By Dave Hassell, an EO San Francisco member and founder of 15Five, an employee communication software company.
It was 8 June 2011, and I was working on a new product called “15Five”— employee communication software based on an idea that allowed Patagonia founder Yvon Chouinard to take half of each year off to climb mountains and surf, all while in the midst of growing a wildly successful multinational company. Yvon’s story inspired me. I immediately called three of my closest EO buddies and said,
“Sign up for kiteboarding lessons. We’re going to Brazil!” I decided to put together a trip that combined my love of kiteboarding with my love of connecting. The idea was to get a group of amazing entrepreneurs together to spend 10 days downwinding along the Brazilian coastline, creating new connections, sharing ideas and having fun.
But a week later, reality struck. What was I thinking? I was bootstrapping my new company and working 100 hours per week how could I possibly take time off? I called my EO friends and told them that the trip was off. Thankfully, they wouldn’t let me off the hook, saying I was thinking about it all wrong. What was the worst that could happen? Wasn’t I building a product that was supposed to allow CEOs to do this very thing? They had a point.