Outsite is a new retreat concept for professionals, entrepreneurs, groups and digital nomads who want to get away and get focused. We had a chat with Emmanuel Guisset, founder of Outsite, to find out more about the concept and what the team is up to.

Emmanuel - tell us a bit about yourself and your background - where do you come from and what have you been up to so far?

I am originally from Belgium and I got relocated by my company 6 years ago to run their US branch in Silicon Valley. The company was a travel tech startup and I was doing mainly business development and marketing for them in the US and South America. I did my fair share of traveling going to conferences and meeting clients. I also worked on a photo app startup which failed like many others :).  I have come a long way from being a regular employee in Belgium to becoming a fully remote worker and now an entrepreneur.

How did Outsite get started?

I started to work remotely from Santa Cruz, a beautiful surf town only 45 minutes away from Silicon Valley because I was tired of boring San Jose. I had a very good lifestyle, enjoying the ocean and outdoors before/after working sessions. My problem was that I felt isolated and didn't really meet a lot of likeminded people with the same lifestyle. So I decided to move to San Francisco and lived there for 2 years.

My social life improved quite a lot, I found out about the coworking movement and stayed in some spaces that combined coworking and accommodations. That's where I decided to create a space in Santa Cruz where professionals like me could stay for a few days, work and do fun outdoors activities together. Funny thing is that now Santa Cruz is booming! It pulls a lot of people attracted by the lifestyle and the proximity to SF and Silicon Valley.

Tell us more about Outsite - what is the core idea behind it and what are your main goals?

The core idea is to provide spaces in beautiful locations where professionals can stay, work and play together, whether it’s for a few days or a few weeks. My main goal is to expand the concept to all kind of fun locations, whether it’s at the beach, mountains or even the countryside - everywhere but in the big urban centers where most offices are still located.


How do the bookings for Outsite work - can it be a single person going as well as a group or team?

Most of our guests come alone or with  their girl/boyfriend or a few friends. We do have more and more team retreat requests and we had companies like LinkedIn, Google and Facebook that did retreats and offsites. I see a rising trend of small groups (10-20 people) work+play retreats in the Bay Area.

Who else is in your team and what do they do?

My girlfriend takes care of operations. She first started part time while having a remote job (medical coding) but it has turned into a full time job, managing the bookings, administration, HR needs and all the accounting. We also have Britt, who started as a site manager for our Santa Cruz location but now is slowly turning into creative project manager putting together cool media material and merchandise. Then there is Lindsey, a nomad writer (Check her blog - The Elegant Hippie) who manages all our content marketing and social media. We also work with Dani, architect and interior design. She makes sure our spaces have good art and design!


Which locations do you currently have available and which ones are you planning to have in the future?

Santa Cruz and Encinitas located 30 minutes north of downtown San Diego. If everything goes well, we should open Lake Tahoe this winter. We are also getting a lot of requests for Hawaii, so I think we will have to open it sooner than we thought!

How do you find your retreat locations and what are your requirements for them?

That’s the most difficult part of the business. I won’t give you too much details, but it’s a mix between location/size/price and proximity to urban centres, while being surrounded by nature.

What kind of shared events or activities do you organize for the retreats?

That varies, but typically we have the classic activities like surf and yoga classes, BBQs and communal dinners. We also sometimes organize beach clean ups, hiking trips, tours to the nearby organic farms, and we organized our first scavenger hunt for a LinkedIn team retreat last week.

Tell us about the individual projects (Code & Surf, Surfbus etc)?

Code & Surf was organized in partnership with the online coding school Career Foundry. They did a pretty amazing raffle to get 10 students from all over the world to code and surf in our space in Santa Cruz. At the end, they all had a lot of fun and they came up with 2 really cool projects. One was a personal travel guide app that they called Britt after our manager!

I had heard of ski trips for startups so I decided to put together a surf version and add a speaker panel about remote work to raise awareness about the remote work lifestyle. A lot Bay Area startups are often complaining about lodging and life expenses in SF and Palo Alto, and my idea was to bring a few of them in Santa Cruz to make them understand there is an alternative.


What are the biggest challenges you’ve come across when starting and running Outsite?

There were so many. I did some A/B testing beforehand so I knew there was a demand, but I started in winter so I had to rely on Airbnb bookings at the beginning. Now that we are more established, I have managed to get the majority of our guests from our website. We also had to put more time and money in the space to accommodate the needs of remote workers.

What about some of the best experiences and achievements you've had?

What I am most proud of is the number of recurring guests we have had. Some became friends and are really involved in the community. I am also very happy with our 2 events - Startup Surf Bus and Unplug. It went so well that we have decided to make them recurrent. Last but not least, being able to accommodate, entertain and satisfy a 22 person LinkedIn executives team was quite a achievement!

Big Sur 1_

What do you think the future has in store for Outsite?

Hopefully the community will grow and the new locations will keep popping up!

How familiar are you with Teleport? What do you think about the general idea behind what Teleport is trying to achieve?

Rodolphe from Remotive.io told me about it so I checked it out. I love the concept and it definitely fills a need for nomads, startup teams and remote workers. It’s a bit like Nomad List on steroids! I am also impressed by your team. This could go big!