South Africa 2020

I can’t wait to travel South Africa with you. It’s one of my favorite countries in the world. Below are some more details. If you’re interested, apply here.


The Weekend Briefing community is comprised of some really impressive, thoughtful and engaged leaders across all industries. As the community has grown over the last five years, I’ve wanted to create a truly meaningful in-person experience for the community. I’ve thought about a conference, but seriously… who needs another conference? During my recent trip through the American South, we focused on race and justice. I was struck by how much I learned and grew. Additionally, how our group grew together through this shared experience. I discussed this with my friend, Greg Kahlil, who runs Illumine and we decided that a South Africa trip to connect with Anti-Apartheid veterans and young entrepreneurs shaping the future of the nation would be the perfect experience for the Weekend Briefing community. Apply


We will explore Apartheid and learn how a wide range of cultural and business leaders address the seemingly intractable issues South Africa still faces today. We’ll be meeting with veterans of the anti-Apartheid movement, young entrepreneurs, key social and political leaders of all background who are committed to building a just society today.  We’ll enjoy unique access to historic sites in Johannesburg and Cape Town (one of my favorite cities in the world), off the beaten-path locations, world-class cuisine, wine and rich culture. We’ll engage with South African change agents in thought-provoking settings. Join us on a once-in-a-lifetime opportunity to explore and be inspired by South Africa. Apply


Maybe you. We want the trip to be intimate, so we’re capping the group size at 15. We’re trying to curate an intelligent, fun and engaged group of people. If you fit the bill, please apply. Apply

How Much

The trip will be around $6,000 for a week, not including air fare. We’ll nail down the price once we finalize the group. We may also add an optional safari for those who are interested. Apply


The trip will take place in February 2020, we’ll nail down the exact dates once the group is confirmed. Apply