223: Turning a Luggage Problem Into a $32M Apparel Brand with Dan Demsky

Today I’m talking to Dan Demsky, who turned the frustration of trying to pack light while traveling into an 8-figure e-commerce business.

He discovered that merino wool clothing lets you pack far fewer items for a trip. The problem was, most of the brands were focused on outdoor gear—not something everyday travelers would actually wear.

So Dan and his buddies built Unbound Merino, a fully remote apparel brand doing $32M a year.

In this episode, you’ll hear how they used crowdfunding to validate product-market fit and scale without investors, how tariffs nearly wiped out their business overnight, and what it actually takes to run a fully remote team.

Mic Drop Moments

• “I wanted to travel anywhere with just a backpack, and I was trying to find the right clothing to do it. I couldn’t really find it, so I made it.” – Dan Demsky

• “The business model is simple. We create products, we have a good marketing engine, and then we ship them from our warehouse. That’s it. Good products, good marketing, good distribution, and customer service. Just make those things all good. Quite simple, and it’ll work.” – Dan Demsky

• “If there’s one tip I have for crowdfunding is manufacture your own momentum at the beginning. It’s not a ‘build it and they will come.’ Force all your friends and family to give you the momentum.” – Dan Demsky

• 00:00 Starting Unbound Marino
• 01:00 Crowdfunding as Product-Market Validation
• 04:38 Ecommerce’s Hardest Problem
• 06:00 When Tariffs Nearly Killed their Business
• 11:22 30% Repeat Buyers in 30 Days
• 14:02 Using Crowdfunding as a Growth Engine
• 28:42 Running a Fully Remote Team
• 42:02 Should You Do Business with Best Friends?
• 55:30 Advice to New Entrepreneurs

Brad Weimert: Dan Demsky, you started by building a seven-figure agency, then you did a crowdfunding project, which led you to just leave that company that you’ve now turned into, last year, a $32 million company in revenue. Thanks for joining me, man. It’s good to see you.

Dan Demsky: USD, that’s like 300 billion Canadian.

Brad Weimert: I love it.

Dan Demsky: Which is where I’m from, so yeah.

Brad Weimert: So, Unbound Merino is the company. Let’s start with how do you explain that without using the word Merino?

Dan Demsky: We are an apparel company. We make clothing that helps people pack light when they travel. That was always something I wanted to do. I wanted to travel anywhere with just a backpack, and I was trying to find the right clothing to do it. I couldn’t really find it, so I made it.

Brad Weimert: So, that’s such a weird USP to say travel light, so buy my t-shirts for that reason. Why did you land on that USP as a value proposition?

Dan Demsky: Well, I remember going on a trip with an ex of mine, and we got to this place. It was Hydra, Greece. There’s a beautiful little town, an hour ferry outside of Athens, and there are no roads, so there’s obviously no cars, and everything’s up on a hill. And our hotel was right at the top of this hill. And I remember when we got off the ferry, she had this huge luggage set and I had a little medium one, both heavy, both packed. And there were two ways to get your stuff up to the hotel. You could either schlep it up yourself, or you can pay the guy with the donkey. And I was like, “I’m not paying a donkey.” So, I obviously took both of the bags, and we get up to the top, and I’m sweating bullets, and I threw the suitcases on the bed, and we opened it up.

And I remember asking her, I’m like, “How much of that stuff are you actually wearing on this trip?” She’s like, “Honest answer, like 20%.” And I said, “Next time we travel, can we just do carry on? Can we just figure it out?” And she was down. So, I then started researching how do you travel overseas with just a backpack or just a carry-on? And I discovered Merino wool clothing from a Reddit thread. Someone said, “When I travel, I wear Merino wool clothing because it’s antibacterial, it’s odor resistant, it’s wrinkle resistant. So, rather than packing like 14 t-shirts for a couple of weeks. I could pack two, three, or four because you get more wears out of them. And they just performed with a temperature regulation and all that stuff.

I thought, “Oh, that sounds cool. Let me give that a shot.” So, I started looking for Merino wool t-shirts, and while I fell in love with the fabric, all of the brands were made for a different purpose. They were made for base layers for skiing, stuff for the great outdoors, like if you’re going on a canoe trip or something. And I’m talking about the styles. You had these boxy cuts, reflective logos. None of the stuff was something that you would have the versatility to dress up a little bit. You wouldn’t put a sport jacket over one of these shirts. You wouldn’t wear a nice pair of pants and a nice watch and feel like it made any sense. And I was thinking, “Why is nobody making stuff that has that versatility?”

While I had this thought, I also was on this two-year journey of trying to get out of my other business because I felt like a prisoner in it. I just didn’t like being in the services business. It’s like you eat what you kill. It’s always hunting. And I had some friends. I had these e-commerce businesses where they’re just making bank while they slept. And I was like I got to figure that out. So, every two weeks, I’d come up with ideas of what could be my e-commerce product business. And in that moment, I was like, “I think I figured it out. I’m going to make the brand I’m looking for.” That was it.

Brad Weimert: I both love it and find it terrifying because, well, let me ask how you walked your way into it from there. So, found this thing that you loved, seemed like a great idea. Did you have any idea what the total addressable market for that would be for pack light?

Dan Demsky: Zero.

Brad Weimert: Okay. Zero.

Dan Demsky: We’re completely delusional. We were looking for an idea, and when I say we, it’d be me and my best buds. We, literally, would get together once around two weeks, and that could be in the office on the chalkboard or whiteboard. We could be at a bar at one of our places with a scrap piece of paper. We would just pitch ideas, what could be our product, and we had so many terrible ideas. Maybe some decent ones. But none had like the legs that were like, “Okay, that’s the one.” But this one felt right. I pitched to them. They’re like, “Let’s give it a shot.” Challenges, we didn’t have the capital. We didn’t have the energy. We didn’t have the time. We’re running another business.

So, we decided to do a crowdfunding campaign. And the reason we did that was because not only would it, if it worked, would we get money to fund the inventory, but also, if it worked, it means we found product market fit. And we also thought the crowdfunding campaign was a perfect format for creating a business. It’s like a business plan in a sense. It’s like your whole value proposition, the type of sales copy you use, the brand, the imagery, photography. Everything that you need to do a crowdfunding campaign is the same thing you need to open up a Shopify store. So, it’s going to force us to sort of create this thing, take a low-risk shot at it, and see if it works. And it works.

