He Left Silicon Valley to Run a Retreat in the Andes

He traded Silicon Valley for the Andes and built a life around a completely different definition of leadership. In this episode, I talk with Terry Cumes, CEO of Wilkatika Resorts in Peru's Sacred Valley and author of the new book Special Guests which explores leaving a career in education technology to run his family's wellness retreat full time. We dig into cross-cultural leadership, building community far from home, and why executive coaching and hospitality have more in common than people think. Key takeaways: - Why Terry unlearned much of his business school training to lead a Quechua-speaking team - What actually motivates loyalty in a multi-generational family business - How a strong sense of place supports deep personal work - The difference between clarity, authenticity, and vulnerability in leadership - Why "less efforting" can be a more powerful leadership tool than problem-solving - How intuition and analysis work together in high-stakes decisions - What it takes to build community after a major relocation Connect with Jason: https://www.linkedin.com/in/jasonbaumgarten/ Email the show here: jason@fithappens.fm 00:00 Intro to Fit Happens 00:18 Meet Terry Cumes, CEO of Wilkatika 00:46 Leaving Silicon Valley for Peru 02:32 Discovering his hospitality superpower 03:39 Leading a very different workforce 04:22 Unlearning business school lessons 05:13 What translated universally: loyalty 06:49 Building community far from home 09:17 Isolation and practical fixes 10:39 Using travel as an external stimulus 12:23 Why the Sacred Valley was chosen 14:10 What makes a guest transform quickly 15:34 Hospitality and the limits of delegation 17:57 Boundaries in an always-on culture 18:28 His yoga journey and its evolution 21:08 Yoga and mindfulness going mainstream 22:18 Blending intuition with analysis 23:29 How ceremony supports decision-making 25:04 Advice for skeptics of ritual 27:09 Taking the leap without overthinking 32:28 Building a legacy, not opting out 37:32 Bringing wellness retreats to business leaders 40:17 The value of showing up authentically 41:16 Clarity, authenticity, and vulnerability 48:38 Leadership advice that sounds right but isn't 50:23 Unlearning systems and embracing teamwork 52:02 Closing thoughts and where to find Terry