Tech Boss Lady

HOW TO USE THIS BOOK

THIS START-UP BOOK won’t be like the others.

I know what you’re thinking: “Real innovative, Adriana! Another start-up book!” Or maybe it’s something like, “Aren’t you supposed to be from Silicon Valley? Aren’t you supposed to do new things there?” Or maybe it’s just: “I’m confused. You say you’re Mexican, but you look Japanese. Which is it?”

This book is written for first-time founders around the world. First-time founders of any business. Tech founders. She bosses, they bosses, and he bosses. It’s for those of you who can’t stand reporting to someone else because you know deep down inside that you should be that someone else. It’s written for anyone who has ever dared to dream of the possibilities that lie just outside the margins of convention, the ones who itch to solve a problem and won’t stop until they’ve at least tried. It’s written for all of you whose hearts beat to define your own fates.

This book is written for founders of all kinds, but don’t get tripped up about the “tech” aspect. Frankly, you’re kidding yourself if you don’t consider yourself a tech founder. I don’t care if you’re in the business of fashion, pet-sitting, cosmetics, health care, lemonade stands, time machines, whatever. We’re all tech boss people. Every business today relies on technology to scale.

It’s also written for those of you who work in the start-up world as a non-founder and those of you who take charge in the corporate world. Start-up founding team members. Intrapreneurs. Tech workers. Just because you’re not at the helm of the ship doesn’t mean you don’t affect its course. The advice shared in these pages belongs to you, too.

This book is meant to show the real side of start-ups; the gritty underbelly of start-ups that so many people don’t understand until they experience it themselves as first-time founders. I want to discuss topics that make even the most veteran of founders uncomfortable, like failure, insecurity, and disappointment. I want to tell you what happens behind the shiny logos and before the launch events. I want you to understand the realities of what it takes to build something from scratch, forged from willpower, iron determination, and just enough ego to see it through—because it’s going to be harder than you believe, I promise.

But I can’t just use my story—that would be a disservice. I want you to also hear it from female leaders who have been there before us and survived—and the ones who are in the thick of it this very moment. That’s why I met with more than twenty badass female leaders in tech so I can deliver their war stories and sisterly advice straight to you. Learn from their challenges and experiences. Apply their advice to your own goals. My hope is that you close the book with a better understanding of what you’re about to get into.

Start-ups have a sexy appeal, but I want to show you what they look like in the squint of early morning light. Like what you might see after an amazing night out on the town and a one-night stand: no six-pack, off-brand briefs, back hair that would make a bear jealous. The stealth-farts infiltrating your silky bedsheets and the halitosis may make it hard to remember what was ever appealing about your choice in the first place.

Now, this isn’t to downplay the sexy side. Oh, the sexy side! I imagine it like the bright lights of a Broadway show. In fact, I often feel that way even today. Being your own boss, even being an “intrapreneur,” is the gateway drug of entrepreneurship. You’re holding the reins of your destiny, and the doors to any limitations—real or imagined—have been knocked down. It’s you and wide-open range, baby. Do What You Please Land. There, decisions flow freely, red tape doesn’t exist, and the stakes are high.

There’s an inherent adrenaline rush in the idea of being your own boss and breaking away from the safety harness a regular office job provides. Beyond giving corporate America a solid kick in the groin, you have the satisfaction that every minute you give to your venture is for you. Your dreams, your vision, your product, your name.

Yet. Few start-ups will become the next TechCrunch darling.

Here’s what you know, or think you know: You’re probably going to fail. You may never get funded.

I know this. Of course you do.

You’ve probably also considered the huge punch in the face your personal finances are going to take. Pasta and cheap beer every night, and cut the manis and pedis, you hear me?

Yeah, I’ve thought about that. Of course you have.

You’ve probably thought about the massive amounts of cash you’re going to need to make your dream happen. Taking checks from friends, family, strangers. The promise that’s made when you accept that money.

No shit, Adriana.

Well, it’s not enough. What you think you know—it’s not enough. It’s only going to take you so far before you get sucked into the start-up undertow. I want to warn you. To prepare you. I want to open your eyes so you understand what you’re walking into.

