Career (In) Design: A Conversation with Benjamin Edgar
On selling out, scaling creative work, navigating design in the age of AI. I learned a lot.
Design touches everything. It’s essential to the human experience, and it takes endless forms. What fascinates me most are the people who’ve managed to build a career out of making things, whether physical, digital, or somewhere in between.
This series is about their stories, their processes, and the choices behind the work.
For now, these interviews are free to all subscribers. As I ramp it up, full access—including the archive, vintage finds, and more—will be available to paid subscribers for $6/month or $65/year, with a 7-day free trial if you want to test the waters.
I hope you enjoy!
I first heard about Ben Edgar back in high school, somewhere around 2009, through a friend who was always ahead of the curve when it came to design and fashion. I’ve followed his work ever since.
Over the years, I’ve picked up a few of his pieces, The Internet Times hat (we need a restock), the Switzerland Chicago hat, the Knock Cardholder. All things I use regularly, all things people constantly ask me about. That small act of subverting the objects we interact with every day, that’s what I love most about Ben’s work. It’s thoughtful but doesn’t take itself too seriously. Playful, intentional, and always a little unexpected.
We met on a weirdly warm spring morning in Chicago, grabbed coffee near the Merchandise Mart, and sat down to talk.
What you do now you call it the object company - you’ve blurred the lines between art, commerce, and utility. For someone encountering your work for the first time, how would you describe what you do?
I’ve been doing this for well over six, seven years and I still struggle with how to describe it. I could say it’s a home goods company, but that feels a little short. I could say it’s a fashion company, but that’s not really accurate. We’re not really sure how to describe it.
The phrase I’d like to start using is an old term called applied arts - taking the emotional part of art and applying it to useful objects. But I tend to just show the work as a way to describe it.
You launched The Brilliance in 2005. Before Substack, before Instagram, before building an audience online was a strategy. What drove you to put your thoughts online back then?
Chuck and I would email each other constantly. It was just faster to email at the time. This was before carriers allowed cross-carrier text messaging. It was this constant stream in the background about architecture, food, fashion, art.
Chuck suggested we start a blog, which started off short-form about those topics. What changed was when we started doing interviews - because that was effectively these people co-signing us.
In terms of why we wanted to do it… I would chalk it up to just youth. When you’re young, you don’t think about how it will be perceived. You just want to share.
Do you think it is imperative for creatives to be online today if you want to build a design business?
As I’ve gotten older, I see it as a necessary evil. On the internet back then, you had to go all over to find information, it was self-prompted, what sites you looked up. Now we’re consuming so much through such a narrow channel. Instagram, TikTok, Substack.
I think it’s a required thing to do, but you should try and have as much fun with it as possible and be as creative as possible. I’m not big on following what the algorithm wants me to do.
It’s kind of like an adapt-or-die thing. For me, I see it as the only way to get my ideas out into the world.
I know exactly what you’re saying. Going back to The Brilliance, it was like we were peeking over the fence into culture that we were interested in. When we started interviewing guys in the industry, it was almost like they said, “you can come over the fence and hang out with us.”
Which was unexpected for me, but it was my way of getting in back then. You kind of gotta buy a ticket to the show you want to be in.
Looking back, were there moments where timing played a role in your success? Do you think good ideas fail more due to bad timing or bad execution?
This is something that only made sense to me later in life: timing really does matter.
Bill Gates has a great quote (paraphrased): if I was born three years in one direction or three years in the other, there’s a good chance none of this would’ve happened at all.
I think execution is the foundation of everything, regardless of whether your timing is off. You should have an internal compulsion to create really, really great work and execute really well, so you don’t wake up in the middle of the night thinking, “maybe this didn’t work because I didn’t execute well.”
Timing, unfortunately, is out of your control. We were incredibly lucky with The Brilliance. It started within the same six months that Hypebeast and Highsnobiety did, so we got to be friends with those guys, which is insane. I was around a bunch of interesting people.
I often wonder what Boxed Water would’ve looked like if it had started even just five or six years after 2009. That was really early in terms of design and where the consumer’s mind was.
Speaking of Boxed Water- I think it’s hard for designers to have the capacity or even understand how to do something at scale. I mean, Boxed Water is everywhere. What led you to do something at that scale?
Full disclaimer, I’m no longer involved in the company.
But when we started, it was right at the cusp of people starting to truly discuss the impacts of gas-guzzling SUVs and bottled water, etc. And I thought, “Well, I’m not going to tackle the SUV problem,” laughs.
I thought small companies are where innovation comes from. And Boxed Water had the ability to zig and zag through everything and create this new product.
I didn’t really think about the market we were playing in, I thought about the problem we were solving. The beauty of starting a company when you’re young is: sometimes not knowing what you’re doing is more helpful than being deeply researched.
To that point- do you think solving the problem is where you should always start, or should you work with the end result in mind?
You said something earlier about designers not knowing how to think about things at scale.
If you want to solve really big problems, then scale is going to be a part of the conversation from the beginning. If you want to express yourself and just experience the joy that is design, then it may stay small.
Blending those two, I think it’s really challenging, but in a fun way.
Do you ever struggle with the idea of “Who gave me permission to do this?” And how do you move through it?
One thing I really want to get into is property development. The scale of that is big. People who are in that world either went to school for it, have connections, or worked in the field.
It’s not something like, “I’m going to start a t-shirt company or a brand or something.” The amount of moving pieces can feel very overwhelming.