Brad Weimert: And I want to talk about the company and kind of the path from crowdfunding to the rest of it. But you mentioned that you had this agency, you didn’t like the service model, and you had these friends that were doing e-comm, and they seemed like they were killing it.

Dan Demsky: They were killing it. Yeah.

Brad Weimert: Now that you’re in it, now that you’re many eight figures into selling apparel, do you see it differently than you did the shiny lights from the beginning?

Dan Demsky: No. This is where I’m at. We had this vision that we could create this thing, and it could be an eight-figure business. We’d be able to run it from wherever we want. Right now, one of my business partners is in Costa Rica. There’s in Mexico, I’m in Texas. We’re all from Toronto. We’re running the business as usual. We’ll be able to scale this thing, have a bunch of fun, have our own autonomy, have our freedom in life. And it’s not to say it’s easy. It’s not easy, but it’s simple. The business model is simple. We create products, we have a good marketing engine, and then we ship them from our warehouse. That’s it. Good products, good marketing, good distribution, and customer service. Just make those things all good. Quite simple, and it’ll work.

And now that we’re here, I’m kind of like, “Wow, this is exactly what we hope for.” It’s given me freedom. We’re making money. I’m having fun. My partnership with my buddies is amazing. It’s exactly what we wanted, exactly what we hoped for. Now, the challenge is thinking like what’s the next chapter. Because I feel like what we pictured, we’ve fully achieved it. We’re literally right in it right now. And we can sort of rest on our laurels and just continue to run business as usual, by like, how are we going to adjust the goalposts, and where do we go from here? And that’s what we’re in the process of right now is thinking about what the next 10 years will be.

Brad Weimert: So, I’m hearing like 99% of the entrepreneurs being like, “F*ck you. It’s so easy.” What sucks about the business right now?

Dan Demsky: You know, any one thing can throw the balance of the whole company off, and inventory management is really hard, especially with the lead times that we have. They’re really long. So, you make a bet on how much inventory you need to have, and it’s so easy to be wrong. You start to release new products. So, new products cannibalize the sales of other products that you thought you’d sell X, but it’s not quite there. So, now you have all this cash sitting up and inventory in your warehouse. Everything feels like it can go wrong, and everything is hard, and you have to learn on the job. So, it’s always hard, but that’s the fun part, I guess, not to mention we’re a travel apparel product, and then we had a global travel ban. Things like that happen.

We’re a Canadian business with 80% of our customers, and we ship over the border, and then you’re not allowed to ship from Canada to the States anymore. So, that happened. These are like really disruptive things in our business that required us to go all in, and we were at risk of completely going out of business in both of those situations. But that is the fun part. I remember, especially with tariffs, I was actually, for the first time in a long time, I was at a standstill. I was pretty scared. I’m like I have no idea how to deal with this, because in one day our sales went down 80%. I don’t know if you know what de minimis is. De minimis was the loophole where you can ship over the border. As long as it’s under $800, it’s duty-free.

Brad Weimert: Oh, right.

Dan Demsky: So, for us, shipping over almost 99% of our orders are under $800. So, we’re shipping from Toronto into the States, where 80% of our customers are every day a truck’s coming in, driving it over the border, and shipping USPS from Niagara Falls, New York, or Rochester, New York. Just getting to our US customer, no problem. We were running that for years. Trump comes in, de minimis is gone. Now, the duties that we would normally pay on importing were added to the retail price in the customer’s shopping cart. So, imagine at one point, it was 140%, so add 140% of the price to the customer’s order. All our US customers stopped buying in one day, and we’re like, “We’re F.” I don’t know if you swear here.

Brad Weimert: Oh, I really like the word f*ck.

Dan Demsky: We’re f*cked. And that was the craziest week I’ve ever had in business where I’m just like nobody’s buying except our Canadian customers, which is less than 10% of our customers. And we have this team that we’ve built, we have all of these costs, and that lasted for a week, and then Trump rolled it back, but he gave us until Liberation Day. So, now it’s like, you ever see the show 24?

Brad Weimert: Yeah.

Dan Demsky: So, we had one of those timers. We’re like, “We’ve got to figure this out by Liberation Day.” So, that involved setting up an entity in the US, finding a warehouse space. We’re in Dallas now. Finding a team, building a team, hiring. I told you I was in Papua New Guinea before the show. I was in Papua New Guinea. What was this happening? I’m like, “Should I cancel this trip? No.” I just had to check in. I was in Australia in Papua New Guinea. We had to figure out how to pivot our entire business and deal with that. But I remember in that moment, I was actually like, I don’t know what we’re going to do before facing all this. And I got on a Zoom call, like this emergency call with my partners and our director of finance and our accountant.

My business partner was just like smiling. And I’m like, “What are you excited about? This is horrible.” He’s like, “It’ll be fun.” And I was just, “Oh, thank God one of us is having fun.” That gave me the relief I needed because I felt like I had to be the leader. But I’m like, “Oh, we got this. We’ve been through sh*t before.” So, hard things happen, but you pivot, you figure it out. Now we’re a US company and a Canadian company, and we’re back in business, so it’s like hard things happen. But overall, we’ve created a great life for ourselves. We love the challenge. We get to work together. It’s a lot of fun. It’s never easy, but we’re not stressing. We’re not crying about work. We’re not complaining. We made it so we enjoy it the whole way through.

Brad Weimert: Okay. This is the interruption where I’m supposed to take money and let somebody else advertise on the podcast. But I don’t really want to do that, so I’m going to remind you that I also own EasyPayDirect.com. And if you are a business that’s accepting credit cards or needs to, you should understand why we have thousands of people a year come to us off of platforms like Stripe or PayPal, and why they prefer Easy Pay Direct. You can check us out at epd.com/bam. That’s epd.com/bam.

Brad Weimert: Yeah, I think that’s only said by seasoned entrepreneurs.

Dan Demsky: I felt this way when we were inexperienced. I always thought it was fun. I was getting a skiing lesson the other day, and I was talking to my skiing instructor, and he works for some mechanical engineering company. We have President’s Day here. We have Family Day in Canada.

Brad Weimert: I know, it’s hilarious. What is Family Day? It’s just hanging out with your family?

Dan Demsky: Yeah.

Brad Weimert: That’s awesome.

