Special Characters

My Adventures with Tech's Titans and Misfits

Laurie Segall

• Publisher: Dey Street Books
• Year: 2022
• Print ISBN: 9780063016446
• eBook ISBN: 9780063016460
• Topic: Media & Performing Arts
• Subtopic: Journalist Biographies

"CNN's former senior tech correspondent shares her front-row seat on the rise of Facebook, Twitter, and other new-media empires—and the geeks turned entrepreneurs who founded them."—People

An unflinching, era-defining story of self-discovery and breaking barriers by award-winning investigative reporter Laurie Segall. 

In 2008, 23-year-old Laurie Segall was a newly minted assistant at CNN and was living in an East Village walk-up apartment. As Wall Street was crashing down, Segall began discovering a group of scrappy misfits who were rising from the ashes of the recession to change the world: the tech entrepreneurs.

A misfit herself, Segall gained entrance to New York’s burgeoning tech scene, with its limitless cash flow and parties populated by geeks-turned-billionaires. Back at the news desk, she rose through the ranks at CNN, while these entrepreneurs went from minnows to sharks, building companies that would become our democracy and our social fabric: Facebook, Twitter, Instagram, Uber, Tinder.

Over the course of a decade, Laurie Segall became one of the first reporters to give airtime to many of these founders—from Mark Zuckerberg (Facebook) to Jack Dorsey (Twitter) to Kevin Systrom (Instagram) to Travis Kalanick (Uber)—while tracking their evolution and society’s cultural shift in the CNN startup beat she created. By the end of her tenure at CNN, she had become its on-air senior technology correspondent and had witnessed the rise of second-wave tech, from the boom to the “complicated years” to the backlash, as her misfits emerged as some of the world’s most influential leaders.

A coming-of-age narrative chronicling an era transformed, Special Characters is, at its core, a young woman’s origin story—in love, in career, and in life—and an account of the humans behind the companies that have shaped our modern society. Filled with emotional heft and razor-sharp observations, Segall’s empowering memoir is a richly rendered backstage pass to the tech bubble that reimagined the ethos of our social, political, and cultural experience.

“Fans of Brotopia or anyone who wants a backstage pass to Zuckerberg and some of the biggest co.’s of our time, you’ll devour this.” —The Skimm

Chapter 1

Showtime

Ma’am, are you okay?”

The cop had pulled over and his partner rolled down the window.

Maybe it was my heels. I must have been wobbling as I walked across Second Avenue. At five-five, I’m committed to wearing at least four inches, but that doesn’t mean I do it gracefully.

The streets, which were usually filled with herds of NYU students bouncing between East Village bars, were now empty.

I glanced at my iPhone as the driver of the police car cut the engine.

It was 4:03 A.M. on August 18, 2008. My twenty-third birthday.

I adjusted my white-collared button-up that I’d deemed appropriate attire for anything professional and gave my best smile to the baby-faced cop and his older partner.

“Oh yeah, I’m totally fine!”

I was far too enthusiastic for this time of day. My body vibrated with the kind of energy you have before the years tick by and the circles under your eyes deserve their own nicknames. The kind of enthusiasm the policemen would surely deem a cover-up for a twenty-three-year-old trying to appear sober.

“It’s a bit early to be walking here,” he said. “This isn’t a safe area for a woman alone, this time of the morning. Do you need a ride?”

I wasn’t sure how true that was. The East Village seemed like a pretty safe place, even at 4:00 A.M. A part of me doubted whether I would’ve found myself in this same scenario had I not been a young white woman, making her way to work. I hesitated. Should I ride in the back of a cop car or wait for the subway?

After a bit of mental calculus, balancing the subway or a free ride, I climbed into the back seat.

“Fifty-Eighth and Eighth,” I called.

“So, where’re you headed this early?” the younger cop said, looking in the rearview mirror.

“It’s my first day on the job.” I paused. “At CNN.” It was the first time I’d said it. I let the words linger in the air.

“Fancy!” the older cop barked, winking, then taking a swig of coffee.

I grinned. I didn’t tell him it was a tentative position as a freelance news assistant. And I certainly didn’t tell him that my biggest accomplishment so far as a budding journalist had been getting a toe in the door. It involved every skill I had—tenacity without being annoying, creativity, and above all, scrappiness. I’d been working toward this moment for a decade.

As the police car came to a stop, I thanked the officers and exited to a lightening sky. The sun had yet to rise on the postcard view of Central Park; the streetlights danced across the buildings. It wouldn’t be long until the scent of vendors selling honey-roasted nuts and coffee for morning commuters filled the air. I took in a deep breath and looked around at the quiet streets, listening to the yellow taxis cruise by. As I walked through the revolving doors of 1 Time Warner Center, I felt like I was walking onto a movie set, complete with opening credits to my own life.

