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

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This book describes how one Silicon Valley insider has blazed a path of professional - and personal - success playing the game by his own rules. Silicon Valley is filled with garage-to-riches stories and hot young entrepreneurs with big ideas. Yet even in this place where the exceptional is common, Randy Komisar is a breed apart. Currently a "Virtual CEO" who provides This book describes how one Silicon Valley insider has blazed a path of professional - and personal - success playing the game by his own rules. Silicon Valley is filled with garage-to-riches stories and hot young entrepreneurs with big ideas. Yet even in this place where the exceptional is common, Randy Komisar is a breed apart. Currently a "Virtual CEO" who provides "leadership on demand" for several renowned companies, Komisar was recently described by the "Washington Post" as a "combined professional mentor, minister without portfolio, in-your-face investor, trouble-shooter 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 work life into his life's work."The Monk and the Riddle" is unlike any other business book you've read. Transcending the typical "leadership book" model of lists and frameworks on how to succeed in business, "The Monk and the Riddle" is instead a lively and humorous narrative about the education of a unique Valley insider. It unfolds over the course of an ongoing dialogue between Komisar and would-be entrepreneurs, "Lenny and Allison," and 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 plans get prepared and pitched - and a deeply personal account of how one mover and shaker found fulfillment, not in work's rewards but in work itself.As the narrative follows Komisar through meetings with venture capitalists and eager entrepreneurs, and as his conversations with Lenny evolve toward a resolution, "The Monk and the Riddle" imparts invaluable lessons about the differences between leadership and management and passion and drive, and about the meaning of professional and personal success. "When all is said and done," writes Komisar, "the journey is the reward."


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This book describes how one Silicon Valley insider has blazed a path of professional - and personal - success playing the game by his own rules. Silicon Valley is filled with garage-to-riches stories and hot young entrepreneurs with big ideas. Yet even in this place where the exceptional is common, Randy Komisar is a breed apart. Currently a "Virtual CEO" who provides This book describes how one Silicon Valley insider has blazed a path of professional - and personal - success playing the game by his own rules. Silicon Valley is filled with garage-to-riches stories and hot young entrepreneurs with big ideas. Yet even in this place where the exceptional is common, Randy Komisar is a breed apart. Currently a "Virtual CEO" who provides "leadership on demand" for several renowned companies, Komisar was recently described by the "Washington Post" as a "combined professional mentor, minister without portfolio, in-your-face investor, trouble-shooter 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 work life into his life's work."The Monk and the Riddle" is unlike any other business book you've read. Transcending the typical "leadership book" model of lists and frameworks on how to succeed in business, "The Monk and the Riddle" is instead a lively and humorous narrative about the education of a unique Valley insider. It unfolds over the course of an ongoing dialogue between Komisar and would-be entrepreneurs, "Lenny and Allison," and 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 plans get prepared and pitched - and a deeply personal account of how one mover and shaker found fulfillment, not in work's rewards but in work itself.As the narrative follows Komisar through meetings with venture capitalists and eager entrepreneurs, and as his conversations with Lenny evolve toward a resolution, "The Monk and the Riddle" imparts invaluable lessons about the differences between leadership and management and passion and drive, and about the meaning of professional and personal success. "When all is said and done," writes Komisar, "the journey is the reward."

