A Practical Way to Get Rich…And Die Trying

Published on October 1, 2020

At 31 years old, self-made serial entrepreneur John Roa sold his UX firm to Salesforce for eight-figures. It should have been a dream come true; instead, the experience nearly killed him. In Roa’s newly released memoir, A Practical Way to Get Rich…And Die Trying (Viking), he shares about the dark side of startup life and reveals for the first time the shocking truth about his entrepreneurial journey.  

Entrepreneurs are 10x more likely to have bipolar disorder, 6x more likely to have ADHD, 3x more likely to abuse drugs, and 2x as likely to be depressed, hospitalized, and suicidal.

Hundreds of thousands in debt at the height of the Recession, Roa, then 26, bootstrapped a design agency which instantly became one of America’s 500 fastest-growing companies. Outwardly, he had it all – youth, money, and power. Behind the scenes, Roa was using every vice imaginable to manage his rampant fear, anxiety, and depression. After suffering a complete psychotic break – for which he was secretly hospitalized – Roa realized that his predisposition to (and untreated) mental health issues together with the “Fake it ‘Till You Make it” ethos of entrepreneurship makes it impossible for founders to project anything other than total perfection.

While Roa’s story may surprise readers, he is not alone. Although rarely discussed, entrepreneurs suffer from higher rates of mental illness than the national average. According to a 2015 study by Dr. Michael Freeman and researchers at the Universities of California, Berkeley and San Francisco, entrepreneurs are 10x more likely to have bipolar disorder, 6x more likely to have ADHD, 3x more likely to abuse drugs, and 2x as likely to be depressed, hospitalized, and suicidal.

A Practical Way to Get Rich…and Die Trying (Viking)

Roa recently shared an exclusive excerpt with us from his book with Grit Daily News. Picking up in the aftermath of his hospitalization, Roa is at a breaking point.  Having come to grips with his languishing mental and physical health, Roa decides to sell ÄKTA.

We all looked haggard.

The ÄKTA executive team— Dean, Kevin, Drew, Matt, Jimmy, and I— sat in our conference room, drinking beers and silently reflecting on what had just taken place. Our faces could all have used some sun and a shave. The only color in the room came from our Christmas sweaters, which we had been mandated to wear for the party taking place throughout the rest of the office. 

It was the middle of December 2014 and we had just finished a  day of meetings with investment banks. We had assembled to determine whether, in the current marketplace, and based on ÄKTA’s growth and success, it would be possible to sell the business to a qualified acquirer for a good chunk of money. 

We had provided each bank with a healthy amount of diligence and financials weeks prior. The  first group was a bunch of well‐ heeled Harvard Business School guys from a global megabank who told us that we were still too young and too small to be meaningfully acquired. To me, an email would have been more convenient than wasting two hours of my time only to have them end with a shitty punch line. But if there is one thing MBAs love, it’s hearing themselves sound smart. 

The second group was a significant industry player that had taken a number of companies like ÄKTA to market, with varying levels of success. Their specialty seemed to be sales to industry holding companies—essentially, huge conglomerates that own dozens or hundreds of independent agencies. These were notoriously bad deals for companies like mine. You were bought for the promise of future money, based on goals and metrics that were intentionally just short of impossible to achieve. Effectively, for the next five or seven years, you’d be working for someone else on your own business— just pushing the finish line farther out. The stories I had heard of companies doing this could have been Hollywood horror scripts. 

Then our messiah arrived. Enter Chuck DelGrande. Chuck represented a boutique bank in Boston, but was essentially a one-man band. He and Dean had some business history, and he came in all smiles. I liked Chuck from that first meeting, and two things about him were immediately clear. This man was irritatingly smart, so naturally intelligent that you felt like a Neanderthal just talking to him. He had a photographic memory and was a human calculator. But he had also channeled that intelligence into becoming a natural killer in business. He had already processed and discarded any new thought or idea you might propose. He was one step ahead of everything. 

Second, he was utterly free of bullshit. The first half of his presentation featured issues he’d identified that might be hurdles in ÄKTA’s sale. His concerns were fully justified. I had built this company from scratch, on a blank canvas, and it went without saying that a lot of things could have been done better. He succinctly and unemotionally walked us through what would have to be cleaned up in order to give us the best chance in the open market. With that acknowledged, he also thought we were perfectly positioned— a perfect size, growth rate, and level of clout— to attract some very interested acquirers. And then he dropped the magic number— the price he thought we could get in the marketplace. It took my breath away. For a split second I allowed myself to imagine that actually happening. Life would change, forever. 

I snapped out of that reverie to hear the weight of his final message. Selling a company like ÄKTA was a terminal process, one way or another. The amount of investment, focus, and strategic changes that we’d have to make would create a situation that would be just about impossible to reverse. If we chose to head down this path, it would lead to a sale, or to the company rapidly failing. 

