Tucked away in suburban Pennsylvania, Jeff Sheldon is at such a crossroad. Sheldon runs the popular apparel store Ugmonk with help from his family. He keeps the business lean but firmly within his control. The online-only store sells t-shirts, bags, and other wearables with high quality materials all hand-designed by Sheldon. Now in his sixth year, Ugmonk moves thousands of items a month, and has won the praises of design-minded customers all over the world.

But with the business growing slowly, he's now faced with a hard choice. Should he abandon the designer's dream of having complete product control in order to grow his company? We chatted with Sheldon about what happens when your side project turns into a full-time business.

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You live in suburban Pennsylvania. Why have you chosen to live there as opposed in an urban center, where designers typically flock to?

I attribute some of my success to that fact. I have so much time, focus, and space to work on things, that I’m not distracted by all the concerts, the meet-ups, and stuff like that. I’m able to put in quality work because I’m in the middle of nowhere.

What was it like in the early days of Ugmonk?

I had zero idea on how most of this stuff worked. I had never printed a shirt. I knew what a screen print was. I studied designing palettes, I knew design, I had a set of designs for print. But I’d never sourced t-shirts. I’d never put up a website.

I actually get e-mails every single week from people starting out, asking for advice. But the answer is that we just spent a ton of time learning those things. The things that challenge us are what make it fun. Learning each aspect of the business has been a continuing process, and I still tell people that I have no clue what I’m doing half the time. We’re all faking it until we make it, really. 

And I think the difference between what maybe people see from the outside, and what I’m actually doing, is that they didn’t see me spending my Friday night sitting there on Google, trying to figure out how to get the shopping cart to a specific thing on our website or how to figure out the next source of the next product. It’s literally just hard work and it’s not rocket science. It’s more about just putting in the time.

I think I’ve been asked the question “Where do you get your inspiration?” a hundred times and I still don’t have an answer for it. I don’t even know. But everyone’s looking for that key, that secret sauce.

Jeff Sheldon at work in the Ugmonk offices.

Who is the typical Ugmonk customer?

When I started, I thought it was going to be other designers and design nerds. But it quickly grew beyond that, to the point where it’s anybody who just appreciates the simplicity and minimalism. Anybody from a middle-aged suburban mom to a hipster in New York.  

I think my core demographic is still the people that are the taste makers, the people that are into the music before it gets big, and the art before it gets discovered. People that curate their experience in life better than any average person who just goes into a box store and grabs a few graphic tees. They care about the quality, and they care about the ethics that are behind the company.

What are the “ethics” of Ugmonk?

I started the business around creating products that I wanted and that is a filter for everything that I do. I’m not going to put out anything that I don’t personally like or wouldn’t personally use. Which means sometimes not hopping onto the trend that I could probably cash in on. 

As for the ethics, right now we’re doing almost everything made in the U.S. People that we work with are paying their employees’ fair wages, and the products are made environmentally friendly or just done the right way without cutting corners for cost. Our top line isn’t profit, it’s quality. So, maybe it’s a little bit pricier but we are going to put out a better product.

Do you personally design every single item?

I still design every single thing and that’s the part that I love the most, and that’s kind of why I started Ugmonk. I just love to design. As the company grows, we wonder if we’re going to hire employees—I think about this a lot. I know that my particular strength and area of interest is to stay on product as long as the company is around.

A model showcases the Ampersand Crewneck

It sounds like the common thread in all this is you, right? 

Right. The only thread that ties that together is that it’s all coming from me. A lot of the things aren’t related or don’t have necessarily a structure or reasons other than that. It’s my conscience, or my beliefs and how I want to run the business.

But you don’t scale.  So how do you grow the business? 

