top of page

The blueprint for building a slow fashion brand in a very saturated space, with AYR's Maggie Winter

Today I’m chatting with Maggie Winter, founder of AYR.

AYR stands for All Year Round. It is a slow fashion brand and Its mission is to create confidence through clothing. The brand designs seasonless, ageless, effortless apparel for everyday life. The company is a hybrid of legacy expertise and future-facing vision.

This episode is really cool because it has a bit of a twist into how it got started and where it is today.

Please note, this transcript has been copy pasted without the lovely touch of a human editor. Please expect some typos!

My name is Maggie Winter and I'm co founder and ceo of air air stands for all year round and we are digital clothing brand that launched in 2014 and we are slow fashion brand.

00:03:43Edit We believe in designs that last all year round and our mission is to create confidence through clothing. I love that and I so see how you do that on multiple levels, including through the beautiful people you use on your website as your models and max's grandma, Are you talking about granny? Yes, iconic. I am, I love her, she's a new york city legend. Um she's our favorite model to shoot and when we shoot her, it's often in her neighborhood in the West Village and when we go out and take her picture, people stop her on the street and they'll say, oh Catherine didn't see you at the gym yesterday or oh you're modeling again. You know, she really has, she has her neighbors in her community and nobody forgets granny, she makes such an impact. She's our ultimate influencer. She's an icon. She's got flair, I can feel it through the pictures. Okay, let's go back to 2014, I want to go back to the very beginning because your founder startup story is a little bit different to the usual found up story you were incubated within bonobos.

00:04:53Edit I think that's how you pronounce it, bonobos. It's like one of those words that I can't say properly, but I want to go back to that time. Like how did this brand start? Like let's start there. Sure. I think that, I mean no startups journey is a straight line. I don't think from, from all the stories I've heard on your podcast and from all the friends I've talked to, it's rarely a straight line from the garage, you know, start up to the great exit and our story is also unique. We kind of had a Benjamin button narrative. We started in a more mature place and then we went backwards and it had its advantages and it also had its very unique challenges. I was hired to launch a brand and I was an employee of a company. So I had the best of both worlds, I had support and I had resources And I wasn't personally on the hook for paying salaries or for paying for inventory and I got to focus on my two favorite parts of the business, which really our product and storytelling and it was an awesome opportunity and I was 29 when I started working on air and it was kind of that perfect moment of, I've gathered experience, I've worked for brilliant people and with brilliant people.

00:06:17Edit I've learned a lot, but I'm still young enough to take a risk and if it doesn't work out, I have options ahead of me and I was that perfect spot of naive enough and and equipped enough to go take a risk and It was awesome. It was a wonderful environment to learn. But that suddenly came to an end when we were told, Okay, the company is not going to fund this brand anymore. And I was given 90 days to finance and form a new company While running our business and it was really, I wish there had been cameras that would have made a great reality show. It had been like 90 day fiance for business and not all those marriages work out. And I can't say that our spin out process was seamless and without any mistakes, it was completely challenging. It was the hardest thing I've done, but we did it and the good and bad of of our origin story is that we were able to start with some scale and we were able to start with outside resources to if it had been just me or just me and you know, to other people or something like that.

00:07:32Edit And and that was wonderful for us in starting to gain traction and great gain credibility and to be able to focus on more mature opportunities than we would have if we were doing everything ourselves as one or two or three people for instance, we were able to pitch to vogue And we were able to meet with editors and we were able to get early pr support and I'm not sure if we had started from scratch and we had to finance it all ourselves from the beginning. I'm not sure that we would have been doing that in year one or in, you know, in our pre launch before we go on. I have a few questions that I want to ask around this period before we kind of like keep going down the story because I don't want to like get lost and then have to go back. So when you were an employee of this company and you're building this brand, what does that set up actually mean though? Like, did you have equity in this sub brand or was it more like, hey you're just a straight employee, Like building something within.

