How to Start a Successful T-Shirt Company | eCommerceFuel

How to Start a Successful T-Shirt Company | eCommerceFuel

The Ugmonk Story: Starting More than Just a T-Shirt Company is a design-focused brand that was started seven years ago by founder and designer Jeff Sheldon. They started with four t-shirt designs and have since grown into a multi- product brand that that hasn’t strayed from its original mission: great designs made from high-quality materials. Jeff tells us about the journey behind creating his one-of-a-kind brand.

In this episode, Jeff talks to us about a design-first approach, his team and giving back.

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(With your host Andrew Youderian of and Jeff Sheldon of

Andrew: Thank you so much for tuning in today into to the show, and joining me today is Jeff Sheldon from Ugmonk is a design-focused brand, one that just started, oh, that’s seven years ago, I think it’s corresponding. Originally started as a t-shirt brand but grew from there to be much more than that.

And we talk about a lot of stuff. We talk about how he created the brand and really how it infused a lot with his very unique personality and style. We talk about if it’s possible to scale up what he’s built with a larger team and the temptation to scale something and grow for profitability while still being able to maintain that quality that made it great to begin with. We talk about Amazon. We talk about the difficulties of offering products in a lot of different verticals, all sorts of different things. Jeff’s got a lot of cool experience and has built something really truly unique over Ugmonk, and we really get into the nitty-gritty of how he did that and what it looks like for him today. So, that being said, I’m going to go ahead and jump right in to today’s discussion with Jeff from

The Story of Ugmonk

Andrew: Jeff, so I’m sure a lot of people know the brand you’ve built, Ugmonk, what it is. But for those who may not be familiar with it, can you give us a quick overview of what is Ugmonk?

Jeff: Yes, so Ugmonk is a design brand that I founded back in 2008, focused on producing physical products that I wanted to exist, and that started with t-shirts. I was designing different graphic t-shirts and have since expanded into all sorts of other clothing, accessories, leather goods, and continue to expand the line, but all that focused around the same design and minimalist esthetic.

Andrew: Now, tell me. You started what I think a lot of people do, or at least have an idea of, is if starting with a t-shirt brand, and that’s notoriously difficult to do and to build, because building any kind of brand is hard but a lot of competition in the t-shirt space. So how did you get early traction with your t-shirts and in a niche that a lot of times people really struggle with?

Building Brand Traction

Jeff: It’s one of those things that people do say off-handed like, “I’d love to start a t-shirt brand,” or “I’d love to design a shirt and sell it.” It could be, because I think it seems so easy and such a cool thing to be able to, like, sell some t-shirts to your friends, and I went into it the same way, but I was doing some t-shirt design competitions at the time, like Threadless and Design by Humans, where you’re submitting artwork; people are voting on it. If you get picked, then they print your shirts, and you get a cash prize.

And this was back in college, and that was really my first venture into t-shirt design of any sort. I was doing a lot of other graphic design, and logo design, and branding, and once I started those contests, and I won a few times, they actually took the rights to the artwork in exchange for that cash prize, so I couldn’t do anything with them.

So I thought, “Hey, instead of keep doing this contest, why don’t I start doing my own shirts where I could keep reprinting them and selling them?” And at that point, it was not at all like, “Hey, I’m going to make the next best clothing line.” It was just like, “Hey, I’m having a lot of fun designing shirts. I love doing this on my spare time. Why not start my own thing?” And that was my grand master business plan.

Andrew: That’s cool. So how did you go? When you were designing those competitions, there was a platform, it sounded like, that you would submit, and of course, the audience would come there. Once you weren’t working with a platform like that, and it was up to you to market the shirts, how did you do that? Because, again, that’s one of the really hard parts about any brand, about a t-shirt and a design brand, is you’re not getting that traction. So how did you do that once you went independent?

Jeff: It’s crazy now looking back, because when I started, there wasn’t Twitter, Facebook, and all the social media stuff that we’re so used to now hardly even existed. This was seven years ago, and it was all these forums, t-shirt blogs, and clothing blogs, and design blogs, typography, all of those types of things where we would all go to these blogs to read. We wouldn’t go to Twitter or Facebook to find articles.

