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Sukhinder Singh Cassidy, CEO of Xero on the importance of tailwinds, and "macro" and "micro" startup environments

People always think that as an entrepreneur it's always about your own execution. I thought the same thing. And sometimes you realize that timing and tailwinds matter.

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Episode Description

Sukhinder Singh Cassidy, CEO of Xero, joins the show to talk about

  • Her first exposure to entrepreneurship running the books for her father's business
  • How Sukhinder has thought about evaluating the entrepreneurial ventures she has taken on, and how she evaluates the importance of the market/opportunity, and team she's building.
  • How Xero is using AI to help support small businesses, and opportunities that Sukhinder sees for small business to save time and money.

Episode Transcript

Sukhinder Singh Cassidy

CEO of Xero, founder of theBoardlist

Sukhinder Singh Cassidy is one of the most well-respected female tech executives in Silicon Valley. Named one of Fast Company’s Most Creative People in Business, she’s the CEO of software company Xero and former president of StubHub. She’s helped scale companies like Google and Amazon, and founded theBoardlist: a premium talent marketplace for diverse leaders. But despite her many successes, she’s the first to admit her path hasn’t always been linear. In her book Choose Possibility, Singh Cassidy reveals the many poor choices, misfires, and unexpected headwinds she’s encountered along her path—providing a thoughtful new perspective on risk-taking: what it is, what it isn’t, and how to master it to achieve lasting success.

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