Dan Demsky: Yeah.

Brad Weimert: I mean, I like to talk sh*t about Canadian holidays, but like that’s actually an awesome holiday.

Dan Demsky: Yeah, it’s great. It’s just like, yeah, chill with your family.

Brad Weimert: It’s f*cking better than President’s Day.

Dan Demsky: Yeah. I’d rather chill… Well, it would be cool to chill with some presidents, but you don’t get to.

Brad Weimert: Exactly.

Dan Demsky: But he’s saying at his company, like, he got to choose Family Day or Christmas Eve off.

Brad Weimert: Wow.

Dan Demsky: And I’m just like, it’s brutal. I don’t remember what the point of why I was saying that, but it’s just like…

Brad Weimert: Freedom, entrepreneurship. You liked it from the beginning. Well, look, I think that that’s the mindset perspective thing that is very difficult to I think embody, and some people are born with that, and some people build it over time. My comment before about it being a seasoned entrepreneur lesson usually is that after you get hit in the face a whole bunch of times, you start to be like, “Oh, I’m just playing a game where I get hit in the face,” and that’s part of the game that I play, and I still like the game.

Dan Demsky: You know what? I think you’re completely right because sometimes I’ll hear what people experience in their corporate jobs, and they’re like, “Oh my God, and this happened. This happened.” I’m listening and like, “And?”

Brad Weimert: Right.

Dan Demsky: It’s like, “What do you mean? I had the same day today. This is a great day.”

Brad Weimert: Where my mind goes with those is I’m like, “Why are we talking about this right now? Is there a punchline to this story? What are we doing?”

Dan Demsky: Yeah.

Brad Weimert: Yeah, I totally agree. Well, I want to talk about some of the mechanics of Unbound in your journey, but before we get there specifically, I read an article that Shopify put out that something like 30% of your clients buy a second time within the first month. Is that right? And if so, how do you make that happen?

Dan Demsky: So, a lot of people wait a long time to make that first purchase. We have that question after you check out, “How did you hear about us?” if people want to answer. If they answer a few, it will ask, “What was the timeframe from when you first heard about our brand until when you made your first purchase?” And I think over 60% it’s longer than a month, with a good chunk of those being over a year. Over three months is a large percentage. I don’t remember the exact breakdown, but a lot of them it’s a month to over a year. And I think that’s because it’s a simple product. It’s a t-shirt or a hoodie or a sweater, some pants. Classic, timeless, simple designs, but it’s expensive because it’s a really premium fabric.

So, I think some people, they’re waiting like, “Do I want to buy this thing?” And when they finally try it, it performs as promised, and they realize, “Oh my God, this is actually a whole different level of material.” The temperature regulation. It really is anti-wrinkle. It really never smells. It feels amazing. It’s not itchy like a lot of people think wool should be, and then they just want more. So, that’s the crux of the whole business. I mean, if you really want to get into the mechanics of the business, you’ll be shocked about how simple it really is. We’re not doing any kind of like brilliant hack to make the thing work. We’re good at a lot of the things that we do, but really all we do is we focus on trying to make the world’s…

World’s best travel clothing is what we’re trying to accomplish, so we sweat every little detail in making that t-shirt perfect from like the fit, the fabric, the weight, the drape, everything like that. And it’s a thing that people want more of. When you discover what your favorite t-shirt is and you’ve just got one, you just bought it, you’re like, “This is actually my favorite t-shirt. It’s so much better than the rest of them,” but you have 50 other T-shirts. People then start to be like, “Well, I’m going to get three more of these.” So, that’s what happens. They buy it. They try it once. It’s like the drug dealer model. It’s like you give them a dime bag, and they come back, and then they’re a customer forever because you always need t-shirts. But then they want to try our long sleeve, they want to try our hoodie, they want to try our socks.

Brad Weimert: So, you attribute it really to it just being a great product.

Dan Demsky: That’s it.

Brad Weimert: Crazy. Well, I love that idea. Will you pull this up a little bit? Okay. So, one of the things that sticks out about your path is crowdfunding. Most people see crowdfunding as a one-time thing to launch a company, sometimes to figure out if people, if they should launch a company like product market fit. You have launched multiple products within the Unbound brand through crowdfunding.

Dan Demsky: Three.

Brad Weimert: Three. Tell me about how you see crowdfunding and where it fits into your business model.

Dan Demsky: I think we’re done with it and not for any particular reason other than it’s a lot of work to do it. We did them the first three times because it was a necessity.

Brad Weimert: So, meaning you needed more capital?

Dan Demsky: We needed more money. And we didn’t want to raise money because it was entirely bootstrapped. We just like our life. I don’t want to have to answer to shareholders who are trying to…

Brad Weimert: Tell you to do things.

Dan Demsky: Yeah. I don’t want people to have a say in our business. So, it got to a point, so when we started the biz, we had our first crowdfunding campaign. We had about 2,000 customers from that. That was enough to get started because they started coming back. They started telling their friends about it. But also, it was a nice time for Facebook ads back in 2017 when we started the store, the Shopify store, and we created lookalike audiences of that customer base, and we started growing. We were growing so fast in that first year that we didn’t have enough money to fund the inventory that we needed, again, because the lead times were so long. So, I’m like, “Do I know any people with lots of money that could loan us money?”

And I was able to pull off one little loan. I’m like, “Look, this is not because we’re in the hole. This is because we’re going gangbusters.” And I asked an old family friend that came into some money, I’m like, “Can you loan me $100,000?” And they did, but I only felt comfortable asking for that once. We wrote checks to pay them off. Paid them back. But that gave us a little, you know, it funded a little bit of inventory, but then we needed more right away. I didn’t want to go back to him. I didn’t feel comfortable. And I’m like, “What do we do? Could we go to the bank?” Bank said no. Very conservative banks in Canada. We needed money. No one would loan it, didn’t have a line of credit. We were too new of a business. And we’re like, “Wait a second, let’s just do what we did the first time.”

So, that was why we released the hoodie, like let’s do the hoodie. We made it seem like it was like we’re our next product, but really it was just a way for us to sell a bunch of product way in advance and use that profit that we made on that to fund more inventory. And then we did that again for the women’s line for the same reason, because it was a new category. We’re unsure how many women would buy our stuff. We had a good feeling that it would do well, so we did the women’s line as well.

