There is one fundamental skill that all entrepreneurs use to find success: they continuously take risks until something sticks. Sukhinder Singh Cassidy is an Internet executive and entrepreneur with experience building, scaling, and leading businesses - most notably, Google, theBoardlist, and Amazon.

Her most recent work as President of Stubhub led the company to sell for $4B! She is a multi-time board member and/or angel investor at private and public companies including TripAdvisor, Urban Outfitters, and Sunbasket. She shares her wisdom with people to help them succeed as leaders and build products that empower consumers which she does incredibly well through her book, Choose Possibility. 

Dive right in and learn what it means to choose possibility by taking risks and how risk-taking is a skill that can be learned. 

Things you will learn in this episode:

[00:01 - 05:12] Opening Segment 

[05:13 - 15:01] Choose Possibility by Taking Risks

[15:02 - 33:40] Putting Yourself in Opportunity-Rich Environments

[33:41 - 35:02] Closing Segment 

Tweetable Quotes: 

“Hustle and risk-taking… risk-taking is like putting bait out in the water constantly to sort of creating your own possibilities.” - Sukhinder Singh Cassidy

“If you’re willing to embrace choosing possibility as a process you will have outsized returns.” - Sukhinder Singh Cassidy 

“To be a smart risk-taker is to put yourself in an environment where you’re most likely to succeed.” - Sukhinder Singh Cassidy

Resources Mentioned:

You can connect with Sukhinder on LinkedIn and Twitter. For a powerful new approach to taking risks, you gotta check out https://www.choosepossibility.com/. 

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