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Part 1 of many. Why you can’t raise money

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You can’t explain your business to a five year old.

Years ago, when I had the best job of my life I worked for an accomplished Wall Street Legend. It was a great experience.

One day I met one of his clients. A tall, lanky Texan. He called everybody “Boy”. He would fly the big bird up to NYC and more often or not crash in the brownstone where my boss both lived and worked. He could have stayed anywhere in NYC but I think he was lonely and liked the company. Over time we got to be friends. One day he said, Boy, “The Arabs made me”. I looked at him with a confused face and he explained that they had all this oil and oil was being sold for $2 a barrel. It cost more then that to bring it up. The Arab Oil Embargo raised oil from $2 to $8 a barrel. He explained this to me as I helped him balance his checkbook. This was 1985. His monthly spend was between $250-500,000 per month.

Hey boy, you want to know how I figure out who to invest in?

He replied, Someone shows me a deal, I ponder it, shake my head and say I don’t get it. I pause. Explain it to me like I’m a 12 year old. They do. I pause, shake my head, I don’t understand it and ask them to explain it to me like I’m an 8 year old. They do. I pause, shake my head, I don’t understand it and ask them to explain it to me like I’m a 5 year old. If they can, they get a check.

After I have known him for a year and we got friendly I picked up the ringing phone and he was on line. As soon as he said, “Boy”, I knew it was him. I’m coming to NYC. Can I pick you up from the airport? “Boy, I don’t fly commercial”. Feeling that we were friends enough i asked him, “Can I borrow the jet?”. There was a long pause. “Sure, Boy, where do you want to go?”.

Paris was wonderful that time of year.

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