Daniel Doubrovkine (aka dB.) is a seasoned entrepreneur, lifetime artist, technologist, creator and maintainer of many popular open-source projects and the Chief Technology Officer at Artsy.net in New York, the largest online fine art marketplace and publication. Daniel graduated from University of Geneva in the late ’90s with a degree in Computer Science.
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The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change by Camille Fournier
Daniel’s Team For Kids donation page (TCS New York City Marathon)
Slava for Strava for Slack (All proceeds donated to NYC TeamForKids charity.)
What I Talk About When I Talk About Running by Haruki Murakami
Transcript, edited for clarity:
Ryan Carson: Change Wave is an exclusive look at real, first-hand stories on how cutting edge leaders rose to the top, smashed through barriers and created real change.
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Today, I’m joined by Daniel Doubrovkine, aka “dB.” from Artsy. Thanks for hanging out.
Daniel Doubrovkine: Thanks for having me on the show.
Ryan Carson: Yeah, I really appreciate you joining us — especially from your highly-technical phone booth.
Daniel Doubrovkine: Yes, we dug out these phone booths in a very tall building overlooking Manhattan. The smallest place with the biggest view.
Ryan Carson: I love it. It’s great. Yeah, meeting space is always at a premium. So, let’s dig right in. Tell us all about your job title and what Artsy does.
Daniel Doubrovkine: I am CTO at Artsy. It’s artsy.net. Artsy started as something called the “Art Genome Project,” a classification system by art historians of contemporary art. So think of an online version of a curated show where you walk into a gallery and see a painting, and maybe other related paintings by other artists that were selected by the curator, so the “Art Genome Project” is a group of art historians classifying works of art, and then the algorithms do the similarity search. So, roughly, it’s a graph of the art world. We get our artworks from galleries, institutions, museums, auction houses, etc. etc.
Fast forward maybe eight-and-a-half years, Artsy is the largest online art marketplace. We have about 3,000 galleries on the platform today, and we have a very large number of auction houses, so if you come to Artsy as a collector, you can inquire on works, you can buy them from galleries, you can bid on day sales and evening sales at various auction houses, etc. etc. so we’re a marketplace. We’re also the largest online art publication, read by millions of people every month. We write about art, and it’s universally loved and long-form interesting content and a news channel.
Ryan Carson: How fun! So, did you have a personal interest in art that lead you to discovering this, or … how did you end up with the company?
Daniel Doubrovkine: I ended up with Artsy by accident almost. A friend of mine called me and introduced me to Carter Cleveland, who was the founder and CEO, and it was a tiny, tiny — maybe five people — company. But I’ve always made art, and lived around art all my life. My father was a translator, my grandfather was a propaganda writer in the Soviet Union, so I was dragged to Bolshoi Theater when I was a kid. So I’ve always had a passion for it. I’ve made art all my life. I’ve been drawing forever, but it’s always been a hobby side project of mine, connecting this to the place that actually cares about art and wanted to bring it online, and has succeeded largely at doing so. It’s been incredible.
Sustainable growth for a hockey stick company
Ryan Carson: Gosh, that’s so cool that you can connect that kind of personal passion and history with your job. So you said you started off when you were tiny at five; how big are you all now?
Daniel Doubrovkine: Artsy has about 220 employees. We have a London office, a Berlin office. We’re headquartered in New York. We have people wherever there is a fine art world. Galleries, museums and so on around the world.
Ryan Carson: Gosh. Wow. I’ll bet over a beer or something you could tell us some stories about scaling from five to 200 plus.
Daniel Doubrovkine: It’s been a slow and steady progress, I think. It’s not the kind of explosive, ridiculous growth of some of the Facebooks or AirBnBs, it’s manageable and it’s good. It’s a solid company that keeps expanding and growing.
