How Air Tailor Uses Conversational Commerce to Sell Through Text Messages

air tailor shopify masters

Conversational commerce is making the relationship between businesses and consumers more personal by bringing the customer experience into the context of SMS, WhatsApp, Facebook Messenger and other messaging apps.   

Joshua Brueckner is an early adopter of conversational commerce with his company Air Tailor, a provider of mail-in clothing alteration services that manages the entire customer experience through text message.  

In this episode, you'll learn:

  • Why they decided to rebrand their company over the next year.
  • What obstacles they’re overcoming as they’re rebranding and what they wish they did differently.
  • How they sell their services through text messages and what apps they use to do it.

Listen to Shopify Masters below…

Show notes:


Felix: "Today I'm joined by Joshua Brueckner from Air Tailor provides expert clothing alterations without the hassle of schlepping your clothes to the tailor. I love that tagline by the way. It was started in 2012 and based out of New York, New York. Welcome Joshua."

Joshua: "Hey. Thanks so much Felix. How you doing?"

Felix: "I'm doing great. Thanks for coming on. What is Air Tailor and how does it all work?"

Joshua: "Sure. Air Tailor is a startup and we alter clothing. We alter and we repair clothing. Basically people mail or we have a messenger go pick up peoples stuff, and then we alter it and then five business days later we send it back out and it's all done through text message."

Felix: "That's awesome. How did you I guess get started? Was your background in this technology field or what were you doing before Air Tailor?"

Joshua: "No. Technology isn't really my strong suit. I've always been a guy to try to figure things out, so I stitched the business together. I started off as a necktie alteration company. We were called Skinny Fat Ties or Skinny Fatties is how it looked, but we would take wide neckties and we would slim them down. We started that in 2012, and then at the beginning of 2016 we launched Air Tailor altering all types of clothing."

Felix: "Did you have a background in alterations? Obviously you were doing this already with neckties and now you've expanded to other things with I guess the new brand Air Tailor. What was your background? Did you already know how to do this kind of stuff before?"

Joshua: "No. Actually I was working in photography. I was representing photographers at a small agency in New York City, and unfortunately I got laid off and was doing the job hunt and I really needed interview clothing. I just looked in the back of my closet and didn't have anything and was like, "How can I make the stuff that I already own fit me better?" It was like a novelty idea to take neckties and do that. I started learning how to do that, and my friends were like, "Oh yeah, you should do this as a business or go and try to sell these," and I was like "That's kind of interesting." I did that and then that's how I started. I just learned on my own through necessity."

Felix: "That's cool that you basically took what you needed and did it yourself and then your friends obviously were very encouraging after they saw the work that you were doing, and they encouraged you to start a business with it. What was the next step? What did it mean to start a business now that you knew how to alter your own clothing or at least ties, and now you wanted to help others? What was the next step?"

Joshua: "I was taking the vintage ties that I like, went around and found that I had in the back of my closet and I was selling those at flea markets and on the side of the street, and then through doing that and interacting with people in real life, people were like, "Oh this is such a cool product, I would love if you would do this to my ties." That's what led me, and so I went home, I signed up for Shopify. I got everything going, and it was really cool. That's what led me to doing that."

Felix: "You needed to have these ties done because you're going for job interviews. You were then selling them in person, these ties that you had found and then altered them or were selling them, and people were then saying, "Wow, I really like ... " Did they know that you were altering these ties? How did they know that this was a thing that you were doing rather than just manufacturing these ties already altered?"

Joshua: "I used Instagram as a really awesome way to show before and after, and people just really loved that, and it took off because I was doing a lot of tailoring for bloggers for free, and it was really hard to do all this work for free, but it definitely paid off. That led me to bigger blogs and then that led to bigger press outlets. It really snowballed and took off."

Felix: "This is interesting because you didn't have any experience with alterations before. You did it for yourself. You never did it professionally I guess, and all of a sudden there's all this attention on you and people were talking about it, your friends and people that you were meeting in person, these bloggers that you were working with. At any point did you feel like, "Man, do I know what I'm doing," as you're going through this, because it seems like you obviously didn't. You learned this on your own and things seemed to take off for your very quickly early on? Did you ever have this fear of "Am I an impostor? Do I know what I'm actually doing" at any point?"

Joshua: "Yeah, definitely. When I first started, probably six months in, I ran a really, really big campaign with Gilt City New York, and it's like Groupon but for luxury goods, and people were ordering like crazy and it was so highly discounted and I was like, "Oh my gosh, I'm doing this by myself. How am I going to manage all of this? Am I even doing a good job? This is so new." Definitely there was so much doubt in the back of my mind."

Felix: "You were saying that I want to get to the Gilt City thing in a second, but you were saying how you were working with bloggers. Can you talk a little bit more about how were you working with them?"

