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Tech goliaths outmaneuvered at D9 conference

Upstart punks fly rings around established company CEOs at exclusive tech confab.

I saw every interview, save one, live at the D9 tech conference (full coverage). All were well worth the attention. At this event, invited speakers are interviewed by either Walt Mossberg or Kara Swisher, or sometimes both together. The format effectively cuts through the bluster and prepackaged messaging you might otherwise get from the powerful CEOs on the stage.

It was a great format for CEOs of emerging companies, like Groupon's Andrew Mason, Twitter's Dick Costolo, and Square's Jack Dorsey. But it was murder on the men running embattled old-school tech companies. Let's look at two.

First, Leo Apotheker, CEO of HP, the largest technology company in the world, according to Apotheker. An experienced CEO (from SAP), in the hot seat at D9 he came across as not just ambitious, not just audacious, but borderline deluded. He claimed that HP will be able to build an end-to-end consumer technology infrastructure as Apple has done, but at Microsoft's scale, all based on the WebOS operating system that he's sheltering at HP, out of the way of the standard bureaucracy, lest the WebOS team get infected by what has apparently become The HP Way. Nobody I talked to at the conference had a kind word for Apotheker's performance.

HP CEO Leo Apotheker laid out extraordinarily ambitious plans, centered around WebOS. Asa Mathat/All Things Digital

Adobe CEO Shantanu Narayen started his interview by showing a funny video of himself getting some fake stage presence training. How he managed to convince the D9 team to play this is beyond me, but it was good fun. Listening to Narayen speak, however, left one unconvinced that Adobe can make a healthy transition to a world in which its non-standards-based rendering and online programming technologies (PDF, Flash) are no longer so important.

As with HP, one gets the impression that Adobe is trying to cling to a past that was very, very good to it. HP and Adobe are Innovator's Dilemma poster children, unable to give up old models for a variety of reasons. At a future-focused conference like D9, lumbering companies stand out.

One CEO who did appear to be comfortable in the modern world: Disney CEO Robert Iger. Disney has made its share of mistakes in digital media, which Iger admitted before he laid out not just some realistic product plans for Disney's future but also a healthy openness when it comes to dealing with new distribution partners for its content. Of the old-company CEOs, he seemed most tuned in to what customers actually want, especially when talking about online (cloud) storage of their digital media. One person said to me after his session, "I could work for him."

It's worth noting that Apple's Steve Jobs is on Iger's board. But both HP and Adobe have, in several ways, positioned themselves as direct competitors to Apple. Steve Jobs was not at D9, but his presence loomed over almost every talk.

Two other big-company CEOs, Ralph de la Vega of AT&T Mobility and Stephen Elop of Nokia, had to spend their sessions trying to appear that they were not apologizing for their companies. But they were, and the audience knew it.

If the Groupon IPO doesn't fly, CEO Andrew Mason might be able to fall back on stand-up comedy. Asa Mathat/All Things Digital

While there were fewer upstart CEOs interviewed at D9 than old-line leaders, it was the new guys who carried the hope of the audience. The goofball Andrew Mason, Groupon's CEO in charge of an equally goofy S1, charmed the audience with outright shtick (a "death stare" when interviewer Kara Swisher asked questions he didn't like). Like the thoughtful Jack Dorsey of Square (also co-founder of Twitter), he came across as far more in tune with the modern world of tech, which is social, consumer-driven, and even more fast-moving than it's ever been.

The impression is that the older companies are boxed in. But they don't have to be. Microsoft showed a radical new direction with its Windows 8 demo; and Google's Eric Schmidt, propped up mostly by Android's success, radiated assurance that his company is navigating the new world just fine.

Put together, the collection of D9 conference sessions told the standard tale of technology business: Old tech companies, no matter how big or important they get, are increasingly vulnerable to pressure from ever-smaller companies, as well as to larger changes from outside (new technology, new social and business models) and, most importantly, to lack of change within.