Jon Callaghan is a serial founder-turned-VC who started his first company, a mountain bike shop in Jackson Hole, at 18 and ran it for eight years, giving him deep empathy for founders through having literally swept floors and managed cash as an operator. He has a distinctive philosophy of maximizing risk at the earliest stages, explicitly wanting to take extreme product, market, and timing risk by backing founders before clear markets exist, and is known for backing category-defining companies well before their categories existed, like Fitbit when it looked like a pedometer in a world with no wearables market. Jon Callaghan is a serial founder-turned-VC who started his first company, a mountain bike shop in Jackson Hole, at 18 and ran it for eight years, giving him deep empathy for founders through having literally swept floors and managed cash as an operator. He has a distinctive philosophy of maximizing risk at the earliest stages, explicitly wanting to take extreme product, market, and timing risk by backing founders before clear markets exist, and is known for backing category-defining companies well before their categories existed, like Fitbit when it looked like a pedometer in a world with no wearables market.