Book Review – Monk and the Riddle

28 09 2007

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

The Monk and the Riddle is a lively and humorous narrative about the education of a unique Silicon Valley insider. Currently a virtual CEO who provides leadership on-demand to several renowned companies, Komisar’s unique role was recently described as a combined professional mentor, minister without portfolio, in-your-face investor, troubleshooter, and door opener. But even more interesting than what he does is how and why he does it. Komisar has found a way to turn an ambitious and challenging worklife into his life’s work. The book is at once a portal into the inner workings of Silicon Valley–from how startups get launched, to how venture capitalists do their deals, to how head-hunters make their matches–and a deeply personal account of how one mover and shaker found a payoff bigger than money. The Monk and the Riddle imparts valuable lessons about the differences between leadership and management, passion and commitment, and the meaning of professional and personal success. When all is said and done the journey is the reward.

“How can we make business inspiring?” “What is the day-to-day life of a virtual CEO like?” “What would an insider say about the Valley’s VC world?” “What’s the difference between drive and passion?” “How can we live a meaningful life?” “How can I drop an egg 3 feet without breaking it?”

“The Monk and the Riddle,” is a very rich work mixing an enlightening perspective on business, inspiring pieces of wisdom about business and life, and a compelling story. Here are some highlights.

Komisar’s business experiences force respect. He exercised law at Apple, operated LucasArts (the gaming division of George Lucas’s empire) as CEO, lea TiVo as Virtual CEO and co-founded Claris Corporation. He knows what he’s talking about, his perspective on his life’s experience is invaluable. To him, business is the only community left where one can lead a meaningful life.


The book is well written. “The Monk,” could have been the standard boring biography of your usual exceptional business guy, more interested in giving a last polish to his ego than in communicating his experience in a compelling way. But he mixes different streams of narration, including Komisar’s memories, provocative kernels of wisdom, and the difficult funding race of a young start-up.


One of the concepts in the book is “the deferred life plan.” Namely, we settle for the things we have to do first (earning money, climbing the professional and social ladders), so that we are then free to do the things we really care about. The problem is that under this strategy, we often lose what we were trying to reach in the first place.


We adopt the deferred life plan, because we usually mistake drive for passion. Drive pushes you, but passion pulls you. Drive is from the outside in, but passion is from the inside out. If you don’t know yourself, it is very easy to confuse the two. You relegate your passion to the second part of your life while driving yourself to achieve external imperatives that fit your perception of what your social environment expects from you. Drive, followed by passion, is the recipe for the deferred life plan.

But if you don’t pursue your passion now, when will you? And why use today to achieve goals you don’t really care about?

Prospective entrepreneurs may think they know everything there is to know about starting a business in Silicon Valley. They can draw up business plans, have meetings with venture capitalists, maybe even get funded and actually launch a start-up. However, in The Monk and the Riddle, Randy Komisar reasons that’s only half the equation for success. And it may not be the important half. Komisar has worked with a number of companies —and has come to a rather startling conclusion: if you can’t see yourself doing this business for the rest of your life, don’t start it. In other words, he wants to see passion and purpose in business, not just spreadsheets and a by-the-numbers business model.

To illustrate, Komisar takes the reader through a hypothetical Silicon Valley start-up, with an eager entrepreneur named Lenny trying to get funding for an online casket-selling business. As Komisar helps Lenny find the real purpose of the business, the passion behind the revenue projections, he reflects back on his life as an entrepreneur. Komisar emerges as a master storyteller, the kind of guy you’d feel honored to share a bottle of wine with. And you believe his conclusion: “When all is said and done, the journey is the reward.” It’s great if you’ve made billions on the journey, but the important thing is that you do something you can truly throw yourself into.




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