Dell Technologies Enabled Entrepreneur to Launch Remote Company

The following is a guest post from Greg Caplan.

Remote Year originated from my desire to work and travel the world. After a couple years in the workforce, I was tired of the 9 to 5 grind and longed for something more, but didn’t want to stop earning an income. I reached out to a couple friends to see if they would travel with me for a year, but they refused to leave their jobs or homes behind. In an effort to find a community to travel with, I setup a website asking “who wants to travel together for a year while working remotely?”

50,000 people raised their hands.

From there, Remote Year was born and grew into a million dollar startup, receiving $12 million in series A funding, developing 20 unique programs and sending workers on life-transforming journeys around the world. We coordinate trips for groups of 60 people to live in 12 different cities a year while keeping their jobs and working remotely.

According to our recent survey with C and CO, 55 percent of remote workers telecommute full-time. People are entering remote work in droves as new communication technologies evolve to enable employees to seamlessly exchange data regardless of geographic constraints. The traditional “office” culture has changed tremendously because of disruptive technology and companies like WeWork that provide an office environment for anyone at any time. Our partnership with WeWork allows us to have great office space whenever we need it wherever we are. Program members have unlimited access to WeWork locations while traveling on the program.

Remote work became an explosive trend in 2014 and I faced many challenges and growing pains when starting my company to meet the large demand for community-oriented travel and remote work. Employers are embracing this trend and are implementing programs to allow employees to work where they are most productive, and this is only accelerating. Developing a fast-growing company was no easy venture. To keep my employees happy and well connected despite working across the world from one another, I started utilizing platforms such as Slack and Zoom to keep the business running and communication lines open. Slack is our main productivity and collaboration tool that we use to chat with one another, which dramatically lightens our email inbox and streamlines one-off questions and daily communications. We conduct all of our conference calls on Zoom, which offers remote conferencing services using cloud computing.

As the business expanded, I had to figure out which tools, products, software and technology to utilize for the business. My Dell Small Business advisor taught me how to protect my data through solutions such as VPNs and cloud storage, and how to invest in technology that meets my current business demands and also takes future growth into consideration. One must pack lightly to uproot and travel constantly, so my advisor helped me pick out my Latitude 2-in-1 that was mobile and versatile, while also meeting my personal and professional needs.

After years of running a company remotely that purely supports other remote workers, I’ve learned to adapt constantly. Participating in a year of traveling presents unique challenges and circumstances to our group members and RY employees. Participants must continually adjust to new environments and depend on digital communication and technology to conduct their day-to-day work. Technology is extremely important to achieve the best of both worlds in this program, but it’s also constantly changing, so we must keep up to successfully do what we do.

I struggled with operating a company that was scaling; however, Dell Small Business became an extension of my team. It helped improve our technical efficiencies and supported me with any IT question I had – big or small.

I never thought I would be in the place I am now – running my own company, enjoying the work I do and traveling the world – all while sharing it with a like-minded community. I am excited to continue to grow the company and provide others the opportunity to broaden their horizons and experience the life-altering moments that come with seeing the world.


Greg Caplan, Founder and CEO of Remote Year.

Remote Year brings together groups of inspiring professionals to travel, live, and work remotely in different cities around the world for a year or four months. Greg is a proud graduate of the University of Michigan.

About the Author: Erik Day

Erik Day has been at Dell for over 16 years. He first joined the company as a temporary consumer sales agent in 1999 shortly after finishing his Bachelors of Psychology at Southern Methodist University in Dallas. Erik has held multiple sales, merchandising and marketing leadership roles in his tenure at Dell which has taken him to 25+ countries over 5 continents. Erik spent 2009 to the early part of 2013 leading Retail Merchandising, Retail Marketing and CSB Direct Media Budget and Planning for the Europe, Middle East & Africa region. Most recently, Erik has been responsible for leading an outstanding team of sales leaders covering large format retailers and CSB distribution channel partners across the United States and Canada. Between 2013-14, Erik built a $500M Acquisition business in retail and helped grow Best Buy over 50% YoY between 2014 and today. Erik is an avid tennis player and just got married in August of this year. He loves spending time in Up North Michigan on the Lake with his husband Craig and their 2 Samoyeds, Chester and Chase.