Joshua: "Sure. Usually I would see a blog and I'm like, "Hey, this is pretty cool." Bloggers or Instagramers or whatever, usually Instagramers. I'm like, "Hey, this is pretty cool. I should find their email and let them know what I'm doing and see if I can do this for them in exchange for a quick post on their Instagram or on their blog." That would usually work out. Nowadays it feels like Instagram is really hard to market on, just because it's so saturated and people and brands throwing money at these bloggers. It's like a little bit harder I feel in how I've been trying to do it recently. Yeah, that really did work for smaller blogs definitely and for some bigger blogs."

Felix: "For these bloggers, you're still doing these alterations of their ties or what stage were you at at this point?"

Joshua: "I was doing ties, yeah. What's cool about doing that is that just like, I'll go on this further later, but it's neat because the bigger Instagramers look to the smaller Instagramers for inspiration and brands and things like that. I think that's what led to the escalation of getting on bigger accounts."

Felix: "I see. You were selling these ties that you were altering. People were saying you should offer this as a service, and at this point I think if other entrepreneurs are faced with this decision, I'd almost thing people would be split in half to decide, "You know, I was going to keep on producing these products or maybe even come up with my own line of ties," or they'll go the same route you took, which is to go at a service route rather than making the ties yourself and then bringing them to sell, they would go off and actually start doing these customizations and alterations for other peoples products. I guess talk us through that decision. Was it a hard decision to make between going the service route or continuing selling products."

Joshua: "It was not a hard decision. It was so early on that I decided to do the service as a service. It quickly took off. I think we had one article in Timeout New York that was like, "Hey, check out this vintage tie reseller that takes these wide vintage ties and slims them down," but after that and after we started gearing more as a service it really, really took off, and people were like totally into the idea of taking something that they already own and slimming it down because honestly, you save a ton of money. For the people that buy ties and wear them every single day to work and that spend a lot of money on ties. They go from $80 to $250 ties."

"We really found our niche with these kinds of people, and were able to help them save money."

Felix: "This Gilt City deal that you did, was it for alterations still or was it selling these already altered ties?"

Joshua: "It was the alteration service. It was really highly discounted. It was like I think at the time we charged like $34 per tie, which was a lot. We've since lowered our price, because we were so small we charged a premium fee. On Gilt City New York, it was $36 for two ties, and we had to pay for shipping and everything. It was just not a good deal, but it was a great way of exposure. When you're making very small amounts of money when you're first starting anything can just throw you off."

Felix: "Yeah, I want to walk through this timeline again real quick. You were doing these alterations for yourself or selling these alterations in face to face, and then you started offering this service, and what helped I guess kick it off? Was it that press mention in Timeout New York? What really helped you start that kind of a traction?"

Joshua: "It was definitely Gilt City New York. It was offering that because that led to Details Magazine, which has brought in tons of traffic. Details Magazine has recently closed down, I think at the beginning of this year, but that brought in tons of traffic for years. Press Backlinks were an awesome gradual traffic acquisition tool."

Felix: "Gilt City, it sounded like it was a ton of work and that's maybe didn't make much of a profit or maybe not much at all based on what I've heard from other people, and then from there though you were able to get a lot of press because I guess Details Magazine in this case, they saw the Gilt City deal? Was that how it worked?"

Joshua: "Yeah, exactly."

Felix: "When you were working with Details, what was involved? Did they just reach out to you and say, "Hey, I want to feature you?" How were you able to work with them to get your name out?"

Joshua: "They reached out, they were like, "Hey, we love what you're doing. We'd love to do an interview with you and put you in our tailoring section on our site." It lived there for a long time. I had a phone call with a reporter at Details, and he interviewed me. I think the next day we were on and that was awesome."

Felix: "Oh wow. This wasn't just a blog post that comes and goes. This was something that stayed on the website for a long time as not a blog post, but maybe a section on their website, and you guys were listed as an alteration resource?"

Joshua: "Exactly."

Felix: "That's very cool. Then I was thinking initially that it was a press mention, and then dies off, so I was wondering why you kept on getting so much traffic, but that's really key. Have you tried that strategy anywhere else to try to get into a magazine, either digitally or I guess in print, to place you as a go-to resource?"

Joshua: "Not exactly. I think they just tagged that article as a tailoring service nationwide that would help them with something, and because it was so unique it just lived there and we didn't really have any competition. It just lived there. The really cool thing about online press is that it sits as a backlink on search engines, and when people click that, Google ranks that as a top thing when people search for your service or your business or your products or whatever. That is a free way to get organic traffic that's relevant to you and be the go-to in that field."

