Confessions of a Crypto Millionaire

by Dan Conway

  The first person to speak at our table was an older lady who knew it was best to get it over with.

  “I like to garden when I come home from work.” Yes! That is the right approach, we all agreed.I said I liked to take the kids to the park. And so on.

  Then we were provided with devices and asked to fill out a long questionnaire that was intended to anonymously measure our contentment level. The algorithm would then identify specific areas for improvement, starting with the low-hanging fruit. It would encourage us by highlighting aspects of our lives that were particularly healthy. The questions were like these: When faced with a professional challenge, do you think it is very likely you will persevere, somewhat likely, or not at all likely? And In times of crisis, are you the type of person who quickly jumps in to help or someone who is most likely to need help?

  We all worked quietly for ten minutes. The hell with it, I thought. I answered honestly.

  Then the music started, and our leader told us it was time for us to share our results with each other if we so desired. Each person at my table chose to do so, reading the various machine-driven punch lines spit out by the emotional intelligence algorithm. They all sounded something like this: You’re doing great! Consider eating more leafy greens and other fibrous foods and adding one more thirty-minute cardio session on weekends, or Sleep needs to be your priority! Your exercise and nutrition are great, now focus on getting one more hour of zzzs each night :) You deserve the rest! Mine was along the lines of, Something is seriously wrong with you. You need to see a mental health professional as soon as possible.

  I chose not to share that. Even the Machines recognized my deteriorating condition. It felt like I had a deep, dark secret to hide, which I did. I was a pathetic loser. But I couldn’t imagine giving up the pills and booze. That would be like living without air, love, or joy. Something had to give.

  ***

  My poor sister died on a Tuesday in the Intensive Care Unit at the UCSF Medical Center. That morning, twenty of us gathered in the waiting room. In groups of four, we cycled in to be with her one last time before she left us forever. I wrote the obituary and included this line: Maureen never saved for retirement—good job, Maur.

  She wouldn’t need the money, and she hadn’t spent time stockpiling it. She had always opted for life experience over financial security. Maureen had abandoned a successful career in the title business to follow her lifelong dream to start a restaurant, despite having no restaurant experience. If you know anything about the title business, you know it is stable, well paid, and boring. So after years of head-down paper pushing, she said, “Fuck it,” and with her partner opened Towles Cafe, a seafood restaurant in downtown Burlingame.

  She did what we’d all do if the perfect version of ourselves owned a restaurant. She brought in promising chefs from the city and blues singers from Oakland to perform on Friday and Saturday nights. She hung out with her customers, making friends and sharing laughs and little intimacies. Good customers were often surprised with a comped meal. The ten o’clock no-loud-music ordinance was completely ignored. Her famous cheesy garlic bread was lauded all over town.

  A couple of local magicians performed during the weekdays until they became pests. When they were snotty about not getting paid on time, Maureen told them to beat it and locked the front door to applause from her regulars. Life was happening at Towles, and I don’t think she regretted any of it as she lay on her deathbed with a small bank account.

  At the reception following my sister’s funeral, I had four Manhattans and six Vicodins. I also smoked a joint with a friend and downed an Adderall to keep me chugging along. It was a hell of a party, and it went all day. I don’t remember it as a sad event. I was flying high, introducing my friends to distant family members, recalling stories about Maureen and generally having a good time. That was the general vibe of her funeral. That’s what you get when you celebrate a loved one’s life in an Irish family. It was Finnegan’s Wake minus the resurrection, unfortunately.

  On the same night as the funeral, Eileen and I had prepaid to attend an 80s costume party at a friend’s house. It was a fundraiser for our kids’ elementary school. Obviously I wouldn’t be in any mood to attend, but we agreed that Eileen should drop by. The whole school crew would be there in their edgiest costumes, ready to get seriously fucked up in support of our children’s education.

  When I got home to an empty house after the funeral—the kids were staying at a friend’s—I changed my mind and decided to walk over to the party. I put on my Richard Simmons short shorts and made a beeline for the fun.

  Eileen was surprised to see me there. Most people were buzzing pretty hard, but not like me. I poured myself a glass of vodka from the self-service bar and started roaming around. I found a karaoke room—here is where it gets fuzzy—and decided to join a group of moms who were in the middle of a song, really letting loose. It was tight quarters, and I started knocking them around. I kept on singing. Then I remember a big disturbance, and a crowd of people gathered around me. I had fallen over a coffee table and broken two fingers. The physical pain must’ve opened some doors to other types of anguish. I started crying about Maureen, wailing, actually, in the middle of the party. The entire school community watched in suspense. It’s hard to imagine a bigger scene.

  Some good friends of ours helped Eileen drag me out of there. I could only take a few steps before crashing down on the sidewalk or into the bushes. My arms and legs were bloody. When we got home, Eileen told me to go to bed, but apparently I wanted a nightcap. I poured myself a tumbler full of wine and started upstairs. I fell down, shattering the glass all over the stairs. I kept on going, and when I reached our room decided I needed to go to the bathroom, so I made my way to our dresser.