Brad Weimert: So, crowdfunding has been good to you. Is there a platform that is better, one better than the other? How has your approach to crowdfunding changed, if at all, from the first launch to the last one?

Dan Demsky: So, it’s been so long. So, I imagine there’s a lot of nuance that has changed. We did Indiegogo over Kickstarter for one reason. I think they’re still smaller, but at the time, they were the second place. Yeah. I don’t know which car rental company that says, “We work harder because we’re the second biggest,” whatever. That is true for Indiegogo. And the way that manifested itself in our reality was they had account people who cared about our success that we could actually talk to, that helped us, that cut deals with us. So, with Kickstarter was like fill out a form, fill it, get a ticket, and maybe they’ll talk to you, and they’ll help you. But that’s the way that you play the game on Kickstarter.

Indiegogo, I knew the person. They were helping us. They were telling us, “Here are some best practices. Here are some things to do.” But the most important thing they did, and anyone who is working with a crowdfunding campaign, this would be my tip, is you can negotiate with them to get into their marketing campaigns, which are actually really valuable. So, they said, “If you were,” I think the deal was something like, I don’t remember exactly but, “If you get 30% or 40% funded within the first 48 hours, then we’ll include you in our newsletter.” And I knew from someone else their newsletter drives a ton of business. So, we really wanted to raise $75,000. That was what we actually needed to just get the thing started, sell for $75,000.

But we lowered our funding goal to $30,000, not because we only needed $30,000, but because it was easier to get 40% of $30,000 than $75,000, and I can just call up all my friends like, “Hey, dude, please buy a t-shirt.” That’s what we did. We got every person I knew that I could reach out to. I worked so hard to get them to actually buy something off of our crowdfunding campaign in the first day, so we can hit 40% and then Indiegogo would include us in their marketing. And the way that we did that was I recorded a personal video for each one of those people. So, do you ever get a message in like Facebook or something where someone’s like, “Hey, I just want you to know I’m running this thing. Can you please vote on my thing?” or whatever?

And you just ignore it because you know you’re a part of the mass message. But if you got a video thumbnail that said “Brad.mpg” and you see my face, you’re going to click play. And then you see me talking, and I’m like, “Hey, Brad, I want to show you, I’ve been working on this thing for two years, and I really need your help.” It’s like it was a little more personal, and it was to you. So, I did that for days upon days to every single person I knew, and we just got everyone we knew to fund the thing. And then we hit that. I remember seeing the sales guy, it was my brother, my cousin, my friend’s cousin, and then all of a sudden, we were trending on the platform, and then I started seeing this, “Who’s Hans? I never heard of this guy, some guy in Germany.”

And then the sales started popping up from around the world, and then the newsletter came, and that was worth like $100,000 in sales. And that was it. That was the single best thing we did for crowdfunding. And if there’s one tip I have for crowdfunding is manufacture your own momentum at the beginning. It’s not a build it, and they will come. It’s like force all your friends and family to give you the momentum because that momentum makes other people, first of all, you start to trend, and second of all, people are like look at it and they’re like, “Wow, what’s this? Campaign’s doing well. It must be trustworthy.” So, that’s the best thing that we did.

Brad Weimert: How does the lesson of manufacturer momentum apply to other promotions you’ve done since crowdfunding?

Dan Demsky: You know, something I’ve noticed, we always want to order enough to sell as much as we can. If we’re going to sell 500 or 1,000 units of something, you got to hope that you have that much inventory. But sometimes we undershoot, not intentionally, and it sells out. And you notice this with other products and other brands all the time. Like, when Nintendo releases a new system, it’s always selling out. There’s always a lineup at the video game store. Oh, the Switches are sold out. Sold out again. I’m like, “They know what they’re doing.” They’re doing that intentionally because then there’s a buzz, and then people start selling them on eBay for a little bit more, and everyone wants one, and everyone’s talking about it.

Or like you go to nightclubs, and they make people line up outside. There’s like 80 people in line outside and like 30 inside. There’s something to be said about that. So, that’s not momentum. It’s buzz. That’s always worked really well for us. So, now, instead of trying to have, like I talked about inventory is a hard thing, but when it comes to new products, we try to have about enough, but enough that we know what we’re going to sell out and we like to sell out and see if people are buzzing for it and filling out that form to be notified when it comes back in. And that instructs our future ordering.

Brad Weimert: I think I’m probably in the same camp that you were years ago around Merino wool, which is like, I know of it and I know that the material exists, but the only context I had for it really was like a base layer for mountain climbing, in my case, or outdoor activity. So, you decided, “Hey, I need to create this product for everyday use and/or dress it up, dress it down, but use it casually.” Are there other companies that you compete with right now that sell, and how do you differentiate?

Dan Demsky: The angle we took was unique at the time. A lot of people have a travel angle now, and sometimes it’s straight up. We can see like those people took our copy, which is…

Brad Weimert: Pack light and travel?

Dan Demsky: Yeah. Just like there’s certain… Sometimes we’ll look at our product page, or we’ll see another brand. I’m like, “That’s literally from our product page.” And I think that we were unique on that front, but I think a lot of people are looking for the perfect T-shirt, and we compete with some Merino wool brands that they’re kind of in different categories, but it could be a cotton T-shirt. I think it’s for people who are looking for the perfect T-shirt for them, men or women, and they’re willing to spend on quality. That’s sort of who we compete with. And I find that the ones that I like the most, brand-wise, are not in the Merino wool space. They’re more in the premium to luxury men’s and women’s space.

Brad Weimert: Well, one of the reasons that I asked is because you mentioned this idea of stocking inventory, and I know that the barrier to creating a brand, and I guess it is actually a brand, I don’t know why I air quoted that. Well, I do know why. Today is much lower than it was 10 years ago, mostly because you can buy other people’s sh*t and just put your logo on it and pretend it’s yours and create a brand around it. In the space of Merino, you first and foremost, I heard, flew out to Shanghai to watch the first production run. Is that right?

Dan Demsky: Yeah.

Brad Weimert: Okay. That’s f*cking crazy. So, I want to talk about that, but second, at this point in the game, is it an option to functionally drop ship the product, or over-manufacture and sell the rest of it to somebody else? Or is that off the table for you?

Dan Demsky: I haven’t really even thought about that. I don’t see what the advantage was.

