For years Jack Oswald was a touring tennis skilled. He aimed for high worldwide rankings, the important thing to critical earnings. The rankings by no means got here, however fixed journey uncovered a nagging downside: his tennis baggage stored breaking.
Thus started his ardour for designing a greater bag for athletes on the go. And that led to Cancha, a direct-to-consumer vendor of sport and journey baggage, which he launched in 2019 from his base within the U.Okay.
Jack and I just lately spoke. He mentioned his transition to entrepreneurship — early struggles, elevating capital, and extra. Our whole audio is embedded beneath. The transcript is condensed and edited for readability.
Eric Bandholz: Inform our visitors who you might be and what you do.
Jack Oswald: I’m the founding father of Cancha, which implies “courtroom” in Spanish. We design customizable, modular sport and journey baggage — gear that transitions simply between work, play, and health. Our mission is to make sports activities journey seamless and assist individuals keep lively.
My background is in tennis. I spent years coaching and touring to compete, chasing the dream of going professional. I didn’t attain the highest, however I realized an amazing deal and gained beneficial international expertise, together with studying French and Spanish.
Earlier than the pandemic, I started designing baggage for myself to fulfill the wants of an athlete on the transfer — from courtroom to metropolis to nature. I had no background in comfortable items design, however I dove in. Throughout the pandemic, with journey and tennis on maintain, I centered full-time on constructing Cancha and studying ecommerce.
Initially, our goal market was touring athletes, however most clients immediately are on a regular basis commuters and leisure gamers. We’re particularly well-liked within the U.S., which accounts for 60% of orders. Brexit made promoting in Europe tougher, so the U.S. turned our main market. Apparently, we even have a loyal buyer base in Asia, together with Japan, Hong Kong, and Singapore, regardless of not advertising in these locales.
Bandholz: Inform us extra concerning the transition from tennis to entrepreneurship.
Oswald: It was an extended, gradual course of. As a child, I believed nothing might cease me from turning professional. However actuality hit — tennis is hard to make a dwelling in. Solely the highest 100 gamers earn properly, and past 150 within the rankings, you’re usually shedding cash. In contrast to soccer, the place hundreds of gamers make a dwelling, tennis is financially brutal until you’re on the high.
I gave it every thing — touring continuously, chasing rating factors, making an attempt to outlive every week. The grind was intense, and also you’re usually alone with out the identical assets as rivals. A coach, first rate lodging, or perhaps a meal could make an enormous distinction. The psychological and bodily toll is gigantic, particularly when dealing with shedding streaks or setbacks.
I ultimately realized I wanted a brand new path. I in all probability would’ve stored pushing had I not found a brand new ardour with Cancha. Lots of my friends struggled post-tennis, however I used to be lucky to seek out one thing significant. Even so, it took over a yr to completely shift. I used to be nonetheless half-committed to tennis whereas constructing Cancha, regularly accepting that it was time to maneuver on.
Bandholz: Baggage are costly to fabricate. The place did you get the cash?
Oswald: It began scrappy. I wasn’t spending a lot at first. I used to be studying from pals who knew about comfortable items design. Between tennis tournaments, I attended commerce exhibits, the place I met suppliers who generously provided samples, maybe pondering I used to be extra established.
In late 2019, I ran a crowdfunding marketing campaign, elevating roughly £10,000 ($13,500). I had no advertising expertise, nevertheless it offered a little bit of capital to maneuver ahead. Then, through the pandemic, we obtained a authorities aid mortgage, which helped fund our first manufacturing run and enabled us to undertake higher design work. That was a serious enhance.
We started with tennis baggage as a result of that’s what I knew. The idea was a modular system — baggage with add-ons for sneakers, laptops, or moist gear. We first tried a backpack with racket add-ons, nevertheless it was too cumbersome. So we pivoted to a devoted tennis bag and expanded from there.
Having contacts within the U.S. tennis house — reviewers and influencers — helped us get early traction. From there, we’ve grown into different racquet sports activities and extra lifestyle-oriented baggage.
A principal motive for launching Cancha was frustration — my tennis baggage stored breaking. Tennis is a rising sport, however the business itself stays largely conventional, particularly in advertising. Most manufacturers depend on gross sales representatives and retail, and their baggage are sometimes poorly made, used as loss leaders to promote rackets. In contrast to golf, the place premium baggage are the norm, tennis baggage lack innovation and high quality.
I noticed a niche for higher supplies, considerate design, and sturdiness. That turned our focus: premium, modular baggage that meet the wants of recent gamers and vacationers.
On the advertising facet, I additionally wished to interrupt the mould. Most tennis manufacturers rely closely on participant sponsorships, however these include restrictions — gamers who wished to make use of our baggage usually couldn’t. So we went direct-to-consumer by way of ecommerce, bypassing the old-school gatekeepers.
Bandholz: How did your development evolve?
Oswald: It has been gradual. We haven’t had a breakout second from adverts or gifting — no “rocket ship” success. It’s been a gradual enchancment throughout the board. Our baggage are important purchases. They final a very long time, and folks take time to determine. That makes acquisition difficult, particularly with rising advert prices.
Our restricted manufacturing method has labored properly. We’ve leaned into that with e-mail advertising — providing limited-edition drops, unique colorways, and model collaborations inside tennis and past. We’ve additionally performed loads of pre-orders.
Creating pleasure across the product improvement course of and shortage has helped drive engagement and curiosity. As a substitute of counting on one massive channel, it’s been a mixture: constructing hype, sustaining a decent model, and slowly incomes belief.
Bandholz: Do you’ve gotten repeat patrons?
Oswald: Sure, and that’s been a energy. Our modular design permits clients so as to add equipment, naturally encouraging repeat purchases. Folks usually purchase a base bag first, then return for add-ons.
I design equipment to face alone whereas additionally integrating with our baggage. That twin method provides us crossover enchantment — some individuals purchase simply the laptop computer bag, whereas others construct full journey programs over time.
Restricted drops play a task, too. Clients supply suggestions on what they need. That helps information future product improvement. We’ve had clients spend upwards of $2,000 over a number of years. That sort of engagement has been key to our development.
Bandholz: The place can individuals purchase your baggage or attain out?
Oswald: Our website is MyCancha.com. I co-host the Underdog Ecom Podcast for bootstrapped homeowners. I’m on X and LinkedIn.
