From Sailboats to Startups: Diane Greene’s Silicon Valley
Diane Greene says her favorite experience ever was when, as a young woman, she windsurfed 15 miles from Molakai to Maui . . . alone. That confidence in her abilities and comfort with taking risks has served her well throughout her storied career as a Silicon Valley entrepreneur, leading engineering teams and cofounding multiple startups. These include virtualization giant VMware, which she took to a $2 billion run rate over the course of 10 years. As CEO, Greene took the company public and oversaw its sale to EMC in 2003 for $635 million. Now she leads Google’s cloud enterprise, directing the growth and strategy of a major business partnering with customers like Snapchat, Disney, and eBay, and sits on the boards of Alphabet, Intuit, and MIT. In a July 2017 fireside chat with Exponential Executive Director Marguerite Gong Hancock at the Computer History Museum (CHM), Greene shared her experiences and insights.
Between stints of racing sailboats and windsurfing on both coasts, Greene earned a mechanical engineering degree from the University of Vermont and a master’s in naval architecture from MIT. One of her first projects involved designing a cargo carrier. But, when her boss required her to do calculations by hand rather than on a computer, a fairly new innovation at the time, she quit. And, when she was working for an oil and gas firm in San Francisco but couldn’t go out to the rigs because there were no quarters for women, she spent her time teaching herself to program. Drawn to computing technology and interested in machine learning since her days at MIT, Greene decided to pursue a computer science degree at UC Berkeley, where she focused on databases.
After holding engineering positions at Sybase, Tandem, and SGI, Greene became involved with her first startup in 1995, a low bandwidth video streaming company called VXtreme. She describes how she became CEO by default and, in an understatement, remarks that the company’s purchase by Microsoft two years later was “kind of amazing.”
At VXtreme, Greene says she learned a lot about communication and how people get along and she took those skills with her when she became cofounder and CEO of VMware in 1998. The company brought virtualization technology, which lets servers run many operating systems and applications at the same time, to market on standard commodity hardware. The company grew organically under Greene’s leadership. She relates how she conquered her discomfort with public speaking by conducting an all-hands company meeting every Friday starting with a “friendly crowd” of about 20. By the time there were thousands of employees, she was no longer nervous.
Nor was Greene nervous about taking more risks. She founded her third company, Bebop, in 2013, when she couldn’t convince anyone else to run with her idea for an enterprise development platform. It was bought by Google two years later for $380 million, and Greene joined the company as executive vice president of Google Cloud Enterprise. As the search giant enters a sector dominated by Amazon, Microsoft, and IBM, she has set the ambitious goal to lead the cloud computing market by 2022. She says it’s “amazing” running Google Cloud in the midst of a “revolution” as companies move their business to the cloud. It’s a revolution on a huge scale: Greene notes that Google has spent $3 billion a year on Cloud for the last three years; has built hundreds of thousands of fiber-optic cable under the world’s oceans; and serves two trillion searches and a billion hours of YouTube watch-time a day.
Greene is particularly excited to be collaborating on projects using artificial intelligence and data analytics and working with, as she says, “cool companies.” She’s pleased that Cloud helps small companies like Indonesia’s motorcycle ridesharing company Go-Jek succeed when they scale. Greene offers her insights into what it’s like to try to offer companies around the world the same services in a complex geo-political landscape.
Despite these challenges, Greene is excited about the AI revolution that is allowing her team to build Cloud’s capabilities for customers and using it themselves to make Google’s buildings greener.
When building her team at Google, Greene focused on the need for diversity, noting in particular that unconscious bias can get baked into AI if developers are not careful. Though she personally has not had negative experiences being a woman in engineering and tech, she believes it is important that Silicon Valley is addressing gender discrimination. For her part, Greene seeks to foster a safe and supportive work environment where people feel comfortable speaking up. Reflecting on advice for new entrepreneurs, she attributes her own success to lessons learned from sailing.
If her advice for starting a company can be summed up in one word, Greene believes that word is “tenacity.” She advises entrepreneurs to keep in mind where they want to go and why and to be tenacious about getting there. Recruit great people by sharing a compelling vision, she says, and provide a work environment and culture that is stimulating and makes people feel excited to show up every day. And then let them run . . . or perhaps sail.
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