The Unofficial Shopify Podcast

A Tennis Pro Turned Bag Entrepreneur

Episode Summary

w/ Jack Oswald, Cancha Bags

Episode Notes

YouTube: https://youtu.be/rM2dQwDZe5U

We talk with Jack Oswald, a former professional tennis player turned entrepreneur. Oswald speaks candidly about designing a better sports bag, leveraging customer feedback and in-person interactions to improve the product. He highlights the effectiveness of short story videos, quizzes, and personal customer interactions in driving sales. This episode is a must-listen for anyone looking to improve their product design, customer engagement, and sales strategy.

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Episode Transcription

The Unofficial Shopify Podcast
7/18/2023

Kurt Elster: Welcome back, my friends. You are listening to The Unofficial Shopify Podcast.

Sound Board: cash register ringing

Kurt Elster: Your go-to source for eCom recon on Shopify.

Ezra Firestone Sound Board Clip: Tech Nasty!

Kurt Elster: Oh, that was in the wrong spot. I’m your host, Kurt Elster.

Ezra Firestone Sound Board Clip: Tech Nasty!

Kurt Elster: And today we have a special guest, a former professional tennis player, but more importantly the founder of a company called Cancha, Cancha Bags. Get ready to be inspired as we dive into the journey of Jack Oswald and how he’s reshaping the world of sports and travel bags. All right, Jack, welcome. How you doing?

Jack Oswald: Amazing. Really amazing. Thanks for having me. I’ve been a long-time listener, so really great to be part of the conversation today.

Kurt Elster: So, did you listen before you started a store? What was the thing that made you start listening? Which came first, the podcast or your store?

Jack Oswald: Good question. I think around about the same time, honestly. I’d like to say my store came first, but I think honestly as I was starting to delve into entrepreneurship while I was still playing, I was really interested in hearing about other people’s stories and I listened to another podcast, one called How I Built This. You know it.

Kurt Elster: Oh, yeah. That’s a huge one.

Jack Oswald: Honestly, between that one and The Unofficial Shopify Podcast, I was just going back and forth between both of them. I was just finding it so incredibly exhilarating and just so much information in terms of getting started, and yeah, so it’s been several years now I’ve really enjoyed every episode.

Kurt Elster: Well, I appreciate it. Thank you so much. Hey, did you leave a review?

Jack Oswald: I have. I have indeed left a review. Yeah.

Kurt Elster: Oh, good. Thank you.

Jack Oswald: It’s under a pile of reviews probably now, but I did leave a review.

Kurt Elster: No, I appreciate it. No, that’s like… You live and die by those but they’re hard to get. I mean, think about how often you’ll leave a review for anything, and for podcasts it’s even lower, and then it’s fractured across different… I should not do schtick about podcast reviews right now. All right, so you sell bags. Bags are a really… It’s a popular category. I think on Shopify, apparel and fashion, huge, and then you dive within that, bags, whether they’re purpose based, gendered like a purse, or just a backpack, bags are a popular category. I can think of three clients who sell bags and are very successful at it. KNKG, Tactical Baby Gear, Recycled Firefighter. Why bags? Why did you get into selling bags?

Jack Oswald: Yeah. I think you’re right. Bags are a really popular category and I think it’s partly because they have a really personal aspect to them. I think regardless of their use case, whether it’s a handbag, whether it’s a backpack, whether it’s luggage, people are carrying their prized possessions in these things and they’re taking them to destinations, and I think there’s a really intrinsic personality to them that people really identify with. And especially when it’s linked to a specific niche that people are really… Maybe it’s the phase of their life with something like Tactical Baby Gear, and I think that’s what really drives people to it.

In my case, in terms of bags, it was similar, but I was actually from the customer aspect. I was originally looking for better bags for myself as an athlete, so I was traveling and trying to better carry all of my tennis equipment. And whether I was going to another tournament in another country, or whether I was just touring around a city after an event, or coming home, I needed my bag for different things. And so, I originally really just started with trying to find a better way to carry all of my gear for myself.

Kurt Elster: All right, so you were a professional athlete, right?

Jack Oswald: Yes. I never made it particularly high. I played on the sort of lower levels of the professional circuit. I spent my life… Well, my youth dedicating myself to that sport. I had a dream of playing alongside the likes of Roger Federer and Nadal and all those sort of well-known names, and playing on the grand stages, and went to Wimbledon umpteen times to see it when I was a kid. Yeah, so that was… Tennis was always my passion and my dream, and I ended up making to sort of the lower levels of professional circuit, and traveling, and got to see some amazing places from South America, or in Asia, or around Europe, and in the States, and so I really got amazing experiences out of it even though I never really made it my full-time living.

Kurt Elster: And so, while you had that experience, which has to be an incredible experience and speaks to perseverance, speaks to self-control to be able to operate at that level, what would you say… Were there any lessons from that career that live today? That you use athletic experience, career lessons that apply to running your business today?

