Most people facing unemployment at the age of 50 would turn towards the safety and comfort of what they know to get back on their feet. When Henry Gold was in that position, he decided to lead a four month bicycle expedition from Cairo, Egypt to Cape Town, South Africa and organize a race on the same route despite having never bike toured or raced a day in his life at that point. Gold thought his adventure was going to be a one-time thing. Instead, it gave launch to his bike touring company, Tour D’Afrique. Twelve years on, the company offers 10 expeditions and races on six continents. I spoke to Gold about his history working with NGOs around the world, the African bike-manufacturing project he tried to start that helped inspire Tour D’Afrique, the joy and challenges of leading multi-month bike expeditions, and much more.