In 1988, John Rothchild penned what might be the only legitimately funny finance book ever written: A Fool and His Money.

I’ve easily read more than 300 finance books, and despite enjoying many of them, none of them made me laugh.

Until I read this one.

The author went on an odyssey to invest his own money.  Speaking to investment professionals (and detailing the hilariousness of those conversations) he put his own money on the line in the name of self-sacrificing journalism.

He ventured out to interview brokers and investment advisors.  And he gave many of them his own money to invest.

The stories he tells—especially if you read them slowly, and carefully—will have you laughing out loud:

“I happened to see an article about psychics and astrologers who give investment advice….  Mostly out of curiosity, I decided to contact at least one psychic…I had called Ms. Jayson-Koerber, intending to set up an appointment, but something about our conversation made me change my mind.  It may have been the dogs barking in the background, or it may have been her telling me that she was terrific at finding bodies for police departments.”

That might sound like a stretch, to call on a psychic for investment advice, but most of the book’s funniest parts dealt with advice from real brokers and advisors.

Rothchild is a great writer.  And his book should be savoured for the literary masterpiece it is.  He pokes fun at the industry, but remains in character: showing the careful reader how ridiculous it all is, while maintaining an honest open-mindedness (some would say purposeful naiveté) which makes it even funnier.

How about a sequel?

At some point, I think somebody should try the same thing with their own personal money and write a sequel.   Interview advisors, write about what they say, select a handful of advisors to handle $10,000 of your own hard-earned money, and write about the feedback they give you when you ask for a quarterly report on your investments, and on the economy in general.

These could be the rules:

1.  At the possible expense of alienating a friend, you’d have to pick an advisor/broker that somebody recommended.

2.  You’d have to put your own money on the line

3.  You’d need to keep it going for at least eight years, while tracking results with a benchmark of stock and bond index funds

4.  And you’d have to pick one of those astrologer advisors that Rothchild himself wouldn’t dare.  (You might not know it, but you do know someone who’s into this kind of thing—source them out and fulfil criteria #1 and #4)

Then write your book.

I’d buy a copy.

Anyone interested in writing it?