The Learning Leader Show With Ryan Hawk
The Learning Leader Show With Ryan Hawk
432: Sukhinder Singh Cassidy - How To Take Risks & Thrive (Even When You Fail)

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Full show notes at www.

Twitter/IG: @RyanHawk12

Sukhinder Singh Cassidy is a leading digital CEO and entrepreneur with more than 25 years of leadership experience founding, scaling, and advising companies including Google, Amazon, StubHub, Yodlee, and more. Most recently, Sukhinder served as the leader of StubHub, the premier global consumer ticketing marketplace for live entertainment, which she and her team sold for $4 billion in February 2020. Earlier in her career, Sukhinder built Google’s business throughout Asia Pacific and Latin America.


  • “Nothing will ever be attempted if all possible objections must first be overcome.” – Samuel Johnson
    • “We think when we do nothing there is no cost.” That’s not true. There’s a cost to standing still.
  • Proximity to opportunity benefits us even more than planning. Sukhinder moved to Silicon Valley in 1997. She rode the tailwind of the Internet and being at the epicenter of it all.
    • Prioritize the WHO before the WHAT.
  • As a leader, watch what you validate with your words and actions. Reward the behavior that you want. If you want to promote taking risks, then reward the people who do that. “You get what you create and what you allow.”
  • At one point, Sukhinder went to her boss at Google (who worked with Eric Schmidt) and said, “I’m pregnant, I want to keep running international at Google. I need for you to pay for me and my nanny to travel the world business-class. And they said yes.” BIG ASK.
    • She did the calculus and realized it was a reasonable ask. And they said yes.
  • Career path – “My career is not linear, it’s cyclical. It has ups and downs. I’ve made 13 different meaningful choices along the way.”
  • The myth that there is a linear relationship between risk and reward. Not all choices have an equal amount of upside and downside…
  • Sukhinder sas been on the board of Urban Outfitters with Scott Galloway:
    • Should you move to a big city? Should you move to your company’s headquarters?
      • Being at the center of the action matters… It helps if you can understand the pulse of HQ
  • How to become a smart risk taker?
    • What are our goals, passions, and values?
    • What are we great at?
    • Look for headwinds and tailwinds – (Join a growing company that has momentum)
      • With that said, Sukhinder went to StubHub and there were significant challenges
    • Over-prioritize the WHO over the WHAT
  • Why did Sukhinder take the StubHub leadership role?
    • It was a calculated risk
    • She missed running a company of scale
      • They needed entrepreneurial and executive energy
  • How do you create an environment for people to take risks?
    • You want people who are “truth-tellers, truth seekers, and authors”
    • Make it safe to take risks — Reward that behavior.
    • Watch what you validate by your words and actions. Understand the magnitude and the weight of your words. People are always watching how the leader responds, who they commend, what they say…
  • How to go for a job that you aren’t qualified for?
    • “The next level of learning is going for something you don’t know…”
    • To be a CEO, you need depth AND breadth. You need to expand your skillset. This is the path to accelerated learning.
  • How do you know when you should leave a job?
    • “I like 3-5 year sprints. Are you having fun? Are you making an impact? If you aren’t having fun or making an impact, you’ll want to leave.”
    • Think about: “Who am I doing this with? Are our values aligned?”
  • Why did Sukhinder want to be a CEO?
    • “A little bit of ego”
    • “I was built to lead”
    • “I enjoy being on the hook”
  • People who sustain excellence:
    • They surround themselves with other great people.
    • They don’t let their ego get in the way.
    • They don’t feel threatened by great people.
  • Career/Life Advice:
    • “We tend to assume that everything is zero-sum. It’s not. Choice is a multiplier of opportunity and we get to control it. Make a choice and get in motion.”
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