You Will Make Money in Your Sleep: The Story of Dana Giacchetto, Financial Adviser to the Stars
by Emily White
It's a fascinating story, a '90s story, and in a small way a Seattle story. The kid of Italian immigrants in suburban Massachusetts, Dana Giacchetto grows up to use his boyish charm, his knack for numbers, and his ruthlessness to become the money manager and close friend of some of the most famous people in the world, including Leonardo DiCaprio, Alanis Morissette, and Phish. Giacchetto is the guy who convinced Warner Music to pay $20 million for a chunk of Sub Pop's assets.
Emily White, former editor of this newspaper, met Giacchetto through her husband, who used to be president of Sub Pop and happened to answer the phone when Giacchetto cold-called the Seattle label one day. The Sub Pop deal was an aboveboard success, but as Giacchetto's client list grew, so did his deceptions; he didn't manage as much money as he pretended to, he often disregarded his clients' instructions, and he kited funds from one account into another to make his clients think their investments were performing well. He was caught, convicted of fraud, and went to jail for several years.
White's disillusionment with a man she once considered a friend could be compelling, but the writing is so slapdash you can't help but wonder if she finds Giacchetto's complexities all that interesting. The thesis turns out to be that Giacchetto was kind of a creep because his prevailing interest was collecting famous friends, but a related issue—whether White thought all this would make for a successful book by virtue of all the celebrity names in it—is left unaddressed.