Season 3 Episode 5
Jeff Sheldon, designer and founder of Ugmonk

Jeff Sheldon is the creative mind behind Ugmonk, a brand renowned for curating quality products that combine form and function. In this episode, Jeff shares about his journey of developing a meaningful community around Ugmonk, where every product decision is a collaborative effort with the people who resonate most with the brand’s philosophy.

Tune in as Jeff explains how he built a loyal and engaged community of brand fans and why scaling requires special considerations for community-driven, founder-led businesses.

Designing for yourself while incorporating customer feedback

Chris Allen: I want to welcome Jeff Sheldon back to The Entrepreneur’s Studio.

Jeff Sheldon: Yeah, thanks for having me back, round two.

Chris: Yeah. It’s good. Have you been good since the last time we sat down?

Jeff: Yeah, things have been good. Last time I was limping in, barely making it with an Achilles tear. This time I’m running in, so feeling a lot better.

Chris: Well, the cool part is we got to follow your launch shortly thereafter for one of the coolest products, and we’ll talk about that. In our last conversation, we talked about the inception of Ugmonk, the minimalist philosophy behind your business as well as how you went from this side hustle of making shirts to running a multimillion-dollar lifestyle brand.

I want to drill down a little more on your process of design, development, and distribution today, because you’re designing everything from wall clocks and pin trays to coffee mugs and desk organizers. And you’ve built this meaningful community of Ugmonk advocates. Tell me about the relationship between your product decisions and your community.

Jeff: Yeah, I think it’s been a really organic journey. We talked more about my origin story so people can go back and listen to that in the first episode, how I started, and how I got into designing T-shirts, which wasn’t because I love shirts. It was because I love design and that has slowly evolved from shirts to prints to office accessories to desk organization to really systems and ideas of how to work better, how to clarify the way you work with Analog, how to clarify your desk and make it more productive. But the thread has actually stayed pretty consistent. It’s always been about designing those things that have this Venn diagram of function and aesthetic and that little crossover in the Venn diagram of how to make something that’s beautiful and useful and equally as good. So whether it’s a T-shirt or a desk organizer, it’s always been the same thing, but it’s just evolved from the outside. The product line has changed dramatically, but that goal has always stayed the same.

Chris: I think it’s really interesting. The question I maybe came away with is, I wonder how you find customers. You have this community of people who buy your stuff. So it’s almost like you’re curating these collections and you have this person in mind. I’m like, “Who do you think of?” Is it people who are buying from you or super similar to you or are you designing for yourself and designing things you like? Or how do you just have it dialed in so well on what your customers want and how they buy?

Jeff: The selfish answer is I’m designing for myself. If I don’t like it, I won’t sell it. So some of the things you mentioned, the wall clocks, the pens, those are objects I bring in. So we’re curating those and we’re selling them. I’m not actually designing those from scratch. But the filter is, “Would I actually buy it? Do I actually personally like it?” Which keeps this very tight, curated feel because it has a very consistent theme throughout. Then the people who like it come and appreciate that curation, they like the aesthetic, they like what I like. But it’s less about focus groups and less about just asking your audience what they want and just making those top three things.

I think it’s a balance because you can get too caught up in just asking anybody what they want like, “What should my next product be?” “Design that, design this.” Then the brand will have no consistency or cohesive feel because you’re basically just trying to latch onto whatever people are telling you. “I think you should make a bigger version of that. OK, make it.” And I’m doing the opposite. I’m like, “Do I want this to exist? Is this something I personally want and feel good about selling or is it something that’s just because people are saying you should make a bigger version or a different color, you should do the desk organizer in different colors.” So I filter everything through my taste and what I want.

Chris: Yeah. OK. So does your wife use the Analog products?

Jeff: That’s a good question. She actually does. So for a while she didn’t, and she is home with our kids right now. It’s much less of a desk job to put that Analog card up in front of her. But she’s been using it and I think she’s actually found it really helpful. I think people are using it in such different ways because I use it in a certain way where every single day I start with a card and I write down the top priorities of things I need to work on. That card just sits in the card holder and stares at me all day and says, “Jeff do this, Jeff do this.” And if I don’t have that card, my day is all over the place.

But other people, they’re not at a desk. She’s running around dropping the kids off at school, doing errands, but she might make a list and work through that over the course of a week. But it still gives that satisfying feeling like, OK, when you’re home, you see the card, you pull it out of your pocket, you have some tangible version of your priorities and that’s just totally different than having them on your phone.

Chris: So true, so true. The reason I asked about your wife is because I know you have kids at the house and that you’re sharing these responsibilities and that there’s certain work you do and certain work she does and I’m like, “I wonder if there’s a crossover there.” I wonder though, where do you get customer feedback from? What medium are you using to get those suggestions and feedback?

Jeff: I think we live in a time where you can get that almost anywhere and everywhere. Sometimes for better or for worse. So if I post something on Instagram, I’m going to have people commenting on it, or if I post something on Twitter, or send out an email. So I shouldn’t say I’m only designing in a vacuum for myself. It’s not just like I’m going away and designing these things. I think there’s a balance between getting that feedback and being able to post things, being able to post progress shots of products I’m working on and then asking customers what they think. I can send an email in one click and send it to 50,000 people and they’re going to write back and say, “Hey, I didn’t like this or I like this. I think you should make this.” And I can take all of that feedback, filter it down and decide, “Yeah, there’s a lot of people who actually want this.”

I do take that feedback and we’ve made some changes on things because of some great suggestions from customers where they’re actually helping me design the product. They’re not saying, “Hey, I want this, but can you change this and this and this for me.” It’s more like they’re actually helping me build the product because that feedback loop means that every single day people can comment on anything, at any given time.

Building in public and cultivating a community

Chris: I love that about the way you do your Instagram and bring people along because it’s almost this mix between these sneak peaks you do and letting people really be bought into the things you have. It’s almost like this continuous engagement where people will go to your website and see what you already have, but then they get these sneak peaks of things that are coming and it’s almost like you’ve created a way to approach product development and curating customers or community. The way you’re going about it, they’re able to help each other, which is really, really interesting. So was that an intentional thing or did it just happen?

