Artsy engineer Roop joins Artsy Engineering Radio host Anna Carey to discuss how he got into designing art books and then programming after getting kicked out of college. Roop also shares his dual background as a cartographer for art world institutions and how that experience informs his work at Artsy.
Artsy engineer Roop joins Artsy Engineering Radio host Anna Carey to discuss how he got into designing art books and then programming after getting kicked out of college. Roop also shares his dual background as a cartographer for art world institutions and how that experience informs his work at Artsy.
Welcome back to the Artsy Engineering Radio. This week we're talking to Roop and engineer at Artsy about his path to Artsy, his background in the art world, his career as a cryptographer, and much more. This is part of our series. Who are you? And how did you get here? Hope you enjoy. Hi, everyone. This is Anna here, your host today for the Artsy Engineering Radio. And I'm so excited today to be talking to my fellow engineer Roop. Roop, I'll have you introduce yourself?
Roop:Hi, I'm Roop. I am a full stack engineer here at Artsy. I've been with the company a little over five years. I currently work on the Find and E xplore team whose job is to connect our collectors with the artwork, they'll love whether through browsing search recommendations. Previously, I've been on teams that built out our City Guide. I've been on the partner experience team that you're on now. And and prior to that I was on the Genome team back when that was a standalone thing was actually the part of the company I was hired into all those years ago.
Anna Carey:Yeah, that's right. I mean, Roop, I was excited to talk to you because, I talked a little bit about this on previous episodes, bu t when I was in my former role on communications, I had an opportunity to collaborate with different members of the product team. But it was sort of random, who I actually got to work with. And I feel like you and I actually did get to work together a little bit on different stories and topics related to the genome project. So it was definitely cool to come back and get to work with you this new capacity. So yeah, I'm excited to talk to you. I mean, we had this really amazing conversation at one of our first company get togethers, post pandemic, in person. And we were on a rooftop in Brooklyn as a team. And we were talking a little bit about your background and how you got to programming and how you got to Artsy and I was like, Oh, we have to put this on the podcast. It's so fascinating and really special story is given especially that we're in the art world, and I feel like it's often that engineers at Artsy have these kind of hidden sort of secret backgrounds that are just really fascinating. So yeah, let's kick us off by sort of getting a little sense of, I guess how you got to programming? What's your background? Kind of how you got your start?
Roop:Yeah, sure. So I guess I kind of got like an early start with programming. I learned how to program on the family home computer, which was an Apple 2E, I taught myself Basic and tinkered with like graphics and sound programming of various kinds. And then that led to me even learning some assembly language for that chipset for the old Apple TVs. And that's where, you know, lit the fuse. So much so that by the time I was in high school, I was jumping on streetcar riding around the riverbend and taking classes at the local university. So you know, if you rewind back far enough, I actually have some formal exposure to computer science, in the form of algorithms and data structures and all that stuff way back when. Very dusty memories. And this is like, long before Java actually learned all this stuff in a language called Pascal, which I've never used since. So yeah, so can I got off to like a rip roaring start, but then, you know, by the time I got to college for a number of reasons, I kind of like, did a 180 turned my back on all of that. Even though I had like, picked out a school that I could sell as a good school for computer science, I didn't take a single course, I was busy, like cultivating a whole bunch of other interests, some of them academics, I'm gonna not so much the main thing, I think, for this conversation is that like, I was a work study student the whole time I was in college, and my job was working in the campus Graphic Design Studio. So we had a performing art center with a roster of local and national acts coming through. And we created promotional materials, whether they were like screen posters, or newspaper ads, or calendars, or brochures or whatever. So I that was my work study job. And this was happening at a time when the design field was sort of being turned upside down by computers, you know, the so-called desktop publishing revolution, where all these old physical processes were being replaced by working with software like Photoshop and Illustrator, that's when a lot of these programs which kind of just getting going. I kind of consider that my real education since I, at some point kind of stopped going to class and, you know, actually managed to get myself kicked out of college. I think I think the truth can now be told, I'm a mere high school graduate, Artsy, please don't fire me.
Anna Carey:Wow, I love that. I love that. The truth is out on the podcast. Yeah. What made you originally get connected with that with that first job, like what drew you to that? And also what did you study again, in college?