Felix: "Just for anybody out there that maybe doesn't know a lot about SEO, whenever I guess authority sites like or any other big publication links to you, you obviously get a lot of the traffic right off the bat and maybe continually from people just clicking on the link from this site, but also Google recognizes that whenever a site with a lot of authority links to you, it boosts your basically SEO profile, so whenever anyone searches for keywords that you're going after because you have backlinks from large publications or large websites or a high authority website, it boosts your ranking. I guess that's how it's really paid off for you, not just from the direct traffic but all of the SEO and organic traffic that you've gotten because of these backlinks."

Joshua: "Yeah, totally."

Felix: "Now that Details is closed down, I'm not sure if the site's even live anymore, I would check it out, but has that affected your traffic once they closed down the website?"

Joshua: "Yeah, definitely. It actually has really affected the traffic. We've just been working really hard to get traffic in other ways."

Felix: "Yeah, I guess that does validate the really big benefit of having these backlinks from big publications, but then also on the other side of it, obviously it's paid off. You guys have been around since 2012, so obviously this has been beneficial for you for many years now, which I think is the most you can really hope for when it comes to SEO to get this kind of sustainable traffic for one, two, three years, but the problem with going after these backlinks is if you have all your eggs in one basket, then if that's taken away then it's taken away. The idea is to try to find as many high authority websites and large websites to get as backlinks as possible so you don't have to run into an issue where everything's just tied to one website."

"Cool. Let's talk about once you started, I always thought it was called Skinny Fatties too, I didn't realize that. I'm sure a lot of people made that mistake. Let's start there because I know that you've re-branded and it's now, but I want to talk about the very early days., you got these mentions in big publications, drove a lot of traffic. How were you able to keep that going? Was it all reliant on the press mentions or did you have other marketing strategies to get your first hundred customers, thousand customers on"

Joshua: "I really relied on press to get the word out. I'm trying to think back to what I did. Yeah, I relied on press. I didn't have a budget for this stuff. I started while I was on unemployment. I had no money. Press and then also word of mouth. When a customer placed an order and they were happy, I asked them to tell their friends or family or whatever. It just came organically."

Felix: "That's usually the best. The word of mouth is when you get somebody to mention your brand or your product to their friends or family, there's no advertisement that you can do, paid advertising that can be more powerful than that because it's coming from somebody that they already trust, and that's the key factor in getting sales online is breaking through. Not breaking through, but getting that trust from your customer. I think word of mouth is definitely huge. You encourage people to talk about your brand to their friends and family; how did you encourage this word of mouth?"

Joshua: "Well first off I did a really good job on altering neckties, and I think that speaks for itself. Since we're the only people that do this, it's led to that. I also set up a referral program. It wasn't wildly successful in terms of people sharing it, but I think that that naturally let people know that we're looking for new customers."

Felix: "When you were starting out it was really easy to get your I guess brand spread and to encourage this word of mouth because you had the product already, and that's a really good point. That's really key to getting word of mouth is by having a product people actually want to talk about. One is to have a great product and two is to have a unique product because if you're just selling, I don't know, paper or something, no one's going to care to talk about that because it's not something new or unique that people can talk about. That doesn't mean that you need to have I guess an organically interesting product. You can always find different angles, different stories to make your product something that people want to talk about, but for you the product itself was already interesting and unique enough for people to talk about."

"When it came to actually being the first in the marketplace, did you find that there was a lot of competitors that are coming into the space because they saw your success or saw that you're doing something that wasn't being done before? Was that an issue?"

Joshua: "Definitely not. There was only one other competitor in that space, and they've been around for many years and we actually got a lot of their work from customers that weren't happy and was like, "Hey, can you fix my tie? It's messed up from this company that did it." Since they're so old school, they really weren't doing a great job with SEO or with marketing or anything online. They've got an offline shop."

Felix: "You think that these customers, they went to your competitor offline, in their store. They didn't get the great product experience and they went online to search for a company that can alter them and fix the issues, and that's how they came across you?"

Joshua: "Yeah. We're not a tech company; we're just online. I think that the new standard now is that you really have to have a pretty solid foundation online, and have a good online presence. I think any customer really looks for that first. If somebody makes a restaurant reservation, I'm always going online to look at a menu. If they didn't have a website, it'd just be much harder. I'm always looking online as a consumer, and I think that you really have to heighten your standards if you have a business."

Felix: "That makes sense. Even if you are predominantly selling offline or wholesale or in person, it's still valuable to have a strong presence online because that's the first impression anybody gets of you because they might hear about you, they might not even get to go to the store right way. They might go online first or do some research, look up some reviews. Even if you don't do a lot of sales online, it's still important to have it because that's like you're saying a first impression, and if you don't have anything online at all that's still an impression in itself by saying, hey, you're maybe not a legitimate business because you don't have much of a presence online."