And I think a lot of it was timing, because if I had to launch today from nothing, it’s a totally different landscape as far as how you get out there, because there’s thousands or tens of thousands of more people launching eCommerce-based t-shirt brands, or clothing brands, lifestyle, anything. And when I hit it, I grew as the social media boom came, and now, I’d say it’s declining as far as effectiveness.

And I was able to get in at that ground level there and then also just reaching out to people that I had met through these other t-shirt sites and telling them about what I did, and if they liked what I did, that they could write up a blog post, and we’d do some interview or giveaway. And it was really this organic slowly e-mailing people and trying to get featured here or there or people that I didn’t know would pick up Ugmonk and start writing about it. And because there were so many less people doing it, it was a lot easier to stand out, but the landscape has definitely changed.

Andrew: And this may be an unfair question for you. But if you were going to try to start Ugmonk today, given the fact that things have shifted, how would you adjust your approach?

Jeff: That’s a great question, and I think I would still go back to what I started it based around, which is designing things that I like, designing things that I want and for myself. And there is some unique angle, and for Ugmonk, that’s the design, because I’m designing every single product. That design esthetic is all unique to me as opposed to maybe trying to catch on to the next trend of like, “Hey, sunglasses are really popular right now. I think I can do sunglasses, too,” or, “Hey, hats are in,” or socks or whatever it is.

I think I would still launch with that, but I think the only change I would do, and what I’ve shifted over the last few years, is sharing my story and sharing the meaning behind the designs, the products, the process, all of that stuff, even more. Because that’s what people are drawn to and that’s what people want to know, is not just, “Hey, there’s a cool t-shirt.” They want to know what does the design mean, where did it come from, how did you do it, and sharing more of that, and that’s where I’m pushing towards now, which I think is my unique approach to the brand that I run.

From Process to Production

Andrew: You did an incredible write-up with your waxed canvas messenger bag. We’ll link up to it in the show notes here. Not only is the product beautiful, but man, I don’t think I’ve ever seen a more beautifully done write-up in terms of the post. Really cool, and if you’re thinking about doing any kind of design work in the apparel or the fashion space, it’s well worth a read. I believe you spent over two years from inception, thinking through it, the early, early sketches through all the way until when you actually had a wax, the final part that you could sell to your customers. So so much goes into that one product.

And at Ugmonk, you have a lot of things that you offer. You, of course, have the bag. You started with t-shirts. You’ve got journals. There’s a spectrum of products. Thinking through that process, are you more inclined now to focus on a few key products, even though they take so much longer to produce but that you really can invest in and make something that, like you talked about, you really would want to own? Or are you leaning more towards still staying a little bit more maybe diversified, still doing things, of course, that you have your stamp on but maybe aren’t quite involved in the process to produce?

Jeff: I think it’s a marriage of both. There are products like the messenger bag, that I’d never designed a bag, I don’t know how to sow. There are so many things. I didn’t know the different grades of leather, and the different hardware, and all the different pieces that went into that getting as I had the idea for it. But now, going through that process, and it was a long process, and there was a lot of months at a time where I was just waiting until we could find the missing piece, or we could source a new fabric, it was a challenge. And there’s something about that challenge, and I don’t know what it is that’s inside of me, but I see it that way that I wanted that bag to exist, even if I only had 1 or even if I could only do a round of 10, and maybe nobody bought them.

But there is something inside of me that wanted to see that through, not only as a learning process, but just from a design, taking an idea from my head and turning it into a tangible product that I could use. There’s a lot of reward that comes from that. So there’s a lot of products that are going to be more complicated. I have products in the works now that have been sitting in the back burner for almost two years or probably over two years, and I can only handle so much. I can only do so much as a single solopreneur kind of position.

But I think that the t-shirts and some of the prints and the stuff that’s not as hard from a production standpoint will continue. I’m going to continue bringing out new designs in those as well, so it’s like the long term and short term, like still keeping fresh on both fronts.

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Ugmonk by Jeff Sheldon from Ugmonk on Vimeo.

