Randy Komisar: “The Monk and the Riddle”


Randy Komisar is a legendary Venture Capitalist in Silicon Valley. His 2000 bestselling book, “The Monk and the Riddle,” is part autobiography (detailing his former lives as a business lawyer and and executive), part didactic novel (chronicling a series of exchanges between himself and a fictional entrepreneur trying to procure venture capital funding for an online casket business. Written during the venture capital “boom years,” the book is addressed to entrepreneurs (and perhaps business people of all stripes) and promises to reveal to them “the art of creating a life while making a living.” Komisar opens the book with the titular monk, who he once gave a ride to on a motorcycle. It turns out, not surprisingly, that the monk wasn’t trying to get anywhere in particular: he was just in it for the ride. This provides Komisar with the basic premise of the book: the journey is the reward. You have to make business about following your passion and not just harnessing your drive to make money. He assumes, graciously, that most business people do have something they care about, something that would be a meaningful pursuit in their lives, but then defer that (he calls this the “Deferred Life Plan”) until they have made enough money to enable such a pursuit. This is the case for Lenny, the entrepreneur seeking Komisar’s help. In a series of meetings and email exchanges, Komisar exhorts Lenny to examine himself and discover what it is about his funeral business that initially interested him instead of focusing on a practical but soulless casket e-tailing business. Interspersed with these episodes are Komisar’s reflections on his stints at various innovative companies before he became a venture capitalist. Each reminiscence contains a neat lesson learned (e.g., the difference between management and leadership, the importance of people in business, the difference between passion and drive, etc.). In the end, Lenny sees the light, and reconnects with the personal, emotional reasons he conceived of the business in the first place. Komisar’s book, then, serves several purposes: It positions him as a business guru, a Wise Man in the Zen tradition. He has gone through the process as an initiate and has come out above the fray, and is now attempting to pass his wisdom down to others (Lenny is a proxy for his readers). It is also an implicit argument for humanism in business: Komisar believes that the pursuit of massive financial payoffs are not incompatible with “helping people,” and that it’s possible (and indeed essential) to integrate passion and drive, one’s business plan and one’s life plan.

See the book at Amazon.


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