Thematic Explorations in Hospitality, Culture & Entertainment

New York City

Jack Chester – Free Range Wine & Spirits

Published January 18th, 2021

In another life, I fancied myself something of an impresario and/or gonzo music journalist, always angling for networking opportunities that would land me on the guest list of bands that I liked who were touring Europe. I had modest success in achieving what Willie Nelson referred to as “getting away with it”. That is, I lived my life as if it were all one long vacation.

Going to see live music was perhaps my first love when it came to developing a lifestyle and identity for myself that I wanted to project outwardly. I wanted to be a psychedelic nomad, a road warrior traveling from place to place and show to show, tempting fate and churning up as much adventure and fun as I could possibly manage along the way. All the while, doing my best to stay one step ahead of the law enforcement types who might have something to say about how much fun I was indeed having. As one learns, usually the hard way, in the eyes of the law there is definitely such a thing as too much fun.

In a life that is richly defined by its edge cases, one tends to encounter others of like mind. For me and my journey, one of those people is my old friend Jack Chester. In fact, Jack first connected with me here in Karlsruhe when he made a detour to meet me on the recommendation of a friend we had in common. I’m sure I did my best to show Jack just how cool I thought I was, and to his credit he invested the time necessary to get to the real person behind all that muck.

Jack is a unique person in my life. He is without a doubt one of the most supportive, talented, single-minded in his convictions, cerebral, sophisticated and loyal friends I’ve ever had. He is honest to the point of recklessness, but that is in fact a quality that allows you to learn to trust him to be himself in any and all applications.

I have travelled throughout Europe with Jack. One day he showed up at my apartment and asked if I wanted to go with him to Albert Hoffmann’s 100th birthday symposium. Given I was never one too afraid to call in sick to work if something more interesting popped up, we were off the next morning to Basel.

It’s funny the number of people I know from this former life of rock and roll mayhem that have found their way into work that is closely related to what I do now. Jack is one of those people.

Somewhere along the way, although I don’t quite recall exactly when, he opened a wine and spirits store in downtown Brooklyn, and this was well before I opened the Commodore Room or Electric Eel. I subscribed to his newsletter and each week I would read his transmissions and lust after the fine spirits and wines he described. I forgot to mention that Jack had written for a US music magazine that originally sprouted from the Grateful Dead scene in the 1970s, which is another reason we were drawn to each other, sharing interests vaguely similar in music.

Jack’s newsletters have become infamous, which we will discuss below. I highly suggest becoming a subscriber. Anyway, let’s get into our conversation with Jack and you can get to know him in his own words.

Jack in his natural habitat.

How the hell did you make your way to owning a liquor store in downtown Brooklyn?

Oh, it was quick and easy. I spent 15 years as a writer, photographer, and editor, burned a lot of bridges, got fired a bunch, didn’t make the transition to digital gracefully, and torpedoed that career completely. I found myself virtually unemployable, but with a decent collection of rare wine, and a wealth of knowledge I had acquired simply by tasting as many wines as I could, out of curiosity and joy. I began selling off my collection – for a decent profit – to a few key restaurants, and did some restaurant and bar consulting. The third time I had to correct a sommelier, I figured it was time to go pro. Spent a couple of years looking for a wine shop I could afford to take over and grow, and eventually found a tiny shop in a great (at the time burgeoning) neighborhood that was about to go under. I took over the liquor license and the lease for much less than it would have cost to start a new shop, moved to a larger space down the block about 8 months later, and Free Range Wine & Spirits was born. Coming up on our 8th anniversary in April.

Free Range Wine & Spirits is the perfect name for your shop. I’m sure people have complimented you on that before. Do you deal much in natural wines? In either case, can you expand on why or why not?

Wow, this is a loaded question, and one of the biggest frustrations of running a retail wine shop. People have been lied to so many times over by marketers that most of them asking for things in this direction have no idea what they’re asking about. Example: “Do you have any organic, or natural, or unfiltered wines, or whatever?” Those are the major buzzwords that people use interchangeably (though the definitions are quite different), along with biodynamic, and the worst one: ‘no sulfites’ (which is physically impossible as the process by which yeast turns sugar into alcohol also creates natural sulfites- and you do not have a sulfite allergy any more than you have an MSG allergy). We carry wines that are delicious and well made, the vast majority are at least sustainable and are made fairly cleanly, some are totally natural, which means no outside additives, but even certified natural wines can have small amounts of sulfites added at bottling. The term ’natural’ is a mine field, and is used so widely, that it means almost nothing. There’s also a subculture of wine drinkers (mostly on the younger side) who seem to seek out natural wines that are – for lack of a more accurate word – flawed. We have some funkier wines, but try and stay away from the geeks only bottles, or brown dishwater with dead yeast floating in them. There is some really unstable wine out there passed off as ’natural’. Neglect is not an effective winemaking technique.

Wait, what?

You concentrate as much as you can on products that come from your region. Can you turn us on to anything that’s really interesting to you at the moment?

