She was most recently the CEO of Google Cloud and a former director of Alphabet, Google’s parent company. Before that, she co-founded and helmed three successful technology companies: In 1998 she co-founded VMware, which went public at a $19 billion first-day closing valuation. She also co-founded and was CEO of VXtreme, a low-bandwidth streaming video company bought by Microsoft; and Bebop, a software-as-a-service (SaaS) startup acquired by Google. She has worked at Sybase, Tandem, and SGI as a software engineer, and she was a naval architect prior to transitioning into the tech industry. Today, she acts as an advisor to a host of organizations: she sits as Chair of the MIT Corporation and serves on several other boards, including Wix.com, Stripe, and AP Moller Maersk.

We were lucky to sit down with Diane to draw on her career-spanning insight for the Zetta AI Founder’s Playbook. This conversation summary is part one of two, focused on her experience leading VMware. The second installment, soon to be published, is about her time as the founding CEO of Google Cloud.

VMware was the first cloud computing and virtualization company — a category-definer for so many reasons. Diane walks us through the unique challenges facing a company presenting a new technology to a nonexistent market, the challenges they faced from incumbents when they got it all up and running, and customer acquisition strategies from the earliest days of what grew to be one of Silicon Valley’s most successful companies.

And, importantly, she explains how close we all came to calling the “cloud” the “elastic sky,” instead. (We sort of wish that had stuck — right along with the namesake company band started by early VMware employees. I won’t not encourage you to search for their old gig videos on YouTube…)

Without further ado: Diane Greene.