The Sideways Path to Scale — with Diane Greene of VMware and Google

Some entrepreneurs start their journey with a detailed plan that they follow to the letter. Jeff Bezos, for example, always had a plan for how Amazon would leverage the infinite shelf space of the internet to become the “everything store.” Or consider that in 1980, when Studs Terkel asked a young bodybuilder named Arnold Schwarzenegger what he planned to do in his career, the young Austrian immigrant replied that he planned to leverage his bodybuilding success to become an actor and then go into politics. Most of us, however, have to keep revising our plans along the way. A scalable idea rarely sits squarely on the path ahead. It’s always scurrying off to the left or the right. And if you can’t get your team to adjust course quickly, it will slip out of sight. That’s how Diane Greene started VMWare and laid the foundation for cloud computing.

In today’s Masters of Scale podcast, Diane and I discuss how she, her husband Mendel, and his graduate students co-founded VMware. You’ll hear how, on the one hand, Diane never thought about building a billion-dollar company, and how, on the other hand, when VMware had only 10 employees, she told her new office manager/COO V.J. Richey, “V.J., this technology is going to run on every computer system in the world someday.” That’s precisely what happened, even though, at various points along the way, Diane had to struggle to find customers other than college science professors, and put up with the pity of entrepreneurs from hot companies like and WebVan (They felt sorry for someone working in “software.”

You’ll find out how those professors — along with bankrupt Dot Bombs looking to save money and Linux developers who needed to check their email — helped Diane grow VMware into one of the world’s most important technology companies. You’ll also learn how her experiences as a national champion sailor made her a better entrepreneur, how Bill Gates inadvertently helped convince Diane to start the company, and the one condition she gave Google before accepting its offer to run its Cloud business.

As always, I’d like to hear your thoughts and reactions to this episode. What’s a scalable idea that came at you sideways? What’s a scalable idea you missed because you were too determined to keep forging straight ahead?

Please write a short post on your LinkedIn newsfeed to share your answers with the wider community. Tag your post #mastersofscale so I can find it. And if you’d like, Tweet it at me (@ReidHoffman) and @MastersOfScale.