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12. Funnel of Winners

12. Funnel of Winners

This is the twelfth chapter of “Scammer,” a serialized novel about ambition, fame, and influence in the age of the Internet.

Money, power, glory, fame.

Why is it that a tiny minority of the population gets the majority of these societal rewards? The very idea that someone could be both rich and famous, rich for being famous, powerful for being rich seems like the height of unfairness. Leave some for the rest of us poor fucks! I would think in middle school as I flipped through a biography of Taylor Swift, insides churning with envy as I read about her influence in the music industry, her multiple accolades, her legions of ardent fans. She’d been a normal girl from Pennsylvania once, too — what was so special about her that she’d gotten to be a superstar while I seemed doomed to a life of mediocrity?

Then I started paying attention to how people I admired had gotten to where they were. A pattern started to emerge. It was simple, really: an important event — a big break — happened that raised their status, which would then cause another important event to happen, which would raise their status further, and so forth. 

Sometimes people engineered that big break, some were lucky, and some people got their big break as soon as they were born. Taylor Swift convinced her entire family to move to Nashville when she was fourteen to increase her chances of getting a record deal. Marilyn Monroe was discovered by a photographer while working at a munitions factory. Stella McCartney was the daughter of famous musicians. But once that first event happened to them, they started attracting more and more big events. They’d gotten into the funnel of winners, which enabled them to keep winning and winning.

I’d … well, I’d cheated my way into the funnel by buying fake engagement for my Instagram account. Once I had enough social proof, real people started following. That large following convinced Oliver to agree to a fake relationship with me, which got media outlets to write about me, which landed me my book deal.

Everything cycled upwards. The famous got more famous, while the nobodies faded into obscurity. It was kind of fucked-up, if you thought about it. I just preferred not to think about it too much.

— A staged shot of me and Wren shaking hands in front of the giant metal F in the Falcon Ibis lobby: I just signed with my DREAM literary agent, Wren Falcon! Famous clients of his include Marnie Tucker and the author of “Make America Gay Again.” I’ve had my eye on Wren for years. He’s the agent I’ve always imagined working with on my first book, and now that’s going to be a Thing. Can somebody please come slap me across the face? I clearly need to wake up.

— Me standing in front of a turquoise background with magenta orchids in my hair, holding my phone and smiling mysteriously at the camera: It’s coming! A full year of writing for you and this is the first time you will be able to hold my words! Ever! The goal of this book is to make a pretty object that you can hug and display and cherish, while also giving you an escape hatch from your life, like all good authors do. On Instagram you can disappear into the coziness of my writing voice, but only for so long. Captions are done in a hot sec. With AND WE WEREN’T LIKE, we can finally hang out uninterrupted, just like real-life best friends do. Let’s fucking go!!!

Oliver had gotten into the funnel of winners, too. In January, NipNop raised a $13.5 million Series A round led by Bret Manson of Yardstick Capital. Practically, this meant that it had to grow as a company, to expand its teams and product offerings and stop operating like a scrappy startup. In reality, it meant that Oliver’s and my joint stories of getting our heroes to work with us were too cute to resist. Invitations for interviews and talks and parties poured in, each more impressive than the last. TechCrunch! Ted! Vogue! I had been spot-on when I’d told Oliver that people loved power couples. Who had time for work when hype was calling?

— Me and Oliver on the cover of The 1337, posing back-to-back like buddy cops: My dream of being culturally relevant has finally come true.

— Me in a white dress, sitting on the Andy Warhol Bridge in Pittsburgh: When the editor of a well-known entrepreneurial magazine asked me and Oliver if we were interested in attending a party for entrepreneurially-minded individuals under the age of 30, we were like “sure!” What we did not know, however, was that this party was in Pittsburgh, Pennsylvania, a full SIX HOUR FLIGHT from San Francisco. Oh, and that Pittsburgh was still FREEZING at this time of year. No problem to both: Oliver got the magazine to pay for our flights, and I warmed up before the party by climbing halfway up this bridge. Did you know that this bridge, named after Andy Warhol, is one of the “Three Sisters” bridges, which are the only trio of self-anchored suspension spans to be built in the United States of America? Neither did I! (And no, I still have no idea what a “self-anchored suspension span” is. I just put that here to sound smart.) Also, my fear of heights is almost gone now! I have my love of photos to thank for that.

