How We Built Our Business ‘Trip Outside’ From Our RV

With the dawn of project management software, more widespread cellular connections, and business tools for online and digital entrepreneurs, the digital nomad lifestyle is at its peak.

My husband Reet and I have hopped on the working-while-traveling train and we’re enjoying the exciting ride while traveling full-time out of our 23-foot Class C RV. We left our corporate careers in 2017, packed up our adventure gear and 2 cats into “Miles” our RV, and hit the road.

We wanted to be able to travel more, work from anywhere, and focus more on our passions of travel and outdoor adventure. Starting our outdoor business allowed us to do all of these things, as well as help get more people outdoors!

We had a big idea for TripOutside.com, and started building it as soon as we started traveling. We weren’t sure how easy it would be to start a business from an RV, while traveling frequently, and spending time in remote areas… and it’s all been a big learning experience. But we found out that it’s totally possible – and actually very beneficial for the industry we are in!

Starting and growing TripOutside from our RV has taught us so many things, and introduced us to many useful online business tools that are ideal for anyone who wants to start doing business in the digital world. We’re sharing some of them today – read on for more!

Turning a Hobby Into a Business: The TripOutside Story

There’s truth in the quote “work on something you love and you won’t have to work for the rest of your life.” Before TripOutside – our digital business – we both worked in the corporate world, at a Fortune 300 company. Our 25 combined years of experience in Finance, Merchandising, managing service providers, and running profitable business segments helped us gain the knowledge and skills we needed to start our own venture.

Our real passion is the outdoors – so much so that we spent most of our free time outdoors – camping, biking, paddling, snowboarding and more. While renting gear like bikes, kayaks, SUPs and snowboards, we saw a problem to be solved with the outdoor adventure booking process. Researching the best adventures and destinations, comparing local shop reviews, ratings and prices on different websites, calling different shops to check on availability and book gear or trips, and waiting in line for gear ate away at our limited vacation time. That’s how the idea of TripOutside came about. TripOutside was brought to life to make the outdoors more accessible to those who yearn for it.

Starting a business is never easy – but the benefit of turning our hobby into a business is that we face each challenge with excitement because we love what we’re doing and we’re passionate about the outdoors! Entrepreneurship, particularly being digital nomads, is extremely exhilarating because it gives us the flexibility to live our lives the way we want to. We decide where we want to be, what we want to work on, and how we balance our time and lives. We are able to look at our most precious asset: our time, and decide where we are going to spend it. But it also requires a TON of discipline, because with flexibility comes the need to evaluate and structure for success.

Finding Your Business Purpose

Just like traditional businesses, online businesses face relentless competition. In the sea of businesses similar to yours, having a purpose you are passionate about can make all the difference.

For TripOutside, our purpose was inspired by one pain point – complicated bookings! TripOutside was created to allow outdoor enthusiasts to find the best local shops, compare prices, check availability, and book outdoor gear and adventures all on one website. We feature the best local shops for tours, trips and rental of bikes, kayaks, stand up paddleboards, canoes, skis, snowboards, rafts, surfboards, camping gear and more.

For 2.5 years now, Reet and I have been traveling around the country in our RV Miles, meeting our outfitters and customers face to face. We have spent so much time talking to both customers and outdoor shops about their businesses to understand their needs and challenges. We learned a ton through these discussions, and it actually resulted in an early pivot in our business plan. We now realize how important it was to do this, because it allowed us to focus on solving their real problems – not what we thought their problems were! This has been a huge benefit of traveling – not many businesses get to meet their vendors and customers face to face, see how their businesses operate, and even take part in the services they are offering.

It’s actually our favorite part of traveling in our RV – being able to “post up” in one of our favorite destinations for a month, talk to all of the outdoor shops in that destination, and experience the outdoor adventures we feature on our website.

The other big benefit of our RV lifestyle is how close we can be to the outdoors. We save so much commuting time – when we want to take a break and go for a ride, we can typically just jump on our bikes and go!

Working on the Road: Important Tools to Have

Making money while being on the road used to be challenging. Luckily that has changed. We meet digital nomads all the time that are doing the same thing as us – running businesses, freelancing or even working for companies all from the comfort of their RV. But working remotely 100% of the time has its challenges. Not only do we have to be very disciplined, but we need to figure out ways to be successful without being in-person with our teams, co-workers and partners. We use several awesome tools that make creating, running, and maintaining a remote business so much easier.

Hiring People

TripOutside’s business goal is to get people outdoors and adventuring. We travel full-time, and our office is the outdoors! It only makes sense that all of our workers are also remote. It is in our business blood to be nomads! We want all of our employees, contractors and other workers to also be able to live and work where they want to, hopefully near outdoor adventure!

