New Rules NYC (#Wattys2015 Winner)

Be a Boss, Date Your Staff

Zack watched as a group laughed at the bar, two guys with three stunning women, SoHo style crowd. We had come to La Esquina on his request and certainly his shout.

“You know, I read this list the other day,” he said, “Tom Ford – things a man should own, or be able to do. One of the points was a well-cut black suit. The list was old school, but still solid. I think I need to go shopping.”

“You definitely need to go shopping. What else was on it?”

“A bunch of different clothes, fresh underwear every six months, sunnies, He said the most important thing was a sense of humor, anyone could buy the rest, but – a sense of humor you had to find yourself.”

“Wise man. Anything about being able to code? A pair of Jordans for every occasion?”

“No. But I was thinking he should add: being able to take a decent photo.”

“Yeah, maybe. Too many people taking photos already.”

He toasted to new year, which already felt inappropriate. I loved the Margaritas here, built with substance, bold flavor.

“How’s that Nike thing?” He said.

The ‘Nike thing’ was a potential video gig, a project with shoots in Africa, Europe and Brazil. A directing project that was going to simultaneously solve my financial issues and catapult my career to the next level. Hindsight – much too good to be true, or at least bank on.

When you want something really bad, when you picture yourself living it, that swelling feeling talking to people about it – it warps your perception. It clouds your sense of probability or reason.

When it was clear that the Nike gig wasn’t happening, I finally pulled the pin on the tiny video jobs the production company was giving me. On principle I guess, they paid peanuts. They quickly moved on to a couple of other young filmmakers. The industry is an empire built on the dreams and sweat of twenty-somethings trying to make a name for themselves. You need to scamper your ass up the ladder as there’s always someone else ready to take your place on the first rung.

Zack wanted to know about the weekend, who was out, the parties, the music – I indulged him but it was the same old stuff. I grilled him about ShowUp, his app that let people pick up cheap last minute tickets to events close to their location. It was growing quickly and was getting coverage on all the tech and mainstream news sites, the Times said it could be the “Biggest disruption to the events industry since electronic ticketing”. Before he built it Zack used to create internet bots for buying early release tickets and sneakers online, then sold them at huge markups on Stubhub and eBay. I scored a couple of pairs at a relatively low price; he still has this epic collection which must be worth a fortune.

“We have this new girl at work – well, she started a couple months ago – Daniela – I’ve tried to get past it, but I think I have to ask her out.”

“What! Wait. How many people you got now?”

“Seven. Plus interns, so ten.” he said.

“Seven. Dude. And you want to date one of your seven employees?”

“You don’t understand man – I’ve been debating this. If it wasn’t…”

“Did you hire her?”

“Yeah, but…”

“And you are her boss?”

“No. Well I guess. She does the communications stuff but it’s not like I work with her day to day.”

“No? You just perve on her? Abusing your power and tech founder status?”

“I knew I shouldn’t have told you. It’s not that simple.”

“Come on man, just get out more. You can’t crap where you eat. Especially when it’s a tiny box where you also sleep most of the time.”

“She has this suction I can’t explain it, it pulls me in, throws me off completely. It’s like I’m stupefied, bumbling about. She is super chill, beautiful cheeks, eyes. She wears these jeans, I’m sitting there almost eating through my lip, gnawing into my jaw. She is a French and Ecuadorian mix, grew up in Miami.”

“Ah, New York dude, the best combos in the world.”

You could smell the frustration on this guy. We flick through a couple of photos on his phone from her Facebook page. I could see the attraction, although she looked a bit too innocent for Zack – the type of girl that might have some very protective brothers, a father that is a little weird after watching all of his friends ogle her from a tender age.

I reckon the types of people we imagine we’ll be a good match with are often way off. People look for someone exactly like themselves. I was sort of disgusted by it, this narcissistic conformity, an absence of any friction to rub against. No surprises, nothing new. They pay these crazy rents to be in a city that brings together the most amazing platter of different cultures, only to hunt out their own stink. I just found it odd.

“I moved her as far away as possible,” he said, “I even changed my screens so I have to turn to see her. But I can’t get anything done, it’s like there is this pulse inside her, every step, even when she is sitting down, her whole body jolts and bounces.”

“Whoa, look out big guy, keep the blood in your head”

“And she actually cares about what we are doing. Not like all the other girls that pretend to talk tech.”

“You’re going to have to fire her.” I said.

“What? No way. Fire her because I like her?”

“Find a way to make it work. Can you swap her with some other company, maybe get her to…”

“Arrrgggghhhh. This is crap.”

“You need to get laid man. Living in that little office and trying to creep on your employees is gonna blow your head off. I’m playing at that new Verboten club this weekend, come by, meet some people. Get your mind off her. Take some tips from Jay, that dude has a different girl every week. I’m having dinner with him Tuesday, come along.”

“Man, we are smashed at the moment, thousands of downloads everyday, constantly fighting to keep things from breaking.”

“Look, unless you get your head outa this girl, you’re gonna end up going loopy, or at least do something stupid that leaves you broke from some lawsuit before you can even cash in.”

I took a solid draw on the drink, watched a table of girls stealing glances at the guy from Entourage sitting in the corner on what looked like a date. We laughed about the ridiculousness and the politics of it all, the layers obstructing urges and attractions.

“Why can’t I just be straight up with her, it’s my business, I don’t even have an HR department.”

“Maybe. Life is short right? You can’t mess around with this stuff, the regrets will eat your insides when you’re old and barren, stalking her online, trying to jerk off while dodging family photos of her sixteen kids.”

“Shut up man.”

“Hey, look at it this way. If you ask her out and she denies you, you’ll probably find your way to stop glorifying her. So you move on. Winters almost over.”

“Whatever. It’s the middle of January. Anyway she won’t be able to say yes because I’m her boss.”

“Let it go dude. You are absolutely killing it, do whatever you want, put dick pics on her desktop, change her job title to CEO fluffer. Who cares? Haven’t you got other things to think about? I thought you hit me up to help sort me out.”