Running a Successful US-Based Product Business with Jeff Sheldon and Ugmonk

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Jeff and I talk about picking names, following your passion, and his great attention to detail in this episode of How I Built It. In a usually saturated market, Jeff has build a great business on t-shirts and other clothing. His insight is fantastic!

Show Notes



Joe Casabona: Hey, everybody. Welcome to another episode of How I Built it. Today’s episode is sponsored by two great companies. The first is Sucuri. Sucuri is a website security done right. They will protect, detect and respond quickly. That means you’re always protected from hackers and other breaches. They offer everything from website scanning to SSL setup, and mitigation of attacks like denial of service. If you want peace of mind for your website, head over to today. That’s, today. 

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And now on with the show.

Hey everybody. Welcome to another episode of How I Built It, the podcast that asks, “How did you build that?” Today, my guest is Jeff Sheldon of Ugmonk. Jeff, thanks for joining me today.

Jeff Sheldon: Yeah. Thanks for having me on.

Joe Casabona: Awesome. So I’ve been a big fan of your work for a while. I think I came on around your fourth-anniversary edition stuff. I’ve got your ampersand logo in various places around my apartment. So I’m really excited to talk to you about this. And I want to start with just like a simple introduction about you and Ugmonk, and how you came up with this idea? So, can you tell us, you know, kind of what made you start Ugmonk?

Jeff Sheldon: Sure. I’ll give you the short version of how I kind of got started into this crazy entrepreneurial journey of essentially selling physical products through my eCommerce store. 

So I grew up doing all sorts of art,  painting, drawing, sketching, that kind of thing. Always making things, building things out of Lego’s just fascinated with that type of creation process. And then I later studied graphic design in college and was able to apply a lot of the same principles of art and things that I love, but more in a commercial sense. 

And then got my first job and moved up to Vermont, where I was working at an agency. And fresh out of college I was excited to design and do all these creative projects like, just being fresh out of school. And my role there was not necessarily super creative. So I decided to start a little side project to keep my hands busy just because I’m not somebody that can really sit around and sit in front of the TV. I’m just too fidgety for that. So I started what is now known as Ugmonk, which was just a side, a small side project to design t-shirts that I wanted to wear and then sell them online. And it’s obviously evolved quite a bit from that, but that wasn’t the origin of, or how I got my start.

And a little bit of backstory, how I got into t-shirts was that I was doing some contests for sites like Threadless, and designed by humans where you essentially get to design a shirt, submit it, and then people vote on it, and then they pick the top ones to print. And, that’s how I got my entry into the whole apparel and t-shirt world. But the design was always at the forefront of everything that I wanted to do. Like the design process was what I loved.

Joe Casabona: Nice. That’s awesome. And,  you know, I know that a lot of people like to try to kind of making t-shirts. I’ve done it a bunch of times, but I tell them that you really do well. So it’s really cool that you’re able to apply your graphic design skills to do. And not only t-shirts now, but, you’re like metal and percent desk things. And I have that and I think it’s absolutely beautiful. So you make a lot of really cool stuff and I’m really excited to kind of dig deeper into that.

What kind of research did you do before starting this? If any, was it like a, ’cause, you know, there’s like, there are tons of t-shirts sites out there, you know? So did you do research to see how you could kind of differentiate yourself or was these cuts kind of like a whim thing? 

Jeff Sheldon:  I was definitely doing some research on the t-shirt side of things and pretty involved. Now, this was back in 2008. So before social media, it was all about forums. So I’d spend time in these different forums learning about t-shirts, and printing techniques, and design techniques, and just what works well on a t-shirt. But just myself, you know, self-learned. When it comes to that side of things, I don’t have a fashion background or knew, I didn’t know too much about any of it, which is kind of the moral of my whole story is that I am making it up as I go and just learning along the way. And as I started getting into researching t-shirts, as soon as I wanted to branch into other products, I just followed that same path, just, you know, a lot of Googling, a lot of talking to people, figuring out the different things of how do I make a physical product. And then how do I sell it, and how do I market it? How do I, you know, use e-commerce, use the e-commerce tools that are out there, and customize. So just little steps along the way to figure everything out until it is where it is today. Eight years later, and we have, you know, we shipped thousands of products all over the world.

