How independent brands like Myles Apparel are growing in a world of Nike and other giants

Today’s guest is Ryan Moses, the cofounder of Myles Apparel. They make things like that jacket you heard me talk about with Noah Kagan in this interview.

They make a specialty line of menswear and activewear and we’ll find out why the world needs another line of activewear. I also want to find out how they survive in a world where we already have Nike and Under Armour.

We’ll find out in this interview.

Ryan Moses

Ryan Moses

Myles Apparel

Ryan Moses is the cofounder of Myles Apparel, a specialty line of menswear and activewear.


Full Interview Transcript

Andrew: Hey, everyone. My name is Andrew Warner. I’m the founder of Mixergy, where I interview entrepreneurs about how they built their businesses.

And a few I guess it’s been months now ago, one of my past interviewees, Noah Kagan, came to the office and we went out for a run. And the whole time we were running, instead of looking forward, I was looking like this, like this, and I did it because I really admired the jacket that he had on. I thought, “It’s kind of weird for me to point out something about a jacket.” But I couldn’t help it. I said, “Noah, that’s a really impressive looking jacket.” He said, “Yeah? You like it?” I said, “Yeah.” He said, “It’s Myles.” I said, “Who’s Myles, and what kind of a nerd did you take it from?” He said, “No, it’s Myles Apparel.”

I never heard of it, but I was about to stop to write down the name, I think, and he said, “I’ll send it to you later on.” So we kept on running. Then what I didn’t realize was when he said, “I’ll send it to you,” I thought he meant, “I’ll send you the name of the company. He actually bought me the jacket.” And if you heard my interview with Noah, you’d know that I felt a little awkward about it and appreciative too.

I’ve got the jacket right here in a bag. I’d like to open it up — in an envelope — and I’d like to open it up in this interview because in addition to sending me the jacket, he also introduced me to the founder of Myles and he said, “Andrew, you should actually have an interview with them. It’s a really interesting company and a great product.” So that’s what we have here today.

Ryan Moses is the cofounder of Myles Apparel. They make things like that jacket that I can’t wait to open up and wear, and they have an overall specialty line of menswear and activewear. And we’ll find out why the world needs another line of activewear and frankly, also, how did they survive in a world where we already have Nike and Under Armour and where Amazon is shipping everything directly. Why are they able to survive and grow as an island unto themselves in that kind of competition? I want to know how independent brands are growing. I’ve noticed that is a trend. A lot of smaller, independent brands are just growing outside of Amazon and on their own ecosystem.

All right. This whole interview is sponsored by two great companies. The first will help you hire your next great developer, designer, MBA, so many others. It’s called Toptal. The second is the company that we use when we want to close sales. It’s a CRM called Pipedrive, but I’ll tell you more about those later. Ryan, welcome.

Ryan: Thanks for having me, Andrew.

Andrew: Ryan, I’m going to ask you a question that I know the answer to, but I want to know if you feel comfortable saying it publicly, because I never reveal anything people tell me privately. The question is: What’s your revenue for 2016?

Ryan: Sure. We are in seven figures, the $1 million to $5 million range at this point.

Andrew: Closer to $1 million or closer to $5 million?

Ryan: Closer to $1 million at this point, but that’s changing quickly.

Andrew: Okay. Are you guys privately held? Do you have funding?

Ryan: Privately held and completely bootstrapped.

Andrew: Completely bootstrapped.

Ryan: Yes.

Andrew: Okay. And you’re not a guy with experience in this. You’re a guy with experience in branding. What did you do in branding?

Ryan: Yeah, branding and more journalism before that. I was a writer at a newspaper, and then when I moved to San Francisco, I ended up working at a consulting firm in the hospitality industry of all things, helping four and five-star resorts improve on their brands. Then I found myself in the apparel industry now.

Andrew: What did you do to help them improve their brands? Give me an example of one brand that you specifically improved?

Ryan: Sure. Well, this wasn’t a four and five-star resort, but I did a project working with the NBA, where we would go out and improve fan experience. So we would go to a game and take meticulous notes on every single aspect of everything that got presented to the fan at the game.

Andrew: You mean on the big board, whatever they were showing?

Ryan: Yeah, in-game entertainment, that sort of thing, down to food service and presentation and quality.

Andrew: Why? Why would you do that?

Ryan: To make it for the NBA to know what’s going to get people from getting back from their 60-inch flat screen TV with amazing HD resolution. They actually want to come be a part of this. What is going to make this exciting for them?

Andrew: I see. You’re looking to see what goes into this experience, and once you have that list, you’re going to find what are those key elements here that bring people out, right?

Ryan: Exactly.

Andrew: I see. What did you discover was one of the key elements that would bring people out?

Ryan: One of the key elements was something as simple as an usher being ready to show you to your seat, having a personal interaction with somebody to make you feel like you’re part of this community.

Andrew: How would you know that? If you’re just keeping track of what goes into the NBA experience, how would you know that the usher was so important to people’s experience that that’s what would get them up from —

Ryan: Because we would look at it across every single arena in the league multiple times and keep seeing that that was an experience that people were commenting on, that people were enjoying.

Andrew: How would you know they enjoyed it, surveys or were you watching their faces?

Ryan: Just observing their interactions.

Andrew: Every time an usher would come over, you’d see a sense of relief.

Ryan: Yeah. It’s a meticulous database. We had all these questions that were consistent across every single test.

Andrew: Where you could go and ask them or you would observe or both.

Ryan: They’re observations.

Andrew: All observations? I see. Okay. Interesting.

Ryan: Yeah. That was one area we were testing of many.

