Mental Health: Entrepreneurs Living on the Edge


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Jason Bailey, Eastside Games | BCBusiness
Image by: Adam Blasberg
Jason Bailey credits ADHD for his inability to listen to people, his unhappiness and his remarkable entrepreneurial success.

Successful entrepreneurs aren’t like most people. They’ve made their mark in the world because their thought processes don’t follow predictable paths. But at what point does “thinking outside the box” become a mental disorder? Local entrepreneurs who have skated close to that thin line share their stories

“I didn’t actually listen to you,” says Jason Bailey, well into our conversation. It’s not just me, he says. He does it with everyone, including his wife. We are already 20 minutes into our meeting, but we have only just sat down. We grabbed a coffee at the local hipster café, where he got distracted by two colleagues he met there, and as we meandered back to his trendy Gastown office, our conversation had pinballed between multiple subjects: bitcoin, Gastown, the election, healthcare and more. Now, sprawled on a couch in jeans and an old grey hoodie, he is giving me as much attention as he can muster.

We’re surrounded by about 50 people busily working on the next product for video gaming company Eastside Games Inc. and the 41-year-old founder and CEO tells me that he’s the smartest guy in the room.

“I generally know what someone’s said before they’ve finished,” he says, which is one of the reasons why it’s hard to stay focused. He’s naturally a fast mover, flitting between subjects just as easily as between companies. Bailey, who suffers from acute adult attention deficit-hyperactivity disorder (ADHD), says that he’s always focused on the latest, shiny thing. ADHD, also sometimes called hyperkinetic disorder, or HKD, is recognized by the American Psychiatric Association; it’s also sometimes referred to as Attention Deficit Disorder (ADD), without the “hyperactivity” tag.

Bailey isn’t alone. Many entrepreneurs harbour symptoms of mental disorders, ranging from the mild to the extreme. Natural outliers, they’re driven by mental processes outside of the ordinary. Many good entrepreneurs are counter-intuitive, crazy-like-a-fox mavericks. As the famous Apple ad campaign suggests, they simply “Think Different.” But are there downsides to that abnormality? Are entrepreneurs predisposed to mental illness?

ADHD is common among entrepreneurs and several high-flying ones have identified themselves as sufferers. Alan Meckler, chair and CEO of Jupitermedia, and Kinko’s founder Paul Orfalea suffer from ADHD. Charles Schwab has it, as does David Neeleman, founder and CEO of JetBlue Airways. Successful entrepreneurs like these are driven and relentless and, for many, the very act of starting a business is irrational. They live, as Marie-Helene Pelletier, an executive counsellor and a board member at the Canadian Psychological Association, says, in a world of unpredictability.

“What is common is the ability that they can influence outcomes,” she says “They are very persistent and they can manage risks. They also have a lot of creativity, because they need to innovate. These can look like ADD-type symptoms because they need to think in a certain direction.”

But those same qualities that adapt so well to business success can bring problems on a personal level. “I thought success, respect, money and accolades would make me happy. I had all of that but still was not,” says Bailey, a former trailer park kid who now speaks of an inner emptiness. He was driven to get help by a fear that his business and professional relationships would implode if he didn’t.

It was a smart decision. Mental illness in all of its guises—addiction, depression, mania and psychosis—is a serious health issue. I point to the streets outside Eastside Games’ West Hastings Street studio, where many victims of mental illness less fortunate than Bailey struggle for daily food and shelter. “What stops you from being like those guys?” I ask him. He fixes me with a baleful stare. “Luck.”

Mental illness is found on the streets and in the boardroom, and Joe Roberts has seen both. In 1989, he was living underneath the Georgia Street Viaduct, addicted to heroin and collecting cans for money. Rescued by his mother, he worked his way up through college, and says he made his first million dollars in sales by the time he was 35. He became president of web design and multimedia firm Mindware Design Communications Ltd., which he sold in 2004. Today Roberts offers consulting and speaking services through a website titled “Skid Row CEO,” and, with partner Sean Richardson, through Pragmatic Thinking Canada Ltd.