00:08:36Edit And then how did that shift? Like how does it work when you when they were like we're gonna cut the funding, but you're like, oh, can I actually like by this brand or like can I like have the I. P. Of this like what's that section of this part of the story? These are all excellent questions and ones I wish I had asked about 10 years ago. Um but they're great questions. Um So we were employees of bonobos and we had shares as employees in bonobos bonobos co founder and Ceo at the time. Andy Dunn is a really generous leader and he's a person who wants for everybody to benefit from the success of an outcome. And so he was somebody who um always wanted for his whole team to benefit in the event of an exit. We had bonobo stock. Air stock didn't exist because there wasn't a company. We were just a team within the company, the same as a marketing team or a merchandizing team or a planning team existed within the organization.

00:09:38Edit And when it was time to spin out I started making a list and I started asking myself all the questions that you just started to ask me what are all the component parts of this brand and of this business and what do we need in order to exist independently. And the list included everything from I. P. A website to office furniture. You know, literally going through what as we negotiated the separation of assets, what is ares what what belongs to the parent company and then where do we need to fill in? And one of the big challenges was that we had products on order and we had a team of a half dozen people and that meant we had salaries and purchase orders that we needed to pay for and that we didn't have a bank account. So we needed to create one, put a whole bunch of money on it. And I had at that point I had never made a pitch deck before. I had never met with investors.

00:10:38Edit I had no vocabulary. I had no network. And the one thing I had was a really deep desire to see this brand exist and a very strong sense of responsibility to be the custodian of its success. And I just kept going and probably met with 75 investors in order to get 12 yeses and that was enough to finance the product that we had on order. And from there I kept meeting people and um I met investors who were really good fit for us at the time who invested in air as a company and did our series a and that was a big turning point for us in 2016. So it was in our our second year as a brand and that was when the learnings really started wow that is so interesting and so crazy. Yeah.

00:11:40Edit I've never had someone on the show share a story that started in that same kind of way in the beginning and I'm still interested to understand like with bonobos just like one follow up question from here and then we can move on. Were they like happy to like give you the I. P. Or did they have to keep some equity in the business and be kind of like still a business partner. Well I think you and you don't have to answer. I'm just trying my luck. I think you hit the nail on the head when you said this is not common. We don't there, we don't see the template for this playbook often. And so like anything else in business when you're creating something new, it's a negotiation and there isn't a standard formula for this is exactly how this goes and we follow the playbook. We had to negotiate all of this. And yes, um bonobos did retain a minority stake for having incubated us and for having helped support us the first two years that we were in business and the rest was a combination of founder ownership and outside financing.

00:12:42Edit That's so cool. There were so many things I wish I knew when I started my business, smaller things like blocking off my calendar for focused work and bigger things like investing in tools that help automate the busywork from building out your website to building up your sales pipeline, hubspot suite of operations, sales and marketing tools, help automate and connect different parts of your business so you and your team can ditch the busy work and focus on creating the best customer experience possible. Plus with helpful educational content, a supportive community and access to hundreds of app integrations, hubspot, all in one platform is built to grow with, you learn how to grow better by connecting your people, your customers and your business at hubspot dot com. Okay, so as you know, you listen to the show, we love to understand the blueprint for those early days in getting this business kind of like out there on your own. So I know you've already like you've been two years in business in that time, I'm sure you've had a lot of success with getting PR and all that kind of thing, because you've been under the umbrella company, but what is it like when you're you get some, you know, well I guess you get this money in your bank account to fulfill the purchase orders, you are able to retain your stuff.

00:13:56Edit What happens next? What does that like? First year look like? Wow, the first year was probably still a huge adjustment in terms of what you envisioned it was that instagram versus reality thing of you have in your mind what this should look like, what a company should look like, what a young startup should look like and feel like, and then you have the reality of operating it and it took us a few years to really align the intention with the reality and one of the best resources we have is Michael Founder max comes from Pr max and I have been friends for over 20 years. We met in college and we talked max's granny is our best model are my favorite model to shoot and there's biggest influencer and max's background was in luxury pr fashion beauty. Pr and she had worked for huge global brands, She had worked for cool new york startups and she really is the reason that we were able to build an audience organically for about our first four years, we did not invest much in digital marketing and we did hardly any paid marketing really, when I look comparatively at other DTC brands at the same time, we were really focusing on organic because I think at the time my background was in merchandizing and I had I put too much focus, I think on product and the thing you have to remember for anybody starting a consumer business is that nobody knows about you, nobody cares, nobody wants what you're making start with zero, you don't start with a percentage of your friends, you don't start with a gmail contact list, you start with zero and it's easy when you have a vision for what the whole thing looks like, It's easy to want to start there and you've got to start with zero, it's less product than you think.