Andrew: Okay. Then you say to the NBA or team you’re working with, “The ushers are much important than you realize. It’s more than just helping someone who’s lost. It’s showing someone that we have a concierge service. They are a VIP, and this is an important evening in their lives. Let’s emphasize that and make sure that nobody gets to come in without an usher.”

Ryan: Exactly.

Andrew: I see. Okay. So this is you. Then suddenly, you send an email to the founders of Huckberry and Taylor Stitch. What did you like about — let’s take a look at Huckberry. What is Huckberry, and what did you like about it?

Ryan: Sure. Huckberry is a men’s online retailer. They curate up and coming brands, a lot of outdoor gear and menswear. What I really loved about Huckberry was the way that they told the experience, a lot like what you do, actually. It wasn’t just pitching a product, but it was pitching a lifestyle around them. Their emails, I think, are top in the industry. They’re the one email I open up every single day and read.

So, coming from a journalism background, I reached out to them and just said like, “Hey, you guys are some of the best storytellers out there in the startup world. How do I work with you?” And I kind of struck up a relationship with their cofounders, Rich and Andy, and kind of went back and forth in emails for several months.

Andrew: You said, “I just like your storytelling so much, I want to bring all the talents that I have— talent as a reporter, talent as a guy who’s helped big companies with their brands, I want to work with you because I love your product so much.”

Ryan: Exactly. Yeah.

Andrew: I see. They’re a blog that also links out to other products, like I’m seeing shirts and shorts here and travel bags, etc. and then they get a commission on all the sales they make, is that right?

Ryan: Not exactly. I don’t want to speak too much on their business model. But they’re more of like just a classic retailer. They’re not like drop shipping most of these products. They’re actually selling them from their warehouse.

Andrew: I guess I think because of the way the site is laid out, I don’t think of them as a retailer, even though now that you mention it, of course they are. It just feels like a blog of products that some writer curates and loves, but I see it. Right. There’s a shopping cart right at the top of their site. There’s all the stuff that you’d expect.

But the part that I notice, the part my eye goes to — right now I’m on the tactical scrubber and soap — the very first thing I can read about it is the story. It’s actually headlined, “Story: Manly grooming essentials with the Braun to clean away the dirt of any day’s hard work. Duke Cannon makes grooming essentials that are built — dare we say overbuilt — to persevere in the face of some seriously grimy adversity.” I see. Okay. So you said to them, “Hey, I love your brand. I want to do something with them.” What’s Taylor Stitch?

Ryan: Taylor Stitch is a menswear brand based here in San Francisco. They have an amazing feat of releasing a product a week, which I just think is insane if you know anything about the way apparel production cycles go. Yeah. They’re just really cool, Americana-style clothing. I think they’re doing like kind of the California cool vibe better than anybody else out there.

Andrew: And they’ve partnered up two independent companies to create their own product and that product was Myles?

Ryan: Exactly. So Taylor Stitch, founders of Taylor Stitch, the founders of Huckberry, they share an office together. They’re buddies, they’re entrepreneurs. They saw this space in activewear that — Huckberry was looking for an activewear brand that they thought would speak to their guy. Taylor Stitch knows how to make great clothes. So they saw an opportunity to join forces and create this little baby brand called Myles.

Andrew: Why Myles, by the way? When I first heard Myles, it sounded a little bit nerdy to me. It didn’t sound like this cool activewear brand that would fit in with Huckberry’s design.

Ryan: Yeah. I wasn’t part of coming up with the name, but my understanding of it is Myles is obviously a play on the miles you run, this kind of idea that fitness is about those actual miles and not about the finish line, kind of more of a journey than a destination attitude. Another thing that’s a little bit deeper that we don’t go into that much, Myles was the first king of Sparta. So it has a Spartan lifestyle kind of connotation to it, where there’s an emphasis and value on being healthy and living minimally.

Andrew: Okay. All right. So they had this brand. You were emailing them at the time. Did you know they were coming up with Myles at the time?

Ryan: No. We were just chatting about maybe opportunities for me. Huckberry uses a lot of content marketing on their journal to write great stories about how people live this kind of outdoor lifestyle and use some of these products. So I was like talking to them about maybe freelancing there. I actually saw they were creating Myles on their Twitter. I was scrolling through their feed, saw this brand. As soon as I saw it, I immediately emailed the founders with a link to this and said, “I just saw this. How do I become a part of this?”

Andrew: Okay. Then you become a cofounder. What does it mean to become a cofounder?

Ryan: Sure. So they launched the brand, and obviously they have two growing businesses already. So they were looking for somebody who could come in and kind of run day-to-day and execute on strategy. So I came in and just talked to them about that position and kind of earned my place at the table through sweat equity, just being the guy on the ground floor who’s actually going out and doing some of the dirty work on some of these big picture ideas they have.

Andrew: Why would they make someone the cofounder who had no experience in clothing? Why would they make someone the cofounder and leader essentially of the company? What’s your title?

Ryan: General Manager.

Andrew: General Manager. Is there a CEO on top of this?

Ryan: That’s not really the way we’re structured. We call them the board, basically, the four founders internally. But they kind of have the direction of the company, and I go out and execute it, but I do have input on decisions we make.

Andrew: I see. Okay. I’ve got a sense of how this works. Still, you don’t have any clothing experience. Why you and why would you take on that responsibility when you didn’t have clothing experience or manufacturing experience?

Ryan: Curiosity had a lot to do with it. I thought it was something I could handle. Knowing that, for instance, Taylor Stitch has such a handle on apparel production, we had somebody there who could drive that. So I would have some great teachers in that area and trusting my ability to be able to share the story of this brand and kind of get a crash course in entrepreneurship from these guys.

