If every artist’s arc had a single-sentence takeaway, Kai Samuels-Davis’s might well be: Never underestimate the power of figuring out what you don’t want. It’s a theme that’s played out in the Bay Area painter’s experience more than once, often in life-changing ways. The first big boomerang came in art school, when Kai, who had dabbled in everything from printmaking and photography to drawing and sculpture as an undergrad, enrolled in the graduate film program at Art Center College of Design in Pasadena, California. Almost instantly, he realized his mistake. “I didn’t know what the film industry was,” Kai explains. “Going to film school just made me realize I wanted to be a painter.”
That realization wasn’t without its woes. “I had a mini mental breakdown, because I was already way in debt for the program,” Kai says. “But I slowly transitioned to painting, and started taking more and more painting and drawing classes instead of my film ones.” While Kai ultimately completed the film program, he managed to get the thing he needed most from the experience: an artistic focus to build his life around (nevermind that it wasn’t the one he got a degree in).
Today, Kai’s distinctive style of work comes out of competing and conflicting desires: his compulsion to create realistic, beautiful, and traditionally and technically flawless work, and his greater urge to mess up that work before the paint has even dried. Kai’s decision to turn his back on that first impulse is precisely what makes his work so compelling—just ask his 47,000-plus Instagram followers.
We chatted with Kai to learn more about his path to becoming the painter he is today. Read on to discover his story and shop the collection.
How did you get started with painting? Were you always artistic?
I’ve been drawing and painting since I was a kid; in first grade I made a whole series of weird pencil drawings of these toucan-penguin hybrid birds, and I would sell them for a quarter apiece to kids in my class. Then I’d use that money to buy the junk food I wasn’t allowed to have at home. I was like, “This is great!”
I like that you were monetizing early—you weren’t just in it for the love of art.
I was in it for the junk food. But yeah, art was the only thing that ever held my attention, and the only class I ever cared about in school. There was never a question in my mind when people asked me what I was going to do. I’d say, “I’m going to make art.” I grew up in upstate New York in a pretty small and sort of sheltered town, so when I’d say that, people would look at me like I was crazy, like, “Well, okay, you’re going to make art, but what are you going to do to make money?”
What about your parents, what did they think about your chosen path?
They were really supportive. For my 16th birthday, they got me four classes at the Woodstock School of Art; I spent that whole summer going to art school and doing sculpture and painting and drawing. It was the first time I’d ever been really immersed in making art instead of just a class here and there for half an hour. That’s what clinched the deal.
What led you to open an Etsy shop?
When I finished grad school, I met my wife, Clare, who is also a painter, and got a job working for a really successful artist. That was the first time that I’d pursued a job in art. He had, like, a 10,000-square-foot space in Santa Monica and sold paintings for $100,000. To be working in that sort of environment was surreal. I was like, “Making art got you this? Holy crap!” I got to sweep that room, and he got to paint there. That was a good kick in the pants to really get my own stuff going.
When we moved to the Bay Area in 2009, Clare and I each set up Etsy shops while we were looking for work—just any kind of jobs to pay the bills. We got a couple sales on Etsy, then we got a couple more. Clare’s work started to get a lot of attention: She was a Featured Shop on Etsy and she got some mentions on big blogs, and it just took off from there. All of a sudden, we were like, oh, we have jobs now. We don’t have to keep looking for crappy jobs.
Today, most of my income comes from selling paintings, and the prints subsidize things. At the beginning, it was really hard to justify working on a painting for months when I didn’t know if or when it was going to sell. Etsy made it so I could afford to just focus on my painting. Without Etsy, I don’t know what we would have done.
Do you and Clare give each other feedback on your work—or advice on running your Etsy shops?
Yeah, both. I think I gave Clare more advice on Etsy in the beginning and now she gives me more advice. We’ll brainstorm together and give each other advice and feedback; I think we’ve each really helped the other’s work grow a lot. It’s great to have someone right there who can relate, that you can bounce ideas off of. And with Etsy, neither of us had done anything like that before. We’re always talking about pricing structures and the logistics of shipping; we ended up where we are now through a lot of trial and error.
How long have you been working in the style that we see in your shop today, and how did you arrive there? Has your work evolved a great deal over the years?
I always had intentions of my paintings being in between representational and abstract. I wanted them to be expressive, sort of a balance between chaos and order, where you had to figure out what it was. For some reason, a few years back, one side of my brain was winning over, and my paintings started getting more representational and just very literal. I think I kind of lost focus. Around the end of 2012, I got really fed up with myself. I’d look at the paintings and think: These are boring, this is not what I want to be doing.