Roop:I studied math, but that's really stretching the meaning of the word study. I was doing a lot of other things. I was like, you know, as I said, pursuing this interest in design. I was getting into letterpress printing. I was protesting the war. I was working on my billiards game, like all kinds of things that didn't involve going to class which is why I got kicked out. And then when I did get kicked out, you know, I had allies in this design studio and they kind of helped me stick around, I kind of had to adopt an alter ego, because I was supposed to not be on campus anymore. And so under an assumed identity, I kept working in the studio, and kind of got further enmeshed in this design and printing arts and book arts community that was attached to my college. And so that kind of led to me getting connected to a book designer. And this was sort of the beginning of my career proper, I guess this is, you know, it's like career number one. Depending on how you count, I've had four careers or stages of my career. And so that first career was working with a book designer named Bruce Campbell. So he is a designer of art books, who, at that time, was designing about half of the books every year for the Metropolitan Museum here in New York, and as well as a number of other museums and trade art publishers. And so my first job was being his apprentice. And it was a really interesting time, because, as I was alluding to with the other campus job, this is when the design field is undergoing this huge transformation. And I came into it at a time when there was this really wonderful physicality to the work. So you would take these sheets of photo typeset typography, you would slice them up with Exacto knives, you would slide those slices through a hot wax machine, you would press the wax type down on to layout board, you would cover that with a sheet of vellum, and then burnish it down with a piece of whalebone. It was just marvelous. And so my job was to murder all of that and replace it with stupid computer stuff. And so that's what I did. So I helped Bruce kind of transition into the world of modern desktop based art book design. And, and that was essentially my first exposure to... I didn't think of it in those in these terms back then... but this was my exposure to the world of artwork and metadata. That's when I started learning words like Tombstone, which is an abbreviation for artwork, title, date, year, artists, medium, that kind of stuff. So I've kind of been working with artwork metadata since that very first job back at the beginning of my career. And then I started hearing from friends of mine who had like, moved to New York to work in like the first kind of explosion of Dot Com work in the city. And so that was kind of like career number two, for me. I had actually even, while I was doing the art book design, started tinkering with web stuff in the evenings and weekends. And, and so, you know, getting towards like the late 90s, I ended up moving to the city working for a couple of different agencies. And that sort of was career number two, early web stuff. That's when I got some of my early experiences, like destroying production systems, and you know, learning through hard knocks, and you know, all the things that made me a much more careful, apparently, paranoid programmer later on in my career. But I also had some interesting experiences. During that phase of my career, one of the things that I did was to work for some of Sotheby's early forays into online auctions. A weird, fun fact is that, as far as I know, I created Sotheby's first ever online auction. It was extremely low tech, it was a sale of antiquarian books in the year 1908. And it was the back end, such as it was, was a Microsoft Access database that was being served from a Windows NT workstation that was next to my main workstation at the agency I was working at. So it was extremely low tech, low stakes, it was kind of like Sotheby's testing the waters to see if this internet thing has legs. I guess they were pleased with the response. Because after that, they kind of spun up a full scale effort to like build out auction stuff, they went through many iterations of that. And then, you know, Artsy has its own history with Sotheby's, but I worked on some of that early stuff and a couple of different capacities first, as the generalist programmer who put that sale together. But then I already working in a role, which back then was more common was called information architecture or information architect. So basically, the person who like takes the kind of holistic user experience into account. So I was kind of working instead of writing code, I transitioned to this role, where I was working on the level of like, sitemaps, and plans and screen flows and wireframes, and that kind of thing. So yeah, I did that for a while. And you know, for these two different kind of early Dot Com agencies. And for various reasons, tired of that, then ended up working for a big agency that was growing in this kind of fast and reckless way. And I decided that I'd had enough of that. And so at some point, I decided to go out on my own. And this sort of begins career number three is when I go freelance, and that was a big scary decision. Yeah, at some point, I decided that I was going to go out on my own. Take some clients with me. And so I continued to do actually freelance for Sotheby's for a little bit. And then around that time, fortuitously, some of the early museum clients I had had, who remembered that I had occasionally done this thing for them called me to do it again. And the thing was, I would occasionally do maps for them. So, for example, there was a collection of Japanese art. I created a simple outline map of Japan. I mean, honestly, I think it was like clipart, or something, I didn't really know what I was doing. But I did a few of these early maps for different museum projects. And some of them remembered that and I started getting calls around the time I was going freelance to come in to create maps for these exhibitions and things. And so that set me on career number three, which is freelance cartographer. So this is when I initially started out doing very rudimentary stuff that I was kind of too embarrassed to even call myself a cartographer. But over a number of years, kind of, like, kind of grew into the role and embraced it and, and became much more serious about the practice of cartography and, and that was, you know, for so for several years, I was doing kind of like a 5050 mix of small web projects on the one hand, and then cartography on the other. And the cartography was typically again, for like museum and art world publishing clients. So yeah typical
projects would be:the Met is putting on a show of art from Mesopotamia or from the Tang Dynasty or something. And so I would go in and meet with the curators and find out what it is they were trying to convey and, you know, do some archival research and find a bunch of public datasets and bring it all together. So it involved this kind of intense data, heavy wrangling stage, and then a design phase. So it was a very gratifying mix of work that kind of, you know, tickled various parts of my brain and my curiosity so. So I did that for a number of years. That was kind of the last thing I was doing before I joined Artsy,
Anna Carey:First of all, the combination of art and data and tech throughout these various touch points in your career is so fascinating. And I almost feel like for a long time, you were destined to work at a place like Artsy that really does combine all of these things. So I feels like it was sort of quietly calling to you, at least throughout these various moments of transition, which I love. And obviously, it sounds like something that you were passionate about. When you were exploring this path as a cartographer, what was the education and learning path for you, as someone who recently learned to program? The overhead and sort of challenge but also exciting, stimulating journey of learning to code is really interesting to me, and how different people have approached that. And I'm interested in being a cartographer, are you totally self taught? Did you take courses? How did you go about learning that skill?
