Conversations with NYC dealer and collector Dakota Sika: Creating Collections

Dakota Sika is a long-time art dealer, advisor and gallerist from New York, with experience as artist and as a collector recognised for his expertise with abstract art.

Why do people collect what they collect?

I think, if we want to go back 100 years ago, people bought art and patron artists to have paintings to add cultural value to whatever they were doing besides their way of making money. But they also enjoyed the art, right? So they wanted beautiful things, show them to their friends, and there was no real market. There was no art market.

Then people started saying, “okay, well, these things are rare” and they can resell them. So then in the 50s, 60s, there was this idea of the art market taking form.

But now we’re in a hyper art market. There is people who are coming into buying paintings for the first time, and an entry level painting could be 20,000$, 30,000$, 40,000$. So the bar is so much higher comparatively, it’s not like you’re going to an artist and you’re buying a painting for $500.

I know some artists who are still doing their MFA or undergrad and their paintings are 20, 30 thousand dollars. So it’s a much different game, the barrier is higher.

So what happens to is people see, “okay, I can buy a painting for 20,000. And if the artist explodes that painting could be worth a million dollars, or $500,000”. So, nowhere else can you really make those kinds of returns unless you were buying like Apple stock before Apple was Apple, which is a very hard thing to do.

So I think two things happened. One, since the entry is so high, you needed people who already had money. And two, since the speculative possibilities were also so high, it attracted a lot of people from the financial world. So people who were already investing looked at art as another vehicle.

How do you navigate the challenge of building collections with clients that perhaps haven’t yet developped an eye or have no background in art?

It is like the metaphor of a car on a highway, right? So, they’re in the driver’s seat, they’re driving the car, they’re putting the gas in the car, which is the money, and I am the markers on the road, right? I’m the street signs and I’m the lanes and sometimes, the other cars. So basically I’m guiding them on the options, but at the same time, they’re the one that I think needs to have the motivation, the desire and the needs. So if they show me an artist that I don’t think is that good, I might suggest them another artist which paints in a similar way that is better. Or if they show me an artist I like, I might send them a little bit of a historical context that relates to what that artist is looking at.

Because at the end of the day, a collector only becomes a collector if they fall in love with the things they’re collecting. So if it’s not the person really making the decisions, you know, based off of their own personal interests, then I don’t think they can ever really grow. So generally what happens is someone will connect with me, we’ll start on this journey of buying and then they’ll get into about 10, 15 pieces, they’ll live with those, and then they usually start selling like a third of it. And that’s either because their eye has grown and they realize that one, “I could get a better example”, two, “this actually doesn’t fit the direction I need to go in”, or three, they do some sort of consolidation.

I think that’s like a very natural progression of collecting some people kind of say that as a collector you’re never supposed to sell anything. But personally I had other collections that existed before the one I have now because I’ve been constantly distilling it down to the best possible version that it can be.

But yeah, it has to be driven by their own desire.

Is there a difference between art advisory and collection design?

Yeah. I think it’s very different because what we mentioned before was that there are plenty of advisors who want to push what they have access to, what’s most expensive and what they can make the most money on.

Sometimes my clients get frustrated with me because they’ll send me 10 things and I’ll say: no, no, no, definitely not, not today, no, etc.

And they get like, why can’t I buy something? Because that also goes to the fact of, sometimes too, people just wanna buy. Some people really just enjoy, it’s like how people enjoy shopping for clothes and then they end up with closets filled with clothes that they never wear. The same thing happens with collectors when they get the collecting bug. They want to be acquiring paintings, which is an interesting kind of thing that happens because obviously paintings don’t have any utilitarian value. They can’t live in a painting, can’t sleep in a painting, but there is this urge that you wanna own these things. You wanna collect these cultural objects. It’s the collecting fever.

You said that you can start collecting with 10–15 pieces. How much time it can take for them to get that amount of pieces?

It’s kind of like dating. You know, some people meet and it’s like hot and heavy and like, you’re on a plane three days after you met, going to some vacation town. And some people it’s like you were friends first and you’ve taken a while to get to know each other. And then, a couple months in maybe you go on your first date and it grows like that. So I think it is specific to each person.

Some collectors will want to hit the ground running and in a year they’re done, they bought a hundred paintings and they run out of money. Some collectors are very diligent and they research an artist they want to know and see their practice before committing to a piece.

I personally work a lot on my own gut. If I see something and I respond to it and I can afford it, then I’ll just buy it and then I’ll continue watching the artist and I’ll probably buy one a year later or two years later and then usually buy until I have three or four examples by each artist. So that way I’m collecting the whole arc of their career or a portion of their career.

I saw that you were sometimes revisiting old narratives because some of the artists were overlooked in time and there’s still now the possibility to get very interesting pieces at affordable prices. Why is that? What do you think of narratives that artists are creating today?

Yeah, so this goes back to the fact that historically too the art world used to be very small, you know. So, if you even think about the great artists of the post-war period, definitely less than 100 probably, less than 50 that people really know. And if you think about walking to one art fair in Miami, there’s hundreds of artists that are on view. So the game is so much larger now. So I think that, historically it’s interesting to look back and find the names of the people that were marginalized for whatever reason and bring those careers back into focus.