Andrew: Yeah. I get it. Frankly, I don’t know how much experience the Huckberry guys had before they started it.

Ryan: I think that’s a really common story you hear from a lot of founders is they just find something they think is cool, is a great idea, or is a product that they want and you’ve got to figure out all the rest.

Andrew: It seems like you just had the confidence to say, “Look, I want this job and I can do it right. I want to take on more responsibility and I can do that.” And as a result of all that, you got to lead the company.

Ryan: Yeah. And when you say lead the company, it’s not like that happened — it’s not like they dropped it on my plate one day and suddenly it was now you’re running Myles on your own. It’s something that’s grown gradually over the last two years, where I’ve picked up different areas of the business.

Andrew: Okay. How are you feeling here in this interview knowing that I interview entrepreneurs, the founders and now you’re the guy who came in as a cofounder but not on day one?

Ryan: Sure. You know, I’m —

Andrew: I’m sensing some quivering your voice at times.

Ryan: Oh, really?

Andrew: I want to make sure you’re feeling comfortable, and I also like to point stuff out like that.

Ryan: No. I’m feeling good about it. It’s interesting to talk about, because I’ve listened to your podcast before and it’s interesting you try to talk about it from — you talk a lot about like that origin story, and I wasn’t actually there on day one. So it’s interesting to come in from the perspective of, you know, day whatever it was, 90 when I joined. So I’m trying to kind of come at it through that lens.

Andrew: Yeah. I think you’re in a good position. I’m just kind of pushing because I want to know where — I want to ask the kind of questions that the audience would have, and I think it’s totally reasonable to have the questions that you have about like where you are within the company and it’s totally reasonable for the audience to ask it.

Let’s go on with the story. So now you come in here. They have this idea. You’re starting to come in and take on more leadership. You decide that you’re going to start looking for customers.

What I think is really interesting is the way you guys got customers, the way that Noah didn’t just say, “Hey, it’s Myles,” but led me to the brand, introduced me to it, gave it to me as a gift and the way that you guys even got him as an evangelist. I want to talk about that. Let’s talk about the influencers like Noah. At what point did they come in? Did you do it before you created the product or after?

Ryan: It was — I mean, there was a list of people who we wanted to get this product in front of as we were producing it. They were producing it.

Andrew: I see. So, as you do this, you make a list of people and you say, “These are our ideal users, our ideal evangelists, our ideal first speakers or first promoters,” right?

Ryan: Yeah. Exactly.

Andrew: What were you looking for at that point?

Ryan: Guys who had a background in health and fitness, guys who were early adopters, who would look at something and say, “What is it about this that makes it different from other products?” and would go and share that story with other people. So, basically, we were looking for mavens, men’s fitness mavens, men’s fashion mavens, those kinds of guys.

Andrew: When I Google your name, I see Tim.Blog with a post from 2015, where he’s linking to you guys in his email and on his site, where he says, “Check out these everyday shorts.” Did you give him the first pair of shorts?

Ryan: To Tim Ferriss?

Andrew: Yeah.

Ryan: Yeah. That came from a relationship that he has with Huckberry and those guys, those founders.

Andrew: How does he have a relationship with Huckberry?

Ryan: I think they’ve worked together. He put together a shop on their page, I want to say right around that time, early 2015.

Andrew: A shop meaning all the things that he loves from Huckberry all united on one page. He links it to his people. He gets a commission, and he gets also to introduce them to stuff that he loves.

Ryan: Yeah. I don’t know exactly how that relationship all came to form. That wasn’t my area of the business.

Andrew: Okay.

Ryan: But part of that was giving him a care package of a lot of these products, and Myles, our pair of everyday shorts, which are these four-way stretch athletic shorts, are one of the things that he was given.

Andrew: Okay.

Ryan: And that blog post definitely caught us by surprise because it wasn’t something that after he got them that we then reached back out and had a long discussion about it. It was several months later, I woke up and checked our site traffic and noticed it was just suddenly through the roof and went through our referrals and saw where it was coming from and was like, “Oh wow, Tim Ferriss has called us out in his email.”

Andrew: Yeah.

Ryan: And posted about this. It was a nice surprise to wake up to.

Andrew: Anyone else that sent you that kind of traffic or got you big attention?

Ryan: He’s been the biggest one. The other big ones are — some of the products have been featured on some pretty big blogs or talk about at Gear Patrol, that first year that we had the product, it was one of their top 100 products of the year. So that sent a lot of traffic our way. At this point, we’ve gotten a lot of press from Esquire and Men’s Health, Runner’s World, who have all done reviews on the product and given us some nice quotes.

Andrew: And again, it’s you guys actively finding the people, the media outlets you want and giving them product.

Ryan: Exactly.

Andrew: This sounds so simple or so basic, but how do you know what size to send them, or do you send them every size?

Ryan: No. We strike a relationship with them first. We don’t just — I mean we have taken some shots in the dark and just sent somebody a care package. We reach out, find their email address. We tell them a little bit about the brand, send them a link to the product, say, “What do you like? What colors, what sizes do you like? Is there anyone else on your staff that would like to try it?”

It’s kind of amazing how you do that, get that in their hands, and then they tell a friend about it and then maybe they know somebody who’s working on a story for another publication who wants to try it. Then we start getting inbound requests. It’s kind of, like you said, it’s simple, but it’s amazing how that kind of product seeding can amplify.

