In “Choose Possibility: Take Risks and Thrive (Even When You Fail),” she charts her extremely varied career with the kind of candor that is as rare as it is full of lessons for other entrepreneurs and leaders. She has served as a top financial analyst at Merrill Lynch, a unit manager at Amazon, a senior executive at Google, the CEO of five companies (including three startups), and a member of the board for companies like TripAdvisor and Urban Outfitters.
If that isn't enough to prompt your interest in reading it, consider what may be the best cover blurb in the history of business book publishing: "Singh Cassidy is one of Silicon Valley's most well-respected leaders. Her unique style of authenticity, optimism, and hustle will help anyone unlock their potential." That comes from Eric Schmidt, former CEO and chairman of Google, who has a pretty good idea of who else is at the top of the silicon Mt. Everest.
"What would I say to my younger self? Choose a goal, then make a choice, however small, and start executing, aiming for impact every time. Then keep choosing new goals and opportunities and reach them,” she said in an interview with Startup Savant. “The more you do, the better you will get at choosing. There is a myth about a linear relationship between the size of the risks and the benefits: the bigger the risk, supposedly the greater the rewards. But we shouldn't romanticize risk because you can get smarter about your choices by diversifying the types and size of risks you take. You can plan more for potential downsides and learn to make wiser intuitive decisions with experience, advice from mentors, and learning from those you work with."
Pipelining in Parallel
Singh Cassidy had entrepreneurial parents as role models, medical doctors who had moved from Tanzania, where they had a successful practice, to Canada, requiring them to start over financially and become newly licensed. She was taught how to do the taxes for their office in St. Catharines, Ontario, at age eight (that is not a typo) and worked there, giving her very early insight into the risks and rewards of owning a small business.
During college, she learned cold-calling to sell conference room space for a hotel and to set appointments for demonstrations of high-end vacuum cleaners. On graduation in 1993, she started at a Toronto investment bank, but her heart wasn't in it. She had also interviewed at the world headquarters for Merrill Lynch in New York City because she liked its aggressive culture, but the process of vetting her was long. She also passed the exam for the Canadian Foreign Service and for law school, and she applied for a medical school interview.
"I used this technique of discovery-based risk-taking — or pipelining in parallel, as I call it — throughout my career to clarify my goals and put myself in motion early to pursue them," she said. She has some tips for others seeking their next position at any stage in their career:
- Create your own discovery timeline. Don't just react to others' schedules.
- If an opportunity seems urgent, think through realistically the upside benefits and downside losses that might result from a quick decision.
- Brainstorm with a buddy who might not be a friend, but they have a professional perspective on the kinds of choices you’ve made. In turn, they might ask some probing questions about why you want to move on.
- Partake in passive pipelining, from participating in events that will expand and diversify your network to studying companies for investment purposes that could be attractive places to work.
She finally landed the job at Merrill Lynch, where she had an unusually creative and demanding boss who gave her increasing responsibilities. After one year, she was transferred to the London office for a coveted job covering European banks. However, a year later, Singh Cassidy realized she wanted not simply to be an advisor but an executive. She joined Sky (now British Sky Broadcasting), part of Rupert Murdoch's empire, but her position as assistant to the COO left her feeling underutilized. She was eager to be involved with a startup, so she moved to California.
Hired as a business development manager in 1997 at OpenTV, an early interactive television startup in Mill Valley, she discovered that it was hard to get credit for her achievements in a sexist culture.
The next year, a headhunter recruited her to Junglee, a startup that brought together information across the young Internet for other companies to use, such as the job board and shopping service it had created for Yahoo. Her first responsibility was to persuade other shopping sites to partner with Junglee. At the time, Amazon was mostly selling books, music, and videotapes, but six months later, it acquired Junglee for $280 million as its first step to building its Marketplace. Singh Cassidy's stock was worth $1 million, and she moved to Seattle to work in Amazon management.
"My decision to move from OpenTV to Junglee taught me an important early lesson in taking smart risks, one that has been reaffirmed multiple times in my career," she wrote. "When making critical career choices, we can't overestimate the importance of the 'people' factor. I originally signed on at Sky and OpenTV, because I loved being part of the entertainment industry … I felt less passionate about Junglee at first … I succeeded because I surrounded myself with people I respected and from whom I could learn while thriving in the culture they created."
In 1999, she decided to fulfill her dream of becoming an entrepreneur, even though it meant leaving a high-paying, prestigious position in a fast-growing company. She co-founded Yodlee with some engineers who had developed programs that could aggregate personal financial information from online sources. They raised $15 million and she served as a senior vice president.