Roop:I did take a course much later, I had been at it for several years at that point, and it was more to solidify things that I had kind of learned on my own, but I had learned on my own was a lot of practical stuff, just from fighting my way through using the tools. Some of it was theoretical reading. So, you know, I did actually read a lot about the history and theory of cartography, but it was all very autodidactic, and haphazard and self taught in the way that many of us are in, like our technical backgrounds. And I think that's the reason why I sort of shied away from even using the term cartographer for a long time. But eventually it fit. I mean, eventually, I was doing the work, and feeling less embarrassed about that labels. But yeah, it was all kind of self taught on the fly. And I mean, one amazing thing about me, kind of making that career move, when I did is that it was the era of big public datasets being shared over the internet. So if I had tried to do that work even 10 years earlier, I don't think it would have been feasible to do as someone who's an outsider, who's self taught. Yeah, but by the time I got started, you could download entire topographic datasets of like the earth terrain from NASA. And you could download historical GIS like data sets of like the evolving boundaries of European nation states or Chinese dynasties. And so all this stuff was kind of, you have to hunt for it. And you had to wrangle it and clean it up and stuff. But it was all available, which meant that there was just like, a lot of room for experimentation and discovery, which probably would not have been the case of you even a few years earlier.
Anna Carey:Yeah, totally right place, right time and sort of this the open nature, I guess, the open nature of the data and also open nature of the internet kind of happening at once, in a way. So obviously, you were at one side, doing this freelance work on the other side, doing this freelance cartographer work. How did that then evolve into you finding Artsy?
Roop:So mostly, I was doing the cartography work. And that was the work I like to talk about, because it was kind of more fun and interesting, but I did also always have a finger in tech work. So I was doing smallish web projects. And many of them were also our domain kind of projects. So for example, one of our current fair partners is the International Fine Print Dealers Association. They put on an event every year called the Print Fair. So I actually was their developer through an agency called Media Combo. And so I worked on that site for a long time and learned about exhibitor lists and floor plans and all kinds of related stuff from that. So that was an example of something I did the very last project I did before Artsy. So I mentioned a moment ago that there was like a a private collection of Japanese art that asked me to do a map for them at the beginning of my freelance career. At the end of my freelance career, that same collection came back and they wanted to produce. So it was called the Burke Collection that was a private collection of Japanese art, the largest outside of Japan. And it was put together over a number of years, but these two art collectors Jackson and Mary Griggs Burke(fun fact Jackson Burke is a printing figure who allegedly brought Helvetica to the United United States decades ago). So they have this amazing collection of Japanese art which upon their death, they bequeath to a number of institutions, including the Metropolitan Museum, Minneapolis Institute of Art, places that they were connected to. So before they split up the collection, they wanted to produce one big catalog raisonn of everything that they had ever. And so they did that. They did this beautiful two volume edition. But they also wanted a website to go with it for all the people who wouldn't have access to this lavish and expensive printed catalog. So I did that. And, you know, I kind of worked with the the catalog team, which has a lot of people I've worked with previously in my design, career. And that involved a lot of wrangling of artwork, metadata, was kind of like the perfect like, you know, on ramp to like, working out Artsy, was the last big project I did remember kind of bringing that in as like a portfolio piece. And for a number of reasons, I was ready for a change in my career. Some of them personal like, having a kid and just wanting a little more regularity. So I was ready to make the jump from freelancing back to a job job. And Artsy, as you said, was calling out to me I had been exposed to Artsy through my relationship with the Print Fair. I had even once wandered into General Assembly to meet somebody else. And Artsy was in the building back then. And I saw their logo, and I don't know, it was I distinctly remember seeing that and wondering, what's this all about? So yeah, as you said, Artsy was kind of calling out to me. And so when I was looking for a job, I sent Artsy a resume cold, didn't hear back at first, because you know, people are busy, it was on the verge of accepting another job, when I get an email from dB. Previous interviewee of yours,
Anna Carey:and former former CTO,
Roop:yeah, telling me to like, you know, stop the presses and come in for a coffee. And that's kind of how Artsy thing got started. So that was career number four, grown up engineer at a product shop.