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

  1. 5 out of 5

    Jessie Young

    What I enjoyed most about this book is that its point is simple, yet important: people succeed in Silicon Valley / Tech because they are committed to a goal above and beyond making money. I work in the tech industry and we're always hearing about people we know or loosely know making big money by having their companies acquired. But I always ask myself: is that really the end goal? Would you really have sacrificed all of those nights, weekends, blood, sweat, tears, relationships to this company What I enjoyed most about this book is that its point is simple, yet important: people succeed in Silicon Valley / Tech because they are committed to a goal above and beyond making money. I work in the tech industry and we're always hearing about people we know or loosely know making big money by having their companies acquired. But I always ask myself: is that really the end goal? Would you really have sacrificed all of those nights, weekends, blood, sweat, tears, relationships to this company if you thought it would end in a large check and a few years at whatever monolith purchased your little baby? I think that, for the most part at least, the answer is no. The most successful entrepreneurs are truly committed to a future vision/product/idea that is much much larger than making a few million dollars. That money is real but so few people make it to that point that they need to have a larger motivation to even get started with a company in the first place. Randy Komisar's thesis seems to be that there are various metrics to know if a business might succeed, but ultimately it is the people behind the business that make it a success or not. And those people are qualified based on their "passion" for the business, not their degrees etc. As an extension of this point, you can make the larger argument that having a "deferred life plan", as Komisar puts it, is crazy. People who go into something they don't love but hope will make them money do it for a real reason: they want to do something else later. I've never understood the types of people who live year after year in a miserable job just to make money and do something cool later. Komisar's point about not putting life off was relatively obvious, but I think it's one more of us need to hear. Another note on the book is that it was written in 2000 but is surprisingly non-dated. Some of the fake internet businesses he mentions even seem like good ideas to me now! Favorite bits: "I suppose it's a privilege of youth to be admired and admonished by the wise guys who have gone before." -p. 19 "VCs, I explained, want to know three basic things: Is it a big market? Can your product or service win over and defend a large share of that market? Can your team do the job?" - p.30 "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?" -p.83 "Passion pulls your 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. Once you gain a modicum of self-knowledge, you can express your passion. But it isn't just the desire to achieve some goal or payoff, and it's not about quotas or bonuses or cashing out. It's not about jumping through someone else's hoops. That's drive." -p. 83-84 "Silicon Valley veterans share a tacit understanding that what a startup needs isn't once CEO, but three–each at successive stages of the startup's development. GIven my deep regard for man's best friend, I Tend to think of each in terms of best of breed. The first CEO is 'the Retriever.' From the muck she must assemble the core team, the product or service, and the market direction–all around a coherent vision. She must also raise the money and secure crucial early customers and partners. She is prized for her tenacity and inventiveness. The second CEO is 'the Bloodhound.' He must sniff out a trail–find the market and prove the business. He needs to build an operating team and establish a market beachhead. He is prized for his keen sense of direction and company-building skills. The third CEO is 'the Husky.' She must lead the team, pulling an operating company that grows heavier by the day with people and public company responsibilities. She is prized for he constancy and scalability. None of these, to me, is top dof. All are equal in importance. just different in skills and temperaments." -p. 130 "And then there is the most dangerous risk of all–the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later." -p. 154