"Cool. Let's talk a little bit about the actual I guess running of the business. Let's transition to Air Tailor then before we get there. Since 2012, Skinny Fat Ties, you're running it. 2016 was the launch of I guess a re-branding into Talk to us a little bit about I guess that decision to go from Skinny Fat Ties to"

Joshua: "Sure. Over the course of running Skinny Fat Ties, sales were growing every single year. It was incredible. It was probably growing by more than double every single year. Awesome. That was really great. That was great, but I also felt a little bit like pigeonholed in what we can offer. I started selling other things like cool Brooklyn goods that the man that I thought would shop for our tie service would love, and then I tried to sell ties that we made from scratch. I tried to sell tie clips, just little things that I thought would sell and I always experimented with selling something else."

"To be honest, nothing really worked out. It didn't sell very well. People weren't excited about it. I went to the drawing board about a year ago, so May of 2015 I was voicing my concern with my mentor, and he was like, "Well why don't you consider altering shirts and pants?" I was like, "That's really scary and I probably won't do that." Then I went home and I really thought about it, and I spent the whole weekend conceptualizing how that would work and how I could take what I've built with Skinny Fat Ties and that alteration service, and apply it towards an alteration service for all types of clothing. I knew one of the reasons that Skinny Fat Ties worked out was because really nobody was doing it. Nobody was doing it as conveniently as we were offering it by doing it online and everything, and it was just such a unique service and there was such a novelty aspect to it."

"I really had to find how Air Tailor would be able to compete with a local tailor and how we were offering a differentiating factor to what we would be doing. Yeah, I worked on how can we offer alterations without in person fittings? How can we be more convenient for people and tried to answer those questions and also what are our overarching goals? What do we want to stick to as we scale?"

Felix: "Lots of great things there I want to start with first about how you were doing really well selling one type of service or maybe someone out there that's listening, they're doing really well selling one type of product. This success has gone on for a few years now, and you start feeling even though you had all this growth, you said a hundred percent growth every year, double each year, but you still didn't I guess not necessarily weren't happy, but you felt like you could be doing more, you didn't want to be pigeonholed. I think this is an experience that a lot of people have when they start getting some success and they start thinking, "Okay, what should I be doing next?"

"You started thinking about selling more products, at least when you talk about it, it starts very complimentary. It sounds like things that you could upsell to your existing customers, but it didn't work out. I really want to talk about this because I think this is a situation a lot of store owners run into where they think about expanding their product catalog, but don't know where to go. In your case, you did expand your product catalog and it ended up not working out as well as you expected. Why don't you talk to us about why you thought that it did work and why it actually did not end up working when you added these seemingly complimentary products."

Joshua: "I think honestly it's two things. The first thing is that our demographic for Skinny Fat Ties was Wall Street guys that are between the ages of twenty-five and sixty years old that wear a tie every single day. They're Manhattan guys or very metropolitan kind of guys that are up to trend with what they want in their necktie. Obviously it's such a unique specific service, and they're very black and white analytical kind of guys. Skinny Fat Ties I tried to sell wooden tie clips and I tried to sell Brooklyn artisanal stuff or handmade cotton neckties with a cool print, because that's me and I just never felt passionate about selling anything other than something that was me."

Felix: "I see. I just wanted to jump in here real quick. You started this business because you created something that you personally wanted, and even though your main demographic that was buying from you, they weren't like you at all, you guys just tied together by ties. Now that you wanted to expand, you thought, "Okay, what else do I like because I want to continue to build a store, build a brand of things that I personally would buy," but it turned out that because you weren't the same demographic, you didn't have the same interests as your core customers, it ended up not working. Is that a fair I guess assessment?"

Joshua: "Yeah. I wasn't passionate about selling anything other than ... Look, I'm doing this full time, so I don't want to be selling these beautiful silk neckties that are made in London and they're like five inches wide or whatever. It's just not me. Whatever I'm doing, I want it to totally vibe with what I like because it's really hard to market something that you're really not into."

Felix: "That's a very good point. I was just going to ask that next because the type of customers that you had attracted were not necessarily like you, but again, you guys have a shared interest in ties, how did you have to I guess change your marketing? Was it just solely specific on I guess branding or marketing the ties itself? I guess my main question is how were you able to market and sell to these Wall Street guys that weren't like you even though you guys were both interested in ties? How were you able to change up your marketing even though it didn't necessarily represent who you were?"

Joshua: "I believe in design, and I really think that the design of a brand obviously really speaks to who the brand is. The brand has always been a little bit cool and edgy, and I think that the guys that we marketed to were into a brand that's on the cusp of trendy and edgy, but we weren't redesigning their ties; we're just doing this service. I didn't think people really cared about what our Brooklyn brand looked like. I think it was just the fact that we offered this service. You know what I mean? I think that they were like, "It's a cool looking brand. The brand looks tight. They're not doing anything other than what they're saying that they do," and I think Brooklyn has this essence of craftsmanship to it if you market it that way, and that's what we've always done, so I think people were really into that."