Brad Weimert: Well, I think the inventory thing is what I’m thinking, right? The idea of like having to count, and this is coming from a person that doesn’t have to handle inventory. So, that seems like a nightmare to me.

Dan Demsky: Yeah, it’s the hardest part of the business, and I mean, I watch from afar, and I try to understand it, but it’s like let’s just try to get it right. It’s an ongoing struggle. Fortunately for us, we don’t have seasonality that much in our products. Some products, but we’re sort of trying to make the timeless classic styles. We don’t have a spring-summer line and a fall-winter line. It’s like we have our black T-shirt and we’re always trying to perfect it. Maybe we’ll dial in the fit a little bit iteratively over time, but for the most part, the same stuff that are our core products today, were from the beginning and continue to be.

Yeah. I mean, it’s easy to create a brand. You could have someone else that makes a shirt, and you can just slap your logo on it. But that is not what we’re trying to make. Like, I know exactly what we were trying to achieve. In fact, if this brand existed when I was looking for it, it wouldn’t be something — it wasn’t like I wanted to go get into the clothing business. I had no business getting in the clothing business. I knew nothing about it. It’s because I knew what I wanted. So, if I found this brand when I was looking for it, I would just be a customer telling my friends about it. I’d be coming back in the first month, just like our customers do.

No one was making it. So, we went and figured like, this is exactly how we want the fit to be. This is how we want the trade to be. I knew what– I had a vision of what it should be and we just stopped it. Nothing to achieve that. Knowing very little about how to get there, but we knew what we wanted. Once the t-shirt was on our back, we’re like, we did it. It’s here. And that was what we used to launch the crowdfunding campaign.

And that’s just what it continues to be. It’s just, we now have men’s and women’s, but when it was just men’s to start, we were making it for me. That’s it. Like, I’m making the thing I want. Once I get that, let’s sell it, because there has to be more people like me, people who are not going on the portaging canoe trip or going skiing, like people who are going to Hong Kong or New York, and you might go for a hike, but you’re also going to the cocktail bar at night or whatever. We’re making it more for that, and that just didn’t exist. Not in the Merino wool space.

Brad Weimert: Yeah, I guess where my head went was like, is there a play for you to wholesale it to other people that are selling Merino wool? So, you could stock up on your own inventory, you produce it, and then you allow them to sell it, or you sell it through other retailers or whatever.

Dan Demsky: That might be a good business opportunity, but we’re really trying to build a brand. And I think at this point, we’ve gotten to the place that we dream we could be when we started. And now, we’re like, we can actually take a swing at being a globally recognized brand that’s the best at what we do. I know lululemon has some struggles right now, but they established a category, yoga.

And we think we make the world’s best travel clothing. We sweat every detail to accomplish that. And I think as far as the stuff that you pack when you travel, I think that we could be the best at that. I think we already are, but I think the world could recognize us as the best at that. And that’s about building a brand. It’s not about let’s like, let other people sell our stuff because it’s not really– look, I’m not saying I don’t like money. Money’s great. I want to make money, but it’s not about the money as much as it is about creating something fun and awesome. And I think that’s what we’re doing so.

Brad Weimert: Well, I think, I mean, I really like the distinction between, it’s a good business opportunity, but not what we’re building. Yeah, I think that that’s a really good point of reflection for people. Okay, so you had an agency that you hated that you wanted to get out of, ultimately. Felt like a prison, I think, is the words you used. Now, you have a physical product company, which originally, you were packing and picking yourself and shipping, right? But you were a totally remote company. How does that work? And do you think it would be more efficient to do it in one place as opposed to being totally remote?

Dan Demsky: I think there’s a lot of pros and cons to being fully remote. I really try to optimize my life for freedom and we won’t change yet. So, we do, we have a warehouse in Dallas, a warehouse in Toronto, and our warehouse in Toronto is our company headquarters, but it’s optional. There’s no like come in one day a week. There’s no mandate for that.

But people do go in because they like to, they like to– there’s a little board room, there’s a product design room with all sorts of fabric swatches and prototypes and things like that. And we go in there once a month for lunch, which is totally optional.

Brad Weimert: Once a month.

Dan Demsky: Once a month, we have an optional like team lunch. Then we have the warehouse team. I mean, they have to go in because they’re shipping the product. But I think having a physical space where we can work together would be great. I think there’d be a lot better synergy in collaboration. So, there’s a bit of a sacrifice by being fully remote.

And when we first started, of course, I couldn’t be wherever I wanted. I had to be there myself. I was physically packing the orders myself when we started. But now, it’s like I do go in. I like going into the warehouse. I’m in Texas. I go once a month to be in the warehouse. I don’t have to be there. I choose to be there. I like to connect with people. I think there’s something to that, but no, I think it’s more catered to our life and that’s really we’re creating a lifestyle business.

And I know that’s a bad word for a lot of the VC types, like, ugh, lifestyle. I’m like, isn’t that the point? Like to me, that’s what success is, is the lifestyle you live. Do you live a great life? Are you enjoying yourself? Have you built a life that caters to you accomplishing what you want to accomplish? And that’s building the relationships you want to build, being challenged, having fun, doing cool sh*t. That’s what we’re creating. So, it’s going to be a remote business.

Brad Weimert: Well, that makes a lot of sense for the owners. How do you think about creating culture in a remote first company, specifically one that also has to have a physical warehouse present? What do you do to create culture inside the company?

Dan Demsky: There’s a culture of autonomy. We do connect. So, once a year, we do get everyone together and it’s fun. People actually like to be together and people want to get together more, but you can do it kind of on your own. Be the people that a lot– most of our team is in the Toronto area, so they do meet in person. But they do it autonomously, like when do they want to and when do they need to. Especially the product team, they need to do fittings and need to touch products, so we don’t hire those roles.

Some of them we have remote because they can be, but mostly, those people need to be in person, but they can do it as they wish. A lot of great people come to work with us because we are remote. Like, I could think of a few people and I asked them, I said, why did you– we went through the hiring process. They seemed very excited to want to work with us. We hired them and I asked after, like, so why did you pick working with us? Like, why were you excited to do three rounds of interviews with us and go for this job? And a couple of them were honest, said, well, one of the top things was you guys are fully remote. Like, I can live my life the way I want to.