  2. 4 out of 5

    Matthew Trinetti

    How This Resonates With Me: The author’s opinion of the interdependent relationship of work and life is something I believe in wholeheartedly. Life is brief, and it’s wasteful to spend time doing things that do not align with your passions or gifts. The brevity of life is a lesson my friend Shannon dealt me firsthand and I try to remind myself of this everyday. Related to this, the author challenges a societal norm he calls The Deferred Life Plan. It’s a concept I always had a hard time buying How This Resonates With Me: The author’s opinion of the interdependent relationship of work and life is something I believe in wholeheartedly. Life is brief, and it’s wasteful to spend time doing things that do not align with your passions or gifts. The brevity of life is a lesson my friend Shannon dealt me firsthand and I try to remind myself of this everyday. Related to this, the author challenges a societal norm he calls The Deferred Life Plan. It’s a concept I always had a hard time buying into as well, but feel more comfortable confronting that belief after reading this book. There’s a point in the book where Komisar mentions that gaining self-knowledge is so important when honing in on your passions and gifts. This is something that really resonates with me as I travel, learn to follow my intuition, and make decisions based on the options which excite me the most. The experience of my current trip coupled with the lessons in this book reaffirm my belief that taking a break from working in one’s life to work on it is so important. Criticism: This book was originally written in 2000, so the references to TiVo and WebTV feel a little dated. And given the speed of technology, twelve years is like a century in tech years. But it’s surprisingly not as archaic as I expected; although the names have changed, the lessons are timeless. Also, the writing isn’t very sophisticated and the way the story ends feels a little Disney-fied. It’s tough to be too critical of this though because the book delivers its lessons clearly. Twelve Take-Aways: 1. Entrepreneurs and immigrants have a lot in common. Using the example of his own grandparents immigrating to America from Russia and Germany, Komisar identifies an interesting similarity between these two groups: "I see a common gene among immigrants and entrepreneurs who strike out from the pack to pursue their dreams...some of these risk takers...have a profound impact on what happens in the world. They place bets on the future, often against fantastic odds." 2. Venture capitalists and their role in the startup economy can be demystified. There are several scenes in the book depicting a discussion between entrepreneur and venture capitalist, and occasionally some passages that look into the mind of a VC. "Venture Capitalists want to know three basic things when investing in a business. Is it a big market? Can your product or service win over and defend a large share of the market? Can your team do the job?" 3. There should be a deeper purpose driving you to start a business besides money. A business shouldn’t be started as a means to an end. A business should be built for the purpose of building it and making a positive impact, not just for the success and reward that may come. Put another way, “the journey is the reward.” "There must be something more, a purpose that will sustain you when things look bleakest. Something worthy of the immense time and energy you will spend on this, even if it fails." 4. Business, more so than any other institution, has the potential for creative expression and positive change. "The rules of business are like the laws of physics, neither inherently good nor evil, to be applied as you may. You decide whether your business is constructive or destructive. I help people understand this and express themselves in what they do, trying to make a difference through business." 5. Most of us have been living life according to the “Deferred Life Plan”. T here are two steps in life according to this plan. Step one: Do what you have to do. Then, eventually – Step two: Do what you want to do. This concept implies that we should spend our life working hard doing something uninspiring so we can retire one day and then devote our time to our passion. The problem is our life’s timeline is unknown. We may never reach “one day.” "The Deferred Life Plan also dictates that we divorce who we are and what we care about from what we do in that first step...we hope and suppose that when we get [to the second step], we will be able to resurrect our passions on our own terms. If we get there." 6. There’s a difference between a Big Idea and a Business Model. Komisar brings this point home by discussing Apple’s tumultuous times under Sculley, where the CEO began operating Apple to a business model rather than a big idea, the way Jobs did (and eventually would re-do). "Business conditions are forever changing. You need to reconsider your strategies and business models constantly and adjust them when necessary. But the big idea that your company pursues is the touchstone for these refinements." 7. Business is about people. This is a concept that Chris Guillebeau hammers home in The $100 Startup as well. "Business...is about nothing if not people. First, the people you serve, your market. Then the team you build, your employees. Finally, your many business partners and associates. Sever the chain of values between leadership and the people translating strategy into products and services for your customers, and you will destroy your foundation for long-term success." 8. Your Passion is not the same as your Drive. This is an interesting distinction I had never considered before. In reference to the steps in the Deferred Life Plan, drive is what you experience in the first step, and passion is what you hope to experience after you’ve put in your time. "Passion pulls you toward something you cannot resist. Drive pushes you toward something you feel compelled or obligated to do." 9. It requires true self-knowledge to understand your passion. "If you know nothing about yourself, you can't tell the difference [between passion and drive]. Once you gain a modicum of self-knowledge, you can express your passion." 10. If management is a science, leadership is an art. "[Management]'s purpose is to produce the desired results on time and on budget. It complements and supports but cannot do without leadership, in which character and vision combine to empower someone to venture into uncertainty." "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." 11. Personal risks need to be evaluated with just as much scrutiny as business risks. Personal risks include the risk of working with people you don’t respect, the risk of working for a company whose values don’t align with your own, the risk of doing something you don’t care about, or the risk of doing something that does not express who you are. "And then there is the most dangerous risk of all -- the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later." 12. The value of time > the value of money. By valuing your time more than you value money, you’re able to appreciate each moment and live a more fulfilling existence spending your time doing something worthwhile. The alternative notion is thinking money can buy you the happiness you’ve missed out while you were focused on acquiring things. The problem is you don’t know when it will be too late. "Marrying our values and passions to the energy we invest in work...increases the significance of each moment. Consider your budget of time in terms of how much you are willing to allocate to acquiring things versus how much you are willing to devote to people, relationships, family, health, personal growth, and the other essential components of a high-quality life."