The original plan was to help consumers manage their finances, but this was long before it became popular, so they pivoted to having financial institutions to offer this to customers. It eventually succeeded as business-to-business software, but she left in 2003, having only made a modest amount, yet with new leadership skills and a reputation for creativity. "It was one of the most positive emotional and reputational events of my career," Singh Cassidy recalled.
Because of those achievements and a referral by Junglee's former president, an angel investor in Google, she became one of its first 1,200 employees. She managed Maps and Local Search and the next year was tasked with building up Google's presence in Asia and Latin America with a team of 2,000.
"As business conditions become ever more dynamic and complex, we should strive to develop deep specialization as well as a set of diversified experiences in which we apply what we know and keep learning to adapt and expand our knowledge further," she wrote.
Ready to choose her next possibility as the CEO of an emerging company, she joined the Young Presidents' Organization to get feedback on opportunities and left Google in 2009.
In February 2010, she accepted an offer to helm the 10-person startup Polyvore, which allowed women to clip online images to create fashion and decor idea boards that could be instantly shoppable. Although successful by many measures, she found herself at odds with the founder and left after six months.
She had learned to protect herself in contracts, keeping her shares, which paid off when Polyvore was sold to Yahoo in 2015. Being the CEO in early ecommerce also paid dividends in new leadership skills and in 2011, she was hired to head another startup, Joyous, which was pioneering videos tied to shopping.
Joyous had many successes, including forging partnerships with Time Inc. and AOL and doubling revenues each year, but consumers were still new to video platforms. In 2017, Joyous was sold to StackCommerce for a relatively small amount.
"The six years I spent at Joyous were as fun, fulfilling, incredible, frustrating, and painful as any pure startup can be," she wrote.
A series of charts on pages 118 to 122 of her book can help readers rank the upside and downside risks and rewards of the prospects for a career change and come up with a final score for a decision. This can inform your gut instinct, "which pretty much amounts to making a quick judgment with origins that remain somewhat mysterious to us."
Choosing a Higher Calling
After Joyous, Singh Cassidy decided she wanted a leading role at a large enterprise, hopefully in ecommerce, to grow her skills to the next level and diversify the risk and reward potential. In 2018, she accepted an offer to become president of StubHub, the global ticket marketplace owned by eBay, with over $1 billion in annual revenues.
In February 2020, StubHub was sold to Viagogo, which was a quarter of eBay's size, for more than $4 billion. A month later, the pandemic shut down live events around the world, and StubHub was faced with having to refund angry customers who wanted their money back without a parent with deep pockets. Yet her team worked through the enormous challenges.
"If you have less positive results than you hoped, it's essential for your future career to understand your role in the outcome," she said. "I've always welcomed feedback on my strengths and weaknesses from family, friends, colleagues, and mentors and have been sometimes surprised by what I've been told. Developing more self-awareness is a key to making better decisions."
You may have been trying to do too many things at once, excelling at none, might have confused busyness with real progress, avoided dealing with unpleasant issues, or sent signals that you only wanted positive feedback. To have more impact, she recommends:
- Putting passion into your work, even when it isn't passion-inducing.
- Prioritizing making progress over trying to achieve perfection.
- Developing original ideas, rather than waiting for others to contribute.
- Speaking out about a proposal you think is flawed.
- Developing both deeper expertise and broader interests.
Since 2015, when she founded theBoardlist, Singh Cassidy's primary passion has been to help companies diversify their boards. It was a cause that was long overdue, as firms became much more aware of the need to play a positive role in society and to better understand the changing demographics of their customers. Thousands have joined and contributed referrals for highly qualified women and minorities. She says searches are being increasingly done on the site for executives, a natural extension of the platform that will be formalized in the near future.
"More than anything I've created, it has the potential to truly change the distribution of opportunity and power systematically and to everyone's benefit," she wrote. "It's certainly the most meaningful and ambitious pursuit of my career so far."
This is a reflection of the realization by many that because so much of our time is spent at work, it has to be about much more than simply making money.
"People increasingly want to work for companies and be customers of those that share their values about what is good, fair, and just," Singh Cassidy said. "This can be as important as whatever the product or service is, and they look for leaders who will stand up for what matters. You can even go beyond a basic moral code to what I call spirituality, which doesn't have to be religious but is a belief that there is something greater and higher that guides us. This can also help us accept the fact that we cannot control every outcome, only do our best. When I was growing up, my parents told me that my time on earth was limited and I should develop my gifts to have a positive impact, which will give life meaning. I have always kept that in mind, regardless of what was going on at the time."
About the Author
Scott S. Smith has had over 2,000 articles and interviews published in nearly 200 media, including Los Angeles Magazine, American Airlines’ American Way, and Investor’s Business Daily. His interview subjects have included Bill Gates, Richard Branson, Meg Whitman, Reed Hastings, Howard Schultz, Larry Ellison, Kathy Ireland, and Quincy Jones.