I just finished reading Oren Klaff's book Pitch Anything (2011) McGraw Hill.

I would rate it as a very entertaining read, filled with lots of humor, anecdotes and examples of his pitching techniques in action, and a window into the world of pitching big deals worth many millions of dollars and, in one case, a billion dollar deal (to be the company in charge of raising 1 billion for a new Airport complex in California).

I thought the book would focus on the narrative elements of a good pitch but instead the book focuses more on the psychology of the 20 minute pitch in front of 2 to 3 investors. It provides a useful inventory of terminology and concepts to characterize all of the psychological elements that come into play during an in-person pitch and how to mobilize them towards a successful deal.

The 20 minute time limit is what Oren feels is the appropriate amount of time to give yourself to pitch a deal in person to an investor. Anymore and you start to lose the attention of the investor which is the main thing you are wanting to manage during the pitch. Investors can start to lose their attention after the first 3 minutes if they are not getting any novelty from the pitch, and even with novelty and a barrage of tricks and maneuverings to maintain attention on the deal, investor's interest will likely start to wane after 20 minutes. That is a good time to end the pitch and deal with potential questions.

In several places in the book, Oren stesses that a major deal killer is neediness, or "validation-seeking behavior". Oren went through a bad stretch where he was unable to make a deal with several VC's he presented to and his company was running out of money. He had successfully pitched large deals in the past, but now something was different. He talked with a mentor about he last few presentations and eventually his mentor pointed out the flaw. In his last presentation, after he gave what he thought was a great pitch, he said things like "Do you still think it's a good deal?", "So, what do you think?", and "We can sign a deal right away if you want us to?". These comments turned investor excitement over the deal into fear and anxiety. The proper frame of mind to pitch in, according to Oren, is to "want nothing" so that you do not come off as needy. The other adjustments are to focus on "prizing" - presenting the deal as a prize that the investor might not get in on if they don't act. Prizing a deal is not simple to pull off and involves many psychological elements, some of which Oren discusses in this YouTube video:

Oren argues that prizing works because of three fundamental behaviors of human beings (p. 64):

1. We chase that which moves away from us.
2. We want what we cannot have.
3. We only place value on things what are difficult to obtain.

So if you are too eager to make a deal, or it is too easy to get what you have, then investors may not value what you have. Behaving in this way, means that you are failing to prize your deal.

Prizing is only one of the psychological techniques Oren discusses in his book, but this should give you a flavor of some of the unique psychology that potentially goes into successful pitching and deal making.

In my next blog, I want to focus more on Oren's discussion of the narrative elements to include in a good pitch.