I wrote this book to tell you what it’s like to walk in a beat-up pair of start-up shoes. I wrote this book to put you inside the minds and hearts of founders, advisors, and experts across Silicon Valley, to share their stories and insights with you. This isn’t about flowery stories of inspiration (though maybe you’ll find some hope here). This isn’t about making you feel good (no one will care about your feelings). This isn’t a book of success stories or winning (though many people we’ve spoke with have found, or are on their way to, success).

It’s the story of what it really takes to pull it off. It’s the low points and high points of many people’s journeys. It’s the insights and anecdotes from Silicon Valley insiders on what they’ve experienced and what they believe is needed to survive start-up life.

And it’s the story of Girls in Tech. My story.

I want this book to get as dirty as real start-up life. I want you to rip out pages. I want you to scrawl in the margins. I want this book to get trashed at the bottom of your hipster San Francisco messenger bag. I want this book to bear the stains of your greasy late-night taco truck run. I want you to use this book as your personal stress ball, token of hope, and punching bag.

Because this shit is hard.

INTRODUCTION

LET’S KICK THIS party off with a flashback. Year: 1989. Location: Westlake Village, California, an idyllic community of three- and four-bedroom homes, vibrant green golf courses, and public schools good enough to make even the biggest private school snob give a begrudging nod of respect.

I’m twelve and experiencing puberty in all its glory. My features are playing a game of Ms. Potato Head with me; nothing seems to fit my face. I’m rocking a fuchsia tank top, a slap-bracelet, and roller-skates—the real deal, with laces. I’m at my mom’s travel agency in Oxnard, just north of where we live. It’s the weekend, when I can push myself around the foyer without worry of slamming into customers. Paula Abdul’s electric voice blasts from the radio. In a few minutes, my mom will hand me a stack of flyers, warm from the printer. It will be my job to skate through the grocery store parking lot and hit each car with a flyer advertising her travel agency services.

This was my first experience with entrepreneurship.

I didn’t grow up knowing exactly what I wanted to do. But I knew the kind of life I wanted. My parents set the example for me: my dad was a technical writer for Walt Disney’s Imagineering arm, crafting meticulous manuals on how to put together and fix each and every ride. Growing up, my dad was always around the house. I never wondered where he was, because he was always home. He asked about my day. I helped clean his office, and I filed his work papers. But it wasn’t all paper stacks and filing cabinets; in the afternoons we’d squeeze in one of our signature daddy-daughter burping contests. (My future boyfriends would learn that I belch better than a hippo.) These days were my earliest lessons in the concept of work-life integration; the idea that I didn’t have to separate the two has stuck with me ever since.

My mom immigrated to the United States from Mexico. She was one of twelve kids. She had few other choices in life but to hustle. After working for Mexicana Airlines for years, she discovered a far more lucrative career that still had all the perks of the travel industry.

So, she opened her own travel agency and rocked it. In fact, at one time she was doing so well that she made more money than my dad. It was a family business. My sister and I worked there on the weekends and sometimes after school. I was often tasked with creating my mom’s flyers and keeping the front desk organized.

I didn’t see my friends as much as I wanted to. But, as a family, we all understood that we worked together, and we took care of each other. Just like kids have faith in many things—their parents, teachers, Santa Claus, rainbows, the spooks under their bed—I grew up believing that if I worked hard, it would translate into the life I wanted. I didn’t receive a paycheck per se, but my allowance money was all I needed to grab a movie on the weekend with friends or to save it up for DVDs and CDs (remember those?).

I didn’t connect the dots between entrepreneurship and my roller-skating flyer girl persona until much later in life. I knew I didn’t want to be—couldn’t be—stuck in a corporate job. It wasn’t that I didn’t want to work hard; it was that I couldn’t stand the idea of being put in a box. Corporate jobs come with corporate job descriptions. There’s a chain of command, rules, a thick employee manual. Pay grades and volumes of HR stipulations that say you can only get this percentage raise a year, or that you can only make this much with this title. Even at a young age, these concepts felt claustrophobic to me. I couldn’t stand the idea that I could be hired to do one thing and limited in my ability to explore and do another.