Joe Casabona: Nice. So when you’re building these products, do you get like material samples or things like that? And how do you figure out like what brand to use and like what works? You know, like you have a wax canvas bag like I’m really curious as to what went into creating that. 

Jeff Sheldon: Yeah. I mean, the sampling process is definitely a part of it. I actually made one of my earliest mistakes getting my first run of shirts without getting samples. And they actually turned out really poor quality and had to…it was a whole long saga of trying to get those fixed. But now, I get samples of everything. Material samples, print samples. I have my printers or my manufacturers send over photos and kind of work back and forth either just through video chat or through mailing physical samples, back and forth to kind of,  iterate on each prototype of something like the bag.  and really because they’re physical products. I have to be able to touch and feel them like it’s one thing to show somebody a digital prototype or show someone a photo. But If I can’t feel the fabric or see how it reacts or see how it, you know, feels in my hand, it’d be kind of impossible to build physical products just virtually. So that’s a big part of, you know, having this stuff coming in and having all sorts of prototypes, and fabric swatches, and blank T-shirts that I’ve gotten over the years just to really try and decipher what direction I want to go. And find the things that are best, the best quality out there.

Joe Casabona: Gotcha. And so what do you think is the best quality t-shirt? I guess I could like to check one of the t-shirts I have. But what do you think is the best out there?

Jeff Sheldon: Yeah. I mean, I guess best is a little subjective. But, we’re using right now, we’re using a couple of different fabric blends. Tri-blend 50/50 and a hundred percent cotton. But these aren’t just the same. There’s so many grades and varying levels in each of those. You can get a t-shirt for 99 cents from overseas, but the shirts that we’re using are mostly made in the US and are of much higher quality. And even the cotton, and the dyes, and everything, all the way down to the printing techniques, and the type of inks that we use. There’s such a range in quality. So we definitely are not set up for a wholesale model because we have, you know, our costs are so high. But that’s in order to produce the best product that we can. 

Joe Casabona: Gotcha. Cool. Very cool. And on top of the research to kind of find the products that you want to put out there, getting the samples and things like that, I’ve recently found that talking to people helps a lot. You know, I kind of revamped a business over this summer and that came after tons of conversations with people in the space that are kind of in the adjacent space to what I wanted to be in. Do you talk to anybody? Are you part of a mastermind group? Or get business advice from anybody?

Jeff Sheldon: Sure. I’ve been in various kinds of mastermind groups or mostly. But what I find most beneficial, it’s just reaching out to individuals who either have been, again, like you said, in this space, or might have a contact or know someone else that could connect us. And, those conversations are just jumping on Skype or jumping on the phone. You know, the more people you talk to, the more you’re able to learn from. And there’s a difference between learning from somebody and then just trying to leech all the information and not do any of your homework. So I try to always go into those calls or those opportunities showing them like, “Look, I’ve figured out these are the three types of manufacturing processes” or some sort of knowledge so they know that I’m not just coming, asking for free information. So I think there’s, yeah, for people starting out, it’s great to talk to people and it’s great to ask questions. But it’s also great to do your own research and do as much as you can on your own to show that you’re working hard at it as well.

Joe Casabona: That’s a really great piece of advice, right? It would be one thing for me to reach out to somebody and be like, “Hey, I want to start an online course. What should I do?” But it’s another thing to say, “These are the things I’m thinking about trying, and these are what I’ve seen worked other places. What do you recommend?” Because it’s right. It shows that you’re bringing something to the table. That’s a really great piece of advice.

