I hoped my column from last year about my lively internship interview would be my last. But here I am during the first week of July, caddying. And the story of how I got here, although not the best for my starving English Major Complex, befits a column of similar scope.
It all started in April, around the same time as my last interview. There must be something about the changing seasons—the first crumbs of pollen begin to fall, Striped Bass begin migrating north from the Chesapeake, and I begin a month-long rush sending resumes to every listing that comes up on Indeed after searching “Paid Editorial Assistant,” for which very few results exist.
I decided to consider some of the jobs that Career Services suggests for English majors as alternatives to their dreams of becoming writers. I’m talking jobs like PR, marketing, and the many shiny synonyms—brand management, product awareness, and the oh so illustrious Social Media Management (all of which, if you happen to be reading this in a year, dearest company who may be considering hiring me, I would be more than glad to do).
I reached out to a person I followed on Instagram whom for the sake of this column I will call Jake.
Jake has over 100k followers, a Porsche, a Camaro, and, it seemed from his posts, many good looking friends to hang out with in Montauk, N.Y. I wasn’t exactly sure what Jake did for a living, and I’m still unsure now as I write this, but he was at the Rolling Stone party last summer, as per his Instagram post, so I didn’t need any more convincing. On LinkedIn, it said he used to work for PricewaterhouseCoopers, but as I came to learn through this journey, LinkedIn is full of shit.
I sent him an email two weeks before Easter Break, pretending to know what he did to make money, pretending to be impressed by it, and genuinely asking if he needed someone to, “… proofread press releases or Instagram captions,” because I guess those are of equal caliber nowadays.
He responded jovially and after a 10-minute phone call, I told him I could drive out to Montauk for a day over Easter Break and meet up with him in person.
We met on a cold, rainy spring day at a bar near the fishing docks in Montauk called Liar’s Saloon, a real-life variation of the Salty Spitoon, and there I was, Spongebob, eager to show how tough I was.
As I explained to Jake how our cute little publication worked, how the business side and editorial side function, how working for a college paper equipped me with the necessary skills to work with his company, a plump, salty fisherman in the corner cut me off.
“Ayyeee kid, enough about business, a’righ’? Talk about that crap when you’re back at school,” he smiled.
His buddy in the corner chimed in.
“Ayy Murph, ya know what I know about the internet? The fish, it goes inter-the-net.”
They all laughed and Jake, in his joggers, and I, in my cap, sat down for an interview over three dollar taps.
We had as professional a conversation one could in such a setting. When I spoke to Jake a week later, he was excited to get to work and wanted me in Montauk as soon as I got home from school. So a week before Memorial Day Weekend, on a Sunday, I drove out East three hours to meet him in Montauk.
I texted him when I was on Old Montauk Highway, 15 minutes out, and he said, “I’m with a girl named [Tess], she’s leaving tonight, just bear with me bro, go to a bar and network with some locals.” I didn’t quite know how, nor did I care to network with locals, so I went fishing at a beach nearby, and by the time I made 10 casts, he called me and told me to go to Montauk Brew Co.
I arrived and he was piss drunk, trying to “network,” which I would learn was a favorite verb of his that really just meant introducing himself to people at bars.
Jake wanted to go to another bar but there was no way I was riding in his car, so I offered to drive. We went to Montauket, a nice place on the water with live music, and he was basking in the vibes, thanks to the crisp refreshing taste of the new Watermelon IPA from Montauk Brew Co.
I met some more of his “friends,” the ones who were featured on his Instagram smiling and looking good, but the disparity between meeting these people in person vs. seeing them on Instagram was profound. He introduced me by saying “Chet, Jenny, Gossling, McKenna, this is my intern Timmy.” What I imagined to be fun, young, creative 20-somethings were actually a bunch of crusty local coke head girls (more like women, 31+) and surfer guys with long hair (and not in a glamorous way). After a few more hours of networking, I told him I had to be back at my friend’s house for dinner and I dropped him off at his Camaro at the last bar and said, “See you tomorrow.”
The next day, Monday morning, I checked Instagram and saw that he was up until 4:30 the night before, so I waited until 11 to text him so he could sleep in. We linked at noon and he said we have a ton of stuff to do. He was sober, I was excited.