Balancing Growth and Quality

Andrew: You mentioned you’re kind of a solopreneur, and I know you’ve got your mum or your mother-in-law. She helps with fulfillment and other people that maybe help in some of the areas. But primarily, Ugmonk, what makes it so special is you being intimately involved with all the products, and the design, and the details. So looking forward, have you thought about trying to scale this out to a bigger brand with more designs even if that means maybe not being able to control so tightly the creative process, or do you love the fact that you are able to keep this brand really small and intimate, and you’re going to try to focus on staying small but really just continuing to put out quality stuff? What’s your approach going forward?

Jeff: That’s an argument that I have in my brain quite often, “Should we try and blow this out bigger?” And then I’ve had a lot of people from a marketing perspective or business perspective say, “Hey, you could easily double your business if you did X, X, and X, or if you brought in these key people.”

And then there are so many other times where I’m like, “I love the fact that I get to see every order come in.” I don’t have my hands on shipping them all now, or I don’t handle every single customer service e-mail any more, but I still have such an intimate relationship with my customers. I manage my own social media accounts. I’m taking the product photos. I’m kind of the head on all of that stuff, that I think that scaling it, I would have to let some of that go, and I’m not sure if I’m ready to do that, because it’s such a special control, and I can control the whole experience.

So basically, our team now is me and then my brother, who is my partner, who does the back-end web development and some of the business end of things, makes a lot of the behind the scenes happen. And then I run the creative, and marketing, and every other of the hats that you want to name, and then my mum does the shipping, and we bring in part-time help during busy times a year to help with that, and then my sister-in-law does customer service. So it’s a true family business, and there’s a lot to love about that, even though it can be hard, but scaling it to the next level, even though the money can be tempting, I think it would start to kind of deteriorate some of that personal touch that we have.

Jeff’s Favorite Things (Or At Least a Few of Them)

Andrew: You’ve obviously had a killer eye for design and esthetics, and I’m curious. There’s a site I can’t remember, I partially mentioned, if I can’t remember, but it lists noble people online and some of their favorite things, and I’d love to ask, from your perspective, what are a couple of things that you really, really love in terms of their design and their esthetics? One may be one from just a pure esthetics, a pure beauty perspective, and then another one from just being really well designed in terms of being practical or fun.

Jeff: I think this site you’re referring to is

Andrew: That’s right.

Jeff: And they highlight some of your favorite things and people from different industries. Some of them are more fundamental, some are more design-focused or whatever, but it was a fun project. So I would say I’m not going to list my iPhone as one, even though that’s probably my most utilized, most used thing that I own that I would feel naked without, but aside from that, let’s see, a couple of things that come to mind, one, are the speakers that I have on my desk sitting in front of me right now.

They’re the Joey Roth ceramic speakers, and I must get more questions about these speakers than anything else when somebody sees a picture of my workspace. But the design of them, they’re made out of this ceramic material with kind of a plywood base that holds them up, and we can link these up, too. It will make more sense when you see a picture of them. But from a beauty standpoint, they’re just amazing. I think from an industrial design standpoint, they’re really unique, and then the sound quality is amazing, too, so I’m listening to music, I’m listening to a podcast all day every day, so I guess they’re one of my favorite things at least on my desk here.

I’m trying to think of some of the other things that I listed as my favorite, like the Chemex coffeemaker, which is just a glass pour-over coffeemaker that’s been around for probably 50-plus years. But it’s another thing that marries form and function really well, so it brews a really great cup of coffee, but it also looks amazing just sitting out in the kitchen. You don’t feel like it’s this ugly plastic thing that you have to hide when people come over. So those are two things that are, I think, a great example of design, both from a beauty standpoint and then also a functionality standpoint that I use quite a bit.

Andrew: And you mentioned your iPhone. Maybe there’s one follow-up on that, apart from, let’s say, your web browser and your e-mail, what one or two apps do you find yourself spending a ton of time on on your iPhone?

Jeff: Instagram and Twitter. I’m always checking, probably too much, but both of them are really fun ways to create that community of people that are interested in what I’m doing. And even on Instagram, I’m sharing more than just product stuff. It’s kind of just an extension of my life, so you’re seeing pictures of where I travel to, pictures of my dog, pictures of products I’m working on, and use it as a real natural extension for me being a very visual person. Other apps, the Shopify app I’m looking at just as a dashboard to see what’s happening. Shop runs on Shopify, and then apps like Simplenote where I’m just throwing anything and everything. If I get an idea, I’m just jotting down. It’s just a text-based note taking app.