Jeff: Yeah, it was super organic. I was on Instagram in the early days when you could only post photos one by one and you had three different filters to choose from. It was an organic thing to just start sharing there because my life and my business are so intertwined, like “Here are things I’m working on.” It just felt natural. So building in public and a lot of the things people talk about now, like “Don’t ever build in public, you’ll give away all your secrets,” or “You should always build in public because then people can give you that feedback.” It wasn’t an intentional choice for me, it just really evolved from, “Here’s a picture of something I’m designing, what do you guys think?” “Oh, this is really cool.” Someone’s like, “Oh, I’d love that on my desk,” and then I can take that suggestion.

But I’ve never had a strategy behind social media, for better or for worse. I couldn’t even tell you what my following is or engagement metrics or anything. I think part of that is not because I’m above that, it’s just that it’s so distracting from what I’m actually doing. I’m just trying to use the tools I have to get the product, the sneak peeks, the things out there to people who like it.

But yeah, social media has been a cool way for me to drip those things out so people have seen the process before I launch the actual finished product.

Chris: Which is awesome. What do you think about the way you’ve communicated with customers? Because you have an email list that probably comes primarily from your website. Then you’ve got a following on Instagram. What is the thing that has surprised you most about this way of digitally connecting with customers?

Jeff: The real end-all is that everyone’s human and we’re just using these platforms to connect. So it shouldn’t be any less of a human connection because I’m DMing someone on Instagram than it is sitting here speaking with you. But for whatever reason, people treat it differently. If you back up and think like, “Hey, if I’m sending an email to 50,000 people right now, every single person who opens that email — minus maybe a few bots or spam addresses, is an actual human who’s opening that, who’s taking a second out of their day to take interest in what I do…” Instead of trying to scale and trying to think bigger about all that stuff, it’s always like, “OK, there’s a human at the other end who clicked the like button on this Instagram post. They’re as valuable as anyone else.” But sometimes we devalue that because we’re just looking at open rates and metrics and all those things.

So it’s one reason I haven’t outsourced my Instagram. It’s so personal to me to the point where I’ve met up with people. I’m out here in Oklahoma City. If I post on there, I guarantee someone would be like, “Yo, let’s grab coffee.” And those human connections are happening because of being on social media, and putting things out there. Same with emails. I’ve had full on conversations with people. If they write back to the email when I send out a newsletter, it’s me writing back to them. Is it scalable? No, but it’s actually a really cool way to build those relationships.

Bouncing back from production and distribution setbacks

Chris: Yeah, that’s amazing how personal you take a lot of that, your intentionality is really powerful. One of the things we talk about in marketing is customer understanding. You have to understand your customers in order to persuade them or get them interested. How would you describe your ideal customer, who is it? Where do they work? What do they do? What do they look like? How would you think about it if you were to sit and imagine your ideal customer?

Jeff: It’s tough, there is no ideal customer, is my answer. But I think the ideal customers are the people who are buying into Ugmonk and what we create because they get it. And by that I mean they understand why things cost what they do — how we’re making them in the US, solid wood versus plywood versus veneer…. They’re buying in because they want the quality, and they understand it’s an investment piece. We’re not going to ever appeal to people shopping on Amazon who are just looking and sorting by price. In fact, we’re not even on Amazon for that reason because we can’t compete. But the people who are buying it, the ideal customer has that same intentionality. They’re looking for something that’s beautiful and useful, something they’re going to have for a while, and it’s less about cost comparison and shopping.

I think a lot of what I’m doing recently with Analog and with Gather is more of a mindset too. So how can I make myself better? How can I clarify all this stuff that’s jumbling around in my head or this never-ending to-do list on my phone? They’re the people who that idea resonates with and that’s not everyone. So stay-at-home moms might not have the best use case for Analog, although I think they apply. But there are a lot of us who have so many things and notifications coming into our digital worlds and we’re like, “How do I get this stuff done?” So the person that gets it is not saying, “I should just write this down on a $1 memo pad.” They’re like, “I need a system for this. I want to invest in something which is actually making my life better in a way.” It’s the same thing with Gather.

So the ideal customer understands that. It does take some education, some more thought than just I saw a shiny object over here and I’ve spent a lot of money on it.

Chris: Well, I think the last time we had the conversation you were in R&D on I think it was Gather. Talk to us about what led up to the launch. How did you decide on the product and then just how did you get it made? How do you get it made at scale? Just walk everybody through that because that was a big moment shortly after your interview aired.

Jeff: It’s been a journey. It’s been a roller coaster. We were just talking about it before the show for a little bit. Launching or building a product can be done in probably 1,000 different ways. So the way we’re doing it is not the way I’m telling everybody to do it, but I can tell you about the path we walked down.

The backstory is that we manufactured overseas for the first iteration of Gather, which was in 2017. So it was a while ago. The product was very successful, but the manufacturing was anything but successful. And I was completely disconnected from the process, so I didn’t really know what was happening. It was just waiting, trying to get samples, working with a group that was monitoring everything.

Long story short, we ended up having two shipping containers, almost a whole shipping container of a bad product we had to sort through. And I’m not sure I’ve actually shared this full story anywhere, so you’re getting some inside baseball.

Chris: Yeah. I want it out.

Jeff: But I felt really demoralized after I put my heart and soul into this product and the launch was going so well. It seemed like the next iteration of Ugmonk as a brand, and there were so many things behind the scenes, but it was just like, this is not working. The wood finishing was not done well, not to the spec that I wanted. So we physically unboxed every single one of them and checked every single one and replaced them and sent emails to customers.

But all that to say, we were like, “OK, I don’t want to go through that again.” We also outsourced the shipping, so we outsourced it to a 3PL (third-party logistics provider) to do all the shipping. Because at the time, my warehouse was my parents’ basement, so it was like, “There’s no way we’re getting two shipping containers delivered to their house.” So I outsourced that. Everything under the sun that could go wrong went wrong. Wrong shipments, wrong charges, mislabeled things.