Andrew: So the process is step one, find the list of people who are your ideal. Step two, obviously, find their email address. Then you send them an email saying step number three is we’ve created this new brand. We’re really proud of the shorts. Here’s why the shorts are different. I want to ask you about that. It started with shorts, right?

Ryan: Yes. It started with a pair of what we call the everyday shorts.

Andrew: And here’s why the everyday shorts are different. And do you in that initial email say, “Would you like a pair? Can we send it to you?”

Ryan: It depends who we’re talking to. I have said, “We’d love to get a sample in your hands and see what you think.”

Andrew: Otherwise it might be, “Tell me what you think of this brand or how can we promote it,” or anything soliciting feedback.

Ryan: Exactly.

Andrew: Then you say, “Would you like a pair? Tell me what color and what size, and we’ll send it out to you.” Then you send it out. What do you? Do you follow up afterwards? Do you check in to see what they think of it?

Ryan: Yeah. Follow up when we know that they received the package, give people a little time to put it to work. That’s our thing is like go run in it. Go sweat in these. You’ve actually got to wear them. Don’t just pull out a package, feel them and say, “These are my thoughts on this product.” Part of it is using it. So, yeah, then we’ll follow up and keep the conversation going. Then maybe ask, “Is there an upcoming gift guide that these might be a good fit in?”

Andrew: Okay.

Ryan: But our most successful ones have just come because people have gotten excited about the product and have found a reason to write about it.

Andrew: Without pushing. Without coming back to Tim Ferriss and saying, “Did you wear them? Did you like them? Can you include them in this top five list you send out?”

Ryan: Exactly.

Andrew: All right. I’m going to open mine up in a moment. But first, let me tell people about Pipedrive. One of the reasons that I like to ask you, Ryan, about what the steps are to getting a sample in someone hands and then getting them to write about you or recommend you is because I like to know people’s processes. And the second is because I knew I was going to talk about Pipedrive, this software that’s sponsoring that’s designed for stuff like this.

If you guys were using Pipedrive and if anyone out there is listening and says, “I’m going to copy Ryan’s system. I want to do the same thing to work with influencers,” then here’s what you would do in Pipedrive. You lay out each step of your process in its own column. So, column one would be suggested people we want to work with. Column two would be find their email address.

Column three would be send them an email saying, “We just created this new product and we want to know what you think of it.” Column number four would be, “Can I send you a pair? Can I send you a sample of it?” And column number five might be a follow up to see, “What did you think of it? Did you get to use it?” and in some cases, “Would you also include it in a gift guide?”

Five simple columns just to get you started. And then every time you have someone who knew you were suggesting, you create a card for them in Pipedrive. That’s just as simple as filling out a little information like their name. Put that card in column one and then you just keep dragging it from column to column. And because Pipedrive is meant for collaboration, you might not even find the email address. Maybe a virtual assistant will see that you’ve added a new person to column number one and that virtual assistant will find that email address and move that person to column number two.

That’s what Pipedrive is all about, keeping your sales process or persuasion process really organized and allowing you to collaborate with a team of people. We use it to book guests like Ryan Moses. He was in column number one at some point when Noah Kagan suggested him. And he then moved to column number two, which is approved until someone on the team went in and looked at Myles and made sure the numbers were strong and the company had a good story, etc. Then we all collaborated as a team to pre-interview him, to recommend that he keep following through our process until he comes here to do an interview.

If you’re out there looking to close a sale or persuade people to do anything, you need to be organized and you need a system that will also give you stats and tell you, “Here’s how many people you reached out to this week. Here’s where you’re failing. Here’s where you’re succeeding.” That’s what Pipedrive is all about. I’ve used them for years and recently they came on as advertisers and now I’m proud that I get to talk about them more formally.

Not only that, because they’re advertisers and we insist that our advertisers give some kind of deal to our audience, I can tell you guys that if you’re listening to me and you use this special URL, you’re going to get two months free of Pipedrive. Frankly, if Myles had this, within two months, they could get all the influencers to try it and even close up their account and move on with their lives. That’s how generous this free offer is. My sense is if you use it, you’ll be able to do the same thing in two months, but you’ll love it so much you’ll want to stick with it for life. Here’s the URL to get the two months. Go to

All right. Ryan, I’m going to open this up.

Ryan: All right.

Andrew: I’m excited about it.

Ryan: Yeah.

Andrew: Do you do any branding around the package right now? Do you look at me opening it and say, “Where are Andrew’s eyes bugging out? Where are Andrew’s eyes not bugging out?”

Ryan: Yeah. That initial unboxing experience is something that we do prioritize, and it is big for us.

Andrew: I like that you have your logo right there on the bag.

Ryan: Yeah.

Andrew: I also like — this is kind of a small thing, but a lot of times when I get products, I don’t know what it is. I forget that I ordered it. But also even in the form, there’s some random like shipper, drop shipper’s address. I don’t know who it is. And you guys are shipping this directly from your offices?

Ryan: No. We have a warehouse.

Andrew: I mean from your warehouse.

Ryan: This one, because it was special hand-delivered to you, came from our office.

Andrew: Noah is the best freaking gift giver I’ve ever met, and he actually gives me such —

Ryan: I remember you talking to him about that.

Andrew: Sorry?

Ryan: I remember you guys talking about that when he was on.

Andrew: Yeah. I get a little uncomfortable with how generous he is, because how am I going to repay him — forget the gift. I could repay him for this. I can’t repay him for noticing that I loved it and not saying, “Dude, get your own. Stop trying to be me,” and instead saying, “Andrew, I see you love it. I’m going to surprise you and give this to you.”

Ryan: Sure. So this is our elements jacket, right?

Andrew: This is the jacket that he wore. Perfect fit too.

