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

3.87  ·  Rating details ·  2,292 ratings  ·  150 reviews
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 "lea ...more
Hardcover, 224 pages
Published March 1st 2000 by Harvard Business Review Press
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Jessie Young
Apr 07, 2013 rated it really liked it
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 th
...more
Matthew Trinetti
Nov 10, 2012 rated it it was amazing
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 ha
...more
Christin.P
Apr 09, 2017 rated it liked it
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 gro ...more
David Hornik
Jan 03, 2013 rated it really liked it
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
...more
Mikko Eerola
Jun 29, 2008 rated it it was amazing
Recommended to Mikko by: Antti Vilpponen
Shelves: on-loan, i-own
A good, quick, enjoyable read.

A word of warning: this is a potentially dangerous book. It may make you rethink your priorities in life.
Lisa Marie O'Connor
Jan 19, 2017 rated it liked it
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 was ...more
Kirill
Oct 05, 2011 rated it liked it
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 ...more
Russ
Dec 22, 2017 rated it really liked it  ·  review of another edition
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 towa ...more
Yvette Bowlin
Mar 16, 2016 rated it it was ok
Shelves: nonfiction, spirit
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."
Dano
Jul 31, 2010 rated it really liked it
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.
Fahasa
Oct 30, 2019 rated it it was amazing
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 ...more
Juliette Weiss
Jan 15, 2018 rated it it was amazing
“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 dr
...more
Wanda
Sep 24, 2017 rated it it was amazing
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 neede ...more
Tom Lambotte
Feb 23, 2018 rated it really liked it
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
...more
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
...more
Paul Fisher
Jul 16, 2018 rated it it was amazing
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.
Monya De
Apr 09, 2019 rated it liked it
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.
Chetan Chothani
Oct 11, 2018 rated it liked it
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!
Jk
Jul 26, 2017 rated it really liked it
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 r
...more
Ben
Feb 05, 2018 rated it it was ok
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.

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.
Randy Evans
May 25, 2019 rated it really liked it
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.
Cassidy DeAngelis
Feb 20, 2019 rated it really liked it
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.
Arie
Dec 05, 2018 rated it liked it  ·  review of another edition
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.
Chinedu Okonkwo
Oct 12, 2018 rated it it was ok
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
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. :)
Jay Holls
Feb 01, 2018 rated it liked it
A honest and insightful book on the start ups universe.
Jason Dunn
Nov 09, 2017 rated it it was amazing
Very well written and entertaining look into the life of a venture capitalist.
Ram Muthukrishnan
May 20, 2018 rated it it was amazing
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!
Nick
Oct 25, 2017 rated it really liked it
A very good, expanded story on how VC works and looks at things
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Randy Komisar joined Kleiner Perkins in 2005 and focuses on early-stage investing.

Previously, he was a co-founder of Claris Corp., served as CEO for LucasArts Entertainment and Crystal Dynamics, and acted as “virtual CEO” for such companies as WebTV and GlobalGiving. Randy also served as CFO of GO Corp. and as senior counsel for Apple Computer, following a private practice in technolog
...more
“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.” 130 likes
“In theory, the risk of business failure can be reduced to a number, the probability of failure multiplied by the cost of failure. Sure, this turns out to be a subjective analysis, but in the process your own attitudes toward financial risk and reward are revealed.

By contrast, personal risk usually defies quantification. It's a matter of values and priorities, an expression of who you are. "Playing it safe" may simply mean you do not weigh heavily the compromises inherent in the status quo. The financial rewards of the moment may fully compensate you for the loss of time and fulfillment. Or maybe you just don't think about it. On the other hand, if time and satisfaction are precious, truly priceless, you will find the cost of business failure, so long as it does not put in peril the well-being of you or your family, pales in comparison with the personal risks of no trying to live the life you want today.

Considering personal risk forces us to define personal success. We may well discover that the business failure we avoid and the business success we strive for do not lead us to personal success at all. Most of us have inherited notions of "success" from someone else or have arrived at these notions by facing a seemingly endless line of hurdles extending from grade school through college and into our careers. We constantly judge ourselves against criteria that others have set and rank ourselves against others in their game. Personal goals, on the other hand, leave us on our own, without this habit of useless measurement and comparison.

Only the Whole Life Plan leads to personal success. It has the greatest chance of providing satisfaction and contentment that one can take to the grave, tomorrow. In the Deferred Life Plan there will always be another prize to covet, another distraction, a new hunger to sate. You will forever come up short.”
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