  3. 5 out of 5

    Christin.P

    If you’re a first-time entrepreneur looking for ways to fund your business but are unsure how to approach potential Venture Capitalists successfully, this book would have to be on your reading list. Its key “Do’s and Don’ts before, during and after pitching to VCs” are practical and illustrated in entertaining detail through Lenny’s story – an entrepreneur in his twenties who’s got some solid lessons to learn before he’s able to generate the much-needed funds to get his business idea off the If you’re a first-time entrepreneur looking for ways to fund your business but are unsure how to approach potential Venture Capitalists successfully, this book would have to be on your reading list. Its key “Do’s and Don’ts before, during and after pitching to VCs” are practical and illustrated in entertaining detail through Lenny’s story – an entrepreneur in his twenties who’s got some solid lessons to learn before he’s able to generate the much-needed funds to get his business idea off the ground. While Komisar’s book plays it safe in terms of the content he covers (you will find yourself thinking: “Yeah, I’ve heard that before.”), the basics of long-term business success coupled with personal fulfillment are as valid as ever. And they are worth being summed up again because – hand to heart – most of us think we’ve got it all figured out when in fact a refresher won’t hurt: 1: Time vs. Money. Make work pay you not only in cash, but also in experiences, satisfaction, joy and growth. Though they may not pay the rent, they do provide their own rewards and are durable in the face of adversity, as Komisar rightly points out. 2: People first. Invest your time in building relationships, growing your network, getting to know your customers’ needs and wants, your employees’ motivations and fears. Focus on what you have in common, not on what differentiates you. The reward for your engagement with others is the kind of trust that takes your business to the next stage and helps you navigate through tough times with more confidence. 3: Risk is part of the equation. Go all in and take a risk with your business idea, your talent, your commitment, your passion. Promote the big picture, not just a stable revenue forecast when pitching to potential VCs. Because by aiming at financial security alone, you will inevitably find yourself on the path to mediocrity. And mediocrity has never helped shape the world (or attracted much funding). 4: Drive vs. Passion aka The Deferred Life Plan. What drives you to get a job done isn’t necessarily the same thing you’re passionate about. Yet, most people are sold on an idea that Komisar calls the Deferred Life Plan: Work now, live later. But who’s to say that you can’t pay the mortgage, the kids’ tuition, the big holiday overseas or whatever else you desire with a career/business that expresses who you are and what’s important to you today? There’s no need to separate your present from your future – “Do what you have to do” and “Do what you want to do” can go hand in hand if you’re courageous and determined enough to make it happen. 5: Key questions to answer. If you want to successfully secure funds or business partners, there are several questions you need to answer for yourself: The WHY before the WHAT. * Why are you doing it? * What’s important to you? * What do you care about? * And how can you express this in your business? Your Product/Service. * Is it a big market? * Can your product/service win over and defend a large share of that market? * Can your team do the job? *see below * Will your product/service change the way the world operates? * Will it change people’s lives in a meaningful way? * What’s your Five-Year-Plan? * What’s your Unique Selling Point, and how do you stay competitive? * How will people find you when they need you? * How to you establish your brand and a presence? Key skills of you and your team members. * Be skilled in your functional area(s) * Be flexible and capable of learning quickly * Be intelligent and tireless * Be able to course-correct as you go * Be comfortable with uncertainty and change, thrive in chaos If you can’t present solid answers to any of the above, VCs, business angels and the like will be less inclined to collaborate with you. As for Lenny, he was lucky because Randy Komisar saw the potential in him and his idea – but you wouldn’t want to leave the success of your pitch to luck, would you?

  4. 4 out of 5

    David Hornik

    I teach an entrepreneurship class to law students and assign The Monk and The Riddle to the class. It is a great book for law students to read because it forces them to think about why they are going to law school, what they are hoping to get out of it, what will ultimately make them happy. While that is arguably a sub-theme of the book, I find it the most interesting piece of the conversation with my students. On the other hand, the bulk of the book is focused on an entrepreneur's quest to get I teach an entrepreneurship class to law students and assign The Monk and The Riddle to the class. It is a great book for law students to read because it forces them to think about why they are going to law school, what they are hoping to get out of it, what will ultimately make them happy. While that is arguably a sub-theme of the book, I find it the most interesting piece of the conversation with my students. On the other hand, the bulk of the book is focused on an entrepreneur's quest to get funded. Randy Komisar, the book's author, gets to play Sherpa for this wayward entrepreneur as he makes his way through the process of founding a company and getting funded. While the business upon which the book focuses is somewhat dated (funerals.com), the lessons learned are still relevant and valuable. My students continue to enjoy The Monk, as do I each year as I re-read it before class.