Felix: "You solved the problem that was so core or so needed that marketing didn't even matter. That's what it sounds like you're saying, that you had this whole brand and marketing that represented you, didn't necessarily represent your core customers, but they didn't care because they really needed this service."

Joshua: "Yeah, I could probably put GIFs of cotton candy being spun and bubblegum being blown, and people would be like, "Oh this is really great, this service is so great and helpful." I'm sure our branding didn't hurt that much, but it was one of those things where people were just like, "Oh this is a cool service." I think that speaks to the thing about business is that whatever you're selling or providing as a service, people have to want and there has to be a need for it and it has to be good."

Felix: "That makes a lot of sense. I'm looking at now and it seems like you not necessarily learned the lessons of Skinny Fat Ties, but it doesn't seem to be as similar to Skinny Fat Ties. It now seems to be much more I guess catered to your core demographic of the working professional man that needs, not necessarily super serious website, but definitely much more targeted at the people that go to work in an office. Is that true? Did you start changing the way that your brand looked to represent that demographic a little bit more?"

Joshua: "What's interesting is that Air Tailor's new demographic, and I'm still trying to figure out exactly who that person is and that's just part of the struggles of being a startup, and I guess the opportunity to learn, but is we haven't defined it yet. I guess my goal in starting this business was that I really wanted a brand that was slightly neutral that could speak, because we tailor for both men and women, and I really wanted this to look like anybody could use it. That's probably a bad thing that I'm trying to capture everybody."

"I did learn a lesson and I guess this time around I'm just keeping it open ended and making it very clean and giving a very simple look to what we do."

Felix: "Yeah, I can definitely see that. I want to take a step back. When you said that you were still thinking about what you should be selling next and didn't have that much success with the products that you liked but weren't I guess catered to your core customers, you said you talked to your mentor about what to do next and your mentor suggested that you start tailoring other things than ties. You said that that's very scary. Tell us a little bit about that. Why did you feel I guess scared by that thought of tailoring other things?"

Joshua: "It scared me because I had never really delved into that before. I helped some friends out with alterations for their shirts and pants, and I'd done some stuff for myself, but I was by no means a professional seamstress or tailor or anything like that. I had just really knew ties. That's why it scared me a lot."

Felix: "Did that mean that you had to hire help? How did you transition from just altering ties until now? I'm looking at your website, pants, dresses, adding buttons, boots, watches. You do a lot of new things now. How did you expand your company's skillset to include all these new things?"

Joshua: "I didn't start immediately. I didn't make a website and say, "Hey, we do this. We're taking orders." I started conceptualizing in May and worked on it and did two betas, did tons of testing with local tailors, and then eventually I hired a tailor. That's how is that. I just sought help from experts."

Felix: "I like that, that you took a methodical approach and I just want to get the timing right. This was May 2015?"

Joshua: "Yes."

Felix: "About a year ago, you decided to start doing this. How did you I guess offer this service? Were you just emailing your old customers? How did they know about this, I guess when you're beta testing, how did you bring in beta testers?"

Joshua: "I didn't reach out to my old customers because I really wanted to have a refined product that could match the service standards that we had set for Skinny Fat Ties. I didn't include them in any of the beta testing. Instead I had a landing page and I had someone post to Product Hunt, to Beta List. We were on some cool tech blogs. I just tried to get beta testers that really understood what beta testing was. For those of you out there who don't know, beta means when a business is in beta it means they're testing to perfect their service or product to early adopters, and usually people that sign up for beta are people that totally understand that you're testing and they're helping you refine the product before it's on the market."

Felix: "I like that approach where you almost distanced it from your brand at first until you could refine it because you didn't want a new project to taint the experience that your current customers already have with Skinny Fat Ties at that time. You said you worked local tailors. I think this is also another I guess situation now that entrepreneurs run into is that they have this fear, me too included, we have this fear of when is it going to be ready to unveil to my current customers or unveil to my friends and family? Because while you're doing this on the side, or not on the side, but while you're doing this undercover, you don't have to worry about any pubic embarrassment or anything like that, but then once you are coming out and say, "Hey, this is a new thing I'm releasing," then all attentions are on you."

"Now the pressure is on, and not only are you launching to friends and family, you're talking about launching this to all your existing customers as well. Talk to us about that. What kind of emotions were involved? Were you afraid to launch this at the time, even though you went through almost a full year of testing?"

Joshua: "Yeah, it was really scary because that's my income. I work full time doing Skinny Fat Ties, and I'm transitioning customers over to something entirely new. We all know that people don't spend a lot of time reading everything and understanding everything, so when people are ready to place their tie slimming order again, will they know the steps? Are they educated enough? Something that we didn't really mention is that Air Tailor is done completely by text message. How will this demographic of these Wall Street guys that are between twenty-five and sixty years old respond to this new technological approach to ordering something?"

