Manny Singletary pictured at Cao Fei (photo taken at Art Gallery NSW, in Sydney)

By BIANCA BOVA

Bianca Bova: Thanks for participating in the interview, Manny. You mentioned when we first discussed the possibility that you still think of yourself as new to collecting, as well as new to Chicago, correct?

Manny Singletary: Yes, I've been in Chicago just a few years, since 2021. I was born in Ohio, and I lived in a small town north of Columbus called Mount Vernon, and that's where I went to school, both high school and college. Then I got a job as a software engineer. My background is in computer science and software engineering, and now I'm an insurance tech consultant. I’m based in Chicago but my work has me traveling. I've been to Brazil, Poland, Canada a number of times, and Australia a few times, even living there for a short period.

BB: Did your move to Chicago coincide with your interest in art? Or is that a lifelong pursuit that has just found its rhythm here? 

MS: For a long time I was a “normal” consumer of art. I listened to music, went to the odd museum every once in a while, but I didn't like going to art museums. I thought it was too pretentious and stuffy. I didn't understand what I was looking at, and I didn't understand how to interpret art. And so I just felt that it was like I was of that mindset that a lot of people today are, a lot of my friends feel this way, where it's like, “That's a red square on the wall! Why is this in a museum?”

BB: The “My kid could do that” mentality.

MS: Right, and I think that comes from not understanding that things have context. Then I took an art history class in college, and when I got a little bit educated to understand that it’s not that complicated. It's a vocabulary problem. It's an experience problem. I took it upon myself as a challenge, because I am a very realistic person, I think. At the time I thought that art as a general practice, that artists that I had met and known were not very realistic. It didn't seem like a realistic career path. I didn't really understand it. I just thought, “What's this contribution they're making?” So now, as someone who has many friends in art and someone who has an art collection, I feel extremely different about it. I feel almost the opposite now. I have a deep appreciation for my friends that create, and I feel humbled every time I walk into an art space. I think that shift happened when I was able to start interpreting art through the lens of community, not through the lens of consumption. When I was able to actually have conversations with gallerists and artists and curators, then I ended up with a lot more empathy, and I grew to really appreciate and love art and what it does contribute. 

BB: I'm curious how you went from garnering an initial appreciation through an art history class, to this entry point you discuss as community, because there's a gap between sitting in a classroom looking at slides–or whatever, digital reproductions now, I guess–of famous art, and embedding yourself in a community that can be fairly cloistered.

MS: Yeah, there's black swan event that created that switch. And that black swan event was called, I moved to Chicago and wandered into Heaven Gallery. I was just wandering around on Milwaukee Avenue shortly after I arrived in town, and saw a sign that said “art gallery and vintage store upstairs.” I like fashion, I like vintage clothes a lot, and I thought it was kind of cool to see that with art, so I just went upstairs. There was house music booming, and like Afro beats vibes and I was just like, “This is like a fun space!” I had always experienced art up until that point in these spaces that were more: don't speak too loudly, there’s white walls, everybody's dressed up. Art felt like an event, like a venue, and galleries were a place to feel important and feel wealthy and for people to feel like they want to be around finer things. So I found that a way more interesting way to interpret art could be through an indie gallery. Then eventually I learned Heaven's a nonprofit, and got to know Alma Wieser, the owner. The biggest thing for me was I could go up to the pieces of art, and I could ask questions, because I had had that barrier lowered enough that I felt comfortable. And that’s because Heaven is built to be accessible, right? 

Clockwise from top left: Edra Soto, Kat Bawden, Fengzee Yang, Hope Wang, Delia Pelli-Walbert, Jan Brugger, Jaclyn Mednicov, Belinda Fox, Sophia Muys (top right of cluster), Kendal Murray (bottom right of cluster), Yae Jee Min (left of cluster), Andrew Kuo

BB: It’s non-threatening. 

