Choosing Possibility

Sukhinder Singh Cassidy has made consistent risk-taking the pillar of her career

Founder. Chairman. CEO. President. Venture Partner. Co-Founder. Strategic Advisor. Sukhinder Singh Cassidy has held a number of titles with some of the world’s top brands—StubHub, Google, Twitter, Amazon—throughout her career. But one title that’s always relevant, and most true to her roots, is entrepreneur.

Singh Cassidy grew up in St. Catharines, Ontario with a father who was a doctor and who ran his own business. “My dad certainly wired my brain for entrepreneurship, probably without me realizing it at the time,” Singh Cassidy says. Even after securing traditional media and banking jobs in New York and London, the lure of entrepreneurship motivated her to quit a job in London and move out to the Bay Area in 1987.

“I knew I wanted to be an entrepreneur, but I didn’t know how,” Singh Cassidy recalls. “I went to visit a friend in the Bay Area and fell in love with the energy and possibility of it. I figured if I put myself in Silicon Valley I would get close to other entrepreneurs and figure it out.”

Taking risks

After 23 years in the Valley, Singh Cassidy is getting ready to publish her first book in August with the theme of taking risks and choosing possibility. “I often get credit for taking risk in my career, because people think of risk taking as fairly daunting in their careers,” Singh Cassidy says. “But I’ve long felt that risk is really misunderstood. For people outside the Valley, it seems like living here either ensures a ride to glory or a ride to epic defeat and failure. I think risk is more nuanced than that. Risk is a process, not an either/or situation, I call choosing possibility. The process of risk is continuing to make choices, looking at the results, and thinking about whether the results gave you what you originally intended, or gave you something to learn from to inform your next choice. That series of choices cumulatively delivers results. If you only want to choose once, that’s unlikely to deliver the results you want.” 

Choosing possibility is the foundation for Singh Cassidy’s entire career in the Valley, and the advice she gives to budding entrepreneurs: take repeated risks for career growth, and do it in a considered and calculated way. In Singh Cassidy’s view, there is no one “right” way to “make it” in the Valley. 

“In my own career, I have been able to navigate and transcend many different cycles and stages and sectors,” Singh Cassidy says. “I am proud of that versatility and my background. People always ask me what I ‘did’ to get to where I am today. And it’s not like I did just one thing right, it’s that I embraced this idea of risk as a process. I really do believe that success in the Valley, and in tech, is something that is accessible to every single person. I don’t want to put my career on a pedestal, I think success is something anyone can build if they’re willing to embrace that process of actively making choices as a repeat process. I think that sometimes there’s a sense that women are more risk averse than men, but I know that women don’t lack any ambition. What I would say to anyone early in their career, or even later in their career looking for continued growth, is that when the choice seems binary, there is always more than one solution to any problem. Just think about how there is always an incremental choice you can make that will move you towards your goal. If risk as a concept seems daunting, think about the minimum viable choice you can make to move you forward. Make a choice, even if it’s the smallest choice, if you want to accelerate your growth and progress.”

Choosing to change

The Silicon Valley of 2021 looks very different from the place Singh Cassidy moved to in 1987. The buzzy startup city is now an established hub with startups and large brands alike that are, admittedly, typically led by men. As the Valley continues to evolve, there are two things Singh Cassidy would especially like to see change in the startup world: leadership diversity, and more equitable distribution of wealth. 

“While I’d like to see the acceleration of diversity and inclusions on boards and executive teams, what I want even more is to get past the point where there’s only one diverse leader—it’s not enough to have one woman on your board and say ‘look, our board is diverse!’ I am looking forward to the time when diversity is the rule, not the exception. It’s not so notable to be ‘the one’ or ‘the first’ because to be ‘the one’ is to be alone and, often, lonely. There is research that points to this—being a woman in a male-dominated space is challenging. The change I want to see in the startup space, and that I want to be part of, is making sure we get to a place where there is no longer “the one” diverse person on a leadership team. I want to see more diverse groups, because diverse groups make better decisions. 

“I think tech is amazing at creating world-changing solutions to big problems, says Singh Cassidy, but sometimes I feel like we are so worried about how to change the world, but we don’t worry enough about how to change the communities in which we operate. There are so many people in our communities who are suffering from the pandemic and tech is seeing the biggest bubble that it’s ever seen in terms of the stock market, and there is so much wealth inequality in the Valley. I don’t begrudge wealth creation or capitalism—I am here participating in that ecosystem. But I do wish that this digital divide was not so extreme, and that there was a way for tech to participate in solving local problems as much as trying to solve big, audacious goals. It seems to me that there’s a pretty big divide that needs to be bridged.”

Creating and supporting community

To be part of creating the changes she wants to see, Singh Cassidy has founded two important initiatives. After establishing herself as a leader in the Valley, Singh Cassidy thought about how to formalize opportunities to connect and help others—specifically, women and people of colour—in her network. 

“While I’ve been able to unlock a lot of possibility for myself, I believe that the other opportunity we all have is to unlock possibility for others,” Singh Cassidy says. “If I’m going to do this for myself, I would love to create a scalable way to do it for others.” In 2015 she founded theBoardlist, a platform for CEOs and board directors to connect with a diverse community of recommended talent. “theBoardlist is one example of trying to drive change in leadership by recruiting more diverse talent, and addressing the absence of diverse leadership at board and executive levels,” Singh Cassidy says.

Earlier this year, Singh Cassidy co-founded another venture to address a common problem in the Valley: inequitable access to wealth creation. The Acre Diversify Capital Fund pools the capital of a diverse group of leaders to give them access to investment opportunities in growth stage technology companies. “To create wealth, and the next generation of diverse angel investors, you have to create more wealth opportunities for diverse leaders now. With the Diversify Capital Fund, we can simplify the opportunity to equalize wealth creation. We represent many diverse leaders through a single check, that can actually diversify the own ownership tables of leading companies.”

The importance of connection

While it’s not possible for Singh Cassidy to point to one decision or moment in her career that was most significant in her growth and journey, there is one more common theme beyond taking risk and choosing possibly—connection. “I think what I am most proud of is that I’ve gotten to work with some pretty exceptional people,” Singh Cassidy says. “Whether the companies were big or small, whether they failed or succeeded, I feel like I have been privileged to be part of so many amazing teams that set out to change their own corner of the world. And I hope that I was an accelerant for some of those people and their careers, they certainly were an accelerant for me. I’m honestly most proud of the company I’ve kept, the company I’ve been able to attract, and the company I’ve been able to be a part of.”