Exclusive interview: Founder of Cancha sports bags

For many of our readers, the dream of creating a brand new racket sports product then turning it into an international business might seem…. like a dream! But Cancha has proven it’s not impossible as the founder explains how he identified a problem, created a solution and launched a global business all within 5 years.

Jack was born in the UK but spent most of his childhood in the USA. He now spreads his time between bases in London and Virginia as well as travelling to Asia and Europe to meet suppliers and partners.

Racket Business: Tell us why and how you founded Cancha?

Jack Oswald: I started In Cancha because I was really living the problem. I was a travelling tennis player, spending a lot of time on the road from a young age because I had a dream of trying to make it on the tour. I played in junior tournaments while my parents were living in the US, so I was already spending a lot of time back in the UK, as well as in France and Spain—training and living there from the age of about 13 or 14. It was a really fun experience, but I also found it quite frustrating, especially when it came to travelling with tennis gear. As a young player, you’re carrying your rackets everywhere you go.

I was constantly lugging around rackets, school books, training equipment—everything I needed for being on court and on the road. It was genuinely difficult, living out of a suitcase and a tennis bag. On top of that, I had loads of bags break on me over the years. I went through so many tennis bags because they just couldn’t handle the wear and tear. I always felt like they were really poorly made, as if there wasn’t much thought put into them. It seemed like the industry didn’t care much about the design and functionality of tennis bags, even though, for me, it was such a central part of the experience.

So at first, I started designing a bag just for myself. I was still travelling a lot, playing lower-level Futures events and the like. That was the essence of it in the beginning—just trying to make things easier for myself.

As I met other players along the way, I got a lot of feedback. I gave bags to players to try out, and I started to get more and more interested in soft goods design and industrial design. That’s really where it all started.

Over time, it’s evolved. Now, most people aren't travelling to tournaments all the time. These days, it’s more about helping people integrate tennis—or racket sports more broadly—into their daily lives. Whether it's commuting from the office to the courts or heading off on holiday, we want to make it easier for them to carry their gear and fit the sport into their routines.

Racket Business: Was it also about having an entrepreneurial urge? Or was it more like, I need a better bag, so I’ll just make one... oh wait, maybe I could sell this? Was there a point where you thought, “Actually, I want a career as a businessman”?

Jack Oswald: No, not really. My dad had a business when I was growing up—most of my life, really—until he retired. That’s why my parents moved to the US. But I never thought twice about going into business myself. I just remember my dad being stressed all the time, always worrying about where the next bit of income was going to come from. That never appealed to me.

I always assumed I’d get into coaching or something like that if playing professionally didn’t work out. I wasn’t even planning on going to university. So yeah, the business side of things wasn’t something I thought about at all.

It all just came from wanting to bring the idea to life. But then I gradually became more interested in the business side because I started to see some parallels. I think there are similarities between starting a business and playing singles tennis—it’s a very solo endeavour. You’re figuring it out as you go, and your situation is always different from everyone else’s, whether that's in terms of your physical condition, finances, or just your personal path.

It’s a bit of an internal battle, and I think that mindset from tennis helped me as I got into this. That’s probably what drew me in.

Racket Business: This actually digresses from the questions I meant to ask you, but it’s quite an interesting point because I feel the same way. I played tennis to a decent level and, when working in business, I often find myself in situations that feel familiar—almost like I’ve experienced them before on a tennis court.

I’ve been in job interviews thinking, “This is easy compared to being in a third-set and a break down.”

Jack Oswald: I know exactly what you mean. Sometimes I actually feel a sense of relief in business because you often have time to make decisions. You don’t get that on a tennis court—you’ve got 20 seconds between points and you have to make the right choice: where to serve, how to play the point. The feedback in tennis is instant, so you quickly pick up patterns and start to adapt. In business, that feedback loop is much longer, so you can’t always react the same way. But yes, definitely—there are similarities.

Racket Business: Do you think there's also an element that tennis players like solving their own problems? They like coming up with solutions immediately. Do you run your own business because you want that control and how do you think you’d handle being an employee, with less say in decision-making?

Jack Oswald: I think I’d struggle quite a bit. In the situations where I have been an employee—not many, to be honest—I’ve found it difficult. I constantly feel like, “I’d do this differently.” In tennis, you call all the shots—pardon the pun. When you run a business, you do the same. And I like that.

But the struggle I had trying to make it at a serious level in tennis is similar to business: there's a lot on the line, and it can feel very isolating. Whether it's in tennis or business, being on your own is tough. Sometimes I wish I had a co-founder or someone to share it with. But I didn’t have that on the tennis court either. No one can fully understand what you’re going through, what you're trying to achieve, because they’re not living it day-to-day. That’s another similarity.

