The Pioneer
The frontier and an appetite for the unknown, goes first.
Sukhinder Singh Cassidy earns The Pioneer designation not through dramatic leaps but through her lived philosophy of iterative, calculated risk-taking. The former StubHub president and author of Choose Possibility treats forward momentum as something accumulated, a multitude of risks rather than one singular bet.
“Yeah, well, by the way, I would say to people it depends over what time frame you characterize that decision. On a six month timeframe or your timeframe, that was a failed decision. And I call it a failure because I failed to have impact. You know, it's different than joyous, right?”
“Because Rob pushed both of us. He pushed them to call me and need to consider it. And you know, when the situation went awry at Polyvore, the number one person I called was a guy named Becky Harry Narayan, one of those jungly founders and the one I was closest to who continue to know me and invest in all the companies I founded.”
“Once you visit California, you sort of realize that it's possible to live in good weather all year long. But the other truth was I wanted to be an entrepreneur. My father loved running his own small business.”
“Part eg Yeah, you got it. So, and by the way, and in this case, look, completely professional, like you have a founder who's been out of the company for 20 years and has nothing to do with near 15 years. He had started a competitive ticketing company, and now you want to come back. And by the way, he had been pushed out of the company.”
Masters in Business: “Sukhinder Singh Cassidy on Entrepreneurship (Podcast)”
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