And because we give them that gift, they don’t want to mess it up. They want to continue to live their life the way they want. They say, “I’m going to go to Vancouver and work for three weeks.” Great. We still have to work together. We still have to sort of align on times. One went to Georgia, not in the United States, the country Georgia.

Brad Weimert: Right.

Dan Demsky: So, six hours ahead, he adjusted his time to work with the company. We give them autonomy. We respect them. We have a good culture of letting people do things their way and not babying them, not micromanaging. So, it’s a culture of respect. That’s what our culture is. And it’s a gift. It’s a gift to be able to give people freedom. So, the culture is sort of built around that. It’s like, I mean, it’s in our name, it’s unbound. Like freedom is at our core. Like we create freedom for our own lives, for everyone’s lives. Our product is giving you freedom to whisper around the world with less stuff. Like freedom is something we talk about all the time and it’s something that I think our culture is built through.

Brad Weimert: Are there any non-negotiables for remote staff to keep things together as a company?

Dan Demsky: Yeah. This is the big one. We know very clearly what our goals are for the year. We do a little bit of the three to five-year sort of paid vivid vision. You talked about Cameron Herold before we do that.

Brad Weimert: Yes.

Dan Demsky: And we break that down to one year, and then we have quarterly strategic planning. So, that is the one in-person thing that we do three times a year. In the Q1, we do it remote, but that’s one time we need to be together. The people that do our strategic planning, we get together and we pick what our departments are going to work on that year and that quarter. And when we have that plan, we break down what’s going to have to happen every week.

When you know what you need to do every week and it’s completely visible to the rest of the company, do it however you want. I don’t care if you want to take three days off randomly. We don’t track vacation days. We don’t care. Did the thing get done that needs to get done? And if we all align on that and it relates to our revenue targets, our profit targets, the main objectives that we’re trying to accomplish within a year, those things of the quarter, those things down to the week, if they’re getting done, we live your life however you want and people do. So, the non-negotiable is just get done what you said you were going to get done. That’s it.

Brad Weimert: So, a couple things. One, that sounds like you have to be very deliberate about making sure you have a concrete road map, at least for the first year or for one year at a time.

Dan Demsky: One year.

Brad Weimert: I love that, which is something that we all should do, and some of us do better jobs than others as entrepreneurs. So, I feel like there are some people that are made to work remotely and some people that should not be trusted to work remotely. How can you tell when somebody is going to be a good fit for a remote environment or not when you’re hiring them?

Dan Demsky: That’s a good question. We’ve gotten pretty lucky with our hire and we haven’t over-hired. We don’t try to build a team really, really fast, but we look for people who are self-starters and they’re kind of entrepreneurial and they take the work seriously. Like, I mean, we all take the work really seriously. I don’t think I’m a workaholic, but I don’t even need vacations. Like, I never feel like, oh, I’m burnt out. Like I can work all the time because it’s fun.

I think I kind of see that in other people. The people who take the work, they want to do great work, not because it’s just the way we’re wired. So, just look for people that align on those core values of having that entrepreneurial spirit and grit. And we’ve been lucky at finding them, but really, it’s not that hard to figure out over time. If you have a really clear road map, as you said, and we do, that’s the one thing we’ve done really, really well.

We didn’t invent this stuff. It’s from Scaling Up. You know the book Scaling Up? I saw an EOS book here. It’s quite similar. We have played that playbook from the beginning when we started, and it was just me and my two business partners. We had annual strategic planning meetings, quarterly strategic planning meetings, weekly meetings, and daily huddles. We did all that stuff and we showed up. And this has been for 10 years now. We have not– I mean, maybe there’s been a vacation here, maybe this person who’s sick once, but we never miss it. Ever. And we never have.

And I think that’s the thing that we’ve done really good is we’ve painted that picture. And when you paint that picture, it’s really quite simple. We know what needs to get done. Did it get done or not? And if someone is not getting their thing done, so we have a dashboard and everyone has what their rocker priority is for that quarter, and every week, it’s a spreadsheet, a shared spreadsheet, and every column has the milestone of what they need to do that week for the quarter. So, I can look at one person’s task and see, this is what’s going to get done next week. That’s what’s going to get done the week after that. This is going to get done the week after that.

And when we have our weekly meeting, they come in and they mark it, red, green, or yellow. They highlight this column in the spreadsheet. And if it’s red or yellow, we talk about what’s going on? Are you stuck somewhere or something going on? Sometimes, it’s like, you know what? I just got busy and I’m behind, and it’s okay. It happens. The whole company can see that they’re behind. And people who mark red every single week, they basically fire themselves.

Brad Weimert: Right. Yeah, I love that.

Dan Demsky: That’s it. Just get it done. And nobody wants to show up to that thing with two weeks in a row, yellow or red.

Brad Weimert: No.

Dan Demsky: Including myself, I’d be embarrassed. And I don’t, I mean, no one’s going to fire me, but I would be humiliated and that would be bad leadership.

Brad Weimert: For sure. I think that one of the best forms of accountability is transparency.

Dan Demsky: Yeah. Everyone could see everything.

Brad Weimert: Yeah. Anybody that prides themselves on being unbound and having flexibility in life and they use that as an excuse to not be disciplined in their approach to execution, listen to the last three minutes again, because the fundamental of what you just said is within a concrete structure that you never, ever, ever, ever miss is where you find the opportunity for you to live whatever life you want to live.

Dan Demsky: Yeah. And people realize it. I could think of our graphic designer, that’s the guy who went to Georgia. Like he said, he is like, this is such a gift. I have to take it so seriously. I want to do great because here’s the deal. I get, it’s like, his life or his words. But basically, what he was saying was, in exchange for me doing great work, I get to have a great life. And I’m like, I don’t care. I don’t need to baby you. I don’t need to make you pick which holiday you get on, like live however you want to live because that’s the way I want to live. But I have a responsibility to the company as all of us do to make it work. And we live great. The team’s amazing. And it’s going to be 10 years in December. We’ve only had two people quit ever.

Brad Weimert: Crazy.

Dan Demsky: Ever.

Brad Weimert: Wow. That’s nuts. All right, so clearly a high value. So, you did $32 million last year. If I said you can never work fully remote again as a company, but I’m going to add $30 million to your top line, would you do it?

Dan Demsky: You mean, just me or the whole team?

Brad Weimert: The whole team.

Dan Demsky: No.

Brad Weimert: $100 million?

