Blood, Fyre and Psychopaths: Why You’re Wrong About Startup Disaster Stories

“Can we start calling her [Holmes] ‘The Silicon Valley Psychopath’?”
“Finished reading ‘Bad Blood’ and no doubt Elizabeth Holmes is a sociopath”
Billy McFarland is a sociopath, this guy is an asshole, and almost everyone who was involved in Fyre fest is an absolute idiot”

I am not a psychiatrist. I don’t know Elizabeth Holmes or Billy McFarland. I don’t have a clue if these claims are accurate or not. What I do know is that if Elizabeth and Billy are psychopaths, sociopaths, idiots, or assholes, then I guess, I might be too.

The feedback to this recent wave of Hollywood-ized dumpster fire stories is very interesting to me. And not because they are reacting to sensational antics and unbelievable behavior. The most interesting part is what the general public’s response says about them. Let me explain.

I am an entrepreneur.

Don’t read that as braggadocios. That’d be like bragging you have ADHD or can’t feel pain. It might be helpful in certain acute situations, I suppose, but it certainly doesn’t guarantee a fun ride in life.

Being an entrepreneur is similarly a physiological condition.

Smart people have long studied the minds of entrepreneurs. One of the only things that virtually everyone agrees on is that we’re kind of insane. But the level of insanity is hotly debated — at one end, simply loving the risk / reward game, to actually being straight-up sociopaths. The other key debate is where the basis of the entrepreneurial mindset is created.

I’ve had the pleasure to meet hundreds of entrepreneurs over the years. From young kids hustling on their first gig, to some of the most famous names in the game. I’ve met countless millionaires and billionaires, many of whom started with nothing. While many of these meetings were surface-level at best, I have have also been able to spend countless hours with some of them, in private settings, getting deep insight as to their personality, psyche, motivations and purpose.

It’s fun to say we’re all nuts, but with a lot of what I’ve observed, it goes beyond being cheeky.

It seems entrepreneurs are on a never-ending quest to create imbalance in what should otherwise be a balanced life and world. We look at normalcy, routine, stability and zen as negatives, and seek ways to create lives of systemic chaos. Our businesses are the mechanisms to achieve this disequilibrium. There is no better example of this than what happens after an entrepreneur gets rich off a business at a young age. The world has opened its doors to any life you want to lead — one of luxury, comfort and purpose. Instead, the vast majority throw huge amounts of their newfound wealth in to risky ventures, going headfirst back down the rabbit hole.

There are a ton of studies which talk about how many psychopathic, masochistic or delusional characteristics we have. My gut instinct is to say that isn’t true. We aren’t actually crazy. But then you really think about it. We’re forced to create artificial personas that pretend everything is fine when it isn’t, live out compounding levels of lies, gleefully take high-risk bets with the odds stacked against us, and we do this all willingly, over and over and over and over again. We also clearly have some attraction to the pain it is going to cause. Either by way of other’s accounts, or having personally been through it before. Some “serial” entrepreneurs do this dozens of times in their lives, and I can assure you, it never gets easier or less painful.

But with that said, one of the defining characteristics of a psychopath is a lack of empathy and emotion. Us entrepreneurs are generally the opposite — wildly sensitive and introspective. You need a high-level EQ to make it in this game.

A huge swath of us have or had issues with our mental health. 60% more than the general public. From standard-grade depression and anxiety to debilitating personality disorders. Some argue these ailments are what drive us to be entrepreneurs. Perhaps the ups and downs helps to offset our depression.

“But, they’re CrAzY!”

The isolation and lack of nuance in the public’s feedback to stories like Fyre and Theranos speak volumes about the current toxic environment of entrepreneurship. We have been fed a constant stream of bullshit for decades positioning successful entrepreneurs as superheroes, Gods and geniuses.

Flawed, only in the best ways. Human, but better.

This delusion has created one of the most unbelievable and damaging hamster wheels in history.

Entrepreneurs feel pressured to uphold this image, because it makes us look smart and powerful, so we hype our claims, lower our voice, puff our chest, puff up some numbers, smile while taking stupid bets, and thrive in the glow when our “insane” behaviors reap rewards.

That reward comes in the form of venture funding, press, awards, clients, revenue and success. Positive Reinforcement and Operant Conditioning in a nutshell.

This is why us founders can spew flat out lies during a pitch and not feel a wince of pain. Why we smile and tell our team that everything is amazing, while the house is burning down. Why if you put 100 entrepreneurs in a room, everyone is “crushing it!”, even though we all know that 99 of them will be out of business soon. What a statistical anomaly!

We end up believing our own bullshit, further blurring the lines between what is real and not. We exist in a perpetual Reality Distortion Field.

This is the manifestation of Fake It Til You Make It — the most stupid and dangerous idiom in business. Think about what that really is saying. ‘Fake’ is defined as “a thing that is not genuine; a forgery or sham”. One of the most common sayings in business literally tells us to commit fraud until we make it.

And you wonder where Elizabeth Holmes and Billy McFarland come from?

When you reward people for lying, they are going to lie.

When you reward people for being greedy, they are going to be greedy.

When you tell someone they are invincible, they will act invincible.

When I read these stories and watch the salacious documentaries, I don’t think “wow, what a psychopath”. I am actually not surprised by a single thing I see. Rather, I see a mirror being held up to a global epidemic, and a few extreme examples of being on the wrong side of fortune.

Frankly, I am far more surprised when I watch yet another Hollywood business success story, and think to myself “people actually believe this crap?”

The Unpopular Truth

Holmes didn’t set out to commit wire fraud, rip off investors and put patients at risk. She intended to change the healthcare world.

McFarland didn’t set out to abandon Instagram models on an island and commit fraud. He intended to throw a great party.

Now did they fuck up really bad in those pursuits? Yes! But in both situations, only a few things would have needed to change for the story to end up differently. The difference in the taglines of “billionaire” and “felon” are sometimes a tiny, fragile line.

Here is the truth: we entrepreneurs all do the same shit. We don’t all commit felonious fraud and scam people out of billions of dollars. (I can confidently say I have never broken the law in any company I have run.) But, I certainly toed the line of ethics. I certainly puffed up numbers and claims to bolster my story. I certainly made a few bets I absolutely shouldn’t have, that could have gone very, very badly. I looked people who trusted me in the eye constantly and told them everything was fine, when it wasn’t. I lied to myself, and the world, to maintain my image.

How many Silicon Valley startups would survive an in depth Wall Street Journal investigation? How many companies have been in perilous situations, or on the wrong side of the legal line, but were able to fix the situation before anyone found out?

Would we have Uber, Tesla, Snapchat, Airbnb, Facebook or Google if they had a lie detector hooked to them during their growth cycles?

The list of companies who played the same game of Russian Roulette as Theranos and Fyre, but fixed the problems before they were caught, is long. I know of a bunch. I won’t call them out by name, but everyone in the game knows.

In no way am I defending Holmes, McFarland, or anyone else. I doubt I would enjoy either of them as people. Nor am I making any claims about what they are, or aren’t.

I am here to explain why they exist. The culture that created them. And the nuance of today’s toxic entrepreneurial landscape. Like with most problems, the first step is understanding.


I’ve recently finished a book about my entrepreneurial journey (publishing this year, click here if you want an early copy). Unlike other business memoirs, this one is raw, dark, hyper-honest and pulls the blindfold off of a number of topics that we aren’t really supposed to address, like what I talk about above.

Let’s create a conversation. Tweet this. Catch me on Twitter and Instagram.