Ryan Carson: That’s refreshing to hear. As a kind of side note, I’m really passionate about companies being sustainable and long-term minded, and that’s actually great to hear. I think it’s encouraging to the listeners here, too, that you don’t have to be some sort of hockey stick, rocket ship company. You can build something good that you believe in over the longer term, so …
Daniel Doubrovkine: I mean, Artsy is a hockey stick, rocket ship company, but I was talking recently to someone who works at AirBnB, and they were telling me how they’re seeing hypergrowth ad nauseam at this point and all of the problems that come with that, so we’re certainly not that kind of hypergrowth, where it’s just exponential, every day, nonstop.
Growing from a successful entrepreneur in Geneva to a rank & file engineer in Seattle
Ryan Carson: Right. The good strong growth. Good strong, doing something you’re passionate about. Gosh, we need more businesses like that. That’s really refreshing. I’d love to hear about a story about a time when you encountered a massive barrier in your career, and how you tackled it.
Daniel Doubrovkine: I think a good story about a massive barrier in my career is at the very early time. So I started as an entrepreneur. Before I was old enough, I was running a British Virgin Islands offshore company from Geneva, Switzerland, selling software in the early days of the internet, and making way more money than I’ve ever seen by coding and selling that online. So this is like ’96, ’97. It was really fun, and I had some people approach me and say, “Let’s roll this into a more real company. We’ll write you a check and help us build this other thing.” So I joined the larger startup, brought the technology with me, brought myself with me, brought some of the money that I got from them with me and we saw our company go from nothing to 18 employees in about a year. That has crashed as fast as it grew, and I felt I was really stuck. I felt like I learned nothing, that I failed miserably, that my experience was worthless, and I just felt thrown in every direction.
Ryan Carson: That sounds brutal.
Daniel Doubrovkine: Yeah, it was pretty brutal. Especially coming from a place where suddenly I had a lot of money, and then I had no money at all, and now I’m asking my dad to pay my rent kind of thing again.
Ryan Carson: And so was the hardest part feeling like you had failed?
Daniel Doubrovkine: It was definitely feeling like I had failed but also feeling like “I don’t understand why … what happened?” I think for me, the right answer was truly to reset and go work for a larger company with a more established process and learn everything from scratch. So I got very lucky, and this was 1998. I joined Microsoft and moved to Seattle. I really restarted from zero. I joined as a rank-and-file engineer and learned how the sausage is made at the end to the largest and most successful corporations.
Ryan Carson: Let me dig into that, because that is a big choice to go from starting a company and running a company, going through losing it and then saying, “I’m gonna be an entry-level engineer now and rebuild my career.” Can you walk us through the decision point on that?
Daniel Doubrovkine: Well, first of all, Microsoft was definitely the anti-company I wanted to join. I was the Linux person. Windows ’98 had just come out, it was awful. We all complained about it, so this was not an obvious choice at all, but at the same time, I felt like I needed some structure to understand how actual software in larger organizations is built, because a lot of our failures I thought were structural.
I had no idea what it looked like to be an entrepreneur in the United States, to be a programmer in the United States. I really looked for that experience, and something that I felt was lot ahead of me. So I took a leap of faith in interviewing. I said, “Okay, I’m gonna forget all of my Linux favorites, and I’m going to go and just see what I encounter through the interview.” They were very aggressive at try to recruit people at that time, so all I had to do is say yes to that. But then one thing lead to another, and I learned that I was actually talking to very smart people. I really enjoyed my experience. What they were working on, and what they told me I’d be working on was really exciting. At the time, they were talking about mobile phones. This is when I had a Motorola Startac in my pocket.
Ryan Carson: Yes! I had that phone!
Daniel Doubrovkine: A great phone. Two hour battery life, zero to nine buttons.
Ryan Carson: It’s interesting that you made the jump. Did you have any family or any connections in America?
Daniel Doubrovkine: None at all. I barely knew where Seattle was, but I knew what I was signing up for, and what kind of company I was going to work for. I knew sort of what I was going to work on … it was a little secretive. Actually, by the time I arrived, that project was canned and I ended up working on something completely different.