We contemplated the gravity of the choice we faced during our beer-drinking session, while the rest of the office played Secret Santa and prepared for their holidays off. Was this the right time to try to sell? Were we trying to do so too early, as the MBAssholes had warned? We were only four and a half years old, for Chrissake. Could we survive another year if we didn’t sell?

Chicago is a small town, both in size, when measured against our coastal brethren, and societal fabric. Everyone knows everyone. Business doesn’t stay private for very long. Rumors spread like a disease. So, it wasn’t completely surprising when I started hearing rumors of what had happened with me and Tony.

“Is it true you stole his company and fired him?” 

“I heard you screwed Tony over.” 

Weeks earlier, we had met to try to address his concerns. “I want what’s best for you, Tony,” I said, as we sat in a scuzzy Italian beef deli near the office, where he had laid into a giant beef sandwich, not enjoying any of it. 

I had never seen him so depressed. Months had passed since he had even stepped foot in the office. I rarely talked to him. I had hoped that spending so much time away from the business would have enabled him to clear his head and see he had a very fortuitous position. He held a valuable equity stake in ÄKTA, worth exponentially more than anything he would have created at Fueled, and I had offered to keep him on at his six‐figure salary, without needing to work. 

“I want what’s best for you,” I told him. “Give me some time to sell this bitch, and we will all be rich. I know you feel as if you’ve lost something, but as you can see, everything’s in very good hands, and we have the ability to make something out of it.” 

I meant every word I said, but for whatever reason Tony wasn’t having any of it. He stared at me with such undisguised malice that I realized that no amount of logic was going to break through. He had come to believe that he had been suckered into a bad deal. Pushed out of his company. Left with nothing. Outplayed, outsold. 

I could still put on a gracious smile at dinner and deliver my trade-mark impassioned sales pitch, but the moment the cameras were off, I didn’t have a lot left in me. 

-John Roa, A Practical Way To Get Rich…And Die Trying (Viking)

Some switch deep down inside this man had been flipped. The look in his eyes actually scared me. This was a guy who was willing to handcuff himself to a ship he was sinking, so long as I was also onboard. He would rather end up with nothing than come to a sensible agreement. This was the worst-case scenario. There was no one harder to deal with than someone who felt he had nothing left to lose. There was no reversing our deal, even if I had wanted to. That meant that I would now have to prepare to go to war internally. Our meeting ended, and I knew that that was the last time I’d ever see Tony as a friend. 

The weird thing was, this was the only situation I was currently dealing with at ÄKTA to which I had any emotional attachment. The day-to-day issues involved in running the company that had once kept me up at night now all just felt like cogs in a machine. The executive functions in my brain were so jacked, and the emotional centers so suppressed, that I had become horrifyingly optimized to do my job.

The Tony situation was one of the only problems that would light up my struggling limbic system. He was an actual friend whom I genuinely wanted to do right by. I didn’t care that the rumor mill now had me pegged as an asshole, but I certainly cared he believed that. It was so unfair, and upsetting. I wanted to grab him by his little head and shake this out of him.

 I was in a low place over the Christmas holiday and did very little on New Year’s. My mental episode months earlier had frightened me sufficiently to avoid overindulging or partying much since then. This was overall a good thing, but just meant I had more time to spend in my own head, which remained a complicated and messy place. My depression had worsened, stranding me in a constant fog. The world had the volume turned down and lacked color. My characteristic urge to break things and party had been replaced with no urges at all. I was either at the office or lying in bed at home. The loneliness was suffocating. Did the outside world notice? I didn’t really know. I could still put on a gracious smile at dinner and deliver my trade-mark impassioned sales pitch, but the moment the cameras were off, I didn’t have a lot left in me. 

One particular morning was especially bad. I woke up on the verge of tears, for no obvious reason. I felt a slight tremor in my body, and it hurt my eyes to look out the window. Mental illness is so much more complicated a condition than we give it credit for. Everything becomes up for grabs. Your very existence, your sanity, your self‐ worth. The control your brain has is haunting. Reason, logic, and choice vanish. You can’t identify new thoughts from old. Have I always felt this way? What is normal? Will I ever feel it again? Intrusive thoughts take root in the darkest parts of your brain. It’s the nastiest trick your mind can play. Coupled with the social stigma, it’s inexorable torture. 

I didn’t know then how typical my experiences were in people suffering from depression. I felt as if I were the first and only person to deal with it. In fact, about half of all entrepreneurs have a diagnosable mental health condition.

John Roa, A Practical Way To Get Rich…And Die Trying (Viking)

I didn’t know then how typical my experiences were in people suffering from depression. I felt as if I were the first and only person to deal with it. In fact, about half of all entrepreneurs have a diagnosable mental health condition. Students with severe ADHD are twice as likely to start a business. An entrepreneur is more likely to have a mental issue than the other members of their family. Founders are ten times more likely to suffer from bipolar disorder than the general population, three times more likely to suffer from substance abuse, and are twice as suicidal. 