So why don’t we get onto the title question here, right? And this question in previous episodes has been geared to people who have, who’ve built things on the web, right? And I know you have a website and a shop, and I’d love to hear how that’s powered. But I’ll be honest with you. I can’t really make anything with my hands. I’m very lucky computers exist because, without them, I don’t know what I’d be doing. So, I’d be really curious to learn kind of, you know, maybe you could cherry-pick a couple of projects, of products and talk about the process for creating those.

Jeff Sheldon:  Yeah. I can start with just t-shirts, which are kind of the most basic process, the creation process for what I do. And, it all starts for me either with a sketch, a hand-drawn sketch. So that’s, you know, just getting on my pencils and sketchbook or a sketch and illustrator where I’m, maybe experimenting or playing around with different shapes or fonts. And then I go through sometimes hundreds of iterations to get to a place where I feel like the design is finally polished. And I’ve shared some of this stuff on my blog too, to show you kind of like, here’s how the design started. Here’s how it evolved. And then sometimes the end result looks nothing like the original sketch.

But you can see the layers of depth that I’m kind of working through and processing the same way that you would,  you know, wireframe a website and work through multiple prototypes and iterations of that to get it to the final site. Like it may not look like this, this thumbnail sketch at the end, but there’s, I try to really be obsessive over all the details. So if I’m doing a, let’s just say I’m doing something that’s got a hand-drawn type based on it, I’ll sketch those out on paper and then often I’ll scan those in, bring it into illustrator, and then turn them into a vector file just by manually clicking and dragging path points,  which is a tedious process. Again, this isn’t like a, I just stick it in there, hit the filter, and then all of a sudden I have it ready.

And then, yeah. Just a lot of time getting those paths the way I want them. And then I go through a different mock-up process where I’ll figure out what colors work for the design, going through mocking them up on different t-shirts and different colors just in illustrator. Because certain designs work better in certain colors and certain designs work great on t-shirts, but they don’t work great as posters or vice versa. So it’s really helpful to keep that in mind like I’m designing. So I’m not just looking at it on a piece of paper if it’s supposed to be the final design is going to be on a shirt.

And then once I have that kind of finalized and I’ve picked the approximate colors, I’ll break out my Pantone book, which is essentially just a book of color swatches. That is the universal standard for all colors in the printing industry. And because when you’re looking at something on a screen, you’re looking at something to print. It can look very different, but it can be technically the same color. So the Pantone book allows me to pick the exact colors that I want. So if it’s a very specific light green, I can specify that in the artwork when it, before I send it to the screen-printer. And then, yeah. It’s just a matter of talking to my screen printer and sending them over all the notes about the artwork, and working through a sample or two, and then getting the final run printed. And hopefully, all along the way, everything goes smoothly. But oftentimes we have to tweak things or change things, or, it’s not maybe as easy as a process as that sounds, but that’s the kind of in a nutshell.

Joe Casabona: Wow. I mean, that’s, you know, it seems like there’s probably A lot of upfront costs when you create a product like this, is that right?

Jeff Sheldon: Yeah. We don’t do a presale model. We order everything. like I’m buying the physical inventory before I release a product. not that there’s a right or wrong way to do that, but I like having a physical, finished shirt that I can photograph, put on my website so when people receive that they know exactly what they’re getting, it doesn’t look different from a digital mock-up. and also they don’t have to keep people waiting. So there’s like if they buy it on Tuesday, you know, we’re shipping it on Wednesday or Thursday, and it’s getting right to them. So I like the immediacy of having that product and not worrying about it. Maybe evolving into something else from the original thing that I showed customers to the thing that they received in the mail.

Joe Casabona: Yeah. Absolutely. And so, and your photography, the photography on your website is beautiful. You know, I know you do like a lookbook too and, are those pictures that you take or do you hire somebody to take those?