  5. 5 out of 5

    Mikko Eerola

    A good, quick, enjoyable read. A word of warning: this is a potentially dangerous book. It may make you rethink your priorities in life.

  6. 4 out of 5

    Lisa Marie O'Connor

    Enjoyable read although it didn't tell me anything new, having studied online entrepreneurship, worked in tech start-ups and watched many of the Silicon Valley tech founders on Ted Talks, You Tube etc as part of college study. Maybe I'm too immersed in it but it just seemed to confirm the message any startup founder knows, that there are no 'get rich quick' ideas and if you're in it for the money, get out and find a new idea that you love. Find the 'why' - any start-up that isn't 'love' is a Enjoyable read although it didn't tell me anything new, having studied online entrepreneurship, worked in tech start-ups and watched many of the Silicon Valley tech founders on Ted Talks, You Tube etc as part of college study. Maybe I'm too immersed in it but it just seemed to confirm the message any startup founder knows, that there are no 'get rich quick' ideas and if you're in it for the money, get out and find a new idea that you love. Find the 'why' - any start-up that isn't 'love' is a waste of your resources. The customer comes first, your idea must be customer-centric, empathy, what will your company's contribution to the world be etc and other questions to ponder. Having read it, I'm still not sure why it has the name 'The Monk and The Riddle'.... Maybe it was explained in the book but I've forgotten? Quick and enjoyable to read and might inspire if you are mulling over some potential startup ideas!

  7. 5 out of 5

    Kirill

    Unlike all other business books I've read, this one is mercifully short, focused on one big idea, and told as a story. Aside from that, I could not put the book down because it really appeared in my life at the right time to ask the question what I am passionate about my passion in life. Now I am a almost a full believer in abandoning the "Deferred Life Plan" -- do nonsense now to make money, live later -- except that I don't know what I am deferring. I do also like how subtly the benchmarks for Unlike all other business books I've read, this one is mercifully short, focused on one big idea, and told as a story. Aside from that, I could not put the book down because it really appeared in my life at the right time to ask the question what I am passionate about my passion in life. Now I am a almost a full believer in abandoning the "Deferred Life Plan" -- do nonsense now to make money, live later -- except that I don't know what I am deferring. I do also like how subtly the benchmarks for thoroughness, scope, and purpose of business plans are worked into the story. So definitely worth a read. The cons are tired references to attending business meetings in motorcycle gear, buddhism, monks, and hip-ly traveling and associating with "creative" people in college as tokens of creative and fulfilling life. Also, the message is relatively generic so I don't think this book will be reprinted hundred years from now. But then again, it has been reprinted in 2010, ten years since it's original publication. You never really know, I suppose. Thanks to Lloyd Wang for lending me the book.

  8. 5 out of 5

    Russ

    The book is a bit dated as it written before the 2001 dot com implosion. But it really isn't about that era or Silicon Valley even as the story follows a start-up wannabe being guided by the author. It really is about finding a life worth living in the moment and not deferring it until you're too old, tired or sick to enjoy it. There's a great discussion of the difference between passion and drive and which one should be the priority. It's a quick read that should confirm our new found bias The book is a bit dated as it written before the 2001 dot com implosion. But it really isn't about that era or Silicon Valley even as the story follows a start-up wannabe being guided by the author. It really is about finding a life worth living in the moment and not deferring it until you're too old, tired or sick to enjoy it. There's a great discussion of the difference between passion and drive and which one should be the priority. It's a quick read that should confirm our new found bias towards living a life of purpose in the moment. Spoiler - he never answers the riddle.

  9. 5 out of 5

    Yvette Bowlin

    A little misleading, the title and the actual content in the book. A story about a silicon valley ex-VC and how he helps entrepreneurs stay true to themselves as they pursue success. I don't particularly get excited about the premise, but I do like the setting. The low rating is because I wasn't thrilled at the plot and I didn't really believe Komisar. His stories seemed far-fetched and too "perfect." Just seemed contrived and too heavy-handed on the "spiritualism."