He said “let’s go somewhere we can open our laptops.”
We drove to Main Street, I presumed to go to a coffee shop. Instead, we went to a bar, and not just any bar—one of five that were busted in a multi-million dollar drug ring last summer—and ordered Ahi Tuna tartare tacos.
He told me we’d be promoting this new vodka called Titomirov, made with alkaline water which was supposed to prevent hangovers. I got thinking on some slogans and wordplays to use for social media.
Then he realized he left his credit card out last night, so he got up and started walking the bars on Main Street trying to find it. He called girls asking “Hey, where were we last night? I can’t find my card.” I sat there, enjoying my tuna tartare. Finally, he found it and came back and we got back to work.
He then handed me a note card with three usernames and six passwords and asked me to get into the email accounts. But they didn’t belong to him. They belonged to a premier A-list bar out there. He wanted to “acquire” their contact lists for our own business ventures. None of the passwords worked and he must’ve gotten bored so he suggested, “Let’s go hang out with some chicks!”
We drove to these new condos on the north side of Montauk with a beautiful view of the water. They’re pretty nice, but Montauk and Condos are antonyms. We got to one of the condos and sat on the porch overlooking Block Island Sound and one of the women I met the previous night was laid out in the sun, catching some rays.
Her ankles were marked with ink like they had been just run through the copy editors—I think she might have had an Asian character from each language (Korean, Japanese, Mandarin Chinese, a true world traveler). And on the side of her rib cage was a palm-sized tattoo portrait of Jimi Hendrix, afro and all.
We sat down on the whicker chases but shortly after, her Pomeranian named Gatsby began to edge toward the railing and shake. His owner told us the dog was having a “panic attack” from all of the social stimulation and that the best thing to do was leave.
So we decided to go to the Montauk Beach House. When we got there, Jake gave me a LinkedIn account to log into. The account was named Jennifer and had a picture that I assumed was from Getty Images. Jake told me, “people love connecting with Jennifer.”
I read through some of the messages he had sent from the account in the past as “Jennifer”—he would pretend to be his own secretary, telling connects that “Our CEO Jake will be available for a phone call at 2.”
He then shared with me an Excel sheet of over 800 people who work at Vice’s parent company Carrot and told me to add them on the LinkedIn account to “make connections.” I added roughly 100 people before 6 p.m., when he told me he had to go because he “had a hot date.” I told him I would be back out Memorial Day Weekend and we parted ways.
I got in my car, gassed up before getting on the Long Island Expressway, and texted my caddy master that I would be at work next weekend.
I called Jake a couple of days later and said I didn’t think it was the right fit and that we should just go our separate ways. He prodded me, asking, “Why?” and I tried my English major best to euphemize it all but after he said, “Well you’re the one who came to me!” (which is usually how most jobs work), I told him I was more than willing to sell my soul and write Instagram captions for a job, but I drew the line at catfishing media executives.
Thirty minutes later he sent me a text that said he didn’t get to “$1.0M in the bank, 2 cars, 2 appts, more Fundraising deal flow luxury real estate and VC backed companies then (sic) I know what to do with, parking my car in the parking lot of [bar whose email he wanted to read], free bottle service everywhere I go” from just nothing. He got there through hard-work, blood, sweat, and grit. And probably some alkaline water vodka.
I didn’t respond because I felt a little bad for blowing up his ego so quickly and then popping it with a rusty fishing hook. But after he sent me that Freudian monologue of a text, he sent another.
“And all those contacts on that spread sheet, those are all close personal friends.”
He’s continued to post on his Instagram account and I’ve been able to see exactly what I’m missing out on as I lug golf bags beneath the sun. On the 4th, I’m sure he’ll have a beautifully manicured Instagram story, with bottles of rosé beneath a sky of the same sugary pink, along with small plates of Ahi Tuna tartare tacos and then probably champagne on a boat ride beneath bursting fireworks. And I’ll be at home, grilling zucchini and red onion on my Weber, with maybe a White Claw, and a couple of close personal friends.
Image Courtesy of Wikimedia Commons