So I was at a really, really low point trying to go through the thought of, “What am I supposed to do here?” Because this product seemed like it was going to go well. I actually got a call from the producer at Shark Tank that was like, “Hey, we’d love to have you bypass the first three rounds to have you on the show.” And I was just shaking thinking about it, because we didn’t have the product at that point, and there seemed like there were a lot of things ahead that could go well, but behind the scenes it was just going really, really poorly.

We eventually dug out of that and it was a lot of work and I think just trying to do right by our customers, and making sure we stand behind what we do was key. But the moral of the story was I don’t want to do that type of manufacturing. So if I’m going to make a product, it has to be somewhat local so I can go meet with the manufacturer, I can be involved in the process, I can see it happen, we can refine things. And that was all of the learnings I put into this next iteration of Gather. That’s what this past year has been like. And the version of Gather, if you go onto our site now, is all built within a 60-mile radius of where we are in Pennsylvania and we’re doing it with Amish craftsmen and generational woodworkers who have been doing this stuff for multiple generations of craft. We brought it back and we’ve made it that much nicer of a product.

So that’s the long and the short of it, but it was like, “Apply all of those things I don’t want to do to the new version.” And with the new version, although there have still been bumps in the road, it’s been a much better process and we’re really proud to have the product on the site now.

Chris: OK, so it begs the question, how many packages do you still have left from those two shipping containers?

Jeff: Thankfully, we got rid of almost all of them, so what we actually did was we went to our local woodworkers, had them replace and make a whole new run of those parts, used the other parts which were injection molded and combined those, sold them on the site, eventually chipped through and then we sold anything that was lesser at a warehouse scratch-and-dent sale we did. So we actually got rid of almost all of it, which we never thought we would do because we had pallets and pallets and pallets.

Also, one thing I didn’t hit on was that we brought the shipping back in house. Now we have a physical location warehouse in Downingtown, Pennsylvania, which is game-changing because things literally come in our door, we inspect them, we assemble them, we box them, we ship them out. And we deal with all of those customer issues between any part of that journey. And although, again, it’s not the most scalable way of doing it, it’s the only way I can sleep at night because I know we have an airtight machine where we can control the entire process from end to end.

Weighing the pros and cons of staying small or scaling

Chris: Yeah, well, I think literally the afternoon after you and I had that conversation, I went onto your site and bought a bunch of stuff. It’s a great experience. All the boxing and everything was super cool. I still have all the shirts, the Simplify shirt, the Smell The Roses shirt, so all of those kinds of things.

Jeff: And if you emailed, it was literally our one customer service rep who was going to talk to you. And if you need a different size, people are blown away by the customer service because we can be like, “Hey, I’m going over to the shelf right now to check it.” And they get it, and get back to you. And people are like, “This is the best customer service I’ve ever received.”

Chris: That’s amazing.

Jeff: So yeah, it’s more expensive to do it that way. It’s harder. It’s a lot of work. It’s a lot of manual labor moving the products around and shipping and dealing with the returns. But I think it’s a way to do it differently than how a lot of the DTC (direct-to-consumer) brands have been doing things, like to just outsource everything — customer service, shipping, product, send it all to Amazon and then just watch the numbers climb.

And I’m doing the polar opposite of that. We’re more of an old mom-and-pop, craftsman-style business that’s doing really, really high-end products, but still using the internet to get it out there so we don’t have to worry about foot traffic, but we can have 50,000 people walk through our virtual door at any given time.

Chris: Which is amazing. The way you manage the site, everything really, really feels connected. You tried to scale with a manufacturer but it wasn’t quality or personal — which are both parts of your brand.

Jeff: It reflects on me. So at that point, when we were doing overseas manufacturing and launched that Kickstarter, I knew I had to make right on that even at a loss because it’s me. I’m so closely tied to the brand for better or for worse that my Instagram is me, the brand is still me. To an extent, I have a team of people now behind me. So yeah, I don’t know, I think there’s a disconnect when people start businesses and they want to stay anonymous for that reason. In case anything goes wrong, but then you have nothing on the line, there’s no skin in the game. So I’m doing the opposite. I don’t know. I don’t know if it’s a good move.

Chris: You’re all in.

Jeff: Yeah, I don’t know if this is advice or if this is just what I did, but this is where I’m at.

Launching new products for a loyal, highly-engaged community

Chris: Yeah, well how do you balance? If you think about it, you’ve probably read Rick Rubin’s recent book (“The Creative Act: A Way of Being”). It’s like you don’t make anything great if you make it for somebody else. You make it for yourself, and then hopefully it’s an offering and if people love it, great. It seems like you have a similar philosophy though that seems to be a luxury because you still have a business and you’re trying to make a living, right?

Jeff: Yeah.

Chris: So how do you hold the tension between your brand and your core values and making a decent living?

Jeff: Man, I wish I knew there was a magic wand or magic formula to tell people like, “If you follow these three steps, it’ll happen for you too.” I think the authenticity and intentionality behind what I’m creating comes from a pure place. I’m not the best designer in the world and I haven’t done things perfectly and it’s not like every little detail has been perfect, but the intention is to get there and the intention is to always be pushing for excellence. And I think because I’ve done that for 15 years, putting one foot in front of the other, in front of the other, in front of the other, it’s attracted people. Five people here, five people here, 10 here. And it’s built up to a point where I now have this audience of people who appreciate the type of products I’m making and it’s much easier to launch things to them because they’re sitting on the edge of their seats like, “Hey, when’s that new version of Analog coming out? When’s that next version of Gather coming out? What’s the next thing coming out?”

Launching to an audience like that is completely different than trying to knock on doors and say, “Hey, I’ve got a thing. Do you want to buy it?” They’re already coming. They’re basically ready with their credit cards out. It’s like the meme of the guy who’s throwing the cash out the window.

Chris: Take my money.

Jeff: Which is really rewarding as a designer, but I don’t think that comes overnight. I think that came from building this consistent design approach, an intentional approach to how we make products. That’s where I would go with that.