Andrew: I don’t think the curse to ever update your Shopify dashboard ever goes away. It’s this constant pull. I’ve thought about taking it off, because it’s almost like e-mail. You’d think that after a month or something, you’d get tired of checking for orders, but no, you never do.

Jeff: It’s definitely addicting, and you can get a little too caught up in it, but it’s handy to have.

Juggling Suppliers & Manufacturers

Andrew: Jeff, you’ve got, of course, a brand. You started with t-shirts, and you moved into bags. You do mouse pads, journals. You’re more than just an apparel line. You’ve got a lot of different things. How much work is it to create items across all these different verticals? A lot of times it’s difficult starting a successful apparel, or t-shirt, or fashion brand just when you have to worry about just the fabric. But when you have all these different things, is it tough trying to supply these different products and juggle what I’m guessing is probably a number of different suppliers and manufacturers, or is it not as intimidating as you might think?

Jeff: And juggle is probably the right word to use, because that’s how I feel, is like I’ve got eight balls in the air and two hands, and I’m trying to just keep all of them going. Every once in a while, one will fall, by the way, and I’ve got to pick it back up. But I guess the approach that I’ve taken is I want to design all the products from scratch essentially, or they are all Ugmonk products, so I’m not necessarily designing a t-shirt from scratch, but the design is, as opposed to reselling other brands’ products.

So that means that I have to make them, and in order to make them, there isn’t one central location where I can just say, “Hey, I want a t-shirt. I want a leather wallet. Can you guys make this stuff?” It’s all about finding a different manufacturer for each different type of product, so whether that’s a leather mouse pad or wallet, or whether it’s a t-shirt, or a crewneck, or a hat, I work with a different company to make all of those things, but I don’t do any of the manufacturing in-house. So it’s like all of the design is in-house, which is me, and then all of the actual manufacturing is with different people across the U.S. or different shops across the U.S. And to find those shops is one of the hardest things. To find shops that can make these things is really, really difficult.

Andrew: Where do you find most of the shops? Are they mostly domestic, overseas, and what channel do you use? Do you use something like Maker’s Row? Do you just go online and start Googling?

Jeff: A little of both. Maker’s Row has been great, a lot of just word of mouth and just talking to people to find out where they’re making things or if they know someone that works with a specific type of material. But it’s really just digging in and doing the legwork, making phone calls and e-mailing a lot of companies that might say, “I have no idea what you’re talking about. That’s not what we do.”

Especially as a smaller brand, when I’m looking for runs of 200, 500, 1,000, or something, they might immediately say, “That’s not even worth our time.” So it’s like all of the products are made domestically, which is another challenge but also another plus, just getting to support a lot of American-made small businesses with what I’m doing, but it also means that it’s not going to be cheap. So, again, it’s a struggle and a balance to try and figure out how I can do that for each new product or what my retail price point can be and still make enough profit to make it worth it.

Why They Don’t Sell on Amazon

Andrew: You mentioned you’re definitely not the cheap end of the spectrum. And thinking through the landscape of eCommerce, Amazon seems to be almost exactly the polar opposite of you, of course, there. You’re very small, intimate, high quality. Amazon’s enormous and the world’s most efficient distribution system. Of course, there have lots of high quality stuff there, but a very different company and almost always when you compare it to Ugmonk. So what are your thoughts on Amazon in general, and then do you shop there a lot?

Jeff: I would say we are very different, and we’ve purposefully stayed off of Amazon. We could sell all of our products through Amazon, and again, it’s a temptation where people said, “Oh, if you just got some of these things on Amazon, the audience there, you could double your revenue.” But you’re either with Amazon, or you’re not against them, but you’re on a different path than Amazon in order to stay in business, because you can’t compete on price. They’re going to keep pushing you down on price, and that’s great for the darned consumer, but as a brand, we want to create our whole experience, our website, the way we interface with customers. Not having any middlemen is part of how we can deliver such great personal touch.

