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I was a tennis player disguised as an office worker.

While my coworkers were analyzing financial spreadsheets, I was analyzing strokes and string tension data. And while they had aspirations of becoming a CFO or managing director, mine were to have a heavy forehand, big serve, and to play tennis - every single day.

Imagining a day when I could do exactly that I went along, quietly, with the rest of the crowd. Because that's what it means to be an adult, right? But when I met a dope chick in the pro shop, her youthful naivety reminded me that you can live any life you want. 

I worked the overnight shift for years so I could play tennis during the daytime with my friends.

But I couldn't find any tennis clothes that allowed me to express the tennis player inside. Growing up as a skateboarder I was used to creative, stylish designs and artistic expression - the tennis culture is outdated, boring, and jock-ish in comparison as the big brands stay within their lines. There was nothing that truly represented the thousands of hours I've practiced this game. Rolling up in full athletic gear wasn't me, but it was my only option.

One day after tennis I was grabbing some dinner at my local pho spot and couldn't believe it. 

I was sitting next to Chris Cole - one of the greatest skateboarders of all time and a childhood hero of mine.

After explaining that I was a skateboarder turned tennis player we had a thoughtful conversation on the similarities between the sports and agreed they have a extremely technical nature and both take incredible personal dedication - endless hours spent often alone to learn and develop technique. Chris mentioned his young daughter was in tennis classes and how hard it is to get good at at. 

There he was decked out in his pro model signature shoes, custom hoody and beanie - you could tell he was part of a special group. Then I looked at me in my athletic "track suit" and accepted I just looked like another random walking out of JC Penny. It was time for a change.

I imagined my own company. A new perspective on tennis where we aren't afraid to cross lines, take risks, and be different

But there was a deeper internal struggle before this could happen. People don't quit perfectly good careers to start a t-shirt company, do they? You'd never be accepted back into that world after such a childish move - your professional resume would be tarnished. What if you failed? But what if, it was the smartest move you've ever made?

The idea grew through sleepless nights until one day I couldn't continue. I was ready to accept my reality. My reality that I was never that guy that dreamed to "one day work in an office setting". That wasn't me.  Although I thought that I was on the right path to being an adult, I was doing someone else's dream. 

So I quit, and started to live my own dream, on my own terms. Vacation Tennis Co was born.


With only an idea, we threw in our corporate towels for good, sold our belongings, said goodbye to California, and relocated back to my hometown of Richmond, Va where I began documenting the building of the brand from the beginning. 

It turns out that the story of this brand isn't one that can be cleverly designed by business people - it's my real life story.  This is being yourself, this is finding who you are, this is the person I always was - just some skateboarding, tennis playing kid who was obsessed with t-shirt designs. 


Vacation Tennis isn't about winning or being the best, it's about playing


-Robert Gilfillan, tennis player