Interview, Fireside Chat
VMware Cofounder Diane Greene with Jessica Livingston at the Female Founders Conference
- Diane Greene co-founded VMware in the late 1990s alongside her husband (a Stanford professor) and two graduate students, initially conceptualizing the company after her husband received an email regarding a Microsoft-referred blind review paper on virtualization.
- The founders faced significant skepticism during the dot-com era; a potential investor dismissed the technology as "hopeless," and the team struggled to hire business-side personnel or secure public relations firms.
- Early funding was secured through a "friends and family" seed round totaling $300,000, led by Andy Bechtolsheim and David Sheridan.
- Bechtolsheim provided capital via a check left in his driveway, a decision made in approximately one hour after the founders explained the technology, noting his history as a seed investor in Google.
- Greene raised follow-on funding from Dell and several banks, maintaining total voting control of the company without issuing dual-class shares or 10-to-1 voting rights.
- During VMware's early infancy (circa 1999-2000), the team operated out of a small building near Town and Country known as the "Crack House" due to adjacent illicit activities; Greene brought her infant daughter to work and utilized a high-end nanny while traveling for global sales.
- Greene identifies her primary strategic mistake as initially considering a sale of VMware to co-founders who wanted to exit, a decision she reversed to retain leadership and spend time with her children.
- After leaving VMware, Greene served on the boards of Intuit and Google, noting that while these companies differed culturally, they shared a focus on high-caliber talent and unique board dynamics.
- At Google, Greene was the third woman on the board, joining Shirley Tilman and Ann Mather, a composition she credits for enabling distinct governance conversations.
- In 2012, Greene founded Bebop (Bebop.ai) in stealth mode to address the complexity and poor user experience of enterprise software, aiming to leverage machine learning to automate workflows and reduce screen clutter.
- The Bebop co-founder left shortly after the company was launched; Greene subsequently brought in former VMware colleagues to fill the void, effectively acting as the sole active founder for a period.
- Google Cloud approached Greene regarding potential partnerships after she joined their board; the integration of Bebop's capabilities with Google's AI and infrastructure was driven by her personal relationship with Google employee #8, Urs Hölzle.
- In 2017, Greene sold Bebop to Google; the company had recently raised a significant round of funding from Andreessen Horowitz (a16z) with Mark Andreessen on the board.
- a16z was reportedly unenthusiastic but supportive of the sale, allowing the deal to proceed without obstruction.
- Greene projects a future cloud infrastructure market consolidation into approximately four major providers, citing a $10 billion annual enterprise spend and the difficulty of disrupting established players without quantum computing innovations.
- She cites the cloud's superior security model as a primary driver for enterprise migration, noting the ability to update operating systems constantly and monitor over 1.2 billion users for threats like ransomware in real-time.
- Greene advises first-time founders to select board members based on specific, unique expertise required for the venture rather than general prestige, citing her recruitment of Larry Sonsini to manage complex deals with Intel and Microsoft.
- She recommends treating the board as a collaborative resource to be trusted, noting that she never prepared slide decks for meetings but instead provided documents outlining challenges to be discussed, fostering a relationship where she did not need to "impress" directors.