Racket Business: In terms of Cancha’s involvement in the racket sports industry, do you see that becoming a key part of the company’s growth over the next few years? Or is the racket sports market not big enough for your long-term goals—do you think Cancha will have to expand beyond racket sports?

Jack Oswald: My ego response is that I’d want to expand beyond racket sports. But I’m always surprised at how quickly the racket sports industry is growing—sometimes faster than we are. That’s partly due to the rise of sports like padel, but also because, especially since the pandemic, there’s been a lot of disruption in the tennis space. From that perspective, I think there’s still a huge amount we can do within tennis and the broader racket sports industry.

That said, at some point, I would like to see Cancha move beyond that. But right now, it’s still very close to my heart, and I think there’s still a lot of opportunity there.

Racket Business: Cancha’s around 5 years old so in that time, what would you say has been the biggest challenge? And also, what would you consider your greatest success? I know it can be hard to pinpoint specific moments, but if there are any that stand out...

Jack Oswald: I started designing the bags and everything back in 2018, but we weren’t actually a business at that point. We officially became a business in 2020. So it's coming up to five years old at the end of this year

In that time I think there have been a lot of challenges. One of the biggest, I’d say, is similar to what you deal with in tennis. Something I think I’m quite good at is focusing on incremental improvements—because that’s something you have to get used to in tennis, especially as you get better and the gains become smaller and more refined.

You're often seeing only tiny bits of progress, but you learn to enjoy that process. And it’s very similar in business—there are some big wins, but most of the time it’s about small, gradual improvements. I haven’t struggled too much with that part.

What’s been harder is dealing with external forces—things completely outside of your control. Right now, for instance, issues like tariffs and changes caused by Brexit when we first started—those things can be really disruptive. When you're selling internationally, it adds so many more variables to consider. Navigating all that has definitely been a major challenge.

There are always unexpected issues that crop up too. That unpredictability has been one of the toughest parts. Financial stability is another big one. I relate it a lot to the tennis circuit—playing Futures tournaments, earning maybe $150 a match, while trying to cover your hotel for the week. It's the same thing with Cancha. There are times when we’re doing really well, and then times when we’re hit by unexpected costs that make things very tough.

So those would be the two main challenges: external factors and financial unpredictability.

In terms of success, honestly, the fact that we’re still here is probably the biggest one. That might sound simple, but there were many points early on where things could have gone under—very, very nearly. And then there’s the community. A lot of founders talk about community, and I try not to over-romanticize it, but we really do have an amazing customer base.

Some customers have bought eight bags over the years. I didn’t expect that kind of loyalty. Just two days ago, I met a customer in London who came over from the US. They messaged asking if I was around and if we could meet up, and I love that. We do events and things, and that personal connection really means something.

Even when I’m walking through London and see someone with one of our bags, I have to go up and say hello. It’s moments like that that make it all worth it. It’s more of a general success, but for me, just having that kind of connection with people using something I’ve built is probably the most rewarding part.

Racket Business: Fantastic. I can relate to that. It really is a buzz. And actually engaging with customers who’ve bought your product—it's incredibly rewarding as a business owner. Most people are kind, encouraging, and genuinely want to help. That live feedback is invaluable.

Jack Oswald: Exactly. Just to give another example—I still personally handle all the customer service for Cancha. It’s a bit of a nightmare sometimes—some wild messages come through—but it makes such a difference. When I reply to people personally, whether it's about a product restock or just to build a relationship, they really respond to that.

I’ve got customers who’ve emailed me every week for the past two or three years. They’ll email our general inbox just because they know I’ll reply. I’m not sure how sustainable that is long term, but I do it because that connection really matters to me.

Racket Business: As an entrepreneur in the racket sports industry, what changes would you like to see? How do you think the landscape will evolve, and how will Cancha adapt?

Jack Oswald: I’d love to see less gatekeeping and more innovation. More support for new ideas and emerging brands. Not just "younger" brands, but any kind of innovation in the sport. For a long time, tennis has been a very closed ecosystem—especially when it comes to things like sponsorships. Traditionally, the only way to break through was to have sales teams across the country and big-name endorsements like Roger Federer to get any sort of visibility.

Tennis stuck with that model for a long time. But over the last five, maybe ten years, things have really started to change. Even within the sport, from how media is distributed to how players can now have their own voice—it's forcing the industry to evolve, which I think is a great thing.

Racket Business: Do you think there’s still a bit of protectionism in tennis against sports like padel and pickleball? And do you see that in your work?

