Back on December 27th, 1999, Microsoft (MSFT) closed at $53.60/share.  At the time, MSFT was the largest company in the world and the Dot Com boom was raging.  The main concern for investors as 1999 came to an end was definitely not that a bubble was about to pop.  Instead, it was whether or not our global computing systems could handle the Y2K bug.

The Y2K bug came and went with no real issues as we crossed into a new millennium, but the problems were just beginning for Tech investors.  Less than a year after hitting its all-time high at the end of 1999, Microsoft’s stock price fell more than 60% from $53.60 down to $20.

From its lows of the Dot Com crash to its highs prior to the peak of the mid-2000s bull market, MSFT failed to pick up much steam.  Then it was knocked back down into the mid-teens by early 2009 when the Financial Crisis was at its peak.  As the world recovered in the early part of the current bull market, MSFT failed to do much, but since the start of 2013, the company has been a big winner.  Now, after a huge upside earnings report last Friday and another gain today, MSFT is FINALLY set to close at a new all-time high.  If you’ve stuck with it over the last 16 years, congratulations on finally getting back into the black!

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When MSFT was last at its all-time high, its market cap was just over $600 billion.  Due to the company buying back its own stock over the years, its market cap is not making a new all-time high today along with its stock price.  In fact, MSFT’s market cap is about $200 billion less than it was when it last peaked at the end of 1999.  And while not all stock buybacks work out so well, MSFT’s purchases all came between 2004 and 2013 when the stock was viewed as “dead money” by most.

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