1. The Age of Innocence

It’s a rare occurrence when you can exhale, relax, and enjoy your good fortune. That was the case at the end of 2000 after our company posted a monster year. Cramer Berkowitz, of which I was president, had already earned a reputation as a shrewd and honest hedge fund, and I had money in the bank as tangible validation of my hard-fought year. I wrote the trading diary for TheStreet.com and had settled into a seamless rhythm of running the trading operation at a $400 million fund while sharing my stream of consciousness in real-time for the world to see.

Yet there were pressures in other areas of my life. My grandfather, Ruby, grew increasingly ill, and he was spending much of his time in intensive care. It was an anxious time for my family as we readied ourselves to say goodbye to our patriarch; it was a dose of reality in an otherwise excellent stretch. Ruby had been a major influence throughout my life. He was more than my guiding light; he was my hero.

My dad left our family when I was two years old, and my grandfather assumed his role. As wonderful as my mother was, devoting herself to raising her children, a young boy needs a man in his life to set the tone and set him straight. As I grew older, I learned that everything happens for a reason. Divorce can be difficult for a child, but it facilitated a bond that might not otherwise exist. Ruby’s presence was empowering, and we became best friends. He taught me how to be a man.

When I graduated college in 1991 and started at Morgan Stanley, I couldn’t afford an apartment in New York City. The confidence that defined my Syracuse University experience had suddenly morphed into an exposed vulnerability as I attempted to learn a craft. I needed a beacon for my moral compass, and, luckily, I didn’t have to look far.

I lived in the den of my grandparents’ home on the upper east side of Manhattan as I found my way. I was overwhelmed with trying to understand the complexities of the financial markets, but I could always count on one thing: Every time I turned around and whenever I needed assurance, Ruby was there with a knowing glance and a steady hand.

Years later, my grandmother, Dorothy, told me that my grandfather sat in my room while I was at work and stared at my shoes. “He loved you so much,” she said with a smile, “he just wanted to be closer to you.”

I was too naive to understand the golden door that opened when I started on Wall Street—or the cost it would exact through the years—but what I lacked in experience was supplanted by my grandfather’s guidance, and I promised myself that I would never let down the single most important person in my life.

Earning stripes on the Morgan Stanley equity derivative desk, as I did after college, wasn’t easy. I knew very little about the business, but thanks to my grandpa, I was well-versed in how to conduct myself as a human being. I had spent countless hours sitting by his side as he espoused wisdom that transcended generations or chosen fields:

“All you have is your name and your word.”

“What goes around comes around.”

“Time is the most precious of commodities.”

“Think positive.”

His phrases struck a chord and lit the way, even if I didn’t fully appreciate the magnitude of their meaning. Each step of my career ushered in a new set of challenges that made my previous plateau pale in comparison, but every time I stumbled, which happened often, Ruby was there to pick me up and point me in the right direction.

When he became ill in 2001 and was admitted to the Delray Medical Center, I traveled to Florida most weekends so I could hold his hand as he struggled. After numerous readers of my column e-mailed to joke about how I was slacking off in the Hamptons, I shared the tale of Ruby. I wrote about why he mattered, where he was, and how very much I loved him.

An amazing thing began to happen. I received e-mails and letters from around the world from people who shared similar stories about grandparents, children, mothers, fathers, and fallen friends. There were ten at first and then a hundred. In time, there were thousands. We read those tributes to Ruby while he lay in intensive care, one after another, month after month.

If so many people took the time to write someone they never met to lift the spirits of a man they had only read about, I pledged that I would continue to share my insights in an attempt to help them navigate the twists and turns of the financial universe. That effort was the genesis of a loyal community that remains to this day, and it was then I realized the power of the Internet, the catharsis of writing, and the importance of giving back.

As I prepared myself for a devastating loss, I settled into my role as a “trader who writes,” and the irony wasn’t lost on me. I was the president of Cramer Berkowitz, and I wrote the trading diary on TheStreet.com, both of which were positions previously held by Jim Cramer. A little more than a year earlier, when he and I had finalized the terms of our partnership, I had no idea why someone would fragment his or her professional focus by writing during the trading day. Yet there I was, producing more than a dozen short-form articles on a daily basis and balancing those seemingly disparate skill-sets.

