My Top Travel Destinations

July 30, 2025

For entrepreneurs and investors, a vacation is rarely just a vacation. It’s a chance to disconnect, gain a new perspective, and recharge for the next big push.

I travel a lot, both for work and for adventure. While every trip is unique, there are a few places I return to or that have left an indelible mark.

Here are three destinations that offer the perfect blend of work, inspiration, and escape.

Table of Contents

Japan

Every year, I head to Niseko in Japan to snowboard. It’s a non-negotiable trip that serves as a physical and mental reset.

It’s my annual pilgrimage for pure, exhilarating fun with other entrepreneur friends.

Snowboarding

South Africa

My trip to the Sabi Sabi private game reserve in South Africa was truly incredible.

Spending days on a safari, completely disconnected from the digital world and immersed in nature, is a powerful experience.

Argentina

I travel to Argentina multiple times a year, as it’s home to my tech team. While it’s a work trip, it’s also an opportunity to immerse myself in the vibrant culture of Buenos Aires.

Many of my favorite destinations have become venues for Outcove, where I bring together entrepreneurs for transformative experiences.

Blending strategic work sessions with exploring a different way of life provides a unique kind of energy and inspiration that you can’t get from a Zoom call.

Walking around

Conclusion

Travel, whether it’s for adventure, work, or relaxation, is a crucial investment in yourself.

It breaks routines, sparks new ideas, and provides the perspective needed to tackle big challenges.