Monk & the Riddle – Empathy and Compassion MBA Style :-)

If you’re in the Technology business or doing an MBA Monk and the Riddle is essential reading. This book has a narrow focus and succeeds there.

Randy Komisar’s personal epiphany is that business is about people. His book’s story arc is a great vehicle to introduce and explore many of the “people” involved in the technology business. Randy uses himself to portray the “mercenary” lawyer, then the “mercenary” business development guy, the somewhat “compassionate” CEO, “sage” Angel Investor, and later VC (not part of book). He talks about his experiences with Apple/Claris Exec Bill Campbell that forced him to see the light. That business is about people.

This book spends a lot of time discussing the startup founder “battle” of “do it for money” or “do it for love”. This dialogue is well done with Komisar playing the “sage” Angel Investor providing advice to characters “Lenny (I’m in it for the money)” and “Alison (I’m in it for love. I want to change the world.)” The key point that Komisar makes is that most of the big successes have been done when the majority of the focus is on love. ( ie You’ve got to solve real problems for real people).

This book is very complementary to Steve Blank’s Four Steps to the Epiphany and Eric Ries’ Lean Startup. It fills in the gaps that those books have on the people side of the startup game. If you’re reading those you should also read “Monk and the Riddle”.


I can see why a lot of the Amazon 1-Star reviewers hate this book. It has little to do with eradicating competitive business tactics or discussing work life balance tradeoff’s. This book is all about “ideas” that get funded and finding a way to stay motivated in a startup. Working 24/7 for money is doable over a period of months, but most startup endeavors are 7 years or more. Thus you’d better love what your doing, and investors want to know that. This is a KPBC VC talking, not the Dalai Lama.

That said, I’d like to congratulate Randy Komisar for putting himself in the public eye with this book. He’s got some good stuff to say about one’s career. The fact that he is a KPBC VC will always rub some people the wrong way. Too bad for them.

I’ve been curious about Randy Komisar’s Monk and the Riddle: The Art of Creating a Life While Making a Living ever since I saw it on the reading list of Stanford’s E145 Technology Entrepreneurship course. I thought — “a “life” book from a VC? Weird.” My gut was right. It’s not that. But it is a worth while read if one is in the target audience.

Odd point — the subtitle has changed over time. I think the first title (hardcover) is more representative of the content.
The original Title was Monk and the Riddle: The Education of a Silicon Valley Entrepreneur and the new title is “Monk and the Riddle: The Art of Creating a Life While Making a Living.

If you’re looking at a work and life balancing book. Give Tim Ferris’s 4-Hour Work Week a try. Good fun and good ideas.