Entrepreneurial companies tend to reflect the personality of their founder, and nowhere was this more true than at Microsoft. Bill Gates was by turns very brilliant, very arrogant, a master marketer, a win-at-any-cost competitor – and so was his company. In their heyday in the 1990s, both Gates and his enterprise were forbidding and unpleasant to deal with, but that has begun to change in the last few years, and now that Gates is moving on from an active role in the company, it promises to change once again.

The two obvious but still-interesting questions that arise from Gates' unexpected announcement last week are how Microsoft will evolve without him, and how he will evolve as a philanthropist.

On the first point, there is a lot for Microsoft stakeholders to be worried about. Gates was a comparative rarity among tech execs – the entrepreneur who also proved to be a good big-company chief executive. And while successor Steve Ballmer has certainly shown himself to be a capable chief executive, and Ray Ozzie is highly regarded as a genuine technology visionary, the truth is that many tech companies have had a terrible time adjusting to the departure of the founder.

The most obvious case in point is Apple Computer, which floundered for more than a decade following the removal of Steve Jobs in 1985, only to rise again upon his return. Hewlett-Packard, the original tech-company icon, is only just now regaining its footing after an extended and tumultuous post-founder period. (David Packard even came out of retirement to fix things once, but could hardly do so again.)

At Intel, the gradual retirement of founding visionaries Gordon Moore and Andy Grove (who had more than ably filled the shoes of Bob Noyce when he died an early death) has coincided with a decided decline in the company's fortunes. Sony has never been the same since Akio Morita left the scene.

It may be that Gates was the perfect chief executive for Microsoft's early development and its monopoly era – when a ruthless willingness to press for advantage even when operating from a position of dominance proved to be an asset – and not so much for the company's current phase. Microsoft's internet efforts, after all, have been a mixed bag, and the company has nothing like the competitive position it enjoyed a decade ago; maybe a different skill-set is needed.

More likely, though, the culture and competencies of Microsoft will prove to be very much a reflection of Gates himself, and thus things could be bumpy for quite a while.

As to Gates' impact on philanthropy and the human condition, the sheer size of his foundation guarantees a prominent role. His determination to bring business discipline and good management to the philanthropic process certainly holds a lot of promise, and has already yielded some results.

Yet I can't help recalling my one sit-down interview with Gates, when I was working for the Los Angeles Times in the early 1990s. The meeting was on a Saturday, at around lunchtime, and Gates could not have been more disagreeable, contemptuously dismissing my questions about what was then a Federal Trade Commission investigation as ignorant and generally treating me as someone unworthy of his attention.

After a while, an assistant came in with lunch – for him. He proceeded to eat the Chinese food in a slightly messy fashion through the rest of our interview without offering me so much as a Coke. Sharing food is such a fundamental human thing, so cross-cultural and universal, that I thought of this action as deeply unhuman, and it influences my view of Gates to this day.

It's hard to think of a man who doesn’t know to break bread with another as a likely candidate for philanthropy. But then again, Gates did a far better job building Microsoft into a great company then anyone who knew him when he was his 20s had any right to expect. Maybe he will surprise again.

Jonathan Weber is the founder and editor in chief of NewWest.Net, a new type of regional news and information service focused on the Rocky Mountain West in the United States. He was previously the co-founder and editor in chief of the Industry Standard

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