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What is clothing tech?

Michelle Wiles is the Head of Brand at Son of a Tailor, a DTC “clothing tech” company that delivers made-to-order men’s clothing at scale. Their garments are custom fits to provide the best wearing experience, and reduce waste in their production process. Michelle joined Son of a Tailor after starting her career at Proctor & Gamble, VaynerMedia, and MBA school. As Head of Brand, Michelle leads the charge of infusing brand ethos at all levels of the company.

When it comes to sustainable products, it can’t just be your selling point that you’re sustainable.

Michelle WilesHead of Brand, Son of a Tailor


Julia Balick (00:00):

Thanks for tuning in to this week’s episode of Building While Flying. Before we dive into the conversation with Michelle Wiles, head of brand at Son of a Taylor, we wanted to let you know that Michelle is kindly offering our listeners 10% off their Son of a Tailor order with the code BWF10. So after you listen to the episode, head to their website, and explore their collections and use the code BWF10 to get 10% off your purchase.

Katie Hankinson (00:30):

Hi, I’m Katie Hankinson and I’m Mickey cloud. Welcome to Building While Flying a Sasha Group Podcast, where we interview business leaders about how they tackle challenges, stay resilient and navigate ever changing skies. Welcome to building while flying. My guest today is Michelle Wiles, who is head of brand at son of a tailor, a direct to consumer men’s clothing company. That is re-engineering the supply chain for apparel by taking the made to order model and delivering it at scale. Son of a tailor describes itself as a clothing tech company, making custom fitted garments to deliver the best fit, but also to reduce waste and production. Welcome to the show, Michelle. Hi,

Michelle Wiles (01:19):

Katie. I’m happy to be here.

Katie Hankinson (01:21):

Great to have you. Um, well I’m excited to dive in on all things, son of a tailor, but before we do that, firstly, where in the world are you? Cause last time we spoke, you were in like all sorts of exciting parts of the world and living in a classic nomadic lifestyle,

Michelle Wiles (01:40):

Which has gotten at least a little bit more acceptable these days. But yeah, so I live in London and I actually just got back to my apartment about 25 minutes ago. Uh, but semi Taylor’s headquartered in Copenhagen, which I’ve slowly learned is actually the kind of, I’d say probably headquarters of sustainable fashion in general. There’s a lot of really cool companies doing really innovative things in the fashion space there. Uh, but I’m also American and I actually used to work as part of VaynerMedia back in the day in the New York office.

Katie Hankinson (02:08):

Uh, yeah, I know I had a little Vanna shout out that it’s always good to have members of our extended alumni, uh, joining us on the show for sure. Well, I’m very envious. I think kryptonite is one of the most awesome cities. So I don’t know of course my hometown.

Michelle Wiles (02:23):

Yeah, fair enough. And it’s not a bad place to have to go for work. So

Katie Hankinson (02:27):

Before we dive in on son of a tailor, talk a bit about your background. We obviously know a little bit of it with the Vienna element, but what is the journey and experience that brought you to the role and company that you were at today?

Michelle Wiles (02:39):

Yeah. Um, gosh, I feel like I’ve done a lot of different things, but they’re kind of all over the marketing space. Um, and I’ve always loved brands. Is it actually started at Procter and gamble right out of college, worked there for almost four years, kind of doing very classic brand management. And I was working with all these agencies and I was like, man, I feel like agencies are having way more fun than I am. And I wanted to be part of that creative energy. And so I worked at a couple of agencies, including VaynerMedia, which is actually, I think one of my favorite jobs I’ve ever had the entrepreneurial energy as part of the agency was just so much fun to be a part of. We got to work with a lot of really cool clients and build really fun campaigns. Uh, but I’ve kinda always had aspirations to kind of build a full brand and pardon me, I was thinking, you know, I there’s so many brands I love, but it’s often not just because the ad it’s because of the advertising and the packaging and the mission and every single part of that brand.

