“We had a chain drive there which just didn’t work,” Willner says. “Twenty-knot winds, we’re in six-foot swells and we’re just being carried up the Channel, and no rudder, and the chain drive’s broken. We had to be rescued and towed back in before a ferry hit us. So it was a good time!” 

This kind of unflappability, which you can see in a video from that soggy day, has come with experience. Willner has had enough success in his professional life to write an entrepreneurial guidebook — he co-founded ObjectArts, a leading technical training company for Microsoft (“That was back in the late ‘90s when Bill Gates used to show up to do training himself when we were doing sessions.”), and is now the CEO of luxury tourism company Travel Edge — and while some of that go-getter spirit readily translates into ill-advised drives to the most remote corners of the world, it’s his real-world overland résumé that counts. 

To read the full interview with Jeff click here.