But today here she is, now 41, in a basic rented office in San Francisco, pouring and doctoring my coffee. A conference table is plopped down right next to the desks occupied by the staff of her start-up, Joyus, which she hopes will become the Shopping Channel of the Internet. It raised nearly $8 million in its first fundraising round. Not for her the slovenly fashion of the Valley—tall, slender and classically beautiful, her outfit is a symphony of greys.
I’m curious to find out why she left the seemingly sure thing of Google behind. “Growing up in St. Catharines, my father and mother ran their own medical practice. He always said to me: ‘Work for yourself.’ It goes deep for me. So when I felt I’d done what I came to do at Google, I knew the next inflection point was going to require me taking another risk.”
Singh Cassidy was among the women featured in a recent San Francisco magazine article about tech’s supposed “Femme Boom,” but the piece turned out to be more wishful thinking than reality, and its central question—where is the female Mark Zuckerberg?—was left unanswered. At every tech event I’m at, men vastly outnumber women.
A high-level female Canadian exec who’s worked with many of the top companies insists we go off-the-record before she begins a rant against the pervasive sexism in this industry. “People ask me, would you encourage your daughter to follow you into tech. My answer is no frickin’ way. I would tell a woman going in, you’re going to be 40 years old pitching a VC in the Valley, and he’s going to pinch your bum. I had that happen to me! ...I got demoted [at a tech company]when I got pregnant. We’re not making progress in tech. If anything, it’s going the other way.” Another woman, a conference organizer, comments: “I feel sorry for the wives. The guys are always working, always out all hours at some networking event. Don’t believe them when they say it’s hard work. They love it.”
But Singh Cassidy is not one for the woman-in-tech question. She shrugs. “Yes, there are more guys—you don’t let that stop you.” Joyus is unapologetically occupying what is sometimes dismissively called the Internet’s pink ghetto, since it’s planning to bring online video into the shopping experience, mainly focusing on commodities of interest to women. “Online shopping could be more of a pleasurable experience, like it is off-line. The video will help take it to the next level.” On her site, a top makeup artist demonstrates how to choose and apply the perfect red lipstick. I’m not the target market, but the demos are stylishly shot—Singh Cassidy’s own personal good taste infusing the site. Joyus might just take.
“You know, you never know,” she says—her accent curiously New York, something explained by her work at an impressionable age for Merrill Lynch in Manhattan, just after graduating from Western’s Ivey business school. “The reality is, starting a company in Silicon Valley is like nothing else in the world. This is a place where capital is abundant. You basically get to live a dream on somebody else’s ticket. At Google, I had lots and lots of people to help execute a vision. Here, well,” she looks around, “so far there are just a few of us.”
Another Ivey alum, Chris Albinson, a managing partner in Panorama Capital, a Sand Hill Road VC firm, joins Singh Cassidy to speak at an alumni event hosted by the networking company Cisco in its San Francisco office. The 44-year-old from Kingston is blunt but thoughtful and often wears a black Arc’teryx shell, indoors and out. He was one of Terry Matthews’s protégés at Newbridge Networks, eventually going out on his own, founding Digital Island, a company that provided secure Internet services to the likes of Schwab, eTrade, Microsoft and Disney. It was sold in 2001 for $340 million to the U.K.-based giant Cable & Wireless.
The investment strategy at Albinson’s firm is “burning the mahogany walls.” He explains that there are many businesses—wood-panelled places like insurance, law firms and publishing—that stand to be disrupted. His firm bets on companies that will use tech solutions to supplant and destroy the old-line ones. He jokes, though, that his investing strategy clearly isn’t foolproof. After all, he could have invested in Facebook. “What can I say? It was run by one guy who was a known drug user and another who was a college dropout. I passed.”