#GIRLBOSS (15 page)

Sand Hill Road is the legendary venture capital hub in Menlo Park between Stanford University and Silicon Valley. The people who sit in those offices operate in a very different paradigm than I do, spending their days talking business models and IPOs in a way that I never will. It was strangely encouraging for me to come out of nowhere with instant respect from people I felt were an entirely different species. Some of them wanted to be friends and others tried to appeal to my edgy side (and FYI, “edgy” ranks right up there with “twerk,” “yummy,” and “ridonkulous” on my list of least favorite words). One investor left me a strange late-night voice mail and then apologized for it on the phone the next day. “Sorry about that,” he said. “I was all messed up on Percocet and Jack Daniels.” I’d be freaked out if a friend said something like that, so needless to say, I did not go with that firm.

It seemed most of the venture capitalists I met with had recently and unanimously “discovered” that women liked to buy things online. They were super-stoked on the idea of a female-run business that sold things to women. I happened to check a lot of the boxes that they were excited about at the time, but they had no idea why Nasty Gal was special. It was obvious to me that their ideas weren’t their own. One person asked to call my former COO, Frank, to talk about the business. I said sure, and gave him Frank’s number. I later found
out that he asked if I had a “spending problem.” When I heard this, I thought to myself,
Dude: I built a multimillion-dollar business out of $50 and no debt—does it look like I have a spending problem?

The only person I liked was Danny Rimer. Danny’s company, Index Ventures, was based in Europe and had just opened their U.S. office far from Silicon Valley, in San Francisco’s SoMa neighborhood, where the start-ups were. Danny had also already been investing in great fashion companies since before the other guys knew what fashion was—like ASOS and Net-a-Porter—so I knew that he was interested in Nasty Gal because he truly got us, not because we were the hot ticket. Danny had a brand—and I get brands. Index has chosen to surround itself with the best entrepreneurs and the best companies. I realized that, just as all department stores are not created equal, all investors are not created equal. Danny was my flagship Barneys.

After our first meeting, Danny called me and said, “You have a community. I get it.” And I knew it was a match made in heaven. He also seemed to inherently understand the challenges we were facing. At this point in time, we still didn’t have a head of finance, so we couldn’t answer half of the questions other firms were asking us. Danny recognized this. He didn’t ask us to go through due diligence (a term for digging through the company’s receipts and financials). Realizing that I’d never used PowerPoint, Danny also had an associate from his team put together an investment deck for me to present to the partnership. When it came time to negotiate, it was like
haggling at the flea market. He said, “I would like to buy X percentage of the company for X amount of dollars,” and I said, “No, X percentage for Y dollars.” And then we were done. It was a small investment—$9 million is not a small sum, I know—but it is atypical for a company of Nasty Gal’s size. Yet I was new at this and Danny knew it. Instead, he leaned in and suggested we shake hands on doing something small now with the goal of doing another, bigger investment if we both still liked each other in six months.

Had I not found Danny, I probably wouldn’t have taken investment. But his contrarian way of thinking, as well as his instant understanding of what I was building, made me love him. Index passes on investments that a lot of these guys drool over. I liked that. For Index, investing in a business is not just a mercenary transaction. Index wants to be involved and they want you to be exciting. They’ve passed on good financial investments because they simply didn’t like the entrepreneur. And I respect them for that.

What I really learned from this entire experience is that people want to invest in businesses that don’t need money, and that your ability to execute has to be just as strong if not stronger, than your idea. And, just like how I want to buy that item behind the counter at the vintage store that isn’t for sale, venture capitalists want to invest in businesses that also “aren’t for sale.” Human nature tells us to want what we can’t have. A desperate business is not a good look, and most investors won’t touch that with a ten-foot pole.

Even if you have no plans to ever find yourself sitting
across from a venture capitalist with a pitch in your hand, getting this far in #GIRLBOSS training should have taught you to rule nothing out. Perhaps someday you will have a business that’s the next big thing (I hope you do!), so it doesn’t hurt to be prepared. Here are a few tips for sparring with investors that you can also apply to other areas of your life.

Turn-ons:

Good people:
This is the number one thing that distinguishes one start-up from another. Investors, like employers, look for people who are excited about what they’re doing and have the integrity to keep their promises. They also want to see that you have a smart, creative team with diverse experience. The concept of “good people” should apply to every part of life. Surround yourself with people who are engaged, honest, and confident enough on their own quest to support you on yours. There is no time for losers.

Scalability:
Ultimately, the market, technology, fashion—whatever it is that is at the core of your business—is going to change, so investors as well as employers need to know you’ll be able to change with it. Or even better: Stay ahead of it. Most investors are looking to make a return of at least five to ten times what they invest, so you have to demonstrate that your company can achieve that growth.

