How We Created a Remote Company That Gives Us the Flexibility We Want Out of Life (Julie Singh’s Story)

This post is brought to you by an essential piece of equipment for Julie to work remotely: an unlimited hotspot.

This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!

Julie and her husband Reet left the corporate world in 2017 for a life spent outside. They found a way to turn their passions into a remote company – a strategy we see is often the key to happiness and success as a digital nomad.

Thank you for being here with Freedom Is Everything, Julie!

Key takeaways from Julie’s interview:

“I love being able to look at my most precious asset – my time – and decide where I’m going to spend it. But it also requires a TON of discipline because with flexibility comes the need to evaluate and structure for success.”

“Don’t shy away from the challenging areas of your business – this is probably why you started the business to begin with! The obstacles are usually where the big “aha!” moments come from and where you can make the most difference. It will not always be easy, but that’s also why it probably hasn’t been done before. Have confidence in yourself and your ability to figure it out!”

“We love video – it’s truly a lifesaver in the remote work world. For training and communication that requires more than a quick note, we create videos. Tools like Loom allow you to record and share videos with both voice and screen sharing to show your desktop and exactly what you are working on. We love video for explaining new projects, providing feedback on documents/deliverables, training our team on processes, and showing them how to use various tools and software.”

Introduce yourself! 🙂 Who are you? What do you do for work? And what is your nomadic story?

Julie and Reet from TripOutside smile while hiking with a lush field and mountain behind them

Hi! I’m Julie Singh. My husband Reet and I left our corporate careers in 2017 and hit the road in our RV with our cat Juke to explore the outdoors and start our company TripOutside.com. We have a shared enthusiasm for outdoor adventure and travel, and we are passionate about exploring this incredible world on our bikes, kayaks, and skis.  

TripOutside allows outdoor enthusiasts to discover top outdoor destinations, compare prices on gear rentals, lessons, and tours, and book their gear or adventure online quickly and easily. 

What inspired you to start nomading? And how has nomading changed your perspective on life?

My husband and I have always spent our free time traveling and adventuring outdoors. When we lived in a “brick and mortar” home, we traveled on weekends and vacations and spent most of our free time biking, hiking, kayaking, and snowboarding. We wanted to be able to travel more, follow our passion for the outdoors and start a business. We debated traveling overseas but had two cats that we wanted to be able to bring with us. At that point, we had a small van that we took on our camping trips and realized that we could travel full-time in an RV, bring our cats, and start an outdoor business.

Being a “digital nomad,” and particularly an entrepreneur 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. I love being able to look at my most precious asset – my time – and decide where I’m going to spend it. But it also requires a TON of discipline because with flexibility comes the need to evaluate and structure for success.  

Our company, Trip Outside, has a mission to get people outdoors and adventuring. It only makes sense that we travel full-time, and our office is the outdoors. It is in our business blood to be nomads! We also want all of our employees and contractors to also be able to live and work where they want to, hopefully near outdoor adventure!

Please tell us the detailed story of how you started your business. 

Julie and Reet Singh stand in a slot canyon one foot on each side while one leans to the right and the other leans to the left

We love outdoor adventures and are avid bikers, paddlers, and snowboarders. We always took vacations to spend time doing what we loved but yearned to be able to get outdoors more. While on vacation, we saw an opportunity to create a platform to find and book outdoor adventures from the best local shops, guides and outfitters. This turned into our website TripOutside.com, which allowed us to leave the corporate world and become entrepreneurs. We love our new lifestyle, and starting TripOutside has allowed us to be able to travel more and work from anywhere (we are completely digital and work from wherever our RV takes us!). 

Since launching, what has been most effective to acquire/retain customers and scale your business?

We’ve been full-time RVing since 2017, and it has truly been one of the most important pieces of learning from our outfitters and customers and developing strong partnerships. Meeting our outfitters face to face has been invaluable, and the opportunity to explore in the destinations we feature has helped in so many ways – from content to customer feedback.

Because we are a marketplace, we have to focus on both customers (demand) and outfitters (supply). If there are not enough outfitters on the platform, it’s hard to get customers. Without enough customers on the platform, it’s hard to get outfitters. So, in the beginning, we chose to start with the supply side because we needed a decent amount of activities on our site for customers to choose from. We launched in 2018 with ~75 outfitters in 25 top outdoor destinations, and we’ve been relentlessly growing ever since!

We are focusing first on three key activities: biking, kayak/SUP, and ski/snowboard. Then we focus on the top destinations for these activities and make sure we have the best local outfitters and activity providers on our platform for our users.

The great thing about TripOutside is that outfitters and activity providers don’t pay anything until we get them a booking – so it’s risk-free, and we only make money if they make money. That makes it a no-brainer for many outfitters, but our first 100 did give us their vote of confidence before we even launched, so we give them extra-special treatment whenever we can.

