The decline and fall of Yahoo

Like a child actor, Yahoo has always lived its life in public — and suffered for it. Its April 1996 IPO, when the company had a mere 49 employees, cast it in the spotlight long before it was ready. And like Hollywood, the stock market looks coldly on a fallen star. Microsoft's offer of $44 billion is less than the company was worth in October 1999 — before the tech-stock bubble's grotesque inflation more than doubled that to $97 billion. It has never regained its swagger.

That early IPO — a preemptive strike against long-forgotten competitors — was a blessing and a curse. It was great PR, but it also meant that Yahoo had to please shareholders from an early age.

In the '90s, it did so with aplomb. No one personified Yahoo's cockiness more than its president, Jeff Mallett. A former soccer player, Mallett was more often the public face of the company than its reticent CEO, Tim Koogle. He often was quoted when Yahoo struck a large advertising deal; he was an expert at squeezing cash and stock from startups desperate to get traffic from Yahoo. Mallett had his share of mistakes, like the $6 billion purchase of Broadcast.com from Mark Cuban in 1999. But he was, at the least, bold and decisive.

Terry Semel became CEO in 2001, pushing Mallett aside. A new management team came in, full of ad-sales specialists. From 2001 through 2005, Yahoo patiently courted Madison Avenue, building a formidable banner-ad business with blue-chip clients.

Semel also got Yahoo into the search business, buying Inktomi and Overture. But he failed to capitalize on their promise. Many insiders blame Sue Decker, then Yahoo's CFO, now its president, for milking those businesses for cash while Google was investing millions in its algorithms. Semel's other big acquisition push into user-generated content brought it properties like Flickr and Del.icio.us. But it stalled when prices started to rise in 2006. Semel balked at paying big prices for YouTube and Facebook, and they slipped from his grasp.

The rise of Sue Decker roughly parallels the decline of Yahoo. Decker is — no, was — an expert at catering to Wall Street, and a killer at board-room politics. Insiders believe she edged out Dan Rosensweig in a 2006 reorganization. She then, they say, lobbied the board to oust Semel as CEO, using Rosensweig's departure as part of the rationale. Cheeky, but clever.

Both moves backfired on Decker. She'd hoped to put Rosensweig in a lesser role, but he balked and left the company without anyone running its content businesses. Semel left, but Decker did not get the CEO job she'd hoped for. Instead, the company was left looking rudderless, with founder Jerry Yang stepping in as CEO.

Another Decker mistake: Her disgraceful treatment of Wenda Harris Millard, the company's beloved U.S. sales chief. When Millard told Decker she was leaving for Martha Stewart, Decker reacted furiously, locking Millard out of her office and issuing a press release that suggested Millard was out of touch and had been fired. Unsurprisingly, Yahoo's banner-ad sales have suffered since Millard's departures.

Which brings us, more or less, to the present. It's not surprising that Microsoft seized this moment to issue its $44.6 billion offer. Yahoo's poor earnings and gloomy forecast provided one opening; management's incompetent dithering over layoffs provided another.

It's possible that Yahoo might somehow escape Microsoft's grasp. But whatever course Yahoo takes from here, it's clear that it will be even further diminished. Yahoo will be best remembered in business schools, where it's taught as a case study: How quickly tech empires can fall.