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Curt Schilling was one of my favorite baseball players in the 2000's.  Whether you love or hate the Red Sox, anybody who follows baseball surely remembers the Red Sox ending their 900 year title drought partly because Curt Schilling wanted it so bad that he pitched throughout the playoffs with a tendon so bad that his foot bled and turned his sock blood red.  Regardless of the pain and the blood, his performance helped the Red Sox win the 2004 World Series.

He was a dominant force before and after that and the ‘Bloody Sock' is one of the icons that shows his talent and his heart of a champion.

Unfortunately, that didn't carry through for very long in his post-baseball career.

After retiring from baseball, Curt decided to form a video game company.  He invested just about every penny he had saved from his baseball earnings into this company.

It went belly up.  Recent reports indicate that all of the money that he made from baseball is gone.

Imagine that.  Being one of the best pitchers in the game.  Having one of the most iconic pieces of clothing enshrined in the Hall of Fame (that's where one of the bloody socks ended up).  Representing the force behind ending a decades long curse.

Only to lose every dollar that's associated with it.

What a mess.

Here are the three things that I think Curt Schilling did wrong with the whole video game fiasco.

  1. Got involved with something that he wasn't an expert at – I've heard that Schilling was a gamer.  He loved playing video games.  Cool.  Maybe he loved playing them and beat all the other players in the clubhouse and on the team planes.  I don't know.  Even if he was the master at playing video games, I can't really imagine that Curt Schilling was a seasoned video game developer.  Chances are he had people pitching him ideas and decided to act on it, but did so without the expertise and knowledge that someone forming this type of company and making this type of investment should have.
  2. The investment itself – Speaking of making an investment, what was he thinking investing everything into this company?  You often hear success stories of people starting a company with everything they have and turning it into a roaring success.  That's all fine and good if you have a few thousand bucks, but he lost fifty million dollars.  Fifty million.  That's insane.  If he wanted to get involved in the video game industry, fine.  Let him have his fun.  But, under no circumstance should he have invested any more than $10 million dollars.  He should have found investors to make up the rest, and if he couldn't, maybe that would have clued him in that the idea he was working on wasn't a winner anyways.
  3. The blame game – The story of the investment goes that Rhode Island made an investment into his company with the promise that the company would provide 450 jobs to Rhode Island residents.  When things seemed to be going south, someone in the political system talked about the problems.  This essentially shut the video game company down.  Schilling said that if this information hadn't been disclosed, he could have found investors to keep things going.  In other words, he was putting his own mistakes on others.  I don't buy it.  If he was playing the blame game at the end, chances are he was delusional the entire time that things were headed south and his money was going out the window.

Where will Curt Schilling go from here?  I have no idea.  Will he be penniless?  Somehow I doubt that.  But, maybe his retirement will be going around and charging for autographs.  I know many former stars can make a living doing that, but nowhere near the lifestyle and security that $50,000,000 (or even $40,000,000 had he followed my second point above) would have offered.

From bloody sock to a bloody mess.

And it really could have been avoided.