In 2014, John Roa was at a professional high point. His company, Chicago-based ÄKTA, a high-end mobile design and development consultancy, had just been included in the latest Inc. 500 list of fastest-growing private companies in the United States. It put them in the stratosphere of past recipients like Microsoft, Jamba Juice and Oracle.
Roa, the company’s CEO, along with co-founder Kevin Lerash, were flown to Phoenix, Ariz., for the annual Inc. 500 awards ceremony and gala.
But before making it to the big event, Roa, who was just 30 at the time, decided to blow off some steam. As he details in his new memoir, “A Practical Way to Get Rich . . . and Die Trying” (Viking), out Sept. 8, he and Lerash set out for a night of debauchery that involved endless bottles of tequila, a $20,000 tab at a strip club and vague memories of being attacked by an angry man carrying a shotgun.
It wasn’t the first time he and his partner had nearly sabotaged their success with booze, strippers and bad decisions, and it wouldn’t be the last. But it’s only recently that Roa has given serious introspection into why.
ÄKTA, which he’d co-founded in 2011, was attracting major clients like Motorola Solutions and Exelon and its sales had grown by 1,147 percent in just a few years. But the truth, writes Roa, is that he was “scared out of my mind about what I was doing every day. Despite the outward success of the business, I was all too aware of what we were really building: a locomotive with no brakes.”
Roa knew this wasn’t something he could share with the world. “I couldn’t admit in an interview that I was starting to struggle mentally,” he writes, “or that I felt as if, even now, I didn’t know what I was doing. They wanted an unflappable genius. So that’s what I gave them.”
Roa tells The Post that his behavior was at least partly a self-fulfilling prophecy.
“Everything we accomplished was earned and deserved,” he says. “But in my head, it felt fake, it felt fraudulent. I was ready for the whole thing to fail. When the whole thing burned down, and I just figured it was only a matter of time, I could use this as an excuse. It was because of me.”
He’s far from the only successful entrepreneur who’s struggled with self-doubt and self- destructive behavior. Psychiatrist Michael A. Freeman released a groundbreaking study in 2015 which found that 72 percent of entrepreneurs had some form of self-reported mental-health concerns.
They’re twice as likely as the general population to suffer from depression, three times more likely to struggle with substance abuse and ten times more likely to have bipolar disorder.
Roa wondered why.
“Why is the suicide rate among youth in Silicon Valley four times the national average?” Is it just a coincidence, or at the core of what makes a true entrepreneur?
“What separates us from normal people?” he writes. “Are we really as crazy as we seem? Or is it the current culture of entrepreneurship that forces us to do crazy things to succeed?”
I felt as if … I didn’t know what I was doing. They wanted an unflappable genius. So that’s what I gave them.
During the last century, the average American didn’t really aspire to become the next Henry Ford or John D. Rockefeller. Those entrepreneurs seemed like members of a different species. But in today’s start-up culture, it’s easy to think anyone could be the next Jeff Bezos or Elon Musk. It just takes a great idea and a little bit of luck.
According to a 2019 Global Entrepreneurship Monitor report, nearly 16 percent of the US adult population, or roughly 31 million people, identify as entrepreneurs. That’s up from 27 million in 2015.
Roa didn’t have an upbringing that suggested he might have a future in entrepreneurship. The son of lower-middle-class parents in Detroit — his father was a union assembly line worker at Chrysler — he graduated from Grosse Pointe South High with a 2.1 GPA. But by 14, he was running his first business, Onsite Operations, devoted to home-computer repair.
He went from reselling paintball guns to designing Web sites.
“If I could trade it, arbitrage it, service it, refer it or distribute it, I was interested,” Roa writes. “Entrepreneurship is a strong drug, and I was clearly a junkie.”
He wasn’t just a hustler. Roa soon learned that he had a talent for creating a user experience. What interested him was “not design in terms of pretty interfaces and a sleek appliance,” he writes. “But rather, design that got into deep levels of our collective psyche to determine how we wanted to be connected to the world, talk to friends, browse the Web and consume content.”
Even after founding ÄKTA, and as his reputation grew along with his talent, Roa doubted himself.
“I would play the role of the impervious young CEO they all wanted to see,” he says. “I would hide my humanity and struggles. I refused to show any sign of what I perceived as weakness. I wanted people to aspire to be me.”
