October: The Monk and The Riddle: The Art of Creating a Life While Making a Living

by Randy Komisar

Book Description

“What would you be willing to do for the rest of your life…? It’s a question most of us consider only hypothetically-opting instead to “do what we have to do” to earn a living. But in the critically acclaimed bestseller “The Monk and the Riddle”, entrepreneurial sage Randy Komisar asks us to answer it for real. The book’s timeless advice – to make work pay not just in cash, but in experience, satisfaction, and joy – will be embraced by anyone who wants success to come not just from what they do, but from who they are.At once a fictional tale of Komisar’s encounters with a would-be entrepreneur and a personal account of how Komisar found meaning not in work’s rewards but in work itself, the book illustrates what’s wrong with the mainstream thinking that we should sacrifice our lives to make a living.”

Discussion Questions

Book Club Review

Thanks for being a part of the Modern Leadership Monthly Book Club. If you happened upon this page and are not a member you can join for free here .

The book club is designed to explore books that will help us on our leadership journey. It is a part of the Modern Leadership Podcast where we breakdown a book weekly in each episode. You can catch the podcast here.

This month’s book is: The Monk and the Riddle: The Art of Creating a Life While Making a Living by Randy Komisar

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Brief Summary

This brief quote from the book jacket sums up nicely what to expect in this book, “A disarming … book that injects some welcome spirit into a stiff genre.” Starting in Randy’s “office, the coffee shop in Silicon Valley, where for years some of the biggest deals have been negotiated, we are introduced to Lenny and his “big idea” Funerals.com. The book walks through the decision making process of one venture capitalist, Randy Komisar, as he advises Lenny through gaining funding. Spoiler alert: the book is not the nuts and bolts of getting a new venture funded, but rather the mental state a founder must have to be successful in building a business worth funding.

About the author – Randy Komisar

Randy Komisar is a Venture Capitalist out of Silicon Valley, at Kliener Perkins Caufield Byers (KPCB.com), located right on historic Sandhill Road. The heart and soul of tech investing. He is the former CEO of LucasArts Entertainment and Crystal Dynamics, and acted as “virtual CEO” for WebTV and GlobalGiving. He served as CFO of GO Corp. and senior counsel at Apple Computer, following a private practice in technology law. He is a Founding director of TIVO and a graduate of Harvard law school.

Randy lives in Portola Valley, California, with his wife, Debra Dunn, and Tika and Tali, the Horrible Hounds. He currently incubates startups as a Virtual CEO, helping to build businesses from vision and ideas.

You should read this book if:

  • You love an unconventional approach to business and being funded
  • You enjoy the teachings of Buddhism
  • You want to know the “mindset” behind successful start-up founders
  • You are interest in Old Bagan, Myanar
  • You want to know how to drop an egg three feet without breaking it

Who shouldn’t read this book

  • This book is not for you if you want a list of steps to take to be VC funded
  • You like a serious book with no hypotheticals
  • You want straight to the point writing with no tangents for coffee refills
  • You think “start-up” is what happens when you turn the key in your car

What surprised me

This book came highly (highly) recommended. With a different style title, I am not sure what I expected. I knew Randy’s history (bio) and his impact with KPCB and Nest, but I knew nothing about his style or personality. The book starts with Randy on a motorcycle in Myanmar with a stranger monk riding behind him. I loved this book from the moment I read the first word to the end when I discovered the answer to the riddle (egg… 3 feet). I was surprised at how conversational the book was. He entered my mind and answered the questions I (Lenny) had and addressed the fears we all face. I guess my surprise is how much the book spoke to me…directly.


None- I drank the Kool-aid. I loved the book, enjoyed talking with Randy on the podcast, and highly encourage a reading of this book.