Anna Carey:But in the art world, still, I mean, something that is so, so interesting. And I don't know if I fully do this about you how deep your art experience is, and has been prior to Artsy but I think that, you know, as we're growing a lot as a team, and hiring a lot more engineers, we're definitely hiring a lot of people who have no background in art, or even in like a cultural space. And something that is really special for me about this role is having the domain and industry experience from working specifically at this company, but it could happen anywhere, but in this industry, and go into galleries and fairs and understanding both the art world but also the online art world specifically. And I think it's really cool that you also had that coming in, I wanted to see for you, how having that domain experience both in metadata specifically, that's more tied to your role, but just generally the exposure to art, how that influences your life at Artsy as an engineer?
Roop:I mean, it helps having that experience to begin with just sometimes like knowing what questions to ask or what things to curious about. I think it also like, both of these things, the fact that I was drawn to that work earlier, and that I was drawn to it or Artsy, or maybe both like symptoms of something else, which is just like OCD about data quality and like an interest in like high quality metadata, you know, is also informed very much like the choices I've made within Artsy of the teams that have worked on. Yeah, there was a theme there. And I don't know how else to explain it other than maybe just like a basic compulsion.
Anna Carey:Yeah. And interest too. I think when you're working, I think engineers work in all different kinds of companies, and not necessarily in areas that they're specifically interested in, is the work itself may or may not, it may not matter. But it definitely, for me makes it more exciting to work in an industry that you care about or type of work that you at least find intellectually stimulating, again, aside from the actual technical work. So that's definitely something that I feel as well. And yeah, something that also came up when you were talking was your work as a cartographer, and how that from a technical perspective is obviously very different is not, you know, it's not the same to be developer in a cartographer is really to these are really different crafts, different pursuits. How has your experience as a cartographer influenced your experience as a developer?
Roop:Yeah, that's a good question. I mean, so one to answer that question is like the very concrete way in which these two things sometimes do overlap. So sometimes I've actually worked on like, mapping apps. So before Artsy, one of my fun projects I did just before joining Artsy was working on a web app that was a history of the street grid plan of Manhattan, which was laid out starting in 1811, by this surveyor named James Randall, this is a project for the Museum of the City of New York involve digitizing all these very old survey maps of New York both before and after the grid was laid down, stitching them together, and making them accessible with all this data indexed on them. And that was on the Museum of the City of New York's website. So that's a very concrete way in which these two things come together. Another example from my time at Artsy would be the City Guide project, which was is our guide to art happenings in six major art cities around the world. So that was a very fun project for me to work on a few years ago. But just, you know, even apart from the actual spatial applications that I've worked on, I guess, the job of a cartographer, in some extent is to help orient and explain and contextualize things and to, you know, educate you about a specific thing, but also give you the broad terrain on which that thing happens. And that's much more abstract. And it's just kind of a mindset that I try and bring to my work as a developer. And sometimes that can mean how you write a PR description or something. So I'm always kind of like, me, not always, but any substantial bit of functionality that I'm contributing in a PR. I'm often thinking, like, Who's the person who's gonna have to look back at this at this in 18 months? And what, what kind of a map would they like to have to this terrain, and to structure my, you know, even PR descriptions around that? Sometimes that's prose, sometimes it's diagrams. So diagramming is like another clear area of overlap here. Some of my greatest hits at Artsy have not been code, but diagrams of various kinds. Maybe in CMS, you'd come across the map of the artwork form, that kind of thing.
Anna Carey:Oh, I have not, but no, absolutely have to show this to me after we talk. That's amazing. I'm sure that will be very helpful for us.
Roop:Yeah. So so there are definitely like areas of overlap. Like whether it's applications or the urge to diagram or just the urge to like help people get oriented and, you know, taking that role seriously, quite apart from like, the actual code we read.
Anna Carey:Yeah, definitely. And over the course of these four different sort of career stages that we've now outlined over the course of this conversation, what do you think is the best decision that you've made in your career so far?