  Eileen had always been borderline OCD, and she’d been more so lately. She liked to keep things neat and tidy. If I used a rag to wipe up kid’s pee off the floor, she’d want me to throw it away rather than put it in the washing machine. So you can imagine the suspense when I opened her undergarments drawer and unbuttoned my pants. She screamed at me to stop, but I was beyond human intervention. I let it rip, draining a quart of urine onto her socks and panties.

  There was a heavy crystal lamp on our nightstand that we received as a wedding gift. As I leaned my head back, eyes half-shut, swaying idiotically, Eileen says she had a strong urge to grab that lamp and brain me. She had the perfect angle, since my back was turned and I was perfectly defenseless. It would have been quite humane. In this Law and Order episode, other partygoers would attest that I was extremely drunk that night and had been disturbed for quite some time. He must have attacked her, they’d agree. I definitely would’ve voted to acquit.

  I would need to quit drinking, or Eileen and the kids were out of there—or, more precisely, I was out of there. The sock drawer incident was the final straw. Eileen now had a mental image burned into her brain that she’d never forget. She only knew about the drinking, not the pills. In my depleted state, I couldn’t hold onto that secret any longer. It was eating me alive.

  A few nights later, as we lay in bed, I said, “Eileen, I have a secret I need to share.” I knew she would assume that I was having an affair. That’s the only big secret spouses keep, unless one of them is Walter White. “I’m addicted to Vicodin.”

  There was relief on her face, more relief than anger, due to my approach (what a bastard). She then got scared. This appeared to be a scene from a shitty Lifetime movie. The one about the husband who washes out of the marriage and only occasionally drops by at midnight, high on angel dust, to see the kids. She jumped into action and said I needed to go to rehab. I agreed.

  Without drugs and alcohol, I was faced with having to relearn how to feel normal. My brain had to reestablish its natural biochemistry. Alcohol and opioids had occupied the pleasure centers for so long that their removal created an instant emotional crisis, not to mention a lot of gastrointestinal problems. I would soldier on because that was the right thing t
o do for my family, but I couldn’t help ask my rehab counselor, “Do people in my situation ever feel happy again?” I was skeptical.

  I attended an outpatient rehab every weekday from six to eight p.m for three months. At the outset, I worried rehab was going to be a series of painfully awkward role-playing sessions like the type I was forced to endure at Acme corporate seminars. Instead, it was a thoroughly and almost wholly enjoyable experience. Listening to Joe, the twenty-four-year-old barista talk about how he was trying to calm his inner critic with heroin, or Linda, a seventy-one-year-old upper-crust lady discuss how she drank a bottle of wine before meeting her friends at the farmer’s market on Saturday mornings, made me realize that I was among my people.

  They all had their own Flip Sides who’d gone rogue, shamed them, ruined their lives. We were banding together, gaining strength to change by hearing about the difficult rebuilds happening in each other’s lives. It was so much easier to recognize the mania, the attempts to escape, the foolish and impulsive actions of our fellow addicts and alcoholics, than it was our own. Amid our car crashes, broken marriages, lost fortunes, ruined health, arrests, and other shameful behavior, we all had the same destructive urge to change the way we felt.

  Chapter Eleven

  Refurbished

  Rebounds are lovely things, and that is what I did after sobering up. Changes were made on the Red State team, and I landed a new set of masters who didn’t have the same incentives to destroy California. In addition, a number of malcontent legacy members on my own team retired or left the company. Perhaps they left because they hated me. If so, the feeling was mutual, though I was trying to be more spiritual.

  I could now bring in my own people, who would be loyal to me and had the right temperaments and skills. Despite my abysmal start at the company, I was trying to convince myself that I could master this corporate system, after all. Maybe the drugs and alcohol had been the cause of my problems.

  On the lifestyle front, I was now a member of a twelve-step program, and it gave me the tools to be more emotionally intelligent, when I chose to use them. The advice I received usually involved me turning the other cheek or looking at my own part in whatever work problems I was having. The more I did this, resisting the urge for resentments or illusions of grandeur, the more I could handle the bumps and bruises of corporate life, especially since I had a clean slate, of sorts.

  After a year of recovery, I was no longer craving alcohol or drugs. Eileen was happy with my progress. I was grateful for her patience. With the help of Marcie, our recently added marriage counselor, we could both be honest. Eileen let me know how much I had let her down and how terrified she’d been. We were both able to discuss previously off-limit topics relating to our families and also minor grievances, like how she held it over me that I didn’t know how to fix the printer. By the end of a year of counseling, we were star pupils, patting ourselves on the back for being able to get through serious problems.

  When my body felt better, I joined a gym and started exercising during lunch. I spilled my guts and told my trainer that I had just gotten off pills. He upped the pain quotient of our workouts. I didn’t know if this was punishment or a scientific approach to replenishing my dopamine, but it hurt. He was big into ropes and had me try to make waves with these heavy navy-style cords until my arms fell off. Then he’d strap ropes connecting his waist to mine, and I’d pull him all over the gym. It was painful and weird, but I’d do whatever it took.

  I was starting to feel outstanding, like a new man, and it showed in my work product.