— Me in the window seat of a plane, my hair in a messy bun and a pot of orchids in my lap: When you have to fly across the country for a party and fly back the same night, orchids are the only appropriate carry-on to bring.

— A professional photo of Oliver and me dressed in formal wear at a gala, smiling lovingly at one another: Miranda Kerr and Evan Spiegel have nothing on us. 😘

When it rained, it poured. I just tried not to think too hard about the fact that I was missing weeks and weeks of classes to hop on planes and trains and in buses and limos. I wasn’t thinking of consequences, really. I just went. I wanted to have fun, and get more famous, and enjoy my spot in the funnel of winners.

I’m convinced that I would’ve gotten in trouble for my elaborate game of hooky if not for the letter that Oliver had personally written to the Dean of Students, explaining that I was “a founding member of NipNop” whose work was “integral to the growth of the company.” Business, it seemed, was the magic word that got everybody off my back. I returned to San Francisco, went on several road trips with Nevaeh, half-assedly started writing my book proposal, and continued to skip class. By now, I’d stopped really giving a shit about homework, only bothering to turn something in if it affected my grade by more than thirty percent. But aside from a couple of concerned emails from professors, nothing happened.

Somehow, it was okay to spend all of my time taking pictures of myself if it meant that I was helping a company increase their bottom line. Stanford, after all, was known for its famous dropouts — Larry Page, Sergey Brin, Reese Witherspoon, John Steinbeck, Tiger Woods. Perhaps the university thought of itself as an important pit stop in the funnel of winners.

— Me sitting on the edge of my bed with my new Macbook in my lap, smiling at the screen: I’ve been working nonstop on this book proposal! I am writing, writing, writing away, my head the clearest it has been in a long time. Instagram, NipNop, even Stanford have all been means to an end. This end. I’ve spent my entire life working towards this. For the first time in a long time, it feels like sunrise even when it’s sunset.

— Me standing in NipNop’s new office building downtown, arms in the air, an idiotically cheery smile on my face: Home, sweet home! NipNop’s got a new headquarters … and a new logo! The green fairy, designed by yours truly on Photoshop, is meant to be a symbol for ephemerality, and mischief, qualities that NipNop values in equal amounts. If you’re a software engineer with 5+ years of iOS, Android, or backend experience, send me a DM! I know the hiring manager and can put in a good word for you. 🧚‍♂️

Oliver insisted on operating as frugally as possible, choosing for NipNop’s headquarters an old law building at the intersection of 11th and Natoma streets. This was the sketchier part of San Francisco’s SoMa district; it wasn’t uncommon to see rusty shopping carts filled to the brim with grimy bags or uncapped needles abandoned on cracked windowsills. The offices themselves were on the third floor. The lack of an elevator meant that everybody got a free workout whenever they wanted to go in or out. Looking at the IKEA desks and a single fridge stocked with bargain-brand seltzer water, it was hard to believe that NipNop was estimated to be worth between sixty and seventy million dollars. At least the building had a nice view.

— Me standing on a sidewalk holding one of my heels at arm’s length, side-eyeing it all the while: But for real though, always keep at least one eye on the ground when you walk around downtown. Otherwise, you may have a, ahem, shitty time. And I’m not talking about dog shit, either. Apparently, there aren’t enough public bathrooms in San Francisco, so “SoMa Snickers” are an everyday occurrence. I’m looking at you, local government.⁣

“Who cares if the sausage factory sucks, as long as the sausage is premium quality?” Oliver liked to say. “I don’t want to be spending money on stupid shit when I could be spending it on hiring top talent.”

For what it was worth, NipNop did attract great engineers. The company began hiring in mid-January; by the end of February, it released a new disappearing video feature on both iOS and Android, enabling users to get even more personal with one another. The sender could upload videos to the app or record one directly with the camera; the receiver could replay it once before it disappeared forever. NipNop announced the feature by sending the video of me climbing the bridge in Pittsburgh as a Nop to every user on the platform. @helena.holloway getting over her fear of heights, read the overlay.

It was an impressive feature launch, but I still had a hard time seeing why any highly skilled person would want to work at a company with zero cool tech perks and a CEO who used the term “sausage factory” without a hint of irony. That is, until Oliver called me in one day and invited me to officially become part of the executive team.