Jack Oswald: Yeah. Definitely. I think going into Cancha, I didn’t have the business background, but tennis helped me a huge amount in terms of my experiences there as an athlete, and I think part of it was just that growth mindset, which I think so many entrepreneurs have. And it’s an acquired skill. I don’t believe that it’s something you’re born with or anything. I think it’s an acquired skill, understanding it and having that mindset to get that 1% better every day. And in tennis, to begin with especially, it’s one of those sports where you just… You play like crap to begin with. It’s terrible. You can’t keep a rally going. You can’t really make the most of the sport. It takes a lot of dedication just to get to a point where you can fully enjoy it.

And so, that part of it is kind of… Especially on the business side of things, when you’re starting a business and there’s little money coming in, you’re kind of scrapping to kind of promote the company and to market it, similar situation where you’re just trying to get the building blocks, and you kind of have to do that in sport, as well. And then as you go up the ranks, suddenly it’s very hard to see the 1% gains because it's just… You’ve got such a level where they’re very, very small gains you’re making every day. But you have to believe in that and having that growth mindset that you’re kind of building upon it every single day, even if it’s a tiny, tiny block.

I like to think of it like a pyramid, you know? I began to really enjoy the aspect of when I was on the tennis court, and training, and playing tournaments, just putting another block on that pyramid each day. And even if it was a stone that day, it was something. And I think that’s something that I inadvertently brought over to business, where I was suddenly in an insurmountable situation where I didn’t really have any experience and didn’t understand how to get where I wanted to go, but my dad always had a phrase for me because he actually started a business when I was young, and it brought us to the States, actually. I lived in America for quite a few years.

And I didn’t think about it at all when I was a kid. I didn’t think about the fact that he was an entrepreneur or anything. Didn’t mean anything to me. But he used to always say to me you can eat an elephant one toe at a time. And I, again, didn’t really think of it at all. And now I realize how important that is, is that these insurmountable goals are… It’s all about just taking one step forward. And that’s kind of something I took from tennis into entrepreneurship.

Kurt Elster: So, the bag you developed, this is specific to tennis players?

Jack Oswald: It certainly started that way. We’ve expanded quite a bit since then, but definitely started with tennis, and it started with tennis simply because that was an industry I knew. I knew it so well. I spent most of my waking days on a tennis court or traveling between one, so I knew what it was like traveling with tennis equipment. I knew that I could provide value there. And I knew how the tennis industry was quite antiquated in terms of still relying on wholesalers, retailers, antiquated type of marketing tactics, and so I knew that there was a lot of innovation that could happen there, both in the product and also the brand side of things.

But since then, we’ve kind of branched out a bit. Tennis is still a big part of our market, and we sell bags for tennis, but also for outdoors and adventure, which is quite a saturated market. I think we started there, we really struggled, but we still have some… We have products there. And then also paddle and pickleball in the U.S., which is just exploding. Paddle is the version in Europe, which is just a really big-

Kurt Elster: Tell me about it. Geez.

Jack Oswald: Yeah. Everyone’s into it.

Kurt Elster: All right, so you’ve got this experience as a professional athlete that is this childhood experience of seeing your father going through entrepreneurship… I said go through like it was an illness.

Jack Oswald: Sometimes it can be.

Kurt Elster: Wrong phrase. But all right, so you had a tennis player, this then contributes to your understanding of needs and preferences when designing bags because you had that very real, direct travel and play experience with it at the competitive level. But then on top of it, you also saw the opportunity for advancing the industry in terms of sales? Like they were very committed to that old school not direct model, it seems?

Jack Oswald: Yeah. And I think, obviously, even since 2020, when a lot of these brands had to make that shift, I think it’s still lagging behind it a little bit. But I think where I really saw the opportunity especially was originally when I started to design these bags, I was looking, designing it myself, and I didn’t know anything about textiles, didn’t know anything about product design. But I started to see a wider need for more people who are just trying to fit their favorite activities into their daily lifestyle. So, not necessarily full blown athletes, or someone who travels every single week, but people who are just trying to make sure they can carry their laptop and their tennis rackets. They want to go and play tennis before work in the morning, or if they want to go to the gym before work, or they want to take their tennis rackets when they go for a trip, whether it’s a holiday, whether it’s a work trip. Being able to kind of adapt for that.

So, I think that’s where I really saw a lot of the need there.

Kurt Elster: And so, a tennis racket, an unusual thing in terms of size and shape. Well, let’s go back. What year, when do you start this business?