Roop:Yeah. I mean, as you can maybe tell from this outline, I've had this real kind of like, follow your nose aspect to my career. I've never had a five year plan, I've always just kind of gone after the thing that's even most compelling that was just on the horizon. I guess that's a decision of a sort, is to kind of be willing to like be a little bit impulsive. So I don't know, I don't know if that was the best decision, or the worst decision of my career. Ask me again in 10 years.
Anna Carey:Sounds good. Sounds like it's serving you. I think that hearing that as someone who's relatively early on in my career, as a developer, it's really helpful to hear that kind of advice, because I do think amazing things can happen when you're open to opportunities that present themselves without too, too much planning. What about in your work right now gets you the most excited that you're been working on more recently?
Roop:Yeah. So I mean, you can picking up the theme, again, of metadata and high quality data of various kinds. I mean, that's been a theme throughout my work at Artsy whether it was the Genome Project, initially, whether it was the artwork form rewrite that I think we were discussing on that rooftop a few weeks ago, which is the artwork form within our partner facing CMS, which is probably the biggest form at Artsy, and one of the most kind of intense data surfaces we have. And then more recently, like on the team I'm on currently, and we do a lot of work with search and search is nothing if you don't have good metadata. So thinking of the ways in which metadata powers our search experience, these are all kinds of examples of things that get me excited now. And then that sort of relates to another thing that has been a consistent interest of mine at Artsy which is designing for internal users, internal power users and stakeholders. So I actually kind of like working on Admin Tools. You know, one tool that was a lot of fun to work on, and which has proved useful and has had like a number of lives and second lives is Rosalind, which is a Boolean search and batch updating tool for genome metadata for works and has found a number of different ways to be useful as the product has evolved at Artsy. More recently, I've been doing a lot of work with Observable which is a great product. Not an Artsy product that's observablehq.com. It's like a way of creating data driven web based notebooks written in JavaScript. But it's sort of like a way to think with data to program with data. But in a way that gives you all the power of like, the web and JavaScript ecosystem behind it. It's great for visualizations, great for guerrilla Admin Tools. And I've been using that a lot to, to convey and to socialize some of the more complicated ideas behind our like our work search and ranking algorithms and stuff. And that's been a lot of fun.
Anna Carey:And what outside of your work gets you excited right now, now that things are opening up where the world is sort of feeling like it's almost back? And also, if you are doing any other cartography projects coming up to that'd be cool to hear that?
Roop:Yeah, I mean, along with the world closing down the museum world being closed was part of that as well. And that definitely slowed down the amount of art world publishing and cartography and stuff. I did do one cool project during lockdown, which was a map for the DIA Foundation, here in New York City of all their projects around the world. And then more recently, I just got a call from the Philadelphia Museum of Art to work on something for them. So I'm continuing to do that stuff outside of of Artsy, you know, much, much lower clip than I used to, which is only proper, I think, but I still like to do it. It's important for me and fulfills certain kind of itch that I have. I'm also a dad, which takes up a lot of time, you know, can't wait for school to open up again in September. And, you know, and then I have a lot of interests, I guess, you'll find me in certain Slack channels on Artsy talking about music or food or whatever. So, other things.
Anna Carey:Cool. I love that. Yeah, definitely. It's been so cool to hear more of your background, you are absolutely one of the coolest people I've talked to at Artsy. So it's so incredible to hear even more deep into your story. So yeah, we're nearing the end, I'd love to ask one final question. If you could use one keyboard shortcut for the rest of your life, what would it be?
Roop:Yeah, that's the reason I agreed to do this interview. I am here to evangelize Ctrl command space, it is the keystroke, which brings up the Character Picker or the glyph picker, whatever you want to call it on on OS on Mac OS 10. Which, for Mac OS, I guess it's called now anyway. So it gives you access to not just every emoji, but every Unicode character set that your computer knows about. And so you never actually have to remember how to key in any, you know, sort of non Latin characters, because it's always right there. It's just Ctrl command space.
Anna Carey:Well, I am so excited to use this. We're definitely not supposed to play favorites. But that's definitely my favorite answer that I have heard thus far. Yeah, really excited to play with that. But yeah, Roop this has been amazing. Thank you so much for coming on the podcast. It's been great talking to you. And yeah, we'll see you next time.
Roop:Thanks so much, Anna, it was fun talking and see you later.
Anna Carey:And that's a wrap on our episode with roup. As part of our Who are you and how did you get here series. You can follow along with the Artsy engineering team on Twitter at Artsy open source and on our blog. artsy.github.io. Thank you so much to Eve Essex for the theme music that you heard at the beginning and end up this episode. And thank you to the entire Artsy Engineering Radio team, as well as Aja Simpson who edited this episode. We'll see you next week.