Jeff Sheldon: Yes. So I do all of the product photography, all the stuff that you’ll see on the shop side. And then any of the lifestyle lookbooks stuff, I actually worked with a friend who’s a photographer who does some of the coordinates, all the lookbooks session with the models. And it really brings a little bit of personality of what the brand is and kind of allows customers to say, like, “I can see myself wearing that. Or, I can see myself using that wallet” through the lifestyle stuff. But, I do spend a ton of time on the product side, on the product photography. Something again, that I’ve just been self-taught, but over the years have been able to kind of tweak my setup and make the products as crisp and as clear as I can since that’s the only time that customers get to interact with the product before they buy it.

Joe Casabona: Yeah. And I especially like your closeup shots, you know, it really shows how kind of like the ink meets the shirt and things like that. Like, I really liked that. It makes it feel like I’m looking at it in real life almost.

Jeff Sheldon: Again, something that you can’t do with a mock-up like, you can fake that in Photoshop. But because I have the printed shirt to photograph, I’m able to kind of show of all those special details like that. Otherwise, it would be hard to kind of replicate through just showing in Photoshop.

Joe Casabona: Yeah, absolutely. So aside from t-shirts, one of your most recent products was coffee, right? Like a custom run of coffee beans that you put out. What was the process like for that kind of coming up with your own brand of coffee? And it was a limited edition,  right?

Jeff Sheldon: Yeah. It was a fun project. And I’ve done a few of these different collaborations that are just kind of a one-off fun project. And this wasn’t to say, like, I’m going to pivot my business and we’re not going to sell clothing. We’re going to sell coffee from now on. It was more of a, there’s a local roaster called square one that I’m a big fan of and have been a fan of for years. And then they actually approached me when they saw me do another collaboration with another company last year. And they were like, “Hey, if you ever want to do like a custom on a coffee, let’s talk.” And it was a great partnership because they came with the specialty of being amazing roasters. They’ve won national awards for their coffee. They know exactly what they’re doing when it comes to coffee. And I, as a consumer, I love the coffee. I enjoyed the coffee and I thought it’d be a fun thing to do to put my spin on the packaging, be able to design that. The whole presentation, the story, and then just pull those two things together. Really just as a fun project, not to try and make a ton of money or try. And again, like changing the business or the direction of where we’re going. But, it was a lot of fun to do and I’m really happy with the product. We are completely sold out so I can’t pitch that on the show here. But there’s a little project like that that may not make a lot of sense from a business number and revenue generation standpoint. But for me, it’s fun because I get to bring my expertise. They got to bring their expertise, and then we teamed up and made a really cool limited edition coffee. 

Joe Casabona: Cool. Very cool. And the coffee is sold out. But, you do have like the companion, like Cemex leather grip, is that right?

Jeff Sheldon: Yeah. So we released these leather Cemex colors. And for anyone that doesn’t know what a Chemex is, it’s just a simple glass, coffee poured over a brewer. That’s been around for, I think, almost 50 years. But we made these cool little leather wraps with the ampers, the Ugmonk ampersand, and embossed on the side just as a way to customize your coffee set up. And we do still have those on the site and a lot of people are really loving those.

Joe Casabona: Nice. That’s awesome. So you started off as t-shirts, you do these smaller partnerships to put out things like coffee and other things. So we’ve talked a little bit about this. But, what are some of the milestone transformations in your eyes as far as where Ugmonk was and where it is today?

Jeff Sheldon:  Yeah. I think if you look at where I started and where we are today like one of the cool things is that my mission is still pretty much the same as it was from day one. It was to create products that I wanted to exist that for the first iteration of that was t-shirts or the first medium was, it was t-shirts when I’ve since branched out onto, into leather goods and collaborations like the coffee and prints, and all sorts of other apparel. 

But the transformation I feel like has really been a slow evolution to grow and kind of mature as a brand. I’ve matured as a designer. I’m still learning, still growing. But you can kind of see like the trajectory from eight years of doing this, how much more refined everything feels. So I don’t think it’s necessarily a if you look at year three and you look at year four, all of a sudden we are a different brand. But it was a very slow kind of evolving progression. And I think people enjoy following that journey and progression. And I’ve had people following the brand for years. Like you said, you’ve been following for at least four years now. And I’m not trying to reinvent the wheel and I’m not trying to do anything like crazy innovative. But at the same time, I’m just trying to keep pushing the brand to the next level.

