On The Monk and the Riddle

I recently finished reading The Monk and the Riddle – The Education of a Silicon Valley Entrepreneur – by Randy Komisar with Kent Lineback.

This is a book that narrates, through the dialogue between a mentor (Komisar) and two entrepreneurs seeking to launch their business, valuable lessons on entrepreneurship, and leadership. It takes us through the lifecycle of a start-up from inception to execution.  What sets this book apart is that the narration showcases both the investor’s point of view (VC) and the entrepreneurs looking to start their business. Through this the reader learns the gap that can and usually does exist between the two and how to mediate that.

A very educational, insightful and entertaining read!

Below are key excerpts from the book that I found particularly insightful:

1- “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?”

2- “VCs invest first and foremost, I explained, in people. The team would have  to be intelligent and tireless. They would need to be skilled in their functional areas, though not necessarily highly experienced. Moreover, they would need to be flexible and cable of learning quickly. Heaps of information about the market and the competition would be streaming in after they launched. They would have to course-correct, on would have to be comfortable with uncertainty and change. That’s why VCs look for people with some startup experience, people who have proven they can thrive in chaos. It significantly reduces the risk of failure.”

3- “It’s not clear that being the first-mover will provide the rash of Internet startups a sustainable competitive advantage. Ultimately being right, or better positioned, may be more important than being first.”

4- “Stay small and remain flexible for the time being, so we can keep close to the market, learn from prospective customers, and afford to take some missteps. You have o be able to survive mistakes in order to learn, and you have to learn in order to create sustainable success. Once the market is understood and the product is fully developed, then move fast and hard. If, on the other hand, we discover with this approach that there’s no market at all, we won’t have wasted truckloads of money.”

5- “Business is one of the last remaining social institutions to help us manage and cope with change.”

6- “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. Once you gain on modicum of self-knowledge, you can express your passion.”

7- “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 longer-term success. The culture you create and principles you express are the only connection you will have with each other and your many constituencies.”

8- “Silicon Valley veterans share a tacit understanding that what a startup needs isn’t one CEO, but three – each at successive stages of the startup’s needs isn’t one CEO, but three – each at successive stage of the startup’s development…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 her constancy and scalability. None of these, to me, is top dog. All are equal in importance, just different in skills and temperaments.”

9- “Management and leadership and related but not identical…Management is a methodical process’ its 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. Leaders must suspend the disbelief of their constituents and move ahead even with very incomplete information.”

10- “I liked being the leader better than being the guy who made the trains run on time. 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 be great; and in getting them to do it all together, in harmony. That was the high art.”


Omar Halabieh

The Monk and the Riddle

The Monk and the Riddle



  1. Love the summary, I need to read this book too, heard it was amazing aswell! I came across this title in the four hour work week by Timothy Ferris. That one is a amazing aswell!

    1. Hi Harp,

      Below are the key excerpts that I saved from that book (4 hour work week):