Dan Demsky: No. No, because it’s like, what am I doing it for? I’m from Canada. I don’t know if you know what Canada’s like in the winter.

Brad Weimert: Get the f*ck out.

Dan Demsky: For the past four years, I decided, I’m like, I don’t like winter.

Brad Weimert: Yeah, I understand. That’s why I live in Texas, bro.

Dan Demsky: Yeah. So, I went to Buenos Aires, where January and February is summer. So, we’re going to have to be in Toronto in the most miserable winter of all time, hating my life because I have more money. For what? And eat more caviar. Like what do– like, it’s fine. So, no, unless I could do something with that money that would dramatically change some, like a bunch of lot, like, they say enough is as good as a feast.

Brad Weimert: Yeah, I love that phrase.

Dan Demsky: I don’t need $100 million to live in agony. Not worth it. I’d rather have less millions and live an amazing life.

Brad Weimert: Well, I love that approach and coming from, I grew up in Michigan, so we’re a Canadian neighbor. And yeah, I definitely…

Dan Demsky: We’re a hockey fight away.

Brad Weimert: We are a hockey fight away. Yep. A shared hockey fight, perhaps. All right, so the other thing that I want to hit on with you that I think is unusual is you started this with childhood friends, and are the three of you in the company now?

Dan Demsky: Yeah.

Brad Weimert: Equal ownership distribution?

Dan Demsky: Yeah, it’s slightly different because of how we started, but…

Brad Weimert: So, two of you started it, then you brought one in later?

Dan Demsky: No, no. We all started it, but because it was a side project, there was different capacity to go full on. Like I just dropped everything. Like I had a little bit of savings. I was evaporating my savings, I was all in.

Brad Weimert: Amazing.

Dan Demsky: My other partner could do that. He had two kids. He had a toddler and a baby. He’s like, I can’t go all in on a company where I was paying myself nothing to start, right? I’m like, I’m in. So, I’m like, okay, well let’s talk about. Like, I’m willing to do this, but like, let’s shuffle what the equity is and if this thing’s ever worth something, that’s what I’m risking it for. That was how we just split it up, but we were very explicit about those conversations early.

Brad Weimert: Well, that’s exactly what I want to talk about, because like modern wisdom, starting a company with close friends is a terrible idea.

Dan Demsky: Yeah, yeah. It’s not wisdom.

Brad Weimert: Yeah. And your approach is totally different, which is, so give me your perspective on that first, and then I want to talk about kind of the architecture of this because I think it’s super relevant for people that have a good working relationship with somebody in their life, but it is crossing the friend-business barrier.

Dan Demsky: Well, do you ever beat someone who works in some corporate environment and they just hate the people they work with?

Brad Weimert: Somebody told me this the other day when we were recording, Brian Luebben, actually. I think the interview just dropped recently, but he cited some study and said, there are only two reasons that people quit their jobs, and one of them is they hate the people they work with.

Dan Demsky: Right. You spend more time with people you work with than anyone else. Seems like a good life hack to like the people you work with. And who do you like more than your best buds? I love those guys. I mean, I hate them half the time, but there’s a lot more to that too. I mean, another thing is if you are really close friends with these people, there is a strong likelihood that you have a lot of alignment on core values because you’ve self-selected each other to be buds along the way.

Aligning on core values is one of the great lessons I’ve learned in business is have clear core values and hire and fire on those core values. So, when you work with your friends, core values, it’s baked in. It’s like there’s alignment there. If you work with friends and your friends don’t take the work seriously, I think that’s a recipe for disaster. Fortunately, we all take it very seriously, and we have different ways of approaching what that looks like and we argue about things and we argue about ideas, but ultimately, we all want the best for the business and we want the best for each other.

No one’s trying to speed the star of the show. It’s like, we all want this thing to work for each other and for ourselves and for the business. We have each other’s backs. There’s a talk series in Toronto called Fuckup Nights where entrepreneurs share like stories of when they’ve really messed something up, which is kind of a cool concept to like learn from the failures.

Brad Weimert: Totally.

Dan Demsky: And I was watching this one woman speak about starting a business with her friend. She said, business and friendship don’t mix. It’s true. And I’m thinking, disagree, but let’s hear your story. And she was talking about one of her friends and how much she admired this person when they started and she told the whole story and I’m like, wow, that sounded like a really nice start. She’s like, but like, because we’re friends, it’s like when we had those meetings, it’s like the meeting didn’t happen. We didn’t show up.

And I mentioned like, I was specifically thinking about talking about our strategic planning and our weekly meetings, how we’ve never missed one because I didn’t realize until I saw that woman speak, how much that was a part of the equation of success for us. My friends and I, we take it seriously and we show up for each other. If I have a meeting with my friend, I’m not going to be like, who cares? It’s Andrew. I’m not going to show up. I show up. I respect his time. He respects mine and we respect the business.

So, as long as you have an alignment of core values, which you should, with your best friends, I think you need to have complementary skill sets. I got lucky with my best friends having complementary skill sets. To me, I think that’s an important thing because if you’re both the same, you have the same strengths and weaknesses, it might not work. But if those things work, it’s literally the best thing that could ever happen. Because I get to work, spend most of my waking hours hanging out with my best buds. We would do this thing for free.

Brad Weimert: I love that. So, mechanically, if you were funded, for example, you’d have– well, actually, let me just frame this a different way. There are companies where there are owners and then there are employees of the company that execute. And at some level, there are owners and then there’s a CEO and a COO, et cetera, a CMO. There’s a clear delineation of the owner owns, and then those people have roles in the company.

And then you have your situation, where you have owners that have different roles in the company. Do you stick to just the roles in the company or is there some point in time where you say, hey, I know that I’m the CEO, but the COO wants something dramatically different and while I have the final say, because we’re all owners, we’re going to vote on it together?

Dan Demsky: Is there– sorry, I…

Brad Weimert: Is there a delineation sort of between ownership and roles in the company and is it firm, right? Because like, technically, or as most– I shouldn’t say technically, but as many companies would run, the CEO’s got the final word on it, period.

Dan Demsky: Yeah. We’re very good at separating who makes decisions where. And me as a CEO, I have accountabilities to the business as it relates to vision and growing culture and things like that. And I have the say on certain things. But we split out where the decision making is, and sometimes, I don’t have the final decision. That’s just the way we run.