Evidence of demand:
Have something that a lot of people are going to want. By the time I was talking to Index, we already had hundreds of thousands of rowdy Nasty Gals the world over, so it was very easy for us to prove that there was a more than viable market for our brand. When you’re applying for jobs, it’s best to be employed while doing it. You want the world to know that you’re not lollygagging between gigs, but instead have a lot of choices in front of you and are actively charting your own path.

Outside validation:
You can sell yourself all day long, but sometimes it’s more effective when other people sell you (aka your references). An investor is much more likely to be interested in your pitch if he or she has already heard about you because people are excited about what you’re doing. Great references (or a glowing introduction) never hurt.

Uniqueness:
This is where it comes down to your idea and how good it is. Taking someone else’s idea and adapting it for a different demographic isn’t really an idea, so good luck finding someone to invest in NastyGuy.com, your idea for a site that sells badass clothing to dudes. In whatever you do, you’re not going to stand out unless you think big and have ideas that are truly original. That comes from tapping into your own creativity, not obsessing over what everyone else is doing.

Turnoffs:

Overconfidence:
You need to be passionate and excited about what you’re doing, but don’t be so blinded by it that you’re unrealistic. If you’re saying things like “No one has ever done this before,” it usually just comes across as cocky or, worse, uninformed. As a #GIRLBOSS you should always be confident—and absolutely sure—about what you know, but humble about what you don’t.

Talking about how soon you plan to exit:
This might work for some people, but most investors are in it for the long haul. It’s for the same reasons that I don’t like it when I ask people where they want to be in two years and they answer that they want to own their own fashion business. People like to see evidence of commitment.

Typos and general unpreparedness:
Yeah, this is just basically a turnoff for anyone, everywhere.

PORTRAIT OF A #GIRLBOSS:

Jenné Lombardo, Founder of the Terminal Presents; theterminalpresents.com (@JenneLombardo)

I get my hustle on every day. For me it’s family first, paper second. Growing up, I always wanted to have my own office—I thought that epitomized success. I also always wanted something that was mine. Something that was tangible, which I could look at and say, with pride, “I did this.”

When I was growing up my family lost a lot of our money and I was forced to go get it on my own. My work ethic is partly fear-driven—I never want to be without financial stability again. Also, I want to be on
Fortune’
s
“40 Under 40” list. (I’m too old to make
Forbes’
s
“30 Under 30”!) I feel like I take risks every day, and the biggest risk I take is on life. Without risk there is no reward and no change. How boring would this world be if there weren’t people out there like Rosa Parks, Richard Branson, Bill Gates, and Steve Jobs? There are two types of people out there—those
who do and those who don’t. If you are a risk taker, you have to feel comfortable in knowing you could fail. You have to have enough confidence and conviction to go full force even if things don’t work out. For us risk takers it’s an occupational hazard. If we fail, we get right up and try again. Just doing is reward enough.

I am creative in almost every aspect of my life, particularly when it comes to solving problems. Whether we chose to believe this or not, there is a solution to everything. It’s all a matter of perspective and how willing we are to be flexible when it comes to our point of view. I don’t see things the way a trained eye would. In fact I question everything—how can I make this better, how could we be operating at maximum efficiency? It’s a blessing and a curse. Challenging convention and not accepting the norm is a world I have come to live in. I read everything and I ask a lot of questions. You won’t get anywhere just talking about yourself. Listen. It’s one of the greatest gifts you could give to yourself.

I’m constantly inspired by everyone I work with and the tribes we assemble. I am inspired by youth culture. I love knowing everything—what they are wearing, what they are listening to, what apps they are using. Kids are the future. If I wanna stick with the future, I gotta stay close to the game.

My advice to #GIRLBOSSes is: Create your own job. Become the master of what you do. Fully immerse yourself in your culture. Be humble: You are never above having to pack boxes. Never forget where you came from. And always be polite. Good old-fashioned manners can get you very
far.

Creativity in Everything

Every child is an artist. The problem is staying an artist when you grow up.

—Pablo
Picasso

A
t age three I was a speaker. When music played through our living room stereo, I stood in the corner like a statue with my mouth open, pretending the sound was coming out of me. At age four I was a camera. I took pictures with my eyes. I framed my photo within my vision and blinked my eyes to snap the shutter of my memory. Since that time I’ve been impersonating inanimate objects at every opportunity. But don’t call me a wallflower.

Early experiments in selfie photography and top hats.

My creativity began to crystallize as a teenager, when I got my first camera. At age eighteen I got hit by a car while riding a borrowed bike to dumpster-dive for bagels. That sucked but I got enough settlement money out of it to take
myself to Portugal and Spain (I spent the rest on an electric guitar). It was on this trip that I became obsessed with seeing the world through a lens—and returned home with more excitement than ever for photography.

