704: Sukhinder Singh Cassidy | Choose Possibility by Taking Risks

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

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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:

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/. 
 
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