Silicon Valley has a vulnerability problem

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A few of us sat in a swanky restaurant, the air was warm and smelled faintly of the honeysuckle growing outside. Glasses clinked on the patio and a group of dilettante’s tittered over a handsome young waiter’s joke. The general mood of the place felt like a modern day Gatsby party… except to me. I was trying to keep my breath steady as a deep, angry blush crept up my neck as the man across from me continued…

“Well, I just don’t know how you could have made those mistakes, being CEO. I am a CEO now and I would never let that happen.” he said.

Breath in, breath out. I nodded, shrugged my shoulders and after a long moment responded, “I guess you’re a better man than me.” The table nervously laughed and I mentally checked out until the dinner was over.

I had been brought out to discuss joining this CEO’s company for some contract work. Over the past few days I had surveyed the company, talked to employees, and put together a detailed list of recommendations. There were a lot of “easy fix” problems, but all in all the growth challenges were ones that could be handled as long as a strong culture and focus on community was in place.

But I had made the critical error. At dinner, someone asked what I would do to improve worker efficiency, I answered honestly. As I talked I could see the CEO’s face change, he was taking my feedback as a criticism of his leadership… I realized too late that I was dealing with an insecure, “alpha” male (the worst type). So before I had time to swallow a sip of red wine, he fired back a reply aimed to hit me where it hurt.

“…I just don’t know how you could have made those mistakes.”

In Silicon Valley, admitting mistakes and showing your vulnerable side is one of the biggest social faux pas that I’m tired of trying to follow.

The fall out

When I left my last company, there was very public fall out. I personally avoided social media/news and most forms of communication for over a month. Though the failure of Zirtual happened because of several contributing factors, including not having a full board, moving from contractors to employees without fully understanding the financial impact and bringing on a negligent “outsourced CFO firm”, at the end of the day the failure was and is my fault.

I was CEO, and even though I did not enjoy the public flogging — I got it. There was no malintent in the way things happened. Actually our intent was only the best; the business was my and my cofounders’ baby and the people we employed meant the world to us.

When things went south and we had to lay off over 400 people, it nearly destroyed all three of us. But as they say, the road to hell is littered with good intentions. I should have hired for my weaknesses far earlier on. I should have asked for help more often. I should have pushed back when advisors and outsiders encouraged growth at all costs. I didn’t. The business failed, hurt a lot of people and caused a ton of fall out for all involved. At the end of the day, as the CEO, I have to own that.

 Do I fake it until I make it and act like things are going swell, or do I be brutally vulnerable in view of everyone?

The two fold path: faking it until you make it or brutal vulnerability

Brutal vulnerability