Michelle Wiles (03:35):

And I want it to be kind of owning that fully. And so I went to business school to kind of getting the full experience of kind of how to run a company, actually founded a different sustainable brand during my MBA, and then ended up joining son of a tailor, just kind of figuring out how do we take this really cool new model for fashion and kind of take it global and build a brand kind of ideally on the same level as you know, a Patagonia. Oh,

Katie Hankinson (03:58):

Fantastic. Well, I love the aspiration. So let’s talk a bit about that. So son of a tailor is definitely part of this kind of growing traunch of fashion brands that are placing a really big, important emphasis on environmental consciousness and putting that right at the core of what they do. Talk a bit about what sits at the core of the son of a tailor brand. Like what drives you as a company.

Michelle Wiles (04:20):

That’s what I find so cool about Sonoma Taylor is that it’s completely unique on the market, you know, fashion, first of all, fashion. So defined industry, it’s one of the most dynamic and creative on the planet, but kind of, and as more news comes out, even, especially from the CDC report a few weeks ago regarding the environment, you know, fashion is a huge contributor to waste. And a lot of what you see in terms of what companies are doing, they’re waking up to this, but they’re very much focused on surface level changes. You know, we did a little bit of fabric change here, or we’re going to recycle some fabric in store, but in terms of what you can actually do with recycling fabric, it’s actually very minimal in terms of environmental impact. And with son of a tailor, they’re actually applying this engineer’s mindset to fashion.

Michelle Wiles (05:06):

And instead of focusing kind of on all the glamorous kind of sexy part of fashion, it’s everything before the product even gets to you. So it’s looking at every step of the supply chain, how are you optimizing it, getting rid of waste and doing that, but also saying, can you remove waste from the entire process, but also make a better product at the same time? And so that’s where this idea of made to order. You mentioned, came through everything we make is one by one. And what that means is that perfect fit. We have this really cool algorithm. So instead of, you know, buying a t-shirt that fits here and not there I’ve run out interviewed, I’d say like, I think close to 50 guys about that shirt. And I feel like with women, you know, we’re very discerning about SLOs. I didn’t know how big of an issue this was.

Michelle Wiles (05:54):

Every single guy has spoken to a steady, no, I can’t find something that fits because my body is unique, right? Everyone’s body is unique, but then we’re expected to fit into mass sizes. And so you just have to put in your height, weight, age, and shoe size, and you can get something that fits you perfectly. But that also means we don’t produce anything until it’s sold. So the typical model is, you know, produce a ton of stuff, hope that itself, if it doesn’t sell, we mark it down. The industry has gotten in trouble for burning clothes, right?

Katie Hankinson (06:26):

Huge amounts of waste piling up. So distressing.

Michelle Wiles (06:30):

And you think about that. And so the idea of, we know we had to burn clothes to make room for this next batch of inventory model depends on selling trends and selling more. And then, you know, using cheaper fabrics that have plastic in them and it makes you stop and say, wait a second, like, why is this industry the way it is? And once you start waking up to that, you start saying, you know, can there be a different way where we’re not just producing obscene amounts of extra inventory? We’re not flying around a shirt from China to Bangladesh, you know, so a button here and do this there because cheaper, but then the environmental cost of the carbon emissions to send it their way, outstrips any financial savings. Right. And so the hard thing is when it comes to fashion, there isn’t one kind of thing, oh, if you change this, it’s sustainable, you kind of have to change every part of the supply chain,

Katie Hankinson (07:22):

All the different leavers that you’re seeking to pull throughout the whole thing. Right.

Michelle Wiles (07:26):

Yeah. Which makes it super difficult from a marketing perspective, because not like we can be like, oh, we’re the brand for, you know, organic fabric. And then suddenly it’s like, oh, that makes sense. We’re trying to kind of fix every little part. And so that’s where we’re really leaning into this idea of re-engineering because we’re kind of applying that mindset. We actually applied a lean manufacturing process, the same one that Toyota uses to fashion to eliminate waste.

Katie Hankinson (07:51):

I love that. I, I think it’s why it’s smart to be thinking about engineering as the kind of overarching idea that encapsulates the brand because it is it’s about a mindset and a role that you’re playing in the industry, not just about a static product features. So I think that was kind of interesting too, like the engineers of the fashion business versus a company that to use organic cotton. And of course there’s an algorithm, there’s always an algorithm, which is a, you can’t go down the road with a direct consumer company. Yes. You have some kind of algorithm, but it was so interesting

Michelle Wiles (08:27):

That algorithm you like.

