In eighth grade, for every day I spent at school, I spent four at the beach. I didn’t care. I hated school. Given my attendance, or lack thereof, the principal called my mother in for a conference and sat us down. He looked at a sheet of paper recounting my sins. “Ma’am, do you realize how many days of school your son has missed this year?” He chuckled. “It would be easier to tell you the number of days that he actually attended.”
Mom raised an eyebrow at me and asked for the sheet. “May I?” He passed it to her, and her foot started tapping while she read it. Finally, she brushed her hair back and said, “So?”
“What do you mean, ‘So?’” He looked at her like she’d lost her mind. “He’ll repeat the eighth grade.”
Mom dabbed the corners of her lips with a napkin. “Are we done?”
His face turned red. “‘Done?’ Lady, your son is behind. Aren’t you worried about his future?”
Mom stood and grabbed my hand, leading me to the door, which was strange ’cause I was almost as big as she was. Reaching the door, she turned. “Sir, we’re going to go eat a cheeseburger, and then I’m going to buy him a new surfboard because he evidently enjoys that a whole heckuva lot more than whatever you’re doing here.”
I smiled and waved at him.
He was dumbfounded. “And his future?”
She brushed the sun-bleached hair out of my face. “It’ll be waiting on him when he gets there.”
* * *
Mom died my junior year. I was sixteen. Heart disease aided by chain-smoking—a habit she adopted after Dad died. Alone and nauseated at the thought of answering to anyone else, I finished out high school working nights waiting tables, delivering pizza, and doing what I could. That “doing what I could” included selling as much marijuana as I could get my hands on to the surf junkies who were craving pizza. A convenient built-in audience.
Sam, my boss, used his pizza parlor as a front for his drug dealing and he dealt a lot. He brought it in on the shrimp boats out of Mayport and made me an independent contractor. He sold it to me at his cost, and I split all the profit with him. We made a good bit of money. I later learned that he knew the junkies and the amounts they were buying, so he knew exactly how much I was bringing home. When I presented him with exactly that amount, he learned he could trust me. I told him, “I’m not greedy. I just don’t want somebody to kick me out of my house or ship me off to a state-run place.” Every night when I handed him the money, he’d shake his head and mutter, “What is the world coming to? An honest drug runner.” In a world devoid of meaning, I took what identity I could get.
In between deliveries, Sam taught me to play poker and soon discovered I was good at it. It doesn’t take an education in Freud to understand this. I was attracted to risk and not attracted to anything resembling hard work that benefited someone other than me. If you were going to be dumb enough to risk your money in a card game, then I was going to be smart enough to take it from you. The same could have been said for me except that I won far more than I lost so—I argued—I was playing with other people’s money. This would come in handy in the years ahead.
Team sports were contrary to my independence. Signing up for team sports meant that I was willingly joining arms with another group of people and stating that not only could they depend on me, but also that I would depend on them. Statements like “I’ll show up for practice,” “I’ll be at the games,” “I’ll work hard” stood in stark contrast to my how’re-the-waves-looking disposition. That said, I was rather competitive and competition did not scare me. In fact, I rather liked it. Solo feats like wrestling and running. Activities where the outcome resulted from me depending on me. This does not mean that I hunkered down and for the first time in my life learned to apply myself under the whistle-and-clipboard instruction of some guy in shorts pulled up to his armpits. Not at all. I rarely practiced, which drove them nuts, but I hated losing and seldom lost, so my coaches kept me on the team—which was interesting because I didn’t really care whether they did or not.
Same was true for school. Homework seemed like a waste of time. My thinking was, You’ve told me what you want me to know, now give me the test and let me regurgitate it. I could remember most anything I saw or heard and scored well on tests so most of my progress reports read, “Charlie lacks work ethic but possesses great potential.” I can’t tell you how many times I’ve been called “exceedingly bright,” “lacking drive,” or my favorite, “bubbling with potential.”
Whether it was two state wrestling championships, a sub four-minute, thirty-second mile, the death of both my parents before I was seventeen, or the fact that I was three questions shy of acing the SAT and had a guidance counselor who seemed rather keen on my actually attending college, I ended high school with excellent grades, multiple scholarships, and several higher learning options.
My senior English teacher told me I should consider the Marine Corps. I chose Harvard.
My graduating high school class voted me “Most Likely to Be Elected the First President with a Felony Record.” My English teacher was big on knowing where you’re going, what you’re doing, “Have a plan!” Our final senior project was just that. Our plan A followed by plans B and C. I always thought he needed to let his hair down. Loosen his tie. Stop drinking so much prune juice. The paper was supposed to be eight to twelve pages with multiple supporting points. My paper consisted of one very short paragraph: “My plan A is to not have one. Which, by logical deduction, means there can be no possible plans B and C. My future will be there waiting on me when I get there.” I failed that essay and he was incredulous at my choice of college—no, he was downright angry, saying I didn’t deserve such an opportunity. He grew even angrier when he found out I’d be attending for free.
When I walked across the stage and he handed me my diploma, “With Superior Achievement,” he mumbled something under his breath. I shook his hand, smiled widely, and said, “Does that toupee itch as much as it looks like it does?” His eyes darted left and right, and he smoothed his hair with his right hand. “It looks itchy.”
My college decision process was simple. Harvard was expensive and an education there was “worth” a good bit. Again, if they were going to be stupid enough to give it to me, then I was going to be smart enough to take it. And I was smart enough to know that I’d never make it in the Marines with people blowing whistles in my face and screaming at me. Leavenworth did not appeal to me.
Besides, I’d never been to Boston.
* * *
I survived college in the same way I survived high school. I did just enough to get by without getting too caught up in any one thing. I’d always been good with numbers so when I declared a major, something in the world of finance sounded like a good idea.
By the middle of my sophomore year, I had grown tired of the track coach and his incessant need for me to train on his schedule, so following my four-minute, seven-second mile, I told him to take his clipboard and shove it in the same place I told him to put his stopwatch.
While my scholarship at Harvard paid for my tuition, room, and board, my stipend didn’t go very far. Add to that the fact that I had never really enjoyed studying, and it’s not too difficult to understand how many of my nights were taken up with poker.
I was a fair player, but I learned quickly that poker loves no man and good luck can turn to bad with no warning. Further, I detested losing. So I began looking for a way to tilt the odds in my favor. One obvious way was to cheat, which I wasn’t opposed to, but that style of play has a limited shelf life, as does your career once you get caught. Then one night I was invited to a game where I discovered what I soon dubbed the “silver spooners.” Trust fund kids who looked at poker as entertainment. They didn’t really care if they won or lost. They liked the reputation and action either way. Given their reckless behavior, I seized the opportunity and provided a service. By the end of my sophomore year, I had money in the bank and was making a name for myself.