I’m okay being smaller and sustaining the company, we’re still growing every year. We’re not growing a hockey-stick growth, but we’re growing enough. We’re building that fan base and in it for the long haul, so I’m able to keep it really small and handle every part of the business or almost every part of the business, which does limit me on the creative side sometimes. I can’t release a hundred products every year. I can’t speak at dozens of conferences. I have to limit everything I do.  I don’t have a wholesale team and I don’t have the sales team to go out and sell. 

But I’m okay with all those things right now. I choose to keep it small, to keep it lean, to keep this business profitable where it is. We don’t have any investment.  Now our ”small” might grow in the next couple of years. But we’re not really focused on trying to build out a team of 50 employees to take this thing global.

The full "design studio" at Ugmonk HQ, where Sheldon designs every product.

It sounds like everything is very catered to having this thing last a long time. Is that your intention?

I don’t have any intention of doing something else or selling the company. It’s all about the customers I have. Most people come back and buy again. We have people buying multiple items or people buying almost every single release as soon as we put it out.  So that “1000 true fans” mentality is important. I’m much more focused on building that tribe of core followers that care about what I do, then having ten thousand, one hundred thousand, or one million people that kind of like the cool shirt today, and then they totally forget about it tomorrow. 

Especially in the clothing/fashion/design world, things are very ephemeral. It sounds like that slow, more methodical approach is your goal here.

I’m still selling the same shirts that I sold six years ago, which to a fashion brand, they’d be like, “You’re crazy. We don’t carry anything more than three to six months and then we get it out the door and bring in the next season.” But I’m kind of like the complete opposite. I’ll make a bag I want to last a very long time and I want to see it relevant now and I want to see it relevant five years from now. 

How do you maintain the discipline to not chase trends? 

I don’t know if I’m even the best at balancing it. It’s just me making choices. I ask myself  “Is this going be beneficial to go to this event? Or a trade show? Or a conference? Or would I rather just stay in my home office, cranking away on and working on a new product?”

Just the assurance that what I’ve done has worked is enough. It’s not like I need a complete revamp or to change the model and say, “I’ve got to get on trend, people aren’t buying it.” So I feel more confident in the style and in the mentality of what I’m doing every year, just seeing that it’s still working.

It’s easy to stand by your principles when it’s working. But what happens when things go wrong? 

T-shirts, bags, journals, and all the stuff that we’re doing is not necessarily reinventing a wheel, it’s just putting my touch and style on it. I think it makes it a lot easier than coming up with a completely new thing. A lot of these tech companies, they’re launching an app and then saying, “Oh, I didn’t realize no one was going use this.” It’s a little bit easier in the market and niche that we’re working.

Sheldon in his office surrounded by his prints and inspiration.

Running a business isn't mostly about the design side, but the administrative side.  So, how do you navigate that and make sure you balance it out?

Again, that’s a constant battle to create with the creative space, or to block out the time to work on new products. I’m not the best organizationally or schedule-wise, so there’s times where, since I don’t have a project manager breathing down my neck and meeting deadlines and stuff, that stuff ends up getting pushed out either a month later or even years later, and the balance between those two things is really tough. And I think that’s why, looking at some of my weaknesses and thinking about some of the things we want to grow... It makes me consider hiring somebody to alleviate some of the business side of things so I can have that space, so I can really focus on product, because that’s what really pulls the brand together. 

But sometimes I get 100 percent obsessed on something that’s not the first priority and then I end up kind of finding myself saying, “Oh, I actually need to take care of this boring stuff and then I can work on that creative thing again.”

Sounds like you have to balance the slow, unfocused, but fun version with the possibility of growing the company faster with more structure. Have you decided which one of those is more important?

If we’re going to support someone else’s salary, even a part timer or a couple of people, that changes the dynamic. I can’t be off editing photos that don’t need to be done right now, or working on a new product that’s a couple of years out. It is a little bit nerve wracking. I don’t want to lose the love of the business I have right now. Or the idea that I can wake up and literally do whatever I want— there’s a beauty to that freedom.

See the rest of Ugmonk's wares here.