Entrepreneurs on the edge

Successful business founders have 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?

Successful entrepreneurs have 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 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 Ecomom.com, 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.

Image: WordShore
Are self-starting entrepreneurs more
predisposed to various types of mental

Many self-starters will understand the symptoms of ADHD. Sufferers are in effect allergic to boredom, says Peter Quily. A former ESL teacher, Quily was diagnosed with ADHD, and in 2003 learned how to coach others with the condition. He has been helping business executives deal with ADHD ever since. “We’re under-stimulated,” he says. “We don’t do well with boredom, and the hyperactivity is a way to self-medicate. We’re trying to get stimulated so that we pay attention.” This boredom causes people to switch between tasks that excite them. It can bind them up in procrastination and time-management issues.

Bailey is, by his own admission, a difficult guy to be around. (Impulsive behaviour is also a common trait among people with ADHD: “I stay stupid shit, I say harmful shit,” says a typically outspoken Bailey.) He originally self-diagnosed eight years ago, taking an ADHD Q&A test himself and scoring high on the scale. But instead of seeking professional help (he’s the smartest guy in the room, right?) he started taking his daughter’s meds instead. “That’s how I roll.”

Eventually he caved and sought help. He was diagnosed by two experts: Paul Swingle, a registered psychologist, and Margaret Weiss, an MD specializing in ADHD.

One of the biggest problems for ADHD sufferers is also their biggest gift: big-picture thinking. “We get overloaded and overwhelmed,” says Quily. ADHD sufferers are so busy looking at the broader picture that it’s difficult to focus on any single task unless they’re entranced by it.

But not all business tasks are inspiring, as Michelle Dean, president of Aloette Cosmetics of Vancouver Fraser South Ltd., knows. Dean bought the Vancouver franchise in 2011, after watching her parents run it for years. Dean, who has more than 60 people working under her, expected to close her business at one stage because her problems got so bad. “Bills were not being paid. It was daunting, overwhelming.” She would forget to ship goods and look after the basic mechanics of the business. “Even writing paycheques was tough.”

Dean couldn’t even cope with basic filing. She would be easily distracted, and dropped one task for another, flitting between them like a hummingbird. This wasn’t a simple case of disorganization; it was a recognized medical condition. She was diagnosed with ADHD in September 2012 and given medication to help with it.

“I took the medication and decided that I had five years of filing to go through,” she recalls. She ploughed through it from start to finish. “It was life-changing.”

As the COO at 1-800-Got-Junk for six years, Cameron Herold helped to take the company from $2 million to $105 million in sales. Now he travels and speaks as a business coach. He repeatedly runs across familiar symptoms in his clients, many of whom exhibit signs of a mild bipolar disorder.

“Bipolar depression has been nicknamed the CEO disease,” Herold says. Entrepreneurs will surf the highs, where they are carried along by passion and enthusiasm, but will then face the downside when they realize that things aren’t as easy as they thought. That can feel like drowning.

Entrepreneurs need the “up” periods in order to be inspiring, to persuade not just themselves but also others to get behind their businesses. “The downs are the counterbalance for the crazy and fast-paced times,” Herold says.

Sufferers of hypomania (known as bipolar 2) will become incredibly intense about an idea, often neither eating nor sleeping when under its spell. Marshak has seen the subsequent bursts of depression lead to suicidal episodes. Then there’s bipolar 1, where the highs reach a full-on mania. “That’s where they’re psychotic. [For example] they really believe that they should hike to China and talk to political figures,” Marshak says.

Marshak recalls treating one entrepreneur and her husband for marital therapy. The woman vanished for days, not even telling her husband where she was. She eventually emailed Marshak, telling her that she wanted to propose a marketing idea. “She had picked up supplies at a pet store and she had been buying art in bars,” said Marshak. The patient came, rambled (when people are in psychosis they can’t function properly, says Marshak), and then left. Her husband finally caught up with her at a restaurant. He told her he was taking her home to get her a change of clothes, but instead drove her straight to the hospital.