  10. 4 out of 5

    Dano

    If you are an entrepreneur or wish to be or even just looking for financial meaning in your life this book is a must read. It is about, as Joseph Campbell said, following your bliss. We all have hopes and dreams and ideas about success: this book is about staying the course.

  11. 4 out of 5

    Fahasa

    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 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. Described by Fortune.com as "part personal essay, part fictional narrative and part meditation on the nature of work and life," "The Monk and the Riddle" is essential reading on the art of creating a life while making a living. 'Belongs in a category by itself...The best thing I've read all year' - "San Francisco Examiner". 'A timely book' - "USA Today". 'A self-help manual and business fable rolled into one' - "The Times, London". https://www.fahasa.com/

  12. 5 out of 5

    Juliette Weiss

    “Don’t confuse drive and passion. Drive pushes you forward. It’s a duty, an obligation. Passion pulls you. It’s the sense of connection you feel when the work you do expresses who you are. Only passion will get you through the tough times.” Bought this book years ago for Danny Warshay’s Entrepreneurship class and finally got a chance to read it. And wow, it could of have been at a better time! The big picture advice, like the difference between leadership + management or drive + passion, made me “Don’t confuse drive and passion. Drive pushes you forward. It’s a duty, an obligation. Passion pulls you. It’s the sense of connection you feel when the work you do expresses who you are. Only passion will get you through the tough times.” Bought this book years ago for Danny Warshay’s Entrepreneurship class and finally got a chance to read it. And wow, it could of have been at a better time! The big picture advice, like the difference between leadership + management or drive + passion, made me rethink the way I look at shaping my career going forwards. The more tactical advice, like needing three CEO’s - the retriever, the bloodhound + the husky, made me reconsider the ways I evaluate other businesses. A quick, yet powerful read. Would recommend to anyone, both early and late in their career.

  13. 4 out of 5

    Wanda

    What an outstanding book, well worth revisiting and deserving of sufficient time to digest its contents. It took me some time to be swept up by the main parable, the central pillar around which Komisar crafted his narrative, but once that had happened, I found myself relating it - as well as the highly pertinent asides selected from Komisar's own life - to other readings (e.g. The ideas of the stoics, as well as some that were later echoed by Cal Newport). This book isn't just about what's What an outstanding book, well worth revisiting and deserving of sufficient time to digest its contents. It took me some time to be swept up by the main parable, the central pillar around which Komisar crafted his narrative, but once that had happened, I found myself relating it - as well as the highly pertinent asides selected from Komisar's own life - to other readings (e.g. The ideas of the stoics, as well as some that were later echoed by Cal Newport). This book isn't just about what's needed to succeed in business; it provides a wholistic perspective of how one can lead a satisfying life made exceptional through the type of work you choose to undertake.

  14. 5 out of 5

    Tom Lambotte

    A solid, easy read with some great ideas and questions to make you think. This book was read by the author of Traction many years ago and it inspired him to becoming a business coach and doing what he does now. Big takeaway idea: “What are you willing to do for the rest of your life? It does not mean, literally, what will you do for the rest of your life? ...that would be absurd...what it really asks is, if your life were to end suddenly and unexpectedly tomorrow, would you truly be able to say A solid, easy read with some great ideas and questions to make you think. This book was read by the author of Traction many years ago and it inspired him to becoming a business coach and doing what he does now. Big takeaway idea: “What are you willing to do for the rest of your life? It does not mean, literally, what will you do for the rest of your life? ...that would be absurd...what it really asks is, if your life were to end suddenly and unexpectedly tomorrow, would you truly be able to say you’ve been doing what you truly care about today? What would you be willing to do for the rest of your life? What would it take to do that right now?”

