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Droplr + Designer: Jesse Bennett-Chamberlain


It’s easy to fall into a rut. Same style, same technique, same result. It’s only when you (or your client) pushes that things improve. Web designer Jesse Bennett-Chamberlain has always pushed himself to achieve new heights, taken on challenging projects. His work is marked by clean typography, pleasing textures, and rich colors. But ultimately he adapts to his clients needs, creating sites that fit their brands without imposing his own style. It’s a unique and valuable talent, one he’s built a career on.

His Grimsby, Ontario-based firm, 31Three, has produced some truly stunning work for famed piano makers Steinway, Universal Studios, and even Red Hot Chili Pepper drummer Chad Smith. He’s done everything from site design to print materials to iOS apps. He is living proof that a jack-of-all-trades designer can achieve true success.

How did you get started in design?

I didn’t have any formal training. I was doing work with a friend of mine—posters for a church and a youth group. Somebody at the church noticed them and asked me to apply for a design job at the local newspaper. I spent a week learning Quark Xpress and everything I could about design. Somehow I landed the job and winged it until I figured out what I was doing. I stayed there for three or four years. By the end I was taking on a lot of side projects and I had to make a decision. Either I go full-time freelance or stop doing the side stuff because it was getting to be too much. My wife encouraged me to give it a shot. At that point we didn’t have much in the way of expenses, so it was low risk. I’ve been doing that ever since, for 12 years now.

Have you always been into design?

In high school, I thought I was going to get into illustration, into fine art. My friend that works with me now, Drew Warkentin, sat beside me in art class. We had a friendly competitive thing going where we’d try to outdo each other with our work. At the same time another friend of mine was training to be an Industrial Designer and needed some help on his projects. I would go to his place from time to time and play around on his PowerPC. I slowly learned my way around Photoshop 4 and at the same time started to pick up an appreciation for graphic design. I wasn’t any good at it mind you, but I appreciated it. This was a few years before working at the newspaper.

Did you grow up doodling?

I was totally into drawing as a kid. One of my earliest memories was when a friend of my mothers asked me if she could have a drawing of a chicken that I had made. I remember thinking that I didn’t do a great job on it and wondering why she would want it. A year or so later my mom and I visited her studio in Toronto where I saw my drawing of a chicken framed and displayed on her wall. I might have been 6 or 7 at the time, but I remember it really making an impact on me. I remember wanting the drawing back. (I still sort of do.)

When did you start getting into art?

From 9 to 16, all my time was spent on my bike. I was totally into freestyling. Everything was about freestyling. Drawing was something I did, but I wasn’t super focused on it. I’d mainly be drawing people freestyling. In high school I started to pay attention to it a bit more. I got into painting, photography, playing with all the visual arts. When Drew and I connected in art class, things started to click and I became a lot more focused on working on refining my skill set.

Who were your big influencers?

The guy who got me the job at the newspaper, Robert Woodhouse. He’s a really good designer and very versatile. He doesn’t really have a distinct style. I appreciated that about his work. Michelle Sharp as well. I’d often catch myself thinking, “What would Michelle do here?” while designing at the newspaper. Those were my earliest influences. After that, Cameron Moll has been one the biggest influences on me as a designer. We first met on the forums back when it was the place to have your work showcased. He’s a long-time friend and somebody that’s always been a few steps ahead of me in his career and talent level.

Where do you find inspiration when you get stuck?

Book covers. They’re just amazing. When I go through book stores, just seeing book covers blows me away. The amazing solutions book designers come up with are fantastic. Band posters, illustrations, stuff that’s outside of what I normally do. It makes me think differently and keeps me inspired to keep creating new things. Lately I’ve found Pinterest to be a really inspirational place to visit. I love seeing a stream of interior design, product design, and graphic design all mixed together.


When you work in one medium a lot, do you get stuck?

Yeah, for sure. It’s easy to go with what you know works and get lazy at times. To play it safe. Every designer has a bag of tricks that they pull from, but it’s important to take an inventory every now and then and make sure you’re still growing. Sometimes it’s a client that pushes you a bit further. Working on the Steinway website, I wanted to push it a little bit further because I was working with a company that pushes their product so far, it encouraged me to do the same.

Was that one of your biggest challenges?

The Steinway site was one of the best and most enjoyable sites I’ve worked on, and it was also a bit of a challenge. I felt like I had been given this tremendous opporunity and that I didn’t want to mess it up. It was intimidating and exciting at the same time. Maybe one of the most engaging projects I’ve had the opportunity to work on.

What was it like working on the Chad Smith app?

I mainly communicated with Chad through his agent. Every once in a while I’d get a forwarded email from him through his agent. It was very much what you would expect from Chad Smith. When I was reading up about him, people would refer to him as a monster on the drums. I read in one interview that he had to have custom microphone clips made because the standard ones would shake loose because he hits his drums so hard. A theme started to develop while reading that Chad was a monster on the drums. Between that and the massive octopus tattoo on his leg, the design direction for the app wasn’t too difficult to find.

Are you excited about any design trends?

Not sure if this is the right name for it, but I really love looking at low-poly 3D artwork. Every time something in that style pops up in Dribbble or Behance it grabs my attention. I love it. That being said, I try not to get too caught up in trends when it comes to client work. Obviously easier said than done.

I recently found a project I worked on 10 years ago for a company called Elegant Plaster Mouldings. Most of the site feels like it would still hold up today, except for my odd decision to use pixel fonts in the nav. At the time, pixel fonts were all the rage, and I would work them into every project I could. My love for the pixel font trend clouded my perception and ability to make the right choice in type for the project.

A goal of mine in design is to stay true to the brand I’m working on, regardless of the current trends.

Do you have an overall design philosophy?

This is one of those questions that makes me wish I had gone to school for design and learned to articulate what it is that I value in design. I’m sure I do have a overall design philosophy, but it’s something that I follow based on instinct and gut reaction versus process and rules. I’m not sure if that’s something I’m overly proud of… it’s just what it is. I sometimes feel like the more I grow as a designer, the less I know.

Any advice for web designers?

Invest in your portfolio, it’s the most valuable thing you’ll possess in your career. When I was starting out I often “lost money” on projects because I spent more time on them than I was getting paid. You can see it as losing money, or you can see it as investing in your portfolio. Once you start to piece together a decent selection of work, make sure to actively trim it back and only show your best work and work that you would like more of.

What are you working on next?

I’m currently working with on a number of different projects. Hopefully I’ll be able to share some more of my work there soon. A couple weeks ago I took a small break from that to work with a large TV network on some conceptual stuff which was a lot of fun. Unfortunately I may need to wait a bit to show those comps as well.

Another small side project I’ve been toying with for a couple years now is a reprint of a book from 1900. I live in this small Methodist campground from the 1800s called Grimsby Beach. It’s a really unique community filled with vibrant gingerbread cottages on the shores of Lake Ontario. Every summer in the late 1800’s, steamboats would come in from Toronto with Methodist campers. I love the history here. This book captures it beautifully and I would love to bring it to life again.