Ryan Carson: Oh, my gosh. And how was your English?
Daniel Doubrovkine: My English was pretty good. English was my second language, so I definitely could speak English. Maybe now that I’ve been living in New York since 2004, I think my English is much better.
Ryan Carson: I think for the listeners, it could be almost intimidating to hear “Gosh, I just made the jump and I moved to a brand new country.” What was a tactic that you used to push down any fear you had about that?
Daniel Doubrovkine: I think I didn’t have as much fear. I just remembered our old family story from earlier. We immigrated to Europe in 1990 from the USSR, and that was a lot more brutal than my paid move from Geneva to Seattle.
Ryan Carson: Okay, so it was perspective.
Daniel Doubrovkine: I had that perspective. I was interested in a totally new challenge, a full reset. And it took a bit of courage, and then a very welcoming organization on the other side, I would say. So it’s 50/50 me, it’s 50/50 them I think, as well.
Ryan Carson: Right. Wow, so the takeaway is perspective. Throw it into perspective and try to put that problem in comparison to others, so that’s valuable. Love that.
Daniel Doubrovkine: Resetting is something that I’ve learned from. I’ve tried to do it a few times in my career, and I think it’s always turned out to be good. Having that faith, that if I make a choice of taking a step back to take two steps forward, that it will work out.
Key influences on managerial style
Ryan Carson: I’d love to know your favorite book, course or person that’s influenced you in your career.
Daniel Doubrovkine: I’m gonna fast forward all the way and talk about the more recent one that I really like. I’m friends with a very talented leader, Camille Fournier, who wrote the book called The Manager’s Path.
Ryan Carson: I’ve heard of it, but not read it.
Daniel Doubrovkine: Yeah, I highly recommend it. I think Camille was CTO of Rent the Runway, now works for Two Sigma, a hedge fund. But I think it’s a lot of practical and simple advice for managers who are embarking on this track. I’ve read it very recently — obviously in that she only wrote it a couple of years ago — but I’ve got to say that it speaks really clearly the truth about management from an engineer’s point of view. Camille’s a very talented coder, she’s an Apache contributor, and she was and is an important New York technologist. I think that book is a good representation of what happens in the real world. I would highly recommend that.
The importance of “ass hours” and patience
Ryan Carson: Next question is what is the funniest, worst or most interesting job you’ve ever had?
Daniel Doubrovkine: Funniest, worst, interesting job. Okay, I have a few. My first day job was delivering pharmacy. I was like 13, 14 years old with a bicycle, delivering pharmacy stuff. I realized that pedaling around the city was not for me. Then I worked in a computer store for a while, but I got this offer to do a summer internship at a bank. It was paid much, much better than all my previous jobs, and it had to do with computers. At that time, I had no idea what computers were or very little idea what computers were. So I was like, “great, computers,” because it was actually, I think, in the security department or something like that. “It’s a bank, sounds amazing, let me put on a shirt and pants and go to work 9 to 5 at this bank in Geneva to do something with computers.” My job was to take stacks of papers that had columns with numbers and basically debit credit, and copy them into Excel.
Ryan Carson: No!
Daniel Doubrovkine: All day long for 9 hours a day.
Ryan Carson: God. That’s brutal.
Daniel Doubrovkine: So I would make a ton of mistakes. And I would have to go and check. It’s very hard to do by yourself because you have to read two sets of numbers; one from the screen, one from this paper that is handwritten by bankers.
Ryan Carson: Wow.
Daniel Doubrovkine: And try to add them up and get to some kind of result. Then somebody would check them and there’d be a mistake. And then I’d have to redo it.
Ryan Carson: Bad.
Daniel Doubrovkine: That was the most hilarious, I guess, or the worst.
Ryan Carson: How did you stay sane? I mean, what did you…
Daniel Doubrovkine: You don’t. You don’t stay sane. You just …
Ryan Carson: Slowly go crazy.