Inside the building, everything was dark and marble, and in the early hours, completely silent, apart from the clicking heels of rushed producers making coffee runs before the morning shows began, entering and exiting seamlessly with electronic badges. The security guards sat in an authoritative row near the doors and one of them noticed me stalling near the turnstile.

“Miss?” he said, looking over, his eyebrow raised, his demeanor questioning how I’d made it into the building.

“It’s my first day!” I said with unchecked enthusiasm.

He grunted and pointed me to another guard, who ushered me to the seventh floor. There, yet another guard who didn’t share my enthusiasm took a snapshot of me smiling too widely, adjusting my collar in time for the flash.

Then I was shuttled back down the elevator to the fourth floor, where dozens of desks dotted the open newsroom, cameras stretching their necks like giraffes hovering over the jungle of tangled monitors and blinking screens. Day or night, the newsroom was a labyrinth of incoming feeds, lights from the control rooms flashing on and off. Edit bays, where TV segments were cut to be later aired on shows like Anderson Cooper 360°, lined the hallways.

I’d spent the last week researching the producers I’d be working for, the ones who’d reported on 9/11. They were the hard-nosed journalists who ran toward the buildings, risking their lives to relay the news, documenting the horror of that day almost seven years ago. I had scrolled through YouTube videos, listening to their voices stating the facts. I studied their names, pressing pause and play over and over again. They were the real deal, and I was entering their bullpen. I’d be training under the best.

I took a seat and waited with a handful of other freshly minted news assistants. Despite my excitement, I knew where we stood. We were freelancers, entry-level nobodies with a one-year trial period to impress the right people, or else get out. I knew I’d have to find a way to make myself stand out in a sea of ambitious journalism hopefuls who’d made it this far. With relentless work, the right advocates, and perfect timing, I’d have a shot at a full-time position.

As the others exchanged tips and small talk, I sat silently, watching as producers stalked in and out of the newsroom, reporters marched around in their heels, and desk managers barked orders into their phones. I felt both terrified and like the luckiest person in the world.

Chapter 2

Wrecking Ball

My path to the newsroom started in middle school, the awkward and uncomfortable years when we have yet to settle into ourselves—the years we’re told we’ll grow out of. I was a pudgy preteen in an oversize flannel sweatshirt draped over khaki pants—the ones big enough to hide my discomfort in my own body, and the insecurity that came along with that.

It was a bright autumn morning when my mother sat my brother and me down on the pinstripe couch and told us that our father didn’t love her anymore. She closed the curtains, and a new era began. It was painful, and I struggled to adjust to the unsteady new family dynamic, one where my father was no longer an everyday part of my life and my mother was grappling with a broken heart and the anger that now filled our home. Our gray wooden house at the top of a long driveway in the leafy suburbs of Atlanta had a shadow cast on it. I retreated into my journals, where I wrote about the battles happening under our roof, stories about strangers, and suburban observations. I poured myself into the act of writing, filling worn notebooks with song lyrics that resonated with the isolation I felt. I held tightly to my friends’ families, to their warmly lit homes full of laughter and home-cooked meals.

In the meantime, my mother tried to comfort us by taking us to a suburban mecca: McDonald’s.

We went at least once a week, my mother trying to help us feel normal, to give us something to look forward to. During this time, McDonald’s introduced a new promotion: if you supersized your order, you could play Monopoly. Dutifully, we supersized our fries and sodas, peeling off the thumbnail-size playing pieces, hoping to win a prize or get a monopoly. As in the real game of Monopoly, everyone wanted Boardwalk. It was the most expensive property, and if you got that royal-blue tab, you could win a million dollars.

Within a year, I’d gained fifteen pounds and was one card away from a million dollars. All I needed was Boardwalk. The quest became my escape from reality—from the snobby suburbs of Atlanta, the divorce, the pain, and the overwhelming desire to fit into a world that seemed carved out for other people.

Perhaps if we had a million dollars, my mother wouldn’t worry about our shifting financial reality. If we were to achieve Boardwalk, the cruel middle schoolers on the bus, whose mothers refused to accept mine into their stifling circles, whose worst weapons weren’t their sharp words but their general disinterest, would pay attention to me. If we won the game, maybe my father would call more frequently.

I was a “good girl,” not by choice, but by instinct. Instead of staying out past curfew and dabbling in mischief, I felt a responsibility to be my mother’s “plus one,” to stay by her side and take on an adult role that included emotional support. My father, despite being a well-loved doctor, bristled at my anger. His new home was on the other side of town, but it felt like the other side of the country. Our family collectively ached, all of us unable to fully process the pain, manifesting in choose-your-own-adventure coping mechanisms, most of them unhealthy: Class photos with tack holes stabbed through the eyes. Doors slammed, and fingers and hearts broken. Our house, once filled with nightly piano recitals and spaghetti and meatball dinners, was paralyzed with anger.