Katie Hankinson (08:28):

Yeah. I’m kind of fascinated though that with, with all those people who think I’m so unique, my body’s unique, but actually all you need is height, weight, age, and shoe size, and you’re getting accurate results.

Michelle Wiles (08:41):

Yeah. We get a lot of questions. Like why do you need shoe size? And um, so your shoe size or your foot length is actually the same. Like this is like your forearm

Katie Hankinson (08:51):

Of course. Oh, which actually that’s a total old wives tale. Everyone knows. Yeah. Unlike your arm span is the same as your height or something like that. I don’t know. Maybe that makes you in a record time.

Michelle Wiles (09:02):

Oh gosh, there’s that picture? And I’m gonna, I feel silly because I should’ve know what it’s called, but you know, that one that, uh, Shakespeare has Got the DaVinci one silly, but yeah,

Katie Hankinson (09:15):

Exactly. Yeah. So as a little segue out of this, what what’s the name come from? Is that an, is that a literal descriptor? Like, is there a story behind the brand or is it the son of a tailor in a more metaphorical way?

Michelle Wiles (09:32):

Yeah, I would say it’s the latter. Um, but it’s super cool. I mean, the idea is really about taking this industry into the future. And so I think about it that way, it’s singing this, you know, industry, Taylor’s very much reminiscent of fashion, but talking about the signup and really how are we creating this future of fashion? I think one of the hard things, especially when it comes to marketing and sustainability is that there’s a lot of negativity and a lot of, you know, we’ve got all these problems, you did this anti consumption, and I think what’s really cool about some of the Taylor and part of the name is that it’s very, it’s got a little bit of optimism about this new generation and that’s somewhere else you want to go with the brand is that it’s not about kind of criticizing, what’s been done, but saying here’s the situation. What are the things we can do to kind of build a future for the next generation,

Katie Hankinson (10:28):

That there is a little Baton pass to sort of take ownership of an industry, which is really nice. And it’s also, it got a nice colloquial feel to it.

Michelle Wiles (10:39):

Um, yeah, exactly.

Katie Hankinson (10:40):

When we last spoke, you said to me, it’s a good time to being brand, to be in brand. So look a bit about this, obviously as a, as a kind of the brand lead at this company, but also as you think about what brand means, but today’s direct to consumer and kind of newly purpose-driven businesses,

Michelle Wiles (10:59):

You know, it’s so funny. I just got off the phone with, uh, the recruiter who actually connected me to this role. And she called because she was saying that she’s trying, she’s recently gotten a lot more requests to hire brand roles. And, you know, a few years ago it had all been about digital and VP of growth and suddenly everyone’s moved to brand. And I had had this hunch about that. Um, I think, you know, these days you look at marketing has been very much performance driven,

Katie Hankinson (11:32):

Um, especially in the direct consumer e-commerce space.

Michelle Wiles (11:35):

Yeah. And it’s, there’s been a pretty simple formula, you know, open a Shopify store, put out some Facebook ads, redesign a category that didn’t look very good, uh, and suddenly you’re printing money, but I mean these days, the amount of simply even pet food brands is crazy. And so to differentiate yourself, you really need to have more of a purpose and something that resonates with consumers beyond a nice pastel logo. There’s a really excellent article about kind of the thing it’s like your bland new world of consumer brands. Um, and it kind of calls out the like Blanding and Bloomberg and it’s excellent. Um, and I think that’s kind of given birth to this new demand for how do we differentiate ourselves and get to what do we really stand for?

Katie Hankinson (12:28):

Yeah. And so when you think about that, you know, it’s very clear that the company is really built around kind of ethical, sustainable fashion. Um, and that when you come to a sort of central brand story is at the kind of core of it. But how else are you thinking about infusing that Brynn Brandy flows through the company at the beginning of this conversation, you were saying, you know, one of the things that fascinated you was was how brand can be infused into things like the product into the, how you treat the consumer, et cetera, et cetera. So what principles are driving that and how are you thinking about that? The son of a tomato.