Jack Oswald: Yeah, so I started designing the bags on a very meager level in 2018. That’s kind of when I decided I was gonna try and do this as a side project. We ended up… For about two years, I was designing the bags, and I was taking all the bags with me on tour, some of them breaking on me halfway through sometimes. Bits falling off. It was not a pretty picture, but I was trying… Probably went through about 50 or 100 prototypes. But during that period, I met some designers who had worked on some really interesting projects in the past, and I started to work with them, and I made really good friends with one in particular. He used to invite me to his workshop where he had all this incredible machinery for laser cutting fabrics, and bonding them, and making them waterproof, and all these things that I thought I’d have to go to Asia to see.

And I started working in his workshop, and we were working together, and in the end of 2019 I did a crowdfunding campaign which was moderately successful. But I actually learned way more from that than I did from the sales. I think we understood more about actually what people wanted, and actually starting to really refine that, and obviously then the pandemic hit, and we were set back a few months, 6, 8 months anyway, and I was able to really kind of delve deeper into how are we gonna target this product at the right person? How are we gonna make sure that we can really build value going forward? And that’s where the modular design came up, as well, allowing people to really personalize their bags with different accessories they can attach to their bag.

Kurt Elster: So, when you made those initial prototypes before you met this product designer, how were you doing it? Did you learn to sew? You said you went through what? 100 prototypes?

Jack Oswald: Yeah, very much of that was in his workshop, and then I used to go to trade shows. I went to… There’s a particular trade show in Europe that’s called ISPO, and it’s in Munich, and it’s an incredible trade show. It’s about 8 football fields, or soccer fields, sorry, in space and size, and so I went there about four or five times visiting different suppliers, for different buckles, zips, fabric, all that sort of stuff to try and find the right materials. And that’s where I learned a lot, and that’s where I was also put in touch with some designers who are able to start to prototype, and I started to prototype with them to kind of going into their workshop, and working with them, and kind of trying to really fast track things, but also try to fit it within my traveling tennis schedule, which was difficult.

Kurt Elster: Yeah. I would imagine that there’s a lot of demands on your time there. So, once you had a product you were satisfied with and you were using it personally, so you figured like, “Well, this will work,” then the move was crowdfunding campaign? You did Indiegogo?

Jack Oswald: We did do Indiegogo, yeah, and with very little budget whatsoever, and just trying to see where it started. And we kind of learned, like I said, we learned a lot from that campaign, and not necessarily in terms of sales, but a lot in terms of what customers were, how they’re perceiving it, and things like that, and whether we could really innovate the product. And that’s where I think I learned a lot, that really bringing the product to market as soon as possible is actually a really important thing to do if you can, even if it’s on a very small scale, because you learn so quickly from that.

And I’m glad that we did that and then were able to kind of rebound off that, and really launch much more strongly going forward than if we’d just kind of spent all of our money on producing it before we’d even got any feedback. So, although we did that throughout the design process, one thing is getting people to try something out and one thing is getting someone to buy it. And until you get that person in that situation, where they have to hand some money over for something, that’s when you really find out where the value lies, and where… if it’s actually meeting their expectations.

Kurt Elster: Well, what year was that campaign?

Jack Oswald: So, that was in 2019, so we were still really designing the bags, even… We designed one of our main products, which was part of the campaign, which is actually one of our… The original design behind it was actually a backpack that could adapt to being a tennis bag when you wanted, that could adapt to being a gym bag, adapt to be a travel bag. We kind of realized that this one-size-fits-all approach wasn’t what people were looking for. What they really wanted was something that they could really personalize to their lifestyle. Something that they could take a base product, like a tennis bag, but they could carry their laptops where they wanted to. They could carry their wet and dirty clothes, or their shoes in it if they wanted to. They could carry their tech travel gear.

But then they could do something else, as well. So, something where they could really personalize it is what we realized that’s where we needed to pursue our efforts.

Kurt Elster: And so, the original bag is an attempt at a one-size-fits-all bag. It’s on Indiegogo. It was $143, or 115 British pounds. We raised $5,400. That’s 21% of the goal.

Jack Oswald: Yeah, so this is where I say that I think that that’s why… You know, looking at that campaign, I didn’t… I was kind of going into it cold, trying to figure out how to market it. The fact that we even made that was pretty amazing because of how little I knew about trying to make this work. But yeah, it was originally a backpack that was kind of like a roll top. We really had this cool modular design that we designed where it attached different accessories onto the bag, but I’d made the mistake of understanding what the core product needed to be, and that’s where we kind of shifted really in terms of focusing on the tennis bag, which is very, very different now. We’ve gone through several updates to that since then.

But yeah, I think it was… At the time, wasn’t happy, but I think it was actually an amazing opportunity to improve the product and learn from that, and then really… It really helped us have a lot more success going forward.

Kurt Elster: Yeah. The original bag, it looks like this heavy duty technical waterproof fabric. It’s a roll top bag. And then it’s got MOLLE webbing, but like not in the tacticool way that we normally think of. It looks much more integrated into the bag. And they’ve got… I forgot what they call that, but it’s where you weld synthetic material to another… It’s like an electrostatic process.