MS: Exactly. It's a space that's built to serve the broader Chicago. I felt like I could go in there confidently. For the first 12 or 18 months I was in Chicago, that's the only gallery I went to. 

BB: Did it not occur to you to go to other spaces, or were you only comfortable at Heaven, and didn't feel like you'd be as welcome in other spaces? 

MS: To be honest, I didn't know about other spaces! Remember, I just wandered into Heaven, so I also just kept coming back. That's something funny about Heaven–and it's not a good or a bad thing–but Heaven's kind of in their own little world. Later on, I’d get involved with Gertie as an EarlyWork member, and that’s a whole other thing, that’s their job, to bring you to this place you've never heard of. They’re a cultural plug, is their whole theory.

But before I knew about any of that, I just never thought to ask Alma, what are other spaces I should check out? I had never been to a gallery opening in my life, until I went to my first one of Heaven, and I didn’t start buying art right away either, it was just a community thing for me. I started to branch out through my friendship with Francine Almeda, because Francine, at the time, was involved with Heaven. She was also running a space called Jude, and I started to check that out. At the time the idea of spending $500 on a piece of art seemed like madness to me. I have a frame TV, on which I can see infinite amounts of art for basically free, and my attitude at the time was that that’s good enough. The idea of owning a piece of art was just another decision of consumption. Francine sold me my first piece of art though, a Hope Wang work, and that changed my thinking. 

BB: Was it just the conversation with Francine, or was there something about that work that broke the threshold for you, and you thought: I need to have this in my house. I need to live with this. 

MS: I think the thing that broke that threshold for me was I felt like I just liked the piece for what it was. I thought it was cool. I didn't know Hope, and didn’t meet Hope until years later. And Francine is not a super pushy salesperson, then, or now. I think she said something like, “This piece reminds me of your aura,” which was a bold thing for her to say, because she didn't know me very well. And so I was just like, “Oh, that's a good line. You got me there.” So I bought it, and I didn’t really even know how to hang it up. But bringing that into my home, my thinking changed. At Heaven, at the time, work was like $1,000 or sometimes less. So I think I bought like, 15 to 20 pieces from Heaven over the next 18 months. 

BB: How did your collection begin to develop beyond those initial acquisitions?

MS: I don't collect from Heaven as much as I used to. There are different things I value about collecting now that I think Heaven doesn't necessarily cater to. They're a big community space, where now, the last piece I bought was from Patron. I really like working with Patron. I’ve met Julia ​​Fischbach and Emmanuel Aguilar, the founders. They're great. I find that they’re more white glove service, and they're more integrated within the art world. 

Painting by Isabella Mellado

BB: A different tier of the market, certainly. 

MS: Yeah, and so I've kind of moved on, I'm getting more into the methodology of collecting, rather than just seeing it as a form of shopping. 

BB: You started going to art fairs just this year as well, I understand? 

MS: Yes, I went to Art Basel Miami in 2024, and I went with the gallerists Fawn Penn and Delia Pelli-Walbert and the artist Micah Sweezie. Obviously, everyone's heard of Art Basel Miami, as a cultural thing. 

BB: Sure, you know about the parties even if you don’t know about the art.

MS: Exactly. So I told myself, I have no expectations, it’s like if I were to be invited to an F1 race. Like, I don't care about F1 at all, but I would go for vibes.

BB: Culture as spectacle. 

Manny Singletary: Totally. It wasn't my idea to go to Basel. But last year I started spending more time in galleries, and getting more involved in the art world, and meeting more people. Francine had started her new space Tala, and I had sponsored one of the Tala shows, and then I sponsored Sam Reynolds’ first benefit for ReMATCH, which I thought was great, but I felt like I was still in the community-driven art world. I still think Tala is a community space more than a commercial gallery, I think Francine fashions it more as a space intertwined in the community.

BB: She's got the reading room and the retail space. Clearly it operates with different priorities than a gallery, strictly speaking.

Manny Singletary: Right. It's easy to tell that Francine cut her teeth working for Alma and Heaven.

