Aug 4, 2017 · 24m · y-combinator
VMware Cofounder Diane Greene with Jessica Livingston at the Female Founders Conference · Y Combinator
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
At the Y Combinator Female Founders Conference, YC co-founder Jessica Livingston interviews VMware co-founder and former Google Cloud SVP Diane Greene about her entrepreneurial journey, boardroom governance, and balancing family with scaling tech companies.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
The partners as informed peer 1.9 Guest teaching 2.9 Guest disagreement 1.6 The partners pushing back 1.1
speaking balance: gold is the partners, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 20:10 Rejecting mistake framing
Diane directly dismisses Jessica's question about what mistakes first-time founders are going to make by saying they might not make any.
Hardest push from the partners ▶ 20:13 Insisting on learning the hard wayJessica pushes back against Diane's dismissal by insisting everyone makes mistakes and rephrasing the question as lessons learned the hard way.
Biggest teaching moment ▶ 20:25 Masterclass on board managementDiane educates the audience on running slide-free board meetings based around genuine founder concerns rather than managing or impressing directors.
The partners hold their own ▶ 2:32 Summarizing the dot-com era IPO frenzyJessica displays her familiarity with the dot-com era dynamics by synthesizing the market environment and probing Diane on equity.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The partners as informed peer | Guest teaching | Guest disagreement | The partners pushing back | Why |
|---|---|---|---|---|---|---|
| Founding VMware and Early Silicon Valley in 1998 | 2 | 2 | 1 | 1 | Jessica Livingston guides the conversation with friendly questions about late 90s Silicon Valley. Diane Greene recounts building VMware as deep technology while skepticism surrounded non-consumer tech during the dot-com bubble. | |
| Balancing Startup Life with Motherhood & Early Office Setup | 2 | 2 | 1 | 1 | Jessica asks about the early days balancing early motherhood with startup funding. Diane shares anecdotes about early angel investors like Andy Bechtelsheim writing checks without VC involvement. | |
| Raising a Child While Scaling VMware Globally | 2 | 3 | 2 | 1 | Jessica inquires about mistakes made at VMware. Diane reflects on feeling pressured by co-founders to sell the company, explaining they were entirely in control because they had avoided institutional VC funding. | |
| Board Experience at Google and Intuit | 2 | 3 | 2 | 1 | When asked what Google and Intuit boards have in common, Diane quickly clarifies that few companies compare to Google. She also explains the dynamics of female representation on the Google board. | |
| Product Vision for Next-Generation Enterprise Software | 2 | 3 | 1 | 1 | Diane explains the clunky state of enterprise software that prompted her to start Bebop and how it eventually merged into Google Cloud after building relationships with Urs Hölzle. | |
| The Cloud Revolution and Security Infrastructure | 1 | 3 | 1 | 1 | Diane monologues on the macro scale of cloud infrastructure and how high capital requirements and advanced security vigilance concentrate the market into just a few major players. | |
| Advice for Founders on Building an Effective Board | 2 | 4 | 3 | 2 | Diane initially resists Jessica's premise that all founders will inevitably make mistakes before pivoting to masterclass advice on building and leveraging a trusted board of directors. |
Statements from this episode (11)
Greene: VMware easily attracted engineers, but struggled to hire business talent
“It wasn't that hard to get engineers, because we were such deep technology, they understood what we did, but getting business side people was pretty much impossible.”
Diane Greene: Founders should target wealthy investors with deep domain expertise
“And this is sort of advice I've always given people is, you want to find investors that really deeply understand what you're doing. And so, and you want to get rich people that deeply understand what you're doing.”
Greene managed global travel by hiring hotel nannies for her daughter
“Like, when we got more advanced and started having customers and partners all over the, you know, selling all over the world, ah, she went all over the world with me, and then I would just stay at a really high-end hotel and have them hire a really high-end na…”
Greene: VMware cofounders would have thanked her for not selling to EMC
“My co-founders wanted to sell, and I thought it would be selfish not to, although they would have thanked me had I not”
Greene: VMware raised from angels, Dell, and banks instead of VCs
“Well, we didn't have VCs. So, you know, we didn't have VCs. So I took money after, after we took the money from Andy and David And John, we, ah, we raised money from Dell, and from Dell and a few banks that were wanting to take us public.”
Greene: Having three female board members makes a huge difference over two
“And so I'm the third woman to join that board, which is, it makes a huge difference to have three instead of two.”
Marc Andreessen joined Bebop's board shortly before its acquisition by Google
“Yeah, we had just raised a lot of money from A-A-A-X-Teen-Z, and Mark had joined my board.”
Greene: Enterprise tech will consolidate into four clouds immune to startup disruption
“Everything's going to be in just a few, maybe four clouds or so, you know, there's not going to be that many of them, because like, we spend about ten billion a year in infrastructure, and so it's not going to Get disrupted by a startup, unless they invent qua…”
Greene: Google spends about $10 billion annually on infrastructure
“We spend about ten billion a year in infrastructure”
Greene used written memos instead of slide decks for VMware board meetings
“My board meetings, I never wrote slides, I just wrote a document, and it had a few metrics about how we were doing, if, you know, we were doing well, but the whole rest of it was things I was worried about or trying to figure out.”