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How to Succeed in Business
John Haberin New York City
A Conversation with Edward Winkleman
The good news is that I bought How to Start and Run a Commercial Art Gallery directly. If the title has you wondering, you should snag a copy, too. And the really good news is that I swore to ignore its advice. I did not start a gallery, but I can introduce you to its ideas and its author.
Work to do
Both make sense. I can hardly imagine myself starting a successful gallery. It takes thinking about money and the long haul, when I would rather be thinking about art. It takes listening to artists and potential clients, when I would probably be lecturing them. It also takes setting rules when it matters—and knowing when to get them on paper. And for all that, it takes letting art finds its way, along with a very personal sensibility about art. 
Edward Winkleman has managed all that since opening a space in Williamsburg. Now in Chelsea, he still makes strangers feel that they have access to actual human beings behind the desk—and to even a healthy gallery as a work in progress. So does his frank and popular blog. More than a few of his artists have appeared in these pages, including Jennifer Dalton, Rory Donaldson, Joy Garnett, Shane Hope, Christopher Lowry Johnson, Gulnara Kasmalieva and Muratbek Djuamliev, Thomas Lendvai, William Powhida, Leslie Thornton, and Eve Sussman. His gallery makes a natural place for a book signing.
The book makes a practical statement just by its organization. After a brief, lively, and personal history of the profession, it gets very much down to business. Chapters give extensive space to the details of capitalization and cash flow, location and logistics. Aspiring dealers may dream most of discovering the next hot artist. And two late chapters do discuss where to find and keep both artists and collectors. First, however, there is work to do.
The work starts with some things that one might overlook entirely. Early chapters insist on defining your program, your markets, and your business plan. The last of those, laid out with especial care, will run longer than my own best business proposals. (Confession: in my other life, I am a publishing professional.) Who knew that one could plan for so much money going down the toilet? With luck, at least some of it will resume a steadier and more hygienic flow.
One may find the book—and the business of a gallery—daunting in another way as well. Chapters run methodically through the options, including the many different art fairs and publicity channels. They even quote hard numbers, although these, too, may date in no time. Edward Winkleman does not, however, even try to make the tough decisions for others. There are too many galleries. There is also, he implies, no secret to success.
Still, one can always dream. I have been going to galleries since one could linger over them all in an hour in Soho, without worrying about Twitter and art-world gossip. One day I rode the elevators in the Fuller Building in midtown to the theme song from The Man from U.N.C.L.E. I stepped around my share of obstacles to East Village galleries in their day and faced my share of open studios in Brooklyn. And it still seems a mystery to me that artists and dealers succeed at all. I interviewed Winkleman to see if I could discover any last secrets.
It took time
As you say at the start, there are many routes to becoming a dealer, including both the arts and business. Neither alone can handle all that is to come. That alone helps motivate a book. What was your route?
EW: I was an amateur painter who dreamed of being a professional artist one day until I met some talented painters and realized how little talent I had. But I realized that I loved talking with them about their work. This led to me working part time for a gallery and organizing guerilla-style group exhibitions (called "hit & run") in warehouses in New York and London. Shortly thereafter I opened Plus Ultra with Joshua Stern in Williamsburg.
Did you start with a big contact list, or maybe back then a Rolodex, of artists and collectors? How crucial is that to a new gallery?
EW: I had a long mailing list, gathered through the hit & run days, but it was mostly curators, artists, and writers. It took quite some time to build up our collectors list. I would say building it is the single most crucial thing a new gallery must focus on. The more you have when you start, the greater the odds are that you'll survive. But I've seen galleries with very few contacts among collectors quickly make them, because word spread about their programs.
For you, is there a breakthrough moment when you know you have made it?
EW: Financially, it's always going to be a roller coaster, so there's not a real "made it" point in that sense. When you feel you've helped your artist gain a foothold in the history books, though, that's a real sense of accomplishment. I have yet to have a big sense that "I've made it" actually. There are milestones, for sure, that tell me we're contributing to the overall dialogue. But to imagine that's important against the backdrop of art history is not something I've done or see happening too soon.
Get with the program
One thing comes up over and over in your book, from the very first chapters through the details of raising money. I mean the importance of a profile, a statement of what makes this gallery unique. Why is it so important?
