CEO and co-founder: Ruba, Xfire, Direct Hit, Stylus Innovation
Current title: Director of Product Management, Google (which acquired Ruba in May for an undisclosed sum)
Education: B.S. and M.S., aerospace engineering, MIT; MBA, Harvard Business School
Member: Visiting Committee Board, MIT Media Lab
Twice was the charm for Steve Jobs (Apple and Pixar) and Marc Andreessen (Netscape and Loudcloud). Jim Clark achieved a trifecta (Silicon Graphics, Netscape, Healtheon). But four times?
Mike Cassidy is living proof. Consider him the Start-up King of Silicon Valley. In short order, he co-founded and was CEO of four companies — Ruba, Xfire, Direct Hit and Stylus Innovation — that have been sold for more than $600 million to the likes of Google, Viacom and Ask Jeeves.
"I'm an impatient person, and I'm fast," says Cassidy, who recently joined Google (GOOG) after it snapped up his latest venture, online travel guide Ruba, for an undisclosed amount in May. "There is a start-up mentality here," Cassidy says of Google.
IIn a recession-tinged era of few high-tech initial public offerings, where many start-ups fruitlessly seek buyers, the forty-something Cassidy has been able to quickly create and sell companies.
And he's probably not done.
"He's not lucky. He's skilled in finding opportunities and coming up with a solution," says Warren Packard, an investor in Cassidy's second, third and fourth companies.
Packard has known Cassidy since 1987, when they both worked on a solar race car. They reconnected in 1998, when Cassidy started Direct Hit and Packard was a partner at influential Silicon Valley venture firm Draper Fisher Jurvetson. Cassidy approached the firm for funding.
"He had to convince more than me," says Packard, who is still at Draper. "But he was concise, convincing and informal. He moves fast."
Cassidy landed a $3.5 millioninvestment the same day.
"Next to Mike, I am bush league," jokes Trevor Traina, another serial Silicon Valley entrepreneur who has sold two e-commerce companies — CompareNet (to Microsoft for $100million) and StepUp (to Intuit for $62 million) — and is working on his third, DriverSide.com.
"Every time I turn around, he has sold another company," says Traina, who, with Cassidy and other local tech CEOs, meet once a month at dinner to discuss business.
Adds Yelp CEO Jeremy Stoppelman, another dinner participant, "Most entrepreneurs in the Valley would count themselves lucky to have just one successful outcome, yet Mike's created value over and over again. Few people in the Valley are as tenacious and tireless. He's intense."
Speed, speed, speed
Cassidy's start-up track record is short and sweet. Besides a 500-day rocket ride for Direct Hit, it took about two years for Ruba and 2½ years for Stylus. Xfire required three years, but only because Cassidy scuttled its original business plan as Ultimate Arena, a place where online gamers could enter tournaments or play one another for money.
Avatar director James Cameron takes longer to make a movie.
"Any average chess player can beat the best player in the world if they get to move twice for every time the grandmaster moves," Cassidy says, drawing an analogy.
"Mike just gets things done," says Angela Strange, former vice president of product management at Ruba and now a product manager of games at Google. "He does not waffle, is decisive and well-informed, and he is super, super responsive."
Cassidy created:
•Stylus Innovation, which produced computer-telephony software. It was sold to Artisoft for $13 million in 1996.
•Direct Hit, an Internet search engine whose customers included MSN, Lycos, AOL and dozens of others. It fetched $532.5 million from Ask Jeeves in 2000.
His head-spinning feat at Direct Hit — from start to sale — earned him the moniker of "$500 million in 500 days."
•Online gaming community Xfire, with more than 15 million registered members in 100-plus countries. It went for $110 million to Viacom/MTV in 2006.
•Ruba, which he recently sold to Google.
Perhaps the eclectic mix of start-ups merely mirrors the diverse background of Cassidy, who studied jazz piano at the Berklee College of Music but earned a B.S. and M.S. in aerospace engineering from the Massachusetts Institute of Technology and graduated from Harvard Business School.
Cassidy serves on the visiting committee board of the MIT Media Lab.
Perhaps, too, Cassidy's varied career is a reflection of his father's career.
After teaching political science at the U.S. Air Force Academy and University of Denver, Paul Cassidy was a civil servant in a wide range of capacities, including a Defense Department liaison at the U.S. Embassy in London and a nuclear-weapons negotiator with the Soviets in the 1980s. Paul Cassidy is now retired.
"I did caution him that the chances of each successful start-up diminishes," says Paul Cassidy, ever mindful that even venture-backed companies have a 1-in-10 chance of succeeding.
Pulling off four winners in a row, at those odds, is a 1-in-10,000 chance, Paul Cassidy says.
Though Mike Cassidy has wanted to work at Google for "a while" and is happy there as director of product management, where he oversees search operations, it's a matter of time before he embarks on his new challenge, Traina and otherssay.
"Nothing would surprise me — whether he stays here or does another company," Strange says.
So, what's next? Cassidy says he's intrigued by location-based mobile services and video search, for instance.
Could the fifth time be another charm?
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