I remembered my parents touching only once, years before. I’d held it with me, playing it over in my head like a song on repeat. My mother and father were driving me and a friend to the movie theater. We sat in the back of our white minivan, chattering as the car filled with music. Frank Sinatra’s “The Way You Look Tonight” began playing. My father looked over at my mother, his mouth creeping into a warm smile, and placed his arm around her shoulders. When she beamed back at him, I knew this was their song.

Now the music was replaced with muffled rage. As chaos swirled around me, I felt invisible. But I always held on to the hope of something better—of Boardwalk. Something better was just one meal away. Somewhere around the corner “spectacular” existed. A life where tight-knit communities in the beautiful green suburbs were nonjudgmental of broken families, where holiday dinners had five types of pie and heaps of laughter, where I wasn’t numb, and scared, and invisible—where anything was possible.

I cried myself to sleep when my brother went to boarding school, far from our chaotic home. I dug half-moons into my palms when I transferred to a new school in hopes of branching out from Holy Innocents’ Episcopal School, a southern, conservative high school where I was one of the only Jewish girls. No matter how much I had tried to fit in, I stuck out; I didn’t have blond hair or blue eyes or parents who owned part of the Coca-Cola empire. When one of the boys told me I was going to hell because I didn’t believe in Jesus, I laughed reflexively and shrugged, wondering if there would ever be a place where I didn’t have to try so hard to laugh off the feeling of being an “other.” I was uncomfortable in my own skin, in my tiger-striped retainer and frizzy hair that wouldn’t stay behind my ears.

But transferring to a new school, I felt even more invisible than I had before. The “nice Jewish girls” my mother told me about avoided eye contact. Our imperfect family wasn’t warmly welcomed in those circles.

Within a year, I transferred back to my old school, this time making my own space. Instead of attending tailgate parties, I listened to ska bands and drove myself to the Roxy Theatre in Buckhead, a short drive from my home. There, I’d watch string-cheese-thin musicians drape themselves over guitars and sing stories about another world. CDs by Reel Big Fish, RX Bandits, and Something Corporate were strewn about my used white Ford Explorer. I’d blast “Punk Rock Princess,” windows down. In reality, I was far from punk rock, and even further from a princess.

At sixteen I became managing editor of the student newspaper. I had opinions on everything and penned op-eds on why gay people should marry and a particularly blistering piece on the insensitivity of the county fair’s bouncy slide, which was in the shape of the Titanic. But I spent most of my time writing a column called “Spotlight,” where I had the opportunity to profile whoever I wanted. Being one of the least athletic students no matter the sport, I came to know the sidelines. So instead of writing profiles of the sports stars, I interviewed those behind the scenes.

Coach Red, the track coach who was well into his eighties, was tall and had kind eyes. It had been many decades since he’d run a lap and the other kids laughed when he tried directing sprints. During our interview, we sat atop the mats in the corner of the gym, and I asked him questions that I’d scrawled out in my notebook. He lit up when he discussed meeting his wife decades before and fighting in World War II. It was the first time I experienced the “light bulb moment” in an interview: that moment when the curtain falls and reveals something about a person that changes your point of view. As we were nearing the end of our interview, he opened up about his struggle with Parkinson’s disease. Under the lights of the basketball court, he started crying. He talked about living the rest of his life knowing what it would be like to die soon. The man people snickered at as he moved slowly, directing runners like a sleepy cop at a traffic stop, was gone. In front of me was an inspiring human who’d fought a war, found love, and was now beginning a new battle, staring at his mortality. The conversation was raw, it was real. His words were the most meaningful thing anyone had ever said to me.

So what if I can’t run a lap? I want to tell these kinds of stories for the rest of my life. And so, for the last two years of high school, I used my news...

Table of contents

• Cover
• Title Page
• Dedication
• Contents
• A Note from the Author
• Prologue: The Lobster
• Chapter 1: Showtime
• Chapter 2: Wrecking Ball
• Chapter 3: The Bullpen
• Chapter 4: Fake It Till You Make It
• Chapter 5: Finding My Superpower
• Chapter 6: The Pleasure of Business
• Chapter 7: Professional Stalkers
• Chapter 8: Values and Valuations
• Chapter 9: Sex, Love, Silicon Valley
• Chapter 10: Bits & Bytes Meet Flesh & Blood
• Chapter 11: Getting to Yes
• Chapter 12: Mostly Human
• Chapter 13: Going Live
• Chapter 14: Murky Territory
• Chapter 15: Bugs in the Software
• Chapter 16: Mission Impossible
• Chapter 17: All Hell Breaks Loose
• Chapter 18: McScam
• Chapter 19: Boardwalk Is Within
• Epilogue: Dot Dot Dot
• Acknowledgments
• About the Author
• Copyright
• About the Publisher