My personal travel business evolution of ExploreThere


Over the last few months I’ve been pouring myself into a venture that has lived many lives over the years. You could say that its the feline equivalent of business with more lives than any business should have. Lots of startups pivot, but this one has died and come back over and over again.

Back in 2008 while traveling around Peru, I had this grand plan that ExploreThere was going to just document my adventures around the world. I started it and kept this going for a time, but ultimately this didn’t work out as well as I had hoped. I wasn’t spending all of my time on the road, and I found the downtime very hard to actually write about experiences that happened in the past rather than something I felt I should have been experiencing right in the moment.

Sure that could have turned into something had I actually kept it up, as there are many examples of successful travel bloggers such as Nomadic Matt, but ultimately its a very difficult market to make a business out of unless you have a constant stream of content.

Between 2012 and 2014 I attempted to turn ExploreThere into a travel news site that I actually had many writers writing for, but the difficulty in getting traction with little to no budget was an issue. This limped along with people contributing for almost a year before I finally gave up on this due to external circumstances that were taking away my focus. It sat there idle for a few years.

I started traveling a little more again around the USA and Asia at that time I was working for a few clients between trips, but I started realizing in Asia it really wasn’t all that difficult for me to also work while I was traveling. I had a lot of downtime between the different things I was working on, and I always tended to go on longer trip lengths by American standards anyhow, so why not just get some work done to pay for those trips if I could.

All was grand. I can travel and make money? It’s the perfect storm of awesomeness and it felt like I was in the eye. Chaos surrounding me, but I’m drifting along in the center like in this harmonious place where I’ve got the best of both worlds. Work and Play.

I spent a couple years in this spot doing my consulting work with clients and going on trips. I was generally content with this life I had made for myself, but I still had the itch to create a scaleable business, not just one where my income was limited by the time I had available.

Fast forward to late 2015.

I started talking with some people about a few of the ideas I had floating around on my head in the travel space and in early January I had started to work on some of those ideas with a friend. Several pivots happened in January and February when we realized some of the chicken and the egg problems that were in front of us in this space.

By the beginning of March momentum had died out and once again I found the idea somewhat dead in the water. The idea we were working on was going to take some serious cash to float the company until we could gain traction and fundraising was really not something I was willing to consider at the time. I want to build a business that is mine with no money men to answer too that don’t actually have the companies future goals in alignment with my vision for what it could be. If there is one thing I’ve learned over the years through watching my friends go through investment processes, it’s that the second you take any money from institutional investors, you don’t own your company anymore. It takes a special kind of investor to let a founder run with their vision without influencing it.

I spent the next several months thinking about what I could do, and I realized that in the past year I had shared rental properties with others in different cities while working on my client work still. I had also helped create one of the first co-working spaces in the United States about 12 years ago. What would happen if we meshed this idea and made trips that would specifically be focused on helping remote workers, co-work and co-live, in really amazing places. Would people buy that? Turns out they will.

I partnered up with a friend to start a test run of this, and at the moment, that is the current iteration of where I’m at with ExploreThere, and it finally looks like it has got legs to run with and we’ve got trips on the schedule right now for Mexico, Colombia, and Argentina.

Some people really just don’t want to deal with all the logistics of planning a trip. It can be a hassle for sure. We aim to fix some of those logistical issues for them, make them feel safe traveling in a place they are not familiar with by traveling with a group, and introducing them to other interesting people along the way. Its a win win.

We also have some great competitors in our space. Yes, I just complimented my competitors. I complement them because some of them are doing some really cool trips. Some that I actually wish I could go on. RemoteYear is a close competitor of ours who runs year long planned itineraries. With 12 cities in 12 months, it’s very similar to us, but it is has some issues I aim to address.

What is different you might ask between ExploreThere and RemoteYear? Its simple. Flexibility for the remote workers who might not have a year to spend away. Maybe there are other things that hold people back for one reason or another, but going for a month or two is a much smaller commitment than planning to go on a trip with the same people for a full year. Like I said though, I would love to go on that trip. The truth of the matter is that each company can really only handle several hundred to a thousand participants a year, and the number of remote workers who would love to travel more far exceeds those numbers. There is room for all of us and people will pick what they want to do based on their personal preferences.

I’m making partnerships, marketing our first trips, and getting really excited about what the future may hold for ExploreThere in this space I’ve really wanted to be in for a long time. I can’t wait to see where it all goes from here…

If you would like to join us on any future trips, please make sure you head over to ExploreThere. We send out a couple emails a month announcing new trips and other deals like the competition we are currently running to giveaway a free trip occasionally. If you’d like to join that giveaway, please go directly to our trip giveaway and read the very simple instructions!

Hope to see you all on one of our trips soon!