The relationship between Jim and me was buffered on both sides by business and money. He had invested a large portion of his money in the fund and left it there after he retired, which served as a tacit stamp of approval, while I managed the risk with Jeff Berkowitz and Matt Jacobs and generated page views for TheStreet.com. We had a vested interest in keeping each other happy, and despite a persistent yet unspoken tension, we did just that.

In March 2001, three months after Jim retired from the firm, United Cerebral Palsy honored me for outstanding achievement. I was unsure why I was chosen to receive the award but assumed that they thought my presence would drive attendance. With the help of my friend Steve Nitkin, I secured Run-DMC to perform and then reached out to brokers on the Street to whom we paid commission. Not surprisingly, we sold out the event and raised a lot of money for a worthy cause.

During the ceremony, Cramer stepped on stage and lauded me as the best trader on Wall Street and the best writer at TheStreet.com. I didn’t agree with his assessment, but that was Jim—over the top and all or nothing. I smiled in a knowing and familiar way; while our professional relationship was strained, I genuinely cared for the man and understood why he acted the way he did.

As it turned out, that speech was the apex of our personal relationship.

Saying Goodbye and Opening Up

It was a random Wednesday in the spring of 2001 when I suddenly stopped trading and booked a flight. I knew something was wrong and rather than wait for my scheduled sojourn that Friday, I canceled my appointments and headed south. I arrived at the hospital, raced to my grandfather’s room, held his hand, and whispered in his ear. Five minutes later, a rush of energy passed through my body, limb by limb and goose bump by goose bump, as his body shut down and his grip softened. It was his time, and he passed on his terms, surrounded by his family as he had wished.

A few weeks prior, during one of my visits, he briefly regained consciousness and whispered in my ear, “Take care of the family.” Other than a tender moment with Dorothy, his loving wife of 59 years, when he told her she looked beautiful, those were the last words he would ever speak. He was a boxer in his youth, and I assume he fought until he knew we were ready to let go. I should have been prepared for the pain, but that reality was harsh. Letting go is one thing, but navigating the world without a north star would be entirely more profound.

People deal with loss in different ways. For me, it meant honoring his memory and staying true to the man that he taught me to be. They say the greatest tribute you can pay someone is living your life in a manner consistent with what he or she would have wanted. Soon after his passing, I launched the Ruby Peck Foundation for Children’s Education to channel his energy to future generations.

Denial, anger, sadness, bargaining, and acceptance, as defined by Kübler-Ross, are widely considered to be the five stages of grieving. I had emotionally prepared as best I could, and when he finally passed, I edged into a state of sadness and readied to face the world alone. A video tribute that featured my grandfather was played the night of the UCP benefit, and he said, “I don’t know if I taught him a lot, but I sure hoped he learned a lot.” He did and, by extension, so did I.

My grieving process threaded into my column on TheStreet.com. My editors allowed for some latitude, but it was clear that they wanted nuts and guts financial stuff and would put up with only so much human interest. An underlying tension began to emerge as their editorial staff carved up my columns before they posted. I never claimed to be a good writer, but I spoke from the heart and told the truth. Sometimes, a word here or a shift there can change the entire complexion of the content. I bit my lip as they explained proper grammatical execution to me, and my eyes darted around my eight screens attempting to synthesize hundreds of millions of dollars of risk.

My inbox filled daily with hundreds of e-mails, many of which were about the markets, but a surprising number of which had nothing to do with the tape. It amazed me how diverse my audience was, but, upon reflection, it made complete sense. They weren’t traders who happened to be human beings; they were human beings who happened to be traders.

The Critters Cometh

I used metaphorical representations to represent the stock market—Hoofy the Bull and Boo the Bear—and told both sides of the trading story. There was always a bull case and a bear case, I thought at the time, and the residual grist was what the financial media reported the following morning. It made sense to write through that lens and examine the friction between opinions, which was where I believed true education was found. In time, my readers asked what Hoofy was doing or what Boo was thinking, and they began to assume personalities and perspectives. They resonated—people liked them. It occurred to me that nobody had ever branded the Wall Street bull and bear.