  15. 4 out of 5

    Sally Duros

    This book inspired me to interview Randy Komisar for a column I was writing at the time. Passion – it’s on the ceiling! Posted on April 5, 2003 First Published in Sally’s World, April 2003 http://www.sallyduros.com/passion-its... By SALLY DUROS In the 80s, we worked hard. In the early 90s, we worked smart. In the late 90s, we worked fast. But now, firmly established in the new millennium, we are working all three, but most of all we are working passion. Today many of us have switched careers or spun This book inspired me to interview Randy Komisar for a column I was writing at the time. Passion – it’s on the ceiling! Posted on April 5, 2003 First Published in Sally’s World, April 2003 http://www.sallyduros.com/passion-its... By SALLY DUROS In the 80s, we worked hard. In the early 90s, we worked smart. In the late 90s, we worked fast. But now, firmly established in the new millennium, we are working all three, but most of all we are working passion. Today many of us have switched careers or spun out of traditional organizations into smaller more intimate ones – maybe even our own. It’s a realignment of values – we are giving up what doesn’t matter for what does matter. In seeking to live from our hearts in our work and personal lives, we are responding to the irresistible tug of passion. When passion is present, we don’t stop simply because something goes wrong. We feel the pain, yet we keep going. Having passion doesn’t mean that we will succeed. It simply means that our endurance and resilience are boosted by the power of our authentic presence. Working from passion might improve the likelihood of our success, while most certainly changing our definition of success. But don’t mistake drive for passion. Drive is a push, not a pull. It takes us away from, not into our hearts. Sometimes I can’t believe what a wonderful life I have because as a writer and a journalist, I often get to experience mind meld with fascinating and insightful people. Because of a book project that I am working on, I had one of those conversations the other day with Randy Komisar, author of The Monk and the Riddle: The Art of Creating a Life While Making a Living. Komisar, who is a long-time practitioner of Buddhism, integrates his life and his work with a powerful core belief: Time is short. Don’t squander any of it. Invest your time in only those things that are important. We were talking about passion and its role in start-up business. Komisar believes that women are better at recognizing and following passion than men are. I agree. To live from passion, you have to listen to your intuition and be open to hearing the beat of your personal drummer. Komisar says that women are more open-minded than men in this way, in part because men are slotted into the breadwinner role that women have traditionally been excluded from. “Women – it’s the other side of the curse, the curse being that they’ve not had the opportunities,” Komisar says.” Women because of that are open-minded about finding what matters. They are empowered because they are disempowered in the traditional sense. Women are much more creative, I think, and much more courageous in terms of looking for those things that really matter.” “If you think about it, (passion is at the core) of the traditional dilemma of being the super mom,” Komisar says. “You have your family and you have your career. What you see (in the struggle) is balancing two passions.” “Most of the women involved in the dialogue about balance of life and career are involved because they care about both, because they have passion.” Men are suffering more than women in this equation, Komisar says. “Talk to a 50-year old man about what he wants to do next, and he looks at you (lost) … I”ll play golf. There’s no dimensionality. Their whole identity is in one thing." Komisar, who teaches classes in entrepreneurship at Stanford, says he has learned much from students pushing against his ideas. He now more fully understands the multiplicity of passion. You may have many passions, and you will follow different passions at different times in your life. Personally, I have been giving passion free rein in my work for a while now. I can attest that it’s difficult, financial lunacy, and often lonely. But I can also attest to the breathless creative flow that occurs when I and my passion are working side by side. There’ s nothing like it. Except maybe this. When I was a 10-year-old kid, I and my best friend of the week would do shoulder stands on my living room couch and imagine that we were walking from room to room on the ceiling. We would step over the tops of door frames, whose structures formed little barriers between the rooms, creating an archipelago of ceiling space, and walk from island to island, checking the treasure that laid in the bowls of the glass light fixtures. Maybe it was the blood rushing to my head, but I used to wonder if my friend were seeing the same thing I was seeing as we explored the upside down world. I would fantasize that I was inside her brain, looking out from behind her eyes, walking on the ceiling from room to room, until it was time to go and I walked down the walls and out the door and across the street to eat dinner with her family. I would be me, but inside her head for just an hour or two, just long enough to understand what it was like to be her. I haven’t learned yet how to get inside the mind of another, but I have found the next best thing – the wisdom I am exposed to in a great interview and the fact that I can pass it on to you. What could be better? That’s passion!Monk and the Riddle: The Education of a Silicon Valley EntrepreneurRandy Komisar

  16. 4 out of 5

    Paul Fisher

    I really enjoyed this book. It was a quick read, and easy to follow. At first, I thought that the story was going to have characters that were over-developed and too typecast, and if it was a 300 page book it probably would have. But the short, concise nature of the story got to a point, and did so in a way that left the reader feeling that the length was just right. Short, but it did not need to be longer.

