When you talk to women your m.o. should be breadth-first search, weighted by expected value. You should always talk to women in parallel rather than serially. You can't afford the time it takes to talk to women serially, plus if you only talk to one woman at a time, they don't have the pressure of other women to make them act. But you shouldn't pay the same attention to every woman, because some are more promising prospects than others. The optimal solution is to talk to all potential women in parallel, but give higher priority to the more promising ones.
The analogy to dating is problematic. Such a strategy is indeed effective for dating, but feels mercenary or even sociopathic to most people. Making the analogy raises moral issues that aren't relevant to fundraising.
Every human interaction is just analogous to dating, because human interactions are based on interest and the whole thing is called social dynamics. Be high value and wanted and everybody wants you, be desperate and low value and nobody wants you.
In dating, it is sexual interest, in business, it is monetary interest , the underlying principles are the exact same.
Essentially, they lead you on. They seem like they're about to invest right up till the moment they say no. If they even say no. Some of the worse ones never actually do say no; they just stop replying to your emails.
I've never sought investment, but I always really disliked it when companies broke communication off after an interview or application without a firm rejection.
On the otherhand, I think I prefer diminishing communication when it comes to dating. I don't treat dating like an application process. Most of the time when I talk to a woman, I'm not trying to ascertain her suitability as a mate, rather, I'm just trying to make my day/evening a little more enjoyable by having a conversation. Sometimes those conversations turn into something else, sometimes they don't. If I text someone after getting there number, I think I'd much rather prefer no response (I get what that means) to some sort of direct rejection.
PG makes the comparison explicit later in the essay:
"There are many analogies between fundraising and dating, and this is one of the strongest. No one wants you if you seem desperate. And the best way not to seem desperate is not to be desperate. That's one reason we urge startups during YC to keep expenses low and to try to make it to ramen profitability before Demo Day. Though it sounds slightly paradoxical, if you want to raise money, the best thing you can do is get yourself to the point where you don't need to."
s/investors/women/ && s/investor/woman/
(works the other way too)
When you talk to women your m.o. should be breadth-first search, weighted by expected value. You should always talk to women in parallel rather than serially. You can't afford the time it takes to talk to women serially, plus if you only talk to one woman at a time, they don't have the pressure of other women to make them act. But you shouldn't pay the same attention to every woman, because some are more promising prospects than others. The optimal solution is to talk to all potential women in parallel, but give higher priority to the more promising ones.