Breaking the Rules: A Billionaire Romance

by Sarah J. Brooks

  Ms. Wendy, Merrick’s assistant, had insisted on having every Sunday off. Merrick tried to deny her, but she was a tough lady and didn’t give in. The result was Merrick never getting to any of his Sunday plans unless he was called and reminded. But if his phone was off, and he was asleep, even calling him wouldn’t be enough because the call would go straight to voicemail.

  “Hey now, he’s a busy guy,” Ren, the youngest of our group said in defense of Merrick.

  “Yeah, like I’m not busy,” Dean chimed in. “I’m doing eight shows a week, television interviews, reading new movie scripts. I’m busy every single day.”

  We all knew Dean was exaggerating, but none of us wanted to be the ones to burst his bubble. Dean was certainly busy with his Broadway show, but there weren’t likely many movie studios looking to cast him in their films. Dean had joined the investment club so he could learn to manage his own money, in the hopes that he would get some big leading roles and then wouldn’t have to rely on crooked money managers to dwindle away all his money.

  “Well, I was out with him last night, and we both went home early. I have a good feeling that he’s going to show up. Let’s just move on for right now.”

  “Or move on for the whole meeting,” Luke added as he snickered under his breath.

  Luke worked with me at the firm and was the only guy from work that I actually invited to join our group. We invested large amounts of money, and I suspected he was a little out of his league with us, but he was a stand up guy, and I trusted him. Luke had come to New York from the Midwest and was a good friend to me, especially now that I wasn’t his boss.

  We had worked together on the floor for a few months as I was just getting moved up to management, and he was just getting started in the business. He was a few years younger than me but definitely mature for his age. He wanted to build his guy friends up when he moved out here, and the investment club was the perfect opportunity.

  It was harder than one might think to find friends in New York City. Almost as hard as it was to find a decent date. Our little investment club afforded us the opportunity to make friends with similar investment-minded people. It wasn’t like you could show up at a bar, and as a guy, if he wanted to hang out, that would certainly be taken the wrong way.

  “On a scale of one to ten, how hot was the girl he brought home last night?” Ren asked.

  Ren, whose real name was Brandon Carter, had recently sold a dating app that he made while in college. He was in his early twenties and had already made millions of dollars. He was more than ten years younger than me, and I felt the jealousy rearing its head when I was around him. He was a fresh-faced technology wiz kid without a clue of what to do with his millions of dollars. It was the kind of problem I would have loved to of had when I was his age.

  I had worked my fingers to the bone over the last fifteen years at Stanley and Associates. No one was handing me millions of dollars. No one was offering me an early retirement from the confines of the regular work world. Nope, I had to get what I wanted with old-fashioned work.

  A lot of people I worked with thought that Merrick and I were friends so I must have been handed my status and money like he was, but it wasn’t even remotely true. I worked my ass off to pay for college and then twice as hard to learn the investing business. Yes, I was lucky that I could get hired on at Stanley and Associates, but they would never have kept me if I wasn’t good at my job.

  The truth was that I was excellent at my job. I knew how to predict the ups and downs of the market through research and totally understanding the companies I was working with. I now managed one of the most successful investment portfolios in all of Stanley and Associates. It wasn’t luck that got me to where I was; it was skill, but I knew people around me constantly believed luck had played a strong roll in my current life.

  Part of the reason I started the investment club was to help other young men learn the power of managing their own money, but part of it was also to fill my own need of proving that I knew what I was doing. I loved the guys and their friendship, but I hated when they mocked the lifestyle I had. Making small jabs at Merrick always seemed like a little jab at me, and it took self-control to understand they weren’t coming at me from a bad place. These were my friends, and they just said things; none of it was personal.

  “She was very pretty,” I added.

  “One to ten man, what was her score?” Ren pushed me to give him details.

  I doubted that Ren got out much with the ladies. He had probably been a hit with the college girls, but the women of Manhattan were known for chewing a man up and spitting him out when they were done with him.

  Ren was a delicate young looking man with dark tanned skin and a thin frame. He was funny and smart, but certainly not built like the kind of guy who would sweep a woman off her feet. His biggest asset was his humor, though. It had probably landed him a few ladies while he was in New York.

  The women of New York were tough. If they lived on their own, it was likely they had pretty successful jobs. If they lived with roommates, they were probably trying to follow some sort of dream while in New York. Women didn’t have time for men who didn’t help them in some way.

  I don’t necessarily mean helping them financially. Even a quick fuck was helping them relieve stress. From what I had figured out about the women of New York, they didn’t like to waste their time. If you didn’t serve a purpose to them, they didn’t have a purpose for you. Unfortunately, Ren hadn’t quite figured that out about women yet.

  “Nine, but only because her name was Bambi, and I deduct a point for weird names.”

  “He isn’t coming; I guarantee it,” Ren added. “The probability is non-existent if he went home with a hot girl named Bambi.”

