Monogamy: Risky Business

I have done a lot of startups. Many early stage venture capitalists believe that once they fund a startup, the probability of long term survival is in the neighborhood of 10% and 20%. Tough neighborhood.

Of course that's just the ones these guys fund. And given that venture capitalists are relatively risk adverse (I have only done one venture-funded company, three if you count ones where the VCs pile on AFTER success is obvious), the real odds are certainly worse.

But let me tell you, although I have experienced hundreds of naysayers and critics to every one of my crazy startup ideas over the past many years, I have never seen as much skepticism, smirking disbelief and sheer incredulity as has greeted my latest project: monogamy. Even the most aggressive VCs and private equity people I know are skeptical.

It is almost disheartening. If it were not so motivating!

Fortunately most of these naysayers tell me that they disbelief the concept, not the person implementing it. I suppose I should feel a little better about that. At least they are not saying that they feel I am uniquely unqualified for monogamy. Still, it is commonly mentioned that the bane of monogamy is alternative opportunities, and such opportunities are very easily available to me due to my lifestyle and travel. Perhaps not as much as to a media star, but still…

One interesting side effect of declaring monogamy is that it has effectively flushed out a lot of historical, um, quarry. There are a surprising number of married or otherwise paired women – women who I could have never guessed had an iota of interest in me – who have suddenly told me that they were interested in me in the past. Gee, thanks. Now that I have sworn to monogamy, it is like there is an open license to tempt.

So the pool of temptation is enlarged. This expanded dataset has enabled some new observations. For example, many female acquaintances now seem to fall into one of three categories:

First, there are those who are happy that any man is trying to be monogamous. I call these the Wishful Thinkers. They want to believe in a world where a man can be monogamous, but in general they tend not to feel that it is common. So they are kind of rooting for me, I think, and yet they are not really rooting for ME but rather a concept. They are the romantic antithesis to the private equity naysayers I noted above. The most skeptical subset of these women, perhaps unsurprisingly, comprises former or current sex workers. They are constantly exposed to men who stray, so this seems natural. They either have a healthy and open attitude toward sex, or a resigned attitude. The most romantic of these women wish me well, but seem very skeptical. These are the Wishful Skeptics. Thank goodness that they are not the population that tries to tempt me to stray!

Next, there are the women who feel that it is their mission in life to ensure that no man who makes such a foolish declaration shall survive to make it so. Some of these women are bitter. Others have more complex motivations that I fear to unravel. These are the Zero Sum Gamers.

Lastly, there are women who now see me as a safe friend, being “taken,” and have opened up to shocking confidences. Sometimes it is with Jenny that they open up in this way, to her great discomfort. These are the Little Sisters.

Of course there are other behaviors, but these are the three (and a half) interesting ones because they are all predatory in some way, however slight.

I expect they will be a threat factor in my monogamy quest, something to keep an eye upon, and therefore areas to proactively develop some defenses.