Joe Casabona: Yeah. Oh, absolutely. And, I’ve said this a couple of times, but it shows in the quality of your work, you know, it’s you, especially for these, you know, these smaller shops, it’s really important to kind of build that brand loyalty and then continue. You know, continue kind of bringing that to the table. And you’ve really excelled at that, you know, your anniversary additions. I haven’t been able to buy them the last two years because I got married and now, my wife is expecting. But I hope to be someplace soon where I can definitely like put the money towards that stuff because it’s really great. This collectible stuff, and it looks fantastic.

Jeff Sheldon: Yeah. And I think even from the website side of things and the branding, we just, you know, I just redesigned our whole brand a few months back. And I think even looking at that, like the iterations of the website or the iterations of the logo and how things have changed is this really fun. And sometimes I forget, like how far we’ve come from the original Wood Grain background website that I had thrown up in 2008. But yeah. It’s a lot of fun to continue working on the same thing for like such a long period of time. 

Joe Casabona: So it sounds like you want to continue working on this. And so I want to ask what are your plans for the future of Ugmonk? What can people look forward to?

Jeff Sheldon: The first thing would be just more products. I’ve got a list. I’ve listed upon lists of product ideas and things I want to make. Some, I guess, I can hint that we’re hopefully going to be launching a Kickstarter for a new desk product, office product that I’ve been working on for several years now, early next year, and I’m really excited about that. And to finally, hopefully, get that into people’s hands. But really, I just want to keep sharing and growing the brand the same way that I’ve been doing. I’ve been posting a lot more journal content which is essentially just the blog where I’m showing behind the scenes, sharing the tools they use, sharing pretty much just everything to help other people follow in my footsteps, or help them just to be inspired to do their own thing.

Joe Casabona: Very cool. Very cool. Well, I lost my train of thought here for a second. You mentioned Kickstarter and sharing more and things like that. Oh, you have a long list of products. So you have a long list of products, how do you decide which one you want to do next? Because that’s definitely something that I struggle with. I’ve got 19 app ideas or plugin ideas I want to write and I can never choose.

Jeff Sheldon: Yeah, I think that’s the struggle that any entrepreneur or creative person faces. Because there’s like, there are more opportunities than there is time. And making the decision of what I’m going to spend my time on is something I struggle with all the time. I actually just tweeted yesterday. There’s things that I should be working on, things that I want to be working on when I, and I usually default to working on the things that I want to be working on. 

So for me, like I know there’s certain things that is our bread and butter, designing T-shirts, selling t-shirts. Every survey we put out, people want more shirts, more colors. I can’t ignore that request. Even though I’ve been doing this for eight years, I’ve been releasing shirts for eight years. So making sure that I’m not ignoring those key things.

And then making sure I’m also making time for the things that I want to be working on like these other product ideas. But just trying to find that focus in that balance I think it’s like a constant struggle. It’s really just like, I don’t even know how to explain it, but like when you can’t stop thinking about a certain idea, and that one idea keeps coming to the surface. Usually, that’s the thing you should be working on on the side or in addition to the, you know, the bread and butter.

Joe Casabona: Gotcha. That’s pretty great. That’s great advice. if you, if it keeps coming up, it’s definitely worth exploring. You know, cause you know, you can have these kinds of fleeting ideas like, “Oh, that would be cool.” But if you never think about it again, it might not be worth investing in.

Jeff Sheldon: Yeah. And like, what’s the goal of those projects? Sometimes it’s like, “Oh, I could build this app or I could do this thing.” But just because you can doesn’t mean like, you know, if you’re not passionate about it, you’re not interested, or are you just seeing it as a way to maybe to like, make some quick money because some things, you know, current and hot right now that you think you could cash in on, like, that’s going to die off pretty quickly. But if it’s that idea, that’s like every time you pull out your phone and you’re like, “I wish this app existed. I keep trying to do this and no one’s making it.” I feel like that’s gotten much more weight to it, to spend time developing and figuring out cause it’s something that you’re going to be excited about for a while.

