Career Confidence

1Life's a Gamble

My grandfather was a bookie.

For anyone who doesn't know what that is, he took bets on numbers, sports, and a variety of other chance games.

He was not big time. Most bets were done in the form of nickels and dimes.

His customers were mostly poor people who were throwing their coins into the proverbial fountain, hoping to come out with a few extra dollars.

Which is funny because he was poor too.

His day job was working in a factory where they made tennis balls. And on nights and weekends, he bartended and waited tables at our hometown Italian restaurant.

On Saturday mornings we would go around and pick up money. Then he would go to the bank, deposit the loot into a safety deposit box, and then he'd take me and my sister for ice cream.

At the time, I had no idea what was going on, but I knew that Saturday mornings were fun, and the people we visited often had treats for us.

Do you remember the line from Goodfellas where Karen says something to the effect of: “Other men were sitting around every day waiting for handouts from their bosses at the end of the month. Mobsters were different. They went out every day and came back with money.”

It was like that, but without the violence and the huge stacks of cash.

All I know is that my grandfather was a hustler. Any job, any opportunity to make money, any work hours, requests, side gigs were always met with a resounding “yes.”

My earliest memories from childhood include picking up cash and playing cards for money. We ...