Tales from the trenches: Iconic Adventures

For some people, the web worker lifestyle is a result of technology. The web enables them to work wherever they want, so they take advantage. But for others the need for location independence comes first and they find the tech and team organization that allows them their wanderlust.

Take Joe Solomon, founder of incentive travel company Iconic Adventures, for example. A dedicated outdoor enthusiast, Solomon realized early that working the nine-to-five grind in a major metropolis wasn’t for him and set out to set up his life as a digital nomad. Gathering a team of like-minded, office-phobic adventurers around him, Solomon set out to use remote collaboration tools to design a business that supported his lifestyle. How did he manage it?


From Asheville, North Carolina to Victoria, British Columbia, Solomon’s team of seven adventure travel pros is spread across the continent. But that geographic profile wasn’t Solomon was going for when he was hiring. It was simply a by-product of the types of people who excel in his niche.

“The people that work in this industry, the reason they’re adventure guides and adventure athletes, is because they want to live somewhere unique. So I knew that I couldn’t ask people to live here. I also knew that they had certain skills that I absolutely need. I need people to understand this industry, how trips run and how trips are developed, how to design trips, and these guys are some of the best, so I decided early on that location was non-existent for me. I didn’t want to worry about that,” Solomon said.

The result is a team that, much like their boss, uses the flexibility of the web worker lifestyle to pursue their passions, whether that’s for mountain biking or making the Canadian national triathlon team.  And according to Solomon, that’s good for business. “You gotta keep ‘em passionate. Most of these guys, if you put them in a big city, I think you’d lose ‘em,” he explained.


“Skype (s msft) conference calls are invaluable. I think you need to bring people together at least once or twice a week to keep that touch point with their main goal,” said Solomon when asked what tools are important to his team.

“Google Apps (s goog) for us is key. I’ve got a giant presentation with a Colorado environmental board tomorrow, so I’ve had this document that has to be sent out to six people and I need feedback. I can send it out there. It’s in their inbox. I set a deadline and they can get it back to me with their response at midnight or one a.m.” Why such late hours? Well, if you’re a serious athlete in training five hours a day, odd hours are necessary.


Solomon finds organizing his team’s schedule to allow them to share the benefits of an untethered lifestyle stressful at times. “As the business owner, you can’t really oversee what people are doing as you would normally in an office, so I essentially trust that people are going to have things done by the time that we ask them to do it. I will say that’s not always the case.”

To deal with this challenge, Solomon counts on a white board of everyone’s commitments behind his desk and insists on hiring people he’s dealt with previously or knows by reputation. He also tries to keep things in perspective. “One of the main traits of all of our folks is work ethic. These guys work very hard. Not so good on deadlines, but I do know that they are great at what they do. It does alleviate some of the stress.”

So would Solomon ever consider returning to a normal nine-to-five routine? He laughs at the idea, brushing aside a suggestion that irregular hours might be stressful. “I usually go for a ride in the morning from eight to ten, so I know that I’m going to have to put in extra hours at night. That’s a conscious decision for us. We don’t cut off at five and then we have the rest of the day off for ourselves. I don’t think we’re stressed because I think the lifestyle that we’ve chosen alleviates that stress for us.”

Image courtesy of Iconic Adventures.