Chapter 3: All press is not good

…the time my CEO posted a video of someone else’s private bits

Listen, if you weren’t around the tech startup world in mid-2013, you really missed out on this gem, but don’t panic.

I was there. I remember. So does my family because when the story broke, I was with them. At dinner.

It was an experience that has truly shaped my entire career and here is what I can tell you, without question nor hesitation:

All press is NOT good.

I’ll say it again for the people in the back: ALL. PRESS. IS. NOT. GOOD.

I once read somewhere (or maybe heard on TV…)someone say that all press was good press and nearly screamed at an inanimate object because I was deeply triggered by the lies being told.

Until you experience press like your CEO posting private bits of a client all over his own social media as well as the company’s, you can’t truly relate to the emotional response I get to hearing people insist that all press is good. If you looked up one sunny Sunday afternoon and saw a video of a naked client as the result of your CEO’s partying in India, I ask you — what would you do?

For a quick summary (you can read more on it here): a CEO I worked for traveled to India with Google but went early to “celebrate” Valentines day with one of his then girlfriends. He went to the beach, partook in some mind altering substances, pulled out a camera (probably his phone, iPhones were around then yea?), filmed a then client naked on said beach, and then posted the video all over the internet. This wasn’t just any kind of video but said client had lost all clothing for the feature film and, my favorite part, said CEO recorded himself with this one liner takeaway “If you’re gonna get naked, you gotta have a big ass dick, what’s going on?”

Yes, you read that correctly.

Do I need to remind you that he then posted it all over his and the company’s social media?! All of them. Every. Single. One.

Accounts that I didn’t even know existed got a front row seat to this feature film. Let me remind you of the times — Instagram was an infant; baby boomers had just entered the world of Facebook; Snapchat was something people were still trying to figure out. I’m not gonna lie, I didn’t even know what Snapchat was at this time. It was around. I suppose. Regardless of their status, all social accounts got this rare work of art and all shut down our accounts due to probably what helps TikTok define its “community guidelines” now.

Back then, my assumption, once my CEO awoke from whatever mind altered state he’d been in the previous day, would be that he’d be mortified and would be working on a deep crisis management PR plan. He wasn’t and he didn’t. His response to our team wide breakdown in the USofA was “all press is good press”.

He then hung up, moved on, and continued on his trip until Google kicked him off due to “misconduct”. Go figure.

I wish that I was exaggerating and if I didn’t live it, I would think this story was completely made up. The saddest part, by this point in my 9 months at this company, I wasn’t even surprised. I had a split second where I thought, “how”, but it was quickly replaced with “of course this is happening”. The lack of surprise was the largest indication that ever single red flag had presented itself in my 9 months here and this, despite what it may feel like, was actually just the straw that broke the camel’s back. It, alone, did not destroy the company. A reality that is truly sad to say out loud today.

But here are some indicators that helped me understand why this situation wasn’t all that surprising to me; the indicators that should have had me running for the hills within my first 30 days:

🚩On my first rounds of interviews, many team members referred to the CEO as the “dragon”= PROBLEM

🚩On my first coffee date with a co-worker they warned me that the CEO would threaten and use scare tactics such as firing people for small mistakes as his way of “management” but don’t worry, he’s much better “in person”= PROBLEM

🚩The reality that I did get fired, weekly, for no reason, while really helping me develop a tough skin… = PROBLEM

🚩The fact that we only knew when the CEO was at our HQ by the smell of marijuana first thing in the morning and most would avoid the office when he was around= PROBLEM

🚩The reality that when the CEO made a mistake it was everyone else’s fault, never his = PROBLEM

🚩The fact that the CEO made “ghost accounts” in our project management tool in order to “spy on employee’s work” and everyone knew yet said nothing= PROBLEM

🚩The realization that the focus was always on the external ‘image’ never on the internal team= PROBLEM

🚩And perhaps the biggest red flag, when the COO planned her exit with no future plans to be tied to the company she helped build from the beginning= PROBLEM

I look back on my time at JESS3 and think to myself…how could I have missed the red flags? The answer, I didn’t know they were red flags. I was young and inexperienced. It’s not an excuse but if you don’t know, and it’s your first “big kid job” then you may think this is how it is.

Which I did.

But I’m here to tell you, it isn’t.

The epic way in which we ended at JESS3 was a catalyst in a lot of things in my life, so I can’t say that I regret seeing the demise take place. As a junior level employee, I saw some terrible leadership and not just from the CEO; I saw and witnessed the worst ways to handle some really intense HR issues (PS there was no HR business partner here…and it was needed); I got a front row seat in the book “How to destroy your own company”; so I don’t regret it.

Because it led me to where I am today and helped define what kind of leader I didn’t want to be; what kind of businesses I don’t want to help build; the kind of leadership I would never work for or with again.

I’m not sure if I could have had worse in a short 9 month period (one day I’ll tell you about the time he told me and all the workers of United Airlines to “kill themselves” because he overslept and missed his own flight) and after a short life crisis which resulted in working at Starbucks for 8 hours (another story…), I moved to NY.

And that result was worth it even if I still cringe and cry, just a little bit, anytime I hear someone say “all press is good”.