Armed to Bless

A picture is a secret about a secret, the more it tells you the less you know.

—Diane Arbus

Soon after my trip abroad, I enrolled in full-time photography classes at City College of San Francisco, where I learned to develop my own negatives and expose my own prints. For our final project we had to shoot a series of some sort, and I decided on a Russian Orthodox Church down the street from my apartment. The building was tiny, and from the outside you could hardly tell it was a church at all. It was the architectural equivalent of a loner.

I felt a kinship to this humble outsider church in the middle of San Francisco’s metropolis, so I knocked on the door and asked Mother Maria, the nun who lived there, if I could take some pictures. I grew up Greek Orthodox and still have an appreciation for the sights, sounds, and scents of the faith, which I think helped gain Mother Maria’s trust. It turned out that she hadn’t grown up Orthodox but had chosen the faith. My conversations with her were pretty powerful—I knew so many people who had dropped out of society in so many ways, but here was a woman who had looked the world in the face and decided, in the purest way possible, that she wanted none of it.

Mother Maria was a badass.

The Russian Orthodox faith eschews any sort of luxury, which means the entire service is spent standing. In Mother Maria’s view, the world outside the church—which she called the “worldly world”—was a place full of gluttonous distractions that kept us from discovering our true spiritual selves. She invited my worldly self in nonetheless, allowing me to photograph her and the church. The photos didn’t turn out that great; I still had a lot to learn.

A few weeks later, though, Mother Maria called me. The old priest had died and she wanted me to photograph his funeral. When I arrived his body was near the altar in a simple casket handmade from a few pieces of wood with a white satin sheet stapled to the interior. Aside from me there were about eight other people in attendance. So many of the worlds that I had dipped into played at shrugging off modern society, but the priest was a man who had truly rejected it. In a city full of noise, he’d found light by living in the shadows. Holy shit, is that heavy.

My baptism by fire helped me to find comfort in many different environments. I photographed truckers, bartenders, and outsiders in Nowheresville. I had begun to feel like I really knew what I was doing with a camera. And I’d upgraded to my twenty-first-birthday gift, a Hasselblad medium-format camera. That camera, to this day, is the best gift I’ve ever been given. It was my mother’s last effort to help me find my way. I decided that I wanted to attend the San Francisco Art Institute. In order to do so, I needed to have a finished photography portfolio.

In order to fulfill this prerequisite, I chose to return to the church. Mother Maria introduced me to a priest, Brother Eugene, who lived on a small plot of land outside Santa Rosa, selling his vegetables at the farmers market on weekends. I spent the day with him and we talked about everything under the sun. He fed me trailermade borscht and I went on my way. I then set off to a Russian Orthodox monastery in Point Reyes.

The monastery was one of the most beautiful places I have ever been. There was a shipping container where a young monk spent his days dipping beeswax candles to be used in churches and sold in gift shops. Some men built caskets. Some gardened. They were shut off from the world but they were open enough to let me in. I couldn’t help but think that when they weren’t wearing robes, I could have mistaken these guys for metalheads.

In the end I decided that I couldn’t stomach the $50,000-a-year tuition and chose to forgo art school. But my series, which I called
Armed to Bless
, was an education in itself: It was one of the first times that I had ever finished something that I set out to do.

Find Your Framework

Applying to SFAI gave me the framework to be free within a set of rules in a way that school and jobs had not allowed me.
Armed to Bless
was an accomplishment beyond just taking pictures. It taught me that when I do things because I want to do them, and not because I have to, I can accomplish a lot. This type of framework is all around us and it also exists outside applying to or attending school. When it came to starting my own business, I found the framework that I needed on eBay. I probably could not have built a website of my own at that point, but my ambition grew with each crack of opportunity. The framework of eBay presented me with a series of easy-to-complete tasks (take photo, upload photo, write
description) that eventually added up to a business. Starting it was as easy as picking a name and uploading the first auction. That instant gratification would never have come had my first step been to write a business plan. And without that instant gratification I might not have kept going. If you’re dreaming big, #GIRLBOSS, don’t be discouraged if you have to start small. It worked for me.

Putting the “Art” in Sandwich Artist

Curiosity about life in all of its aspects, I think, is still the secret of great creative people.

—Leo Burnett

Anything you do can be creative. If, when you make a smoothie, you try to make the best smoothie the world has ever tasted, it’s a creative act. If you throw a frozen banana and some yogurt in a blender and hit puree, well, not only is it uncreative and boring, but I also feel really bad for you.

