The Raw Truth About Entrepreneurship – and How to Stay Motivated

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The Raw Truth About Entrepreneurship – and How to Stay Motivated


Hi! I’m Julie Singh, Co-Founder of My husband Reet and I started TripOutside out of a shared enthusiasm for outdoor adventure and travel. We are passionate about exploring this incredible world on our bikes, kayaks and skis. After many frustrating experiences wasting valuable vacation time renting equipment, we decided to create a website that allows others to easily book gear for their adventures online, saving them time and effort and letting them enjoy more of their vacation time. We are woman and minority owned, with over 20 combined years of experience in retail, finance and technology at a fortune 30 company. We left our corporate careers 2 years ago in pursuit of our passions. TripOutside is a fully mobile company – we gather information on the best outdoor destinations for our customers by exploring the country in our motorhome with our cat Juke.

What Differentiates
TripOutside is a new website for outdoor enthusiasts who want to book outdoor gear and adventures online from the best local shops. The site allows customers to discover top outdoor destinations, compare rental prices, and book the gear they need online quickly and easily. The site features shops that rent bikes, kayaks, stand up paddleboards, canoes, skis, snowboards, rafts, surfboards, camping gear and more. features outdoor gear and adventures for the outdoor enthusiast. We strive to tread lightly on our extraordinary planet and we feature only “silent sports” – gear and adventures that leave no trace. We focus primarily on gear rental for “DIY” adventures, but we also feature some awesome guided trips like whitewater rafting and backcountry paddling tours. We curate our outfitters and adventures to make sure we are only featuring the best local shops.

Many other travel sites exist where customers can book a broad variety of experiences – everything from museum visits to guided city tours. You won’t find museum visits, walking tours or ATV rentals on We focus on a smaller outdoor adventure niche, but everything on our site is relevant to the outdoor enthusiast. Our goal is to get more people out and exploring our magnificent wild places! works with gear rental shops of all sizes, whether they have an existing online booking software or not! We can integrate with many different booking software or send them booking requests using our custom-built tool. We provide an additional marketing channel to help shops rent unused equipment while saving them time and effort in the shop.

My Favorite Aspect of Being an Entrepreneur
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. But it also requires a TON of discipline, because with flexibility comes the need to evaluate and structure for success. I love being able to look at my most precious asset, my time, and decide where I’m going to spend it. I believe this is also the biggest difference between entrepreneurs and those who work for someone else. Having spent 15 years in Corporate America, I see the biggest difference is the true autonomy of entrepreneurship that requires a ridiculous amount of discipline, motivation and tenacity.

Sacrifices of Entrepreneurship
This leads me to the sacrifices. There isn’t a day that goes by that I’m not thinking about the business, strategizing, brainstorming, planning and executing. It’s hard to step away from it, it truly is my baby. 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 our business (and the reason we started an outdoor adventure business) is that it also allows us to get out and experience the destinations we are featuring. We focus on curating many of the local shops and outdoor activities we feature for 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 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!

Business Advice for New Entrepreneurs
The Obstacle is the Way (another 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!

My Favorite Book that Helped Motivate Us to Start a Business
The Code of the Extraordinary Mind is a really great book that I read just before we started I came across it at just the right time – it helped me to challenge my status quo, redefine my idea of success, and make some drastic changes to pursue my passions. It encouraged me to move beyond traditional ways of thinking and redesign my life on my own terms. It’s worth the read!

Contact Details: Email, Social Media, Logo/Photos
Instagram: @trip.outside (
Facebook: tripoutside (


Positive Phil Podcast
About the Author
Positive Phil is a motivational keynote speaker & start-up consultant. Focusing on revenue generation & new business acquisitions. Founder & CEO @Audio inc. Business developer since age 12. Public Company Start up CEO, $investor -Public speaker #podcaster #motivator Enjoying life.

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