Working at the Outsite Santa Cruz Co-working space with guests. Image: Courtesy of Outsite
I’ve often been asked to tell my story — how Outsite came to be and the journey I took to get here. There were a lot of pit stops along the way, but when it comes down to it, the idea of work and play in beautiful locations sprang from a simple and somewhat selfish place. I simply wanted to find a way to combine work and my passion for the ocean. One year, three locations, 250 guests, 15 company retreats and one surf bus later … I can safely say that dream has become a very real reality.
FROM BELGIUM TO CALIFORNIA:
A few years ago, I was just another mid-twenties guy building my career in Silicon Valley. The Belgium travel tech company I was working for wanted to build out their U.S. branch in California. Dreaming of surf and sand, I eagerly prepped my passport for a new life. But there was one problem. Their office was in San Jose! A place that didn’t exactly fit the beach lifestyle I was seeking.
Life before Outsite was not exactly the California lifestyle I had in mind.
On a weekend road trip I stumbled upon Santa Cruz, and that was the moment that I fell in love with California. Here was this incredible coastal town where you could surf, mountain bike and hike, and where the nightlife was actually decent. I packed my bags and set up a remote office where I could work between meetings and conferences. For the first time, I understood how you could find a balance between personal passions and work. I was inspired, happy, and more productive than ever. It was an important aha moment.
Outsite was born from a simple desire — to combine work and my passion for the ocean.
THE PAIN POINT:
I was traveling a lot during those years, living out of suitcases and conference hotel chains. My career was taking off and I lived in a beautiful place, but I couldn’t shake the feeling of professional isolation both on the road and in my adopted home. Santa Cruz is an amazing place for outdoor lifestyle, but I struggled to meet like-minded professionals like myself. And they weren’t hanging out at those conference hotels, either.
THE PIVOT:
Like many before me, I thought I had to give up the beach to build my career, so I moved to San Francisco and got involved in a few start-up side projects. That’s when I began working from co-working spaces for the first time, and really liked the networking and collaborative spirit it created. That was my second aha moment.
I would return to Santa Cruz to surf every once in awhile, but I had to stay in uncomfortable motels or Airbnb’s far from the ocean. Not to mention, the internet was anything but dependable. It was on one of these surf trips that the idea of Outsite first came to me.
COMBINING WORK & PLAY:
The day I realized I could have it all was when I decided to combine all the elements that had given me such great work/life balance into a co-working hospitality business that would attract a community of like-minded professionals who played as hard as they worked. I beta-tested the concept on Airbnb and Craigslist and quickly found that demand was not going to be a problem. I set out to look for a large villa to rent in Santa Cruz. I had three criteria:
1. Less than five minutes to a decent surf spot
2. An upscale villa and large comfortable rooms
3. Ability to convert a section of the property into a big workspace
Shortly after, I found the dream house and the adventure began. Since launching Outsite Santa Cruz, we have added two more locations to the Outsite collection including: Outsite San Diego and Outsite Lake Tahoe.
The Original Outsite Villa in Santa Cruz (note hammock).
Taking a load off at the first Unplugged retreat to Big Sur.
INVESTING IN THE FUTURE OF REMOTE WORK:
We attract like-minded guests who are as passionate about our concept as we are, and sometimes those guests become investors. Such was the case when the co-founders of Buffer (and Outsite guests) recently made a substantial investment in Outsite. Not only are they betting on Outsite, but the future of remote work. And I can say with confidence that the future is looking bright for both. Stay tuned …
And, if the idea of work + play appeals to you as much as it did to me, come join us for a few days. www.outsite.co
Editor’s Note: This piece was made possible by our friends at Outsite. After visiting a handful of their locations, we can safely say they’re providing a pretty rad place to work, surf, and travel.