Michelle Wiles (13:02):

So, and I think it starts with the company at large. So I spent the first few weeks at Sonoma Taylor interviewing every single employee. And it was funny how many people said, you know, I didn’t want to work in the fashion industry, but I came to son of a tailor because it’s different. And that was where we really got this brand principle of optimism because I noticed this level of optimism among almost every single person I spoke to. But when it comes to infusing that, I think it’s a matter of, kind of mapping out all of your touch points beyond kind of your paid advertising. So looking at how are we thinking about our packaging? What are we doing really? You know, we’re a supply chain company, but I think supply chain in any company these days is actually going to be spending that should partner more with brands because consumers are going to be asking, oh, you say you’re sustainable, but you know, how are you shipping your products? How much are you, you know, really costing the world in terms of carbon, because if those things don’t align, it doesn’t make a lot of sense.

Katie Hankinson (14:02):

And then in this world of transparency, you’re expected to be able to speak to that on the website versus being buried somewhere in a back office.

Michelle Wiles (14:11):

Exactly. And consumers are going to look for that. And so making that content readily available, but also in adjustable way is also very much a challenge.

Katie Hankinson (14:21):

Yeah, I can imagine. And there any adder it’s, because I remember when you were telling me a little bit about even just how you build a kind of feeling of brand within the community. Like it’s something like when, when you store your measurements, you it’s even the language that you’re using as a brand kind of gives it a little bit more of that custom feeling.

Michelle Wiles (14:41):

Yeah. And I’m actually even trying to get us, I’ve banned the word measurement for us internally, just because, you know, we don’t actually require measurements that require a measuring tape. It’s very much, you put in your height, weight, age, and shoe size. These are things you already know. Right. And so I think you’re totally right. How do you change your language? It’s very much kind of your operating system for your company and your brand.

Katie Hankinson (15:05):

Oh, that was it. You, you said that you, you don’t just create a side, you name it once it’s in the system. So you can be like, you can sort of play with almost personalizing the experience as someone who’s coming back.

Michelle Wiles (15:17):

Absolutely. So if you order from son of a tailor, it’s not going to be, you know, size small, it’s going to be size Katie.

Katie Hankinson (15:23):

Yeah. Love that. I’m excited, Katie hopefully is going to be like exactly the same for my entire life and never get larger Katie past.

Michelle Wiles (15:34):

Yeah. It’s going to be perfect. One click, whatever you want in the future. Super easy.

Katie Hankinson (15:39):

So in the world of threat to consumer, you know, it’s commonly known that the real, the value comes from lifetime value of your customer. You know, the, the kind of one-off purchase is only going to get you so far. How are you finding, um, how are you driving loyalty and how it, how are you seeing that play out as you begin to grow some of the tailor

Michelle Wiles (16:00):

That’s actually been, I think one of the saving graces for the company, especially as, you know, Facebook costs, rise so much and that what you’re spending to acquire a customer can often outstrip what you’re really earning on that first purchase. Almost 50% of our customers return within one year. And what’s really cool is, you know, once you have size, Katie, you just had to do one click and rewrite built in. Um, we have very strong loyalty. We find almost all of our customers come in through the classic t-shirt. But after that, that’s when we can start to kind of teach them about different clothes, show them some of the different options we have in terms of sweaters we recently launched or button-down shirt. And then we just find, you know, going back to your other question about embedding brand kind of across the organization, so much of brand is about the customer experience. And if you can make that super easy, that’s a reason to return. And so this idea of kind of that one click reorder, especially for our customer, that’s typically, that’s kind of like 40 to 60 year old, 46 year old male,

Michelle Wiles (17:14):

The idea of going to a mall, trying on shirts, finally finding something that fits and then next year, trying to find it again. They’re like, oh, that was last year style. We’re out such a house.

Katie Hankinson (17:23):

Totally. I mean, the struggle is real. Like whether you’re a guy or a woman or anything in between, it’s the desire of needing to she have a really consistent look and then your fashion throws away all the things that you loved and you didn’t buy two of them at that original, original point in time. Yeah. That’s awesome. So it sounds like the brand is, has a really fantastic foundation. You’re doing a great job in terms of driving interest and loyalty. Um, really thinking about the brand that every one of those touch points, you mentioned that the, the, that use case of kind of people hating to go to a mall and shop around. And obviously that’s double and COVID times. So how has that impacted the brown? I feel like the econ side of things has sometimes been seen as actually a phenomenal opportunity. Um, but were there other challenges that came with that as you kind of navigated the, the last 12 to 18 months?

