When I quit comedy I needed a fresh start. 

As you may recall from my fateful chat with Mrs. Kravitz in Los Angeles, at the end of my stand-up journey, I didn’t know what I wanted next, so I was starting with what I didn’t want.

I no longer wanted the grueling uncertainty of success as an artist. 

Waiting for someone else to come along and decide I was “worth a shot.”

Whatever I did next, I would have some control. 

But first, I had to figure out how to earn money beyond talking dirty to drunk people in dark night clubs.

I tried it all… construction (demolished a rusted boat dock with a small tool box), strip club DJ (nightmare!), bartender (good gig, I was bad at it), hotel bellhop (fascinating people study, shit pay)…

All “no resume” jobs where misfits like me could make a quick buck, if you were willing to hustle and could avoid getting fired. 

Aside from quitting comedy and reimagining my future… Three major life events had taken place around this time…

My mother died at age 49 from a brain aneurysm.   

I married the girl I always hoped to marry. 

We moved from Chicago to Florida to start a family – and be close to family. 

During this time, I had a single burning question about life:

What causes some people to give other people money?

So basic, right? 

But, I had no idea, beyond bits and clues from a few savvy comics I’d toured with, how this whole “business” thing worked. 

Which is odd because both of my parents had been business owners. 

My dad co-owned and operated Kenwood Auto in Dracut, MA, and my mom owned and operated several beauty salons throughout her life. 

As a kid though, I just saw it as their “jobs,” and I think they did, too. 

I don’t recall any talk of greater ambitions. Expanding into new locations. Hiring managers so they could have days off. Advertising to a more profitable customer, or any customer at all. 

They were glad to have the work and not have a boss, but, from what I can tell, they did not become bosses. 

Never really owned it, just ran it. 

All the stress with none of the glory. 

So, at 30, my new life in front of me, a family in the works, I began interrogating anyone I met who seemed to have the answer to this “getting money” conundrum.

If I found myself in a nice house I’d grill the owner… “What kind of work do you do?” , “So, how does that work?”, “How did you get started in that?”, “Did you learn that in college?”

It seemed there was no ONE path to money. 

But, there was definitely a mindset around it. 

I was beginning to see that people who had money were not only willing to work hard, but they were the kind of people who dared to ask, 

“Why not me?”

I thought about my Uncle Jerry.

Jerry knew how to get money. 

I didn’t know exactly what he did, something with real estate, and he had important friends in politics, always wore nice clothes, kept his hands clean – the nails neatly trimmed. 

Jerry has a great smile and affable vibe, but you could tell he knew how to close deals over a cigar. 

Out of the blue, I called Uncle Jerry.

He was surprised to hear that I’d like to drive an hour to the Florida town where he and my aunt “wintered” and meet him for lunch – just the two of us.

I was sure he thought I was going to ask him for money and I did not relieve his concern on the call to confirm our meeting. 

I wanted to hear how he approached the situation under that assumption. It was a valuable clue into how money people think and operate and I didn’t want to miss out on it.

I’ll never forget Uncle Jerry’s first line to me when we sat down at the restaurant.

It sent me on the quest of a lifetime. 

And that’s where I’ll pick up next Sunday. 

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