Jack Oswald: RF welding.

Kurt Elster: RF welding. Thank you. Yeah, that, you see that and you’re like, “This is some good stuff.” And so, that bag looks good, and then when I see the final version on your site, and we gotta talk about your content at some point because it is phenomenal on this website. The aesthetic has not changed but then the bag becomes much more… Well, more traditional, but then still has the attachment points for its accessories, and then there’s a wider range of bags. Oh, these are add-on attachments, but then those are their own bags. Like this day bag is its own bag but then also an attachment?

Jack Oswald: Absolutely. Yeah, so this is where the content comes into play, because there’s a lot of education rewired for you to understand how everything works, and when you’ve got limited attention span online, it’s really important to get that across. But yeah, so our bags have different kind of accessories that attach onto them, so for example, we have our core products, like our racket bag, backpack, we have a paddle bag for pickleball as our core products, and then we have different accessories, like a day bag which attaches on. We have a wet/dry bag for your clothes and shoes inside. We have a larger version of our day bag, day bag XL, which fits different laptops and things like that inside, cables, and you can just wear them all independently.

So, if you wanted to take your rackets off when you get to work and just take your laptop bag in for work, you can do that. And vice versa. If you’re carrying both on a plane, you can attach them both together, put them up in the overhead locker, so that’s kind of the idea behind it. You can attach and detach depending on what you’re doing throughout the day.

Kurt Elster: What I love is those accessories are very much just as useful independently. I could buy the add-on bags and never buy that core bag. And it would still have the same or similar utility. I think that’s clever and important. Because then it feels less like an add-on purchase. So, when that Kickstarter happened, you’d spent a year, you’re like, “Look, I’m my core customer. I live this life. I played with this product. I used it in the field the way it was intended to be used. We put it on a crowdfunding campaign on Indiegogo. We had the pro content made.” And then you got to 21% of your goal. You either could have said, “Well, we tried our best and it didn’t work out, so let’s just quit here and not throw good money after bad.” Or you say, “Wow, 27 people were willing to buy that product and it still feels unfinished to me. Let’s keep going.”

What’s the difference between those two mindsets? How did you not go negative with this?

Jack Oswald: Yeah. I think, to be honest, you do hear a lot of stories about people that just go… Companies go viral with a product from day one.

Kurt Elster: It’s so rare. It’s like hitting the lotto.

Jack Oswald: Exactly. And I think sometimes there’s a misunderstanding of what it actually is like to get from… just even get started with these things. And actually, there’s a huge amount of pivots required, and most of the time it’s not a dead certain failure. It’s just a need for a pivot and to reassess how to get where you want to get to. And going back to my tennis days, they used to always tell me when I was competing, coaches and things, that every next tournament, every week is a new week. I mean, it doesn’t matter if you lost the first round last week, you’re in another tournament this week, so it really doesn’t matter what happened last week because you’re… and you gotta have that mindset, I think.

I think it’s the same way that you hear about a lot of… especially on this podcast, I’ve heard a few times where people have tried to just throw out a Facebook ad for an idea and see if it sticks, and you know, it can work sometimes because maybe you’re not gonna get hundreds of thousands of sales, but just getting a few sales here and there is just gold in terms of the insights it can bring you.

Kurt Elster: Oh, absolutely. Yeah. Getting it out there, getting the experience, getting it in front of people, or in their hands, so it sounds like after you got the product, you had that experience, now what’s the next step? You said, “We’re gonna redesign this thing?”

Jack Oswald: Well, it wasn’t necessarily the plan. I mean, we were going into January of 2020 kind of… I say we, it was mostly me, and speaking with our designer a bit, and I think we went into that thinking, “All right, what do we do?” We have to fulfill these orders, for one thing. So, we actually do need to make it on some sort of scale, so can we… If we don’t have the cash to produce it, or like 500, 1,000, 1,500 units, can we try and makeshift this in the U.K. in terms of maybe it’s not gonna work out economically, but can… We’ve actually got all the machinery and everything. Can we?

But then, of course, in January, February is obviously when things started to get a bit haywire in the world, and it actually meant that we didn’t… We weren’t able to even make these 20 or 50 bags, whatever it was. So, what we did is we went back to the drawing board because we had no other option. Everyone was in their homes. We were kind of twiddling our thumbs. And I thought, “Well, I know I can make this better. I think I rushed this. Let’s work on what people… Let’s go back to those customers. Let’s see what they liked, what they didn’t like. Let’s go back to what our core value proposition is and let’s try and prove this.” And actually, the core bag on that, like the backpack that you see on that Indiegogo campaign, it is available. It sells today. A different version of it, but we have it available.

