Chapter 1: Never Give Up

SAM

Picture it: December 5th, 2020. I’m cold and cranky. The hand warmers in my pocket are barely room temperature as I’m standing in the middle of the tasting room at Wölffer Estate Vineyard. The wind, as if cued by Elsa herself, howling, like this swirling storm inside. Outside, the rain is coming down in sheets and the terrace is sparse with heat lamps as I navigate through one guest demand and annoying interaction after the next. It’s been a challenging couple of shifts at the vineyard. The days of floating through glorious surroundings beneath the warmth of the sun while pouring magnums of Rosé to wannabe influencers and earning silly amounts of money in the process are a not too distant memory. But the reality of the off-season and another potential shutdown are setting in like frostbite. Yesterday I woke up to a dwindling paycheck and went to sleep having just uploaded a photo of my vehicle registration to the Uber Eats Driver application portal. I’m turning 34 in just a few weeks and this isn’t yet the vision of success I had for myself. I’m having an unexpected moment of self pity after an otherwise exciting and prosperous time working at this place. Truth be told, this experience has unarguably been the silver lining of a year that will be counted as one of the worst for many people. But not quite for me; which has me wrestling with feelings of guilt and gratitude on a daily basis. 

It’s a strange phenomenon, experiencing both a low point and a high point simultaneously. The low point being COVID induced fears and anxiety, potential financial stress and the nonsense that comes along with working in the hospitality business. The high point being an underlying yet overwhelming sense that we’re* on the precipice of something incredible, having formed a new company with limitless potential just a few days earlier. I head upstairs to say goodnight to Miles, who is doing double duty as both my manager at Wölffer and my enthusiastic new *business partner, and I glance at the sign that he has mounted above his desk. It’s simply crafted. Just three words printed in serif font on a piece of white computer paper. I’ve noticed the sign dozens of times, but on this particular evening as I’m feeling frustrated and exhausted, it resonates more profoundly. It reads: Never Give Up. 

Five Months Prior...

By the time July rolled around I was desperate for a change; both of scenery and of life. I’d spent the previous four months disappointed over the cancellation of the Tribeca Film Festival and treading new waters as we shifted to produce an ambitious virtual event. This while surrounded by the horrific effects of the pandemic in New York City, struggling through the uncertainty of quarantine, and having to accept the reality that the rest of the gigs I had lined up for the year would not be happening. It was that reality, the one of having no income and an American Express balance bolstered by months of online shopping that prompted me to cold call Wölffer Estate Vineyard one random afternoon - July 1st. I was no stranger to the establishment. Having patronized it for many years and having celebrated some significant occasions there including my rager of a 30th birthday, I always considered it one of my happy places. That, coupled with a strong desire to learn more about winemaking, encouraged me to think it would be the perfect opportunity to earn some money and buy some time. I spoke to a woman on the phone who told me to send an email to info@wölffer.com, which I promptly did. The subject line: Interested in Seasonal Job. The opening paragraph, in retrospect, obnoxious as fuck: 

“Greetings - I'm currently a video and live event producer looking for a gig in the service/hospitality industry since all of the work I'd traditionally be doing during this time of year has been cancelled due to COVID. I see this as a rare opportunity to get out of my current environment, meet new people, and do something I'm good at and enjoy very much. I spent many years working in restaurants (summarized below) and have also worked with the Hamptons Film Festival for the past few years, so I've spent alot of time in the area and know the community and clientele extremely well.”

Days went by. No response. I applied elsewhere. Gurneys in Montauk. The Bath and Tennis Club in Southampton. Devon Yacht Club in East Hampton. I was desperate to have a summer adventure reminiscent of Flamingo Kid. All of the other establishments politely refused to hire me. Perhaps it was the fact that I had no recent experience. Fuck them, I thought. Then, on July 6th, I sent a follow up email to Wölffer. Later that day, I received a call from an unknown number. The area code: Bridgehampton, NY. This was it. “Hello, this is Sam” I answered, with some nerve. The voice on the other end of the line was friendly but direct - “hey Sam, this is Miles calling from Wolffer Estate Vineyard.” Our conversation was brief but productive. We discussed our common backgrounds working in the entertainment industry and our mutual love for the East End. He offered me the job over the phone, which according to him, was untraditional since we had not met in person. I think he said, and I’m paraphrasing here, he just had a good feeling about me. Of course, accepting the job was contingent upon finding a place to live in the area, which would become my next mission. Find an affordable place to rent. In the Hamptons. In July. For reference, the median value of a home in the town where Wölffer Estate is located is $5,684,057. Find an affordable place to rent. No easy task. But, being a producer, I’m well versed in the art of making shit happen. I’m also not, as you’ll learn in a few sentences, feeling especially modest as I write this. So I called and emailed dozens of people I knew from my years frequenting the area. Within a week, I had secured a charming little guest cottage on a farm in Water Mill, just 4 miles from the vineyard in Sagaponack. My landlords: friends of a friend who I’d met through the Film Festival. Mission accomplished.

My next mission was a bit more difficult to overcome. Not allowing the fear of taking a “step back” professionally dissuade me from taking this opportunity. I worried what the perception would be within my group of friends and my professional network. Until this point, I’d been on a clear and successful path professionally. The next sound you’ll hear is that of me shamelessly tooting my own horn...but it’s important for context. I’d spent the past ten years producing some of the worlds most successful viral videos for major brands and film studios, winning Webby’s and Clio’s, rubbing elbows with A-List celebrities, and walking red carpets at Film Festivals. And here I was, pursuing a job as a server at a winery. Back into the hospitality industry which I hadn’t worked in since college. Regardless of how much I admire and respect everything about the service industry and its workers, this job did not exactly align with the lofty career goals I’d set for myself in the entertainment space. And it felt, if I’m being brutally honest, less prestigious compared to what I’d been doing for the past decade. That’s a superficial notion that I’d realize only after a few months back in the trenches of hospitality. More on that later. In the meantime, I focused on everything else that this job and the pandemic landscape could offer me. A rare opportunity to explore a new interest without being distracted by the agenda of my career. An excuse to get up every day, have a routine, be physical and be outside after several months trapped in quarantine. A chance to witness the process of growing grapes and making wine. A peek behind the curtain of a growing national brand. A very respectable paycheck. I threw my concerns over perception to the wind and packed my bags. After all, kids, don’t forget: there’s nothing humbling about paying your bills on time. On July 19th, less than two weeks after my first conversation with Miles, I hit the road. My first shift at Wolffer would be the following day. As I drove the 2 hours from Westchester to Suffolk County, I thought about what might unfold in the months ahead. I was excited to embrace what I was calling “a temporary professional layover until life went back to normal.” At least, that’s what I told myself it was to justify making the spontaneous move. But deep down, I came looking for something more meaningful. Inspiration and opportunity that only a place as aspirational as The Hamptons can offer. I’d find it.