I think Seth Godin has a really good mantra, which is that people like us do things like this. I think I said that right. Basically you’re going to find your tribe, you’re going to find the people who get that. And when you’re marketing to them, you don’t really have to explain it. You don’t have to give them the full list of features and benefits. They’re already in that tribe. So if you’re into Harley Davidson motorcycles, you’re in a tribe. If you’re into high-end guitars, you’re in a tribe. If you’re into high-end cooking or coffee, you’re already primed for that. So the audience I’m selling to, they’re already ready for that. They’re already part of that community. Instead of trying to convince somebody, “Hey, you should write your to-do list on a piece of paper,” it’s totally different.

So I think it’s just a different mindset when you’re not trying to hit the whole general public with an idea and watch your ad come on during the Super Bowl to be like, “I hope I got everyone with this ad.” I’m at a very, very, very small percentage of people in the world who appreciate and understand what I do, but that percentage is big enough for me to make a living and have a team of people and grow a brand.

Achieving high repeat customer rates and lots of referrals

Chris: So how do you acquire a new customer? What are some of the things you do to acquire a new customer? Because you’ve got a lot of products now. I’d say you have a variety of very consistent-looking themes and collections. How do you get a new customer?

Jeff: Up until three years ago, it was completely, completely organic. Meaning word of mouth.

Chris: Word of mouth.

Jeff: Somebody said, “Hey, I got this thing. You should check out Ugmonk. These products are really good or these shirts are really good.” Then we experimented with some paid advertising, but it didn’t really work. Then three years ago, we finally cracked that nut and that was basically because of the product-market fit. So the Analog product really struck a nerve with people and hit a pain point where they were like, “Oh, it’s visually pleasing.” And they had the same problem I did of scrolling their phones and losing their to-do lists and not getting things done. And that product started to work and we were able to put some money behind it and then we were able to reach a much broader audience and amplify that audience, rather than just relying on word of mouth. I would say word of mouth is still a huge part of what we do though, because there are so many people and so many conversations are happening that I don’t know about. Someone said, “Oh, I just told my brother-in-law and he just bought three things and I just told him.” It really goes back to making remarkable products. And those products should spread. The stories will spread because the products are remarkable.

Chris: Yeah, because for you, if you can get somebody to buy, the propensity for them to buy something else is really high.

Jeff: Our repeat customer rate is through the roof. I don’t know the percentage offhand, but it’s very, very high. In fact, there are people who will buy and then buy again within 48 hours sometimes after they get the product — because it’s like, “Oh, I thought this was going to be nice.” And then they get it in person and they’re like, “This is way nicer than I even expected.” So as a designer and design-first brand, I want to make these products just so good that you can’t help but say, “Dude, come check this thing out. This is amazing.” And some people are like, “What’s so great about that?” And it’s like, “OK, they’re not my customer, but that person who is my customer is my evangelist, my advocate who’s like, “Someone’s got to see how great this thing is or how much it’s changed my life or how much it’s helped.” And I think that is way more powerful than any Facebook ad or Instagram ad or any post like that, or any endorsement from a celebrity. It’s like if you actually like what you’re buying, you tell people about it and it’s as simple as that.

Chris: So true. It’s so true. I think one of the reasons to have you back is I think your magic in a bottle is that you’ve developed this brand for quality and it’s personal and you’re intentionally staying at a certain size. You’ve also developed a methodology for getting repeat business. That is a mysterious outcome for a lot of retailers. If you met someone just like you were 10 years ago, what would you advise them to do to be likely to win repeat business?

Jeff: I’m going to repeat myself here, but you need a great product. It’s the same thing if you go to a restaurant and your first experience wasn’t great, how often are you going to go back there? Probably not great odds. If you go there and your mind is blown by how great the experience was, how great the food was, you’re already thinking about when you’re going to go back.

But too many brands, especially in the e-commerce world, miss that, like “I made a decent tumbler, this Yeti tumbler, it’s kind of the same, but we improved on this thing,” but the product is really not that great and people are going to go back to the brand they love and the brand that’s actually doing it really well. I think it’s really, really hard to get repeat business if you’re not putting out an absolutely awesome product because there’s so much stuff out there. Amazon’s the same way. How often do you repeatedly buy something from an Amazon seller? Because you’re buying something, it’s probably going to fall apart. You’re usually not buying it for the aesthetics, you’re just buying it for utility like, “Hey, we need this thing. We need a filter for our vacuum cleaner.”

Chris: Or I need it fast.

Jeff: I need it fast. There’s zero brand affinity. So the next time you go on to buy that filter for the vacuum cleaner, you could buy from anyone. It doesn’t matter. There’s no connection there. Whereas there are brands people have affinities for, the Nikes, the Apples, the Patagonias. People actually feel connected to them because their products are so good. If their products weren’t good, the branding would be nothing. And I think that’s where I’m just about product, product, product. It’s so important to spend so much time perfecting that product instead of shipping it and being like, “It seems like it’s as good as anyone else’s. We have really good marketing.” You’ve got to double down on the actual product to make it something that people want.

Chris: Yeah, and I’m thinking that if you get someone to buy over and over again, do you have this digital fingerprint of people who have bought from you over and over and over again? Can you package that up and say, “Hey Google, and hey Meta, go find me people who look like that.” Is that one of the things you’ve been doing with paid advertising — matching lists and lookalikes?

Jeff: Yeah, exactly. I think the only thing that’s different about it is when you say, “Hey Meta, find somebody like this.” It’s doing the best it can with algorithms and all the tracking and stuff, but it’s not the same as finding your friend when you’re like, “I know Jim down the street, he would love this. Dude, come check out my home office. I just redid the whole thing.” And the people who it brings in don’t convert as well though it’s trying to do the best they can. And we find people, but those people also have no connection to the brand. This is their first touchpoint. They have no history with Ugmonk products. Why is this thing so expensive?

So the challenge of marketing to people outside of our community is very, very different. It’s a different mindset where if I launched a product with you knowing the backstory of Ugmonk and you have some products, so you physically know the brand, when I launch that next thing, you’re much more primed to buy. You’re closer to making another purchase than putting that new product on Meta and just saying, “Hey, find people who might want this thing.” So it’s been challenging I think in that regard to think about those two different paths.

Placing your focus on what you do best

Chris: For sure. Yeah. You’ve got this website. Do you run A/B testing or do you literally just keep running your process?