Yes! NY is making some of the best wine and spirits in the world currently, but much of it doesn’t leave the state and very little of it leaves the country. We’re enormous fans of Riesling from the Finger lakes, particularly by Forge and Red Tail Ridge. Bellwether has produced the most impressive Pinot Noir I have yet tasted. Forthave is making some of the most intriguing (and beautifully branded) spirits in Brooklyn (Amaro, Aperitivo, Gin, liqueurs….). There are excellent whiskey producers here, especially Kings County and Breuckelen, and Taconic from upstate. The partnership between Greenhook Ginsmiths and St. Agrestis has produced a bunch of cool new products, including single serving Negroni and canned Spritz. Brooklyn Kura Sake has also impressed us. There are so many cool producers here that I could write a book just on what’s being made in Brooklyn.

P.S. The brand “Brooklyn Gin” is not made in Brooklyn. While they claim that they’re greatest dream is to build their own distillery in Brooklyn, to date they remain unrepentant posers, producing an upstate NY gin with Brooklyn Branding. We refuse to carry it.

The bounty awaits.

Do you have any favorites from our area? Using “area” quite liberally here. Meaning the Rhein valley and its border regions like Alsace.

Yes, of course! A lot of the best white wine in the world comes from Germany, as the world well knows, and all sorts of wonderful grapes grow well in Alsace. My very favorite producer of dry Rielsing and Pinot Blanc on Earth is Rebholz (Pfalz), his wines are natural, but profoundly clean and precise, which is hard to accomplish.

I subscribe to your newsletter. I fell out of habit of reading it until recently when I’ve noticed a trend of you sharing stories about the behavior of your worst customers. What’s up with that?

Thanks for reading!

When the pandemic hit, and we were forced to change a lot of our practices and policies, our newsletter went from just being the place where we advertised our weekly in-store tastings, to a weekly online sale, as well as evolving policies and open hours. This led to discussions of what was causing these changes, and things got heavy and political. I’ve always been politically active, and a hardcore lefty, but that began showing itself more and more in our newsletters. We found that people were reacting to – and thanking us – more for the non-wine content, which included politics, neighborhood, and pandemic news. I vented a few times about some of the most ridiculous things that were happening in the store, and this seemed to engage our people the most, and was fairly cathartic for me, once I got over how many people were telling me that the details of my latest in-store trauma “made them laugh”. Anybody who has ever worked in retail and/or service industry has piles of customer horror stories, and since I own the place, I get to tell the really awful ones exactly what I think of them. And these stories seem to really entertain people. I also train all of our people to be courteous and informative, but nobody is here to be abused, and I encourage them to stand up for themselves. The customers who say things like “the customer is always right” tend to be terrible people, justifying their own awful behavior. It’s really just shorthand for “I own you”. We work too hard for that. When we first starting doing that regularly, customers would mention not wanting to “end up in the newsletter”. There’s no question that I’ve alienated some people, but the vast majority are those who would regularly ruin our day(s). I consider it a net positive.

Fred the dog.

You once told me NYC is a unique marketplace. If you are at least semi-competent and offer and offer a good product, you will succeed. What is it about NYC culture that proves that as a rule?

It’s mostly the size and density of the place that makes that true. If you’re doing something worthwhile, the right people will find you, and with so many people here per space, it should be enough. We opened 3 blocks away from a successful, established shop that’s right next door to a major supermarket, and we’re doing great! And I can’t imagine they are doing any less business than they did before we arrived – though they have tried to steal our selections – so maybe we are ruffling a few feathers. The distributor from whom we buy our Croatian wine got a phone call from them, not wanting to taste anything, but seeking to purchase the exact same wines that we carry. Because we also try and work with people of high integrity, so he refused the sale to them. Looking at you, Brooklyn Wine Exchange. But yes, I genuinely believe that this city is big enough that if you’re doing something worthwhile, and have even a remote concept of basic economics, you’ve got a decent shot of making it work. The key is finding a space you can afford in a neighborhood that’s likely to be interested in what you’re doing.

Here it’s very simple, we have elbow room, apartments are large and much cheaper than where you are. We can easily drive away to the country, or even quickly over the border into different countries. We have it really good here, for many reasons. What keeps you in the City rather than escaping somewhere you can stretch out after so many years in New York?

I continue to live in Brooklyn for the live music, art, and restaurants, but those things have been non-existent for almost a year, and I am looking around for my potential next move. But the short answer is that a significant percentage of my net worth is tied up in my shop, at which I still work 6+ days/week. It may very well be time to do something else, somewhere else, and I am currently being pursued by multiple parties seeking to partner and/or purchase Free Range outright. We shall see. Also, I know that NYC is the concrete jungle, but if you know the region, there are some pretty nice escapes within an hour or two of town. One can hop a commuter train and be within walking distance of fairly serene hiking or fishing in less time and effort than most would imagine. I genuinely don’t remember the last time I left Brooklyn, but you know… plague year.