Ryan: Nailed it.

Andrew: This is what I really care about. This feels really right. I feel like the fit is more important than anything else.

Ryan: We agree. That is our number one priority when we’re developing something new.

Andrew: I feel like it’s hard for me to fit — this is way off-topic here — it’s hard for me to feel right in clothes because I work out so much that I’m too skinny for a lot of things.

Ryan: Interesting. Yeah.

Andrew: What do you think?

Ryan: It looks great.

Andrew: Let me tilt it down.

Ryan: Yeah. It looks like it was made for you, custom.

Andrew: Pretty good, right?

Ryan: Yeah.

Andrew: This is really good.

Ryan: I’m glad you like it.

Andrew: That guy’s good. See, now I’m going to constantly think about how he gave this to me and instead of being really grateful, in the back of my head, I’m going to think, “This is too nice. How do I repay him? Do I buy him a car and surprise him with a car?” I don’t know why my head goes to stuff like that. But as long as we’re like in douche chill territory, I’ve got to be honest with you.

Ryan: I really appreciate you comparing our jacket to a car in terms of value.

Andrew: It’s not just that. It’s that he noticed it. And I like the details of this. This is not a regular sleeve, right? This is a sleeve that’s got this little rubbery thing here, but it also goes a little longer here. There’s like stuff about this that feels special.

Ryan: That’s kind of part of our process is where can we put in little details that are not too sporty and not something someone’s going to say, “That person is on the way to the gym,” but you’re noticed as you wear it as being functional and being performance-driven.

Andrew: Let’s talk about the product itself. The first thing you guys came out with is shorts. The world is full of many shorts. I could go into any Target and find shorts. There’s a Nike store not too far from me that has shorts. Why is the world so in need of new shorts that you guys had to create a new brand? What was missing?

Ryan: The idea behind the shorts is that every guy out there has been wearing the same pair of ratty, baggy gym shorts since high school PE class. So let’s give him a version of those shorts that has the same performance function. They’re super comfortable. They have four-way stretch. You can go run a marathon in them if you so choose. But make them a little more structured so they’re not so drapey, not so flowy, that if you were to wear them out on a weekend to brunch or whatever, they wouldn’t look out of place. You could put an oxford shirt on with them and it would totally look just fine.

So it’s about that versatility. It’s about minimizing how many clothes you need in the closet. So that’s the idea behind the shorts. They’re just a little bit more structured in their fit, a little bit more tailored. You talk about being a thin guy, getting something that really fits you and isn’t just billowy and baggy. That’s the idea we’ve taken with all the other products that we make.

Andrew: Do you really look out at the world and say the world doesn’t have this right now the way that maybe if — like Pipedrive, when they were starting out with their software, they had this idea for columns as a way of leading people through a sales process. They could look out in the world first and see, “Does someone have this?” And if not, then we have to create it. If someone does have it, then why be the second player doing the exact same thing? Do you do that when it comes to style, or am I being too anal about it?

Ryan: We do it to some extent. Is there something about this that we can do slightly differently? A lot of it is also in the way that we talk to our customer. We like to speak about health and fitness in a way that’s not specialized, in a way that’s not so driven by like this need for six-pack abs and like pushing yourself like to and beyond your limits. The way we think regular guys work out, think about health, think about fitness and the way they wear their clothes. That translates into the product, that whole philosophy.

Andrew: Do you bring people into the office and have them try on the product and make sure it fits right?

Ryan: Yeah. We go through several fit sessions with guys of different body types to really dial in sleeve length, everything.

Andrew: My dad used to be in — he was a manufacturer of women’s clothing and basically his MO was he’d go into a store, he’d say, “What’s selling really hot right now but it’s too expensive?” He’d find that and then he’d go quickly make it in the U.S. and turn it around and sell it for like $5 instead of the $30 that it was going for before. He definitely had people, he had women who would come in who were the exact shape he needed and they would try on the clothes to make sure it fit. Is that the way you guys do it too, that you have one for each size that is your model, your base?

Ryan: No. Most fit sessions are with somebody who we feel is the perfect medium. There’s always the search for somebody who’s the perfect medium.

Andrew: How do you find them?

Ryan: We’re lucky enough to know a lot of guys who are around that area, so we’ll try it on all of them. From that, we will then adjust the specs for the other sizes based on that so it’s a good scale.

Andrew: I see. It’s not that you have a perfect medium and a perfect large and a perfect small.

Ryan: No. We have a perfect medium and we try that on them. The way the sampling process works with clothes, they send you a medium to try on.

Andrew: You make it first, then you sell it. Do you ever do anything to just make sure that there’s enough demand for a product before you sell it, before you make it?

Ryan: We have presold. I think when they launched the shorts originally they were on presale. Since then, we’ll send out little notes to some of the top 10% of our customers and with little details and say, “Which one of these do you like better?” If we have a couple ideas that we’re totally split on and everyone on our team can’t come to an agreement, we’ll let the customer decide.

Andrew: I imagine that when you’re trying to figure out what to sell, you do the same thing. What you do is you look at Huckberry and you say, “What’s selling right now? What are people asking for that we don’t have? Based on that, let’s come up with our own take on it?” Is that right?

Ryan: Yeah. I think Huckberry is a great source of market research for us because, like you said, we can see what kinds of things they’re carrying and coming up for that next season, figure out where there’s a hole in our line they need to fill.

Andrew: You see what are they selling, what’s missing. What’s your process for figuring out what people are asking for so you know what to make?

