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Inside Out at Oopsmark


February 24, 2017  |  By Blair Smith

Their leather bicycle wine rack exploded the Internet. You might have seen it on Design Sponge, Wired and Vanity Fair. It’s a simple product that helps cycling be sexy. Oopsmark is in the early days of its journey to create beautiful, useful products that make your life better. We go inside the Montreal-based company to get brand and business insight from Jesse Herbert, Founder and Designer; including why looking like a banana isn’t good for anybody involved with city cycling.

What was the spark for Oopsmark? The ah-ha moment?

Our first product was the bicycle wine rack. The short story is I created it for fun as a bit of a joke based on a random request from somebody. The long story is that I had made close to 10,000 things for a couple of years as a leather artisan at street fairs and music festivals. My goal with making is to simplify things to their essence.

Soon after I added the bicycle wine rack to our Etsy shop, it exploded on the Internet. Design Sponge featured it which generated 3,000 Tweets the first day. It’s also been covered by Wired, different wine magazines and gift guides. This product travelled organically around the Internet. From all of this, Oopsmark quickly transformed my idea for this one product into an actual business. The bicycle wine rack is still Oopsmark’s best selling product.

Jesse Herbert in Oopsmark studio

What is Oopsmark’s mission?

I left a lucrative career in engineering to pursue a dream of making things that I wanted to see in the world. That’s what Oopsmark is all about. The mission for Oopsmark now is to build a company that brings this dream to life each day. It’s not much more complicated than that.

Specifically, we solve problems that make people’s days better. This means actually bringing new ideas to life. It’s both going through lots of different thoughts and triggers to come up with an idea to create; as well as innovating on existing products to make them better.

What does the name mean?

An oopsmark is a happy mistake. So it’s a constant reminder that what we do is about the process. Some things will stick and some won’t. That’s fine. We don’t have control over it, the market does. But we need to be comfortable with the inherent messiness of invention and innovation.

How does Oopsmark stand out in the market?

Oopsmark is based on a couple of principles. First, everything we do has to be simple, bold and elegant. Second, our products have to be innovative in a way that nobody has done before. I want to be on point with what I’m passionate about and hope this resonates with who we collaborate with and the market.

Personally, I’m motivated to make everything useful. It’s a long term play of creating truly useful products. I’m a minimalist and don’t want to create garbage. In the beginning I made more fashionable things. But now I want to design enduring products that make people’s lives better.

Value is important. Oopsmark will be successful by creating high quality, innovative products based on core design principles.

What problem does Oopsmark solve for city cyclists?

How to make cycling more convenient in terms of how to carry things. How to make city cycling fit into your everyday life. Our bicycle wine rack helps cycling be sexy. It helps you get invited back to the dinner party. It helps you enjoy more time picnicking in the park. It isn’t just a product, but a way to improve quality of life.

Our U-lock holster solves a genuine problem that people can’t elegantly carry their lock when they’re riding their bicycle. It’s not a solution for every cyclist; however for many people this is now the shortest route to getting their lock. Hopefully this makes cycling more comfortable and convenient.

Oopsmark-Bicycle Wine Rack and U-Lock Holster

What are you working on right now that’s really exciting?

The urban bikepack is based on a need I had that wasn’t being fulfilled by a product in the market. This product has made city cycling better for me. Now I show up at meetings and people say “Wow, nice bag and briefcase!”. People stop me on the street and ask where I got it. A lot of people buy the urban bikepack to use just as a backpack. People in the cycling industry are addicted to backpacks.

We’re now actively working on improving the design to both refine the features and also to produce it more efficiently while not compromising on design. Our goal is to deliver style and construction quality you won’t get from a bag that’s made in China.

What was a recent challenge that you overcame? What did you learn from it?

Being an entrepreneur is the opposite to how we’re taught to learn in school. People give you problems and how to solve them. As an entrepreneur you’ve got a million problems and need to be focused on how you invest your time. You need to have goals and make an intentional plan.

The challenge is to remain focused on doing fewer things better. Task switching makes you lose focus. I meditate and break up my daily routine into different chunks of work. This helps me be as clear of mind and grounded as possible vs. being scattered, reactive and spreading my effort thinly across too many tasks.

Oopsmark workshop

What keeps you up at night?

Everything. I have a very active mind that’s always trying to solve problems. I like to iterate on things to make them better. This often happens at night. However, what helps me sleep is cycling. When I go bike touring and drop into my hammock at the end of the day, I’m out almost instantly.

How do you see Oopsmark’s impact in the next few years?

A little less niche. Creating products that apply to more people. And having some core products that can be made more consistently at scale. We have large reach in the cycling community, which is great and definitely a core area of focus. Eventually it would be great to have products that you can find at a store like MEC.

Right now we’re pretty international with good brand recognition which always surprises me. If I’m on an airplane and tell people what I do, many people actually know of the brand mainly because of the bicycle wine rack.

What’s another brand/organization/person you’ve got your eye on doing exciting things for city cycling?

Copenhagenize is high up there. It’s an organization that’s changing city cycling infrastructure in a sustainable way. If you build it, they will come. They’re doing this. Ultra Romance is an interesting guy who’s huge on social media for his adventurous nomadic  cycling and outdoors lifestyle. Fitz and Follwell runs cycling tours and bicycle rentals in downtown Montreal. Shea is a good friend. His company is creating some amazing, authentic city cycling experiences.

Any final thoughts?

Looking like a banana doesn’t sell the cycling lifestyle. It’s like bad feng shui on your eyes. I think this is one reason why people don’t like cyclists, or don’t cycle more often. But you don’t have to look like this. I wear the same clothes in a meeting, to the bar or when cycling. I live in Montreal which has some high style standards. You can’t get away riding around in fluorescent cycling gear. The industry needs to create better fashion for a regular way of life. The sport cycling market is declining, but city cycling market is growing. Hopefully this doesn’t mean more fast fashion because that doesn’t jive with the concept of cycling.

Looking like a banana doesn’t sell the cycling lifestyle. It’s like bad feng shui on your eyes. – Jesse Herbert, Founder and Designer


(Images courtesy of Oopsmark.)



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