So I was like, I’m going to paint a blurry, messy face—I’m going to paint it just for fun and to break me out of my funk. That was the painting “The Beginning,” and that pretty much started the style I have been working in since. It was such a eureka moment, to be working on a painting and having so much fun. I got to explore while I was working on the painting, and then that translates to the viewer, where there’s more for them to explore.
As things got more fragmented in my work—the blurs, the places where the background and the subject sort of merge and break apart, things like that—I felt like I was getting my intent across more, translating the emotions better. You’re not looking at it as if it’s a portrait of a specific individual, it goes past that. And everything has evolved from there.
Even now, though, there’s a part of me that says, make that eye look perfect. I have to remind myself that it can be messy and still be good. But I still hear that voice in the back of my head telling me to make it look pretty, and it drives me nuts.
How do you combat that voice?
One big thing I figured out was that I was spending too much time trying to get my paintings perfect before I could start messing them up. I would go crazy for days in the studio trying to get one proportion right, and I didn’t like that struggle. I do like some struggles with painting, but that one didn’t feel worth it.
So I got a projector, which I was always very against—it felt like cheating to me—but when I tried it, it was fantastic. I could project a very simple outline to get the basic proportions, spend a few hours blocking in the whole painting, and have my nice realistic painting done so much faster. And then take a squeegee and destroy it instantly. Instead of spending weeks getting to that point, I could skip the not-fun step and just get it out of my system—like, alright, I painted a realistic face, there it is, and it’s boring, just like I thought. Now I can put it aside and have the starting point for the actual painting.
What’s your workspace like?
I work in a studio that used to be the garage of our house. All the walls are covered with paintings in progress, and the easel where I work is in one corner. In the opposite corner, there’s a sitting area with a couch and coffee table and mini-fridge, where I can sit and see everything at once. It’s great to be able to scan the room and notice what’s working in one piece that I could carry over to another, whether it’s an element or mark or line or color. I also have a small wood table for working on watercolors. I’d like to get back into inks and watercolors more, maybe do some studies for larger paintings and put those on Etsy too.
Is there a particular piece that has seemed to resonate with buyers the most?
My most popular piece used to be “The Disappearing Boy“; for a long time, that was 80% of the prints I would sell. That phased out, and then it became “The Beginning,” and another one called “The Decision,” which is kind of a blurred, shaky face. It’s a little more graphic, just black and white and flesh tone, and fairly neutral so it works in a lot of spaces. Plus, they’re not too specific; a lot of people don’t like having portraiture in their house, because they don’t like looking at a stranger.
Has there ever been a buyer that you connected with in a special way?
I sold a small oil painting to a woman in England years ago, and then she contacted me and asked if I’d be interested in showing paintings in a gallery shop she owned called the Cold Store in Norwich, England. I’ve gotten a lot of those requests before, and it’s usually a cheesy touristy gallery, someplace my work wouldn’t fit at all. But I went to check out her shop online and it looked really nice—very simple and clean and a very small selection of stuff. I liked the other artists and artisans, so I said yes.
That was 2010, and we’re still working together today. We’ve never actually met or talked on the phone—she did an interview with the British Homes & Gardens and described our relationship as being like old-school pen pals. It’s been a great connection to have. I think we’re finally going to meet this summer when she comes to the Bay Area. In the gallery world, it’s hard to find people you really get along with and who are honest, so if a relationship like that develops, you try to hang onto it.
What’s next for your work and your Etsy shop?
I’ve known for a while that I want to have some smaller stuff in my shop, and I’ve done one batch of watercolors already. I think moving forward I want to start doing some studies and sketches and smaller pieces on paper that I think will be nice to have on Etsy. I like having the prints of my larger paintings, because it makes my work accessible to more people, and we got a large format printer so we can have substantial, good-quality prints. But I think my goal for the next year is to have a smaller selection of prints for select paintings, and then a lot of studies and smaller originals.
The whole last year was consumed with crazy house renovations and working on my last show, and my wife and I also just had a baby, so the last six months have been about trying to keep another person alive. It’s been pretty incredible, but neither of us has gotten much done in the meantime. I have a solo show coming up next April though, and I need to have half the work ready by the end of September. I thought it would help to start doing some smaller pieces as warmups, and I’m going to start listing those in my shop soon.
Photographs courtesy of Kai Samuels-Davis