Ryan: Talking with people on the Huckberry team about what are they looking for. They have buyers and they’re out looking for brands. We say, “What do you think your guy would really like coming up for this fall?” They’ll say, “We really think there’s going to be a great push for that jacket, for instance, a great running jacket.” So that really drives what items we’re going to sample and start to develop.

Andrew: Okay. And then do you go back and do the same process again? I’m looking at SimilarWeb to see where you get your traffic. It’s Esquire and Tim are two of the biggest ones that’s in your traffic. Do you still go back every time you make a new product and say, “Hey, Tim, I know you liked our shorts. I thought you might like this jacket. I know you like our shorts. We just came out with a new V-neck.” Is that the process too?

Ryan: Yeah. We’ll send people who have spoken highly of our product in the past samples of our new things when they’re ready.

Andrew: I guess I come from a direct marketing world and so in my head I keep thinking, “How much money are we spending on clothes? How much money are we getting back in sales?” I imagine that’s not the way it works. It’s more, “We have a budget for handing it out. Let’s make sure we pick the right people. We’re not going to be so anal that we track how many sales come in from him so we know how much every dollar in pants equals in dollar of sales,” right?

Ryan: Yeah. Essentially, we’d love to get it to that point where it’s that scientific, but at this point, being in a young company, yeah, it’s kind of about moving fast and getting things out to people. It’s a small investment on our part to send somebody a pair of shorts and follow up with them a couple times. So we feel like we have some room there to hit a few singles and then hopefully somebody becomes a homer.

Andrew: All right. There was a problem with manufacturing at one point, right?

Ryan: Yeah. When I first came on, we realized that we had drummed up a lot of demand for the shorts and we just didn’t have any to sell. That was something I realized quickly coming from a branding perspective, I was going to have to fix the problems with production first.

Andrew: You have to fix production?

Ryan: Yeah. Like I said, our founders have two other companies they’re working on full-time. Part of my deal with them of coming in was I was going to learn everything I could about this business. So I got a crash course in apparel production and was at the factory weekly checking up on everything, learning about what goes into this process and what questions to ask, what areas to be concerned about. So that was invaluable experience in those early days when I first came on.

Andrew: How did being a journalist help you ask those questions and understand what the problems are and how to solve them?

Ryan: Yeah. I think that had a lot to do with why I wanted to become an entrepreneur, and my favorite thing about being a journalist was getting assigned a story that you literally may have never heard of the subject when it’s assigned and you have two days to explain it to a wide audience.

So being an entrepreneur, a lot of it is about knowing what you don’t know and finding good mentors and finding people who can teach those lessons and not being afraid to say, “I don’t know anything about this. Where can I find the resources to get some help? Who do I need to ask to find the answers quickly and efficiently?” So that’s what I did in those early days, especially when it came to the production side of things. I didn’t know how to make a T-shirt.

Andrew: “I don’t know the answer to this.”

Ryan: Being okay saying that I think is a huge advantage to anybody in a new field.

Andrew: But you can’t just go to the Taylor Stitch guys and say, “You guys are making all these other clothes anyway, make this.”

Ryan: No. They have their own priorities. Our goal for Myles is for it to be able to stand on its own. Now, at this point, we have our own production team and our own vendor partners.

Andrew: Where’d you find the vendor partners?

Ryan: Partially through contacts like Taylor Stitch, asking who they’re working with and then asking those people if they know anybody, if we’re on the search for the perfect zipper for that jacket, for instance. It’s those kinds of details. And then trade shows, go do a tradeshow, go booth to booth, tell them what we’re working on.

Andrew: You’re constantly saying, “Who can make this jacket for us better? Who can make it faster?”

Ryan: “Here’s our idea. Can you help with us? How can you help? What can you do?”

Andrew: Then do they make samples for you before you get to buy the full production?

Ryan: Yeah. A lot of manufacturers will take our idea and make a quick sample.

Andrew: Okay. What was the problem with the production before?

Ryan: More about just being on top of it, like you were talking about having a process, knowing when does the fabric have to be at the factory, when does the mesh for the pocketing need to be at the factory? At what point do they need our final PO?

Andrew: And the stuff just wasn’t there at one point, right?

Ryan: Yeah. There are unforeseen things, like there was a strike by dock workers at one point that held up — we needed like one little piece for the shorts to get our drawstrings to get delivered to the factory. That held us up for weeks. You’ve got to roll with those punches. There’s nothing you can do about it. That’s not even something for apparel that I even knew was possible.

Andrew: The problem with the T-shirt, that didn’t have anything to do with the dock workers?

Ryan: No. We have some issues with our first T-shirt, and that was just a learning opportunity. That was, again, not knowing what questions to ask.

Andrew: What was the problem?

Ryan: One thing I learned was different fabrics can dye up a little bit differently depending on what colors you’re using. One of the colors we used did not want to work with this fabric for some reason. We got a delivery and we opened the box and we just feel it and we go, “This isn’t right.” So that was kind of one of those early, “Oh shit,” moments, for me just going, “Wait a second, we can’t put this out. We’re a young brand. We’re not going to put out a product that we think is inferior,” and just biting the bullet and deciding that we can do something better before launching it.

Andrew: I’m trying to see what’s different about your T-shirt. Again, I feel like the world has enough T-shirts. Why do we need to make another one? The thing that’s different just looking at the images is it kind of curves down in the front and in the back.

Ryan: Yeah. It’s got a little shaped hem, basically. That, for us, was it’s a little sportier, but not so sporty, again not so sporty that people would look at that, “That person is going to the gym and that’s it.” It’s a T-shirt that comes from — for our lifestyle, we come to work, a lot of us bike to work. We need something that’s going to breathe, that’s going to be quick drying, and then a lot of us will take a break at lunch and go for a run. By having a T-shirt like that that’s a little sporty, made of a quick drying fabric, it saves us having to change shirts one time per day. We feel like that’s benefit enough and a reason enough to make it.

