Bill Gates on Jon Stewart's Daily Show: Vista Blitz

Datamation content and product recommendations are editorially independent. We may make money when you click on links to our partners. Learn More.

It promised to be one of the stranger conversations in recent TV history.

On one side of the desk, Bill Gates, the world’s richest geek, a brilliant and aggressive competitor who played so hard that the U.S. government stepped in and declared the company he led a monopoly. A man not known for casual chitchat and easy laughter.

On the other side, Jon Stewart, a left-leaning TV host whose sometimes goofy sense of humor accompanies a penchant for tweaking the powerful and famous. An interviewer who relishes the unscripted question.

Yes, oddly, Bill Gates decided to go on the Daily Show. You knew his motivation had to be compelling. The software titan rarely allows himself to be in a public situation that’s not tightly controlled, much less the set of a live-taped TV show hosted by an irreverent comic.

The reason, of course, was the launch of the long-birthed Vista OS, due for release just a half-hour after the Daily Show’s airtime. Whatever you think of Gates, you have to hand it to him: after all these years he’s still willing to do whatever’s needed to sell Microsoft.

The problem is, it’s harder to sell Microsoft than it used to be. The release of Vista to corporate users, in November, was met with a collective yawn. “Possibly next year – or the year after” was the enterprise’s attitude toward upgrading.

As for consumers and Vista, the consensus seems to be that most users will wait for a new PC to upgrade. Compare that to the old days, when breathless fans lined up at midnight to clutch Windows 95 as soon as humanly possible.

But it’s not 1995 anymore. The Internet has grown up into a robust child, running around the room knocking over most everything, including – possibly – Microsoft’s business model. Internet-based software-as-services (SaaS) challenges Microsoft’s primacy. If your apps are reduced to the services they provide – with no on-premise installation – won’t that destabilize customer-vendor relationships?

Additionally, the rise of virtualization enables computers to run more than one OS, meaning Microsoft is expected to share space with competitors. Speaking of which: Microsoft was pushed into last year’s alliance with Novell because its customers needed Microsoft software to be more interoperable with – gasp – Linux, once just an upstart and now a hard-muscled competitor.

Microsoft certainly has the top talent and market muscle to navigate all these challenges, but the old sense of invincibility is gone. If it’s going to keep on thriving, the company will have to dig a little deeper.

That might be one reason that the figurehead himself, Bill Gates – not the most jocular fellow – decided to leave his immediate comfort zone and go on the ultra-trendy Daily Show.

Ladies and Gentlemen, Bill Gates!

Jon Stewart, in his opening remarks, enthused about having Gates on. “He will explain to us how we will all soon be enslaved by our CPU masters.”

After a commercial break – featuring an ad for iPod – Gates walked out in his trademark pullover sweater and button-down shirt. Someone in the rowdy audience shouted, “Yo Dog!” to which Stewart explained to the smiling Gates, “They’re big Windows fans, my friend.”

Stewart wasted no time before gently poking Gates about how long Microsoft had taken to release the oft-delayed Vista. After Gates said that the last release was five years back, Stewart noted that five years is so long in the tech world that, back then, “People were using abacuses.”

Gates was ready. “Yeah, it’s usually between three and five years, so this is at the long end,” he said, in a statement that must have provoked guffaws among shareholders. “So it’s all the more impactful when it’s done.”

To which Stewart ribbed him about his low-key enthusiasm: “Settle down, sir.”

The conversation moved on to the release itself. Stewart explained he wasn’t much of a computer expert, so he’d need some tutoring.

Stewart: “What does the F12 button do? Does it do anything?”

Gates: “I’d stay away from it if I were you. Start with the F1 and work your way up.”

Stewart: “Does the F12 do something to someone else’s computer?”

Gates: “No.”

Gates talked about the process of incorporating tester feedback as Vista was developed, explaining that fifty families in eight countries, along with five million expert users, gave feedback for the beta version.

Stewart: “What is a beta version? Does that in any way make you sterile?”

Bill’s Pets?

Stewart picked up the shiny new package with the Vista release inside. “What if I don’t know how to use it?”

“Call me,” Gates said, to great audience laughter.

Stewart asked a question he expected no answer to: “What’s your password?”

The Microsoft chairman just smiled, but Stewart kept probing for the magic combination. “Is it ‘gates’?”

Just more smiles from the chairman.

“Do you have any pets?” (Many people unfortunately use their pet’s name as a password.) Gates said he hasn’t gotten his kids any pets yet.

“Did you ever have a pet when you were younger? What was the pet’s name?” The audience cheered Stewart’s effort to hack in to Microsoft.

“That’s not my password,” Gates said with a laugh.

The Sensitive Topic

The subject was unavoidable, and it finally came up.

“We can be frank here,” Stewart said, noting that security is a key issue for the company’s software, and that the effort to hack Microsoft products is never-ending. “Some Danish 13-year-old is working on some crazy worm that says ‘Jessica Simpson wants to go out with you’ – click – and it’s World War VIII!”

Asked Stewart: “Do you hire people who can outsmart the worm people?”

“Yeah, 14-year-olds,” said Gates, laughing. Seriously, Gates explained the new Web filters in Vista, stressing the parental controls.

Stewart addressed the camera: “Good bye, porn!”

TV on Your Computer

The conversation moved beyond Vista, to the future of technology in general.

Stewart wondered, “When are we going to get jet packs?”

While jet packs aren’t on the drawing board, Gates said, he mentioned Microsoft initiatives in robots and TV over the Internet.

Stewart asked if the recent history of technology has enfolded as Gates had dreamed it would.

The Microsoft chairman reminisced about his teenage years with Paul Allen, and how they had envisioned future machines as incredibly powerful and interactive tools. “So there’s still a few things left to be done that were part of that original vision.”

Computer technology has not yet fulfilled even half of its potential, Gates said, in terms of learning and productivity. Even TV will be revolutionized, he said, as it moves to the Internet.

The degree to which he emphasized that future TV viewers will be able to mold content to their own interests suggests this will be a major Microsoft initiative. For example, he said, viewers will be able to shape Olympics coverage just as they see sit.

Asked Stewart: “Could I make somebody fall?”

Gates: “We’ll work on that.”

Man on a Mission

Wrapping things up, Gates noted that he’d be in Europe for a few days promoting Vista, then, “I get to go back home.”

Stewart thanked Gates for coming on, then something odd happened. As Stewart was leading applause for the Microsoft chairman, Gates stood up, smiled, waved, and walked off the set.

Typically, of course, guests wait for the commercial break. Not Gates.

“He’s leaving!” Stewart mock complained. “He can’t just leave like that!”

But the chairman was gone. Years ago he left Harvard, dropping out because he was too busy fulfilling his own dream to wait around for a Harvard degree. Now he wasn’t going to wait around for the commercial break, no matter how awkward it looked.

He’s still a man in a hurry, a man on a mission. That mission will be harder in the years ahead, so there’s no time to waste. The Microsoft chairman won’t be sitting passively as the future arrives.