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
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
