Bill Gates as Fidel Castro

How is Bill Gates like Fidel Castro? And what does that mean for the future of computing and the Internet?

I’m an amateur Gates-ologist myself, given that he and I were born the same year (1955). Since we remember the same Presidents, I’m going to tell you the answers to these questions.

In the early ’80s — our mutual salad days — PCs, minicomputers, and mainframes were distinct machines. Customers and companies knew not to cross the line. I felt myself to be in a reporting backwater. Gates could clean up against kids his own age.

But even then, Gates and Microsoft were preparing for a final battle, an ultimate showdown. I knew who that showdown would be with — IBM.

Now that battle has come. Microsoft’s new ads emphasize its place as “enterprise software.” The chairman of Merck, an old-line Fortune 500 drugmaker, is the newest addition to Microsoft’s board of directors.

The Microsoft.Net initiative isn’t just about the Internet. It’s about linking all computers, including mainframes, into Microsoft’s architecture.

Most of the old IBM leaders were, frankly, mediocre company men who rose through the ranks by being good bureaucrats. But in 1993, IBM went outside itself to find a man who could truly challenge Gigadollar Bill. It hired Lou Gerstner, then chairman of RJR Nabisco, as its CEO.

Gerstner, like Gates, and like Gerstner’s celebrated predecessors Thomas Watson Sr. and Jr., had a vision for the company. He called it “network-centric computing.”

Rather than sell (or lease) hardware and software, IBM would sell results, results delivered by its people and network. The box, the software, even the data were unimportant. What mattered was the output, the productivity of the network (and thus the customer) — productivity would be IBM’s product.

Well, it worked, and Microsoft.Net is, in many ways, a copy of Gerstner’s vision, executed (as all things Microsoft are executed) through software.

But just as this final battle is about to begin, with IBM flying the flag of “open source” and Microsoft executives calling that a tool of the devil, Gates is about to be handed a great victory.

Lou Gerstner is retiring. Bill Gates has outlasted another opponent. Who knows if Gerstner’s successor will share his vision or strategy? He (or she) might be Clueless, there might even be a succession battle. That would give Gates his final victory — domination of all computing — by default.

So now you see the answer to the question I posed at the start of this piece. Gates’s big advantage in all his real (and imagined) wars with IBM has been his relative youth. Gates has outlasted generations of IBM leadership and, thus, so has Microsoft’s strategy. That’s how Gates and Castro are alike.

All of us are betting billions of dollars — the future of our companies and computing platforms — on the result of this final battle. Microsoft will become vulnerable only when it truly becomes, like IBM, an institution, when Gates has left the building and his memory no longer haunts the place.

Speaking as just one 46-year-old, that day is a long way off.