Even before Cuban stepped onstage, some tech junket veterans seemed ready to be unimpressed. "It's like these people haven't seen each other for three years, and now they're back in the same room together," jabbed Chris Nolan, a former gossip columnist for the San Jose Mercury News who now runs political site ChrisNolan.com.
Cuban is indisputably a tech star and arguably one of the more deserving headliners at Web 2.0, whose roster included such what-have-you-done-for-me-lately veterans as Joe Krause, Brewster Kahle and, as well as genuine powerbrokers like Amazon.com founder and venture capitalist guru .
But Cuban's larger-than-life persona--played out on ABC's reality series "The Benefactor" and on his blog--also seemed to draw a squeamish response from the crowd as a reminder of the hype of the dot-com heyday. After all, this was billed as a coming-out party for the new Web, and the Internet executives and venture capitalists in attendance would much rather forget the excesses of the old.
The audience didn't seem to buy everything Cuban was selling. Even with his foot in one of the more promising technology developments--Web logs--Cuban was heckled by an audience member as being pompous about it: "Uhhhh...He's got a blog!"
Cuban responded by laughing and pointing to his more memorable public appearances in the sports world as the owner of the Dallas Mavericks. "I've never been heckled at a conference before," Cuban said.
To be sure, conference organizers seemed aware of the possibility of a looming hype machine. One panel early Wednesday featured stock analysts mulling the thesis: Is it a bubble yet?
Apropos of a night of vice presidential debates, much of Tuesday evening at the Nikko Hotel was political, whether it was tech executives and venture capitalists rubbing elbows in their renewed faith in the Internet economy or just espousing their campaign views.
Doerr, a partner at Kleiner Perkins Caufield & Byers and a Google board member, pushed clean energy and stem-cell research--a dividing line between the Democratic and Republican platforms--during his evening conversation.
Cuban rocked the house (or the table of Electronic Frontier Foundation staffers) with his sentiments, proposed legislation that is designed to make software developers accountable for copyright theft perpetrated with their technology.
"If you're at this conference, your livelihood is at risk if the Induce Act passes," Cuban said to a round of applause.
He added: "Orrin Hatch (the senator behind the legislation) wouldn't know a computer if it hit him."
Cuban picked up and ran with the ball on one of the conference's hot topics: Web search. On his investment in Mamma.com--a "meta" search engine that few people heard of before its stock surged on the Internet-search hype--he said once it entered into "PIPE level" financing, he had to get out.
Icerocket, a more recent investment, he said was "really just my toy." As on his TV reality show, he bet on the young founders because he simply liked them--and because search is ubiquitous.
On Google vs. Yahoo, Cuban said he liked both companies, but he especially approved of their competitiveness as "great theater."
That could be said of Cuban, too.