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A serial entrepreneur on what makes and breaks a new business

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A wave of new businesses will emerge as the pandemic recedes, but many of them won’t survive.
Shirish Nadkarni is one of few serial entrepreneurs who can say he has exited successfully from every startup he has ever launched. His first company, TeamOn Systems, was an early pioneer of the SaaS model, providing customers with business-grade email and calendaring in the cloud. Although not everyone understood the value of the idea in 1999, and the company later had to pivot to a slightly different product, it went on to be acquired by BlackBerry a few years later. In 2007, Nadkarni founded Livemocha, the first language learning company to adopt a conversational approach to teaching. Although it was never profitable, Livemocha quickly accrued millions of users and was eventually snapped up by Rosetta Stone. Finally, there was Zoomingo, a mobile app that helped shoppers identify stores running sales in their local area. At one point, the app managed to climb into the top ten in the Apple App Store (and top 25 on Android), and it too was acquired. However, Nadkarni suggests his shining report card doesn’t necessarily paint a full picture; he made many fundamental mistakes along the way. And while an exit is the goal of almost all entrepreneurs, Nadkarni never enjoyed the luxury of selling on his own terms, precisely when he wanted to. Nadkarni came to the US in the early 1980s to study computer science, which wasn’t taught widely back home in India. “I was fascinated by computers; what you could do with them, what you could build,” he explained. After graduating from the University of Michigan, he undertook an MBA at Harvard Business School, with an eye on entrepreneurship. He hoped to learn how to blend technical skill with business know-how, a formula that was being applied to great effect in Silicon Valley. However, Nadkarni suggests his education only truly began after he landed a job at Microsoft. It was here he gained practical experience and an appreciation for the qualities that separate a brilliant idea from a mediocre one. “I learned a lot at Microsoft,” he said. “I learned how to build, launch and market great products, and I understood the business models. So I had a really good grounding that I could use to become successful in the startup environment.” It’s hard to imagine, but Microsoft was itself a startup when Nardkarni first joined, with only roughly 1,000 employees. At the time, the company was looking to branch out into new product areas, beyond hardware, office software and its Windows OS. Initially, Nadkarni was brought in to help launch the company’s first email product, Microsoft Mail, but he ended up working on a wide range of major projects during his twelve-year tenure.

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