“There’s a fine line between batshit-crazy-pushing-a-shopping cart and multi-millionaire. There’s little variance between my life before and now,” Roberts says. Today he flies across Canada speaking about entrepreneurship and inspiration. But the long-clean former addict still finds himself struggling with an inner sense of worthlessness stemming from his childhood. “The world will judge me by my successes, but it isn’t always looking good on the inside,” he says.

Do the stresses of an entrepreneurial lifestyle make mental illness more likely? It’s hard to tell; many successful entrepreneurs will happily talk about their illness as a gift (Bailey describes his as “the magic that is me”). The failed ones that fell victim to their conditions aren’t often willing to come forward and share.

The evidence we have is anecdotal. When I spoke with him, Roberts had just returned from a speaking engagement for Habitat for Humanity, where he told his story, raw and painful, to 300 entrepreneurs. “You’d be surprised at how many people came up to me and said, ‘I suffer from depression and have had addiction issues,’” he says.

What makes it more difficult is that mental health is a continuum, says Pelletier; it isn’t a binary issue. We use many tags to describe different types of mental illness. ADHD is just one. Depression—a feeling of apathy and emptiness—can be situational or chronic. Bipolar disorder can propel people to manic highs and crushing lows.

“All of us have some characteristics that would fit under a certain diagnosis somewhere,” she warns, adding that she gets irritated at news stories suggesting that one in five Canadians will suffer from mental health issues. “That suggests that four of them won’t,” she points out, whereas they’ll all suffer to varying degrees. “It’s not a black and white thing.”

“We’re all psychopaths if we’re any good,” jokes Sean Sherwood. He started his career as a restaurateur in Vancouver in 1999, opening Fiction restaurant in Kitsilano. “There is a sensitivity that I definitely have and that a lot of entrepreneurs have,” he says. “They treat their companies like a personal extension of themselves and take criticism poorly. And they’re frustrated when people can’t see their vision and they feel like they’re surrounded by idiots. And that’s why there’s so much ego involved.”

Sherwood eventually got out of the restaurant business, in part because business partner Matt Walsh took his own life, a week before his wedding. “I’d like to think I learned something from that experience, but I just don’t feel like I did. I don’t think anyone learned anything. Watching someone quit like that shakes your view on existence and the human condition,” Sherwood says.

Suicides among entrepreneurs are not uncommon. November 2012 saw 22-year-old Ilya Zhitomirskiy take his own life. The Russian-born co-founder of Facebook rival Diaspora had inhaled helium and left a suicide note. Young technology entrepreneur Aaron Swartz killed himself on January 12 this year, after being prosecuted by U.S. attorneys over his public use of documents from MIT. The 26-year-old co-founder of Condé Nast-owned social news site Reddit had long suffered from depression, said friends. Less than two weeks later, Jody Sherman, the 47-year-old founder of e-commerce site, died from a self-inflicted gunshot wound, causing people in the tech community to ask bigger questions about suicide among entrepreneurs.

“With the suicides you have to wonder whether they had an extra mental disorder. Healthy people under stress seek help,” says Kathy Marshak, a Vancouver-based therapist with a PhD in psychology.

Bailey says he has never considered such drastic measures, but feels despondent unless there’s a crisis in his life or some kind of drama. For the last few weeks, he has been feeling alternately low and euphoric. “I realized it was partly because I was bored,” he says. “It’s like race car drivers. If you don’t feel like you’re about to crash, you’re not going fast enough.”

Bailey should know. He filled his garage with fast cars after selling his company, SuperRewards, for $50 million to Playerize Inc. last year. Bailey’s company offered a virtual currency for video games (shiny, fast-moving things which Bailey has spent countless hours playing). He paid off his house and piled $1 million into Eastside Games. He should be happy. Is he? “I would not call myself a happy person, no,” he says.


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