  I had a perfect opportunity to show off my new persona when the entire national public relations team converged on New York for a national planning retreat. From the start of the first meeting, I was on point, cracking a joke here, making a brief comment there. I suddenly seemed to find my footing. I was ready to show them off in the final presentation from our big boss, the CEO direct report who had worked in Congressional leadership and was a big player on the Hill. When he was done with his remarks, he saved half of his time for questions. Everyone knew you needed to be careful with questions. But I was in the zone.

  I raised my hand. “We have an issue with a preemption tax in four California cities…” Suddenly, Flip Side appeared around a corner. He jumped in and grabbed my brain. He started squeezing with all his might. “So that’s an issue… There are others, but they are California specific...” I sputtered and lost my train of thought while trying to hold eye contact and verbal tone.

  People who had only been half paying attention now turned to look. A question that should have been rattled off in five seconds had stalled in mid-air. “I think that what we are facing is a confluence of factors in the public life or in the government, I mean the public political environment in California.” What in the actual fuck was I talking about? Something amazing was happening, everyone realized. “So that’s where the issue is now in my mind, and I’m not sure, you may need to know this in New York, and I’d like to think there are some other issues like this, before, that we’ve faced as a company, I mean, at least in California.” My face reddened, and I stumbled to a close, holding my expression as best I could.

  The big shot looked confused and annoyed. “I guess we will have to look at that, Dan… Anyone else?”

  His answer was shorter than my question, which made me look like a jackass. Which I was.

  It was a high-stakes blunder on a big stage—a shocking, unforced error at a time when I was trying to forge a new reputation. This man, who didn’t know me well, would need to approve and advocate for ANY promotions in the department. Now he likely thought I was an idiot and a wannabe show-off.

  When I returned to California, Prince Charming winked and told me, “I heard about your question.”

  That was when my subconscious started to tell me, once and for all, that I wouldn’t be able to make it in corporate America to the degree I needed. Because as 2014 rolled into 2015, I began searching for other ways to make my mark. I wasn’t just looking for career stability, I was looking for something significant.

  Me searching for something in itself was a potential problem. Why did I need to be always striving for something greater, something BIG? Being a decent man, husband, and father should have been enough. But I craved a big hit. I wasn’t willing to give up dreams of an extraordinary life. That was the American Way, as I saw it. But I had to be careful to modulate it and not go off the deep end.

  My mind kept circling back to financial independence, a way to get free and clear of corporate America. I didn’t have any path to make that happen. Despite that indisputable fact, in my spare time I began listening to financial podcasts and started reading any blogs I could find on early retirement. In particular, the Reddit Financial Independence subreddit was inspiring. It was filled with people who had made enough money to live without income, as long as they budgeted and invested wisely.

  Over the years, living in Silicon Valley, I’d spent a lot of time tabulating how much money friends and acquaintances had made on various “exits” like IPOs and acquisitions. Even if they didn’t mention the size of their windfall, and most didn’t, their houses and Teslas gave them away, as did their vacations to Croatia and Thailand. I always wanted to know the details about their finances.

  I remember specifically asking my friend Larry about it on the soccer sidelines. I dug around with open-ended questions like, “Are you able to take some time off?” I couldn’t ask exactly how much money he made, so I tried sounding big picture-y instead. “Do you now have the opportunity to work on your own projects?” I felt dirty, but I couldn’t help it. I wanted to know.

  Of course, he volleyed back the big-pictur-ey vibe. He said, “I’ve enjoyed startups, and so that’s what I’ll continue doing.”

  I’d always been a contributor to my 401(k), as had Eileen. We rolled them over from job to job, consolidating as we went. At the same time that I was building my career, I kept one eye on that little, yet growing, nest egg. I’d s
earch the web and read every article I could about people who’d actually built up enough money to retire at fifty-nine or sixty simply by contributing a reasonable amount on a monthly basis.

  The miracle of compound interest is a wonderful thing. The miracle is that you earn interest on your contributions, and then you earn interest on the interest. If we kept feeding our savings, we’d eventually have a lot of money. But to get there, we’d have to commit to steady contributions for many more years.

  Even if I’d somehow been able to get the big money at Acme by making it to Fifth Level and then officer, I knew that if I had enough money, I’d leave the company and pursue my own passions, as vaguely defined as they were. I guess I was outside of the zeitgeist of poetic tweets from Silicon Valley billionaires, who insisted it wasn’t about the money, it was about the joy of building teams and “making things,” their favorite humblebrag.

  For most real people I knew in corporate America, some of whom worked at those billionaires’ companies, it was about making enough money to get out. The people in the growing financial independence subreddits had an exact dollar amount in mind.

  Writing entered my mind as something I was good at, could do in my spare time and might lead to something lucrative eventually. Flip Side couldn’t foul me up with anxiety attacks when I was writing, like he could when I was talking.

  I discovered Medium, a new blogging platform where unknown writers could be noticed for the quality of their work. In the past, I never had the discipline to follow through with personal writing projects. But now with Medium, I found an audience. That turned out to be the missing incentive.

  I began with a shy piece about the leadership lessons I learned running a foot race near my house. A few people read it. Then I wrote about the time my mother vetoed my father’s expensive dental treatment when he was terminally ill. That generated a good deal of interest.