The Billionaire Bum

By: Samantha Blair

“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


“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.”

“Shut up, man. Just tell me you’ll do it.”

“Yeah,” he said, “I’ll babysit him for you, but you’re paying me for the whole week even if he quits early.”

“Sure thing. Thanks, Ben.” I flipped my phone shut and put my head in my hands.

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