Jack Oswald: I think there is. But I also think those boundaries are being broken down. I used to feel that way myself for a long time. I’m incredibly passionate about tennis—it's always been my main racket sport, and I’ve played it all my life. So it’s natural to feel like these newer sports are intruding or even threatening tennis.

But I think organisations like the LTA have made the right move by embracing padel and taking ownership of its growth.

I believe that, overall, it will grow the entire racket sports category. In fact, I think you’ll actually see increased participation in tennis as a result. Sure, more people will play padel, but we have to acknowledge that tennis is a tough sport to pick up. It requires a lot of dedication, and I don’t think the sport should suffer because of that.

So, if there are other entry points into racket sports, that’s a good thing in my view.

Racket Business: I suspect a lot of our readers are current tennis coaches, and they’ll read this and think, “Right, Jack has inspired me to start my own business—it’s really interesting what he’s done.” So, what would your advice be to a racket sports coach who’s thinking, “I need to get off court. I’m exhausted, and my earning potential is capped. How do I start my own business?” What would you say to someone in that position?

Jack Oswald: I think the most important thing is to start with something that genuinely matters to you. That’s crucial—because it’s not going to be easy. The market is increasingly saturated in many areas, but that shouldn’t be a deterrent.

What matters is that you care deeply about what you’re doing—not just about running a business, but about the problem you're trying to solve or the purpose behind it. That’s what will keep you going when things get tough.

I don’t really believe in the idea that you need to find perfect product-market fit from day one. Whether it’s a product or a service—especially in the racket sports industry—you just have to keep adapting and improving.

If you're passionate about it, you’ll keep learning and refining, and your offering will naturally evolve and get better. In my view, that’s the key.

Racket Business: Racket sports are, in some ways, massive industries—but also quite niche in others. If someone’s about to start a business, how do they know if their product or service has a big enough market to support it? With bags, for example—everyone has a tennis bag, so it makes sense. But other ideas might not be so obviously scalable. Is there a way to test that?

Jack Oswald: I tend to think that nowadays, no niche is too small. There’s obviously an upper limit, but it’s much bigger than most people realise. So that’s the first thing I’d say.

It’s unlikely that your idea is too niche—at least not in a way that would stop you from making a good living. Becoming a household name might be another matter, but that might not even be your goal.

And if you keep evolving and adapting, you can expand into different directions over time. So I don’t see that as a huge issue.

In terms of testing an idea, I’d suggest doing it as leanly as possible—that’s a mistake I made at the start. A lot of people look at what established companies are doing and think they have to replicate that, but that’s not necessarily true.

These days, with the reach you can get through digital channels, you can test ideas in a very lightweight and cost-effective way. I’d definitely recommend that approach.

Racket Business: That’s great advice. Which racket sports brands have influenced you the most?

Jack Oswald: Good question. In terms of brands—I say this with the caveat that I think many of the long-established tennis brands haven’t done much in the last 20 or 30 years.

Brands like Babolat and Wilson come to mind. Wilson has done some great work in marketing, I think, more so than with product innovation. That said, there are some areas where it’s genuinely hard to innovate—like racquets themselves, especially given the dominance of manufacturing in the Far East.

But I’ve always played with Head racquets. I liked the way they had their innovation centre in Austria and the focus they put into R&D and quality. I think they’ve had to broaden their appeal in recent years, but they were definitely an inspiration early on.

And now, I’m seeing more companies doing interesting things—brands like Lacoste, Tecnifibre, even Wilson again—more so in their marketing and messaging than in the actual products. But it’s refreshing to see brands evolving. It’s just taken a while for them to get there.

Racket Business: And last question, which I think you've answered already, but if you weren't creating racket sports bags and luggage for a career, you said you'd be a tennis coach. Is that correct?

Jack Oswald: Yeah. The thing is, I think the idea of me becoming a tennis coach was more about it being the only other thing I could probably do. I don’t actually think I’m very good at coaching. I used to struggle—though I think I’m better at it now—with really caring about other people’s progress. That sounds bad, I know, but when you’ve spent so much time just trying to improve yourself, it can be difficult—or even frustrating—to deal with how long it takes others to pick things up. I think that’s just part of it. But I do see it in a different light now.

Honestly, I think about it a lot, and I have no idea what else I’d be doing if it weren’t for the Cancha. I definitely wouldn’t still be playing—something would have run out, like money, for sure. So yeah, coaching probably would’ve been the next thing. Or maybe I would’ve figured something else out.

Visit Cancha’s website to see what Jack has created