Starting a Business at the Intersection of Passion and Opportunity

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Rob Little packaged his passion for the outdoors and a desire to build a company into a monthly subscription box that is changing the way outdoor enthusiasts interact with some of their favorite (and soon to be favorite) brands.



Starting a business has many parallels with an arduous backpacking trip: The expedition can be long and daunting; there will be unexpected hardships; ambition, resilience, and resourcefulness are requisites; and yet the journey itself, in all of its beauty and challenge, is a priceless opportunity to grow and experience the world in a new way.

Today, we feature Rob Little, the Founder of Cairn, a curated monthly subscription box catered to outdoors enthusiasts, featuring new brands and products in the outdoor and recreational industry. We were excited to chat with Rob to learn more about starting a business at the intersection of opportunity and passion.



For the love of the outdoors

Rob’s passion for nature started at the boundaries of his backyard, growing up amidst the mountains of Oregon. After graduating college, he spent nearly 3-years working as an engineer in the Peace Corps, where he admitted he spent “all of my free time backpacking and exploring rural parts of Central/South America.” Rob returned stateside with a love for exploration, a refined appreciation for nature, and a driving desire to start a business.

Read on to hear what it takes to launch and grow a company, and hear some of his lessons learned in being a first time entrepreneur:


How did you get started with Cairn? 

"While in business school I was amazed at the number of times I ran across examples of disruption in the retail industry. The number of businesses that are changing how consumers find and purchase products is extensive, but few – if any of them – were in the outdoor industry. This intrigued me, and I started to build a model for a new distribution method in the industry.

I saw an opportunity to inspire and equip outdoor enthusiasts through a monthly box, as well as an opportunity to allow brands a channel to increase exposure for new products and collect feedback on those products. After talking with consumes and brands, I was encouraged that the model could work and launched the business in the Spring of 2014."


There are many subscription type services out there, what gave you confidence that the outdoor enthusiast needed a monthly box?

"Many people who love the outdoors also love gear. A monthly adventure/discovery box is a great fit for this industry. Consumers can have someone else curate the latest and greatest content, package it into a fun present, and deliver it to their doorstep once a month. The most common piece of feedback we get from our subscribers is, 'It’s like Christmas, once a month!'”



Starting a company can be daunting, what steps did you take in the beginning when starting the business?

  • Break it down: "I took small steps and adjusted as I learned throughout the process. Initially, validation of the idea was important. I spent several days at the 2014 Winter Outdoor Retailer tradeshow, talking to brands about content and their interest in our model. When it was apparent that there was an opportunity, I launched a site and started to bring in customers organically."
  • Test and iterate: "After going through the cycle several times of curating content, delivering it to consumers, and collecting feedback for the brands, we knew we had a process that worked but that needed to be refined to scale. That’s when we revisited and improved each piece of the business: from our website, to our packaging and logo, to the data analysis that we do."



What have been some of the most important and memorable points in your journey so far? 

"Watching the growth of the company has been the most memorable part: First you’re shooting for 100 boxes, then 500 boxes, then 1000 boxes. With each step it seems like the next is so far away.  Yet, before you know it you’re there."


Have there been any hardships? How did you overcome these?

"The biggest hardship is keeping all of the various parts of the business in motion simultaneously. Take into consideration the core of the business: Our boxes. At any given time we are curated content for future boxes, shipping the current month’s box, and reviewing and providing feedback to the brands on past month’s boxes.  

Each of those areas has a variety of variables and complexities. Combine it with the day-to-day operations of running a business (e.g., legal documentation, accounting, building a team, etc.) and it’s a challenge to do them all well. The most effective thing that we’ve done to help control all the moving parts is to plan ahead. We have schedules in each area that we execute to – without the constant reminder our calendars bring, we’d fall behind somewhere."


What has been your biggest lesson learned in building the company?

"We took it slow for the first few months, that was the best thing we could have done – and a good reason we’ve been successful as we turn on the gas. Those first few months are critical to validating the model, listening to customers, and establishing a rhythm."


What advice do you have for other people in starting their own business (or project or initiative)?

"It’s easy to get intimidated by thinking about everything that goes into starting a business (or whatever audacious goal one has). My approach is not to think about the complexities of the big picture, but rather the complexities of the next step to get to the finish line.  

If you break it into small, manageable pieces, then it’s much easier to focus and execute. How does that phrase go?... 'How do you swallow an elephant? One bite at a time.'”


What’s next for you? What can the CogniTea community help you with?

"We have a lot of ideas that we hope to introduce into the outdoor industry on how to change how brands interact with consumers. However, our first step is to knock the subscription box out of the park, and then tackle some of the other goals.  It will take time, but we’re moving in that direction.

We love feedback on what we’re doing.  Positive or negative, we’d love to hear from anyone who has thoughts on our business, how we’re doing it, or what we’re missing. We’d love to hear from any of you. You can reach out to us at"

You can also find cairn online, on Facebook, and Twitter.



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