00:16:02Edit It's less units than you think. And at the beginning we probably focused a little bit too much on product and not enough on audience. And it's only because max is a pr superstar that we were able to start building that audience organically low cost, they became very engaged and this is a place where the challenge actually worked in our favor as an entrepreneur, you have to take every obstacle and turn it into an advantage. And so the fact that we didn't have a lot of cash to spend turned into one of our biggest differentiators I think, which is that when you don't have money to spend on models and photographers and retouching and big photo shoots, what do you do? You buy a film camera on Ebay and you shoot your co founders granny, and it turned out that that type of right was stickier than the really well produced, beautiful imagery of beautiful people that was flawless, it really looked great, but it also looks ubiquitous and when you're scrolling through a feed, it doesn't really, it looks like ads, it doesn't look like necessarily uh you know, real people behind it.

00:17:13Edit And that's a place where I think that being cash strapped actually became a huge advantage for us with max doing your pr and like the media side of things like, yes, you have this approach to your actual content itself, but from the pr perspective, obviously fashion is such a saturated space and you know, finding your message and how to differentiate yourself in those messages that are going out in press releases. I'm interested to understand like how she was establishing the brand at that time because a lot of people I know who listen to the show are building fashion businesses and want to understand, you know, how do you stand out from the crowd in such a saturated space max was wonderful about getting us opportunities to get in front of editors ourselves because a shirt on a hanger is a shirt on a hanger and especially our brand is really about understated essentials that aren't very trendy. It's not about a label and a logo.

00:18:15Edit It's really about just making like a perfect white oxford button down. That's just the right amount of oversized and that's super versatile. But it's not the thing that you're going to look at on a hanger and be like, I've never seen one of those before. What is it invented something new? You know, And so max really was able to give us opportunities where we can focus on building relationships with editors and influencers. And I think that is exactly what this generation of DTC brands can do at scale, whether it's an editor or a customer sitting on her, you know, at home on her phone. We really have this opportunity to have one or more connections with people and to have our personality show through to make a joke at air. We take our work very seriously, but we do not take ourselves seriously. We really, you know, it's getting dressed in the morning shouldn't be the most important thing you do. And the women that we speak to our very busy women of purpose and they've got stuff going on.

00:19:17Edit And so we try to imbue our brand with a real sense of humor and honesty and I think that comes across as we're able to meet people. Hopefully it comes across and you know, we don't have a big team and I write our emails and our catalogs and post our social, it really is a person on the other side, not even a team of people, it's just one, it's just me. And so max's approach really let us be ourselves. And I think that has been a big differentiator in a world where we're in an industry where big players control so much market share and have giant budgets and can produce so much content at such a high quality. How on earth do cut through? Well you find your little space and you be yourself. And she was able to create moments like that for us where we could meet with a person, have a connection. We hopped on a plane with an editor from vogue to go to a denim wash house in Kentucky and it was a crazy day.

00:20:19Edit We went down and back in one day and I remember having like margaritas at the airport with her and it was wonderful. It totally demystified something that can be quite intimidating. But the reason we had that introduction and that opportunity was because we had a founder who had built a career and build trust and her expertise paid us back there in a big way, right? And was that trip just side question before I continue all my questions because I have so many still um was that trip taking the vogue editor with you to the denim factory? Was that you inviting her to come with you and like check out your factory? Yes. And it wasn't. So so it was so funny. I remember I remember this was when we were still at our parent company but we still had a budget and it was a small one because we were a small part of the business and we couldn't afford direct flights for all of us to go. So our team took took four flights that day. We we stopped over on our way and and we were able to get her a direct flight.

00:21:25Edit And um and it was awesome to be. We worked with a wash master who does wash development and he's kind of like this scientist wizard, mad scientist artist character and he's spent his whole life dedicated to perfecting denim washes. And he would use like powdered sugar in a wash or he'd spray pam the cooking spray. And then he'd come up with a blueprint, your factory in L. A. And be able to replicate it. You know, he can show you the perfect standard and then you'd replicate that recipe as best you could probably using different methods and ingredients but the craft of making clothing is so um it requires so many people and so much skill and expertise we produced globally. And we worked with some of the best mills and factories in the world and will go anywhere in the world where you can make the best of that products, the best t shirt, the best pair of jeans, the best oxford button down and it was cool to be able to show one person that and she had the ability to tell the story in a bigger way and then we could use, she wrote about air as a gift from the denim gods and then you know, in business, you always want to take that that moment is amazing, but it passes and going back to the idea of all year round, it's what you do with that moment, all the other days that really matters.