Daniel Doubrovkine: … hope that your next job will be copying architecture diagrams.
Ryan Carson: Wow. What’s cool about that story is, I mean, that’s a super menial, terrible job. Yes it’s information work so at least you’re not in a mine or something. But now you are a CTO at Artsy, and I think it’s cool to see that path.
Daniel Doubrovkine: Well, it’s interesting that you call it a path. I don’t think I’ve had a path of coming from a place where I’ve copied Excel spreadsheet data into being a CTO. It was not as continuous as it seems. I don’t recommend starting there.
Ryan Carson: Yeah. Well, but it’s neat that it happened. Actually, I’ve interviewed probably 55 or 60 people, and almost everybody has a similar story. I mean, they started off somewhere unbelievably low. So it’s a testament to your hard work, luck, drive, that ended up getting you there.
Daniel Doubrovkine: Thank you. I certainly learned the ability to just sit down and do something for hours at a time.
Ryan Carson: Yeah. Discipline.
Daniel Doubrovkine: I applied this in college when I was studying math. We call this, if I may, “ass hours.” It’s all the hours you sit on your behind and do something for a duration. And you just put this information in your head.
Ryan Carson: Yep.
Daniel Doubrovkine: That’s my first encounter with needing to just repeat something for a very long time to get it done. I learned a lot of patience in doing practical, hands-on exercise. Coding can be a little bit like that sometimes, except it’s much better than copying data from a-
Ryan Carson: Hopefully!
Daniel Doubrovkine: It’s certainly more creative.
Ryan Carson: Certainly more creative, yeah. I do think you’re speaking to this basic ability to be disciplined. I’ve learned this more recently in my career, unfortunately, and found just the discipline to not quit on something that is boring and is daily, ends up yielding massive results. You learn that. So I need to have my kids work at a bank and copies.
Daniel Doubrovkine: I’d like my kids to do it, I’d like that for sure. Actually, now, thinking of the Art Genome project at Artsy, I learned that is a lot of value in humans, and what we otherwise want to solve with automation. I think there’s a lot of things we can solve with automation, such as copying data OCR style into a spreadsheet, but there’s a ton that humans can do really effectively when we need the true brainpower of individuals.
The two most important lessons for your life and career
Ryan Carson: I’d love for you to imagine a time where you could go back in time to a younger dB., I’d love to know…you hop out of that time machine, you get out and you grab the other self by your shoulders. What would you say to yourself? What are the two lessons you would say?
Daniel Doubrovkine: I think I pursued a shortcut from my first company too quickly. And I would like to shake myself and be like, “Just keep doing what you’re doing. You have something successful.” I didn’t have a mentor or somebody to tell me, “look, what you have is unique.” Nobody was understanding the internet at that time, at least not around me. Nobody cared. My parents would yell at me to get away from the computer. Nobody understood what I was doing. I had real people paying real money for a unique ability to write software. I was ahead of the game quite a bit. I think I pursued a shortcut into associating myself with lots of other people that had a vision that I really didn’t care as much about. So instead of continuing my own thing, I continued somebody else’s thing that was not successful.
Ryan Carson: Wow, so the lesson’s almost an amount of having self-belief, or trusting your gut or something? ‘Cause how would you know that you had it?
Daniel Doubrovkine: You don’t know, but the symptoms are there. I think you have to surround yourself with people who are really smart, and who will encourage you to say that you actually have it there. “There is something here. You should continue doing what you’re doing,” or tell you, “you have nothing here and you should walk away from the thing that you’re doing.” I’d say that’s one moment where I would go back and tell myself to just persevere at the thing that’s already working. It was doing so well.
Ryan Carson: Wow. That’s valuable. How about the second thing?
