The Billionaire Bum

By: Samantha Blair



Having time to kill was an unusual experience for me. I was itching to check my email or at least place a call to my personal assistant. Time moved so much slower outside of the corporate world.

There was a small park across the street with a fountain and couple of park benches. It was an appealing place to sit and wait. The rain had stopped temporarily, but the benches were still wet. I wiped the rain off as best I could and then perched precariously on the driest edge of the seat. I unfolded my newspaper in front of me. If the bar-tending job didn’t pan out, I would try the dishwasher next. It was on the way to the shelter anyway.

Maybe I could get some lunch, too. Those pancakes weren’t holding me.

Finally, a middle-aged man stepped out from the bar and unlocked the door. I walked across the street.

“Good morning, sir,” I said, extending my hand. “My name is Jackson. I was hoping to apply for your open bartending position.” He shook my hand and let his eyes sweep over my form. I was hoping that I looked young enough to pass for a recently graduated college student.

“I’ll give you an application,” he said.

I sat at the bar and filled out the application with a borrowed pen. Permanent address.

Well that was going to be a problem. I couldn’t exactly tell him that I lived in the penthouse suite of the highest-priced apartment building in this city. I had other homes as well: a beach house off the coast of South America, and a ski chalet in Tahoe, but neither of those would work for this application. Could I list my parent’s address? I wrote it down.

Phone number… Shit, Jason had my phone. If an employer wanted to call me, I would be virtually unreachable.

Work history… Yeah, I’m the CEO of one of the most profitable companies in the United States. I was clearly going to have to edit my work history. Fuck, this is going to be impossible.

I finally settled for making everything up. I gave my parents’ phone number. I was going to pretend to be still living at their home, but I would have to do everything that I could to keep him from calling their house. I could just hear my mother now, “Why is my son applying for a job at a bar? Are you sure he didn’t want to buy your bar? Would you consider it an investment property?” That would not be good. I was going to have to talk my way out of this before it came to calling anyone.

I can do this.

I was a Princeton graduate for God’s sake. Of course, my application named a local state system university instead, but somehow I didn’t think that it would matter for a position pouring drinks. Surely, I could bullshit my way through one lousy interview.

“Sir?” I said, putting on my most professional and respectful demeanor. “I’ve finished the application. I was hoping that you might have time to conduct an interview now, if everything looks acceptable, of course.”



He took my application and skimmed it briefly. “You’ve never tended bar before?”

“No, sir. But I did work in a pizza shop for a while where we served beer.” It was a lie. I had interned with a large commercial real estate firm for a year when I was in college. That was the closest I’d ever come to this line of work, which wasn’t very close. He gave me a non-committal grunt. I was going to have to do something in a hurry or this interview was going to go downhill fast.

Just then the door opened and two beautiful young women stepped through. The bar was open for lunch and the two of them, probably co-workers, appeared to be here for sandwiches and possibly cocktails. I could do this. I put on my very best smile and then turned to my new customers.

“Hi, come on in,” I said, throwing the full weight of my inherited Hayes charm at them. I grabbed a couple of menus from the bar and ushered them to a table. The owner hadn’t stopped me yet, and I was too afraid to look over my shoulder for his approval. I handed the girls the menus. “What can I get you lovely ladies to drink?”

One of them giggled and one of them blushed. Yes! Even homeless I could charm the pants off of them. I allowed myself a brief moment to finish that fantasy before they answered.

“Captain and Coke,” the first one said. I looked to the other.

“I’ll have a Bud Light in a bottle please.”

“Coming right up,” I said.

I turned back to my interviewer. “Captain and Coke and a Bud Light in a bottle?” He burst out laughing. “Yeah, all right, smart ass,” he said. “The beer is in the cooler in the corner. Captain’s right here, and the Coke is in the tap.” He handed me a glass, pointed to the ice and then showed me how to measure and pour the drink. “Give the girls their drinks and get their order. Then we’ll work out the terms.”

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