So, we have a head of product and we make it very clear to her, like, I’m going to tell you exactly what I think, but I’m going to let you make the final decision, and I just let go. That’s a big part of our culture is autonomy, letting people have it. We are owners of the business and that means we have the equity in the business. The role of that stops there.

We are also on the team. We’re like employees of the business. I’m the CEO. Andrew is a COO. Dima is a CMO. And we have clear job descriptions, clear road maps, scorecards. We review each other. We just treat ourselves like employees of the business, and it has nothing to do with our ownership.

Brad Weimert: I love that. Do you think that those responsibilities are different than a normal company? Or do you think that they’re informed by the fact that you are owners?

Dan Demsky: No, I think they’re similar. I think we look to other companies to sort of model how the organizational structure should work, because business is interesting because it’s the one of the most figured out things in the world. It’s like how you manage the relationships, how you manage your monthly, weekly, daily meetings, all that stuff people have figured out because there’s an incentive to do so. There’s money to be made. So, if there’s money to be made, people will figure this thing out.

So, we just try to run on best practices. And sometimes we find the best practices don’t work for us so we tweak it a little bit. We have our own intuition in it, but we’re just trying to rip off and duplicate the things that work. So, running a good company with a head of visionary-type person like myself, and then the implementer-type people like Andrew and Dima. We just try to run that way. We just basically follow the playbook.

There’s so many good playbooks. We love Scaling Up. Scaling Up is like our Bible. It’s like, whatever, like, Genesis 32:63. That’s the way we look at Scaling Up. It’s like a Bible to us, but we interpret it a little bit differently.

Brad Weimert: As people do with the Bible.

Dan Demsky: Yeah. It’s our Bible.

Brad Weimert: Is there a…

Dan Demsky: Verne Harnish is our Jesus.

Brad Weimert: Yeah, I love that. Is there a criteria by which one of the owners could be fired from their role?

Dan Demsky: Whoa. That’s a good question. We never really thought about that. Maybe. Maybe, but you know what? We haven’t really had to give that a lot of thought because we’re lucky and that all of us take it really serious. And we all really show up. And sometimes we find the business outgrows us in some ways and it’s our responsibility to step up and we help each other get there. And sometimes we hire people to fill the gaps of where we’re falling short. But no, we’re here to stay.

Sometimes, Andrew is the star of the show. Sometimes Dima, I mean in terms of just like has grown, like outgrown us for a period of time. We’re always just trying to pull each other up. We’ve never once talked about letting one of us go for any reason.

Brad Weimert: So, Gary Keller, who started Keller Williams, famously refers to contracts or agreements as disagreements because the only time a contract is relevant is when you have a disagreement. Are there any contracts that you have in place or that you wish you had in place that you think are imperative when you’re working with friends?

Dan Demsky: When we did our shareholders agreement, we had all of the tough conversations, where it’s like, what happens if one of us dies? What happens if one just f*cks off and doesn’t want to work on this thing anymore? And we just aligned on what fair was when things were good. We’re just starting. That shareholder’s agreement exists and all of the decisions were made nine years ago. I couldn’t tell you a thing about what one of those decisions are. We have never looked at it once, but it’s all there.

So, if something really problematic happened, we’ve made that decision. Like, what if? I don’t even know, like what happens if they wanted to push me out. There’s something in there. They’ll have to buy me out somehow. We degreed, we all aligned, and I think clarity is very, very important. We had it. We weren’t thinking, oh, we’re fine forever. We might not be. We’re fine right now. Knock on wood. We continue to be. Yeah, so we have our disagreement contract somewhere. Just haven’t had to use it because we’re having fun.

Brad Weimert: I love it, man. I love it. Well, I think it’s awesome to hear a million different ways to run a business and I love hearing both that you can operate from the lens of we’re all buddies, we want to do this, we’re having fun doing it. And also, don’t get it twisted. We laid the foundation the right way, and part of the reason that it works is because we have a clear structure that allowed it to be this way.

Dan Demsky: Yeah. And we work really hard and it’s like, I asked both of them recently. Why do you think this works? Like, because a lot of people say business and friendship don’t mix. I think it’s literally the best thing. I think there’s no better work that you could have than to have figured out to start a business with your best friends. It’s the best situation if it works. And asked them both. Actually, some of the things I said to you was just words I stole from them.

But one thing Dima said was it feels almost like primal. It’s like you imagine like in a past time, you’re in a tribe and you’re going out for a hunt. It’s not just showing up to work some job. It’s like we are hunting, not just for ourselves, but for the tribe. So, the work I do matters to the collective to keep this thing. It’s like, it feels like I owe you guys the best I have to give.

And I’m like, I totally agree with that. It’s like I owe it to them to read books and get smarter. I owe it to them to meet people and get ideas. I owe it to them to go to bed at night knowing I put in good hours today. Hours that mattered, not– some days, I have bad days. Some days, I scrolled a little too much that day. I wasted a little bit too much and I feel bad. That wasn’t fair. That’s not how I want to show up for these guys. So, I think it’s motivating to– it’s not a free pass to just do, go be lazy, take days off. It’s like, it’s pressure’s on even more because you owe it to your buddies and we want us to all succeed and do well.

Brad Weimert: What advice do you have for brand-new entrepreneurs starting out today?

Dan Demsky: No two paths are the same. The one thing that has been– I think it’s the, you know, cliches are normally true. Like, you hear a cliche that you’re like, it’s, ah, I’ve heard that a million times. They’re cliches for a reason. The one that is strongest for me and I think is the best piece of advice is you’re the average of the five people closest to you. And I’m very, very picky. Or no, I’m picky about the people I’m around, but I push really hard to be around great people. That’s why I go to these– I met you at an amazing entrepreneur event. I strive to be around these people, and when you are, the dots start to connect.

You find that book you need to read. You see that person who’s doing that one thing really well, the bar is raised again and again and again, and you realize what you’re capable of. If there’s a single piece of advice I’d give to any entrepreneur, regardless of whether they’re starting out or not, is strive to be around people doing amazing things. Try to be the dumbest guy in the room and that lays a foundation for everything else.

Brad Weimert: I love it. Dan, thanks so much for coming to the studio, man.

Dan Demsky: Thanks so much, man. Thanks for having me.

Brad Weimert: F*ck yeah.