This is where I must confess that I’ve omitted another key detail: when Oliver and I made our fake-dating agreement, I wasn’t just trading my influencer services for permission to use his name and likeness on my public social media profiles. I knew my worth, knew that I could help Oliver far more than he could help me. So I created a four-slide PowerPoint that illustrated, with as few frills as possible, the fact that I’d brought five thousand people to NipNop the day it had launched on iOS, that having me could double or triple user growth, that this power alone was worth a five percent stake in the company.

Oliver had refused to dignify me with a response when I’d first proposed it, instead giving me a puzzled half-smirk combined with an incredulous laugh that I later found out was normally reserved for his parents. “Five percent? Are you out of your mind? That’s how much Erik owns. He provides us with food, nice beds, office space, and fast Internet. Oh, and he gave us a hundred and fifty thousand dollars in seed money. What do you have to offer? Your Instagram account?”

I decided to forgive the sneery tone — five percent was a lot, and I had more or less ambushed him when he was already three joints in during a smoke session. “NipNop is in a crucial stage right now,” I began. “You’ve already gotten into this series of fortunate events — I call it the funnel of winners — by having Startup House fund you. Now, you need more users so that you can get more money and grow further. That’s where I come in.

“If you have me send NipNops to your users, I guarantee that you’ll reach a million monthly users by this time next year. And when you do, I’ll pull a huge publicity stunt to get NipNop into the newspapers.”

Oliver narrowed his eyes at me. “Like how?”

“I dunno yet.” I flashed him the million-watt influencer smile I’d perfected in front of my bathroom mirror. “I’ll rope feminism into it. People love hot, successful white girls who take some stand about femmes’ rights. I’ll serve your audience — our audience — some piping hot Lean In bullshit.” I leaned closer to him to underscore my point. “They’ll eat it up, and we’ll both walk away one step closer to our goals.”

He laughed. “I do love the way you think.”

“With five percent, you could have me thinking for you all day long.”

“Well …” Oliver pursed his lips. “I’d have to talk to my co-founders about it. But I can promise that we’d all be very interested.”

I shook my head. “Right now, or I walk.”

“Fuck you.” A pause. “Wait here.” He got up and ran out of the room, yelling as he went. “Andre! Elio! Emergency meeting, downstairs pantry, now.”

Thirty minutes later, he was back with his co-founders. They were willing to give me one percent. I was firm about five. We went back and forth until Oliver’s high completely wore off, at which point he looked at me with a mixture of annoyance and respect.

“Three percent,” he said, “or you walk.”

I smiled. He was finally speaking my language.

“So are you in?” Oliver held out his hand.

“Definitely.” I gave it a firm shake. “You have a deal.”

That long-ago exchange was on my mind as I opened the door to Oliver’s room. Everything looked the same, from the rainbow glow of his gaming keyboard to the #STARTUPHAU5 spray-painted on the wall. I wondered if Erik was still letting the NipNop founders stay rent-free. If so, what the fuck was he doing?

Oliver sat on his desk, elbows on his knees, fingertips of both hands touching in that “hand steeple” gesture that public speakers loved to use to show confidence. It wasn’t working. His skin was pale, eyes shifty, left leg erratically bouncing up and down in that universal display of nervous impatience.

“Why do you look like you’re waiting for your girlfriend’s pregnancy test results outside of a sketchy gas station bathroom?” I asked by way of saying hello.

He choked out a strangled giggle. “Just a little stressed, I guess.”

I perched on the edge of his bed, one leg crossed primly over the other. “What’s up?”

“As you know, NipNop recently raised a thirteen-point-five million Series A. We’re expanding the team, and that involves some executive roles —”

“Yeah, and?” I gave him a look. “You act as though I haven’t been literally celebrating with you every step of the way.”

“Right. Exactly. Which is why I think you should join us full-time as NipNop’s Chief Marketing Officer.”

That was not what I was expecting to hear. “You want me to stop working on my brand to do marketing for NipNop?”

Oliver stared at me like I’d grown an extra nipple on my forehead. “What? No. Jesus, no. Of course you’d be able to keep doing your Instagram and writing your book. I’m saying that you should drop out of Stanford and do this instead.”

“Don’t I already do marketing for you guys?”