Michelle Wiles (18:25):

To be honest, I feel like the tailwinds COVID have provided, been quite positive for son of a tailor kind of on two ends. One is the switch to e-commerce really grew the company. We’re a hundred percent e-commerce as you can imagine with our algorithm is quite hard for us to offer kind of perfect fit in a physical store. So this actually drove a lot of new customers for us last year, and that was customers are now returning, making their second and third purchases, which is great for us. Um, but on the other side, I felt like especially during 2020, every other article was around supply chains and how much they were strained, but given how smoothly our supply chain runs and how the fact that we don’t actually invest in a ton of inventory that needs to sit around and wait to be sold. We actually didn’t have any of those problems.

Katie Hankinson (19:15):

Totally. You’re not struggling with the disastrous supply chain or waiting for things, things that are building up and stacking up. You’re still in that one by one scenario.

Michelle Wiles (19:25):

Yeah, absolutely. And that’s what I was definitely not easy to get to. I, um, you know, I was asking my boss, the founder about how that worked and he told me, you know, when he first went out with this idea of made to order at scale, he said, you know, producers would say, you know, what’s your minimum order quantity. And he would say one and they’d be like, no one. And they’d be like, sorry, this isn’t going to work. Um, and I know that was quite difficult of a shift to set up.

Katie Hankinson (19:54):

It’s so interesting though, because my head goes to kind of the classic marketing plays for this. Cause it’s a really fun model in some ways, because you can build a lot of storytelling content off the back of it. Like even that story in and of itself of like that, that exchange of like, what’s your minimum Moda one, you know, kind of like the mind boggling feeling of, of something that’s kind of provocative to that. And the other one that makes me with that popped into my head was this idea of actually promoting slightly less fast fashion. Like you’re not slow. Like obviously you wouldn’t necessarily want to say with slow fashion, like slow food, but like slightly less fast. Like it’s okay to wait a little bit longer for the thing that’s made is made for you. You know, we’ve all been trained to expect something tomorrow with Amazon prime, but actually, you know, if it’s staples your wardrobe, why do you need it in like 30 seconds flat? Why not wait for like a natural reasonable amount of time for it to be made?

Michelle Wiles (20:58):

Yeah. Especially if you’re getting something kind of over and above what you would normally be getting, but this was another conversation actually we were having was around how, when it comes to sustainable products, you know, it can’t just be your selling point is that you’re sustainable to consumers more sustainably minded these days. But you know, the reason I think one of the reasons that Tesla’s done so well is that it’s a sustainable electronic vehicle, but it’s also a very good, yeah. And so for us, it’s like we can offer perfect fit and zero waste at the same time. And I think that’s really this path to sustainable future. If you want people to realistically shift and not just get this group of people that is sustainably minded, you’ve got to pull them in with something that’s a better value proposition.

Katie Hankinson (21:46):

It also plays into the stat, which is a bit of a depressing stat about how many consumers talk the talk, but don’t necessarily walk that talk and I’ll have to dig it out. But we were looking at it. It was a little bit more in the realm of CPG and grocery, but I, I guarantee that it plays into other categories, but it’s something like, you know, some obscene number, like 40% of consumers, basically buying habits don’t necessarily reflect the, what they claim to be their sort of ethics of purchasing. Um, so they say they only buy, they only want to buy sustainable organic, but they’re actually buying the thing that’s on offer in the supermarket, for example. So offering a thing that is also a compelling benefit that checks their other boxes also plays against that human behavior kind of beginning to having to pick, you know, the zero sum game. Like I have to get this thing I want, or I do the right thing for the environment. Like put them both on the same side of the scale, which is what you guys are doing.

Michelle Wiles (22:50):

Yeah. Like it shouldn’t feel like you have to make that choice or a sacrifice to be sustainable. Right.

Katie Hankinson (22:57):

So what’s on the roadmap for you in son of a tailor what’s coming next.

Michelle Wiles (23:03):

Gosh, I mean, I’m super excited about kind of doing a rebrand for us, you know, as we’re talking about blending, I think some of the Taylor has such an awesome, very distinctive product, but, and this is kinda something we all agree on on our website. It’s very to the point, but I think it’s time that we can really bring a lot of our ethos out in terms of our design. And so we’ll be kind of unveiling a rebrand, um, later kind of this year, which I’m super excited about.

