The Dark Side of Entrepreneurship

Most successful founders struggle with depression

The Fake Me…

I’ll let you in on a dirty little secret — I’m a hot mess — a condition that isn’t necessarily apparent from the outside looking in. If you were to glance at my Instagram account you’d see a successful entrepreneur with multiple exits, a father of two amazing children, a man with a close circle of friends, and an athlete who rides horses and plays polo several times a week. What you don’t see is the fact that I’m completely unfulfilled when it comes to my career — the one thing that has defined me for decades. Don’t worry, I’m okay, but I things aren’t always as rosy as they may appear.**

It turns out that I’m not alone — scores of entrepreneurs are a hot mess suffering from everything from burnout to depression. This last week I lost a friend and colleague and wished I had told him how much we all struggle. In my case I thrived on startup chaos — the ups and the downs made me feel complete. What I wasn’t prepared for was what came next — after the chaos ends and you’ve exited your startup. We all know people who are incapable of being alone — the folks who bounce from relationship to relationship with scarcely a day in-between. Up until recently I was that sort of person when it came to startups. I always had two three new ideas lined up — I have always been the very definition of a serial entrepreneur. Mark Andreessen describes the thrill of the serial startup rollercoaster,

First and foremost, a start-up puts you on an emotional rollercoaster unlike anything you have ever experienced. You flip rapidly from day-to-day — one where you are euphorically convinced you are going to own the world, to a day in which doom seems only weeks away and you feel completely ruined, and back again. Over and over and over. And I’m talking about what happens to stable entrepreneurs. There is so much uncertainty and so much risk around practically everything you are doing. The level of stress that you’re under generally will magnify things incredible highs and unbelievable lows at whiplash speed and huge magnitude. Sound like fun?

He’s dead on and for me it wasn’t only fun — it was a way of life. Brad Feld talks about what comes after. The dark side when he explains,

It’s not a topic the start-up community understands well. After all, this is the very culture that turned the chestnut “pick yourself up by your bootstraps” into a much-celebrated verb. Admitting you struggle with depression is like admitting you can’t reach your bootstraps. It’s assumed that successful people can just “shake it off.”
But that’s not how it works […] depression carries a stigma. Most of the success stories we hear involve an entrepreneur who pushes himself beyond his physical and emotional limits. He’s unbalanced–but in a good way.
My own experience has made me realize that this imbalance is no way to live the start-up life, and, in fact, it’s detrimental to this kind of work. The only way I survive the dark periods is by constantly renewing myself and my perspective. Starting over is part of the process of starting up. That’s something those in the entrepreneurial community should understand better than anyone else.

In more cases than we’d like admit founders end up killing themselves — especially after they’ve achieved success. For example, Aaron Swartz, Reddit co-founder said, shortly before killing himself,

Surely there have been times when you’ve been sad. Perhaps a loved one has abandoned you or a plan has gone horribly awry. Your face falls. Perhaps you cry. You feel worthless. You wonder whether it’s worth going on. Everything you think about seems bleak — the things you’ve done, the things you hope to do, the people around you. You want to lie in bed and keep the lights off. Depressed mood is like that, only it doesn’t come for any reason and it doesn’t go for any either. Go outside and get some fresh air or cuddle with a loved one and you don’t feel any better, only more upset at being unable to feel the joy that everyone else seems to feel. Everything gets colored by the sadness.

Soon after I turned forty I began to hear of entrepreneurs, like Aaron that I considered friends and colleagues, committing suicide. You rarely read about their deaths in the paper. There are no public funerals. These are people you knew from the conference circuit — events like SXSW and Web 2.0 — they are now just gone and no one talks about it. You would be surprised at just how many successful entrepreneurs suffer debilitating depression that ultimately results in suicide. I know I was. James Altucher wrote in Magic Idea of Math something that really resonated with me,

In mid-2002 I was so depressed I simply ran out of ideas. Depression scorches the earth of your brain. I would sit in it at 3 in the morning in the dark. Lord of my crumbling kingdom. Every day I went a little more broke and there was nothing I could do about it. Going broke is very scary. I would drink to help me sleep. Then I would refuse to wake up. Then the fear would repeat until I fell asleep again. I pretended to smile at my children. I pretended to smile at my wife. People say when you pretend to smile it often triggers happiness because you fool your brain into thinking you are happy. I can tell you: my brain was not fooled. If anything, fake-smiling made me more depressed.

Entrepreneurs live a life of manic highs and depressive lows — what most of us are not prepared for is life after the startup. The way most of us cope is to start yet another company. The time between startups is the danger zone. According to Dr. Freeman, fewer than 7% of adults will experience depression — compared with 72% of entrepreneurs. For entrepreneurs this depression is often a direct result of a lack of purpose. Most of us are dealing with our depression alone — we feel a sense of social isolation unique to startup CEOs — we’re surrounded by people, but we often feel alone. Social isolation is a HUGE risk factor for suicide for startup founders.

Last month I reached out to a friend who had a huge professional and personal setback and I strongly suspected that he was having suicidal thoughts and begged him to seek professional help. I shared my own story and the stories of my friends who didn’t get help — I’m pleased to say he’s getting help. Entrepreneurs are great liars — we’re very capable of telling everyone that everything is “great” all of the time. If you suspect there is more going on with your entrepreneurial friend you need to take a risk and suggest they talk to someone — you’d be surprised how much your words can mean to someone dealing with depression. If you’re looking for ideas to help you might review Prudy Gourguechon’s “Seven Rules to Avoid Burnout & Meltdowns”.


My therapy horses: Bobcat and Cash

Update: Shortly after writing this story a number of my friends reached out to make sure I was okay — I’m okay. Almost two years ago a friend introduced me to horseback riding. I didn’t get it at first, but eventually I realized how therapeutic riding a horse could be. I am a pretty lousy polo player — there are about 4,000 of us here in the United States and I’m ranked right there at the bottom — but when I’m on my polo pony I am not thinking about anything else. My mind is clear and I am completely present — I reach a state of mindfulness — something I was never been able to achieve before. My Buddhist friends reach “sati” through meditation — I achieve it riding a horse. If you’re interested in learning to play polo just let me know — I’m out most Wednesdays, Saturdays, and Sundays.

About The Author

Alexander Muse is a serial entrepreneur, author of the StartupMuse (available on Amazon), contributor to Forbes and Medium. You can connect with him on Twitter, Facebook, LinkedIn and Instagram.