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The Adversity Advantage

Aug 19, 2021

Today’s episode welcomes Sukhinder Singh Cassidy, a leading technology executive and entrepreneur, board member, and investor with twenty-five years of experience in founding and helping to scale companies, including Google, Amazon, and Yodlee. Most recently, she served as president of StubHub, which sold in 2020 for $4+ billion right before the pandemic and thrived under her leadership. She has been profiled in Fortune, Forbes, The Wall Street Journal, Business Week, and The New York Times, among others. She has been named one of Elle’s Power Women, one of the Most Creative People in Business by Fast Company, and one of the Top 100 People in the Valley by Business Insider among many other accolades. 


Our discussion today center’s around several topics that many struggles with failure, risk taking, and changing direction. If you listen to this episode in full, I guarantee you that you will feel more confident when facing these challenges. We chat about Sukhinder’s unexpected and abrupt departure from StubHub and how she handled that and used it as an opportunity for growth.


Sukhinder and I get into the in’s and out’s of all things risk-taking including why you must take them, how to know if it’s the right one and how to do it the right way. She also talks about why proximity and protecting the downside are CRUCIAL when taking chances.


We also chat about the different types of failures that you will experience in life, how to plan for them, overcome them and why you can actually learn and grow more from unplanned setbacks.


Sukhinder unveils what must happen in order for someone to make the choice to take action and make a change and if she thinks that some of us are wired to be bigger risk-takers. 


Our convo also gets into how to surround yourself with the right people, common risk taking myths and how to become fulfilled and impactful long term. 


Buy Sukhinder's book "Choose Possibility: Take Risks and Thrive (Even When You Fail)


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