Michelle Wiles (23:32):

Um, and we’re also kind of getting a lot more bold. I think I’m really finding our voice with our language. It’s funny, you know, when I speak to the team, the things that we’re doing are so innovative in terms of every shift that do in fashion, but we’re very much like, oh, we don’t want to say anything unless we can back it up with like eight sources. And I think it’s time for us to be more bold and less polite in terms of how we’re talking about the industry, because now is the time to make those shifts. And it just does not make sense to keep producing so much waste.

Katie Hankinson (24:03):

Right. I think, you know, provocation is something that’s needed, not only to cut through the noise, but also to drive action. And if feel on the, on the side of the angels, on the right side of history, when it comes to taking the fashion industry forward, I might as well shouts about it.

Michelle Wiles (24:22):

And it’s also definitely just a bit more fun for us in the marketing as well.

Katie Hankinson (24:26):

I love it. Well, I should keep, keep an eye out for that with great enthusiasm. Right. I want to see more of the story. Actually. I was one of the things I noticed on the site is it’s beautifully expresses the concept of the brand. They want to know more about the founding team and the ethos and some of that like obsessive engineering, that kind of Audi level obsessed, again as obsessive engineer.

Michelle Wiles (24:47):

That’s such a good example. They’ve done a great job.

Katie Hankinson (24:51):

Um, I, well, I had one other question, just, I love the fact that you clearly do a great deal of customer research and you’re speaking, not only to internal stakeholders, but also to tons and tons of consumers and prospective consumers, what’s the most, what are some of the surprising things you’ve learned about some of these people that you’re digging into? What, what matters to them and where they are today?

Michelle Wiles (25:16):

Oh gosh. I mean, one of the things was honestly how much kind of finding fit was difficult for guys because I thought it was easy. Um, but you know, once you get them to open up finding out, I think yeah, how hard it is to find fit, but also how much, I think even much as we talk about the product, it’s really, I think the biggest value out of Senator Taylor’s the process and how much stress it just removes. And I think some of the greatest brands out there are service brands and think about a brand like an American express and, you know, even apple, it’s a product brand, but I think the value of apple is it just works. And I think with us, we really want to remove kind of the stress and the hassle from this person’s life and just have something that you don’t have to worry about, all the stuff, you know, it’s going to fit, you know, it’s going to be easy, you know, you don’t need a measuring tape. And so that’s been super interesting to learn about, but I mean, conducting consumer interviews is probably one of my favorite things to do. I think you get a lot of fun ideas during that phase.

Katie Hankinson (26:26):

Totally. So many good nuggets, like little anecdotes that just set there, certainly imagination going. And that, that insight about taking the stress out of it is just, it just rings so true, especially now. And especially in kind of, you know, in this, as people are starting to become a little bit more about like their own identity in terms of their look and what they want to build and less beholden to kind of outside, not everybody, but like, you know, as you think about your staples, um, I think you’ve got already nice lane to play in there that you’re carving out space out in.

Michelle Wiles (27:00):

Yeah, absolutely. Um, the other funny thing I feel like is a lot of doubt, um, but almost in a good way. So, uh, actually when I ordered even the cemetery with my father and I messaged him and I was like, so how did it go? And he’s like, I’m surprised at fit that I told you I was going to fit our Trustpilot reviews. The somebody wrote in all caps. I am sorry. I doubted son of a channel, just the funny. And it’s great because I guess people are willing to kind of take a chance and see if it’ll fit. Um, and even though we talk about the algorithm, there’s definitely a lot of hesitation on, is it really going to work? I’ll give it a try.

Katie Hankinson (27:37):

That’s awesome. Oh, how brilliant though, that in a world where you’re used to kind of setting your expectations, this is the one time where like you can just relax without having to be like, oh, I knew it, another shirt that doesn’t fit with my weird chest shape or whatever, my wonky shoulders. That’s awesome. I love it. Well, finally, our last building wealth lion question, um, when you are building wealth line, it is important to keep common depression. So when your back’s against the wall and you’re faced with a tough decision for the business or the brand, what’s your internal checklist or process that helps you get through it.

