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“From Avocation To Vocation: How I Turned My Hobby Into A Career” With Julie Singh of TripOutside.com

…I love this question! 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 […]


…I love this question! 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! We have a unique opportunity to join the movement away from purchasing, consuming and littering our Earth and towards preserving our planet’s natural places and extraordinary biodiversity. We need to realize that our Earth can only take so much. Let’s join hands with our Mother Earth in the best partnership that could ever exist.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Julie Singh. Julie founded TripOutside.com with her husband Reet out of a shared enthusiasm for outdoor adventure and travel. They are passionate about exploring this incredible world on their bikes, kayaks and snowboards. After many frustrating experiences wasting valuable vacation time renting equipment, they decided to create a website that allows others to easily book gear and adventures online, saving them time and effort and letting them enjoy more of their vacation time. It is a woman and minority owned company, with over 20 combined years of experience in retail, finance and technology at a fortune 30 company. They left their corporate careers in 2017 in pursuit of their passions. Julie and Reet gather information on the best outdoor destinations for their customers by exploring the continent in their motor home with their cat Juke.


Thank you so much for doing this with us Julie! Can you tell us a bit about your “childhood backstory”?

As a kid, my sisters and I were always starting our own companies. I think our first project was collecting rocks in the alley behind our house and selling them to the neighbors. When my mom found out what we were doing, she told us we couldn’t sell plain rocks that they could collect themselves — we needed to add something to them in order to provide value to our customers. She suggested painting them, so that’s what we did. We painted little shapes and animals on the rocks and took our business to another level when we went door to door with them. We loved playing outside, and the combination of playing outside and making money was so appealing, even back when I was 5!

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

The idea for TripOutside came about on one of our vacations. My husband Reet and I both had Corporate careers but traveled a lot in our free time and spent as much time outdoors as we could. We rented gear like bikes, kayaks and snowboards during our adventures and saw a problem to be solved with online gear rental. We wasted too much of our vacation time renting equipment! The typical process involved online searches, calling shops about availability, booking over the phone, and waiting for bikes, skis or kayaks to be prepared in-store.

So, we created TripOutside.com to allow outdoor enthusiasts to compare prices and book outdoor gear and adventures on one website, saving them time and effort and getting them to their adventure faster. Our goal is to get more people outside and adventuring!

We left our Corporate careers in 2017 to start TripOutside, and we travel full-time in our motor home (with our cat Juke!) curating the best outdoor destinations for our customers. To be able to start our own company based on passion of outdoor adventure has been absolutely incredible! Entrepreneurship is definitely challenging, but we are so passionate about what we do, and we love our work!

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

That’s funny that you mention this — it’s a fantastic question. My husband Reet is a serial business idea generator. He maintains a list of hundreds of business ideas in his phone and adds to it constantly. I think the reason TripOutside stuck is that it is our passion. Once you stumble upon the idea in which you can combine what you love and making money, it becomes so much easier to execute it and turn it into an actual business. It hasn’t been without its challenges, but it’s so much easier to stick it out when it’s something you are truly passionate about.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

A really great way to turn a hobby or pastime into a business is to identify a pain point in the process, or a way to make things easier for others that enjoy this pastime. Start by doing your research to find out if others have this same pain point, and whether anyone else is solving it right now. Some of the best business ideas solve a pain point for customers, which translates into a very devoted and enthusiastic customer base (think free Marketing!). For example: if your hobby is chess (and let me preface this by saying I know nothing about chess), the pain point could be that people find it hard to learn chess, or that it’s hard to find places to play chess. You could develop a business around teaching people to play chess (in person, videos, online, etc.) or you could create your own chess boards with localized chess pieces (e.g. local attractions) and sell them to establishments all over the country to add to their “bar games” sections. There are so many ways to make money, just get creative and it will come to you!

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I think entrepreneurs can get bogged down in the details of the business and end up not truly getting to spend time doing what they love anymore. Most startups don’t have funds to hire people right off the bat, so everything that goes with starting the business falls into the lap of the founders. There isn’t a day that goes by that I’m not thinking about the business, strategizing, brainstorming, planning and executing. We are working most of our waking hours, and I think most entrepreneurs can relate. The never-ending feeling that there is more work to be done can be hard to deal with, especially when we are in incredible outdoor destinations!

The good part about starting a business around a hobby we are passionate about (and the reason we started an outdoor adventure business) is that it also allows us to get out and experience the outdoor destinations we are featuring. We need to be out talking to our customers and shops, experiencing our destinations, and pursuing our outdoor adventure passion. Not only do we curate many of the local shops and outdoor activities we feature, but getting outdoors helps us meet and engage with our customers.

We try to get outside and explore every day — even if it’s just a short hike — and plan a bigger adventure like mountain biking a few times a week. We make sure we visit with shops and customers everywhere we go and continue to learn from our outfitter partners and our customers. We are truly passionate about helping people get outdoors, and the conservation of our wild places — so that definitely helps. We also use nature and the outdoors to help us clear our heads, relieve stress, and get our creative juices flowing!

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

Being an entrepreneur, particularly a “digital nomad” 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.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

There will be plenty of things that will test you in your journey. Being an entrepreneur is one of the hardest things I’ve ever done! However, if you are truly passionate about your venture, great things will come — I truly believe this! Also, 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.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

It is challenging to know everything about starting a business, and hard to learn it all at once. We were naïve in the beginning and assumed that the contractors we hired for things like development and marketing would know how to do things better than us. We had a couple bad experiences, and we learned that we can’t hire someone to do work that we don’t fully understand. We have learned over time that we have to build at least a basic level of understanding of all aspects of our business to be able to guide our team on the strategy and communicate goals. Online training sites like Udemy and Linda.com have great training guides and resources for everything from marketing to finance to operations, and have helped us learn about topics that we didn’t have as much experience with. We also subscribe to various industry leaders for insights and tips on various subjects.

How have you used your success to make the world a better place?

We are passionate about outdoor conservation and making sure that our wild places are protected. We recently discovered the Conservation Alliance, a non-profit that focuses on protecting and restoring wild places for habitat and recreation. We are joining the Alliance and donating a portion of our proceeds to help fund their community-based campaigns to protect threatened wild habitat, particularly in places where outdoor enthusiasts recreate. Funds have saved more than 51 million acres of wildlands, protected over 3000 miles of rivers, stopped or removed 30 dams, designated 5 marine reserves and purchased 13 climbing areas. Whoohoo!!

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I love this question! 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! We have a unique opportunity to join the movement away from purchasing, consuming and littering our Earth and towards preserving our planet’s natural places and extraordinary biodiversity. We need to realize that our Earth can only take so much. Let’s join hands with our Mother Earth in the best partnership that could ever exist.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

The Obstacle is the Way is one of our favorite “life lesson” quotes, and also a great book we read recently! 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!

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

  • Rich Roll — we are also plant based athletes and listen to his podcast religiously!
  • Jane Goodall — her incredible work to protect the wildlife on this planet is an absolute inspiration to me.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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