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Shirish Nadkarni (MBA 1987) was the director of product planning for Microsoft’s MSN when he decided he was ready to become an entrepreneur. He had recently led the growing internet portal’s 1997 acquisition of Hotmail, the first free, web-based email solution, and the experience had given him a window into the young online-software market. He saw a need for a product similar to Hotmail that was tailored for businesses, a web-based email solution with calendaring and scheduling capabilities. “I thought it was a great idea,” Nadkarni says, “and I just went for it.” What he didn’t do, he readily admits now, was the extensive research necessary to validate his idea. He quickly discovered that the demand simply wasn’t there. “We were too early,” he says.

The story of TeamOn Systems, the email-technology company Nadkarni founded in 1999, has a happy ending. After pivoting to a mobile-email product, the company was acquired by RIM, the company behind BlackBerry, in 2002. But that’s not why he tells the story to the fledgling entrepreneurs he mentors through TiE Seattle, a regional chapter of the global nonprofit The IndUS Entrepreneurs (TiE), which began in Silicon Valley in the early 1990s. Instead, it’s a cautionary tale. “I emphasize the importance of finding a clear pain point and making sure that there’s a real need in the marketplace,” he says. “I talk about the importance of achieving product-market fit before you start investing a lot of dollars to create demand for your solution.”

Nadkarni joined TiE Seattle when it launched in 2000. The chapter was focused on promoting networking and the growth of the startup ecosystem in the Northwest, especially among the Southeast Asian community. For Nadkarni, who was at the time still new to entrepreneurship, TiE was an invaluable resource. He received advice from more experienced founders, and angel investors affiliated with the nonprofit were among the backers of his startups; Nadkarni followed up TeamOn with Livemocha, a pioneer in the social-language learning space, which was acquired by Rosetta Stone, and Zoomingo, a mobile shopping app acquired by Motivity Labs. Now Nadkarni, who retired from entrepreneurship in 2015, is the one sharing lessons to the next generation of startup founders.

“I love working with smart people. I love the idea of helping entrepreneurs create a business, grow it, raise funds—all of that. It’s just something that really excites me deeply,” says Nadkarni.

Nadkarni sits on the board of TiE Seattle and chairs two educational initiatives he established to expand the organization’s efforts beyond networking. The TiE Entrepreneur Institute runs each spring, giving would-be founders an inexpensive, 10-session crash course on the fundamentals of starting one’s own business, from ideation and fundraising to go-to-market strategy and sales. TiE Seattle’s Go Vertical Startup Creation Weekend is a mini-incubator. Over the course of three days, participants with expertise in a variety of areas—business professionals, software developers, data scientists, and such—share ideas, build teams, develop and test concepts and business plans, and finally pitch their prototypes to industry experts and venture capitalists. And the support doesn’t end there, Nadkarni says. “If the idea is really good, we’ll mentor them with the hope they’ll actually do it.” He also invests in and advises promising Seattle-area startups, such as Bloomz, a parent-teacher communication app used in 25,000 schools across the United States.

Nadkarni wants entrepreneurs beyond the Northwest to benefit from his hard-earned experience as well. He’s penned two books on founding a business. From Startup to Exit, published in 2021, is “a textbook version of the TiE Institute,” Nadkarni says. Winner Takes All, published in 2023, is a guide to operating an online marketplace.

“Retirement is not all fun and games,” he says. “There’s only so much you can travel; there’s only so many books you can read. So you need to find a purpose in life and meaning in what you’re doing. I find meaning and purpose through helping other entrepreneurs.”

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