00:22:55Edit And so we were able to take that awesome day and then turn it into a tagline for the brand um and it's something that to this day we still reference because it was such, it was exactly what you would want someone to say about your tiny brand that nobody has heard of before. That is so cool. It sounds like to me like in those early years, like to summarize like how you were building the brand, it was like, you know, focusing on having max building these are getting you these opportunities impressed, like very 1 to 1 relationships, meeting with influences and just like doing a one by one approach instead of a 12 millions approach kind of thing and just slowly chipping away to get the word out there and build organically from there, when we think about, you know, That period of time, I think we're talking 2016 still, if that was the meeting with the Vogue editor to like, you know, circa these few years, what have been the major milestones that have left you forward? Because I know you guys have had some incredible growth, you've been tripling over here, wait lists over there, millions and millions of dollars everywhere, like doing so much success.

00:24:06Edit How do you get from that early days to hear the biggest trends? There have been a few there here. Let me think about this one actually, okay, because your question is so beautifully worded, I want to come and clean. Oh my God, it was not. No, you you have to teach me all your ways. Okay, um that's a great question. And if I were to distill it to the biggest moments, um, one that was a huge pop for us. Also a max moment. Oprah wore our shirt that, okay, so we have a shirt called the Deep End and it had been in our line for a couple of years at this point and um, I will never forget it. I was in L. A. I was in the midst of fundraising for the company. We needed, um we needed more money in order to fund inventory growth for our business and I had just learned that an investor dropped out for $750,000 which was a lot of money for us at the time. We haven't raised a ton of money, I guess it's all relative, but this was a big part of the round that we were trying to do and I found out we're going to participate in the round and the same day, literally two hours later, Oprah posted on her instagram wearing our shirt.

00:25:26Edit Mhm. And it was just that really cool moment of the rollercoaster of entrepreneurship. Right, Right. Oh my goodness. Sometimes I just wish for a couple of boring weeks, just two or three in a row, just nice, boring flat line. Um but it's not like that and this was in 2019. Oprah wore a shirt and not only did she wear it, she wore it on the cover of her magazine and she has continued to wear it. She has worn it on zoom meetings, she's worn it on the Drew Barrymore show, She's wearing it on the landing page for Oprah's Book Club. It really is one of her favorite. And this year it was named one of her Oprah's favorite things and it truly is one of her favorite things. Oh my God, we had friends screenshot us from being amazing. But wait, wait, how does Oprah see your shirt? Oprah worked with? I think it was, she was working with her stylist came into our store. Um This was somebody max knew professionally and and she, her stylist chose the shirt and then Oprah chose it, you know, out of the options, I wish I had been there next to Oprah and I wish I could tell you her thought process or how it works.

00:26:34Edit But I wasn't pr isn't my world, so I'm telling you as best that I know this is how it happened. And so that then has turned into us again, being able to amplify one moment and over time show it many people and we've reposted her instagram post. We've now been able to talk about this being one of Oprah's favorite things and this shirt has become iconic to the brand. That is so freaking cool. Another moment that was like, wait, wait, let me just ask you one more quick question before the next moment, what's the impact of Oprah wearing the shirt? Like was there a direct correlation to sales or is it like a long tail thing where like, you can't really quantify like how much kind of it did, but like what was the impact besides the press impact? Which I imagine would be crazy. First it started as a spotlight and this one product got more attention and we were able to distort it and I'm not sure it's impossible to separate exactly what was the Oprah effect and what was that?