However, now we have the flip side problem as well. Everybody is in full visibility. I’m sure there’s some artist that’s working in the middle of the woods that nobody knows about that doesn’t have Instagram making great paintings and maybe 50 years from now we’ll figure out who they are. But as far as artist visibility, it’s like…it’s insane.

Historically, there were artists who were like huge deals at their time, selling for a ton of money, that have just disappeared. Their markets went away. So I think a lot of these artists that people are collecting now will totally, no longer be a rap. Which is kind of insane to think.

History can be cool that way too. There’s a lot of artists that we’re seeing at auction now making great prices that people are talking a lot about who literally will not make it to the history books.

What are the tools to use to determine or have an approximation to knowing which are the artists, artworks or conversations that are relevant for history versus those that are more of a trend?

This is the multi-million dollar question. And so this is where all these other factors come in. Like this is where an advisor could really make a pivotal difference in someone’s collecting if they know what they’re doing. Because, you know, what is significant? What is urgent? What is relevant right now? And not just in terms of like social political things, but in terms of art, like what hasn’t been done before, which is just so groundbreaking that we can look back 50 years from now and say this is an incredible painting.

That’s a tough question to answer because there’s also other factors of like, you know, somebody could be making great paintings but maybe not see their due because of luck, financial, personal relationships, their own personalities. I mean, there’s plenty of artists who are just so difficult to work with that they didn’t have success during their lives but later on had success because people then could divorce their personality from their paintings and just say, the work is amazing. But as an individual, they were just intolerable.

But again, to circle back to collecting, if you are buying what you love, that stuff doesn’t matter because the paintings are also going to outlive your own life. So if you’re buying paintings that you can afford, that enrich your life, that bring beauty and joy to you, then it really doesn’t matter if they go up in value.

It’s like, if you buy a sofa for $5,000 (you can buy a painting for $5,000), you’re not looking at your sofa five years later and being like, “why aren’t you worth $20,000?”. You know, you enjoy your couch. And I think a painting will bring you much more enjoyment than a couch, but you know, that depends on the person.

Living with art will change your life and living with great art, you can really feel that. I know it kind of sounds like a cliche but I say this too to these finance guys who come to me like: I have a million dollars I wanna spend and I want to build a collection and whatever, make it look good.

But they actually do begin understanding it when they wake up every day and look at their paintings and like have that, you know, conversation. Then something weird happens, maybe they buy a painting for a hundred thousand. I’ll call them up a few years later and say, hey, I can sell that painting for you for 200,000. And they say: oh, I can never sell it. I love it too much and like it’s not enough money. Where in any of their other deals if they bought a stock and it doubled and they can make a hundred thousand dollars They would sell it in a second. An uncommon unusual thing happens when you live with art and that all rationality kind of goes out the window. It’s like being in love. You’re doing this crazy thing. Like you’re you’re spending hundreds of thousands, millions of dollars on these things that you put on your wall and then you just can’t part with them. You literally fall in love.

Why do you think that love story happens?

I think that’s like an ancient thing. I think that as long as humans have been around, they’ve been looking to express themselves. And if you go back, many generations of artists have been inspired by the cave paintings. And I think that’s the root of it. It’s like a primal thing that people want to have a connection with other people through time. And it’s an intimate kind of instant. A way of feeling like you’re transported through history, you’re there, you’re feeling the touch of someone else. I mean, it’s otherworldly, you know? It’s beautiful.

What do you think about ‘connection’ of the times we live in?

I believe that the world we live in is more and more connected, but also disconnected, on a level of emotions.

Connected more in this sense of access, but disconnected in more authentic or meaningful feelings.

Do you think art is a way to preserve those human connections?

Yeah, I think that especially now as we’re coming into this whole AI artificial era. And it’s funny too, even on Instagram now I started getting, I don’t know why, but these ads for like an AI girlfriend or whatever, like forget your girlfriend and just talk to an AI girl or something like this. I thought it was really hilarious, but I think that for some people, that’s closer to the truth than not. And I think that as the technology and this kind of distance between human connection builds, it’s gonna only intensify people’s desires to have real handmade things.

Yeah. Because there’s so many, you know, I even, to go back to Instagram, if you think about it with like filters, you know, it’s like people use to post photos of themselves. Then there was filters. Then there was all these editing apps. And we’re getting further and further and further away. And now they’re putting filters in the lips and all of that. So it’s like you’re further away from even what a real human is, you know? Even on Instagram, there’s plenty of like influencer accounts that are just totally artificial people. Like they don’t exist. They’re made by a computer program, you know? And so I think people are gonna wanna get closer to arts and crafts. I mean, like pottery is a big deal now. People wanna feel things, they wanna touch things. They wanna feel pain, you know? They wanna get connected back to that ancient cave wall, where people were grinding pigments and rubbing onto the stone.

Title: Conversations with NYC dealer and collector Dakota Sika: Creating Collections 

Type: Interview / Market Psychology & Collection Strategy

Description:

A wide-ranging conversation with New York-based art dealer and advisor Dakota Sika on the emotional logic of collecting, the difference between art advisory and collection design, speculation in the ultra-contemporary market, and why living with great art transforms both buyer and meaning. This interview explores the tension between financial strategy and personal love in the art world today.