Letter From Milo: Bad Judgement

May 12th, 2019

1. I’ve got a friend, let’s call him Joe to spare him any embarrassment, who made it pretty big out in Hollywood. Joe struggled for years before finally finding his niche. He worked as a script reader, tried his hand at acting and failed miserably as a writer before achieving success as a producer.

By way of explanation for you clueless, pathetic losers who aren’t privy to the inside Hollywood shit like I am, the title of “producer” is meaningless. Being a producer is like being a Kentucky Colonel. It’s as much a joke as it is a genuine honorific.

A person doesn’t have to produce anything to be a producer. The only criteria for being a producer is having the audacity to declare yourself one. There must be tens of thousands of people, probably more, calling themselves producers, but only a small fraction of those people have ever actually produced a movie or TV show.

My friend, Joe, is one of the lucky ones. He actually produces films. This is a story about the first film he produced. Against all odds, he ran across a good script, found two bankable actors willing to do it, and rounded up the financing for production.

When it came time to discuss his compensation, the money men offered Joe a flat fee or a piece of the action, whichever he preferred. Now, Joe is no country boy. He is a Chicagoan, born and bred. He understands that making movies is a crapshoot. He also understands that Hollywood bookkeeping is an art form, every bit as creative as writing, painting or musical composition.

Joe opted for a flat fee.

As luck would have it, the movie turned out to be a huge hit, making several hundred million dollars. Had Joe taken a piece of the action, his payday would have been 15 times larger.

The movie did so well that the money men decided to make a sequel. They figured it was a can’t-miss proposition. So did Joe. This time he took a piece of the action. Of course, the sequel turned out to be a huge flop, making about 20 bucks worldwide. Joe claims he didn’t even make expenses.

“The only good thing that came out of it,” Joe explained, “is that now I’m able to produce more movies. You see, making two movies and having one of them be a big hit is an astounding track record in the film business. Now all I have to do is figure out how to make some fucking money.”

2. I have a good friend, let’s call him Bruce Diksas to spare him any embarrassment, who was hanging out in the Pacific Northwest around 1980. He had followed a woman to Seattle in the hope of keeping a romance alive. The woman had enrolled in graduate school and spent most of her days in class or studying, so, Bruce found himself with a lot of time on his hands. And, like any ambitious, industrious, hard-working young man, Bruce decided to spend his free time in one of Seattle’s many legal poker rooms.

Now, Bruce is a pretty good poker player, but, like all of us who enjoy the game, he thinks he’s much better than he really is. He usually lost more than he won. Despite his bad luck, Bruce enjoyed his time at the tables, Playing poker all day was a very pleasant way to pass the time.

One of the main topics of conversation at the tables was a small business located in a storefront across the street from the card room. It seemed that the business was a source of local pride. It was growing rapidly and would soon be going public. A few of the players at the tables discussed the pros and cons of investing in the company, buying a few shares to help out the local boys.

Out of curiosity, Bruce stepped outside to check out the storefront. He was thinking about sinking a few hundred dollars into the company, just for the hell of it. As soon as he saw its name on the storefront window, however, Bruce, knew that the company had no chance of success. It was a stupid name. It made no sense. Shouldn’t a company’s name say what it does? Shouldn’t it at least be catchy, something that sticks in the mind? Why even have a company if you can’t give it a decent name? Any company with a name like that was doomed to failure. He’d be better off investing in lottery tickets.

The company’s name was “Microsoft.”

“I still say it’s a stupid name,” Bruce says to me years later.

“A lot of those internet companies have dumb names,” I reply. “Look at Yahoo or Google.”

Pouring himself another drink, Bruce says, “You’ll notice I didn’t buy any shares in those companies, either.”

3. I’ve got another friend, let’s call him Milo to spare him any embarrassment, who, in the mid 1970s, lived in a coach house on Burling Street just south of Armitage. The neighborhood, in those pre-gentrification days, was still very rough, gang-infested, with run-down buildings everywhere. Milo shared the place with his friends Bruce Diksas and Wayne Gray, and they split the 80 dollars a month rent.

Granted, 80 dollars a month was not a lot of money, even in the 1970s. Still, it was not always easy coming up with the 27 dollars apiece every month. None of the boys worked regularly and what money they scraped up was usually earmarked for drugs and alcohol, and occasionally a greasy hot dog at the Doggie Diner on Armitage.

The property was owned by a retired bartender named John, and he didn’t mind if the boys were late with the rent once in a while. Milo, Bruce and Wayne were a scruffy, eccentric and endlessly entertaining trio, more Stooges than Musketeers. The old barkeep enjoyed their company, joining the boys for backyard cookouts and drinkfests. One of the boys even talked John into smoking his first joint, which, to the old man’s surprise, he enjoyed immensely.

Sadly, John’s health began to fail. He couldn’t take care of the property anymore. Just walking up and down the stairs had become a chore. It was time, he decided, to sell the property and move into the Polish Eagle Nursing Home in Marquette Park.

John offered the property to Milo for $32,000. Think about it. A two-flat with a coach house in the DePaul/Lincoln Park neighborhood for a little over $30,000. Even though he had no money, Milo could have easily purchased the place. As a military veteran he could have taken advantage of the G.I. Bill and bought the property with no money down.

After giving it a little thought, Milo decided NOT to buy the place. When someone asked him why he chose not to buy, Milo haughtily replied, “I’m not into property, man.”

Those five words have haunted Milo for years. The property that he refused to buy for roughly 30K, is now worth in excess of one million dollars.

Sometimes, when Milo tells the story of his lost real estate opportunity, someone will ask, “If you weren’t into property, what exactly were you into?”

Milo always ruefully replies, “At the time, I was into stupidity.”

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