Failure, Fighting: Crosby's Keys to Success in the Virtualized World

• By Bruce Hoard
• 09/01/2011

It would be a gross distortion of the truth to say that Simon Crosby revels in failure, embraces conflict and works with a whole bunch of people who are smarter than him. Or would it? Actually, quite the opposite is true. Crosby, who recently left Citrix to cofound a new cloud security company named Bromium, would be the first to proclaim his allegiance to failure, conflict and relying on people who are smarter than him.

To him, failure is much more than a learning experience; it's a propellant that incinerates bad outcomes and supplants them with powerful new beginnings. Crosby is passionate about this behavioral cycle because, as a founder of startups such as CPlane and XenSource, he has come to understand the benefits of getting it wrong the first time.

"One of the most beautiful things about the startup world is, if you create an organizational culture that values failure as much or more as it does success, then you have the opportunity to move faster and produce better technology," he says.

For Crosby, fighting -- not just disagreeing, but rolling up your metaphorical sleeves and slugging it out emotionally -- is the key to sustaining the high energy that startups require to stay focused on the path of commitment. As an example of this ideological combat, he recalls a battle royale that raged at XenSource when the CEO and CTO were locked in conflict.

"Nobody was evil, everybody was rational in their own context, and it almost brought the company to its knees," Crosby remembers. "There was a very, very dark moment when this beautiful thing called XenSource could've just died. That was due to people and an inability to build and have a culture where fast-fail and move on was the first order of the day."

Despite the relative value of failure, however, there's only so much any company can process, and he works hard to promote success by exposing the maximum amount of information to the "many" people who are smarter than him. This kind of self-effacing style may seem incongruous coming from anyone so accomplished as Crosby -- who, of course, realizes that in many organizations he'd never find anyone who could match his combination of experience and intelligence. Even in the super-smart company he keeps, the concept of him as some sort of intellectual layabout is nothing less than laughable.

Dig a little deeper, and the roots of this egalitarian attitude reveal themselves: Crosby claims to be ego-free, an assertion that many might characterize as narcissistic nonsense. As he puts it, "There's no ego in anything that I do. I love to see everybody just succeed, so for me that ultimately means the way that I can work with people better is if they know me as me."

Crosby has crossed swords with many detractors who no doubt scoff at what they perceive as his allegedly selfless declarations and unsustainable, pro-Citrix views, but he fights a valiant battle, and his dedication to open source efforts such as Rackspace OpenStack -- which is supported by some 50 companies -- doesn't come off as self-serving or, for that matter, egotistic. He views his public battles as an essential element in his strategy to bring technology to the people by making sure they understand it. In his mind, if that means he appears brash or otherwise offensive, well then, tough bananas.

Crosby recently warmed up to an old foe, saying: "I was at Structure last week and happened to end up speaking with Paul Maritz, who's a fabulous guy and a fellow South African, and we officially buried the hatchet in the sense that I have no ax to grind vis-à-vis VMware."

Not that he's writing off VMware just yet. "I have a single goal with regard to VMware right now," Crosby says, "which is to recruit some of their best employees, because we have an office just down the road from them in Cupertino."