Chapter 1: The Smartest, Stupid Thing I Ever Did

Life has a funny way of pushing you in a direction that you would have never imagined possible. It only takes one fateful decision or one extraordinary person to determine your destiny. In my case, it was both.

It all started because I was such a social schmuck in high school. I was taking all the advanced business courses and was a bit of a nerd. I loved my spreadsheets and how the math never lied when I ran dummy business scenarios to see if I made or lost money. If I was making a profit, there was always the question of where I should invest in improving the business. Research? Distribution? Expansion? Customer service? Advertising? If I was losing money, I needed to understand why the competition kicked my butt and adjust. I thought it was great fun.

I started a yard maintenance business when I entered high school. I lived in the suburbs outside of Hartford, Connecticut. The neighborhood is a mix of ranch and cape-style houses crowded together with small yards and short driveways. I quickly picked up business because I was reliable, fairly priced, and did the job the way the customers wanted it done. I was knocking off the sloppy competition left and right and quickly outgrew my one-man show.

Ted and Carl Sullivan, two brothers with their own yard care business, also did a good job and kept their customers happy. I approached them and told them I could line up at least three houses or more for each of them if they would be willing to give me ten percent of the take, and I would do the bookkeeping, billing, collection, and take care of any problems they had with customers. They were a little skeptical at first but agreed to give me ten percent of new business. A month later, they gave me ten percent of all their business for my services.

Ted and Carl became my best and only friends throughout my last three years in high school. We worked hard in the summer and winter and made a tidy sum for high school kids.

So how did I end up headed for an extremely interesting and financially rewarding life? It sure as hell wasn’t from mowing lawns and shoveling snow.

It was getting close to graduation, and the senior prom was in two weeks. Being the social schmuck that I was, I sent e-mails to three girls I thought might agree to be my date. I received two “in your dreams” and a “don’t ever e-mail me again” in response.

I was determined not to miss my senior prom, and I was going to have a date. Carl and Ted already had dates lined up, and I was not going to be made fun of by my two best friends for the rest of my life.

I went into my businessman mode and thought, what do you do when you don’t have the human resources you need? The simple answer is you hire or contract for them. I checked my bank balance, and it showed $5,386.27. A date for the prom was a short-term need, so contracting it is. I am sure you have figured out where this is going by now. And you’re right. That night I jumped in the seven-year-old Chevy Impala and headed for downtown Hartford and started cruising.

I came to an area that looked promising. There were lots of folks walking around, a couple of porn shops, a XXX theater, and women standing around smoking and smiling at the guys as they walked by. As I was driving slowly down the street checking them out, I started to think this wasn’t such a good idea.

Most of them looked too old or too overweight to be my prom date. A couple of the girls were downright ugly and looked high. I was starting to rethink my options and thought maybe I should ask my cousin Ellie. She would laugh and tell everyone in the family, but maybe she wouldn’t tell Ted and Carl she was my cousin if I begged her on my knees.

I was about to take a right at the next corner and head out of the city when I spotted a girl that didn’t quite fit in with the rest. She was younger-looking, blond, and thin. She was wearing short shorts and a T-shirt that stopped short of her navel. I turned the corner and parked the car, and walked back to where I had spotted her. She was leaning in the window of a late model Corvette talking to a guy with tattoos up and down his arms and neck. She reached into her pocket and handed him some cash. Then I heard him say, “Get the hell back out there bitch. It looks like you got a customer coming.”

She turned around as he drove away and saw me standing there with my hands in my pockets. She smiled at me and asked, “Something I can do for you, sweetie?”

I started with my best pick-up line, “I’m not sure, maybe.”

I was taken aback as she candidly listed her services, “When you figure it out, let me know. A hand-job is $50, a blowjob is $75, and if you want to fuck me, it’s $150. You will use a condom.”

I felt very awkward but determined, “Can I just talk to you?”

She sounded a little disappointed as she informed me of the price, “Oh, one of those. That’s $50 a half-hour, and I will tell you my whole life story.”

Not being familiar with the rules, I asked if I should pay now or after we were done.

She looked me over for a second before answering, “You look honest enough. How about if you give me half now and half when I have told you my life story.”

I took out my wallet to get out two tens and a five and handed them to her.

Now that I had given her some money, she sounded a little friendlier, “So what’s your name?”

I wasn’t ready to give her my full name yet, “It’s John.”

She laughed and said, “That’s perfect.”

I still had my wallet out, and I put my license right up to her face and said, “My name really is John.”

She backed up a step. “Yes, I see it really is John, John Paterson as a matter-of-fact. Nice to meet you, John. I’m Jenny.”

So much for not telling her my last name, “It’s nice to meet you too, Jenny. Would you mind if we talked in the diner across the street and we could get something to eat? I will pay.”

That seemed to bring a genuine smile to her face as she quickly agreed, “I’m starting to like you already. I would love to sit down for a half-hour and get something to eat.”

As we started across the street, she linked her arm to mine, so we looked like a couple when we entered the dinner. We took a booth near the middle next to a window. A large black woman in her late forties or early fifties with ‘Trudy’ on her nametag greeted Jenny, “Hi Jenny,” then gave me a dirty look and took our order. I ordered the club sandwich and tea for Jenny and hot pastrami and coffee for myself.

Jenny did not waste any time getting to her life story. “Well, here goes. I grew up in upstate New York and came down here about a year and a half ago, and...”

I held my hand up and interrupted her, “Please stop. I am not here to hear your life story. I’m here to ask you a few questions, and I have a business proposition for you. Don’t worry; I will give you the other twenty-five even if you turn me down.”

Jenny sat back and crossed her arms in a carefully guarded manner, “Okay, but you’re not one of those young-looking vice cops, are you? That guy you saw me talking to gets pissed when I get picked up, and he has to bail me out.”

“No, I’m not a cop,” I assured her. “I’m still in high school.”

She let me know that didn’t sit too well with her either, “Shit, that’s even worse, you’re underage.”