a dog to get to know our market and our customers. Before I started our company, now called Tala, I did thousands of interviews in India and Africa with small-business owners, to learn about their needs and barriers and goals. I also learned their unique, often courageous stories — and I built our company around the idea that the stories of their daily lives could prove their value to a financial system that didn't believe in them.

I'm proud that we're a company driven urgently and tirelessly by our mission to provide billions of individuals with choice and control over their financial lives. I'm proud that we value people — both those served by our product and each other — and that our focus on teamwork helps us meet goals faster and more effectively than anywhere I've ever worked. And I'm particularly proud, by the way, that 48 percent of our company's employees are women and 73 percent are nonwhite. We hire the best people for the jobs we need them to do, which includes living up to our company values of individuality and inclusivity. In the end, we may look unfamiliar to — and even at odds with — a lot of our industry, but we're proving that our way of doing things can be a viable, and maybe even a better, path to success.

In an industry and a culture that value a more ruthless machismo, daring to follow a different path can be a revolutionary act — one that certainly has all the hallmarks of courage and irreverence that define the most successful Silicon Valley entrepreneurs. So, like the men who came before us, I think women entrepreneurs should find the courage to pursue our goals in the best way we know how. It's the start of a new kind of success story, one that can open up our sector to a more diverse set of leaders. And it may help lead to the creation of more inclusive technology that transforms people's lives across the world.

Shivani Siroya is the founder and CEO of Tala.
 
 
 
 
 
Art Baby Girl Hustle
 
 
Grace Miceli illustration

(Danie Drankwalter)

When I discovered Grace Miceli's work on Tumblr, it changed the way I saw myself as a woman living in the world. Truly. And it wasn't just her art — her perfect portrait of Gwen Stefani with blue hair and braces, or the painting that simply said GIRLS AT NIGHT ON THE INTERNET — it was her selfies and the other feminist artists she reblogged that opened up new worlds for me. It was like Grace's work allowed me to fully embrace my womanhood in every single way — my femininity, my feelings, my sadness, my desires. As soon as I found out she was moving to New York City, in 2011, I invited her out on a friend date (we had become Internet pals by then, so it wasn't totally creepy).

Since then, I have seen her thrive, whether because of her art, or because of the supercool clothes she makes emblazoned with her colorful, almost childlike illustrations, or because she's traveling the world as a freelance curator with Art Baby Girl, the online gallery space she started while still in college. Most recently she was in Taiwan and Taipei, where she curated a show featuring young feminist artists. I've always admired Grace because she's so uniquely authentic and fully understands the art of the hustle. She knows it's never-ending, and essential.

As we were thinking of people to feature in this issue, I thought Grace would be such a perfect person to talk to: she's self-made and she is also still at the beginning of her career. I figured she would have valuable advice and perspective to everyone else who is also trying to make their side gig into their main gig, or even if they're just trying to start their own creative business. Grace was candid and funny because she just simply cannot be, and we talked about early Internet usage, why Instagram matters, and why cute bunnies that say "Fuck the police" are important.

Grace Miceli work on Instagram

(Grace's work on Instagram)

Laia Garcia: Did you always want to be an artist? Were your parents supportive?

Grace Miceli: Yes. It was something I always knew I wanted, but it took me a very long time to realize, and to gain the confidence to actually pursue it as a career.

My parents both are the type of people who have day jobs [while still pursuing their creative interests]. My dad's in a bunch of bands and my mom's an artist. They said, "You can study whatever you want, but when you graduate you have to support yourself." They were always super supportive, but they were like, "We're not going to pay your rent if you just want to be an artist."

LG: And you studied photography while you were in college, which is a bit surprising.

GM: My major was photography because at Smith, if you couldn't paint or draw well, like in a realistic style, then that is your major. I had an interest in it, but it was more of a, Well, I guess I'll do this.

Toward the end of school is when I started to draw in my own style that I've developed. My attitude was much more, Fuck it, I'm going to do whatever I want. It took me a while [to get there]. It took Tumblr and finding people who were into my art online to have the confidence to do that, because in school that wasn't encouraged. I couldn't show those drawings in a crit.

LG: That segues perfectly into my next question: Did you always have an online presence?

GM: LiveJournal is where I started. I used it as a diary type of thing, but that's where I started posting my art. At some point in the middle of college, I got Tumblr, and that became the main thing for a while.

LG: When did you first start selling your art?

GM: Toward the end of college, I started making zines, and I'd sell them online for a few dollars. It was always a very slow thing, like I'd post drawings and a lot of people would be like, "You should make stickers!" Or, "You should put this on a shirt." You have to listen to people. I tried it, and it worked. Obviously for years I was not even covering my production costs because I always sold things for very cheap. But it was more important to me that people could buy what I was making than making money from it.

LG: Did you have a plan when you finished college and moved to New York?

GM: I thought I was just going to work in museums, work in galleries. That's how you work in the art world. I didn't think I could actually be an artist.

When I moved here I was working at American Apparel, interning at a gallery, working as an artist's assistant. Just doing all the things. Back then I thought, The Art World. It's so perfect. It's so amazing. I was desperate to be a part of it in any way I could.

