The Billionaire Bum

Jackson Hayes, brilliant real estate tycoon, entrepreneur, and financial genius, was walking home from work. Admittedly, this was a rare event prompted by the early springtime weather coupled with an extremely irritating late-afternoon meeting.

He was in the process of purchasing a company owned by none other than Mr. Nicholas Carver, a shrewd businessman who had repeatedly made appearances in Jackson’s life, much to Jackson’s dismay. Nick seemed untrustworthy and never failed to set Jackson’s teeth on edge, but his company did appear to be a good investment. The board of Hayes Enterprises was pushing for this acquisition despite their young CEO’s doubts. The due diligence checked out, and pending any further information, the deal was scheduled to close in less than thirty days.

Jackson loosened his tie and threw his perfectly tailored jacket over his arm for the hike across town. He was looking down at his over-priced PDA and absentmindedly running his fingers through his disheveled hair.

Half a block ahead a retired Vietnam war veteran, who had come across some rather hard times lately, was sitting on the sidewalk stretching the tight muscles in his right leg, and holding a cup for change. Some aches, it seemed, never went away.

Perhaps if Jackson had looked up, he might have noticed the man sitting on the sidewalk with his legs outstretched, but as it was, he literally stumbled right over him. A startled, “What the…?” escaped his lips before he scraped one palm against the sidewalk and managed to right himself. The man that he had tripped over tumbled sideways, spilling loose change from his cup.

“Watch where the hell you’re going,” he growled, frantically collecting the spilled coins.

“Don’t sit in the middle of the fucking sidewalk,” Jackson spat in return.

“Fucking self-absorbed asshole…” The man’s mumbled sentence faded off as he righted himself and went back to shaking his cup.

Jackson could have simply ignored the man and went on his way with no further thought, but this day had been frustrating enough, without adding insult to injury from a filthy street bum, and Jackson had never been one to back down from a fight. Before he knew it, the argument was falling from his lips.

“What did you call me? Self-absorbed? Fucking self-absorbed? That’s rich coming from a man with no work ethic who doesn’t even pay taxes. You’re a fucking drain on the system, and you think I’m selfish? At least I take care of myself. What the fuck have you ever done?” The homeless man stood slowly, ignoring the pain that the action caused, and looked Jackson dead in the eye. Our dear Mr. Hayes couldn’t have known it, but this man had seen far worse in his sixty-odd-years than the likes of an uptight businessman. Where Jackson expected to see shame he instead saw perseverance. These were the eyes of one who never gives up, no matter how broken.

“You’ve been handed everything your whole life, pretty boy. You wouldn’t survive one week living like me.” With that closing remark, the man turned and limped away down the street, leaving a speechless Jackson alone on the sidewalk.

Jackson’s phone vibrated in his hand, pulling him out of his stunned silence.

“Hello,” he answered coldly.

“What’s up my brother?” Jason’s boisterous voice echoed through the phone.

“Nothing.”

“Good, we’re having a night out. Shelby is off at some fashion show thing, and you know I can’t cook for shit. I’ll meet you at the Phyrst in half an hour.” The line went dead.

Jackson looked up at the street sign. He was still ten blocks from home, and it was a ten-minute drive from home to the bar. It looked like he’d need that cab after all.

Chapter 1: The Bet

Jackson

I felt decidedly better after a change of clothes and draught lager. My brother Jason had a natural ability to cure me of whatever funk I might be in, and I found myself very glad that he had called me out for burgers and beer. We’d been comparing our days back and forth for the last few minutes.

“..so then the guy has the audacity to call me a self-absorbed asshole,” I said. “Can you believe that? When he’s the one practically lying in the middle of the street?” Jason chuckled and shook his head, taking a long swig of his beer.

“And then,” I continued. “And then, when I called him on it, he tells me that I wouldn’t survive one week in his shoes! It’s like he thinks being a bum is hard work or something.” I paused while the waitress set our burgers in front of us. “This looks so good. I was freaking starving.”

Jason was still shaking his head and laughing across the table. “He’s right though.”

“Who’s right?”

“The bum. I mean being homeless is hard. I sure as hell wouldn’t want to try it.”

“What?” I paused with my burger halfway to my mouth. “You think sitting in the middle of the damn street all day is difficult?”

“Well no, man,” Jason said, “but it’s no picnic either. You know how much I eat, and I wouldn’t want to be worried about where the next meal was coming from all the time.” I smiled at my brother. He wasn’t kidding. The man had two burgers and a huge pile of fries in front of him right now, but I knew that they wouldn’t last long. Jason was built like a tank. He stood six foot six and was known to fill an entire doorway with his broad shoulders.

He could pack away food like no other.

“Well yeah,” I agreed, “but you could just get a part-time job in a burger joint and you’d be set. I’m sure you could eat all the customer rejects.” I watched as he shoveled a few more fries into his mouth. “I mean why don’t those people just get jobs and stop bothering the rest of us who are willing to put in a decent day’s work?”

Jason’s face took on a tone of seriousness that I wasn’t really accustomed to. “I don’t know, man. I don’t think it’s that simple. Would you hire a homeless guy?”

“Well, of course not, Jason, but we’re in business acquisitions. There has to be some kind of more appropriate employment for these guys, like manual labor type work.”

“I don’t think so, Bro. I’m not saying that I like being pestered by them out on the street begging, but I think living a week as a homeless person would be hard. I’d give you about twelve hours out there with no credit cards, and I bet you’d have a lot more sympathy for them.”

“No way.” My brother was looking at me like I’d grown two heads. “There is no fucking way that I would just give up like that. If I were homeless, I would find a way to work to better myself. No way in hell would I settle for begging in the street. I would fare so much better than any of these lousy drains on society.”

Jason smiled his typical, huge, goofy smile at me, and I knew that I was in trouble.

“Fine man,” he said. “I’ve got $50,000 that says you can’t last one week as a homeless dude.”

“What?” I asked, my burger long forgotten.

“You heard me.” He was fucking laughing at me now. “I’ll bet you fifty grand that you don’t make it one week going homeless. You leave here tonight and give me your keys, your credit cards, everything. Hell, I’ll even let you keep the cash that’s in your wallet and your driver’s license, which is probably more than most homeless guys start off with. One week from today, I’ll give it all back to you, if you don’t come begging to me to have it all back before then.”

“You can’t be fucking serious,” I said. “I’m in the middle of closing the Carver deal. I can’t just take off to go be homeless for a week.”

“Sure you can,” he said. “When was the last time you took a vacation? I’ll tell everyone you had the sudden urge to see Hawaii. You and I both know that you’re spending too much time stressing over that deal anyway. The board already made the decision. The deal will close just fine without you, and even if it doesn’t, you didn’t want to buy the damn company in the first place.”

He was right. I was usually very heavily involved in the beginning and ending stages of an acquisition, but there was always a little lag time while the lawyers fought with each other when my presence wasn’t strictly necessary.

It had been a long time since I’d had a break from my ordinary routine. Jason and I used to pull crazy shit like this all the time in college. It had been too long. Maybe this would be fun.

“Deal,” I said. “Fifty thousand dollars says I’m perfectly fine at the end of one week of being homeless.”

Chapter 2: Bodyguards and The First Night

Jason

“No, I just need you to follow him around at night. Just make sure he doesn’t get his ass killed,” I said.

Ben was cracking up on the other end of the line. “You want me to follow your dumb-ass brother around for a week while he’s pretending to be homeless? You rich people are so damn weird.”