Andrew: Okay. I’m going to talk about my sponsor and then I’m going to come back finish with this set of questions. I want to understand how you sell. In a world where people are used to going to Amazon or a couple of really high end stores or specialty stores, how are companies like you building brands online, getting customers to buy from you and what do you do to stand out?

I’m noticing, as I said before, there are a lot of companies like you, where there’s one thing they’re specialized in and they sell it on a Shopify store directly to people, or they have their own site with just basic shopping cart software and they sell stuff that makes sense. But how do they even get anyone to notice them? I know when I want to buy anything, I go to Amazon or I go to two or three online stores that I’ve known forever. How do you get attention from people like me? Or maybe I’m not the right person. Let’s talk about that.

First, I want to tell everyone about a company called Toptal. You’ve heard me talk about them forever and I’ve said to you, guys, I have experience with them for hiring developers and designers, but one of the things the founder told me is they also have MBAs, people who can do and help you with the business side of the business.

That reminds me of how many entrepreneurs I’ve interviewed who struggled for a long time to figure out what’s the ultimately pricing? Well, Toptal has an MBA who can help you go through and understand what the right pricing is for your business, where you’re going to make the most money based on your past sales and based on your customers.

It also reminds me of the founder of Ranker, who said that he didn’t go out and raise money for one of his follow on rounds because it was just so tiring to do the spreadsheets, to go through that process and for some reason, he imagined he had to do all of that himself. Well, he ended up doing it himself and raising money, but man, was it a hard slog.

What I wish I could do is go back in time and say to him, “Look, there’s Toptal. Toptal has MBAs. Everything that you wish you could do faster, better, they have an MBA who they’ve screened who can actually do that for you.” Sometimes these people are right out of school and they’re looking for work before they figure out what they’re going to do long-term. Sometimes they’re entrepreneurs who have sold a company and are just looking to kick around and try to figure out what to do next and this keeps their mind sharp.

It’s that kind of group of people that they have at Toptal. As with their developers, if you want to work with them, you talk to a matcher at Toptal, they will understand your needs, they will understand your concerns and then they’ll help match you with the right person. If you need a developer or a designer or now if you need an MBA to help you with the finance of your business, go to this special URL where they’re going to give us an incredible offer full of free hours with their people after you sign up and get started with them.

Let me give you the URL where you can actually look this whole thing up and understand how it would work. That is, Top as in top of the mountain, tal as in talent,

I noticed you were taking some notes as we were talking. Was that about like your whole process for getting customers and standing out?

Ryan: This is just a habit left over from my journalism days. I always have a notebook next to me. I was actually writing down a little information about that sponsor.

Andrew: Toptal. I notice, actually, that a lot of my guests write down information about Toptal and many of them ended up being Toptal customers. I forgot to say top as in top of the mountain, tal as in talent, Toptal. The reason I have to say that is because apparently I mispronounce Toptal or I jumble up all the letters together.

I feel like I get a sense of where you guys get your customers. Huckberry, Taylor Stitch both sending you some traffic and you’ve decided you’re going to target certain media outlets like Esquire and certain personalities like Noah Kagan and Tim Ferriss. Is that essentially it, or am I missing something else?

Ryan: We do a lot of marketing on social as well, Facebook and Google.

Andrew: What do you guys do on Facebook and Google that works?

Ryan: I think the big part about it for us is, like you said, there’s definitely other activewear brands out there, but in our imagery and in our copy, the way we talk to our customers is we want to talk to them in a way that shows them that we are guys like them. We made this product for guys like us. So, in a way, that really builds trust with the customer so they don’t feel like they’re working with a corporation, and that gives them a reason to want to give us a shot. That’s what we’re asking for, just give us a shot and we think you’ll like this product better than you’ll like what you’re getting from some of those big corporations and making sure we emphasize like we offer free returns, we offer free exchanges. If you don’t like it, you lose nothing.

Andrew: I’m looking at it. What I see that catches my attention is beautiful shots, the three guys, two of them have especially powerful chests. All three of them are running. So you had to find models that are fit —

Ryan: Part of it is those guys aren’t models. Those guys are guys that we know who are a friend of friend. We’ve made an emphasis on not using fitness models.

Andrew: I see.

Ryan: Those guys don’t look like real dudes. Most guys don’t have the time to spend six hours in the gym. So have guys that have, you know, good builds, because on the weekends, they’re out mountain biking, they’re out running, they squeeze in a boot camp class every once in a while.

Andrew: The photo is beautifully shot. It feels like that’s an expensive shot, isn’t it?

Ryan: We’ve scouted out location. It’s someplace here in Northern California. We have an extremely talented photographer on hand. That was one place that we needed to devote some resources early because —

Andrew: It’s a full-time photographer who’s part of the team?

Ryan: Yes, full-time. They’re basically our creative director.

Andrew: So if you guys have someone, this bearded dude, who’s out climbing some rock structure, which I guess now I can expect is in Northern California, your photographer comes up with that spot and says, “Let’s find a friend of a friend that can do this,” and then he goes out and takes all those photos until you find the right one. That’s what you share on social media.

Ryan: Yes, that’s pretty much the process.

Andrew: Do you get customers from that?

