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Known by his 173,000+ followers as @drawbertson, Donald Robertson is in a league of his own, famous for his witty, “tongue-in-chic art” and cartoon-like depictions of everyone from Anna Wintour to Kanye West. Presently the Creative Director of Estée Lauder, the Canadian-born artist’s career has spanned the cosmetics and fashion industry, from serving as Creative Director at MAC Cosmetics in Toronto to launching American Marie Claire and redesigning American Glamour with Condé Nast and Hearst. His creative partnerships have included names such as Giles Deacon, Brian Atwood, J. Crew, Smashbox and Bergdorf Goodman. In 2012, Robertson brought his compulsive drawing habit online, sharing work that spans genres, techniques and mediums, attracting thousands upon thousands of loyal followers and earning him the recent title “Instagrammer of the Year” by the Council of Fashion Designers of America. We sat down with the “insta-artist” and father of five to discuss his creative inspiration, upcoming collaborations and more.

What does a day in your life look like?

I get up around 4am and start working on all my projects in my art studio. My kids usually thunder in around 6:30/7am. Then, I’ll head into one of the offices at Estée Lauder, and that’s the beginning of my day. When I had my first child, I realized that the only way to deal with the whole sleep deprivation thing was to fully embrace it, because there’s nothing worse than lying in bed with somebody trying to open your eyes.

You’ve been called a “roving creative director.” What was the turning point in your career that allowed this kind of freedom?

Blog_DonaldRob_2What happened was, social media became this thing. We all used to live and die by print — getting everything ready for print, preparing ad campaigns for print — it was ‘print print print.’ Now, with all these new channels, we controlled things ourselves, relying less on a magazine or news station to declare that we were ‘relevant’, or ‘groovy’, or ‘happening.’ Now, we’re able to make our own audience, have our own following and create our own universe. Then brands realized that they needed to start operating like this as well as a full-on living, breathing thing. It can’t be just one ad campaign that comes out in the March issue; it has to be every single day.

John Demsey, the president of Estée Lauder, is the king of what’s new. He realized very early on that this sort of audience wouldn’t affect what I do — it would actually enhance what I do. Now I work on core Lauder brands but, at the same time, I mess around in my art world, because there’s a lot of overlap. For instance, when I have an art show in Colette, Paris, Smashbox and I will launch a little Donald-Smashbox lipstick. Then it becomes an artful event that doesn’t have the stink of being wholly commercial. I’m able to say, “Hey guys, come look at the art. Buy a lipstick.” The whole universe changed, and it continues to change every day, but this has been the best for me because now I can serve both worlds.

How is social media influencing the art world?

There isn’t any one world anymore: an art world, a fashion world, or a music world. It’s a giant mash-up. Whether you like Kanye’s show or not, that was performance art with a fashion show, and he released an album. That kind of crazy mash-up of all these worlds is what’s going on right now. That’s what I really like about it, that all these things are colliding.

Why has Instagram proven to be the medium for you?

It’s the ultimate archive for me. I can organize everything and keep everything stored on my phone. Snapchat doesn’t interest me as much because everything disappears. I really like having this archive to refer back to because I use it to improve my work. For example, I’ll go back to a painting from two years ago, and I find this makes me a better painter. Instagram also functions as a focus group in that I get a feeling of what’s going to work and what’s not going to work. It’s the perfect medium for me.

Blog_DonaldRob_3You chose L.A. to set up shop and life. Why is this the place to be now for art and fashion?

There are a couple of things. There’s a shift. The YouTube world has literally pulled the power away from New York to L.A. Sephora is a monster and is based in San Francisco. Looking at all the super new, successful beauty brands right now, they’re all coming out of Los Angeles. L.A. is also very close to Asia, so you can fly back and forth very quickly. In the beauty world, it’s all about your proximity to Asia. Plus, there’s no Polar Vortex. I can be in shorts and bare feet, covered in paint in the art studio in my own backyard, which is an almost impossible find in New York.

Tell us about your biggest influences and inspirations.

One of my favorites is David Hockney, from everything he wore to everything he represented, and he’s a really good drawer and painter. That’s a big inspiration not only on how I live but also where I live and why I moved [to L.A.]. The other thing is, I love all the people in the world who make stuff for a living — people who literally make things — like Giles Deacon makes clothes, Clare Vivier makes bags, my friends at GlamGlow make mud masks. There are so many kids in college who think they have to be finance wizards who rig or trick the system to make a living, but you can just make things and do really well. It’s almost become something that people don’t really think about. Anybody who makes anything, those are the people who inspire me and who I champion.

You incorporate your children into your work, bringing that human element, and you urge people to keep their childish instincts. How do they inspire your work?

The day my oldest son made me get an iPhone, my wife gave birth to twins who were a complete and total surprise. That was a coincidence — the two things just landed in my life at the same time. Then I mashed it all together, despite every single person telling me that I shouldn’t combine the two, that I would depreciate my art, that it would be too “daddy blog” and that I would lose high-end fashion followers. I didn’t care. To me, they match up together perfectly. If it were just all paintings, that would be such a drag.

Blog_DonaldRob_4What’s the best part about what you do?

My favorite thing is that I don’t have to edit, and I’m in control. My phone is my gallery, it’s my agency, and it’s my archive. I’m in control of my situation now. In the olden times, you’d have to wait for your magazine story to come out, whereas now I’m dreaming live. Now, it doesn’t have to be about one thing; I can do a million things a day.

You’ve talked about working with your friends and the importance of collaboration. Why is this so important?

It makes things easier and more fun. It doesn’t get all “lawyer-y” because it’s all “friendship agreements.” You end up promoting one another in a more organic way, without feeling forced or fake. You want your friends to do well, and your friends want you to do well. It just works. In life, you meet someone at a dinner party and hit it off. The next day, they call and ask, “Want to do some shirts or clothes together?” You say, “Sure, that’ll be great.” The next thing you know, you have a whole line with Alice and Olivia, and it’s being Instagrammed by some Asian blogger who has nine million followers. It seems genius, but the way the whole thing happened was just casual and friendly.

Can you tell us about your next collaboration?

I’m doing these fun things with Assouline, whose aesthetics and world I love. I’m painting all over their book covers, then we’re selling them as works of art, like new coffee table books. I’ve also been working on secret products with Lauder coming soon. I really like the Streicher sisters in L.A., and I’m using their space as a pop-up gallery. And I just did a really fun collaboration with Zoolander, which is growing into more projects with Paramount. Everything else is still too secret to say yet, but a lot of fun stuff is on the way.