Actually, it just needed to be repurposed in terms of maybe that wasn’t the right bag for tennis players. No, it was the right bag for somebody who just wanted a good backpack they could take traveling. So, that was kind of how we kind of got forced into doing it, I guess.

Kurt Elster: You know, it sounds like it was necessity, but at the same time you’re like, “This is the situation. This is the best outcome.” The way through was forward. You figured out, “All right, how do we take the next step? How do we keep going?” So, at what point do you move to selling directly with a Shopify store?

Jack Oswald: Yeah. I mean, like a lot of beginning entrepreneurs, I started on… I believe it was WooCommerce, and just started getting increasingly frustrated with…

Sound Board: Ewww!

Jack Oswald: … how much just to maintain it, how much input it required. You know, I always felt like you turn something on, it turns something else off. You change something, it affects something else. There’s just like… Everything’s so interconnected that you can’t… You’re just fearing touching anything for the whole thing just to fall down and collapse. So-

Kurt Elster: That’s what we… You know, before we discovered Shopify, we were doing WordPress. We were WordPress developers. And so, I empathize with that experience, and that is where we coined the term Jenga tower website. The Jenga tower website, careful what you remove or mess with because that whole thing is gonna come down.

Jack Oswald: Yeah. Perfect description. Perfect description of what it is. And I think… Who knows? Maybe it’s got a little bit better today. But I think there’s… The amazing thing I think when I went into using Shopify was not only was there was an opportunity for me as an entrepreneur to learn and not break everything, which was really important, but also there’s this amazing community behind it all, and there was everyone helping everyone, and there just didn’t exist anything else like that.

Even nowadays, it’s just incredible. I was at an event two weeks ago, Shoptalk Europe, and I was chatting with the Shopify guys, and people just come up to them and they just know each other. There’s just a good community vibe going on around them. And I think that’s what really pulled me into it. And then, of course, being able to start to learn, and all this has been a massive learning process for me as an entrepreneur, and I think it gave me that opportunity, and also not just to scale it, and not just to learn and go somewhere else, but actually have something that I could learn on and then really explore different avenues for expressing Cancha.

Kurt Elster: And so, once you got this Shopify website up, and the product line is evolving, and developing, how do you get the word out? That’s always… The product development is very difficult, but then getting anyone to care about it is seemingly just as difficult.

Jack Oswald: Yeah. It’s extremely difficult. And I think there isn’t one way of doing it. I definitely think that’s the case. And I think you hear about some amazing entrepreneurs that have had a really good following to begin with, and you hear about others that have done… just scored it so well with Facebook ads. In our situation, it’s literally just been a bit of everything. I mean, I don’t necessarily think that’s a bad thing. I think sometimes you get told you need to focus on one channel. I think that is true to an extent, but when you’ve got a limited budget, when you’re trying to figure things out, you do have to try a little bit of everything. You do have to start to get involved with… I mean, one lucky thing with the tennis space is that I had contacts there, and I knew people in the U.S. who had blogs, and review sites for tennis, all that sort of stuff. So, that helped, certainly, in getting-

Kurt Elster: Yeah, you’re already plugged into this different and bigger community that is your audience.

Jack Oswald: Yeah. And so, that was great, and then I think in terms of our story, that resonating with tennis players was a really, really important part, as well. And so, people were able to bear with sort of our learning process because of the fact that they really identified with what we were doing and the story behind the brand, and I think it was unique and different, so that helped, certainly. But yeah, I think scaling things has been a bit of leaning on the audience that I know, and that I’m sort of connected with, but also just same way, trying to figure out how to run a Facebook ad profitably, and how to create good content, whether that’s written, whether that’s through social media. It’s been a little bit of everything and just trying to push forward with it all, I think.

Kurt Elster: All right, so there’s no one channel, but when you combine everything, and you have your story, and you have this product, that is what resonates with people, helps keep you top of mind. It’s very traditional marketing in which it’s like, “All right, once we’ve identified the pain, we have our solution, and we’ve got this narrative, and a spokesperson.” You’re the perfect spokesperson for this. And then you combine that with like, “All right, can we stay top of mind with people? Can we increase frequency?” And that’s the advantage to having those many channels. And it also… I think it takes a lot of the risk out of the equation, right? One channel, say Facebook, could fall on its face one year, but then the others… Oh, good thing you had those available to you, right?

You don’t want to be solely reliant on this single point of failure. So, are you the face of the brand? Are you like… You’re your own influencer here?

Jack Oswald: In some ways. I haven’t got a massive following in the sense that I was maybe a little bit late to that, because I… When I was traveling on the tour, even then social media was… There were influencers but it wasn’t like nowadays where I feel like if I had just recorded everything I would have gained some sort of following. But you know, back then it was still-

Kurt Elster: You could have been big on the Gram back then.