00:27:37Edit Then what you do with that? Because then we talked about it as much as you shouted about it. Look, mom, I made it, you know, Oprah's wearing our clothes. That was so cool. So it started as a spotlight And then it becomes a halo, It becomes an opportunity to draw new eyes to the brand to build brand awareness and then they'll go to the website and you want to show obviously your best styles first and the most. And so it became an incredibly lucky moment that transformed our business. But we were able to support it from a marketing and merchandizing perspective. Then we wanted to add new colors, those over, pick those new colors as her favorite things. And and we really were able to now this spring and summer we have dresses and tops and um little tanks and skirts that are coming out in the same fabric. And we're gonna give open more options to wear in Montana. Exactly. Some of those moments are totally out of your control, wow!

00:28:44Edit Okay. That's amazing. Yeah. Some of those moments are totally out of your control and some of them are in your control. And one of the transformative moments that was in our control was launching a catalog channel. That was something that We did in 2020 and we've really been able to build a brand new audience and to re engage our existing audience through our catalogs. What do you mean catalog channel? Oh, meaning that that is a way that we're acquiring new customers and we're able to a catalog you're sending out a catalog. Is that what we're talking about? Yes. Got it. I'm like that's tv. Where are we at here? Okay. Got it. Okay, catalog channel right? To like direct mail? Yes. And I don't think catalogs are unique. Obviously anybody with the mailboxes seeing that lots of brands are doing it the way we do it is a little bit different. It's not, you will see max's granny in it. You will see max in it. We shoot the catalogs ourselves very low fi we were just shooting one over the weekend in L.

00:29:46Edit A. And we'll just go three of us. We don't use a ton of photo equipment. We just have like a point and shoot handheld camera. We take snapshots, we play music, we have a great day, come back, right, a little vibe, coffee, make some dad jokes. But it and then upload it and send it out in the mail to you. So it's not really polished and it's not triple distilled, triple filtered through. You know, two teams. And it doesn't have the level of production that most of the other catalogs in your mailbox probably have. But in the spirit of leaning into the things that are challenges and making them work to your advantage. I think that that differentiates us. I love that. That's so cool. Gosh! And so that's obviously working for you and you started that in 2020. What are the kinds of initiatives that you're focusing on at the moment? What's like the recent stuff that's working? Oh my goodness. The recent stuff is new product, it is so exciting to be investing in creating new product, it's like the most fun part of the job and getting to work on perfecting new pieces for our audience Is probably my number one favorite thing to do.

00:31:05Edit And you know, now that we have done these Oprah and the catalogue, these have all contributed to a business that is up 800% over 2019. So we've grown it tremendously. That means we have that many more people to talk to and now we're in a different place than we were at the beginning when nobody knew nobody cared. And now we actually have an engaged, awesome audience of people that we can share new product with. So I'm dying for these like amazingly soft ribbed tanks that are made in peru of pima cotton there and they're mixed with spandex and it's just the most comfortable tank top and it's, I have one sample and I have worn it to death. Like I take it out of the hamper before washing because I can't, I just need to wear it one more time before I wash it that's coming soon and working on a perfect oversized slouchy blazer, Really comfortable, easy pieces.

00:32:05Edit Like if you were going away for a trip no matter where in the world if you're going to London or L. A. Or new york or Iowa, anywhere you're going, you'd, you'd pack a few comfy comfy pieces in a backpack and be ready to go. We're making those pieces. I literally, before we got on this call, I was showing my husband some of their clothes on your website and I was literally like, this is like what I want to travel in And I literally said that I was like, this is my perfect like airport outfit because it's like comfy, not tight but still very chic, very sophisticated and like it's a vibe. It's a real vibe. Soon. You're a marketing genius. That has actually been one of our big hooks actually like travel and leisure. What about the best travel jeans and then in the Wall Street? Um, yeah, Wall Street Journal had done an airport style piece and of course we haven't been then we took a little break from traveling and we were the biggest traveling we were doing was from like the kitchen to the pouch. But um, but they are now that we are traveling again. They are the best versatile comfy pieces and you can like roll off a red eye into a meeting and not have to um, not have to go change your outfit, put on a lippy, some earrings and you're good to go when you say you are up 800%.

00:33:22Edit Are you able to paint the picture of like where the business is doing, say from like 2016 when you started out on your own to like now, even if it's like a seven figure ballpark, eight figure ballpark, nine figure ballpark, Like where's the business today versus where it was? Then I'm doing some quick math. We're up, we're up 25 times where we were in 2016. Well, well, well, whoa, that's amazing challenges though, when you start something, even if you're growing 46%, year over year, those are terrific numbers. But if you're, when you're growing off of a small number, there's still quite small numbers. And those of us who have been employees at big companies are used to small growth maybe, but over really big numbers and you've, you've just worked at a bigger scale. And I think it's an easy thing when you're starting off to assume if that's your frame of reference, that that's where your brand will be in no time.