Entrepreneurs get hit by two powerful forces: biology and society. Our brains are predisposed to be affected by certain mental illnesses, with depression, anxiety, and ADHD being the most common conditions. Society’s contribution comes in the form of the particular culture of entrepreneurship, especially as it has evolved in the millennial generation. Those individuals who go for glory take on remarkable challenges for which no human is really built. As mammals, we are supposed to do nothing but eat, sleep, reproduce, and fight. Making hundreds of decisions a day, managing thousands of people, and being responsible for billions of dollars is not normal, or part of nature’s blueprint. We are pressured to take an extraordinary amount of risk, and push our minds and bodies further than we are really prepared or equipped to. The result is systemic isolation and mental anguish on a brain that is already a bit shaky. The chronic stress prevents the endocrine system, which is responsible for fight or flight responses, from returning to a healthy, relaxed state. Normal, critical bodily functions like sleep and regeneration are deprioritized, because the body believes it’s fighting to survive. For many of us, this becomes an infinite loop of mental chaos, until we can find a way— healthy or unhealthy— to disrupt the cycle, or the dam breaks. 

The saddest part is that there are a number of beneficial ways to deal with these issues, including therapy, wellness treatment, and the responsible use of medication. But at that moment, I didn’t feel that any of these were acceptable solutions for myself. Therapy would have meant admitting to someone all of the fucked‐ up things I had done to reach the point at which I had arrived. That frightened me more than I could articulate. Other forms of treatment would have meant taking my foot off the gas pedal. That wouldn’t fly. I certainly couldn’t verbalize this to my team or partners, fearful as I was that everyone would turn their backs on me, because they would have discovered that rather than working for an impervious genius, their boss was a mere mortal. 

That morning, though, Kevin needed to speak to me, which I imagined wouldn’t involve good news, as there wasn’t a lot of it to go around those days. I used this as my motivation to get out of bed, or else I would have lain there until it grew dark and I could pretend nothing outside was real. 

When I arrived at the office Kevin was waiting in the conference room, with a pile of papers in front of him and a despondent look on his face. This was worse than I thought. He started speaking before I even had a chance to sit down. 

“Do you want the bad news? Or the worse news? Eh, fuck it. We are getting sued. Well, to be more accurate, we are getting sued by two different people, at the same time.” 

Tony. Who was the other?

“Remember those asshole clients from Florida that Fueled brought with them?” he asked. “We fired them shortly after the acquisition and never heard anything else. It looks as if they’re now coming after us for breach of contract.” 

It didn’t take much effort to connect the dots. Tony had called and I explained the situation, and spurred them into taking legal action. 

The American legal system has limitless problems, but one of the most critical for entrepreneurs is the nature of our litigation practices. Anyone can sue anyone else for any claim they want to make, from breach of contract to tagging someone in an unflattering photo— and the receiving party must defend itself. In most situations, frivolous lawsuits are quickly dismissed, but in business, they can be destructive. Even the process of getting something thrown out can cost tens of thousands of dollars in legal fees. And if there is any kind of merit or discovery, going into arbitration, subrogation, or, heaven forbid, an actual trial could easily involve seven figures in fees and years of time. While it’s clearly an abuse of the system, deep-pocketed plaintiffs commonly use this tactic to severely handicap or ruin competitors. 

Not only was Tony prepared to drop a nuke inside a company he was an owner of, but he was willing to spend his own hard-earned money to watch it happen. And he had seemingly persuaded another party to join him in this insane game. 

Even if we were able to get through the sale process with active lawsuits pending, any purchaser would require us to resolve the disputes before the deal closed, making us pay off our accusers in the form of settlements. Tony knew this, too. 

Kevin was short on details regarding Tony’s case, as he had just been alerted to it by our counsel. But it didn’t really matter what he was suing for, or what he hoped to achieve. Whatever his case’s merit, it meant we would have to engage in an expensive, time‐ consuming, and public legal dispute. The gathering of contracts, emails, text messages, testimonies, and interviews, and attending any number of hearings, were about to take over our lives. Tony knew that we had officially started the process to sell the company. Which meant that he also knew that we would be legally obliged to reveal that we had active lawsuits pending against us in that discovery process. Having an equity holder and client suing you, regardless of the reason, is not exactly a good look to a prospective buyer, especially in a client services business. 


John Roa is an entrepreneur, humanitarian, investor, and host of the iHeartRadio podcast The John Roa Show. His no-holds-barred memoir, A Practical Way To Get Rich...And Die Trying about his meteoric rise and fall as a tech startup founder was published by Viking on September 8th.

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