Intro:
Rob Little, former CEO and Co-Founder of Cairn—a discovery platform founded in 2014 and acquired by Outside Magazine in 2021—joins Bending Rules to share his journey into entrepreneurship and the eventual founding of Cairn. As one might expect, the path wasn’t linear. Once an aeronautical engineer with Lockheed Martin and a newly minted graduate of the University of Pennsylvania’s Wharton School (MBA), Rob had numerous options. However, he chose to venture across the country to the northwest and pursue the entrepreneurial path, co-founding Cairn, a company that eventually connected thousands of outdoor enthusiasts to the latest and greatest brands and products in the outdoor industry. Cairn’s subscription platform seeded approximately 34 million products for more than 300 partners and introduced new brands and products to over 75,000 highly qualified enthusiasts throughout the life of the business. As one might expect, I was curious how Rob’s background as an aeronautical engineer benefited him in running a consumer product company. His journey is layered with great tactical advice for entrepreneurs, including reflections on cultural dynamics during growth and contraction, which I found particularly interesting. I left our conversation with the feeling that Rob has another start-up in him. Understanding, of course, the “all-in” aspect of that decision, he’s taking his time with family and friends—perhaps the greatest reward of the journey.
This will be our last episode for 2024, marking the culmination of the first year for the Bending Rules Podcast. I hope folks enjoyed and benefited from these stories. We look forward to continuing to share the stories of entrepreneurs in 2025, and with several great guests already on the calendar, it should be another year of insights and growth.
2:19 -- Rob's background and life prior to entrepreneurship
8:54 -- Shifting from aeronautical engineering to the tought of running an outdoor products company
15:05 -- Wharton School of Business: Opportunity Cost vs. Entrepreneurial Conviction
21:56 -- Data Driven Decision and how engineering background helped inform decision to scale and grow the company
34:07 -- Roller Coaster ride of entrepreneurism
37:39 -- Wild West of Facebook Advertising
44:20 -- Acquisition: challenges and opportunities
53:04 -- Reflections and possible future directions