Start-ups offer just the opposite experience, especially at a very early stage: there’s so much to do and so few to do it. Those who volunteer to take on extra responsibilities are heroes in this situation! Rules hardly exist. There’s probably no HR. Projects are up for grabs, and small teams can be nimble. Few people will tell you no if you want to test an idea or dive into a new project that isn’t in your original job description. All hands are wanted, ideas welcome, and duties negotiable. This made sense to me. It sounded far more appealing than being boxed into a stuffy pay grade or job title. At start-ups, I knew I could be just as free spirited and fast flying as my roller-skater persona wanted to be, tearing down the halls and getting things done.

It was settled. The corporate world wasn’t for me.

Some know early in their careers that they want to come to San Francisco and immerse themselves in its start-up ecosystem—arguably the best in the world. Me? I zigzagged my way here. After graduating from UC Davis with a degree in sociology and a concentration in organizational studies, I hung around LA for a year, working in marketing and advertising. I landed in San Francisco for a quick year to work for Chase Communications before returning to Los Angeles for an opportunity in consumer brand marketing strategy. Later, I moved to Miami to work for a real estate development company for nearly three years. And then a job for a worldwide PR agency brought me full circle back to San Francisco. But it was the next job, heading up marketing for an online video start-up in 2006, that made me stay. It took a few attempts to “stick” to San Francisco, but, once it happened, there was no way in hell you could rip me away.

I still feel this way today.

Now, about that start-up. It was an online video start-up—not the porno kind, the Netflix kind. It was truly cutting-edge, before its time. I had been poached from my ad agency to come lead the product marketing strategy. I breezed through the interview process, and I was ecstatic to get the gig. I had a big title. Good money. Real-world responsibility. I felt like a badass.

Here’s the deal. All the rumors you hear about start-ups and the stereotypes you hold—well, they’re true. I can verify it myself, as I walked into the cliché on my first day. Ping-pong table? Check. Shiny flat-screens with March Madness news bites scrolling nonstop? Check. A bunch of dudes making fart jokes? Check. (Okay, I may have gathered around the ole water cooler for that one.) But you get the idea. It was like walking into a man cave masked as an office. And I was the only woman, aside from a receptionist, at a company of thirty dudes.

There was no build up to it, no peaceful first few weeks. The harassment kicked off as soon as I received my company-issued Mac. The inappropriate e-mails poured in that fast.

You smell good. Gross.

I love what you’re wearing. Your ass looks great in that. This one made me want to crawl into a potato sack and call it a day.

What are you doing tonight? Uh, buying a Costco-size batch of pepper spray?

I even had a water bottle thrown at my head when I was on the phone with a reporter. (No, I’m not making this up. If I was, I’d think of something a lot more creative than water bottle abuse.) And it wasn’t that I couldn’t catch the damn thing; the mountain spring water came along with a refreshing side of, “Shut the fuck up!”

Rather than squash the issue from the get-go, management’s brilliant solution? Offer me a corner office on the other side of the building. Sure, I loved the kick-ass view of downtown. But it was a flashy prison and a shameful excuse for a solution to a pervasive company problem. I was isolated from my team, unable to collaborate. I might as well have been working remotely.

I realized I was working with a bunch of kids running wild on a playground. Welcome to the start-up world, Adriana.

Two things came from my experience there. One: despite the harassment bullshit, I still loved start-ups; I loved technology. It was the first time I was really in my element in a start-up post-PR job, post–real estate. A bunch of assholes couldn’t deter the sheer joy I experienced from building something. Playing a key part in the early stages of a company felt right. It’s profound to see a product come together and to know it’s from you and your team’s hard work and sweat. When you work around the clock and you get your hands dirty under the hood of a start-up, you earn a right to be proud. Look, Ma! I made that! Two: despite this incredible satisfaction, I realized I couldn’t be the only woman in tech who experienced a similarly unfriendly, sexist work environment. I saw that I was isolated, but I instinctively knew there were others like me, sprinkled at start-ups across the city, feeling just as alone. Apparently, a lot of women poop while giving birth. Whelp. My shitty experience led to the birth of Girls in Tech.

You know the saying, “find your tribe”? My initial mission was just that: find other women in tech. I had survived for a year and change at the video start-up. But, by this time, I was depleted. I was pissed. I was downright sad. I was supposed to be doing what I loved and working on projects that made me feel alive. But, instead, I woke up every day with a pit of anxiety in my stomach. This is a physical reaction to the anxiety that comes from being bullied and harassed at work, the place you spend most of your week. It was a year in, and I didn’t feel safe there. My body said so.