Imposter syndrome isn’t unique to start-up entrepreneurs. Every industry and profession has it, from surgeons to race-car drivers. “No matter what we’ve done,” Tom Hanks once said, “there comes a point where you think, ‘How did I get here? When are they going to discover that I am, in fact, a fraud and take everything away from me?’”
But entrepreneurs thrive on this, says Roa. “My never-ending battle with impostor syndrome actually led me to make a number of great decisions,” he says. “My fear drove some of the most clever and valuable choices I made. I actually did know exactly what I was doing. I just never allowed myself to believe that.”
He landed some of his biggest clients at ÄKTA despite having no clue what he was offering or if it was possible to deliver. Roa recalls signing TopGold, a global sports entertainment company, and then calling one of his ÄKTA designers and announcing, “I just committed to a load of s–t that admittedly I don’t know anything about. Please for the love of God tell me you know what scalable vector graphics are!”
His job as an entrepreneur, Roa says, was to live up to the hype he created. “After months of telling everyone I was creating the best design agency in Chicago, I started hearing others say that on our behalf,” he writes. “The only person who couldn’t figure out whether to believe the hype was me.”
Freeman, who authored the 2015 study on entrepreneurs and mental health, believes that entrepreneurs have more in common than just sadness and addiction.
“Most people don’t have the propensity for entrepreneurship,” he tells The Post. “While almost everyone can hold a job and many people can lead a group or a team or an organization, very few people can actually start and grow a business.”
Part of the reason is the actual DNA of entrepreneurs.
That propensity for entrepreneurship is 50 percent genetically transmitted, Freeman says. Whether somebody has the potential to create a company from scratch isn’t just about luck or hard work — it’s baked into their DNA.
With that genetic ability comes an “increased vulnerability to a range of mental-health issues that are common among entrepreneurs,” says Freeman. Things like risk tolerance.
“It’s easier for these people to make the leap than it is for others,” he adds.
Roa has found this to be true not just with himself. “I’ve become friends with dozens if not hundreds of other entrepreneurs,” he says. “There is a commonality in how our brains work. And it’s not necessarily a good thing. Because of our biology, we’re all a bit f–ked up and crazy. We’re attracted to risk and excess.”
Some have taken the “crazy” label to an extreme. A 2011 study by psychologist Paul Babiak suggested that one in every 25 CEOs displayed behavior that “technically” qualifies them as psychopaths, four times greater than the general population.
Roa doesn’t agree.
“We aren’t actually crazy,” he says. “One of the defining characteristics of a psychopath is a lack of empathy and emotion. We entrepreneurs are generally the opposite — wildly sensitive and introspective. We need a high level of emotional intelligence to even begin to make it in this game.”
Do entrepreneurs come into their careers with preexisting mental-health issues, or does the vocation itself deserve some of the blame?
Freeman believes that entrepreneurship may exacerbate undiagnosed conditions.
“Over half of them didn’t have any history of mental-health problems before starting their companies,” he says. “Though they may have been more vulnerable than others.”
Extraordinary factors, like abruptly losing customers because of a pandemic, could lead to unforeseen mental challenges. Freeman, who created Econa, a wellness and mental-health program designed for entrepreneurs, is currently working on research on the mental-health impact of COVID-19 on entrepreneurs.
For Roa, the pressures of being the hot, young start-up genius are long behind him. He sold ÄKTA to software company Salesforce in 2015 for a reported $31 million.
“I basically retired,” says Roa, 36. “I’ve been living on an island in Greece for the last four years.”
He admits he’s not sure what he wants readers to take away from his life story. He doesn’t want to discourage up-and-coming entrepreneurs, but he also doesn’t want to over-romanticize that world.
“Entrepreneurs are notoriously full of sh-t,” Roa says. “We are endless self-promoters and salespeople. To succeed, you have to make yourself look fantastic.”
But that isn’t what’s happening in their heads, he says. The self-doubt and anxiety can be crippling and scare away those with ambitions of becoming the next Bill Gates.
“But the crazy ones, the real entrepreneurs, they love that stuff,” Roa says. “The more you tell us how awful it’s going to be, how it’s a big nightmare that breaks down your spirit and every day you feel like you’re going to be exposed as a fraud, the more they want to do it. We love the pain as much as the reward.”
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