I once worked on a company funded by Pierre Lamond, veteran Venture Capitalist at Sequoia Capital. During the interview, Pierre asked me, ?How old is your father? What does he do? Is he retired?? I explained, that my father (in his sixties) is an entrepreneur, and will never retire, because he still has too many things that he wants to accomplish, and that he will die trying to get through as many of them as possible, and not run out of things to try. Pierre nodded and said, ?I don't understand 50-year old executives who want to play Golf all day.?

I had another conversation with Jim Hogan of Telos Venture Partners over lunch one day on the same subject. Jim said, ?You know, when a man is successful, has made money, what he is looking for is his Legacy.?

If you look around Silicon Valley today, there are lots of executives and entrepreneurs who have been successful, made money, and are ?waiting in the sidelines? looking for the right next opportunity. VCs and Executive Recuiters recruit CEOs out of this bunch. More than ever before, there is a large population of people today in technology with prior CEO experience, many of them dreaming of something really sizeable, high-impact, game-changing and sufficiently exciting to get their juices flowing again.

The bulk of the opportunities out there, however, are, for example, a CEO job at one of 600+ Security companies, where the best exit one can hope for is becoming a feature in the larger offering of a Symantec or a McAfee. Not terribly inspiring, is it? Even though, there is a bit of money to be made, it certainly doesn't qualify as a Legacy-building opportunity. Additionally, it's fairly boring to do the Nth gig in the same narrow domain, even though the mantra in hiring is Domain Expertise. (I go out of my way, on a regular basis, to broaden the range of domains that I get to play with, and that's what keeps me engaged, challenged, interested.)

So, what's the point? The point is, you cannot blame 50-year old executives for choosing to play Golf or do Origami, over running an incremental business in a domain that they already know well, are bored by, and find positively uninspiring. Anyone who has been a CEO, knows, that trying to be one without oozing enthusiasm for the business is not sustainable. And with these little businesses, the CEO is effectively a glorified VP of Sales, another uninspiring little detail.

This is a contrarian and counter-intuitive point-of-view for VCs and Recruiters: Try to recruit experienced CEOs to your promising company by offering them opportunities to learn and grow as well, rather than just milking them for what they bring to the table based on their history. Look for people's internal fire and ability to figure things out, and be fresh and creative, without being boxed in by a 25-year history in one narrow domain.