I’ve been a writer wannabe my whole life, but I’ve mostly worked on fiction and magazine articles (and blogging, of course!).

Now I’m trying to do my first book proposal for a non-fiction book.

For a work of fiction, you basically finish the whole thing and then show it to potential agents and publishers.  The theory — I guess — is that you can’t judge the book by looking at a subset of it.  You need to “experience” the whole thing.

Fair enough.  With non-fiction books, my friend Howard Yoon says, you get a kind of a break: you don’t have to do the whole book to sell it, you just do a proposal.

He showed me a couple of examples, and set me to work on a book proposal about a topic dear to my heart: Intelligent Pitching.  I’ve blogged about this some, and I’ve given lectures and classes on it some.   Now I’m putting together the book proposal.

The format Howard gave me is pretty brutal: you need about five pages of sample for each chapter that will be in the book.  Well, if a chapter is something like 20 pages, that means you have to write about a quarter of each chapter before you actually write the book.

I guess the good news here is that once you’ve written the proposal — and if the your editor/publisher resists the God-given temptation to edit your work — that you then have written a good part of the book, including its structure, the spine.

There’s more to the proposal than the sample chapters: you need to give, in essence, a marketing plan for the book and a pitch for your own bona fides as an author.  There’s other stuff as well.

The book recapitulates what I’ve learned about pitches from 12 years of doing venture capital and 5 years of consulting before that.  My big shtick is that you need to think in detail about what’s on the mind of your audience in order to craft a good pitch.

It seems like motherhood and apple pie, but it’s amazing to me how few pitches act as if their authors thought about the audience beforehand.

For example: investors don’t (especially) want to know what problem your business solves.  They want to know how good your business model is.

If you crafted a pitch with that observation in mind, you would start the pitch with the key elements of your business model.

Very few pitches start that way.  Most start with long, drawn-out dramatizations of how extreme the problem is that their business solves, which is very tiresome to the investor who just wants to know what your business is going to do about the problem.

There’s a lot more like that in the book (or, more correctly, in the book proposal).  And what Howard counseled me to put in was not dry exposition but stories, stories that show and bring to life the principles of the Intelligent Pitch.

It’s been a lot of work to get it up to fighting weight, but very instructive.