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How one goes from loser to rock star to ''Loser''

How one goes from loser to rock star to ”Loser.” Dan Kennedy explains why he was trying to keep his new book a secret

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Dan Kennedy
Dan Kennedy: Maria Lilja

Right after Dan Kennedy finished writing Loser Goes First: My Thirty-Something Years of Dumb Luck and Minor Humiliation (Crown, $21.95) — a funny, self-immolating new memoir detailing his blazing failures as a dotcommer, a rock star, a health-club attendant, a pro bass fisherman (and the list goes on) — the 35-year-old landed an awesome job as director of creative development at Atlantic Records. We caught up with him in his fancy, high-tech midtown Manhattan office.

Dude, look at this place — you’re not a loser at all!
Here’s the deal — I have to close the door to say this. When the galleys of ”Loser” came out, I was totally trying to keep it under my hat. It felt like having a pound of weed at work. They’re just going to read this and go, ”What the f—? You tricked us into this.”

Is it sneaky to write a book about being a loser when you’re not a loser?
I don’t think you understand. The sneaky thing is holding a job like this when you’re a loser.

When did you decide to write the book?
I started doing [spoken-word] gigs about how everything I’ve tried to do for the last few years was basically f—ed up. The more gigs I did, the longer I realized that list was. I was like, ”This isn’t just about dotcom. This isn’t just about [my stint in] advertising. How far back does this go? This goes back to when I was, like, 10!”

Are you worried you’ll draw real losers on your book tour?
My girlfriend goes, ”Well, I guess you’ll be able to meet lots of groupies on the road.” I go, ”Think about the book I’m supporting, and you tell me who wants to sleep with that guy after the gig.” She’s like, ”Yeah, good point.”