Nowadays, tools like Upwork and Fiverr make finding fellow digital workers super easy, and help your business flourish. We work with many different contractors and freelancers all over the world using these platforms, and they make reviewing candidates, communicating with them remotely, and paying them all a breeze!

Online workers are usually more flexible, and because they aren’t constrained by tight schedules, they are more creative and enthusiastic. It just makes sense that digital nomads hire other digital workers!

Managing a remote group is unique – communicating with them constantly, setting clear objectives, and expressing clear goals are key to keep them focused and guided.

The quality of freelancers on these platforms can vary however, so we strongly suggest doing a small project with 3-5 top potential candidates to see how they do before jumping into something larger. It will help you evaluate their work, adherence to deadlines, and communication style. This is something we learned after having a few disappointments early on.

Communication

In the digital nomad’s business life, communication is very important. For weekly calls, client-catch ups, and brainstorming, we choose apps like WhatsApp, Messenger, and Skype. These avenues are great for short, quick communications like sending documents and links and answering questions. We find that online chat in particular is super helpful for quick questions and messages that don’t require a lot of explanation.

Trello, Asana, and Basecamp

If you’re managing a team, or any project with other people, Trello, Asana, and Basecamp are some amazing online project management tools. These websites allow you to clearly break down tasks, and monitor the progress of each goal or task. All three have excellent free trial versions that allow you to track projects, comment on tasks, add labels to assignments, and receive reminders through email alerts. Our favorite of the three is Trello – we just love their features and the mobile app makes it easy to manage everything right from your phone.

Google Drive

Sharing documents with your team is now made so much easier with Google Drive. We can create documents and spreadsheets that our team can also access, add instructions, and review completed work easily.

Video Training

Training team members and onboarding new people – no matter how far they are from you – is key to making a business run as smooth as possible. For more extensive training and communication, we utilize video training frequently. Tools like Snagit and Loom allow you to create a video from your computer, with voice and screen “sharing” to show exactly what you are working on and talk them through the training. The videos are typically large, so we save them as shared documents in our Google Drive, so the team can access them as needed. We use this method for explaining new projects, training our team on processes, and showing them how to use various tools and software.

Using SnagIt also helps you create more meaningful connections to each team member.

What About Wi-Fi?

Lastly a note on Wi-Fi. Having a strong (4G LTE) and fast (10 mps+) is absolutely critical for remote work. We do extensive research on our destinations in advance to make sure we will have access to high speed internet. Lower Wi-Fi speeds or strength means that work just takes longer… and that decreases our productivity significantly. We don’t have a great tool for Wi-Fi research just yet, but typically we scan cellular maps, read Campendium.com reviews, and ask other fellow digital nomads for tips on the best signal. If all else fails, we go there and test it out, and move on if it doesn’t work for us!

Challenges to the Digital Nomad Lifestyle

There are definitely drawbacks to this lifestyle, and there will be times when you’ll find yourself scrambling for ways to continue. There will also be plenty of things that will test you in your journey.

When you’re feeling lost or lonely, here are some things you can do.

Find Your Community

Remote living can be lonely. Traveling seems exciting but being on the road without a stable community can take its toll. We find that we like to spend time with family and friends frequently, and plan that into our schedule. We also seek out other full-time RVers and digital nomads to meet up with on the road and share stories, knowledge and companionship. It really helps motivate us and keeps us from being hermits!

Find Your Supporters

A part of starting any new venture is dealing with naysayers. For many reasons, there will be people in your life that don’t support your business or your lifestyle. And that’s ok – but it’s not their life. When we’re having a challenging day (or week!), we surround ourselves with our top cheerleaders, or other digital nomads who understand our lifestyle. We make it a point to follow up frequently with our network of supporters across the world – this community is so important!

Why We Won’t Stop RVing Anytime Soon

Traveling in an RV is one of the absolute best ways to see our incredible country (and others!) as well as reconnect with nature. I truly believe that the more people connect with nature, the better off both humans and the Earth will be. Nature has been proven to reduce stress, lower blood pressure, boost the immune system, and increase energy, among other benefits. The most palpable benefit to the Earth itself is the realization that many people get when they spend time outdoors: this incredible planet is diverse beyond imagination with animal and plant life, and we need to be fiercely protecting it!

The digital nomad lifestyle has crushed the misconception that you have to be glued to your cubicle to get work done and earn a living. The ride may not be easy – but if you’re driven with passion and dedication, it’ll be 100% worth it!