Silicon Valley Has a Vulnerability Problem

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.

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.

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.

Coming out of such a traumatic, public failure has been interesting. The old saying “you really see who your friends are” is the gospel truth in times of hardship. I was pleasantly surprised at the amount of awesome people in my life, even those on the outskirts of it.

At the same time as I have worked to “bounce back” and get back on my feet, both financially and emotionally, I have met with many people who see an invisible F carved into my chest: Failure.

And not only Failure. Public Failure. They either come right out and say it, or it’s clear through body language. They choose to define me based on past mistakes, versus what I have learned from them and the successes we did have.

Based on that I’ve been in a quandary. 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: haters, the undecided and friends?

There is a type of founder in Silicon Valley, one who leaves their last company under dubious circumstances yet is still seemingly flush with cash and will answer that they’re “crushing it” when you ask how life is going.

Shockingly, some people assumed this about me after Zirtual flamed out. Many people would suggest I “take a year off and travel.” They definitely meant well, but all I could think of was “with WHAT money??” I couldn’t pretend that my life was going well, but people expected me to.

“Fake it ‘till you make it” is a phrase you hear a lot in sales and startup culture. This type of thinking means that at your most vulnerable point — early in your career, at the start of a new venture, when things are tough — instead of asking for help in an authentic way, you must project an image of success that hasn’t materialized yet.

This happens all the time. Why do you think most people buy nice cars, expensive watches, or an even better example: faux expensive watches. It’s all optics. They want to “seem” like a success. Authenticity and vulnerability get left in the dust when you fake it ‘till you make it.

The problem with faking it is that you miss out on the opportunity to be helped and to help others. Maybe you’re struggling financially and the person you’re chatting with has a job at her company that would be perfect for you, but since she thinks you’re “crushing it” the topic will never come up. Maybe the person you are talking to is going through the same thing, and if they just knew they had a friend in it, they wouldn’t feel so alone.

Speaking from personal experience, I know one of the biggest reasons we “fake it” is because we are scared of what the world will think of us.

We’re broke.

Our marriage is falling apart.

We’re going to lose everything.

We don’t know how to make the next payroll.

Our home is in foreclosure.

Faking it doesn’t change the reality of any of these situations; it only leaves you and others feeling even more alone. But there’s a different option, one that seems “obvious” but is rarely seen in our “success breeds success” world…

The second option, the one I have chosen to embrace, is being brutally vulnerable. This does not come easy for me, at all. I am far more likely to keep people at a distance than to go emotionally “open kimono.”

But that is exactly why I must choose brutal vulnerability. The last decade of trying to ‘John Wayne it’ has worked in some short term ways, but it’s also hurt my health, my relationships, and interfered with my success. Plus, one of the things that drives me the most in life is the desire to inspire others — faking success when you aren’t experiencing it or acting cooler-than doesn’t inspire those around you — it isolates them.

Surprisingly my own fall from grace has brought people out of the woodwork, somewhat quietly, to say “Oh my gosh I went through the same thing. I was just too scared to talk about it”. This is what has encouraged me to be more vulnerable, not less. Because if only one person sees me struggle and feels less alone or is encouraged that they too will make it through… it’s 100% worth it.

A blogger and entrepreneur who is epically transparent is James Altucher. Though I sometimes cringe at exactly how open he is, and don’t necessarily agree with everything he says, I can’t help but applaud the cojones it takes. He doesn’t paint himself as a success that has fumbled a few times, he paints himself as a person who has failed over and over and now enjoys some success.

Opportunity comes to those who open themselves up to the Universe.

P.S.

Lastly, there is one person who has continued to support me throughout this journey and was one of the reasons I got through the writer’s block that was stymying this piece. You know who you are, thank you from the bottom of my heart for supporting me, being a mentor, and most importantly being a true friend.