EW: It's not that important to the casual visitor, I'm sure. It's more important in helping guide a business owner through the tricky decisions that present themselves daily. Should I advertise a photography exhibition in a photography magazine or a more general fine art magazine? It depends on the type of photography I'm talking about.
Indeed, your book is wonderfully specific, about finances and about the options open to new galleries in finding press, artists, and collectors. Take, though, a gallery just starting out. You have a lot of options, from places to advertise to the many art fairs with different profiles. How can you find your niche and find what you can afford?
EW: Again, if it's highly conceptual, then the photography magazine audience might not be a good investment. Even if it brings in a group to see that one show, unless I have other work that interests them, I'll probably have overspent for that ad. Knowing that your program is highly conceptual in nature or highly formal, for example, should guide where you advertise, which fairs you apply to, how you design your Web site, etc., etc., etc.
Sure, there are galleries specializing in certain styles or media, but most of us go through a weekend of gallery-going with only an intuitive sense of what makes a gallery truly yours. What makes the difference?
EW: I guess the main message is to know what your mission is so that you can check your decisions against it as you're presented with the need to make them. If X or Y doesn't directly support your mission, no matter how well they work for another gallery, you probably don't want to do them. You won't necessarily know this, however, unless you've taken the time to think carefully through what your mission is.
Accidents will happen
You wrote this book to make life easier for others, and that has to mean avoiding major mistakes. Is there one surprise that you encountered as a dealer that you should have avoided?
EW: Yes, I used to think that getting lots of press went hand in hand with lots of sales. Both are important and they do relate somewhat, but the truth is some types of art sell more than others. Unless your program includes some of the kind that sells, you're in for a very tough time of it.
As one obvious mistake, a typical gallery needs up to three years to become profitable. Yet so many go under in a year. What are they doing wrong?
EW: They didn't have enough working capital or they didn't control their overhead. Many of them over-advertise in my opinion. Advertising is important, but it doesn't work in the art market like it does for a supermarket. It won't drive in tons of customers wanting to buy the next day. It works much more slowly, possibly taking years to really pay off.
As complete as the book is, it came out just as the Great Recession was changing everything (including the 2010 Whitney Biennial). Is there one thing you wish you could take back? Is there one additional piece of advice you wish you could offer?
EW: I did have the chance to add some recession-time advice (adding a "How to Raise Money Quickly" section), but in general I think most of the advice applies through any economic conditions. I can't think of any specific advice that I didn't put in there already. I've blogged about how, because it can take three to five years for an emerging artist gallery to become truly profitable, beginning during a recession isn't the worst idea. You're getting through the lean years while everyone else is in the same boat. You're also gaining name recognition that you can't buy once the economy picks up again.
Challenges as opportunities
Is there a moment when you would have to say to someone, it is time to quit?
EW: When to quit is a conversation most dealers are having or hearing quite a bit these days. There are obvious business indicators (e.g., you're broke and can't access credit) or personal indicators (e.g., you dread going to the gallery). But for many art dealers, as with any small business owner, you go into it knowing it's going to be a struggle. You try to look at the challenges as opportunities. When you fall down from exhaustion looking for those opportunities might be a good clue that you should quit.
It must be hard on others as well as yourself.
EW: Yes, and when you're making terrible business decisions with regard to your artists or collectors is another indication. You have to be able to look them in the eye and yourself in the mirror.
Will there ever be a point when the self-promotion of the Web makes dealers plain obsolete? Or does it just mean that you demand more of your artists on the marketing side?
EW: That's the central question for the industry as it exists today, isn't it? I've seen folks recommend leaving the exhibition business to nonprofits and having artists manage sales through their studios. Nothing wrong with that if it works for an artist. But I do suspect artists (as much as they'll complain from time to time) enjoy certain aspects of working with a dealer who loves their work. So I'm not convinced we'll see dealers vanish anytime real soon.
How to Start and Run a Successful Gallery, by Edward Winkleman, was published by Allworth Press in 2009. The interview took place in September. A second edition of the book appeared in 2018 with a co-author, Patton Hindle. Portions of the interview first appeared in Artillery magazine. A related review looks at the future of the gallery.