Jason Westlake: on Adventure, Entrepreneurship & Building a Life on Your Terms episode artwork

EPISODE · Sep 2, 2026 · 57 MIN

Jason Westlake: on Adventure, Entrepreneurship & Building a Life on Your Terms

from Lets Have This Conversation · host Kevin McShan

Workplace and leadership surveys show an overwhelming consensus among business leaders regarding the importance of team connection: ·         90% of employers state that fostering a sense of community and connection at work is crucial for business success. ·         71% of executives believe that strong employee engagement—often built through shared goals and team activities—is a core driver of their company's success. ·         47% of executives explicitly invest in employee experience initiatives to improve team collaboration. According to Harvard Business School and workplace satisfaction and engagement surveys, these statistics reinforce an essential reality: human connection, engagement, shared purpose, and collaboration are fundamental ingredients for organizational success. But what happens when those same principles are taken far beyond the traditional workplace—and into the Costa Rican jungle? Jason Westlake is an entrepreneur, adventure travel leader, author of Jungle Whispering, and co-owner of Tierra de Sueños Retreat & Wellness Center in Costa Rica. For 17 years, Jason has guided people toward unforgettable experiences while building a business and lifestyle centered on adventure, connection, courage, and community. The retreat center has hosted more than 267 retreats, supported by a diverse team committed to giving guests an uplifting and memorable experience. Jason's own adventures have taken him far beyond the familiar. From kayaking with killer whales and tracking gorillas in Africa to living deep in the Amazon with Indigenous communities, wrestling anacondas, and coming face-to-face with jaguars, his experiences have reinforced a powerful lesson: some of life's greatest opportunities begin just outside our comfort zones. At Tierra de Sueños, that philosophy extends to the entire guest experience. Nestled in the jungle near Playa Chiquita and Puerto Viejo, the retreat brings together different cultures, languages, locally sourced food, yoga, nature, adventure, and community. Behind it all is a team dedicated to helping visitors experience Costa Rica in an authentic and unforgettable way. In this episode of Let's Have This Conversation, Jason and I explore what happens when business and adventure become partners rather than competitors. We discuss overcoming fear, stepping beyond comfort zones, creating strong teams, building a business that supports the life you actually want to live, embracing cultural experiences, and designing once-in-a-lifetime moments people never forget. How much of the life we want exists just beyond the boundaries we've created for ourselves? And can entrepreneurial success be measured not only by what we build—but by the freedom, connection, adventure, and memories we're able to create along the way? Join us for a conversation about business, adventure, courage, human connection, and what it truly means to build a life on your own terms.   For more information: https://tierradesuenoslodge.com/ Email: [email protected] Get the Book: https://www.amazon.ca/Jungle-Whispering-Influence-Jason-Westlake-ebook/dp/B01IANR5ZG/ref=sr_1_7?dib=eyJ2IjoiMSJ9.2WamUAO73OQ4fMKQyx_3YDKABV0NO3kXVNLOO4KpyZwRDdyRePN_QL3w9w4WQEN3JAu0qf_Gy1Fit6Zli0ByVZgZkhZVSol-xG6D9Tt4x0iprcOV1QPyez_R-TZqel8M.-30SXJQvWeXo_P3i8h8uy1zuhz6mMmlv6Ip9Q-j2PU0&dib_tag=se&qid=1788369657&refinements=p_27%3AJason+Westlake&s=digital-text&sr=1-7&text=Jason+Westlake Learn more about your ad choices. Visit megaphone.fm/adchoices

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Jason Westlake: on Adventure, Entrepreneurship & Building a Life on Your Terms

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