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Silicon Valley CEO shares why taking risks leads to possibility

Oct 15, 2021

The career path of Sukhinder Singh Cassidy, HBA ’92, has been far from linear. Although she has founded several highly successful companies, most recently theBoardlist, she said there have been misfires along the way. But taking bold risks and continuing to trust her instincts has ultimately allowed her to build her dream career.

For the annual Richard G. Ivey Speaker Series, Singh Cassidy shared with HBA students lessons learned from her 25-year career in Silicon Valley, drawn from her new book Choose Possibility: Take Risks and Thrive (Even When You Fail). A leading technology executive and entrepreneur, Singh Cassidy has founded, scaled, and advised companies including Google, Amazon, StubHub, and Yodlee. In 2019, she became the first recipient of the Ivey Alumni Achievement Award.

During her visit to Ivey, Singh Cassidy also did a session with Executive MBA participants and a virtual fireside chat for The Ivey Academy. She also sat down with Professor Eric Morse, Executive Director of the Morrissette Institute for Entrepreneurship, for a video interview to discuss highlights from her career, her approach to taking risks, and her advice for the business leaders of tomorrow.

Watch the video above.

The Richard G. Ivey Speaker Series is an annual tradition to honour Richard G. Ivey, the Canadian business leader who helped build the foundation for the Ivey Business School. Each year, Ivey welcomes a business leader who, like the Ivey family, is a respected leader and embodies Ivey’s mission.