Ajay Goel, successful entrepreneur who built and sold Jangomail, talks about the pitfalls of bootstrapping, the strategic decisions that differentiate big wins from huge wins, and his new business GMass. They discuss the limitations of sending emails through Gmail accounts, the success of GMass, and the challenges of building a lasting impact. Other topics include their hiring philosophy, balancing independence and impact, handling customer support, and reflecting on challenges of Gmail-dependent business.