Daniel Doubrovkine: The second thing, it’s interesting. I think in the more recent years, seeing company patterns internally, we have made, a few times, the same mistake. I wish I could go and tell myself to raise some of these issues more strongly, and go back a few years and say “This particular thing that we are going to do again is not going to work. We’ve already failed it the same way. We’re just repeating our own mistakes. Here is a pattern.” and maybe try to explain to myself not to be so adamant about it and internalizing those frustrations but more like thinking about “how can I constructively lay them out to my executive team in ways that they will actually relate to, understand, and hear?”
Ryan Carson: Right. Almost dispassionately kind of separate yourself and say, “Let’s do this.”
Daniel Doubrovkine: Starting from the place of what is the best for the company and aligning everyone to the outcomes that we want, and then going back and thinking about what we should be doing differently this time so we get a different outcome. ‘Cause we are repeating doing the same thing multiple times and expecting different outcomes is probably not gonna work.
Ryan Carson: Yeah. It’s the definition of madness, right?
Daniel Doubrovkine: That’s right. You said it.
Running from Bed-Stuy to the Village
Ryan Carson: I’d love to hear a story where you caused significant change in your personal or professional life.
Daniel Doubrovkine: That’s interesting, a story where I have caused a significant change in my personal or professional life. About two years ago, I went through a lot of personal issues, family related stuff, and so on and so forth. I ended up needing to commute to Brooklyn on a regular basis to the depths of Brooklyn. Brooklyn is wonderful, but Brooklyn is very big. I ended up having to go every once or twice a week to somewhere in the depths of Brooklyn and on my way back from there, I started having a pattern of meeting my friends in Bushwick that are all artist type people, so they don’t have hours. They party all the time. There’s dancing. There’s great music, alcohol, everything in-between that you can imagine. Super fun, except I’m no longer 25. I’m 42. This pattern became sort of destructive, rather than constructive and enjoyable.
So, I started feeling bad about my repeatable pattern. I started running, and I decided I was going to run from Bed-Stuy in the depths of Brooklyn, back home to the Village, where I live. I thought, “Okay, I’m gonna run to the Manhattan Bridge or Williamsburg Bridge first.” I ran and it was slow. It was hard. I managed somehow to get to the bridge. I thought I was a hero! Next time, I went and ran on top of the bridge and I thought I’d really made it. But then I realized that there’s the other half of the bridge so the third time, I ran over the bridge — and then eventually, I was able to run to home. I started running with an app and measuring myself and I realized it’s only three and a half miles to the bridge and it’s only seven miles home.
Long story short, I kept at it and really pushed it and running my first marathon this year, the New York Marathon. In about six weeks. I’m running for charity, actually. I’ll shamelessly plug my charity, Team for Kids. You can find me online and there’s links to that charity.
Ryan Carson: How cool. Team for Kids.
Daniel Doubrovkine: Yeah. It’s a great charity in New York. It’s the default charity of New York Road Runners. If you’ve never picked up running, I’m now totally addicted to it. I use some of my computer skills to help. I wrote up a Slack Bot for Strava, so you could repost all the runs or rides to Slack. We have a channel at Artsy called Distance, where people connected using this bot … connected their Stravas through it and you just encourage other people to run. It’s available. It’s called Slava.
Ryan Carson: Slava. I love it.
Daniel Doubrovkine: It’s not free. I have to pay for service, but 10 bucks a year, you can get the same integration.
Ryan Carson: How interesting. So, if I was to extract out, why that change is significant, you basically started seeing patterns in your life you didn’t like and then you thought, “Well, I’m gonna try to change them, but I’m actually gonna change them a little bit at a time. I’m just gonna run to the bridge. Okay. I did that. And then I’m gonna run half way. I did that.”
Daniel Doubrovkine: I thought I could run a marathon every time I would sit with my beer watching the New York Marathon run by. Like, how hard can it be? I didn’t know how far I was gonna get and I thought I was getting really far running to the bridge. It’s just that, it was only three miles. Tells you how out of shape I was.