Jeff: We just run the process. So, we’re a small team. There are four of us, and I’m still doing all the design and marketing. I work with someone who does some of the ad buying, but so much of what I do is based on gut feelings and there is literally no A/B testing. We’re not testing subject lines, we’re not testing anything.

And again, somebody’s going to hear this and be like, “Dude, I can make it so much better for you. We could do all these A/B tests, we could optimize, we could change the color of your buttons and figure out if people buy more. And while there’s some truth to that, I think with the opportunity cost of me spending all of my time perfecting what color buy button appears on the product page versus working on the new product, I always go back to the thought of, “No, I’ve got these ideas, I have these products, I have these methodologies I want to turn into physical products.” So we do very, very little. We’re such a small company that we don’t have anyone to even focus on that stuff. Not to say ignore it completely, but again, if you don’t have a good product, if you don’t have something people want, optimizing and A/B testing a subject line is not going to help you either.

Chris: Which is so true. Well, what is one role in the company that you would be like, “I need a person who’s like me who could do this?” What is the thing you would place your bet on?

Jeff: Helping to draw the stories and ideas and helping to communicate those stories. Pull those things out of me. As you can see, I can’t even get it out right now. Helping to get those stories out of me and my mind into more people’s hands. And by that I mean, people are like, you should start a podcast. You should start a YouTube channel. I want to see the behind-the-scenes process of how you design, how you think, how you work, how you actually use the products you make. So I think having a person who specializes in that, who could take that content and give it to more people would reinforce the whole idea of what Ugmonk is and what the products are because I don’t do a great job at that. It’s like, I’ve made this thing, I released the thing, I show it. I’m really good at the launch stage, but the process of supporting it along the way, I’m not great at that.

So I think, “Man, if I had somebody who could interview people how they’re using Analog, people in all different industries and we could create content around that, we could educate people how to actually implement the system in their work. That’s the missing piece right now.

Chris: So I would call that product marketing.

Jeff: Yes.

Chris: That’s the storyteller. That’s the one who is unpacking the why behind the product, helping to connect customers to it, getting case studies and testimonials, sharing behind the scenes, all that stuff. So that’s powerful. Because I think at the end of the day there’s a missing component in a lot of great product companies, in that they have this gap of being able to articulate the story and socialize the story. Because I do think that’s probably one of the most compelling things about your brand really, the story. It’s your origin story, which we’ve talked about, which is really powerful. I think the way you’ve put this whole community together and how you’ve got the power of this community behind you is interesting.

I follow you on Instagram, and when I think about it, I’m like, “I wonder what Jeff’s going to post and what behind the scenes things I’m going to get.” I almost see you sawdust everywhere with the pencil in your ear doing the stuff, talking with the manufacturers and the Amish people who are doing all of these cool craftsman style things for you. I think that’s one of the biggest gaps for a lot of companies. What do you think would be maybe the biggest impact that a role like that would make in just a business outcome? What do you think would be the biggest impact from a product marketer for you?

Jeff: I think it would accelerate the ability to get those ideas out there for more people to understand them. And by that, I think a lot of people have to warm up to the idea of what Ugmonk is. Why is the price point what it is? Why would I need this thing in my life? It doesn’t always click with people. So it’s a longer path to be like, I’m a stay-at-home mom. I don’t need this product. But imagine if we could have a testimonial of a stay-at-home mom, how she’s using Analog to help bring some calm to the chaos at the house. I think that would accelerate the idea so that more people would be able to understand the thought of, “Do I fit with this brand or is this just some aesthetic brand for designers?” And I don’t want it to be seen as that because I do think there’s power in products that can help people of all walks of life — especially with the products I’ve been releasing over the last couple of years.

It’s never going to be the most affordable and cheapest version. You can always go get a pack of sticky notes cheaper than you can buy our product, but the people who are looking to level up in their life, they want something they’re going to actually use that’s going to help them. I think we could help tell those stories and bring more people into the community more than a Facebook ad is going to just catch your eye. You buy something, it sits on your shelf, you’re not sure what to do with it. There’s a disconnect between buying and actually using a product.

Scaling slowly to maintain the best of being small

Chris: Well, maybe because you have this idea of high-impact, high-quality, personal touch — what is your biggest fear about scale?

Jeff: Scaling the way we’re doing things is going to be really hard. Our supply chain is so localized and can only handle so much volume. Our shipping team, which is just a couple of people, can only handle so much volume. We could hire more, we could get a bigger warehouse, we could do those things, but as the pie gets bigger, each slice of that pie gets bigger with it. So even if we have 1% of customer tickets or customer issues right now, that 1% starts to grow and it starts to become a bigger thing to manage. And if our supply chain with one of our woodworkers or our metal fabricators goes down, now we don’t just have 10 orders on back order. We have 1,000 orders in back order. We have 1,000 angry customers.

I think there are trade-offs at scale that are not always worth it. Money-wise, revenue-wise, if you’re looking to build to sell, you want to scale that business, but just to scale just because… it’s not all up and to the right, it can actually be a higher cost of doing business. But I don’t want to not scale. So I don’t want to stay plateaued where we are, but I still see us as the tortoise, not the hare in that race where we’re just slowly, methodically growing over the next 5, 10, 15 years doing more of what we’re doing in the same way we’re doing it and not outsourcing everything or shipping it overseas.

Chris: When you’re doing reporting just to see how your business is doing, what is a common period or cadence you use to evaluate how well your business is doing financially?

Jeff: Some of it is obviously revenue and number of orders, seeing the average order value and seeing if people are buying more as the products have gotten more expensive or as we introduce bigger collections of products. Some of it is the new versus repeat buying. We want to know how many new customers we have versus repeat customers. And a friend was just asking me, where should that percentage be? Do you want it to be 75% new and 25% existing customers? And I didn’t have a good answer. We’re at 50/50 right now, or somewhere around there. I think that’s healthy because that means we have a lot of new people coming in and we’re not relying just on past customers, but it also means past customers are still coming back to buy a second and third and fourth time.