TheStreet.com paid me a salary—$100,000 a year—but it paled in comparison to the money I made running a large fund. For me, writing wasn’t about the compensation as much as it was the catharsis, and we never signed a contract because I didn’t believe TheStreet.com should own the words “Hoofy” or “Boo.” That legal language was industry standard at the time, but it wasn’t my primary industry, nor was it my standard.

They didn’t press the issue; to them, I was a cash cow that produced content, a man in the trenches who generated page views. I wrote incessantly as I navigated the other side of the technology bubble and chronicled my trades for the world to see. If the stock market was a casino, it felt like I had the dice in my hands for an incredibly long time. TheStreet.com was happy, our investors were happy as we notched double-digit gains, and I was happy, albeit a bit hollow. Profitability was a wonderful distraction from the pain of losing my grandfather, but it didn’t fill the void.

Life was good, or so I thought, as I had the toys that society bestows on those with wealth. Forget all the time that elapsed while I sat in front of my screens in an attempt to make money. There would be more dinners with friends, plenty of time to find a bride, and countless hours to relax.

Summer Loving

The loss of my grandfather notwithstanding, life had never been better, at least as measured through a monetary lens. While others struggled with the fire sale on Wall Street, our fund made big money, and I lived the lifestyle to prove it. My buddy Lionel and I ventured to the Hamptons to look for a summer rental in my brand new BMW M5, which I had bought a few weeks prior without so much as looking at the sticker price.

A broker from Sotheby’s had called to tell us of a house in Sag Harbor that had to be seen, and the moment we drove into the compound, we knew it was perfect. “We’ll call it Ruby Ridge,” I said before we got out of the car to explore the grounds.

It was sensational. The Philippe Starck-designed house was stocked with Lichtensteins and featured a meditation tower, a media room, and a wraparound terrace that overlooked Sag Harbor. There were immaculate rolling grounds with an eight-car garage, an adjacent two-bedroom casita, and an outdoor dining pavilion with a working fireplace and kitchen that surrounded a black gunite pool. A croquet field sat between the compound and a 200-foot private beach, all within walking distance of town.

“Seven bedrooms,” one of us said, “there’s a lot of space here.” The broker told us the house was listed at $150,000 for the summer, and it was ours before we got back into my car. We pulled in five or six friends, turned the garage into a nightclub called Shagababy, and smiled amongst ourselves when we eventually overheard others talking about the new, private club somewhere in Sag Harbor.

There were hundreds of people at Ruby Ridge on any given weekend, and we partied like rock stars through the night. It was a summer of debauchery straight out of a movie, a twisted tale of revelry that could have been called “The Top of the Market.” As a trader with my finger on the pulse of trends and turns, I should have seen disaster coming from a mile away.

I left for Hawaii on Labor Day weekend to fulfill a promise I had made to my father, that if he stayed clean, I would return the next year to enjoy quality time with him. He looked good when I saw him; he was off drugs, and his condition was properly medicated. He had volunteered at an animal refuge and proudly walked me through the grounds while I was there.

As we talked about life and the ways of the world, he was eager to hear about my journey, what I was doing on Wall Street, and more importantly, if I was happy. “Sure,” I said as we sat by the pool at the Four Seasons Hotel. “I’m the President of a $400 million dollar hedge fund, I made millions of dollars last year, and I’ve got everything I could ever want absent my own family, which is only a matter of time.”

I suppose we were anxious to impress each other, albeit for different reasons. I yearned for parental acceptance after years of feeling like a substandard son while he, in his own words, wanted to make me proud of how he climbed out of his own abyss. In the end, our motivations didn’t really matter; I had a father again, and the week passed quickly.

The night before I returned to New York, we sat at an outdoor restaurant that overlooked the ocean as a gentle Maui breeze made for a perfect backdrop. I’ll never forget the last thing he said to me before the check came, as I shared my future aspirations. “Relax, son, and enjoy life; you never know when a plane will fall out of the sky and ruin your day.”

The following Tuesday was September 11th, but before I get to that, perhaps I should start at the beginning….