Yahoo was always trying to position itself as a media company rather than a tech company. It was a strategic decision to fend off Microsoft -- who was a very very real threat in late 90s. Also, keep in mind that AOL was huge and actually bought Time Warner in an attempt at vertical integration (cable modems, Internet, and content). These decision made lots of sense at the time.

Portals were a big deal. Providing content and being a destination were considered important. They're still important, but apparently being a site that sells classified ads on URL redirects turns out to be a better deal.

He was from hollywood, right? No "tech" experience? In some ways he was right. A lot of "tech companies" are media companies now. Was he ahead of his time? A poor exec?

Yes on the two questions, but for as to exactly why the idea failed, I don't know. I'm an outsider to Yahoo, maybe someone who was there at the time has more perspective. [1]

I just remember thinking at the time they hired him (and still think): "I use Yahoo for products like Groups, Mail, Messenger, and so on, why are they hiring the guy who greenlit Batman?"

[1] - Another article discussing the topic in the meantime: http://www.businessinsider.com/2008/6/was-yahoo-s-terry-seme...

It was Jerry's idea that tech was becoming immaterial and that the web would be just another media conduit. Terry was approached based on this. It was a mistake.

Jerry Yang sought out Semel. Blame Jerry.