Using Spammer Techniques for Good in your Investor Pitch
Why are spam emails horribly misspelled and in general terribly written? Surely they want to be taken seriously by their readers. It's not an accident, and it's not that they can't write any better. They are consciously filtering for people who are good targets for the next steps of their scams. If you're turned off by bad grammar and writing, you'd definitely be turned off by what will come next anyway, but you will have wasted some of their time in the process. So better cut you off at the top of the funnel. Microsoft Research actually wrote a great paper on the subject.
How does this apply to an investor pitch you ask? As an entrepreneur pitching a venture, you are often pressured to present your startup in the broadest, most attractive, most polished terms. This can be of use when it reflects reality on the ground, but the counterintuitive advice we gain from the spammers is that flaws, or even just quirky/idiomatic elements are worth exposing in a pitch and deck. If the investors would care about them, they will find out and drop out anyway. If they continue talking to you, you have a much more qualified pipeline that understands the implications, and discussions are much more likely to come to fruition.
But you also save yourself from a more insidious failure mode. If you are unclear about your roadmap, your philosophy, or your plans to develop the business, and encourage an investor to believe what they want to believe, you have just signed up for a lot of pain at the first sign of trouble or earlier. If the investor believes that the technology is "almost there" or that users are signing up in droves when they're not, then you may get their money, but perhaps you'd rather take the money of someone who believes in the vision. If they signed up for a social enterprise and you intend to maximise for profit, there is bound to be hurt feelings and mistrust, justified even. This is the counterintuitive advice against over-optimising your deck and pitch.
This actually applies to any "sale" whatsoever, from hiring, to partnerships, to finding a romantic partner. Going too far in the other person's direction during the sale is likely to cost you farther down the line. Better make your true self apparent early on and save yourself a bad match. You may spend a little more time searching, but that search will pay off much more handsomely.
So there you have it. The importance of being honest, in game theoretic terms, as demonstrated by spammers.