BB: Oh, definitely, that’s very legible.

MS: So then during the Exhibition Weekend gallery walk that Gertie put together, I visited Old Friends. 

BB: I remember that, I believe that’s how you and I first were introduced to one another. 

MS: Yeah! You were there too, that show you curated was up. That was my first time going to a traditional commercial gallery. Which is not to say Old Friends is not for the community, but their goal if I had to put it on paper is ultimately to do right by their artists–to sell their work and help them gain prominence. 

BB: I’m obviously biased having some limited involvement in the program over there, but yes, I’d agree, Old Friends is a gallery operating under the traditional definition. 

MS: Talking with Fawn and Delia, that’s when I started asking a lot of questions about the art world, what that really looks like in Chicago. They were the ones that taught me, that filled in a lot of the gaps in my interests. It was around October or November, and one of the things Delia told me was “You need to go to Basel Miami. It's coming up, it’s not that expensive to go. Book a flight, get a hotel, and we’ll take care of getting you into the fairs and the rest.” The idea was: you need to see the top of the mountain, in order to understand what you’re looking at in Chicago. It sounded fun, and I honestly had no idea how privileged I was to go with them. Looking back, they were very generous in doing that for me. They’re professional art dealers, they had their own objectives and their own goals being there. To take along someone who had never even been to a fair before, to guide me through things and introduce me to people was really nice. We went to Art Basel, we went to Design Miami, we went to Scope, we went to NADA, we went to UNTITLED, and then we went to the Perez Museum. 

BB: That’s a lot of ground to cover. 

MS: I was appreciative that they wanted me to see it all, and that definitely helps develop your taste, but by the end, yeah, I was honestly very overwhelmed. But I learned a lot, and it gave me a lot of questions. The first thing I realized was that fairs are not really for artists, they’re for dealers and collectors.

BB: An art fair is no place for an artist, as I always say. 

MS: That’s what I uncovered–and, art as a business and as a market, because I'd only ever seen art as a community, an activity to build community and foster it until then. So that was my first ever exposure to art as a market. I felt like the dealers there were kind of–not playing pretend, but–this idea of “We are entering a business transaction. I'm cutting you a check for $10,000. We're negotiating this. We're doing a deal.” It was not a community building activity at all, but something very capitalistic, very financially-driven. 

BB: To that end, did you acquire anything in Miami, or was it more of an exploratory trip for you?

MS: I did acquire some work in Miami! I acquired two Bill O'Brien works from Ackerman Clark. And I met John Schmidt for the first time! It was funny to me, because the gallery is not far from where I live at all. Sometimes it's easier to build relationships when you're not at home, though. 

BB: Speaking of home, and art fairs, what did you think of EXPO Chicago, then? 

MS: Well, I don’t like that our 'Art Week' is also EXPO Art Week, you know, instead of say, Chicago Art Week. I found that seeing Miami's Art Week, Miami felt like a venue to see art from all over the world. Miami is a great playground of a city. It's got great beaches, there's great food, and I feel like everybody gathers in Miami to see the art and to throw parties and have fun. I was mostly visiting convention centers and venues that had art from galleries from all over the world, not going out into galleries in Miami.

This was my first ever year going to EXPO too, and I went and I did the VIP program, I did private collection visits, and I did the UMMO party and all that type of stuff. Instead of, “we're bringing the whole art world into Miami and Miami's the venue," I felt like EXPO was bringing the art world into Chicago to experience the best of Chicago's art scene. It seemed like it was about getting collectors in, for collectors to have access to Chicago's art scene. Abby [Pucker], of Gertie, also seems to be very focused on a rising tide lifting all boats, so to speak, raising the prominence of the Chicago scene in a global context. Her events felt like they are about getting people to understand that Chicago's got a great art scene, right? I feel like a lot of the events in Miami were not focused on highlighting Miami as a city, even though its a great one. 