"All of these questions filled in my mind, causing me major delays in releasing the final product."

Felix: "Let's talk about, I want to get to the SMS thing and text messaging in a second, but I want to talk about this other thing about re-branding. I feel like when someone launches a business, they go through this hesitation because they want to make sure they get their branding right from the beginning. They want to make sure they get the logo, the name, everything right from the beginning because supposedly you can't change it later because it's going to be a lot harder to change it later, so they want to get it right the first time. Obviously there are concerns with that."

"You've gotten to the point where you've had a lot of success already and now you're going to re-brand your entire company that's already successful. There's one thing to re-brand when you're not having success, but now you have skin in the game and you have something to lose when you re-brand. Talk to us about that process. How do you successfully transition from one brand to another and then also have all these new products that come with this new brand?"

Joshua: "We're still in transition mode. Right now there's two websites that are entirely different. still lives as a tie slimming service. If people find it through a search engine, they can land on that and they can get their tie slimmed just as they were before. I also have a separate Shopify account for Air Tailor. It's like transitioning. My current customers have been notified of Air Tailor and our changes and how they can still order the same tie slimming service just in a different way. They've pretty much adopted pretty well, but yeah, it's still switching over. It's not going to be hard switched over probably for another year at least because we've got so much presence online through press and word of mouth."

Felix: "That makes sense. What kind of obstacles have you had to run into because you're in the middle of this transition still? What kind of obstacles did you run into that maybe you didn't expect while going through this re-branding?"

Joshua: "I have to be completely honest and say that our sales really dropped off when I switched over Air Tailor. I thought we had a really cool transition that would notify people, but it's really recurring customers have not been recurring after, and that's really hard. Starting Air Tailor is essentially, when I started Air Tailor, I was like, "Oh this is great. It's a service expansion from Skinny Fat Ties to Air Tailor. In all reality, it's starting a second business. It's a totally different animal that eats different than the old animal that I raised. It's a totally different demographic. That's been a real struggle in getting people to use the new brand, but really what I've been focusing on is building traction with new people for this brand."

Felix: "Cool. One more question before we move onto this new brand. While you're going through this, and because you've been doing this transition from Skinny Fat Ties to Air Tailor for a bit now, are there any steps that you look back on that you wish you took to make this process a little bit easier?"

Joshua: "I would say that I would do more market research in terms of starting. Because right now it's like a catch all, like, "Oh anybody, please. We do alterations and repairs." If I were to start over, even though we did tons of testing and I interviewed people like crazy, I would love to have gotten some more statistics about the alteration industry and about who uses a tailor specifically. We're starting to look into that now, but I think that would really dictate how to market to people better in a more specific way."

Felix: "I see what you're saying. Cool. Let's move on to Air Tailor. This is actually, not a pretty common, but a timely topic that I've been hearing more and more about, and it was something that was mentioned on a podcast episode, maybe five or so back, with the CMO of Shopify where we talked a lot about conversational commerce. Maybe we'll start there. To you, what is conversational commerce?"

Joshua: "Sure. Conversational commerce to me is when you use conversation to buy something with a company, so you're talking to a company and this service is not through clicking a call to action that says, "Buy now," but instead being like, "Hey, I need to buy this." Then they send you a link to pay or they just charge your account. That's conversational commerce."

Felix: "One of the best ways I've heard this described is almost like a concierge service. This is not like you go into a store and you buy something off the shelf, and it's not so hands-on where you have to be in person and they create an entire custom A suit for you. It's somewhere in the middle where there's still hand holding involved. I guess for you this is all done through text message, is that correct?"

Joshua: "Yeah, exactly."

Felix: "This is actually a question I asked the CMO of Shopify, again, Craig Miller, about how scalable is this because one of the advantages of selling online and selling product specifically is that it's highly scalable. There is a lot of leverage you can have because you don't have to be present to do every sale. On the other end of the spectrum, imagine you're a car salesman, you got to be present right in their face throughout the entire sales process. Again, this falls somewhere in the middle, but it does add more of a service layer to it. I guess are you running into these challenges where you have trouble scaling? Tell us about what kind of time commitments are involved when you do conversational commerce?"

Joshua: "Sure. I do think conversational commerce is scalable. You can train bots through some heavy engineering to answer questions with customers in a way that gets the job done, and it's automatic and you don't have to be there 24/7 with a customer support team. That said, when we first started, we did a lot of testing in this area of responding to customers. If they were like, "I need a shirt tailored," and we'd be like, "Great." We have a trigger for that if somebody mentioned the word shirt, and then it would say, "Great, what service would you like done?" Whatever. We just ran into a lot of issues with doing a automated approach to that. That works for some businesses that sell a very specific product whereas alterations and repairs, it's a hands-on approach."

