“How much are you making per week working at the hotel?”

I was sitting across from Charlie behind his desk inside a ramshackle office building in Pinellas Park, FL. A shithole, pass-through town of ragged stripmalls occupied by auto parts stores and tattoo parlors. 

The intersection of my old life in comedy, and whatever my next life would become, had humbled me into this room.

Retired from stand-up, newly married, and living back in Florida (which I’d promised myself would never happen again when I’d left this weird ass state in 1993). 

I was struggling to transition from road dog club entertainer to “legit” working man. 

Knowing something must be out there for me, but running on fumes of hope, with no evidence of what was on the horizon. 

“On average?” I said to Charlie, sheepishly. “I don’t know… two fifty?”

“Wow!” Charlie exclaimed sarcastically. “One of the best road comics I’ve ever seen is pushing a baggage cart for a thousand a month.”

Then punctuated with, “That’s fucked up, dude.”

It was fucked up. But, so was living in motels and regurging the same dirty jokes night after night for ten years with zero profit. 

I didn’t regret my choice to leave show business behind, however, I was feeling desperate and he could smell it on me. The same way I used to smell the funk of booze that once oozed from his pores. 

Charlie had just taken me on a “tour” of his business. 

The bulk of it was a large square room filled with makeshift cubicles where pasty-skinned vagabonds wearing headsets slugged Red Bull and dialed phones, doing their best to sound friendly and professional. 

Their target: Timeshare condominium owners. 

The pitch: Rent or sell their timeshare via their “industry-leading” website. 

Suckers being suckered again after they realized they’d been suckered. 

“Listen, man,” said Charlie across his desk – the door closed behind us. “There are five people out on that sales floor who have the experience to help me run this business…”

“But, I don’t trust one of them as far as I can throw them,” he said, pushing his thin blond hair over his thick forehead.

YOU,” he continued. “Don’t know a thing about my business. But, I’d trust you with my life.”

A little over the top, I thought, considering the last time, years ago, that I interacted with Charlie I hoped would be my last. 

“So…” he leaned in, in full glory sales mode now. “I’ll pay you three hundred and fifty dollars a week to sit next to me and learn how my business works.”

It was a compelling offer. 

The extra hundred bucks a week would make a significant difference in my life at that point. 

But, more significantly, was the chance to get a glimpse of how sales and business actually worked in the real world. 

Here, in front of me, was a genuine “fuck up” who’d willed his way into sobriety and building a seemingly thriving business. 

Everything about Charlie and the slimy ecosystem of people even more fucked up than him grinded against my ideals.   

Deep down though, I couldn’t ignore the fact that…

This was the exact underbelly view of society I needed to finally grok the dynamic of why some people give over their money to the people who collect it. 

Business 101. 

Supply and demand. 

Desire vs opportunity. 

All things I’d seen shades of in show business, but never never quite understood. 

When I returned to Florida as a married, thirty-something “start over” scanning the job ads, the first thing that stood out were the requirements. 

Even for what I considered menial positions, college degrees were “preferred” and high school diplomas were a “must.”

Neither of which I had. 

Going “legit” meant having some documentation of my legitimacy – at least as society at the time viewed it. 

So I enrolled in night classes at a local high school (the very place I’d grown intolerant of twelve years earlier before setting out to live out my show biz fantasy) to prepare for taking the GED. 

I passed, barely. 

Qualifying me to land a degrading job as a bellman at the local Hilton, shagging luggage and shuttling bitchy airline crews to and from the airport. 

Was this the best I could do?

A thirty-two-year-old man with more life experience than most people will have in 70 years, but all of it in a profession that screams “do not hire” on a resume. 

It pained me to accept Charlie’s offer, but it was the best one I’d gotten since quitting comedy, so I took it. 

Next week I’ll reveal how working with Charlie, and eventually becoming Vice President of his company, taught me harsh, but essential, lessons about money, people, and how to come back from the dead (literally) stronger than ever. 

P.S. This starts with the tale of a turbulent friendship with Charlie – jump into the first chapter.

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