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IMG_7636 The week before TiEcon 2013, MentorCloud invited Sashi Chimala to talk about mentoring from his perspective as a successful long-time serial entrepreneur. Sashi has founded a wide variety of startups, including: Covansys, Indigo Technologies, Qwiky's Coffee Pub, cricket social network, and Knibble online gaming site, among others. He is now the CEO and Co-Founder at CrestPointe Corp., his new venture focusing on realtime data analytics.

Sashi started by talking about his mistakes - and how his lack of an early mentor demonstrated to him the benefit of learning from a business person who had been down the path already. Sashi believes in "paying it forward" himself - helping others to continue the passion. For him, it is fine to make one mistake but stupid to make that mistake a second time. Worse yet, he believes it is criminal letting others make the same mistake and not benefiting from your experience. He says mentoring is about mutual learning - both positive and negative. For Sashi, an entrepreneur is someone who sees a gap or opportunity - a problem not solved - and creates a business to solve it.

Sashi Chimala's first entrepreneurial venture was at the age of seven. He grew up in Andhra Pradesh, on India's southeastern coast, near a film studio. Sashi and his young friends would scavenge bits of film from studio trash, at first just to see pictures of their cinema heros. Later, they used the sun, a dark room, and a cloth wall to present short films to their friends, charging the tiny sum of a paisa (like a penny) per show.

Another early company started by Sashi took advantage of his talent as a cartoonist. While an undergraduate in Engineering at JNT University, he created a mail-order cartoon art school. The school was advertised in magazines, offering ten lessons by mail, with exercises critiqued by Sashi and a certificate of completion at the end. The school only ran for a year and served one hundred students (it took much more effort than he had thought) but lead to a profound experience.

Three years after Sashi closed down his cartooning school, when he was at a conference, a severely disabled man approached him. Although the man was impaired in all of his limbs and could only move with difficulty, he had diligently completed the cartooning school lessons and came to that conference specifically to thank Sashi for teaching him to be a successful cartoonist. Sashi never met his student or knew of his disability until that day. Sashi's only regret is that he wished he had saved his cartooning lesson material!

This remarkable conversation brought home to Sashi how entrepreneurship was not just about making money and having fun but could at the same time be an opportunity to help impact lives. That student showed him the purpose of business in a new dimension. Sashi knew from a young age that he wanted to be an entrepreneur and feel the power of starting something new but also to share his experiences: it made him feel good to teach and help others. It became second nature for Sashi to agree when asked to help but always to focus on actually doing something with a mentee, not just being a sympathetic listener but to help that person toward a particular goal. The label "mentoring" is not required: these relationships can be peer-to-peer, teacher-to-student, supervisor-to-staff, or between team mates. What is important is that there is a chemistry between the two and that they are on a purposeful journey together, sharing knowledge and wisdom.

Another early story from Sashi is from when he was an Engineering student at JNT University. Outside the thirty-year-old college was an orphanage for street children. Sashi and eight of his friends noticed the kids playing outside one day and went in to talk to the orphanage manager. When they realized that these young children were not in school, without permission Sashi and his fellow university students started using the college facilities to teach orphans English, Math, and Science. After the classes had been going on for some time, a District Collector (like a Mayor) came to the orphanage with his entourage of police - to conduct a surprise inspection. The official was surprised to find no children there. The orphanage manager brought the official party to the college next door where they watched 19-year-old Sashi and his friends teaching the children. Sashi was scared to see all of the police enter the room - but he kept on teaching. The District Collector sat down in the back and listened.  After the class, he told Sashi how touched he was and invited Sashi to his office to talk. It turns out that the official himself had been an orphan. The initiative and generosity of Sashi and his friends impressed him.

Sashi came to the USA at age 24 and worked all over the country. He became a US citizen in 1989 and continued his work both as an entrepreneur and teacher-mentor in many companies. When Sashi acts as a mentor, his goal is to turn on a light switch in his mentee - to remove darkness and showcase the solution or path that was already there.  Sashi is a mentor and advisor to MentorCloud, which powers the TiE Silicon Valley MentorConnect program.

Image Copyright 2013 by Katy Dickinson