00:34:29Edit And that simply isn't the case for some people it is for us, it wasn't, we had to start with with a small number, We always grew and we always group of 50% or more, but when you're starting off a small number, you still feel like you're, when, when, when does that breakout happen? Um, and it takes an awful lot of time, really, 10 years to overnight success? That's what they say? That's right? That's exactly what it is. What is your Best piece of advice for entrepreneurs in the fashion industry coming into 2022 on a tactical practical level. Do not buy too much inventory. The three biggest places, any consumer business invest is usually it's usually inventory. Marketing in people and marketing spend, you can usually turn off pretty quickly. People spend is really painful to diminished means you're letting people go.

00:35:32Edit Um but inventory is impossible to get out of when you are booking inventory, you're impacting lives and livelihoods of people globally who are working at males or at factories to produce products that you've ordered. And so you're committed to um that cash and in a slow fashion business like ours, you're often buying product six months plus in advance. And the world can change as we know in six months. It can change in six days. So it's a risky place to put cash and there's nothing wrong with a wait list, There's nothing wrong with building demand and building anticipation and really focusing on community and engaging in conversation with your audience in the meantime. So I would say be very, very careful about how much inventory you purchase by less. Always test before you invest. That's my tactical practical advice.

00:36:33Edit My spiritual advice is that you can do anything, but you have to do it and you should go in with that mentality of it's going to start with you at some point, you're probably gonna do every job and that's the best way to learn and to assume that, oh, I'll hire a team, somebody else will do this that'll be, I want someone is unrealistic and it's best to go in with that understanding that it's going to be, it's gonna be you, you've got to figure it out yourself. Don't rely on someone else Outsourcing to someone else who you think is going to make everything work for you because nine times out of 10, it's not how it works. Yeah, the cavalry isn't coming. It's, you're going to have, yeah, you're gonna have to figure it out for yourself. And that is the trade off of being an entrepreneur versus being an employee and there are so many advantages to both positions. The trade off of support versus autonomy and really figuring out what your flow state is and where you can produce your best work and make the best contribution.

00:37:38Edit Something you've got to examine for yourself and be honest with yourself and and continue to reevaluate as you go because both are great positions to be in. Um, and it's really about finding the right flow state for yourself. Yeah, it's so true. I feel like I talk a lot about this on the show and on other people's podcasts. It's like, it's really important to self audit yourself to, to figure out like what your, you know what you actually enjoy doing in the day to day and like what, where you are actually thriving because of course there's all these things that it's made to sound glamorous and blah, blah, blah, blah, but like, you know, entrepreneurship is hard, you've got to really audit yourself to figure out what you love doing on a day to day basis and where you fit in the mix. And sometimes that is deeply painful to do because I have learned that it is next to impossible to learn, do report and teach at the same time and when you're starting a thing And for the next 10 years after that, you're often in situations for the first time that you're ill prepared for and you feel completely well equipped to handle, but you figure it out because you have to, and then the next time you have some, you know, experience to draw from.

00:38:59Edit But it's really hard. Sometimes I do feel um that feeling of getting tossed in the waves and when that happens, I call friends who are also entrepreneurs, who are founders. Um and it can be the loneliest place to be until you talk to somebody else who completely gets and it's like, oh, 100% been there, done that. So good to have those moments of kind of connection and compassion and that gets you through to the next tossed in the waves experience. And then other times it feels like floating or surfing, like it's really fun and it just depends, I think on not even the day, but the time of the day, it all changes very quickly. I hear you. It's ups and downs. It's ebbs and flows of water analogies. A lot of water analogies. I'm here for it. I I missed the water. I want more water in my life. Wait, it's elemental, elemental is air. Thanks for listening to this amazing episode. We are testing out something new here for the next while and we're splitting up each episode into two parts, the main interview part and then the six quick questions part to make them easier to listen to.

00:40:14Edit So that's part one done. Tune into part two to hear the six quick questions.



bottom of page