Longshots. Have you ever had one off big for you?

Years ago, I had a friend who took some time off to travel around the country on his motorcycle. After a few months, he left Denver and was riding the backroads headed back East. He wanted to explore the West Coast, but he was low on funds.

As he came around a curve he saw a line of cars turning into a track that had signage promising an afternoon of horse racing.

He was no stranger to horse racing and the placing of a well-thought-out wager.

He left himself just enough money to get home and put the rest down on a well-priced exacta.

It hit.

The next day, he was headed back across the Rockies to spend several months cruising up and down Pacific Coast Highway.

One smart bet with a huge layout and the adventure continued.

The key was he was willing to accept the loss and return back to Baltimore if it didn’t work. He knew the risk, would easily survive the loss and made the bet.

When oil was below zero during the early days of the pandemic, I noticed that the founder and CEO of a company was pouring more money into his company’s stock at about $2 a share.

The stock eventually went to over…

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