What advice would you give to someone who’s thinking about nomading?

Julie Singh's RV parked in Taos, New Mexico in the snow with other RVs parked near it

Remote living can be lonely. 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!

Don’t go too fast! We spent the first year flying around the country, trying to see as much as we could but only scratching the surface everywhere we went. After that, we slowed down, and now we spend a few weeks at minimum in each place to be able to really discover it, and we allow ourselves lots of time to stop places spontaneously along the way that we come across.

Having a strong (4G/5G 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. We have both Verizon and AT&T unlimited hotspots, so we have the best chance of getting a signal. Lower Wi-Fi speeds or strength means that work just takes longer… and that decreases our productivity significantly. There are places we just can’t visit (or can’t visit for long) because there isn’t any signal.

What are the 2-3 favorite places where you’ve lived/traveled to and why?

Julie and Reet Singh sit atop a rock with their small dog smiling at the camera with a multicolored sunset in the background

Idaho and New Mexico are two hidden gems (shhhh…) that we really love. The incredible outdoor adventures, remote and untouched wilderness areas, hot springs, and lack of crowds really make these two states special places that we keep going back to.

We also travel to India every year to visit family and explore the many spectacular places around the country. It is such an incredibly diverse country with so much to see, we feel like we could never run out of places to visit. We love it all – the colors, the people, the food, the history, and the adventures.

For someone interested in becoming an entrepreneur in your field, what’s the best advice you would give? And what books, podcasts, thought leaders, or other learning resources do you recommend?

Julie sits in a blue kayak on a lake while Reet stands on a red stand-up paddboard

  • There will be plenty of things that will test you in your journey. Being an entrepreneur is one of the hardest things we’ve ever done! However, if you are truly passionate about your venture, great things will come – we truly believe this!  
  • Build up your network and have regular conversations with your biggest supporters. This will provide you with the inspiration you need to get over the tough times.
  • Don’t shy away from the challenging areas of your business – this is probably why you started the business to begin with! The obstacles are usually where the big “aha!” moments come from and where you can make the most difference. It will not always be easy, but that’s also why it probably hasn’t been done before. Have confidence in yourself and your ability to figure it out!
  • We love the How I Build This podcast – it features entrepreneurs and their stories of how they build their companies, and it’s so inspiring to hear about their challenges and how they succeeded in building great companies.

What digital tools do you use for your work/business?

Online Tools
Because TripOutside and our team is fully remote, we communicate 100% through digital tools like email, What’s App, and other chat messaging apps like Upwork messaging for our contractors. We use these avenues for short, quick communications like sending documents and links and answering questions. Online chat, in particular, is really great for quick questions and messages that don’t require training or in-depth explanations.

To share documents among our team members, we use Google Drive and Google Docs and assign permissions accordingly. Google Docs is great because our team can access and edit the same documents we are using, and we can add instructions and review completed work.

Project Management
We have used many different project management software to communicate with our team and stay on top of timelines and deliverables. Our favorite so far is Trello. They have a free version with shared boards that let you track projects, comments, status, add attachments and videos, etc. It also includes email notifications, so you know when comments have been added and boards edited.

Video
We love video – it’s truly a lifesaver in the remote work world. For training and communication that requires more than a quick note, we create videos. Tools like Loom allow you to record and share videos with both voice and screen sharing to show your desktop and exactly what you are working on. We love video for explaining new projects, providing feedback on documents/deliverables, training our team on processes, and showing them how to use various tools and software.

What scale is your business at today, and what are your future goals?

Julie and Reet Singh stand in front on an alpine lake on a sunny day with sparse trees and some higher mountain peaks behind them

We had 8K monthly users on our site as of last month, who could choose from over 400 adventures in almost 200 outdoor destinations, and we are growing fast. We are still a startup and focused on growth, so we are reinvesting everything back into our business.  

We are adding new outfitters to the platform every day and plan to expand to all of the top outdoor destinations in North America and then expand internationally.

If you only had a few minutes to live, what are the most important life lessons you would share with the world?

Focus on giving instead of taking. Not only does it feel so much better, you will receive more than you can imagine.

What do you travel with that you couldn’t imagine traveling without?

Julie and Reet's cat named Juke lays in the window of the couple's RV

Our cat Juke – he’s sitting on my lap as I’m typing (yes, it’s kind of awkward, but I love it). **Just make sure your cat is ok with RV-life before you just dump them in it – we did lots of trial runs first!**

How can people learn more about you and your work?

https://www.tripoutside.com

https://www.instagram.com/trip.outside

 

Lauren Allain
Lauren is a freelance journalist from Seattle. She travels the globe in search of the best grocery stores, bouldering gyms, and snorkeling locations. Her mission at Freedom Is Everything is to help others make the transition into location-independent lifestyles.