"We like to think that we're a tailor shop that you're just texting your tailor. We talk to people one on one via text message, and people can send us photos and we can evaluate and we can instruct them and if they have questions, we can answer them. I guess that answers that, but we really believe in doing it like a real person is texting you. I will say that we do have some things that are automated like shipping. We'll send you that your item has shipped or that we've received your item. Then we can also do things like canned responses where I can talk about the service that we use to send the text messages, but they offer a really cool canned response system where you can have something already queued up and fire it out."

Felix: "Your branding, Air Tailor, obviously needs something like this when it comes to customization. For other stores out there that maybe don't have a service or a product that requires as much customization as yours, do you see that there's still advantages to using SMS and conversational commerce in a store that just sells a product that doesn't require any personalization at all?"

Joshua: "Yeah, absolutely. There's a company called Magic, and these are new startups, and then another company called Operator, that basically you can order anything you want through conversation. Magic is through text message and Operator is through an app where you chat with somebody. I don't know the specifics of if it's automatic or if they're chatting with you in person. I think that's the beauty of it is you just don't know, but we're seeing more and more companies move over to using conversation to sell."

"Chris Messina, the inventor of the hashtag actually wrote an incredible blog post saying that 2016 is the year of conversational commerce. Because we're seeing companies like Facebook use Messenger. You can schedule an Uber within their Messenger. Whatsapp, I think Snapchat, Telegram, all of these things are emerging as more of a commerce approach through conversation."

Felix: "This is something that I talk about a lot, which is that if you want to beat the big competition out there, there's no better way than with customer service, and if you are able to either actually have a team of people answering these things or create a more personalized experience through these automated services or bots like you're saying, I think it's definitely one of the ways to separate you from the pack because people want to interact with or talk to salespeople, or talk to people that know about this. I think live chat was probably the first incarnation of this. If you go to a website and a live chat bubble pops up in the right hand corner asking you if you need any help, I've seen statistics and case studies all the time about how many times they're able to close a sale just by engaging in a conversion on the website."

"You're taking this outside of the website even and now you don't have to in a website to have a conversation. It's all through text messaging, which everybody has access to. If someone out there wants to get started and implements a conversational commerce or text messaging based I guess service to their store, to their brand, what's the first step? What company do you work with and what's involved?"

Joshua: "Sure. I work with a really incredible company called Sonar and their websiteis, but it's really cool. They actually have a Shopify app, but if it basically connects you with your customers and hooks into it and lets you really get in touch with your customers in a way that you really couldn't do before. It's all through SMS and they text and then they also have a way that you can chat with people through your Facebook page. It's pretty incredible what you can do, and what you can really accomplish through text message."

Felix: "Awesome. To close this out, I want to talk about the favorite resources that you use to help you run your business. Other than, again, is the one that you use, are there any other apps or tools that you use to help you run the business?"

Joshua: "Yeah. Air Tailor we're finding is that we really need to have a strategy for getting people. One of our big marketing strategies is having an awesome content marketing schedule. That's really important to engage with people online that naturally find us through Google because we talk about hemming pants or we talk about another service that we provide. We use a really cool app that's small and stupid, but we're finding a lot of success with called Related Posts, and it just basically at the bottom of a blog post shows you a couple other blog posts that you've written and will highlight that, and then people don't just drop off on that blog post, but they click another blog post and read a different topic that you've talked about."

Felix: "I like that. Is this for WordPress or for Shopify? Where do you find this related posts?"

Joshua: "That's a Shopify app, so you can just search for that."

Felix: "Okay, cool. I think that's important to keep your visitor engaged because a lot of times the statistics out there as well, the longer that they are on your site, the more likely they are to convert. The goal is always to pull them deeper into your universe, your brand's universe, so that they get more and more exposure to the things you're talking about, you're going to be top of mind when they need to buy or when they are ready to buy a product and yours is going to come top of mind. On top of that, Google also encourages this too, for SEO reasons. You don't want someone coming to your site, reading one thing really quickly and then leaving. Let's say they search for hemming pants, they come to your site, read something real quick and then bounce off of your page. That sends negative signals to Google."

"You can keep them clicking and going deeper into your site. Great things again for your organic search rankings. Other than related posts, any other apps that you use to run the business?"

Joshua: "Yeah. I really like Delighted. It's a net promoter score survey app that basically you can set how many days after a product ships from you to the customer, pretty much when they receive it. We send it six days after an order ships of fulfills and asks the customer how likely are you to recommend our service or product to a friend? It's really cool the feedback that you get. It ranks from one to ten and then the customer can leave a comment. Then you can offer a discount to a customer that says a two or you can reward a customer that gives you a ten with a discount or thank them."

