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The Monk and the Riddle: The Education of a Silicon Valley Entrepreneur

I’m going to go out on a limb and predict that The Monk and the Riddle will become the best-selling business book of the year. It will end up on the bookshelves of anyone who has considered leaving a comfortable job to start or join a startup. It could even become one of those slender classics, like Silent Spring and Small Is Beautiful, whose moral impact is in reverse proportion to its length.

Randy Komisar’s business card reads “Virtual CEO,” but he describes himself more as a consigliere to the inventors and entrepreneurs of Silicon Valley. An attorney who worked at Apple in its glory days, then led companies such as Claris, Go and LucasArts, Komisar now spends his afternoons advising startup executives. He spends his mornings in a Portola Valley caf, listening to pitches from eager MBAs with the latest schemes for e-commerce. His instincts often determine whether the candidates fly or flop with the venture capital firms on Sand Hill Road in nearby Palo Alto.

Apparently, a morning came when Komisar had heard one too many proposals for a soulless, better-faster-cheaper e-tailing site. “Lenny,” his fictional amalgamation of go-getters, comes to Komisar with a proposal to start “,” intended to undercut local mortuaries by selling cheap caskets online.Komisar tries to explain to Lenny that VCs aren’t likely to fund him unless he seems truly passionate about the idea. Komisar calls Lenny’s strategy the “Deferred Life Plan”-do something dull and predictable now, promising yourself you’ll follow your passion later. It’s only when Lenny’s partner reveals their original vision-an online community for grieving families-that Komisar sees a spark. Lenny hadn’t put this into his plan because he couldn’t see how to profit from it. But far worse than failing to make money,Komisar argues,would be failing to follow one’s dreams.

It may sound sappy, but Komisar bolsters his message by relating how he learned the lesson himself, beginning with his decision to join Apple. “When I considered the risk of staying at my law firm, I had to face the possibility of an unfulfilled life, of working endlessly on things that did not matter,” Komisar writes. “To me these were graver risks than whether Apple succeeded or failed.” Fictional Lenny eventually grasps Komisar’s point: the Deferred Life Plan is more expensive than it looks. If they can tear themselves away from their stock options and IPOs for a moment and read The Monk and the Riddle, a lot of real Silicon Valley entrepreneurs might learn the same thing.

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