It was as though the veil had been lifted on something that I thought I loved and trusted. The tech industry was exciting, fast paced, and innovative—all the things that pulled me in like a magnet. But it was also rampant with sexual harassment and hostile toward women. If I was going to march on, I owed it to myself to build a support system.

So, I looked for one. But there wasn’t anything out there for women who were early to mid-career who just needed a support framework. Who needed to see that they weren’t the only ones going to work in a man cave every day, they weren’t the only ones passed up for that promotion, they weren’t the only ones receiving creepy new-hire welcome e-mails.

So, I did what every entrepreneur does when she stumbles upon a problem with no solution. I set out to create a solution myself. I spoke with friends about it. I went to sleep at night, thinking in hazy abstracts about what it could all become. Months passed until one Saturday, when I visited my fashion designer friend, Jeff, in his sunny studio apartment.

We snacked on sushi and stared out his floor-to-ceiling windows at the San Francisco skyline. In the corner of his apartment sat his drafting table. Strewn across it were colored pencils, paper, scrap paper with notes on them, samples of soft leather, his laptop. The tools of a modern artist. Seeing his sketches—the stick figures of women, the splashes of color, the messy and loving nature of his work process—inspired an instinctive urge to share my own aspirations.

“I have an idea,” I started.

“Well?” he raised said, eyebrows raised. Do tell.

“I want a way for women in tech to find each other. There’s more of us, out there. But we need to find each other. I was thinking of creating a group or putting on some events.”

“You’ve got to do it.”

Such confidence! For him, it was such a no-brainer. But that’s the way Jeff operates. Have an idea? Just get ’er done.

“I was thinking of calling it Girls in Tech,” I said. “It’s not for girls, it’s for women. I mean, I suppose it could be for girls. But I want it to be fun. I don’t want it to feel stuffy. I want it to be hip. I want people to be excited about it.”

He turned to his laptop and clicked on whatever design software he used at the time. In a matter of minutes, he whipped up a logo. The “Girls” he made cursive; feminine. The “Tech” was blocky and digital. And then he paused, briefly, before adding one last detail: a pair of eyeglasses hanging off the T.

That’s when things became real. That logo didn’t just represent an idea; it represented an organization. That logo carried Girls in Tech through its first few years. Having that logo in a file on my laptop meant something. It gave my idea shape; it made it feel official. In those moments, my idea went from being whimsical to having weight.

Eyeglasses on the T and all.

I must address the Girls in Tech name here, now, because I can’t let this book pass me by without taking an opportunity to do so. I get put over hot coals on the regular for the name of my organization. A lot of people have a problem with it being “girls” in tech rather than “women.”

When I started the organization back in 2007, I was hyper-focused on the fact that there didn’t seem to be any “cool” organizations for women in tech. I didn’t want to create something that rang of a lecture hall; I didn’t want to give the group a name that felt robotic or sterile or… well… not fun. Perhaps this was the marketer in me putting her foot down. To attract members and grow, I wanted women to know that we were relaxed, that you could come to our events and meet other “girlfriends,” and that it was going to be anything but stuffy. I think it’s fair to say the brand has held this standard since day one, when women came to our launch event in San Francisco and entered a club via a playground-style slide, for God’s sake.

We’ve grown up a bit (bye-bye, slides), and our events certainly raise the standard for grittiness and rawness. That’s the way we like it. That’s what I envisioned more than ten years ago, and I think that’s what women need and want. A no-apologies forum. Our speakers get up onstage and feel comfortable dropping an occasional F-bomb. Our events connect women—but not in a transactional manner; they’re connected because they find real joy in meeting other badass women in tech. The realness, the casualness about our programs has lent itself to a real community feel, one that I don’t think the word “women” would support to the degree that I’d like. Nope. I don’t want to be perceived as buttoned up. I don’t want to dull down our color and vibrancy. I don’t want to extinguish the youthful impression that our name evokes. That’s a light I only want to allow to shine brighter.

But. Women get angry that we don’t call it “women.” To some degree, I see where they’re coming from. Would men flock to an organization called Boys in Tech? Unlikely. But men also don’t refer to their buddies as their boyfriends. They say they’re going to go hang with “the guys.” I could go on, but I’ll leave it there.