  We all laughed. It was true, and as much as I didn’t want to believe it, Merrick wasn’t going to make it to our little investment club meeting. Bambi was a beautiful woman, and I suspected Merrick was curled up next to her and not willing to let her go just yet. Although he loved the one-night stand as much as I did, Merrick did have a soft spot for all women, and I could tell he was considering settling down someday.

  “Who did you get if Merrick had the hot girl named Bambi?” Luke said.

  Ren and Dean laughed at the idea of me getting stuck with an ugly girl. They knew better, though. Not only did I find beauty in almost every woman, but I also wasn’t the type of guy who would put a woman’s appearance down for any reason.

  Women were too concerned about their looks anyways, and I hated it. I wished I could just meet a girl who was out with her friends and actually didn’t care what others thought of her. Girls that went out all dolled up and trolling for guys were so easy to spot. But what I loved most was finding a woman among her friends and totally having a blast and unaware how damn beautiful she was.

  The guys assumed that I always got the second choice when Merrick and I were picking up women. But I could have picked Bambi; maybe I should have picked her. The truth was that Merrick and I were equals on the dating playing field and pretty much anytime we left the office. We had known each other for long enough that we appreciated each other without worrying about the office politics that happened during the workday.

  “Equally hot brunette; she was a total freak in the bedroom.”

  I wasn’t about to tell them just how freaky she was or how badly I wanted out of that apartment when I finally had the chance. They didn’t need to know all of that. I should have picked Bambi, I thought to myself. Merrick had probably enjoyed a much better night than I had. Although, even the torturous game that Stephanie played with me was still better than returning home to my empty bed alone.

  “Damn, Wyatt, you need to take me out with you guys sometime,” Ren added.

  “Yeah, because bringing a toddler with me to the clubs will help me find a girlfriend.” I laughed.

  “Clubs aren’t really the best place to find decent ladies if you want a girlfriend. You know that, right?”

  “Yeah,
I know, but I’m certainly not going to meet the woman of my dreams in the middle of an investment firm. I’ve got to try something.”

  “What about my app?” Ren asked with a cheesy grin.

  “Oh, yeah, that’s just what I need; a bunch of crazy online women chasing me down. No, thank you. I want to at least know what I’m getting when I meet a woman. Online dating is scary as hell.”

  As the words left my mouth, I remembered the fear I felt as Stephanie tied up both of my arms. It wasn’t a genuine fear of my life or anything like that, but I certainly felt out of control, and I didn’t like that at all. My life was about controlled decision, and perhaps Ren’s dating app would be an option in my future.

  “Dude you should seriously check out the Date Tonight app. It’s not like any other dating app on the market. You’ll find a match based on the questionnaires, but then you only meet up in a natural setting that the app helps to organize. It’s very popular right now.”

  “Not really my cup of tea, but I’ll think about it. Can I pick a blonde named Bambi?” I joked. “Now let’s get back to this week’s investments. We need to make some decisions so we can move forward.”

  “I’m dating online,” Dean added after our conversation had finished and everyone pulled out their notebooks to begin talking about investments.

  “What? Really?”

  I was shocked. Dean Morrison was the last guy I would have suspected would need to turn to a dating app. He probably had dozens of girls throwing themselves at him every night after his show. Most of the general public didn’t understand the nature of his financial devastation. They just thought of him as a hunky leading man who had taken to Broadway in an eccentric spur of the moment decision.

  “Yeah, you can pick and choose what’s important to you. I mean, I haven’t found a match yet, but I’m still hopeful.”

  “Are you using Date Tonight?” Ren asked.

  “Naw, I’m on the mainstream sites, though. The problem I’m running into is that all the normal girls are busy working and not going out partying or even bothering to date. It’s hard to meet a sweet girl that wants to settle down.”

  “This whole conversation sounds like a group of old men talking to each other. Come on guys; you’re not that old,” Ren laughed.

  He was right. We did sound like old men as we talked about finding a decent woman and the troubles with finding them in New York City. The women always said they had a hard time finding decent men in this city, but I had to believe finding a decent woman was just as hard, if not harder.

  Even though I hadn’t had many actual relationships, I had always hoped I would meet the girl of my dreams and settle down and have children someday. It had seemed inevitable that I would meet a nice girl sooner or later. But as I slid down the hill toward forty years of age, I felt a little twinge of uncertainty at the idea I might end up like Merrick.

  I was thirty-seven and had no prospects for settling down in my future. I really didn’t want to be one of those perpetual bachelors. Merrick had just turned 40 years old, and he was clearly happy with his single lifestyle. That wasn’t me. I wanted a woman to come home to. I knew it deep down; I just wasn’t sure how I was going to ever get it. New York wasn’t the best place to find a woman, even though there were millions of them.

  “So what’s different about your app compared to the mainstream sites? I just don’t understand what you mean,” Dean asked Ren.

  “You should join and give it a try. Basically, the app will get to know you and then find a match based on the real you that it has gotten to know. No trying to pretend like you enjoy long walks on the beach and stuff like that. The app can tell where you go workout, have lunch, work, and party. It’s a form of artificial intelligence, and the success rate is over 90% within six months.”

