John Roa

A Practical Way To Get Rich ... And Die Trying


About the Author
John Roa is an entrepreneur, technologist, humanitarian, and angel investor. He has run multiple technology companies, including design agency ÄKTA, which he sold to Salesforce in 2015. He is a passionate volunteer activist and animal advocate, having been a partner and donor to dozens of nonprofit organizations as well as founding and running his charitable organization, Digital Hope. He hosts The John Roa Show podcast series and is a public speaker on topics ranging from entrepreneurship to mental health. Roa currently lives in Manhattan.



Why Are Business Leaders So Full of Sh*t?

CEOs don’t have it together all the time, despite what their assertive handshakes and confident smiles belie. Author of A Practical Way To Get Rich ... And Die Trying John Roa peels back the mask of LinkedIn professionalism to share the reality of being an entrepreneur, mental health battles and all.

I am conscious of my mental health on a daily basis. Either I recognize when I am feeling good, or when I am feeling depressed, anxious, or suffering some long-standing post-traumatic stress. There isn’t a day that goes by where I am unaware of where I exist on this spectrum.

There have been periods of bliss—feeling no adverse effect for days or weeks at a time. There have also been horrible, dark times that I wouldn’t wish on my worst enemy—like deep levels of depression, or a mental breakdown I suffered while I was the CEO of a fast-growing tech startup.

My awareness of my own mental health has not necessarily correlated with my willingness or ability to talk about it. During the worst periods—normally accelerated by the stress and pressure of being an entrepreneur—I refused to admit I was struggling. I suffered in silence, and avoided any means of support, as they would have required that I face my demons, which I wasn’t ready to do. I didn’t believe anyone would be sympathetic to my issues, and worried I would lose employees and customers when they identified me as a mere vulnerable human, and not a superhero young CEO.

To me, this wasn’t necessarily a conscious decision. I felt there was an unspoken rule in business leadership—something akin to our own version of Don’t Ask, Don’t Tell and toxic masculinity nouveau. We have to look invincible, powerful, and confident. Showing cracks in our armor would only lead to a lack of effectiveness in our roles.

Looking at entrepreneurship specifically, 49% of founders have a diagnosable mental health issue. Depression, substance abuse, and suicide rates, are 2–3x higher than the national average. Yet these are the same leaders we subliminally ask to mask their humanities and struggles in order to meet our criteria of leaders.

After I sold my company and was able to reflect on this culture from afar, I began to understand how big of a problem this is. Leaders, and especially entrepreneurs, are flawed creatures as much as (or likely more than) the average person. We struggle with the stress and pressure of our roles. We often suffer from Imposter Syndrome. We are forced to make hundreds of important decisions a day that could have monumental effects on our own personal lives, as well as potentially thousands of other people.

It has long been understood and somewhat accepted that folks in the arts, music, and athletics are more prone to mental health issues and they’ve been given some level of “permission” to be vulnerable about their humanity. We are somewhat accustomed to stories about musicians struggling with addiction or an artist having a mental breakdown. 

A Practical Way to Get Rich . . . and Die Trying is a memoir of Roa’s entrepreneurship journey.

But when is the last time you heard this about a CEO?

It isn’t because the struggle doesn’t exist. There is a distinct correlation among my peers between success, mental illness, and substance abuse, for instance. It is exceedingly rare to hear this discussed outside of our closely held circles, though. If you dig, you can find endless tragic stories about business leaders losing out to their struggles. But you’ll only hear it as a retrospective.

It makes sense, in a way. Try to imagine what would happen to Tesla’s stock if Elon Musk publicly proclaimed a deep-seated mental disorder or substance abuse issue. The company would tank, as would his ability to ever be a public company CEO.

We expect business leaders to be somewhat “perfect,” at least aesthetically. We revere these superhero leaders, and even grant them celebrity status. We compensate them at superhuman levels. We give them levels of power and control that are literally unimaginable. They supersede laws, governments, limits.

So, on one hand, it makes sense why powerful CEOs feel the need to project this image. But on the other hand, what makes them so different from other types of people we extend similar godly status to, like movie stars, pop stars, and famous artists? 

Kanye West is a billionaire and is the CEO of Kanye West Inc. for all intents and purposes. He went into great detail on Netflix’s My Next Guest Needs No Introduction with David Letterman about his bipolar disorder, proclaiming “When you’re in this state, you’re hyper paranoid about everything. Everyone now is an actor, everything is a conspiracy. You feel the government is putting chips in your head, you feel you are being recorded. You feel everyone wants to kill you. You don’t trust anyone.”

He went on to describe his particular affliction as “a luxury version” and refuses to take medication, as he worries it will stifle his creativity.

Now, going back to my previous point, imagine if Elon had said the same thing.

So, clearly there is a difference in expectations and clearance for vulnerability. But what drives it? What makes business leaders different? And forces them to have to project fake realities?

It is unclear to this author whether these barriers to transparency are a cause or effect of the business culture today. In my personal experience, it felt like an effect. I did not feel when I was in a position of power that I had the “right” to project anything but perfection to the outside world. Anything less than a superhero would make people stop believing in me, quit working for me, or be less interested in hiring my company. So, I subscribed to the narrative, buried my struggles, and projected an image I thought the world demanded of me.

I am not sure what would have happened if I had been more honest. If I had shared some of the lows, and not just the highs, with the world. Or if I had admitted when I was struggling, and even sought support. Would the world have allowed it?

This can only be left as a hypothetical, because I never broke character, so I cannot know what would have been different. And this is the case for almost all business leaders. We really don’t know what the result would be, because we all refuse to break the unspoken guidelines, which in turn creates an infinite loop. If this was a harmless loop, it would be somewhat of a nonissue. But this culture is anything but harmless.

Looking at entrepreneurship specifically, 49% of founders have a diagnosable mental health issue. Depression, substance abuse, and suicide rates are 2–3x higher than the national average. Yet these are the same leaders we subliminally ask to mask their humanities and struggles in order to meet our criteria of leaders.

So, this answers the “why”—why we are so full of sh*t, why we struggle so much, why there are so many tragic stories of leaders losing the fight. But the broader dilemma persists—what do we do about it?

How do we change the culture that forces us to be imposters? How do we begin to give business leaders the same “permission” to be human beings that we extend to other disciplines? How do we break the cycle?