"One really cool thing that we actually use that Shopify recently put as a feature on their site was custom invoices. When a customer wants their pants hemmed or a shirt taken in or a pair of shoes repaired, we have that programmed into our site and we can actually just go at it as a custom invoice, and then over text send the customer a link to pay. It makes it really, really easy to integrate with a conversational approach to e-commerce. Then the other thing that if you don't use Sonar or if you just want to make it easier to sell from your product catalog online would be an app that Shopify recently released called Shopkey."

"Basically if you've ever heard of an emoji keyboard on your iPhone or whatever, it basically shows your products as an image in your keyboard, and then whether you're commenting on an Instagram post or over Facebook or whatever, through your phone, you can click a picture of the product that's in your store, and it will send as a link, which I think is really cool and definitely makes things easier from both your and the customer's end when you're helping them save time and yourself. I like Shopkey from what I've read about it, but definitely look that up because it'll help you sell more."

Felix: "This definitely seems like the key to running conversational commerce at scale. I read the description here, I think it's one of those things you have to see in person, on your app, and it's not a Shopify app like in the app store. It's on the iTunes app store. It says here you send links for any product in your store, paste product images into any conversation, search your entire catalog right from your keyboard. Take a look at the screenshots, I think it really describes it well how you can use this if you want to get into conversational commerce. What's the story for the rest of this year? What do you have planned as you're going through this transition into Air Tailor? Any other goals that you want to hit this year?"

Joshua: "Yeah, two things. The first thing is that we're really focusing on partnerships. We are trying to work with e-commerce stores that can tell their customers about us. If a customer is shopping for a shirt online and then they receive the shirt in the mail and the shirt doesn't fit, and usually people return it because it doesn't fit, we want to just put our card in there or somehow get this customer to know that, hey, there's an alteration company that can help because they do the alterations without any in-person fittings and it's like online as well and matches the customer demographic of the company that bought originally or the customer that bought originally."

"That, we're really focusing on partnerships big and small. Then the other thing is we're just building traction. We're trying to get people to see how easy it is to use our service. It's pretty incredible that you can just go on and text with a company and have something altered."

Felix: "Good thing that you're on a podcast with a bunch of listeners that own stores. if they want to work with you on a partnership like this, what's the best way for them to reach out to you?"

Joshua: "Sure. You can send an email to and we would love to work with you. We're actually working with some pretty cool stores right now in Los Angeles and in New York that are both telling their customers in their stores and also just including a small card, and we can send these cards to any store in the U.S. Wherever you're sending in the U.S., include our card because we serve nationwide."

Felix: "I feel like we should have covered this this a little bit earlier, but I don't think it's an issue towards the end either, but we talk obviously about how Skinny Fat Ties worked, we introduced Air Tailor. Maybe you can talk us through this process real quick. Someone wants to get let's say a shirt tailored. They open up their phone and they send a message to, and I guess take it from here. They send a message to you and then what happens?"

Joshua: "Sure. Let's take a step back. The moment that you sign up for Air Tailor, we're going to shoot you a text saying, "Hey Felix, welcome to Air Tailor. Can I send you a welcome kit?" The welcome kit includes safety pins, collar stays, a measuring tape, a card from us and also packaging to mail us your first garment. Say if you need a pair of pants hemmed, you would just text Air Tailor and say, "Hey Air Tailor, I need a pair of pants hemmed," and then you'd put a safety pin where you would like the pants to be hemmed to on only one of the legs, and our tailor receives it, tailors it down, within five business days it's shipped back out to the customer."

"We send the customer a prepaid shipping label so that they mail it to us. Shipping is only $5 total, and that includes both ways. It really is a convenient option for people."

Felix: "Awesome. I think that's a great service. I'm going to have to take a look at it. I think I have a few things I need altered too. Thanks for coming on Joshua., A-I-R-T-A-I-L-O-R dot com is their website. Check it out. Be sure to reach out to Joshua if you want to work with him on a partnership. I think it's a great opportunity to work together. Again, thanks for you time Joshua. I learned a ton. I'm sure the audience also learned a ton, especially about conversational commerce. I think you're right that this is an opportunity for a lot of stores to really separate themselves from the pack. I'm really excited to see what stores come up with over the rest of this year. Thanks for your time Joshua."

Joshua: "Cool. Thanks so much Felix."

Felix: "Thanks for listening to Shopify Masters, the e-commerce marketing podcast for ambitious entrepreneurs. To start your store today, visit for a free fourteen day trial."

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shopify-author Felix Thea

About The Author

Felix Thea is the host of the Shopify Masters podcast, the ecommerce marketing podcast for ambitious entrepreneurs, and founder of where you can get actionable tips to grow your store’s traffic and sales.