  “What’s considered a success?”

  “A committed dating relationship.”

  “And the app just matches you based on the places you go?” I asked, now getting a little more interested in what was going on with Ren’s dating app.

  “Not at all. It’s a complex technology that’s totally new in the field. Trust me, and give it a try. I’ll even walk you through it if you’d like.”

  “Will the other person know all the places I’m visiting? I don’t want some sort of stalker.”

  “No, the app will give locations that the user should try out, but they aren’t all places that a match will be at. There are lots of options, and the app doesn’t even have to match you up with the person you picked. If the algorithm thinks someone else is a better match, it will work to connect you with that person first.”

  “This is some sort of serious voodoo,” I said with a laugh.

  “Yeah, and you don’t get to see the other person’s photo until the match has been confirmed.”

  “What?” Dean yelled as he joined the conversation.

  “Yeah, you’re matched based on the information, not on a person’s looks,” Ren said proudly.

  “That sounds horrible,” Luke added.

  “Wow, I’m not sure I could do that. How would you even know that you ran into the right girl?”

  “You won’t. The point of the app was to put you in the right place at the right time so you could make the connection, but it’s totally possibly you’d meet some other girl and decide she was the right one.”

  “Basically, it’s Russian Roulette with your dating life.” Dean laughed, and Luke joined in.

  I could tell we weren’t going to be getting a ton of work done that day, and that wasn’t all that unusual for us. Our little investment club had grown and shrunk over the years; we were learning, and my whole goal was to help others feel confident in their money management. At the moment, we only had five people in the club, and that included Merrick, who never showed up.

  Most of the guys we had before stopped coming when they started making good money in investing. I didn’t mind at all, though. Learning to control your money was the goal of The Triple T Investing Club. We required a $100,000 investment just to get into the club, so it kept the riffraff away and ensured only people who were truly dedicated to learning the craft would join. Since Merrick and I were so high up at Stanley and Associates, I couldn’t invite people from there. Plus, if they already had a job in investments, then they usually knew all the tricks and tips we were going to be talking about.

  What I needed to do was find wealthy guys outside of the investment world, who wanted to be in control of their own money and not let an investor do the work for them. That was a small crowd of people for sure. Usually, the rich were just fine with someone else managing their money.

  “If we aren’t going to be investing this week, let’s at least talk about recruiting. We need to bring some fresh blood into the club.”

  “I talked to a guy at the gym, but the initial investment was way out of his league. Are we looking at decreasing that?” Luke asked.

  It was a good point. $100,000 was a lot of money and made it hard for people to get into the club. But I didn’t want the club to be easy to get into. The free investing advice that went on in our meetings helped us each make thousands of dollars each month. Not to mention how large our club account had gotten over the years.

  By not allowing people to withdraw their money in the first year, we forced dedication to the group. Our investments were making money every month, and that meant that so were we. I liked the current buy-in amount, but I liked when we used to have twenty guys in the group as well. It was certainly worth considering the lowered investment so we could get some fresh blood.

  “How about this; if you find someone who is interested in buying in at fifty thousand dollars, bring them to a meeting so they can see what we do and how it’s organized. I’ll talk with them, and we can consider them on a case by case basis. Deal?”

  “Yeah, I think fifty thousand will open up a lot more of my friends at work. Are you still against having Stanley and Associates traders?” Luke asked.

  I liked
Luke, but unfortunately, I didn’t like others at the office knowing all my personal business. There was no way I wanted to allow Stanley and Associates traders into the group. But I had moved on to managing my own fund now and really didn’t have a lot of contact with the younger associates. Hell, I didn’t even see Luke during a regular day at work, and we were friends.

  “I’ll consider them, but only if they are stand up guys, Luke. Don’t bring in some jackass who isn’t willing to learn.”

  “Deal,” he said with a little smile.

  Luke had always been willing to learn. He knew that he didn’t know it all, and that humble personality was why I liked the guy when we first met. I wasn’t about to let jackass know-it-alls start coming to our group and certainly not guys who couldn’t afford the $100,000 investment. If they were only going to pay half of that, they better damn well have a decent personality.

  “Okay, guys. Let’s get focused here. We need to make a couple of decisions on the portfolio before we can call it a day. Open your notebooks to our long-term holdings; I’d like to discuss your opinions on thinning that part of our portfolio out.”

  And just like that, I was back into my natural habitat; money.

  Chapter 4

  Dakota

  “Yes, yes, fucking yes!” I heard Emma screaming out as I opened the studio door.

  It wasn’t a shocking sound. I wasn’t fazed at all actually. The only thing surprising about hearing Emma moaning out while screwing some guy was the fact that they were still going at it as the sun had started to come up. Usually, she and her boy toy of the night would have fallen asleep by now.

  Emma loved to bring guys back to the studio instead of her apartment. She said it creeped her out when they knew where she lived. I never really understood why she didn’t get creeped out when guys knew where she worked, though; that seemed just as intrusive, especially since she owned her own dance studio.