Jack Oswald: Yeah. I could have. With all the photos, yeah. I guess I could have. But I think that… So, in the sense that as the main touch point for the brand, I mean, I have customers who DM me on Instagram all the time. They’ll send me pictures of where they’re going. A lot of them want to talk to me about where their kids are playing tennis, where their next tournament they’re in, and want to talk to me about ideas for product, and I accept that with open arms. I’m so engaged with all of them because I really think that relationship building is such a key part of the whole equation and I think it helps everything. Because I would think we’ve got a very good referral rate. Our bags are quite durable, meant to last, so although there’s accessories and things people buy for their bags, people aren’t necessarily buying unless they’re buying for a friend or something. The returning customer is not incredible. It’s not like a consumable product. But our referral rate is very good.

And I put that down to the product, and then our ability to build relationships with customers, and understand them, empathize with them, stay communicative with them, answer effectively and respond to them in a way that is caring, and I think whether it’s a problem with the product, whether it’s they’re amazed with the product, whether it’s just ideas, and I also think that by incorporating them in the design process, you’re taking on their feedback, it just gets them so more involved with the brand in general and willing to promote it. Because they feel like they’ve had a part in it.

Kurt Elster: So, the outcome, the payoff, is word of mouth referrals, and customer loyalty, even though a well-made bag will last years. You know, my everyday bag, I have owned at this point 10 to 15 years. The company I bought it from has gone out of business, but this bag is going to keep. For sure, this thing’s going another 10 years. But I think… No luck on getting my warranty claims filled here.

And so, repeat purchases are tough. I’m sure if you bring out new lines, new accessories, I’m sure you can get some return customer rate there. But for the most part, those word of mouth referrals where you didn’t have to pay to acquire the customer, right? That’s a big deal. That’s like that top of funnel and those people just get dropped into middle of funnel. So, that’s how we’re measuring success probably, is like post-purchase survey. Hey, how’d you hear about us? Word of mouth.

How are you… You said it’s important, we want to build these customer relationships, we want to build a sense of community, and we want customer feedback. In practice, tactically what does that look like? Customer surveys? DMs? How we doing it?

Jack Oswald: Yeah. I think… Well, one other part of the equation is events, which is really part of the relationship building, as well. And so, we do, especially since that’s been possible in the last couple years, we’ve done events especially in the U.S., where 65% of our customers are, and wee go to tennis events especially, but we’ve started to get into other sports events, in pickleball, and paddle in Europe, and things like that. And you know, this year we’ve got a popup shop during Wimbledon in London next month, so we-

Kurt Elster: Oh, that’s a big deal, isn’t it?

Jack Oswald: Yeah. Stressful, but hopefully it’ll be good. But yeah, that event side of things is so important, because sometimes we break even on it, or maybe even make a loss, but it’s just incredible how many people, especially on post-purchase surveys like you mentioned, come back and say, “No, we heard about you from 12 months ago when you were at that event, or 6 months ago, or last month when I saw you there.” And not only that, it’s like people are amazed that I’m there. They can’t believe it. They’re like, “Oh, it’s you.” And I’m like, “Yeah, I’m here. I’m here with the rest of us.” And they love that. They want to chat to me. They want to ask me about tennis. They want to ask me about the bags. They have some ideas for improvements. It’s just an amazing way to build relationships. Face to face is amazing.

The only problem is, obviously, it’s not necessarily… It is scalable, but it’s not quite as scalable as other opportunities, so we look at other ways, as well, in terms of on site, in terms of getting people involved with community, like an online community. We actually have a really cool integration where people can see other Cancha bag wearers on the map around the world, so they can actually meet up with other Cancha bag owners and play tennis or meet up and go up a mountain if they want to and do some fun activities.

Kurt Elster: So, there’s no replacement for that face to face engagement. I have talked to many people, and many will have got their initial customers, got the business of the ground by going to events. I’ve yet to meet a person who’s done in-person selling at an event and then said, “Hey, what a waste of time. I shouldn’t have done that.” Everybody, even Hoonigan, who’s been around… Huge company. Has been around over 10 years now. They… Talked to them yesterday and they’re like, “Oh yeah, over the weekend we went to this event,” and they could not say enough good things about selling in person at an event, a thing that they regularly do now.

So, it really does not matter what size you are, where you are, that in-person selling, at the very least you engage with a whole bunch of people and get feedback, and I think in most cases it turns into sales and referrals in a way that social media, because it’s so fleeting and it’s such a light touch engagement, right? I saw two and a half seconds of a TikTok video before I swiped on the couch while also watching two other screens and wearing my Apple Vision Pro headset. It’s crazy.

And so, you can’t do better than that in-person engagement. So, what’s a specific change to the product, where someone’s like, “Hey, you know what would be really cool?” And then you’re like, “You know, absolutely. We’re doing that. That is such a good idea. I’m an idiot for not thinking of it sooner.”

