What to Expect from Steve vs. Bill (And Who Will Win?)

It seems ridiculous to compare tech moguls to pro wrestlers and prize fighters, but I can't stop.

In my mind, tomorrow's Bill Gates vs Steve Jobs is the tag tech team matchup of the century. For geeks, it's like Hulk Hogan vs Macho Man, or Ali vs Frazier. But, hmmm.....the WSJ is in the ring, so does that make it Bill Gates and Steve Jobs vs Mossberg and Swisher? No one knows, and that's the beauty of the royal rumble format, first pioneered by the World Wrestling Federation. The time, Wednesday, May 30th at 7:15pm. The Venue: The Octogon-of-tech, All Things D. Which makes Mossberg the new Don King.

Turning the debate into a deathmatch also begs the interesting but extremely immature question that no one is asking. Who is going to win? And by what metrics?

To answer, I call on the help of some friends. Wired News has a great collection of past pot shots from Bill and Steve. The Seattle PI has a piece analyzing the density of big words in past Steve and Bill keynotes. And of course, Fake Steve Jobs has his own unbiased take, entitled "Bill Gates, I am going to make you my bitch!"

From Wired, Bill on Steve's iPod:

"I don't think the success of the iPod can continue in the long term, however good Apple may be.... I think you can draw parallels here with the computer. Apple was once extremely strong with its Macintosh and graphic user interface, like with the iPod today, and then lost its position."
— Frankfurter Allgemeine, May 2005
"In terms of public relations, yes, Steve is the most successful in the industry. But he does it by saying how crummy everyone else is." — Fortune, Oct. 9, 1989

And Steve on Bill's...Everything:


"I am saddened, not by Microsoft's success — I have no problem with their success. They've earned their success, for the most part. I have a problem with the fact that they just make really third-rate products."
— Triumph of the Nerds, PBS documentary, 1996 (Ed. note: According to an Aug. 8, 1997 New York Times story, Jobs later called Gates to apologize for his comments in the film.)


"Here's something Microsoft will never be able to rip off."
— Mac World Expo, 2007, introducing the iPhone

The PI goes word geek and analyzes Keynotes from both last week. Jobs averaged 10 words per sentence, vs. 21 for Gates. Gates used nearly 2x the number of words with over three syllables. Gates was 2x as hard to understand as Jobs. Gates' favorite words of the speech were: Device, Windows, Great. Jobs' fav words were: Phone, iPhone, iPod. Jobs is easier to understand, and Gates has a bigger brain. But Gates has stage fright, often walking off stage (see: Daily Show) and Jobs has that reality distortion field going on.

And Fake Steve Jobs, well, you'll have to go read it yourself, but to paraphrase:

My old comment about "Microsoft has no taste"? I stand by what I said. Especially since Vista came out and we found it's just XP in a skirt.

No surprise here. Jobs has the popularity, but Gates has the big money. So we'll have to wait and see. And thankfully, I have front row tickets, right in the splash zone.

Jobs & Gates, the Biggest Reunion Since Simon & Garfunkel
All Things D [Gizmodo]
[Wired]
Bill Gates and Steve Jobs: Keynote text analysis [Seattle PI]

Bill Gates, I am going to make you my bitch!
[Fake Steve Jobs]