Ryan: Yeah. Our social media strategy has been very successful for us. I think it starts with the product seeking like we were discussing earlier and getting that — we like to take a show don’t tell philosophy. So we need other people to show that the product works. We can say over and over again that this is a great pair of shorts, but having somebody like Tim Ferriss or somebody at Esquire say it for us is going to be so much more powerful. So then using those endorsements and getting those in front of somebody who we think would like the product on social.

Andrew: You find someone like that and share their stuff. I don’t see — it seems like it’s all your photos. I don’t see customer photos in your social media.

Ryan: Yeah. We do a little bit more of it on Instagram with user-generated content. But so much of it is about just taking photos from basically a weekend trip that we took and getting our friends outfitted in the product and showing it being used in a really real way.

Andrew: Okay. I’m looking at this guy who’s doing CrossFit and lifting weights and it looks like he’s really powering through a tough set there. That’s your guy?

Ryan: Yeah. We know the guys who own that CrossFit gym. So we said, “Hey, what if we brought over some product? I’m sure you guys have some members who would like to try this stuff out.” We just kind of put on a little sample show and let everyone wear everything, and we take photos while they do it.

Andrew: Okay. All right. Anything else about promoting and getting people to pay attention and buy?

Ryan: I think that really sums it up. Like I said, so much of our brand is based on that authentic experience and talking to guys in a way that I think they can relate to, that isn’t telling them how they should work out or why they should work out. It’s just kind of sharing there’s kind of this community of people that really prioritize living in a healthy lifestyle.

Andrew: I actually don’t see that on social media for you guys. It’s photos of people using your product with sometimes an inspirational saying next to it, sometimes you guys just saying what the product is. Where I see that story and the cult of Myles come together is on your blog. That’s where this guy John Bobby, is he someone on your team?

Ryan: He’s a writer for us.

Andrew: He’s got a post here, “How to Practice Meditation Anytime, Anywhere.” There, it’s not a direct sale of the product, but it’s, “Here’s our lifestyle. We meditate, we climb mountains, we journal using paper and pen, not a phone.” Through that, you also express like the connection to the brand.

Ryan: Yeah.

Andrew: Does that work for you? I can’t tell. I’m looking through SimilarWeb and I can’t tell that all the effort that goes into that actually leads to sales.

Ryan: A lot of that is stuff we also share to our email subscribers. We’ve found we have a lot of success, similar open rates and click-through rates with content like that than just putting a pair of shorts and a T-shirt in front of somebody. So, again, showing them that lifestyle and talking to them about those kinds of tips. They get a little more value out of our brand than just a great pair of shorts.

Andrew: How do you know what the brand stands for? Did you guys all sit together and write it down? Did you have anything like that?

Ryan: Yeah. We have a general brand philosophy, but I think it more comes from really the actual way that everyone on the team lives their lives. Like I said, almost everyone there bike commutes to work or takes a break during lunch and goes for a run, or we have like a weekly Thursday boot camp, where we bring in a trainer who comes in, in the mornings and puts us through the ringer. So it really does come from our own experiences and experiences of, like I said, all of our models are buddies of ours or friends of friends who have similar values.

Andrew: I see. So, when you hire, you make sure you get people who feel the same way you guys do, who work out the same way you guys do, and then that spirit comes out in your writing, but there’s no formal document. There’s no doc that says, “Here’s what we stand for as a brand. Here’s how we communicate that,” none of that.

Ryan: I’m sure there’s a Google doc bouncing around our shared drives somewhere where we’ve written it down, but it’s not something we have posted to the wall or anything like that at this point.

Andrew: All right. This jacket looks great.

Ryan: I’m really glad you like it.

Andrew: I am too. It would have been awkward if it didn’t fit right, right?

Ryan: It looks fantastic on you. Yeah.

Andrew: It’s got one pocket up here only, no side pockets?

Ryan: There’s a back pocket also.

Andrew: I could have sworn, actually, that I felt it.

Ryan: On the back right.

Andrew: Oh, I see. What am I putting in the back pocket?

Ryan: The idea there is for if you’re on a bike, especially, or running, you can throw your wallet back there or a couple credit cards and be on your way.

Andrew: I’m surprised that Noah would run with this. It seems too special, too much like a daily jacket to go work out with.

Ryan: Yeah. It’s that fabric. It’s highly, highly breathable even though it’s 100% waterproof.

Andrew: Could I just toss it in the laundry if I sweat it up? I’m a pretty intense runner.

Ryan: Yeah. Follow the care instructions, but yeah, it’s machine washable.

Andrew: Let’s see. I really like this. I want to wear this every day now.

Ryan: That’s what it’s made for.

Andrew: How does that look? It might be weighing it down a little bit.

Ryan: You can throw it in the back pocket too. It looks fantastic.

Andrew: Thank you to you for doing this interview. Thanks to Noah for being such a generous gift giver that I actually feel awkward. Do you feel awkward when someone gives you a gift or do you just say, “You know what? Thank you. I appreciate it.”

Ryan: I understand it. I think there’s a sense of reciprocity. But I think it’s great that he’s the kind of guy who would do that.

Andrew: Yeah. I do too. All right. The website is What’s the name of this jacket if anyone wants to see it?

Ryan: That is the Elements Jacket.

Andrew: Elements Jacket. Thanks so much for doing this. The two sponsors that you guys heard are Pipedrive, and I’d love for anyone who wants to copy Myles’ process for working with influencers to try Pipedrive. I think you’re going to see that it really will organize you and help you get the most out of your interactions with people. And if you want to hire a developer, designer, MBA and want the best of the best, go check out Thanks, Ryan. Thanks, everyone.

Ryan: Thanks, Andrew. Thanks for having me.

Andrew: You bet. Bye.

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