You're assuming it's a big mystery why no one wanted his book proposal or that the agent hadn't previously covered this ground, neither of which is stated in the post. (Plus, this is an author who admits he's lied about his contract numbers in the past.) From my read the facts are damning enough:
* He'd gotten a big advance on his previous book but it didn't sell. (Money loser = big red flag #1)
* His reputation alone no longer sells a book idea (evidenced by the sudden need for him to write a proposal to sell a book.) (Warning flag.)
* His financial judgment is suspect. ("The Forever Portfolio" delivered to the publisher just as the market starts a giant slide.) (Warning flag.)
* His last book was, well... Here's a sentence from the first Amazon review: "That said, the book is horribly written -- the author has about 20 pages of interesting content interspersed with 200 pages of random digressions, about his love of computer games and the longest words in the English language." (At the very least, a warning flag.)
* His proposal read like it was cribbed from Wikipedia (Big red flag #2.)
* He's a real peach to work with, insisting he knows other people's jobs better than they do (after all, he claims he chose the $20 price point for the previous loser, and we know how he treats his agent). (Warning flag.)
Now look what happens when that book idea (not the proposal) finally sells -- the publisher insists on bringing in another, trusted writer as co-author.
Sorry, but I don't think there's a mystery here that the agent needs to solve.
On the other hand, the author explicitly said to his agent "Find out why she rejected it," speaking of Hollis. That suggests the author, at least, did not know why.
Perhaps. Or perhaps the agent had already told him obliquely and the author didn't want to hear it.
We know from the story that the agent had previously done his job -- selling the author's books for increasing amounts of money despite declining sales. And we know from the story that after he meets with Hollis and is told the proposal reads like a crib from Wikipedia, he goes home and writes another proposal for her. And what happens? She likes the ideas but not the writing. And when the WSJ steps in, again it's for the ideas -- they want a co-author for the writing part.
Perhaps the agent should have been more direct, "Jim, the word on the street is that you're a one-hit wonder; that your ideas are great, but your writing sucks. What do you say I check around and see if I can hook you up with a co-author for the next proposal?"
Put this in HN terms, if people like your ideas but aren't willing to fund your startup, do you think it's someone else's job to find out why?
Frankly, what I found most alienating about the story was the me-me-me focus. (I mean really, going unsolicited into stores and signing books with random messages?) Too bad there was so little focus on providing value for his readers. Once I hear an author refer to a book of his as "garbage", I'm inclined to agree with him and dump him from my recommended list.
* He'd gotten a big advance on his previous book but it didn't sell. (Money loser = big red flag #1)
* His reputation alone no longer sells a book idea (evidenced by the sudden need for him to write a proposal to sell a book.) (Warning flag.)
* His financial judgment is suspect. ("The Forever Portfolio" delivered to the publisher just as the market starts a giant slide.) (Warning flag.)
* His last book was, well... Here's a sentence from the first Amazon review: "That said, the book is horribly written -- the author has about 20 pages of interesting content interspersed with 200 pages of random digressions, about his love of computer games and the longest words in the English language." (At the very least, a warning flag.)
* His proposal read like it was cribbed from Wikipedia (Big red flag #2.)
* He's a real peach to work with, insisting he knows other people's jobs better than they do (after all, he claims he chose the $20 price point for the previous loser, and we know how he treats his agent). (Warning flag.)
Now look what happens when that book idea (not the proposal) finally sells -- the publisher insists on bringing in another, trusted writer as co-author.
Sorry, but I don't think there's a mystery here that the agent needs to solve.