You don’t seem too afraid to express your political views simultaneously while marketing your business. How much of that is due to where you do business?

I’ve spent most of my life making less money in lieu of my own integrity and ideals. It would be a silly thing to change now. I used to get fired a lot. But yes, unquestionably being located in an amazingly cool part of Brooklyn allows me to be who I am and still make a decent living. Free Range Wine & Spirits, in say Alabama, would not likely be profitable while promoting social justice, and railing against the most glaring hypocrisies of our time. There’s a better chance they’d just paint a big yellow star on us, and call it a day. Sorry to my German friends, we do still have the yellow star they put on my grandfather’s coat.

When people close their eyes and think of “New York City”, it’s often Manhattan they dream about. When I talk to you, you seem to make it a point that you don’t get over there very often. Is it just a pain in the ass or what? As I remember, there’s a train not far from your shop that drops you off in lower Manhattan pretty tidily.

Brooklyn is The City. Manhattan is just the overrated landfill island that separates us from New Jersey. The best parts of Manhattan have long been turned into sanitized theme park caricatures of their former glory. It might as well be Orlando, at this point. Lots of money, zero character. Manhattan can keep its bright lights. All of the best stuff is in Brooklyn and Queens, has been for years.

Can you tell us a bit about your neighborhood where the shop is and what places are around that you like/love? Maybe not even places you make it to as often as you would like, but places you like and agree with?

Boerum Hill, Brooklyn is freakin’ fantastic. Even as more and more high-rises (full of Manhattan people) continue to scar the skyline, it’s still very neighborhood-y. Brooklyn as a whole is profoundly diverse and we hear at least a half dozen languages in an average day. Our customers range from service industry folks like ourselves, to Pulitzer Prize, National Book Award, and Emmy winners; lots of writers, editors, artists, journalists. One of my fondest days in retail was when a sweet Kentucky woman came in and requested a crash course in Bourbon. It was Joan Osborne. I resisted telling her that an article about her playing with the Dead bumped my bluegrass story off the cover of a small magazine a couple of decades back.

The landscape of our neighborhood has changed so drastically in this year of the pandemic that it’s hard to answer the second part of that. Sahadi’s is still the best middle eastern market in town. I love the restaurants French Louie, Boutros, Soul Spot, and Sottocasa. While it’s only partially open these days, Travel Bar remains one of the few places I drink whiskey besides my shop and my home. Our next door neighbor is Absolute Coffee, another great business that survives in a neighborhood with 2 coffee shops per block, run by a hard working, multi-lingual immigrant friend of ours.

Neighbors: Absolute Coffee.

Your business is considered essential, which makes sense. Have you seen any changes in your revenue? Positive or negative?

Yes. Both. What a ridiculous rollercoaster of a year. When the NY lockdown was officially announced, but nobody knew who would be deemed essential, we did a month worth of business in 8 days. We did roughly normal numbers for most of the rest of the year, but Nov and Dec were strange. On the really big predictable days, we did very well, actually beat our revenue from the previous year on the day before Thanksgiving, but the Monday and Tuesday before – which are normally very busy – were much slower than the previous year. Overall we’ve done fairly well this year (hence people wanting to buy the business), but it was much harder earned, and what we consider usual bigger orders just didn’t exist. No holiday parties, no office parties, and we didn’t furnish a single wedding all year (which are generally 4-10 case affairs). Considering what has happened to most of retail this year, we’re quite lucky, but there’s no question that the work per dollar was off the charts. Independent businesses that made it through 2020 earned it, for the most part.

Fun: Flip the other side of certain price tags and find “speakeasy pricing”.

You see bars and restaurants suffering – there is simply not the aid available that we get here in Germany. Do you think the future will be different in terms of what types of businesses people would be willing to invest their money in? Bars with no outside seating seem much riskier than those without, even here. I don’t know what I’m really asking, actually. What are your thoughts on a post-COVID world in NYC as it has to do with hospitality?

Wow, there’s a lot to unpack here. First, it’s embarrassing, frankly, that the US is one of the few first world countries to not guarantee any percentage of all citizen’s pre-pandemic wages. Beyond that, restaurants have always been a tough business, and I have a ton of respect for those who can make it work. There’s no question that any space with outdoor possibilities have become even more important. And retail has been going through it’s own slow demise for a decade. The American government’s deliberate failure to help individuals has been shocking, especially on the heels of their multi-trillion dollar giveaway to major corporations and wealthy individuals in the form of tax breaks. Even most of the money earmarked for small businesses went to the wealthy, as a “small business” in this country is measured buy the number of owners. So a billion dollar corporation with 5 owners would get a bunch of free money while many of the restaurants and retailers I know got nothing. It’s not a great time for independent restaurants, bars, and retailers, and it’s hard to say if it ever will be.


  1. Go inside Free Range Wine & Spirits here:
  2. Jack’s Free Range Newsletter Archive.

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