As I started working in that world a little, I felt like, Oh, this kind of sucks. It wasn't what I expected, so that pushed me further to try to do my own thing. Before I moved here, my dream was to be represented by a gallery in Chelsea, but it's not anymore.

LG: What was the point when you realized you could devote yourself to your own work full-time?

GM: It's been about a year now, so I guess it was about three years of working a full-time day job while doing my own thing. I was really scared to do it for a long time because I was terrified of not being able to pay my rent, not being able to buy groceries. Probably three or four months before I quit my job, I felt insane; I was definitely working two full-time jobs, and I was having to say no to art opportunities.

My bosses at American Apparel, they were very great. They were very supportive. They would let me change my schedule last-minute. But it just got to the point where I couldn't be in two places at once. I just was like, "All right, you've just got to try it." It's been going really well so far.

LG: You also have a really big Instagram presence. At what point did you realize it was helping your business?

GM: With the clothing, a lot of it started with Lena's Instagram post. At that point, I was printing to order, and I'd get maybe one or two orders a week. After she posted it, I woke up to 40 orders. I realized how powerful it is, how much it directly drives sales. It's free marketing.

I'll post a drawing and just ask, "Should I put this on a T-shirt?" It's really important to me to know what the audience wants, what they respond to. I think the whole past year I've really tried to value that.

LG: What has changed the most now that you are running your own business?

GM: I have an LLC now, Art Baby Girl. I slowly got into it. Now I also have someone in LA that produces all my clothing and does all the shipping and customer service. Now I can focus on the creative stuff; I do clothing, but then I also do freelance illustration, and I'm also a freelance curator.

LG: Can you tell me a bit more about what you do as a curator?

GM: When I curate, it's like "Art Baby Gallery presents…," which I think maybe convinces people that it's more of a legitimate thing [laughs]. Ever since I was in college, I was drawn to analyzing other people's work, putting two pieces of artwork together and having them almost talking to each other. Those pieces can then have this new relationship and become this new thing.

I started doing art shows at Alt Space in Brooklyn, a gallery that was also a DIY space. I did three exhibitions there, and now I'm at the point where brands are hiring me to create an exhibition of young artists. It's something I'm totally still figuring out because there's a few other young curators, but I think it's still a thing that doesn't really exist that much outside of museums and galleries. I love to do it. I get bored if I'm just working on one project. It also gives me a chance to step outside of my work and what I'm making, which is important to me.

LG: Recently I feel like your work has definitely taken more of an activist stand. Can you tell me why that's important to you?

GM: I've always been outspoken about these things in my personal life, but I think I was worried. I didn't want to seem too aggressive; I wanted to be likable or something. I reached the point where I was like, Fuck that. I have way too big of an audience online to not use it responsibly. I think that's why I started to make stuff that was a little more in-your-face. I just felt like it was irresponsible of me to not use my privilege in a productive way.

I have a shirt with a cute bunny on it that says, "Fuck the police." Maybe it's silly, but I feel like cute things and humor can be used as access points for talking about stuff that maybe people are too shy or uncomfortable to bring up. Also a lot of activist apparel, the aesthetic of it is just not my thing. All black and white and block letters. It just is not cute to me.

This interview has been condensed and edited.

Laia Garcia is the deputy editor at Lenny.
 
 
 
 
 
The Woman Taking Barbering to the Next Level
 
 
Pope the Barber illustration

(Danie Drankwalter)

I'm in a Woodland Hills strip mall where Pope the Barber is cutting my hair as part of a sponsored seminar she's giving to about twenty women who were bussed in from as far away as Sacramento. They're watching her give me a taper fade with a Peter Coppola keratin treatment that everyone agreed was pretty dope.

Pope's entrepreneurship story could not be more typically all-American. At a young age she learned a trade and became a practitioner who required nothing more than the razors, shears, and pomades she could carry in a tool bag. She spent years working until she finally saved enough money to settle down near her hometown to start her own shop. And her skill is old school, too: I can attest that she is amazing at cutting men's hair and teaching others how it's done.

Pope's Instagram is 57,000 followers strong, and for all the face tattoos and photo shoots, what has made her a true success in this overcrowded influencer economy is her ability to create a truly original lifestyle brand. We discussed how she built her social-media following, how she got into the boys' club of barbering, and the hardest thing about running her own shop. It used to be that a celebrity hairstylist was someone who cut famous people's hair. But Pope is the celebrity now.

Ben Cooley: Let's start from the beginning. Where were you born? Who raised you?

Pope the Barber: I was born in Long Beach, California, and raised in Compton and Long Beach by my mom. I grew up in the hood, pretty much. I know my dad. He was kind of in and out. My mom and him are really good friends, it's just that they're both very strong personalities. Now they really respect each other. My dad is Cambodian, and he is a bodybuilder. Then my mom is a really strong Greek woman.

I've grown up against every social norm. I was introduced to and raised with both cultures. They are fresh-off-the-boat kind of people. Since I grew up in predominantly black and Asian communities, I guess people didn't really know how to take me, so it was a lot of proving myself constantly. In high school, I was known as the person who cut hair. That kind of made me accepted.

