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.
What I didn’t expect the first time was how much the culture would affect me off the mountain. Japan runs on a different set of values. Precision. Craft. Long-term thinking. You see it in the food, the trains, the way strangers interact with each other. I always come back with something I can’t quite name, but it shows up in my work for months afterward.
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.
There’s no cell service on the game drives. No Slack. No email. Just the guide, the vehicle, and whatever is on the other side of the bush. I didn’t realize how much mental noise I was carrying until it went silent. By day two I was sleeping better than I had in years.
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.
Buenos Aires specifically has a pace to it that I find genuinely restorative. Late dinners. Long conversations. A city that doesn’t seem to be in a rush even when it’s fully alive. Working there feels different from working in New York or Miami. Something about the environment changes how I think about long-term bets.
How I Travel
A few things I’ve learned from years of traveling as an entrepreneur.
No work on the first full day. I used to arrive and immediately check in. Now I give myself at least one day to actually arrive before the laptop comes out. The transition is worth it.
Bring a notebook, not just a phone. There’s something about writing by hand in a new place that surfaces ideas I don’t access at a desk. I have years of notebooks filled with things I figured out somewhere I’d never been before.
Travel with people who challenge you. The conversations are the point. The destination just creates the context.
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.