He nodded. “This would be an expanded role. Instead of just being an influencer and attracting users through your own account, you’d be managing the overall NipNop strategy, working with other influencers, making sure that NipNop dominates the market in all sorts of niches. We want to be more than an app for ugly selfies or ten-second nudes. And Andre, Elio, and I think that you’d be the perfect person to steer this rocket ship through all sorts of deadly, unexpected waters.”

“You’re mixing metaphors.”

“I remember that you wanted five percent last time we talked business.” Oliver reached for the manila folder by his left butt cheek. “If you join us at this stage, you’ll get a $103k base salary, healthcare covered in full, and an additional four percent stake.” He raised an eyebrow, in full founder mode now, all traces of nervousness gone. “Plus, you’ll get to say that you’re the CMO of an exceptional company. Didn’t you talk about that in one of your Instagram captions?”

I felt like I’d been cheerfully skipping over a meadow, only to discover that it ended in a cliff with a thousand-foot drop. “I’ll have to drop out of Stanford?” I asked numbly.

“I’m not gonna make you do it, but let’s be real. Stanford is ridiculously expensive, and it’s not like you go to class anyway. What do you need that degree for — to call yourself an art historian in your Instagram bio? Fuck that. ‘Chief Marketing Officer’ sounds so much better.

“You’ll have your own corner — and maybe eventually your own team — in the office, and you’ll be able to work on your book whenever you’re not busy with NipNop stuff.” Oliver placed the folder in my lap. “Take a look.”

There was a sheaf of papers inside, each with letters tinier than the last. My hand shook as I studied the first page. I could barely make out the words Helena Holloway, NipNop, marketing, total of seven percent share in the company.

“Would I be your … employee?” I asked slowly.

Oliver shrugged. “Technically yes, but your title, position, and share puts you closer to co-founder status. You’d be an executive, Helena. At twenty! How many Stanford people do you know who could say they accomplished that?”

Not very many, it was true. Suddenly, I was back in the hallway outside of Wren Falcon’s office, watching him say I don’t know anybody named Helena. The room froze, and I became hyper-aware of the moment: Oliver on the desk, looking down at me, the smell of stale Monster Energy drinks hanging in the room, the woosh of the N train as it rumbled by the house.

I’d thrown that huge I’m-my-own-person-too fit on Instagram because I knew the publicity it would bring, but those feelings had been rooted in truth. I didn’t want to be in Oliver’s shadow, didn’t want NipNop’s greatness to eclipse my own. If I said yes to this offer, I’d be richer and more well-known than I’d be by myself, but I’d also forever be tied to something my fake boyfriend had created, forever known as a version of ‘Oliver’s girlfriend.’ Wasn’t I supposed to be the captain of my own ship? What did it mean to build something, if the vision wasn’t entirely mine?

“So, what do you say?” Oliver looked at me, beaming. “You and me, best friends, partners in crime, visionaries of the future.”

“I’ll have to think about it,” I said numbly.

Oliver slid off the desk and walked over to where I was sitting. “Bret suggested, like, five people for the job. She knows the best in the biz. Do you know what I told her?”

I looked up at him, taking in the greasy hair pulled back from his face, the new patch of acne that had sprung up on his chin, the slightly frenzied look in his eyes. “What?”

“I said, ‘I want Helena Holloway. She’s the only person I’ve met who is my age and as talented as I am about getting what she wants.’” He crossed his arms proudly. “Bret relented.”

Thoughts zipped through my mind like locusts on cocaine. Funnel of winners. Oliver’s employee. Co-founder. Shadow. Book deal. Extraordinary event. Fake boyfriend. Instagram. Brand strategy. Seven percent.

I could deal with big moments, with life-changing decisions, but I was used to being the one propositioning, the pushing, never the one who was expected to give a yes or no. My — and NipNop’s — future hung in limbo, waiting to be determined by the utterance of a single word.

And my answer was …

“… I’ll have to think about it.” The hyper-aware feeling intensified. I swear I could feel the adrenaline coursing through my veins, the goosebumps rising on my arms and legs as I imagined what life would be like as NipNop’s head marketer.

“Of course. I’m not going to make you give me an answer on the spot. I’m not that vicious.” Oliver smirked at me. “Read it, examine it, hire a lawyer to talk it over. Let me know in a week —” he paused just long enough to wink at me — “or I walk.”

Next chapter

Chapter 13: La La Sand

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