Samrat, 27 years old, was a technological entrepreneur in the field of wireless and communications technology. He started his own technology company when he was 23 years old. As a fresh graduate in electrical engineering, he preferred to set up his own company than to choose the other mainstream options of taking up a job, or an MBA degree or pursuing higher education. I was led to him through my search for forums that support young entrepreneurs. In my first interaction with him over the phone when I told him that I would be interested in studying what factors could have encouraged him to take this risk, he promptly responded that he did not think that it was a risky decision to have a start-up. He wanted to do it, and if it had not materialised, he would have gone on to take up a job. His self-assurance set the tone for our interactions, and in the subsequent meetings, I explored his motivations, attitudes, approach towards work life along with his growth process and life contexts.