You Will Make Money in Your Sleep: The Story of Dana Giacchetto, Financial Adviser to the Stars [Hardcover]

This is not the sort of book I would typically read. I had never heard of Dana Giacchetto and could care less about his world of decadent wealth and "A-list" people. But I do know the author and her husband and some of the people mentioned in the story, so for that reason it interested me and I ended up reading the whole thing in a weekend. (It also resonated with my own family history; my grandfather was a charming, lovable sociopath who went to prison for fraud.)

One reviewer here criticizes the book for not being objective, but the author's direct personal involvement is precisely what pulled me into the story and held me there. White's first-hand experience guides the reader into a world that most of us will never know, making both the excitement and the anxiety palpable. She was at once friend and victim of her subject, and the tension between those two poles - her efforts to reconcile her positive feelings for him against her negative experience - kept me engaged. I found her ability to tell the story with both compassion and anger remarkable, the thing that takes this beyond being just another true crime exposé or scathing portrait of a greedy jerk. There is genuine feeling behind the facts, and for me this is far more compelling than (supposedly) "objective" reportage.

Another reviewer complained that the book paints a negative portrait of Medford and of Giacchetto's family. As someone outside of that community, I did not feel the town was portrayed in a particularly bad light, and in fact some of the neighborhood "fun" of suburbia in the 60s comes through. But as David Lynch has shown us, the 'burbs have their dark side and White was right to acknowledge that. She clearly cares about the family and appreciates their eccentricities without denying their problems. Some of their essentially harmless quirks - the father's grandiosity and embellishment of reality, the mother's love of gambling and deal-making, their occasional reckless spending in order to impress others - resurface in their son in a more sinister form. And I was fascinated by the good boy/bad boy contrast between the golden boy Dana and his petty criminal brother that is woven throughout the book. It's a reminder that people are far more complex and multi-layered than we realize, that outward appearances tell only a small part of their story.

It's easy to look back on such scenarios or to read about them second-hand and see all the red flags, to wonder how these otherwise intelligent people were taken in by someone so obviously not trustworthy. But real life isn't that simple. There are all kinds of factors that color our perception of any given situation or person, and plenty of delusion to go around. It takes a certain amount of guts to not only admit you were taken in, but to also make all of the gory details public, and to do so with a fair amount of sympathy and humor. I admire White's courage in telling her/Giacchetto's story without demonizing her subject or spinning it as a simplistic tale of Bad Person/Poor Victims.

I always wondered what happened when the dudes at subpop started rolling in cash after Nirvana broke. When you are so NOT ABOUT THE MONEY, and suddenly you are wallowing in it. I had no idea that the indie execs were sucked into a larger scam by a fame-obsessed scammer to the stars. Great storytelling and great stripped down prose. Keeps you from getting too nostalgic.

The story of a 90's con-man, a "financial adviser" who managed to befriend and then swindle major celebrity clients out of millions, and brokered the sale of a minority share in Sub Pop when Grunge was big.

Obviously the guy must have had a lot of unctuous charm, but it doesn't really come across in the narrative. The accounting methods of the firm he ran were evidently absurdly lax, it was an obvious ponzi scheme almost from the start. He just comes across as a venal, drug-addled, name-dropping weasel. The parts about his family and upbringing are particularly tedious. Still, the book has some value as an artifact of the 90's economic bubble.