  17. 4 out of 5

    Monya De

    Not sure why MBA faculty are so into this. The artificial central conceit is Komisar stringing a poor founder along and imparting some blather about how his idea is not fundable because it is just an e commerce site. I'm sure Bezos would beg to differ and say you do not need a fancy story or emotional connection to your startup. Then he sort of meanders through his autobiography in between torturing the founder.

  18. 5 out of 5

    Chetan Chothani

    The strange intersection of a business book with a Fantasy Series (Stormlight Archives)! In his fantasy series, Brandon Sanderson emphasizes Journey before Destination as part of the immortal words of the Knights Radiants. Similarly, in this book, Randy Komisar, in a round about way teaches entrepreneurs that it is not about the destination, but rather its about the journey. Thoroughly enjoyable book. Brings perspective!

  19. 4 out of 5

    Jk

    This is a good narrative for those professionals who subscribe to the notion that "you only go around once..." while also asking themselves the question "what should I really be using my 'superpowers' for?" Although one could argue the author is traveling downhill a bit with a couple of explosive successes behind him, the counterpoint should argue does that really matter, or did that just give him the bandwidth to have the epiphany? Happy to have stumbled upon it. A quick read.

  20. 5 out of 5

    Ben

    This book can be summed up in one line—"Working with purpose is > working for money" It was entertaining, but ultimately it's use of a fictional narrative to recount the author's experience felt shallow and left me wanting more. Author could have done a better job at tying this lesson *directly* to his own life experiences and provide *real* examples in support of his philosophy.

  21. 5 out of 5

    Cassidy DeAngelis

    A book bought on complete impulse and purely based on the title, I have to say it was quite an eye opening read. Komisar takes a dive in to what it means to have a successful life, based on not just what you do but who you are at your core. He challenges the mainstream thinking that we should sacrifice our lives in order to make a living.

  22. 4 out of 5

    Randy Evans

    I was attracted to this one by the title but turned off when I found out it was a business book. I have it a pass but then came across it at a B&B when I had an afternoon with some time to kill. I am glad I did. It is a interesting look into the world of venture capital as well as the human quest for meaning. It is a light, quick touch on both accounts but a good one. Good riddle too.

  23. 5 out of 5

    Sebastian Patron

    A fantastic read that makes one think about where their passion and their drive comes from, and how to intersect the two. Komisar also introduces the concept of the deferred life plan, where one lives life doing what they have to do (step 1) in order to do what they want to do (step 2). Komisar warns against this, stating that it will lead to unhappiness and being unfulfilled. Short, easy read.

  24. 4 out of 5

    Arie

    Pretty good read Interesting style and substance. Some good tidbits on investing, but on a deeper level I think the author is getting at what life is all about and answer some deep stuff. Well written and unusual style of relaying a message.

  25. 4 out of 5

    Chinedu Okonkwo

    There is no connection between the title and the content of the book. Although it might be a good read for someone who has a startup and looking to raise money from venture capitalists in silicon valley. The riddle from the monk was in the prologue and was never solved

  26. 4 out of 5

    Metin Ozsavran

    İt's kinda dank, Stark and cold, but still informative. İt's Not a startup founders book, but a VC viewing founders from investors point of view. His not totally deserved utter self confidence gets in your nerves a little, but still a must read for every entrepreneur wannabe. :)

  27. 4 out of 5

    Jay Holls

    A honest and insightful book on the start ups universe.

  28. 4 out of 5

    Jason Dunn

    Very well written and entertaining look into the life of a venture capitalist.

  29. 5 out of 5

    Ram Muthukrishnan

    Quick read with lot's of musings about the broader purpose of one's life. Also includes interesting stuff about how vc's and start-up's work in silicon valley!

  30. 4 out of 5

    Nick

    A very good, expanded story on how VC works and looks at things

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