Jack Oswald: Oh, that happens all the time. I mean, I think first of all, I think perfection is always the goal but you’re never gonna get there, and the other side of it is that you are not going to please everyone. Some people want a $200 bag for $20 and it’s gonna be tough to provide that. But you know, those who are really engaged and actually say, “You know what? I like what you’re doing, but here’s what I think. This is what I need.” We’ve had customers say, “You know what? I really want an attachment that’s a cooler. I live in Florida. It’s really hot. A water bottle holder doesn’t cut it. I want to keep my drinks cold, but I don’t always. I just want it in the summer. So, I want to have an attachment for when it’s hot and I want to keep my snacks cool and everything.” That’s an amazing idea. You know, some people just want a certain pocket somewhere. Someone said to me the other day, “You know what? I travel a lot and I want to have the pockets RFID protected because I’m traveling places where I don’t want someone scanning what’s in my bag.” Things like that.

Sometimes, I think they’re quite niche ideas. Sometimes, they’re quite broad appeal ideas. I think it’s important to accept all of them and see what’s the timeline for this. How can we bring this in? How many people are asking for this? And you know, do priority order like that.

Kurt Elster: How do you weed out the good ones? Or yeah, how do you get to the good ones and throw out the bad ones? A lot of different ideas in there, and I’m like RFID blocking, I personally don’t care, but I could see the importance of it. For sure, Florida is very hot. If someone said to me, “Look, I need a cooler because Florida,” look, I’ve been. I get it. How do you know which is the one and which is just like you’re gonna end up building the Homer car from The Simpsons?

Jack Oswald: Yeah. It is a tough one. And also, even when we bring out a single product that we’re pretty sure that everybody wants, some people want it a different way than others. And so, we were designing an organizer for one of our bigger tennis bags that can organize everything inside that can be taken out, taken in. You can hang it on a wardrobe when you get to a hotel and take it out, put it back inside, that sort of thing. And then we have very different camps on how customers want it done. Some people want it to be very simple. Others want it to be complicated. It is difficult.

I think it starts with how does that resonate with what we’re trying to do as a brand. How does it help people travel better? How does it help people carry their equipment better? If it fulfills that initial purpose, then we’ve got the green light to think about it more and see about how we can incorporate ideas without… There’s a saying that a camel is an animal designed by committee, because when everyone’s ideas come into it, it ends up just being some sort of kind of mess. So, it’s rare. It is difficult. And I think it’s kind of cross-examining ideas from different places, whether it’s on a post-purchase survey, whether it’s on a survey we send out to customers, whether it’s speaking in person. And even just emails we get from customers. You start to get an idea about what the majority want, and maybe there are some similarities between certain ideas.

Kurt Elster: So, it’s demand. Is there frequency to this? How many people are asking for this? And what’s practical? But then also just trusting your own vision as a product designer with that experience.

Jack Oswald: Yes. Yeah, I think so. I think that’s a big part of it. And then I think also the more that customers are involved with it, even if not all of their ideas make it through, just the involvement is such an important part because they feel intrinsically attached to the brand, and the product you’ve created, and so I think it’s a win-win overall.

Kurt Elster: I want to talk about your website a little bit before we go. CanchaBags dot com. It is such a cool site. It does a lot with short form video, and it’s got some really neat features that I wanted to call out, like on the homepage there’s a bestsellers carousel that’s just got like the feature… Whatever product you’re looking at flips to a quick action shot that’s like four to eight seconds long of someone using the bag in slow mo. You could put me eating a cheeseburger in slow mo and it would look badass. Just showing slow mo… It’s just people wearing a backpack and walking in a park. All right, that would normally be boring. Slow mo on a website as your featured product image, some of it’s awesome.

And then in the bottom left there’s a talking head video of you that’s like… It’s powered by Tolstoy. Check this out. “Hey, I’m Jack. I’m a former professional tennis player and the founder of Cancha.” And so, you click this thing, and you start talking, and then it’s got a quiz on it, and I can jump between videos. What is this thing? It’s cool.

Jack Oswald: Yeah. We’ve been with Tolstoy a long time. We partner with them on different things, as well. Because we understood that we need to find a really engaging way to educate our customers on our products, get across the key benefits as quickly as possible, and there’s no way like video to do that. But also, to build relationships with them, and there’s no way of doing that online other than literally seeing someone’s face and seeing what it means to them, this brand, this product, and having that relationship. And this is the closest we can get to it.

We’re looking at other ways in terms of there’s all this sort of stuff behind live shopping and things like that, but I think that that’s a really good way of doing it. The video helps us get across everything in a short period of time. It really distills the benefits of what we’re doing. It has quite a unique aspect to it. And it also has the personalized, with the quiz, like you said. We can navigate customers to the right thing based on asking the right questions and in a personalized manner.