“They had to put a police hold on her until they could stabilize her with medication,” Marshak recalls of the bipolar 1 woman. “This is humiliating for a successful person.”

In extreme cases like this one, it can be relatively easy to spot what’s happening, but a lot of the time conditions can be misdiagnosed. Comorbidity—which the British Medical Journal has defined as the co-existence of different mental conditions—makes it harder. Quily pulls one out of the hat that I’d never heard of: oppositional defiant disorder. It comes out as angry, disruptive behavior and he says it often stems from the appearance of ADHD symptoms in children.

“Growing up, you have a problem but no one tells you what it is or how to deal with it. They just judge you,” he says. If it happens often enough, young people will develop a pronounced resistance to authority. “If you channel it properly, you can use someone telling you that you can’t do something as a fuel,” says Quily.

It’s a common trait in successful entrepreneurs, but “the danger is that if you take it too far, you can risk your whole business on it,” Quily warns. This, mixed with the impulsiveness associated with some of these conditions, can be an unhealthy brew.

But then, Bailey likes risk. “I will go all in. I will lose everything I have,” says the entrepreneur. For him, this risk is the sign of a true entrepreneur.

Quily and Herold believe that the symptoms of ADHD, hypomania and other disorders can be harnessed to fuel performance. “It’s not a problem; it’s a trend that we should embrace,” Herold says. “Steve Jobs was a hypomaniac. He was so far out of the box that he couldn’t see the box. Should we have medicated him? No. That’s what made him unique.”

Quily identifies specific assets. The ability to maintain an intense focus, spending hours “in the zone” can be an asset. A rapid-fire mind and the ability to multitask at will while maintaining high energy levels set ADHD sufferers apart from the crowd, he says. They are also superb qualities for entrepreneurship.

“It’s a gift,” says Bailey. “Take that away and maybe I’m not a successful entrepreneur anymore. I don’t look at ADD as being something wrong with me.”

He still takes medication for it, though. Quily argues that good medication can attenuate the negative symptoms of ADHD, while leaving the positive effects intact.

There are also coping mechanisms to help entrepreneurs deal with these symptoms. Delegating tasks they don’t find inspiring can make them more effective, but people running startups often feel as though they must do everything, Quily warns.

Paperwork is like kryptonite to Bailey, who has a financial expert on his team to take that off his plate. He also finds it important to delegate his HR function, because while he’s good at negotiating big deals, he has trouble with one-on-one personal relationships. “I barely understand how my own head works and I have a really hard time understanding other people’s motivations,” he says.

Herold puts systems in place to help save impulsive CEOs from themselves. “They often have these ideas, and the best thing to do is to break down the ideas. But they just often want to start. That can be dangerous,” he says. Using effective teams of senior executives to help mitigate the impulsiveness can be an effective strategy.

Bailey does it himself. He may be prepared to bet the farm on a good business concept, but he has developed his own techniques to review and validate an idea before he pursues it.

Herold urges startup CEOs to use mood swings to their advantage by being counterintuitive. Those at the peak of hypomania may want to make reckless business decisions without thinking them through. “Don’t buy anything or hire people in an up period,” he says. Conversely, depression is a good time to be spending money, because you’re more cautious.

Using these strengths effectively requires the same commitment as dealing with the disadvantages of these psychological symptoms: a willingness to discuss it. Talking about these feelings can be difficult for people who rely on an image of outer strength. Many will still be unwilling to make themselves vulnerable.

Until they do, though, many entrepreneurs find themselves struggling with depression, unable to focus, and feeling overwhelmed, without understanding why. Talking about it is the first step. They may not have full-blown ADHD, bipolar disorder, or any other condition, but they’re undoubtedly extraordinary. If they weren’t, they wouldn’t have taken the risk in the first place.