Michelle Wiles (28:21):

So thinking about this on the plane as like there’s two things, um, one is really about being able to separate the things you can control versus the thing you can’t. And there’s actually some advice that the founder of son of a tailor, uh, has given me a couple times and that, you know, it’s easy to get stressed about everything that’s happening when you’re, when it comes down to kind of building that plane. There’s certain things you can control. It makes a lot more sense to focus on that as opposed to getting frustrated with everybody, with everything else. Um, and so I’ve been focused on that and that’s really helped me prioritize and also focus on what we really can do with the brand because branding, you know, it’s something that you can be very strategic, but it’s also very creative and balancing those two elements definitely has, you know, there’s not an, a strict formula of everything’s going to go.

Michelle Wiles (29:09):

Right. Um, and I would say the other part is about finding a sense of humor when things go wrong. Um, there’s a lot of, you know, I love research around positive psychology, uh, and how teams come together. And I think Google has a lot of really excellent research around teams and what makes them tick. And a lot of this has to do with teams that, you know, feel comfortable being themselves and being able to laugh together. And, you know, we do kind of allow all the campaigns we’ve done, we’ve done post-mortems and those have been really helpful for us to identify what we’re going to do next time. But we also make sure to kind of have a laugh. And I feel like our team has a lot of fun together as well. And that’s really brought us close together. Uh, we’re working on this project that keeps getting delayed and someone on our team said, you know, it’s just like this Kanye album when it comes to can be great conventionally.

Katie Hankinson (30:12):

Oh my gosh, you’re going to have to have the album launch party once actually does come through. I think that’s so important to really fantastic, um, mantras or approaches, like focusing on what you can change or achieve. And I’m really keeping an eye on the positivity and the optimism of the brand and then humor and culture is super important. Something we think is super important at the Sasha group too. Well. It’s been such a pleasure speaking to you. I’m so excited to see a rebrand and also hopefully to make a purchase with lightweight agent shoe size for a dude in my life.

Michelle Wiles (30:53):

Yes. And I’ll tell you a secret, if you, um, go through the algorithm at the end of it, you can message customer service. You can just say if you like, they are searching for, oh,

Katie Hankinson (31:03):

I love that actually. Glad you said that. One of my little note question marks is cause you know, I, I want the algorithm and solve my into all my decision making problems too. That’s brilliant. Well, now that we’ve finished that thoroughly interesting interview, we’re getting ready to land, but before we do Mickey and I caught up on some of the themes and topics that stuck out

Mickey Cloud (31:28):

To us, yes, we liken this to the,

Mickey Cloud (31:30):

It was game show where we break down the key lessons we all can benefit from, including us here at the Sasha group here is the Sasha sidebar.

Mickey Cloud (31:44):

Katie, what a cool conversation with, uh, with Michelle, from some of the Taylor

Katie Hankinson (31:48):

International Michelle traveling between Copenhagen, London and New York, um, what a cool company. I just, I think that whole premise is so interesting and just well thought through and yeah, I’m super impressed with the whole, the whole narrative around it. Yeah.

Mickey Cloud (32:05):

I think what’s, to me what stood out was the fact that they’re there, it’s actually quite simple how they make a custom shirt, right? Like it’s your height, your weight, your age, and your shoe size and her crusade to kind of eliminate the word measurements from their vocabulary internally because those aren’t measurements and the way you think about tailored shirt measurements. Right. And I can tell you, like, this is a category I’ve dabbled in from a consumer experience perspective where I’ve, I’ve like been interested in, Ooh, the, the technology that allows a body scan to get the perfect fitting suit or the other, these other things. And it’s like, in some ways it’s over engineered, you know what I mean? Like in some ways it’s like you could have just gotten this information with my height, weight, age, and shoe size that might’ve been easier

Katie Hankinson (32:56):

Instead of climbing into the holographic imaging.