Kurt Elster: And you said, “Hey, we gotta ask our customers the right questions and in a personalized manner.” There’s also a quiz on the site. Upper right corner in the header. Bag finder quiz. I click that and then it’s like, “Hey, what are you using this bag for?” And I said, “Adventure.” Clearly, I am an adventurer. And then it asked me, I love this, “What’s it need to fit?” Oh, well, I have a camera and laptop would be nice. What’s your gender? Male, female, prefer not to say. And let’s see, my age. And then I have to enter my email or skip. We have the perfect… The Ascendant is the bag. Okay, so I’m gonna click Ascendant. The Ascendant Pack. The ultimate adventure bag. And then there’s more short form video. On the product form it says, “See how others are using it.”

And it’s like, “Oh, I want to see how Elena is using it.” I click that and there she is in Spain walking around using this. That’s very cool. All right, who powers this quiz, and this see how others wear it? How are we doing that?

Jack Oswald: Tolstoy is gonna love this.

Kurt Elster: I’ve never heard of this before. I swear to God. It’s not spon con. All natural.

Jack Oswald: Yeah. No, that’s also Tolstoy for the shorts. For story videos, we have a mix of product. We had sort of trialed that to begin with and we just saw a massive uplift in people engaging with the product, purchasing the product, because they could really… They could suddenly see it. Actually, this is how I’m gonna use it. This is how this person’s using it in this scenario. This is how this person’s using it in this scenario. This is what… When they’re opening it up, this is the different accessories they’re using. That’s been a major part of it. And then the quiz is a different… Jebbit I think is the quiz. So, that is different from Octane, and that’s because it gives us a bit more personalization versus Octane is used, but there’s a lot of different quiz. I mean, it doesn’t really matter what you use. A lot of different quizzes out there.

But that works really well, and we purposefully make it so you can skip it if you don’t want to put your email in, because it’s not about unsolicited emails. We’re not trying to get people’s email. You know, we want to find out more about what they like, what they do, and try and give them the perfect bag. That’s priority one. If they want to sign up for our email list and we can then personalize our emails showing them what they’re pick… We can actually show them that exact product in their emails that they got as a result of that quiz and we can show that to them, we can show different accessories that it recommended to them as a result of that in the email. That’s amazing. But I think the main priority is just let’s help you find it soon. Let’s not waste your time here.

Kurt Elster: The quiz is always clever to reduce that choice paralysis, especially… You know, your case, it is several similar high dollar products. I can spend 200 bucks here easily. And so, I need to think about it. It can’t be an impulse purchase. And then when they’re similar, it makes it tougher, because I’m like, “All right, I know I like these bags. I like the style. I like what we’re doing here. Which is right for me?” And you can create a scenario of paralysis analysis, where the person says, “I want to buy. Help.” And they’re not gonna call you up. They’re probably not even… They’re just gonna leave. You’re not gonna hear from them again. And so, having that tool, and having that social proof, hugely powerful. You are technically sophisticated in your marketing. Your product is technically sophisticated in how you developed it. We heard about RF welding. How cool is that?

And I’m really impressed, man. How old are you?

Jack Oswald: I’m 27.

Kurt Elster: 27?! Oh, man. I’m 40. I’ve not done anything this cool.

Jack Oswald: That’s not true. I’ve seen some amazing sites that you’ve built, and I’m always really impressed, and I’ve been such a long listener of this podcast, and it’s been amazing. I think it’s the definition of really providing value to your audience and really caring about what your audience needs, and I think it’s just such a good role model for all… business podcasts, because that is exactly the model they need to follow, I need to follow, is really stemming it down to, “Okay, let me focus on what people actually want and need and how can I provide that?”

Kurt Elster: You made my morning. That is fantastic. Wow. That’s really good. I appreciate that. Thank you so much. Jack, this has been an honor. Pleasure. Where can we go to learn more about you? Oh, and I see in my notes here, I believe you have a coupon code for us.

Jack Oswald: Yes, we do. I believe it’s TechNasty15, so if you… Yeah, it’s on CanchaBags dot com. It’s on anything. We’ll keep that going forever, so you can always get a discount there. Feel free to reach out to me on LinkedIn, Jack Oswald, or on Twitter. I think Twitter will be in the show notes, but yeah, I’m always interested to meet new people who are doing some really cool things with their companies, and share ideas, find different ways to grow, and yeah, I’m really excited to meet people from this.

Kurt Elster: Jack Oswald, Cancha Bags, thank you so much. Remember, my friends. It is not just about creating great products. That’s what we learned here. You need more than that. You have to connect with your customers, as well, to keep things going and get that delicious, delicious word of mouth referral purchases. Thanks for tuning into The Unofficial Shopify Podcast. We bring you stories that inspire and ignite your entrepreneurial spirit. And until next time, keep selling.