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Matt Oesterle has a diverse work experience spanning over two decades. Matt is the Founder and CEO of Ramble, a company aimed at providing exceptional camping experiences across the US. Prior to Ramble, Matt was a Member of The Explorers Club starting in 2023. Matt also co-founded Callisto Media in 2011, where they served as the Chief Strategy Officer, focusing on using data and technology to deliver customer-centric content. Before that, Matt founded and operated multiple companies, including a college laundry delivery business, a search engine for local events, and an email marketing company. Although the latter ventures did not achieve significant market adoption, they served as valuable learning experiences for him.

Matt Oesterle obtained a Bachelor of Science (BS) degree in Economics, along with a major in the Markets and Management Program from Duke University, between the years 2001 and 2005. Additionally, they participated in the Bargaining and Negotiation Program at The London School of Economics and Political Science (LSE) during the year 2004.