But to be honest, I’ll go back to the fact that we don’t spend a lot of time on the metrics. We look at those things and we keep on moving. And if there were problems there or things that were trending down, I think we’d want to address them. But we have a much less data-driven, tactical approach. And that goes back to my personality because I’m just not wired that way, which maybe it won’t be the best thing.

As the business grows, it does become more and more important to know all of those things, but it can be a distraction. You could spend all your time trying to decipher why people buy more in October than they did in September and try to spend hours and weeks analyzing that, but we just look at some high-level metrics and keep on moving.

Asking loyal customers for help

Chris: Yeah. Yeah. OK. Well, talk to us about a time you had a lull in your business and what you did to attack that problem.

Jeff: Well, COVID is probably the outlier here. I’ll give you one fun story from that because there’s not a lot of fun stories that came from COVID, but I have a positive that came from it. So March 2020, when everything was, the outbreak was starting to happen, we thought we might have to be locked in our houses for 10 days, and we were like, “What are we going to do for 10 days?” And it ends up being a year or whatever it was. Business had come to almost a screeching halt where there weren’t a lot of people going to buy luxury items or extra T-shirts. We were all like, “I don’t know if I’ll have money for groceries this month.” And I had one part-time employee or two part-time employees, and I was like, “I don’t know what we’re going to do.”

But what I did was I sent a simple email to our list and it was just like, “Hey, we’re still here. We actually have a lot of work-from-home products. We’re a family-run business. We want to make it through this.” And at that time we thought it might just be a few weeks. And that single email generated, I think $20,000 in sales in the next 24 hours or something like that.

Chris: It’s amazing.

Jeff: Which just showed that in building that community for so long, people had our backs. I was getting emails like, “Hey, we’re going to make it through this. I got your back. I’ve just bought a bunch of products.” And tapping into those relationships and that loyal community that has had my back for so long felt amazing because yeah, I couldn’t just quickly run some Facebook ads and hope we generated revenue.

And what happened then was working from home was a thing, but it wasn’t as big of a thing as it is now. People started shopping, we had leather mouse pads, I had the original Gather desk organizer, and people were trying to get set up on their kitchen tables to try to make a semblance of, “How do I work from home?” Then after that, when face masks became a thing and all of us were like, “What’s going on? I’m not wearing these things.” I didn’t want to get involved with any of that. Then our T-shirt manufacturer in Los Angeles sent me an email like, “Hey, I’m allowed to reopen if I can make face masks, do you want to sell these to your customers?” And I was like, “I don’t know.” This was super, super early. So just remember how weird it was in the very early days.

He sent me a sample and it was actually really, really nice. It was the softest material I’ve ever felt. And I posted on Instagram, just one simple post of me wearing the mask. It was like, “Would anybody be interested in these? We want to keep our T-shirt manufacturer going through the pandemic. I want to support him.” And it just took off and it took off to the point that we had our biggest month ever going into selling face masks because people were buying them. And the same thing happened. They bought them like, “Wow, this thing is way softer than all the ones I have here, the disposable ones.” They told their friends or the people who would come up to them in the store and ask, “Where did you get that? I need a cloth face mask like that.”

It ended up being this thing that brought in tens of thousands of customers who didn’t even know what Ugmonk was. They didn’t even know we made shirts. They came in, they bought masks. And that had this ripple effect to get us through the pandemic and opened up a lot of new avenues that I never thought I’d get into. Thankfully, we are past that and we’re completely done with that, but it turned into just pivoting in those little moments where I send an email to my customers like, “Hey guys, we’re still here. We have products. We’d love to stay in business.” And boom, people came. “Hey, here’s a product I think might help us in the next few weeks, months, years,” I sent that email or launched that product and it turned into this whole thing.

So the moral of the story is, one, build that audience you have a connection with, that you can sell things to. And two, is to just keep pivoting. The winding path of entrepreneurship is not a straight line from A to B. The last 15 years have been one of those squiggly drawings that crosses over itself and gets there.

Developing a strong personal brand

Chris: Well, one, that’s a powerful story. Two, just for you to have two parts of that story, one is where your loyal customers took care of you with that surge of sales, and then all of a sudden you’re like, “Hey, I actually want to pay it forward, and let’s keep the T-shirt manufacturer going as well.” What are some of the routines you do and have done to develop such a bought-in community? There’s the product and the personal things you do, but what are some of the consistent, everyday routines and practices you do on social media and over email?

Jeff: From the email side, I still write all of the emails. The majority of them are directly from me to the customers. And there’s a personal approach there that felt like it made sense when we were a small company like, “Hey, here’s a guy designing shirts.” I just never stopped doing that. So when I write an email, it’s literally going from my inbox to your inbox. If you reply back, that’s where a lot of those conversations have started and the crazy connections with people have happened, because they’ll write in like, “Hey, your products have really been helping me and it’s helped my son, he has autism and these Analog products have been…” Powerful stories have happened.

People feel the need or the idea to write back to me, whereas how often do you reply to a branded email? It comes from a big brand. You don’t write back to Nike when they send you an email because you’re not sending it to a person. So the approach has always been to keep that super personal. And I’ve even dripped in more personal updates when it comes to the “Five Things I’m Digging”. Every month, I send out this email called “Five Things I’m Digging”. It has nothing to do with Ugmonk, but it’s just a quick update like, “Here’s what we’re working on, and here are five things I’m into right now.” It could be music, food, design, fonts, anything. And that keeps it human. It keeps people coming back because they’ll picture me on the other side of that email, which is a little bit weird because I’ll meet people and they’re like, “I feel like I know you from reading these “Five Things I’m Digging” emails for so long. I could figure you out.” And I’m like, “I don’t know you at all. I don’t know if you’ve even read my emails.”

But that personal approach has been something I started with and continue to do with social media, email, all of those things that I think are important in a day and age where everything feels completely impersonal. It’s hard to even talk to a customer service rep, let alone the founder of a company.

Chris: Yeah. That’s pretty awesome. The five things you’re digging, that’s definitely a program you’re running. Do you have a certain cadence? Is that every single month?

