The miserable millionaires
Entrepreneur Christine Comaford-Lynch (above, in an old Fortune photo) has gone from Valley millionaire to bestselling author with her memoir-slash-business book, Rules for Renegades. But making a million or two in stock options could be the worst thing that ever happens to you. Why?
Because if you're rich, you don't have to work hard. So you probably don't, so you accomplish nothing, so no one in the Valley cares about you.
Comaford-Lynch is different: She became a moderately wealthy VC because she figured out how to succeed at running a tech business. She's made over $10 million so far.
But she's a rarity, because she really did have a crazy, interesting path to that ten mil that makes a good book: Runaway teen, model, Buddhist monk, teenage female software developer at the early Microsoft, dated Bill Gates, studied to be a geisha, started her own company on the spot one day as a fuck-you to Microsoft HR, created a successful IT services company, was a PC Week columnist back when that mattered. Christine learned a lot worth passing on. She didn't make her money from Microsoft stock — she made it by building and selling her own companies.
Even so, selling the book was tough. She attended writing classes and spent months earnestly editing. What did she get? 22 rejections from publishers. Because no one wants to read about some non-celebrity's life, no matter how wacky it is. Finally one market-savvy editor said look, why don't you rewrite this into a business how-to book on how you made $10 million in tech without college? Result: Rules for Renegades, which hit #3 on the New York Times list. Since writing the book, she's racked up another million through, in her words, "teleseminars, speaking gigs, a few startups I work with getting acquired, selling products from the stage and online, and book royalties :)." I got tired just pasting that in.
Too many Valley millionaires have no good stories to tell, and no firsthand advice on getting rich other than "Get hired at Google in 2002." That doesn't qualify you to be a VC, or to start your own company, or hahaha to make it as a model. It makes you what Burn Rate author Michael Wolff dubbed "the walking dead" — rich guys no one wants to talk to. And if you'll pardon my snobbery: Suddenly having a lot of free time and a new laptop doesn't make you a writer. Are boring, self-aggrandizing Googler memoirs now circulating among book agents and publishers? Tragically, yes.