BC: How did you get into cutting hair?

PtB: I played basketball in high school. We would travel with the boys' teams. They would be cutting their own hair with clippers in the bathroom. I just thought it looked fun. They'd be in the mirror and I'd be like, "I can help you." They'd be like, "Nah, nah, nah." Before I knew what, I was the white girl who knew how to cut hair.

I was definitely self-taught in that way, but I ended up going to school for barbering after and made a career. There's a social-media culture behind it now, but I've always breathed barbering. I've always cut men's hair. When I first started cutting men's hair, I didn't know any women that had ever cut men's hair.

BC: Break down your business a little more for me. Do you have a shop?

PtB: Yes, I just opened a store in Santa Ana that's called the Vatican.

BC: Because you're the Pope?

PtB: Because I'm the Pope. Yes! I had a first shop and it got robbed from head to toe. We were getting our electricity done and our cameras put in. During that week that we were shut down, somebody went in and took everything.

BC: Everything? Oh my God.

PtB: I had a lot of business partners then. It was a loss for me, so I decided to go off on my own. This is Vatican number two, and this is my own solo project.

BC: Tell me how you promote Pope the Barber.

PtB: I come at it guerrilla style. On foot, on the ground. I have to be seen places pretty much. Of course you have to have something backing you up, and for me it's barbering skill.

BC: When you post images on Instagram, like of your girlfriend or the haircuts, are you thinking about your brand, or are you like, Fuck it, this is me?

PtB: A little bit of both. I do a lot of subliminal marketing through my pictures. For example, some of the sponsorships that I have, I promote them just through my lifestyle. That's what people want. That's why people endorse me. They just want me to live my life. Get a few pictures.

I know what time to post. I know when people like the most. I know who to blast if I really want to market something I'm coming out with. I'll definitely go to my other friends with a big following and have all them post it too. I know how to work that system for sure. If I'm posting something relevant, for example, shoes or anything like that, I'll make sure some big shoe brand, I'll post right after them so people are going one after another.

BC: When you started out, you were the only woman around. What is it like being in the ultimate boys' club?

PtB: I've grown up in it.

BC: It's just breathing the air for you.

PtB: Yeah, it is. It's tough, especially doing these guest-barbering spots. I'm in a different barbershop every week. I see what's up, and it was hard in the beginning being a woman. It goes back to I have to prove myself. I'm proving myself constantly in this industry.

But there are pros and cons. I say pros: Nowadays people want to be in a woman's chair. Some guys like a woman's touch. I'm that mix where I'm not wearing heels behind a barber chair but I'm a girl cutting hair. People like to see that. Some guy was telling me earlier that it's like a girl who likes football. You're just attracted to that or something. But, you know, I'm a lesbian, so people know that boundary. It's nice.

That's the pros of growing up in this industry. I'm not scared of confrontation with a man. I've almost gotten into fistfights in barbershops because of some stupid guy. I can handle my own.

But it's been tough. I remember getting it more six, seven years ago, men saying, "She's not going to cut my hair, is she?" I have my coworker over here telling the guy, "No, no, she's been cutting hair for a long time." It's like validating me, and I just don't need that.

BC: What's been the hardest part so far in running your own shop?

PtB: My business partner Aubrey and I went in on this together. She's an entrepreneur and loves the barbershop vibe and is one of my best friends. It just kinda worked out like that.

I have so many people offering me help. I am slowly learning how to take it and delegate some of my workload. I thought my life was hectic before, trying to get the shop open, but now that it is open, holy crap! It's a lot to handle and I've just kind of accepted that I'm not going to get a lot of alone time right now. I think the hardest part is not having more hours in the day.

BC: Do you see growing it at all? I look at Ruby's or Floyd's, those kinds of franchises. How do you compete with that?

PtB: It's funny, my old boss would try to put me down in a way [about franchising]. Anybody who left his side, pretty much, he would try to bring them down a little bit. When I was mapping out Vatican, he told me, "Oh, that's not franchisable at all. That's not franchisable." I looked at him, and I was just like, "What makes you think I want to franchise this?"

It's not all about the money for me. I don't even want a franchise. I'm glad it's not franchisable. I wanted it to be a one-of-a-kind thing. If this does well I do plan on growing, but I will be personally picking everything out and doing this myself. I learned with my first Vatican: With all that, it's better to just do it yourself. Nobody's going to carry out your vision like yourself. I don't mind putting in that footwork either. I'll jump from place to place, I'll get no sleep. I don't care, I want it done.

BC: When you manage a business that you own (especially one that is so much a part of who you are), do you find that your life becomes your work?

PtB: This is my life, man. It's a lifestyle. The passion is real. It's all intertwined and I like it that way. It's always been like that. It's always been for someone else's shop and vision, and now it's mine, so obviously there's more pride in it, but yeah, I enjoy it. It consumes me in a good way. I'm a very simple person. I like to cut hair, go to the gym, eat good food, hang out with my girl. The barber life is real.

This interview has been condensed and edited.

Ben Cooley is Lenny's CEO.
 
 
 
 
 
 
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