In 2006, the authors started a discussion about St. Cloud State University Outdoor Endeavors working together to run a trip in the Everglades National Park. The following summer they began the planning process through phone conversations, email and division of tasks. Despite the physical distance and separate university systems, each with their own unique approaches to business, the authors developed a collaboration that is successful. This success manifested itself in a relatively flawless week of sea kayaking in the Gulf of Mexico this past January. Many of the factors contributing to this success were things that both authors had learned from their involvement in their own outdoor leadership training. Key factors in the success of this joint venture included a certain level of trust, defining roles and responsibilities, identifying potential breakdowns in the process and what their individual expectations were for each other.