Sukinder Singh Cassidy is a leading technology executive and entrepreneur, board member and investor. Joined Amazon in 1998, then co-founder of Yodle, Google in 2003, head of Asia Pacific and Latin America. Sukinder most recently served as head of StubHub, which led to $4+ billion in sales in 2020. Founder of Portalist, which identifies places of representation on industry technology corporate boards.
Sukinder Teacher Selection Possibility: How To Take Risks And Grow Up (Even If You Fail). He shared his thoughts on how to have a healthy relationship with risk, get down the career curve, and set yourself up for a board seat in our recent chat. This conversation is part of a series of conversations with women technology leaders.
Nancy Wang: You started three companies and served as CEO of two more companies that helped Google grow, and TripAdvisor, JP Awesome Careers, who also served as a team member for brands including Crew and Stitchpix work done. You project your growing career into the many small and big choices you’ve made over the decades, rather than one big decision. What mental and value structures guide your decisions?
Sukinder Singh Kasidi: People always think that taking risks is a powerful option. When we force ourselves to pay that price, we may or may not make the right choice. That pressure often turns people away.
In mapping out my own life, I continue to make choices and aim for impact. I took too many risks that didn’t happen. I set up a video trading company 10 years ago, the current video business got annoyed; We were very fast. I was the CEO of a startup I joined and then left for six months. The combined benefit of learning at each stage opens up the value of the next option.
If you want to take a turn, you can bet on luck. When you become a chosen creator and adventurer who thinks about the possibilities and goals of making an impact, you may realize that you may or may not have thought as much as a result as a result. You make an impact, increasing your agility, consistency and ability to make the next choice and make the kind of exaggerated professional impact that can be measured in no time.
Another thing that has particularly helped me choose in my life is what I call above. We are often trained to believe that pursuing your interests is dangerous. With this, emotions change and interests change, but this has a greater impact on who you choose to work with, what you learn and what you share.
Wang: I recently heard a speaker refer to the M-curve of women’s lives as similar to the McDonald’s curve. You will find yourself climbing the career ladder, growing up and accepting bigger roles, and achieving bigger and bigger goals. Suddenly, you can see it coming down the curve. How can you use your framework to go over the m-curve?
Singh Cassidy: People take a kind of straight line in the lives of successful people because they only see the pinnacle of their life. I know people do this to me. In my new book, I came up with an idea to show you all the colors of my career, which is not obvious because no one from outside told that story. Many of us have more M-curves than people.
There is a difference between a bad M-curve and a good M-curve. When I think of women in particular, it’s because women can move from their care to child care or nursing. In the temple, women are at an even greater risk when combined with the burden of excessive maintenance. With that, I worry about the bias a person faces when attempting to re-enter the world of work. If you’re already in this situation, before you decide that nothing is possible you should leave, I recommend going to work and asking what might happen. Can you ask for the flexibility that allows you to be in the world of work you are today, and not suffer some of the pain that happens when women completely go out and re-enter? Going out and reusing it is not to say that it is the wrong choice in your life. Sometimes when women reach this M-curve, somehow they have to return to the world of work after retirement because they don’t get all the credit they deserve for that responsibility. Or they had the title when they left, especially if they left in the middle of their careers. The bad type of M-curve is that we face bias or discrimination in the choice to do many important things in our lives. Sometimes as women we suffer the consequences of our choices taking risks that are unfair.
A good type of M-curve has a growth mindset. I stepped back in my life. Some might say I take “title letters” or other things to develop or learn to make an impact. When I left Google, I became the founder and CEO of a 10-person startup. I am recovering in terms of income, corporate liability and fees. I pursued a career to learn. The mix will return over time when you step back and take the industry risk of learning something new for greater impact.
Wang: You and I are interested in tackling gender discrimination in the technology industry. You solve this problem through the portallist you have set up to connect women to board opportunities. Many aspiring women aim to join the board of directors, but the path to these positions is not always clear. What advice would you give to those looking for this kind of leadership position? What should a person do to prepare himself?
Singh KC: The first thing I would say to people looking for boards is if you are