And not that you can’t do that on Amazon, but it’s a very different feel, and a lot of our customers that are buying from us, they love the fact that it’s supporting me; it’s supporting my family; it’s literally putting food on the table for us and allows me to keep designing. So they like that there’s a face behind the brand. As far as me as a customer, I will still shop at Amazon, but I find myself drifting a little bit more towards, “Hey, if I can get this product directly from them on their website.”

Just as a business owner, I know how it feels to get that without the chunk of margin taken out, so trying to support people that way, too. But there’s a lot that Amazon’s done that’s great. It’s made products widely available, so I wouldn’t say I’m anti-Amazon at all, but with the Ugmonk brand, we’re going to continue to just keep it on our site and solely there.

A 24-Hour Job

Andrew: Jeff, you’ve been doing this, I think, for about seven years now, and I’m becoming more and more interested, I guess, as I get older as an entrepreneur about thinking about how entrepreneurs, their day-to-day changes over time. And some people think you bust it like crazy early on, and then you can let off the gas earlier. And I think there’s a case we made for all, so if you can keep something growing, you still have got to keep really pouring a lot of time and energy into it. So I’d love to dive in just a little bit to what your work week looks like, what it looks like in terms of hours and involvement around what you’ve built. So roughly, like how many hours a week are you spending on Ugmonk, anything from design to any aspects of running the business?

Jeff: I think, technically, I could say 24 hours, but no, I don’t…

Andrew: Twenty four hours, full day?

Jeff: Twenty four hours a day, yeah. No, I’m just being facetious, but I think I’ve never tracked my hours, and I don’t really know exactly when I’m working and when I’m not working, because it bleeds into my life so much. So many of the things that I’m doing are kind of tied in personal interest and business interest: learning photography, and how to shoot videos, and all these things. I would be doing that anyways, but I’m doing it for Ugmonk, so it doesn’t feel like work, and then there’s times where it definitely feels like work, tracking down invoices and things like that.

So I would say there are some days where I would work 12 hours a day, and there are some days that I’d work 3 hours a day or no hours a day and just take the day off, but it’s a very fluid, organic, just working, not working type of scenario, which can be healthy and can also be unhealthy when you’re trying to sleep at night, and I’ve got something rolling around in my brain to tackle for the next day. So I would say it’s way more work than a 9 to 5 for sure, but it’s also a lot of those hours I don’t think, “Oh, I’m going to work right now.”

Andrew: Way more fun than a 9 to 5. After seven years, are you slowing down at all a little bit? I think, as entrepreneurs, speaking for myself at least, it’s hard to stay motivated, and I’ve been doing it for about the same amount of time you have roughly. It’s sometimes a challenge to stay motivated on your seven or eight as it is when you’re two or three. Is that something that you’ve had to deal with at all, and if so, is there a way that you can give away for recharging and clearing your head?

Jeff: Yeah, hopefully I’m not slowing down in the sense of growing the business, but there’s definitely times of burnout, or times where I feel just creatively drained, or like, “Do I really want to design another t-shirt right now?” after seven years of doing it, and maybe not the same excitement about some of the things earlier on that were novel and new. But I wouldn’t say I’m necessarily slowing down, but I do feel like I’m refocusing, and hopefully, that refocus, even in this coming year, will be able to streamline some things, and I guess not have as many irons in the fire but on purpose.

So when you’re asking about longevity, and scale, and things like that, I want to be doing this for as long as I can, even if that means we’re not growing by leaps and bounds every single year. It just might be shifting, so we might shift into different product categories and emphasize that one year. We might release less products if we have to, but if that means that I’m less stressed and don’t have to be pedal to the metal 24/7, then it might actually be a good thing. Just more sustainable and being aware of the need to take breaks, just having those breaks and making sure they’re scheduled. Time away from work is definitely important.

Giving Back with Rice Bowls

Andrew: You do a really cool thing with an organization called Rice Bowls. Can you just talk quickly about that and how you got involved with them?