I do have a few mentors, which helps. But I’m big on just trying to find a way to sneak in. Crack the door open a little bit. I think if I found an opportunity tomorrow where someone said, “Would you come intern or come get coffee for me for six months?” I would probably go do that.
That’s less about permission, more about hacking and sneaking in, if that makes sense.
It does make sense. How important are mentors? Or how important have they been to you?
One of the most important things in my life in retrospect. You don’t know someone is your mentor until years later, until every thing is kind of rolling.
My mentor has been involved in every major decision of my life. A voice of reason when I’m kind of lost in my own weeds.
I think finding a mentor is tricky. But mentorship is super important. How you find one is often by asking someone you really admire, or someone in an industry you want to get involved in, if you can help them in any way.
You’re going to bounce off the walls a few times, but you’ll find that person that gets what you’re after. Just give it a long time. It takes time.
Switching gears, AI tools like Sora are collapsing the time and skill barrier between idea and execution. As someone who has always operated in that intersection of idea, object, and image, how do you see this changing the role of the designer? Do you feel urgency to adopt or resist this?
laughs I’m trying to resist the desire to resist. I think that’s the path to getting old, mentally.
I remember when the internet became really popular and people were like, “I’m not going to participate in that.” And I think they got left behind. I look at AI the exact same way -it feels just as big.
That said, I’m in love with physical product and analog things. I’m at odds sometimes. For example, with the Knock Wallet. We probably could have run a zillion different models on this thing and maybe come up with something better, or at least more interesting, than what we already have.
I love just designing from zero with only your mind, your friends, and your frustration.
That said, I always joke, I use generative fill on Photoshop every day to fix margins and other things like that. Use whatever tools are available to you.
There are maybe five super talented employees that work for one really talented industrial designer -but the credit always kind of goes to the person that’s above them.
What’s different from some really young person that doesn’t have access to five people under them using AI to achieve the same effects? I actually think that’s really elegant and encouraging for the human species. It flattens things again - even more.
How important has your team been to you?
I don’t have a big team with the current project. But I have two people who mean the world to how this thing has rolled out in the past few years.
One is Chris Bane - he’s here in Chicago. A photographer. He is so intense and I now don’t see the project as being finished until his photos are done in editing. You spend all of this time building this thing, and the most important part is how you communicate it to the world. His photos have become really important to me. A great collaborator and a great friend.
And then Rotenda, who reached out to me to mentor him - which now, I think it’s the other way around. He’s an automotive designer, based in Munich. Incredible person and incredible friend. A really technical industrial designer, but also has a super creative, emotional brain.
I’m not sure the company would still be around in its current form without those guys.
You mentioned Rotenda working in automotive. How important is it to digest other mediums as you're building?
Paramount. Take in inputs from a zillion different things.
I reference Steve Jobs too much, but I think it was during the early development of the Macintosh - he prided himself on hiring people with really diverse hobbies. If you want to look at it competitively it’s going to give you it’s going to give you edge. If you want to look at it emotionally, why not live a really full life? and they can be hobbies they don’t need to be businesses. I’ve gotten into baking recently and it’s very humbling, it’s so different than anything I’m working on now but it’s informing how I think about the human-ness of products and it’s just fun.
How important is speed in getting your ideas out?
It’s kind of my obsession. I’m probably too into it, honestly. Maybe it’s because I came up through the internet—first as a programmer before anything else. In programming, you can just stay up late and finish it. You can brute-force your way to the end. But with physical products and industrial design, you have shipping delays, manufacturing issues, lead times.
And I hate that. I always want to push those obstacles to the side.
I’m sure there’s a self-gratification element to it. But the real reason I’m obsessed with speed is I’m obsessed with testing things. I want to get the idea out in front of strangers as soon as possible so they can tell me if it sucks or not.
The final, most important moment is when a stranger sees the thing and says, “I’ll buy it” or “I won’t.” That’s terrifying—but it’s also what I love.
So many people romanticize the idea of running a ‘sexy’ business - art, fashion, etc. What would you say to them?
The older I get, the more I see friends go and get jobs. There was always this idea that we were only going to do the work we wanted to do. But life’s realities come into play. And that sexy thing? It can start to feel a lot less sexy.
I don’t know how scalable The Object Company will be. We’re starting to think about what it would look like to grow. We have people poking around, asking about investing, and that would change things—fundamentally. It would become less sexy, for sure. laughs
I think especially when you’re young, you should pursue everything that interests you. But don’t do it to your financial, emotional, or mental detriment.
And we need to celebrate the unsexy industries, too. Virgil used to say we need more chemists. laughs Not everyone has to make hoodies or get into fashion.
It would be way more interesting, in some ways, to creative direct city planning. Or figure out how to make Citi Bikes cooler. We need more people with outside thinking entering so-called boring fields.
What’s your view on selling out? Do you think taking the check is okay sometimes?
I think it all comes down to your intention.
You asked earlier about how important a team is. If you want to hire great people, you have to pay them well. You have to take care of them. So when you need funding, the nice thing about brand collaborations is—they’re not investors. You still control your IP. You still get to make the decisions.
It’s a beautiful thing when the people you hire start getting mortgages, or their salaries go up. Life is about more than just the objects we design.
If you take the check and it looks like you didn’t put your heart into the work, people will know. That’s when it starts to hurt your brand.
But I look at what Sam Ross did with Zara, and those clothes were stunning—100% Sam. I had a hard time telling the difference from his own label. He put real heart into it. It made his work more accessible, and more people could participate.
If you stay true to yourself during the process, I’m all for it. But if you don’t—it can do real, long-term damage.