Girls in Tech is all inclusive. We do have a handful of teenagers show up at our events, and we love that too. We also have men (dudes, boys, guys, whatever). My goal isn’t to diminish our maturity or our credibility or to lose supporters. I suspect that our members get it and appreciate the playful nature of our brand. We like to think that we speak with the energy and spirit of a girl, that all of us women members share a sort of girlish connection and fierceness.

So, armed with little else than my hastily made logo and gumption, my vague notion of “women connecting with each other” became Girls in Tech. It was 2007. It was springtime in San Francisco, and the fog was clearing, and the city air hung with optimism.

Ultimately, Girls in Tech launched with a single event: a networking night at a dance club downtown. I’ll admit, I didn’t go into the evening with a lot of goals, or even a lot of strategy. All I knew was there had to be other women in tech out there and they probably felt alone, like me. My goal: get us all into one room and have us step out from the shadows.

There was just one problem: I didn’t have the money to pull it off on my own. So, in typical Silicon Valley style, I pulled strings to make it happen. My friend Jonathan Abrams, founder of Friendster, was co-owner of a night club downtown called Slide. The club was appropriately named. One literally had to go down a giant slide to enter the place, like a twenty-one-and-over Chuck E. Cheese’s. The space was donated to our cause for free and from nine ’til midnight, Girls in Tech owned the dance floor. It was a deal I couldn’t pass up.

My marketing strategy? I used Facebook to get the word out, and I urged friends to share. I called every chick I knew and asked her to tell every chick she knew. Then I waited. It was me, my logo, and our first (humble) offering to the women of the San Francisco tech community. If you had asked me the night before how it was going to go, I would have told you I was wondering the same thing.

The day of the event, I was in heels in a city Target, struggling to push my shopping cart full of wine. With the bottles clinking and my heels tapping, I made my way through the store to check out. I don’t remember what wine I bought (lots). I don’t remember what cheese and crackers I bought from the grocery store after. But I recall a distinct feeling of optimism.

Flash forward to Slide, 9 P.M., I’m too busy cutting cheese (literally) to be nervous. I’m cutting cheese like I was born to do it and frantically opening bottles of wine. That was the deal: the space is free and you’re on your own for drinks, Adi. I didn’t want the women to have to worry about drinks; I just wanted them to show up. In the dimly lit background, a DJ spun the top hits of 2007, and, one by one, women slid into the club (how often can you say that?) to see what Girls in Tech was all about. It was only later that I learned that a long line of men formed around the block around this same time, just waiting for their chance to join us at midnight when our “freebie” time was up.

Here’s what happened while they waited outside. More than two hundred women showed up in their start-up uniforms of jeans and whatever else they felt like wearing that day. There was zero agenda to the evening other than giving women the experience of looking around the room and seeing that they were not alone. I’m sure I said a few words. Frankly, I was overwhelmed. It was a powerful evening, witnessing women coming together from all roles in tech and realizing that, yes, there is power in numbers. That night, something within me ignited. I had caught the attention of these women. It was time to make something real happen.

The potential at my fingertips was mind blowing. It still is today. In those early years, Girls in Tech focused on networking events and panel discussions. I leveraged connections at Stanford and Berkeley, and I called any VC I knew. We hosted presentations on fundraising and financial modeling and branding. Women collaborated and pulled each other up. Girls in Tech quickly launched in Los Angeles, then New York City, and soon after in Kuwait of all places! Turns out, women around the world are interested in technology. And they’re drained from fighting mobs of men to make it happen.

Nearly ten years later, Girls in Tech Kuwait is still thriving, with the same managing director who originally kicked it off. As for me, I now manage a team of eighteen employees and consultants. If it seems tiny to you, it’s huge to me, especially after being the solopreneur for so long. My baby is walking! Additionally, we partner with a talented team of freelancers and contractors. We keep things lean and scrappy. I primarily work in Girls in Tech’s San Francisco offices, but I also work wherever I happen to be in the world. Leading an international nonprofit takes me to all corners of the globe. I’ve logged into my laptop from Melbourne, Taipei, London, Barcelona, Paris, and back again.