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Why is Hotmail not as popular as Google?

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Why is Hotmail not as popular as Google? Hotmail was the foremost free email service when Microsoft bought the company in 1997. Microsoft bought them as a market share play for the 9 million user accounts they had at the time — for approximately $400M, or about $40 per user. This was back when the race was all about acquiring users, and what you would do with those users once you had them, in order to monetize your investment, was “a problem for later”. In other words: prior to the dot bomb. One of the major issues leading to the demise of Hotmail was that Microsoft spent a great deal of effort spinning its wheels. It did this in order to first put HTTP proxy servers in front of the FreeBSD servers upon which Hotmail was originally built so it would look like they were all running on Microsoft technology, and then replacing the FreeBSD servers on the back end so that they actually were running on Microsoft technology. Rumor has it — and I knew casually the p...