      -Step by Step process you’ll use to reinvent yourself:
      -D for Definition turns misguided common sense upside down and introduces the Rules and objectives of the new game. It replaces self-defeating assumptions and explains concepts such as relative wealth and eustress. This section explains the overall lifestyle design recipe – the fundamentals – before we add the three ingredients.
      -E for Elimination kills the obsolete notion of time management once and for all. It shows exactly how I used the words of an often-forgotten Italian economist to turn 12-hour days into two hour days. This section provides the first of the three luxury lifestyle design ingredients: time.
      -A for Automation puts cashflow on autopilot using geographic arbitrage, outsourcing, and rules of nondecision. This section provides the second ingredient of luxury lifestyle design: income.
      -L for Liberation is the mobile manifesto for the globally inclined. The concept of mini-retirements is introduced, as are the means for flawless remote control and escaping the boss. This section delivers the third and final ingredient for luxury lifestyle design: mobility.
      -Rules that change rules:
      -Retirement is worst-case-scenario insurance
      -Interest and energy are cyclical
      -Less is not laziness
      -The timing is never right
      -Ask for foregiveness, not permission
      -Emphasize strengths. Don’t fix Weaknesses.
      -Things in excess become their opposite.
      -Money alone is not the solution.
      -Relative income is more important than absolute income.
      -Distress is bad, eustress is good.
      -Dodging the bullets:
      -Define your nightmare, the absolute worst that could happen if you did what you are considering.
      -What steps could you take to repair the damage or get things back on the upswing, even if temporarily?
      -What are the outcomes or benefits, both temporary and permanent, of more probable scenarios?
      -If you were fired from your job today, what would you do to get things under financial control?
      -What are you putting off out of fear?
      -What is it costing you – financially, emotionally, and physically – to postpone action?
      -What are you waiting for?
      -Excitement is the more practical synonym for happiness, and it is precisely what you should strive to chase. It is the cure-all.
      -Effectiveness is doing things that get you closer to your goals. Efficiency is performing a given task (whether important or not) in the most economical manner possible. Being efficient without regards to effectiveness is the default mode of the universe. Here are two truisms to keep in mind:
      -Doing something unimportant well does not make it important.
      -Requiring a lot of time does not make a task important.
      -The end of time management:
      -Most things make no difference. Being busy is a form of laziness – lazy thinking
      and indiscriminate action. The lack of time is actually lack of priorities.
      -There are two synergetic approaches for increasing productivity that are inversions of each other:
      -Limit tasks to the important to shorten work time (80/20).
      -Shorten work time to limit tasks to the important (Parkinson’s law).
      -Empowerment Failure:
      -For the employee, the goal is to have full access to necessary information and as much independent decision-making ability as possible. For the entrepreneur, the goal is to grant as much information and independent decision-making ability to employees or contractors as possible.
      -Interrupting interruption and the art of refusal:
      -Create systems to limit your availability via e-mail and phone and deflect inappropriate contact.
      -Batch activities to limit setup cost and provide more time for dreamline milestones.
      -Set or request autonomous rules and guidelines with occasional review of results.
      -Outsourcing life: common complaints:
      -I accepted the first person the firm provided and made no special requests at the outset.
      -I gave imprecise directions.
      -I gave him a license to waste time.
      -I set deadlines a week in advance.
      -I gave him too many tasks and didn’t set an order of importance.
      -Disappearing Investment:
      -Increase investment
      -Prove increased output offsite
      -Prepare the quantifiable business benefit
      -Propose a revocable trial period
      -There are several principal phobias that keep people on sinking ships, and there are simple rebuttals for all of them:
      -Quitting is permanent.
      -I won’t be able to pay the bills.
      -Health insurance and retirement accounts disappear if I quit.
      -It will ruin my resume.
      -There are two types of mistakes: mistakes of ambition and mistakes of sloth. The first is the result of a decision to act – to do something. This type of mistake is made with incomplete information, as it’s impossible to have all the facts beforehand. This is to be encouraged. Fortune favors the bold. The second is the result of a decision of sloth – to not do something – wherein we refuse to change a bad situation out of fear despite having all the facts. This is how learning experiences become terminal punishments, bad relationships become bad marriages, and poor job choices become lifelong prisons.
      -If you can’t define it or act upon it, forget it.
      -The top 13 new rich mistakes:
      1. Losing sight of dreams and failing into work for work’s sake
      2. Micromanaging and e-mailing to fill time
      3. Handling problems your outsourcers or co-workers can handle
      4. Helping outsourcers or co-workers with the same problem more than once, or with noncrisis problems
      5. Chasing customers, particularly unqualified or international prospects, when you have sufficient cash flow to finance your non-financial pursuits.
      6. Answering e-mail that will not result in a sale or that can be answered by a FAQ or auto-responder
      7. Working where you live, sleep, or should relax
      8. Not performing a thorough 80/20 analysis every two to four weeks for your business and personal life
      9. Striving for endless perfection rather than great or simply good enough, whether in your personal or professional life
      10. Blowing minutiae and small problems out of proportion as an excuse to work
      11. Making non-time-sensitive urgent in order to justify work
      12. Viewing one product, job, or project as the end-all and be-all of your existence
      13. Ignoring the social rewards to life


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