Joe Casabona: Yeah, absolutely. And it’s something that you use. You know, you started out Ugmonk because you wanted t-shirts that other people weren’t making. And so you’ve built a business out of that because it brings passion. And even on days where you’re getting trouble motivated, you’re still working on something you’re really passionate about, which is, yeah. Very cool.

So I want to ask the last question. So I have a two-part last question. So we’ll just get this one out of the way. Cause I think you hint on your website that this is a secret you keep close to your chest, but how did you come up with the name Ugmonk?

Jeff Sheldon: Yeah. I figured you might ask. Maybe someday we’ll reveal, like the actual origin story or the meaning behind the word, the origin story we tell. And, basically, I was when I was starting back in 2008 and designing these shirts, I hadn’t really thought through it much like this is, I didn’t think about what am I going to call it? What’s the website URL? What’s the logo?: That was all almost an afterthought. And then when I was trying to go through word games to come up with creative names and I wasn’t really approaching it from like A, this is, I just want to get in and B what I’m doing for the rest of my life. Or, for the next eight years, it was just a…I need to call the side project something. And all the words that we came up with were just felt, so it felt like we were trying too hard and weren’t really original or unique. So we were joking around and throughout different words that we had made up that were just like inside jokes and Googling them, just really just on a whim. And we Googled the word Ugmonk, and there was like no results or one result in another language.  And then the URL was open. It’s short, it’s five or six letters. And we grabbed it and just went with it. It was like, literally, that was all the thought that went into it. But now if you Google the word Ugmonk, there’s like 50,000 or 60,000 results on Google that all come back to our site because we’re the only one. So it was kind of a fun branding, a happy accident. And it’s become, you know, it’s memorable and weird enough that we got to define, like what Ugmonk is.

Joe Casabona: Cool. That’s awesome. And on that note, what trade secrets do you have? Do you have any trade secrets for us? Something that kind of keeps you on track? And this could be, you know, something that you apply to business or life or whatever?

Jeff Sheldon: I don’t know if I have any trade secrets cause I feel like most of the trade secrets are like you read these 15 things lists to, you know, 15 ways to stay super productive and all of these like Clickbait lists. And then you read through them and you realize like none of it was actually a trade secret which goes back to like, I feel like the most successful people are not the ones that are just trying to find the secrets or the magic. Like there’s certainly tools and there’s ways and methods that enhance your productivity and that can aid in that. But then there’s really when it gets down to it I feel like the biggest trade secret is like, just go do the work. And even when it’s hard to do the work, even when you hit a roadblock, do the work, when you get stuck, you know, ask for help. And just keep pushing through. It’s not like a magic trick to do that. But I think that’s where a lot of people fall into as soon as their project hits a roadblock, they kind of give up or they get stressed out and they give it up. They stop working on it.

Joe Casabona: Gotcha. I think that’s great advice. It’s been a common theme throughout Season One, you know, it’s, you always see the person when they become successful. But you don’t see everything that happens up until the point before they become successful. And that hard work is often behind that.

Jeff Sheldon: So I was just gonna say that that applies to almost anything. Actors, athletes, anyone that’s been successful, the way that they’ve gotten there was years and years of practice and hard work. And then we get to see like the successful part of them. But the same goes for even a business. Like you’re gonna, you have to keep trying and trying until you finally get to the point. And then people see you may see the success on the other side.

Joe Casabona: Yeah, that’s perfect. So awesome. Well, Jeff, thank you so much for joining me today. I really appreciate it.

Jeff Sheldon: Thanks for having me on. 

Joe Casabona: And thanks to our sponsors, Sucuri and SiteGround. Definitely make sure to check them out. They are absolutely great.

And until next time, get out there and build something.

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