Yahoo’s biggest “problem” is the huge revenue and profit it continues to make. Jobs had a big advantage when he came back to Apple – it was losing $1B/year and was about to go broke. Everything needed to change. When you have a huge business to screw up, it isn’t so easy to make a sweeping change that could disrupt the business model for years. At Yahoo you could probably cut back to 100 ops people and 200 sales people and rake in billions in revenue and profit for a decade or more. In fact, most Yahoo! die hard users would like the message “We are never going to change Yahoo! again. It will remain exactly like this from now on. No more redesigns. No new features. No changes of any kind. Your My Yahoo page is safe.” Yahoo’s business is driven by the adoption of Yahoo! Mail. Most people that use it (it is the largest email provider in the US), don’t realize they could put in mail.yahoo.com rather than yahoo.com so stop there on their way to their inbox. That is enough to power nearly every other media site they control to the #1 position with the right mix of articles on the home page.

—Spot-on analysis of the challenge facing Yahoo. They’ve got a huge legacy user base that never wants them to change anything. Maybe Yahoo was a perfect fit for Microsoft after all…