I was always looking for ways to make my job creative, no matter what that job was. At Subway I loved the giant spray nozzle that hung above the dishwashing sink. Blasting mayo off of the spatula was uniquely satisfying. I liked making bread, spacing out the little twisted sticks of dough into perfect patterns on trays before sliding them into the oven. I learned the secret to the perfect doughy center in Subway’s cookies: slamming the tray down on the counter, causing the cookies to spread out while the pan was still hot. And any job
that pays you for slamming things . . . well, consider yourself lucky.

None of the jobs at Nasty Gal are shitty to me, and I know because at some point I’ve done almost all of them. Whether it was styling, directing models, steaming clothing, or shipping an order—they were all creative. And when something got really boring, I turned it into a game to see how quickly, efficiently, and accurately I could get the job done.

The Venn Diagram of Creativity and Business

Access to talented and creative people is to modern business what access to coal and iron ore was to steelmaking.

—Richard Florida, author of
The Rise of the Creative Class

I would never have accomplished what I have had I felt forced to choose between my creative talent and my business acumen. At Nasty Gal, I’m the CEO and creative director, two titles that are rarely on the same business card—but what no one seems to talk about is that business
is
creative. I’m as creative when I’m choosing an investor as when I’m reviewing collection samples. I have as much fun hiring people as I did with a camera in my hand.

Keeping the Nasty Gal brand consistent as we have grown has been one of the biggest challenges I’ve faced. I’ve gone from being a solo artist to one part of a killer band. Our C-level team is the rhythm section, the rest of the team is
playing guitar and keys, and I’m just scatting.
Be-bop a doo-wa
 . . .

It wasn’t too long after I’d launched the eBay store that I started to recognize how important the thumbnail photos were. Thumbnail photos are prime real estate in e-commerce—they hook your customers in while simultaneously informing them about what they’re looking at. These thumbnails can’t be too messy or too bland. They must display the items clearly so that as prospective customers zoom quickly through the catalog page, they know what they’re looking at and also find it interesting. I saw that when the shape and style of an item was clearly visible in even the tiniest photo, it inevitably went for a higher price than a thumbnail where the silhouette was obscured or confusing to look at.

To this day I blur my eyes when I edit photos. I load all my photos on Bridge, shrink them down super-small, then cross my eyes like a goofball and flag the images that still catch my eye. This allows me to edit quickly without getting distracted by the details—if the composition or silhouette sucks, it doesn’t matter what the model’s face says. The DNA of a successful image, and brand, must be encrypted into its tiniest representation while gracefully telling the same story in its largest incarnation. My thumbnail photos were the postage stamps to Nasty Gal’s success.

I was used to making dozens of little creative decisions every day, but designing the first Nasty Gal website was my first macro “branding” project. Though once again, I didn’t see it as a branding project—Nasty Gal just needed a
website, so I made one. I had no formal graphic design training, but knew what I liked and what I didn’t, and had spent so much time observing and talking to my customers—through eBay and MySpace—that I was confident I knew what would appeal to them.

Block type was really big in 2008, so I found some clunky font on a German graphic designer’s blog and downloaded it for free. I smashed the letters together, making one solid shape, and the first Nasty Gal logo was created. I went through a million iterations of the site, but it was always a fairly simple design. The color scheme was always pink, black, and gray because I didn’t want it to be too heavy. I used a close-up shot of my friend Dee’s face in the navigation (Dee was an early eBay model and now works for Nasty Gal as an apparel designer) and it was up there for years. The main tenets of the navigation were “Shop New” and “Shop Vintage.” It’s not as if I invented the English language here, but Nasty Gal was definitely one of the first websites to sell both new and vintage and position it as such.

I knew how to use Photoshop from editing photos, but I did not know how to use InDesign, so I designed Nasty Gal’s first website entirely via Photoshop. Also, as I was self-taught, I didn’t know any shortcuts. I moved everything one pixel at a time. I must have spent hours hitting the arrow key, like
doo doo doo doo doo doo doo doo doo doo doo doo doo doo doo doo . . .
okay, now that box is halfway to where I want it to be, so . . .
doo doo doo doo doo doo doo doo
 . . . You get the picture. When Cody, who helped with the site
development, showed me that I could hold down the shift key and move something like ten pixels at a time, it was as if the heavens opened up, the angels sang, and I got back several hours, maybe even days, of my life.

I have always been an observer. When I see music live, I like watching not only the band but the crowd as well. What are their favorite songs? Who’s a fan and who has never even heard this band? Where’s the obligatory fifty-five-year-old man with no rhythm who arrived alone and is louder than anyone else in the room? Currently, I am always trying to imagine things from the customer’s point of view. Now that Nasty Gal’s creative decisions are made by our creative team, they have to look at things from three views: their own, the customer’s, and mine. Thank God I hire brave people, because the inside of my head can be pretty weird sometimes.