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  I introduce today’s guest, Sukhinder Singh Cassidy For a better way to book world-class guests head over to Guestio.com  Sukhinder gives us a bit of her background Grew up as the daughter of two doctors  How she learned to do books and taxes as a kid  Learning what it really means to run your own business [05:13 - 15:01] Choose Possibility by Taking Risks Sukhinder talks about her early encouragements towards entrepreneurship Sukhinder’s venture into education and careers  Going into business as a ‘less risky choice’  How it took over a year to get a single job offer Learning to take risks Her experience in corporate Venturing into ownership, “I will figure it out”  The importance of being able to shift environments Give yourself chances to fail  A quick word from our sponsors [15:02 - 33:40] Putting Yourself in Opportunity-Rich Environments Sukhinder shares the key to choosing possibility  Be willing to embrace the process How to get yourself in the right ‘risk-taking’ environment Pursue the ‘Who’, not the ‘What’ Get yourself with ‘Superbosses’  Common characteristics of superbosses  The polar opposite of you  Patient and without ego People who release you to fail on your own  Superbosses will share some level of your values  Building relationships with your bosses Go to places where your skills are valued  You need to know your own weaknesses and superpowers  How Sukhinder is as a superboss Who you know or what you know?  Our credibility comes through constant education and who you are Sukhinder’s “Why” behind the book Choose Possibility  Showing an inside-out view of successes and failures Playing the long game and continuing to choose  Risk-taking can be a learned skill [33:41 - 35:02] Closing Segment  Go to Choosepossibility.com and take The Risk Quiz How to connect with Sukhinder - links below Final words   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 CassidyResources Mentioned: Choose Possibility: Take Risks and Thrive (Even When You Fail) Superbosses 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/.  Did you love the value that we are putting out in the show? LEAVE A REVIEW and tell us what you think about the episode so we can continue putting out great content just for you! Share this episode and help someone who wants to connect with world-class people. Jump on over to travischappell.com/makemypodcast and let my team make you your very own show!If you want to learn how to build YOUR network, check out my website travischappell.com. You can connect with me on Facebook, Instagram, and Twitter. Be sure to join The Lounge to become part of the community that’s setting up REAL relationships that add value and create investments.Check out FranBridge Consulting for premier non-food franchise opportunities: travischappell.com/franbridgeOur Sponsors:* Check out Kinsta: https://kinsta.com Learn more about your ad choices. Visit megaphone.fm/adchoices