Mickey Cloud (33:00):

Right. So I don’t know. I just thought it was like, oh, that’s it. That seems really cool. And then, and then the, uh, the other part of just like the, you know, to truly, if they’re going to, if their ideas were going to disrupt the fashion industry because of the environmental impact and create a more sustainable manufacturing process design process, like they truly showed that they’re actually walking the walk with that because, you know, when the story of the founder asking for a minimum order of one, it was just so telling. Right. Because it was like, I’m sure a like that he got laughed out a lot of rooms. Right. Because it was like, well, you can’t order just one, like, you know, that’s the, that’s the baseline assumption. There’s a minimal quantity that you’ve got to order. I chose real. Like we’ve got to rethink this industry if we can’t produce just one. Yeah,

Katie Hankinson (33:50):

Totally. And, and also just like such a fun, like little vignette, you can sort of imagine like that exchange at some of them, even in like telling the brand story.

Mickey Cloud (34:00):

Right. Yeah. It’s, it’s, it is a huge proof point that they, that they are a care about sustainability, but then be like, it is w we are, re-engineering how this world works.

Katie Hankinson (34:13):

Yeah. And I actually loved as well. The compensation at the end, when Michelle was talking about how important it still is to build brand, you know, they have a really interesting product, a really interesting methodology, and they could have stopped with, you know, what’s been such a plethora of brands or like selling the clever new way of making or method or whatever, but they know that, you know, that that’s played out like performance marketing and just selling a product proof. The point alone is not going to carry them as far as they want it to. And so really taking a long look at brand and then fusing that right, the way through the organization, this idea of these kind of like really obsessive engineers were completely, we think in the category, but also with a sense of humor is, um, is a really nice angle to build on I think, and a huge strategic advantage for them.

Mickey Cloud (35:05):

Um, and, and when it just works, right? Like, and when just the shirt fits like that, man, you know, that matters

Katie Hankinson (35:12):

And to delight that moment of delight,

Mickey Cloud (35:15):

Right? So maybe that’s our question for the audience is like, is there a product you’ve recently had where it actually delivered on what it said it was going to be like, this was fit. This is a Katy fit

Katie Hankinson (35:28):

I’ll report back. When, when Dean gets his shot a couple of weeks, thanks for joining us for building wealth flying.

Katie Hankinson (35:37):

I hope you learned as much as we did. We’ll meet you right back here next time for another flight.

Mickey Cloud (35:46):

If you’d like to hear more about how business owners and brands are navigating these times, tune in to the next episode. And if you’re so kind, please rate and review us, plus we’d love feedback. So let us know what you think, what you’d like us to dig into next on building while flying, across brands, businesses, marketing, and more original

Katie Hankinson (36:00):

Music by Fulton street music group.

Welcome to building while flying!

This weekly podcast is brought to you by Sasha Group. We’re the consultancy meets agency arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding media and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Our pilots, Katie Hankinson and Mickey Cloud, will be talking to a diverse range of business leaders and founders. They’ll explore how these guests tackle various challenges while staying resilient and committed to growth. Through these real-life examples of strategies put into practice, we hope to inspire you to experiment and develop your own strategies as we all navigate these uncertain times together.

Michelle Wiles is the Head of Brand at Son of a Tailor

, a DTC “clothing tech” company that delivers made-to-order men’s clothing at scale. Their garments are custom fits to provide the best wearing experience, and reduce waste in their production process. Michelle joined Son of a Tailor after starting her career at Proctor & Gamble, VaynerMedia, and MBA school. As Head of Brand, Michelle leads the charge of infusing brand ethos at all levels of the company.

In this episode, Michelle and host Katie dive into sustainability in the fashion industry and maintaining a strong brand—and how both of those impact a brand’s marketing. Michelle describes how Son of a Tailor’s unique ordering system and algorithm allows them to keep production waste low and customer loyalty high. She stresses the importance of transparency in brand, especially when you’re trying to be sustainable: if you’re going to talk the talk, you’ve got to walk the walk. 

Tune in to the episode to hear more from Michelle about sustainability, fashion, ecommerce and supply chain challenges, the future of Son of a Tailor, and more!

Other in-flight topics:

  • Sustainability in the fashion industry
  • Son of a Tailor’s unique ordering system
  • Importance of a strong brand in marketing
  • Driving customer loyalty
  • Navigating ecommerce challenges
  • What’s next for Son of a Tailor
  • …and more!

Links | Connect with Michelle

New York, NY
Chattanooga, TN
Los Angeles, CA