Jeff: Yeah, just once a month. And it didn’t come out of a strategy session. One month, I had nothing going on with the business to talk about. It was probably when I was dealing with the first round of Gather and had all the issues we were dealing with and just said, “Hey, I hope everyone’s doing well. This email isn’t about me right now, but here are “Five Things I’m Digging”. And I just literally sent that to the list and people wrote back and it was the highest-clicked email, and people were like, “This is awesome. Didn’t know that this thing was out”, or just discovering different branding and different design, different ideas that I come across, and I love sharing that stuff. So it was a win-win. I love finding unique things. I love finding that thing, that special thing, that hidden cafe and then sharing it with people.

And then sometimes I’ll even hear back from the cafe or the designer or the photographer who will share that they just got a bunch of inquiries. “Did you send something? It’s coming from your list.” I love just sharing that spotlight with no affiliation. There’s no benefit to me. But all of that ties back to this idea that you’re still getting the email from me. It’s that personal curation. It’s a connection to me as the designer and the founder. And there are not too many people doing that. And I don’t know if I’m just moving to the beat of my own drum over here making it up, but it seems to be working for our community, so I’m just going to keep doing it.

Inspiring customers to stand up for your business

Chris: I love it. Well, what’s your best troll story? Who’s giving you the wildest DMs? Because you get a lot of good customer feedback, but you have to tell us a troll story since your reviews, all of your reviews are five stars everywhere.

Jeff: Yeah. Yeah. All right, well, so I’m trying to think on the spot here. We had a customer, this would be really embarrassing if this customer listened to it. I don’t know what their name was, but it was about the Analog product. So it’s essentially a wood block that holds a card at an angle. So when the card is sitting on your desk, you can see your card propped up. So picture a place card holder.

And they wrote in saying they really like the product, the quality’s great, but their neck is just really hurting from using the product. And they’re just like, “Ah, I wish you could just make the card stand up.” They literally had the card holder flipped around backwards and had been bending over like this to try to use it, so they sent a picture of it and we were like, “If you flip the card holder around this way where the card fits this way, you’ll be able to see your tasks.” It’s just stuff like that sometimes that cracks me up.

Chris: You’re like, you’re doing it wrong.

Jeff: Yeah, we’ve never shown a picture of it that way. I don’t know where they got the idea, but they were complaining that they had neck pain from our product.

Chris: Oh my gosh. You’ve got to love that.

Jeff: I’m trying to think if there are any other crazy stories, but we get some… I would not say this is an interesting troll story, but we do get a lot of knockoffs of our product, which has been really frustrating. People in other countries usually literally lift our entire product design, marketing, photography, everything. And my fanbase will DM me and be like, “Hey, have you seen this knockoff?” And sometimes they will be the ones writing the nasty emails to the owner. I’m not telling them to do this, but on my behalf, they’re like, “Hey, take this down. This is Jeff’s product. You can’t be selling this.” And sometimes just by guilting them into it, they’ll take it down.

Chris: That’s amazing.

Jeff: But yeah, that’s not really trolling, that’s just theft. It has been frustrating, but as we have more success, that’s part of it.

Chris: Well, you’re not thinking patents and all that kind of stuff, right?

Jeff: No, and I went down that path a little bit. To me, the patent system is not designed for small businesses like ours. You have to have the money to litigate and to reinforce everything. We do have copyright and trademarks, but utility patents are really hard to get. Design patents are not very defendable.

I think at the end of the day, people want the real thing. So we’ll go back to if you’re buying a legacy brand product, you’re like, “I want a John Deere tractor, I want a Patagonia jacket, I want a Rolex.” You’re looking for the actual thing. And there are always going to be people who want the knockoff Rolex because they’re always searching for the fake Nikes and they’re always going to find that stuff. So there’s a market for better or for worse, for people buying the knockoffs, which is terrible that it exists. But then there’s a whole market of people who are like, “I want the real Analog system, the Ugmonk.” But yeah, it’s a really tricky thing to do when everything’s on the internet and everybody can see everything.

Committing to your passions and strengths as an entrepreneur

Chris: What is Ugmonk without Jeff Sheldon?

Jeff: I’m not sure it can really exist. I think it would be very, very different. Somebody could take our IP and our product line and continue it for a little while. But my fear is that the whole human connection relationship behind the scenes, when that trails off, so does our community. I don’t think just the assets of what I’ve created are... They may be sellable at some point, but people are buying into Ugmonk for more than just the products. It’s the ideas and it’s the relationship and it’s being part of that tribe, that community. So I’m not sure what it would look like. I think it would be very different. The curation would probably fall off a cliff.

Chris: Yeah. Yeah. Probably. Could you imagine hiring let’s say, a professional CEO, to work on the business so you could be the evangelist, product, and R&D guy?

Jeff: Yeah, I’ve actually thought about that a lot. If we were to grow even more, I don’t want that CEO role. I want to be the founder. I don’t want to be the CEO and that distinction, hopefully that self-awareness will help, but what a CEO has to do to drive a company is very different from what a founder and the designer of the company does. I was just reading a post recently about how that transition is a big jump. The guy inventing something in his garage who came up with this great idea is not necessarily the guy who’s going to have 500 people under him and move this massive machine and global brand, and I’m much more the guy in the garage inventing stuff. That’s my happy place — lock me away in a room and let me just have all my design tools and all my inspiration and just make those things and create and tangibly make with my hands.

The business side and the CEO part I have to do now out of necessity have been really challenging. And that’s probably the most stressful part of it for me.

Chris: Yeah, yeah. Well you’re driven by, I’d say, a deep sense of values. You have such a unique approach to business. What would you say is the legacy you hope people take with them for how you run Ugmonk?

Jeff: I hope the products we create are put in that category of legacy brands. It doesn’t necessarily mean we’re going to be as big as some of the brands that have been around for 200 years, but I do think of people, I think we talked about this last time, Dieter Rams who designed a lot of the Braun electronics and appliances and that whole system and record players, the legacy he left, left a mark on the design world of this combination of form and function, and where people collect those items. Even if they’re not using that record player, they want to have it in their house because that object is beautiful, it’s unique, it’s useful, it has a certain aesthetic. So even if I’m 1% of what Braun ever did or what Dieter ever did, I want to leave a legacy of those products. If your grandkids found Analog sometime, found it in the attic and took it out, they would still be wowed and there would be some level of awe from the product standpoint that isn’t gone in 10, 20, 30 years.