BB: Basel Miami is about delivering the art world to you, and EXPO–at least nowadays–is about trying to bring Chicago to the art world’s attention. 

MS: Yes, I would say that's fair. But I still think it’s an important anchor to the Chicago art scene, and I’ll definitely keep going, keep checking everything out. 

BB: Well sure, it’s like the circus–it's in town, so you go.

What type of collection are you trying to build? 

MS: I’ve never been asked that question before. It's a great question. At first I never thought about my art collection that deeply, and I didn't really think of it as “curating,” I was just buying stuff to support my friends and people that I liked. Now the types of things I want to collect changed a little bit, now it has a context to build from. I think I've got like, 30 to 40 pieces in this collection now. I’ve been making more intentional acquisitions now, and I started doing a bit more research on the recent ones.

BB: Do you collect in a vacuum? Do you make singular acquisitions, or when you say intentional, do you mean you now concern yourself with how the works fit into the overall collection? 

MS: Yeah, I find that having a dedicated context helps me, especially to arrange things better, visually in the space. There are pieces in my bedroom that were definitely influenced by work that was already there. Also, at first, it didn't occur to me that artists sell their work and it just disappears, they don’t see it again. It's a weird relationship between artists, dealers, and collectors. In a funny way I feel like I don't truly own the works on my wall.

BB: It’s true of all artwork that no one really owns it. If you’re lucky, you're a steward of it while you're alive, and you try really hard not to fuck it up.  

MS: Yeah. I feel they are being lent to me in a way because they are a part of an artist's practice. This is very dramatic sounding, but I feel like I own a piece of their practice and a piece of their soul in some way. I feel like I've had a lot of artists tell me, “I'm glad this piece is with you,” and that feels like it is an honor. Every piece also has a story for me in my collection as well, it all feels very personal. 

BB: After you began collecting, you also founded a nonprofit, Vibrant Chicago. Can you tell me about what led you to do that? 

MS: Sure. I'm a patron, I'm a collector, so I'm gonna get the best side of a lot of things for that reason in the art world, if I'm being totally honest with myself. But even so, I've had to in a way write my own ticket into art based on the fact that I don't have an inherent right to be in the art community. I don't create art. I don't have a background in art history. I'm someone that lives in a high rise and makes a decent amount of money doing work in tech and that's great but, inherently, no one has to pay attention to me, and nor should anyone for me doing absolutely nothing. It’s a lot of active work on my part to attend events, to show up for the artists and the galleries that I support, and I will put in as much effort as I can.

What I found very endearing was that Chicago's art scene has given that same amount of energy back to me when they didn't need to do that. It's not a requirement at all. And I found that to be very touching, especially because it's a community of sharing, like Document and Volume and Rhona Hoffman and all these guys all in the same building. Everyone sharing space together. Things feel more collaborative than competitive here. We've got a lot of art schools, there's a lot of indie spaces, apartment galleries. It's a lot of bootstrapping, and there's a lot of cheap real estate in the city, and warehouses, and people can kind of start up projects, there's a lot of pop ups. Vibrant Chicago is meant to support all of these cultural spaces. I felt weird not having a cultural space of my own, not having a place to build community instead of just participating in it. Now Vibrant has a space at Mana Contemporary, we have started to do some programming, we had our first panel talk at SoHo House during EXPO Week. We are a non-profit organization, and what makes us different is we have this multi-year partnership approach to philanthropy. By providing recurring, flexible unrestricted funding for Chicago-based spaces, we’re able to support their long-term, independent growth. 

BB: Do you think you’d be doing this no matter where you were? 

MS: I feel very privileged to be in a position in Chicago where people want to have my business and want to help me build this collection, and see my perspective as valid. Would I have this experience in New York? I don't know, maybe. Maybe New York would be totally fine. Maybe, like, if I were to develop my perspective in another part of the world entirely, maybe it'd be fine. I don't know. But I am in Chicago, and I’m glad I’m in Chicago. It’s working out so far. 

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