Jeff: Yes, so Rice Bowls is a nonprofit that we’ve partnered with ever since the second year, I guess, into business. And what they do is essentially provide food for kids all over the world, and the way they do that is by supplying the money to orphanages in all different countries that goes directly toward meals. The highest cost for an orphanage is usually the food, and Rice Bowls comes in and alleviates that and is able to do it in a neat way.

So we partner with them as Ugmonk, and we do a charity drive around the holidays, where each item that someone purchases equals three meals to Rice Bowls, and then they distribute that to 19 or 20 different orphanages. And we’ve been doing that for a while now, and each year we’ve upped our amount that we’ve been able to donate and rallied our customers behind it, and people are donating above and beyond just the three meals that we donate per item.

I don’t know a year to date what we’ve done, but I think it’s around 40,000 or 50,000 meals just from being consistent and doing it each year. So it’s been a really cool way to tie in the giving back, and I never thought I’d be here seven years later running a company, let alone giving away thousands of meals, and selling thousands of products, and all of this. So it was more of a personal choice that we wanted to do as opposed to a, “We are not a charity based business,” but it’s been cool to see those two things merge and be able to give back, especially in this time.

Andrew: I could be wrong, but from some pictures I saw, it looks like you actually went down to one of those orphanages and visited in person. Is that right?

Jeff: Yeah, so we got the opportunity a couple of years ago to go down to a couple of the orphanages in Nicaragua and Honduras, and we got to meet the kids and see the full circle of where this money is going. Sometimes I think when we donate, it’s hard to understand. We just know we write the check, and we hope it gets to the right people.

This was like literally we’re standing there with the kids hanging on my back, the kids that are benefiting from the Ugmonk Charity Drive, so it’s just phenomenal to see that happen, and I think it’s changed my world view and just my motivation to keep doing this. And then we’ve been able to go back several times and continue to see these kids and just the small amount that we’re able to contribute, but it’s been definitely a crazy and awesome experience.

What to Buy from Ugmonk from the Founder Himself

Andrew: So cool. Jeff, if somebody is listening to this, and they’re thinking about picking something up from Ugmonk, just in parting, what are your three favorite products? You don’t have to look at just three, but if they were going to check out three that you think are some of those top items, what would you recommend?

Jeff: The quintessential Ugmonk shirt that’s now our all-time bestseller has to be the classic mountain’s t-shirt, and it’s just a black shirt with the red and blue overlapping triangles. That one has been by far the most popular shirt, now outselling everything else, so I would say that’s the first to go to. And then if you’re at a computer, and you use a mouse, then our leather mouse pad, as crazy as it sounds, is one of our most popular items and is just a unique thing to have on your desk, and you get to watch the leather transform as your hand is using your mouse years and years later.

And then the third item, let’s see, I would say either some of the crewnecks, the long sleeve ampersand crewnecks, since it’s getting colder out, and it’s winter time. Again, those have become a bestseller, and people come back and are buying them in all three or four colors that we have now. So that would be a good place to start, but it all depends on, I guess, what you’re interested in and what you do day-to-day.

Andrew: Those mouse pads are beautiful. We actually bought a bunch of those mouse pads for speakers at our recent eCommerceFuel live event; the speaker guests there. They’re beautiful. I will link up to all of those products in the show notes. Jeff, I’ve been a fan of what you’re doing at Ugmonk for a while. It’s great to connect with you, and thanks so much for coming on and talking shop.

Jeff: It was fun. Thanks.

Andrew: Want to connect with and learn from other proven eCommerce entrepreneurs? Join us in the eCommerceFuel private community. It’s our tight-knit vetted group for store owners with at least a quarter million dollars in annual sales. You can learn more and apply for membership at Thanks so much to our podcast producer, Laura Serino, for all of her hard work in making this show possible and to you for tuning in. Thank you for listening. That will do it for this week, but looking forward to seeing you again next Friday.

What Was Mentioned

Photo: Flickr/Rasmuss Andersson

Andrew Youderian

Post by Andrew Youderian

Andrew is the founder of eCommerceFuel and has been building eCommerce businesses ever since gleefully leaving the corporate world in 2008.  Join him and 1,000+ vetted 7- and 8-figure store owners inside the eCommerceFuel Community.