  • we do not need to sacrifice our lives to make a living.
  • I focused on a critical weak link in the chain: the human side, the entrepreneurs and their motivations. While investors, analysts, and entrepreneurs were mesmerized by the brilliant horizons of the New Economy, I questioned whether the rickety ships we had launched with their inexperienced captains could ever get there. While the market momentum seemed inexhaustible, I wondered if beyond greed there was enough passion to fortify the startup crews when the seas got rough—and they always do.
  • No matter how hard we work or how smart we are, our financial success is ultimately dependent on circumstances outside our control.
  • Marrying our values and passions to the energy we invest in work, it suggests, increases the significance of each moment.
  • Rather than working to the exclusion of everything else in order to flood our bank accounts in the hope that we can eventually buy back what we have missed along the way, we need to live life fully now with a sense of its fragility. If
  • The Monk encourages us to make work pay, not just in cash, but in experience, satisfaction, and joy.
  • Success, even on your own terms, entails sacrifice and periods of very hard work.
  • finding meaning and fulfillment in one’s work should not be an elitist notion.
  • The Monk is not primarily a business book; that is, it is not about buying low and selling high, but rather about creating a life while making a living.
  • The Monk is not about how, but about why.
  • “Imagine I have an egg” —Mr. Wizdom cups an imaginary egg in his hand—“and I want to drop this egg three feet without breaking it. How do I do that?”
  • I see a common gene among immigrants and entrepreneurs who strike out from the pack to pursue their dreams.
  • I admire people who are willing to bet everything on a belief.
  • in my own history I’ve been helped by people who should have given me the boot for my naïve and disruptive zealotry.
  • “Lenny, why is this a big idea?” “It’s a big market, big dollars.” “Will it change the way the world operates? Will it change people’s lives in any meaningful way?”
  • Startups are unique animals. We take them pretty much for granted out here now, but they are still endeavors that require very different skills from the ones needed in established companies.
  • VCs invest first and foremost, I explained, in people. The team would have to be intelligent and tireless.
  • Anyone can sail with the wind to his back. Startups usually sail into a stiff wind, leaking like a sieve, in high seas, without food or water.
  • I explained to Lenny what I do: I incubate startups. To that end, I provide the scarcest commodity of all, leadership and experience.
  • I invest my time, and, in return, I receive an equity stake in the business.
  • I can be very outspoken, if I fear that we don’t have room for a misstep. But the CEO is in charge; I’m there to make him or her successful.
  • Ultimately being right, or better positioned, may be more important than being first.
  • You have to be able to survive mistakes in order to learn, and you have to learn in order to create sustainable success.
  • It comes down to my realization over the years that business isn’t primarily a financial institution. It’s a creative institution. Like painting and sculpting, business can be a venue for personal expression and artistry, at its heart more like a canvas than a spreadsheet.
  • Why? Because business is about change. Nothing stands still. Markets change, products evolve, competitors move into the neighborhood, employees come and go.
  • variously involved in the Valley as founders, funders, or functionaries—
  • “Deferred Life Plan.”
  • Step one: Do what you have to do. Then, eventually— Step two: Do what you want to do.
  • When I graduated from Brown in the mid-seventies,
  • didn’t seem to fit anybody’s profile. It was troublesome to me that I couldn’t find a match; I had expected to settle into a career like everyone else.
  • The “serious” life I chose was the law. In the fall of 1978 I trudged off to Harvard Law School
  • I never doubted Lenny’s drive. It was obvious from the very beginning, even in the armlock he laid on me at the door of the Konditorei. Drive, commitment—those weren’t my concern. I wanted to know what he really cared about. I wanted to know his passion. Lenny didn’t seem to understand the question. He was beginning to nettle me.
  • In the first step we earn, financially and psychologically, the second step. Don’t misunderstand my skepticism. Sacrifice and compromise are integral parts of any life, even a life well lived. But why not do hard work because it is meaningful, not simply to get it over with in order to move on to the next thing?
  • The distinction between drive and passion is crucial. I had asked Lenny about his passion. He thought I was questioning his drive and commitment. Passion and drive are not the same at all.
  • Passion pulls you toward something you cannot resist. Drive pushes you toward something you feel compelled or obligated to do.
  • If you know nothing about yourself, you can’t tell the difference.
  • I felt I had done the unforgivable. I had bailed out of a plane that was still in midair.
  • Without a grander vision, and some prospect of realizing it, Crystal was not a place I could see myself working the rest of my life. That meant I needed to get out, now.
  • As I tell the M.B.A. classes I sometimes address, it’s the romance, not the finance that makes business worth pursuing.
  • Entrepreneurs, in my experience, don’t like to be told they’re wrong.
  • The chance to work on a big idea is a powerful reason for people to be passionate and committed. The big idea is the glue that connects with their passion and binds them to the mission of an organization. For people to be great, to accomplish the impossible, they need inspiration more than financial incentive.
  • Impatience wasn’t Allison’s problem. Finding something in Funerals.com to care about was.
  • Business conditions are forever changing. You need to reconsider your strategies and business models constantly and adjust them where necessary. But the big idea that your company pursues is the touchstone for these refinements.
  • Sometimes a team never even proceeds beyond the first slide, as the inquisitors hurl unanswerable or painfully sensitive questions that cut through dreams with surgical precision.
  • Sure, business was about money. That’s what makes it business. But first and foremost, to be successful, business is about people. It took me a while to learn that lesson.
  • My job was to find intersections of interest between the negotiating parties—not differences, but commonalities—and to build them into a solid relationship and transaction.
  • BUSINESS, I told Lenny and Allison, is about nothing if not people.
  • I found that the art wasn’t in getting the numbers to foot, or figuring out a clever way to move something down the assembly line. It was in getting somebody else to do that and to do it better than I could ever do; in encouraging people to exceed their own expectations; in inspiring people to be great; and in getting them to do it all together, in harmony. That was the high art.
  • Lenny was going to have to answer those fundamental questions he had so neatly avoided thus far. Why was he doing this? What was important to him, and what did he care about? Who was he, and how could he express that in his business?
  • Everything in this Valley turns on risk. Lenny had been hedging, unwilling to expose the big idea, because he suspected it had a substantial chance of failing as a business. Cheaper caskets seemed straightforward as a moneymaker, and he wouldn’t have to stretch hard to try it.
  • The question he seemed to have answered was not, How can I make a difference? but, What’s the least risky path to financial success?
  • Ironically, he had assumed the biggest risk of all in Silicon Valley, the risk of mediocrity. He had dug his own grave.
  • Silicon Valley does not punish business failure. It punishes stupidity, laziness, and dishonesty. Failure is inevitable if you are trying to invent the future.
  • Riding the highs and lows long enough, never being able to see beyond the next peak or the next valley, makes one realize there is only one element in life under our control—our own excellence.
  • Work hard, work passionately, but apply your most precious asset—time—to what is most meaningful to you.
  • “If we do our best and it fails, we’ll still be glad we did it. It’s worth doing.”
  • WHEN ALL IS SAID AND DONE, the journey is the reward. There is nothing else.
  • Reaching the end is, well, the end.
  • If the egg must fall three feet without a crack, simply extend the trip to four.

My Key Key Key Takeaway

  • My key: I [Randy] invest my time, and, in return, I receive an equity stake in the business.

We read a lot about venture money and the boost that it can give you in your business. We watch Shark Tank and see the Sharks teach start-up founders the reality behind business. This book is not about venture funding. This is a book about having the right mindset to make your business successful. And that, is the key to many questions you have about start-up success

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Podcaster | Speaker | Leadership Mentor

Jake Carlson is a popular speaker, accountability partner, and host of the Modern Leadership podcast. Jake built his business while traveling with his family around the world. Follow him on Facebook, Twitter, Instagram or LinkedIn. Read more about him here.