Chris: It’s amazing. Well, I think it’s really inspiring to see what you do. Think about it, there are so many entrepreneurs out there who would dream of having the loyal base of customers and audience you have, and it’s really been powerful to get to know you and follow you and see the things you do. And it’s been amazing to see that you’ve got this, I don’t know if it’s lightning in a bottle, magic, whatever it is, but the way you go about things is really inspiring. And I think if people could repeat a lot of what you do, they’d really enjoy their business.

Jeff: On that note, I will say you get to see the tip of the iceberg. And if you’ve ever seen the illustration, what’s underneath the water is all the parts people don’t see. And I appreciate that. That means a lot that you see that magic in the bottle and I hope that’s how people perceive Ugmonk. But for all the business owners out there who are like, “Why can’t I have that magic?” There are more things you don’t see than you do see that are literal sweat and tears and going through the actual process of making things and shipping things and dealing with people and dealing with broken parts and broken relationships and all of the stuff that comes along with it that I don’t post a lot of on social media. One, I don’t think a lot of people are like, “Can’t wait to see what terrible things happened to Jeff. That was terrible today.”

Chris: That’s what the memoir is for.

Jeff: Exactly. Yeah. So when I write a book someday, you’ll get to hear even more of those horror stories of the Gather story we talked about with the shipping containers of product. But yeah, I want to keep that magic, that tip of the iceberg people see that shows there is something aspirational about doing something similar. And to really just give people the idea that they can do things differently. My story doesn’t fit within any template of building a business or entrepreneurship. It’s just putting one foot in front of the other and zigging and zagging and we figured out a way to do it with our local manufacturing and our loyal community. Yeah, I hope to keep doing this for a long time.

Rapid-fire questions

Chris: It’s awesome. You definitely have your way of getting it done, which is powerful. I think one of the things that’s been really impressive about the team is that we found a whole different set of rapid-fire questions for you than the previous ones. So we’ve got round two of rapid fire. The hard questions are out of the way. These are the fun questions.

Jeff: I know, but these are the ones people can hold against me. If I pick the wrong cheesesteak place in Philly, then I’m going to be boycotted.

Chris: This is so true. So the pressure’s on. I’m kidding. All right, well what is the essential design tool that you can’t live without?

Jeff: Pen and paper.

Chris: Wow.

Jeff: If everything else was gone, I could still create a lot of what I create. It’d be harder, but if I didn’t have that, just pen and paper.

Chris: Soundtrack or silence while ideating new products?

Jeff: Soundtrack for sure.

Chris: All right. What is it?

Jeff: It is some sort of music that I can’t tell you the lyrics to because I only listen to music for the sound.

Chris: OK.

Jeff: So it’s usually pretty mellow, lo-fi stuff. I always have sounds in my ears when I’m designing, but it’s a very passive way of listening.

Chris: OK. Well what’s your go-to activity when you need a break from designing?

Jeff: Probably playing with my kids. They’re dragging me out in the backyard and we’re kicking soccer balls and throwing footballs, or just going for a walk, getting outside, which I don’t do often enough, but it’s so refreshing. We all need to just get outside more. Being outside is definitely the best thing.

Chris: That’s good. What is your favorite Ugmonk design?

Jeff: My favorite Ugmonk design… I’m going to say the Analog system because it encapsulates everything Ugmonk has been in the past and where we’re moving in the future in a tangible product.

Chris: OK, well done by the way. Well done coming up with that answer. If you could collaborate with any artist — they could be living or historical, who would it be?

Jeff: I would love to have Johnny Ive sit down and give his input and collaborate on some industrial design.

Chris: That would be a lot of designers’ preferred collaboration. That’s super cool. Well, what is one surprising source of inspiration people might be shocked to know you enjoy?

Jeff: Oh man, you might’ve stumped me here. That people would be shocked to know? I don’t think people would be shocked at all the things I would list.

Inspiration is basically osmosis. It’s like taking in all these bits and pieces from all over the place at any given time. And I think traveling is the best version of inspiration because it’s all new and it’s all hitting me in different ways, but I don’t know if I have anything that would really shock people.

Chris: That’s a good answer though. Very good answer. What’s your morning routine in three words?

Jeff: Three words?

Chris: Just three.

Jeff: Oh, man. I was going to say get out of bed, but that’s more. How about “get outta bed”? There. That’s about it.

Chris: You’re like, “That’s what takes a lot of the work.” Well, if you could set up an Ugmonk pop-up shop anywhere in the world, where would it be?

Jeff: Probably Copenhagen. My wife and I were just there and just love the vibe over there. Very design forward. Very cool city. Smaller, walkable city. Super inspiring.

Chris: Man, I remember I had to drive from Kolding to Copenhagen and that bridge. Have you driven on that bridge?

Jeff: No, I actually haven’t.

Chris: It’s terrifying to have a bridge that’s that long. You cannot see the end and you’re just on it forever. That was actually pretty terrifying. Who is an entrepreneur you think we should have on the podcast?

Jeff: Oh, man. I think you should have Johnny Earle from Johnny Cupcakes. I don’t know if you’ve followed his whole story, but he was one of my original inspirations. I think we might’ve talked about this in episode one. Very, very interesting story. Inspirational guy. Completely walks to the beat of his own drum and has done things differently, which has been a big inspiration for me to be like, “I don’t have to do things the same way that everybody else is doing it.” But he’s built a global brand by selling T-shirts with cupcakes on them.

Chris: That’s awesome. Well, Jeff, it’s always great to have a conversation with you. I leave wanting to go do something unique every time. You definitely are an inspiring person and your community is amazing and how you try to help people along the way and how selfless you show up and just how much work you guys put into your business. I really appreciate you coming in and sharing your story with us.

Jeff: Yeah, thanks. I’m an open book, so if people want to reach out to me, DM me on Instagram, Twitter, whatever.

Chris: It’s good. Thanks Jeff.

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