704: Sukhinder Singh Cassidy | Choose Possibility by Taking Risks

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By Travis Chappell. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.

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 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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