Jack Oswald - Founder and CEO of Cancha & Former Professional Tennis Player
Jack is the founder and CEO of Cancha, a unique startup brand making premium sports and travel bags for modern athletes. "I started Cancha based on my experiences travelling and competing on the international professional tennis circuit. Cancha was born out of the belief that everyone deserves to pursue their passions and see more of the world.
"Alongside my professional tennis and business careers, I have also worked in digital marketing, product design and strategy. I am highly experienced in eCommerce, managing and delivering omni-channel marketing campaigns across various platforms.
"I am deeply passionate about innovation, but also for languages, travel and other cultures. I hold an MBA from the University of Stirling, where I achieved a Distinction, and I also speak French and Spanish fluently. I am looking to connect with individuals within sport, consumer goods, textiles and sustainability in particular."
1 – IF YOU COULD TWEET ONE PIECE OF ADVICE ON CAREERS, WHAT WOULD IT BE?
We came up with several when we were discussing the book. I’d probably pick from one of those. Partly because it was something I took from my father, I’d probably tweet: “Remember, it’s good to have huge expectations, an ambitious goal. But if all you do is dream of something big you will achieve nothing. You have to eat the elephant one toe at a time. Achieving a dream ultimately must be translated to a simple first step.”
2 – WHAT WAS IT LIKE TO WORK WITH DRS SCHUSTER & OXLEY ON A CAREER CAROL?
We did a series of interviews and I suppose my main reflection was that they gave me an opportunity to not only share my experience of building a business but reassess why I choose to do what I’m doing. My days are so hectic with the business that I don’t get too many opportunities to have a good conversation about the ‘why.’
It was a lot of fun to be involved. Helmut and I have worked together for a while, and I have always valued his wise counsel. Slightly jealous now that I have to share Helmut’s advice with a broader audience.
3 – DO YOU HAVE A FAVORITE BOOK WHICH HAS HELPED YOU IN YOUR CAREER OR PERSONAL FULFILLMENT?
Well, as you know, I’m a big sports, particularly tennis, fan. So, I do take inspiration from some of the stories the great sports personalities have shared. Open by Andre Agassi was inspiring and disarmingly honest. It is a tale of overcoming so much. Relentless: From Good to Great to Unstoppable by Tim Grover is also a great read and talks about team and individual performance.
4 – WHO DO YOU FIND THE MOST INSPIRING PUBLIC FIGURE?
Would it be too obvious to say Roger Federer? He is a class act and someone who I see as a role model.
Recently, I’ve followed Rob Burrow’s story with awe and admiration. His apparently unbending optimism and transcendental force of personality are just deeply impressive. How can you not be inspired?
5 – HOW DO YOU UNWIND AND RELAX?
So important to find time and space for meditation and renewal. I love tennis and keeping fit. I love to travel.
Fundamentally, though, I try to make unwinding and relaxing part of my daily routine. I build exercise into every day and deliberately manage my calendar to give me bookend breaks in my day to buffer the intensity of running the business. I think it’s better to think about this as a daily routine rather than run flat out for 6 months and then take a week off.
BONUS QUESTION 6 – IF YOU WERE GRANTED ONE PROFESSIONAL WISH…HOW WOULD YOU USE IT?
Winning Wimbledon seems like a pretty good answer. I think that’s what I might have said 10 years ago. Now, I think I’d say I want to see Cancha succeed. We have great products, with great investors, and a great business plan.
Photo credit - courtesy of Jack Oswald and Cancha.