Ryan Carson: Yeah. I went through a similar running journey where I started walking and then ran a little bit and all of a sudden, your body has this crazy ability to then keep running, which you didn’t think you had.
Daniel Doubrovkine: Right.
Ryan Carson: How do you integrate into your day? Do you actually run with your laptop in your backpack? Or, how does that work?
Daniel Doubrovkine: No. I think running with a laptop in your backpack is awful.
Ryan Carson: That would be terrible.
Daniel Doubrovkine: It’s terrible for your laptop. I actually like running completely disconnected. I got the running watch to be able to only have running time and pace and stuff like that. But, I run with no phone. No connectivity. I leave with no money and nothing in my pockets and I do a 10 mile run around lower Manhattan, for example. Or at Central Park. Run around Central Park, which is an amazing run in New York. We have such a good pedestrian city. You can run in any direction fairly easily. Run in traffic. Run at night. Run with cars. You name it. This is my time to disconnect now. I try to carve morning time from my meeting schedule and try to push my meetings as late as possible so I can accomplish that early. I don’t run every day, but I make the time to be completely away from work, from the computer.
Ryan Carson: That sounds so good. Yeah. I just meditated for the first time yesterday. It was shocking. Ten minutes where I’m just listening to my breath.
Daniel Doubrovkine: Yeah. It feels amazing. Maybe you’re on your path from meditation to going to Burning Man in a few years.
Ryan Carson: Uh, no. But, that sounds fun.
Gosh, well, thanks for sharing that ’cause I think hearing the journey from never running to now, it’s an integral part of your life, is the fascinating one. Because, we see people on Instagram and they love running and they look amazing and you think they were always like that. You just shared the story of no, you basically, got there.
Daniel Doubrovkine: Yeah. I would recommend a great book by the author Murakami, What I Talk About When I Talk About Running.
Ryan Carson: I’ve heard of that.
Daniel Doubrovkine: It’s a great meditation on running. He wrote so many fiction books that are very whimsical and mesmerizing. But, this one is almost a documentary about how he feels about running. If people need convincing, I would read that. It’s a good story. I just got addicted to it. It might not be for you or for whoever is listening, but trying and persevering and breaking through some of the early barriers is the hardest part. The next hardest part seems to be the marathon, but if I don’t die during it, I’ll tell you all about it.
Ryan Carson: All right. Cool. I’m gonna come back and check. I hope you don’t die.
Daniel Doubrovkine: I hope so too. It seems implausible right now.
Ryan Carson: Yeah. Hopefully. Well, I’ve really enjoyed hanging out. I appreciate your time. If the listeners wanna find you online, what’s the best place to do that?
Daniel Doubrovkine: My Twitter handle is dblockdotorg. I generally go by dblock everywhere: Website, dblock.org. Run.dblock.org, art.dblock.org and so on and so forth. Another way you can find me is Google “tallest engineer at artsy.”
Ryan Carson: Really? Are you super tall? How tall are you?
Daniel Doubrovkine: 6’6″.
Ryan Carson: Wow, okay. I’m 6’4″, so you beat me. Way to go.
Daniel Doubrovkine: It’s hard to see on video.
Ryan Carson: I know. Well, dB., it’s an honor to meet you and hang out. Thanks for being so transparent with your story and congrats on all your success at Artsy and in life. To remind everyone, what was the non-profit you mentioned so people can give?
Daniel Doubrovkine: It’s called Team for Kids. If you’re supplying links, go to my website. There is a link on the front page. If you can’t find it, I’m happy to e-mail it to you. It’s on the bottom of all my e-mails too.
Ryan Carson: Perfect.
Daniel Doubrovkine: I’ve spammed the world!
Ryan Carson: Yeah, good. For a good cause.
Daniel Doubrovkine: Yeah.
Ryan Carson: All right. Well, thanks again for you time and we’ll look forward to keeping in touch. Take care.
Daniel Doubrovkine: My pleasure. Thank you so much. Bye.