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

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Copyright 2010 Randy Komisar
All rights reserved

 

The Web sites or URLs mentioned in this book originated in my imagination. Some of them may coincide with the names or URLs of real sites. This is fortuitous, and no resemblance should be inferred. All references to my life — personal and professional—are based in fact, but they reflect my interpretation of events. Lenny, Allison, and Frank are composite portraits of would-be entrepreneurs and venture capitalists with whom I interact daily. Their characters and their dialogue, however fictionalized, are true to my experiences.

 
 
C
ONTENTS

 

Preface to the New Edition: P
OSTMORTEM

 

Prologue    T
HE
R
IDDLE

 

          
1    T
HE
P
ITCH

 

          
2    T
HE
R
ULES OF THE
G
AME

 

          
3    T
HE
V
IRTUAL
CEO

 

          
4    T
HE
D
EFERRED
L
IFE
P
LAN

 

          
5    The R
OMANCE
, N
OT THE
F
INANCE

 

          
6    T
HE
B
IG
I
DEA

 

          
7    T
HE
B
OTTOM
L
INE

 

          
8    T
HE
A
RT OF
L
EADERSHIP

 

          
9    T
HE
G
AMBLE

 

        
10    T
HE
W
HOLE
L
IFE
P
LAN

 

Epilogue    T
HE
R
OAD

 

           
A
CKNOWLEDGMENTS

 

           
A
BOUT
THE
A
UTHORS

 
Praise for
The Monk and the Riddle
and Randy Komisar
 

“[Komisar's] advice for people in any business to junk the ‘Deferred Life Plan’ and live for the moment is a message everyone can appreciate.”

 


Publisher's Weekly

 

 

“Komisar delivers this inspirational advice with a Zen-like detachment…. The result is part instruction manual, part visionary manifesto for humanizing a cultural revolution whose get-rich-quick optimism may be only a version of old-fashioned boosterism recast for an entrepreneurial millennium.”

 


Washington Post Book World

 

 

“So interesting and well-written you almost don't want to put it down.”


Fortune.com

 

 

“A disarming … book that injects some welcome spirit into a stiff genre.”

 


Wired

 

 

“The Monk and the Riddle
is a reminder that we do not need to sacrifice our lives to make a living. Komisar offers a long-overdue antidote to today's cash-in—cash-out mentality.”

 


Stewart Alsop, Columnist,
Fortune

 

 

“This book makes you laugh. It makes you want to cry. But most important, it makes you stop and think.”

 


Bruce Judson, Author,
HyperWars
and
Net Marketing

 

 

“Mentor, guide, chief strategist and even spiritual adviser … For Komisar, perfecting the role of virtual CEO has been an opportunity to pare leadership to its essence.”

 


San Jose Mercury News

 

 

“[Komisar is] part sensitive coach, part tough-talking businessman.”

 


Business 2.0

 
T
HE
M
ONK
AND THE
R
IDDLE
T
HE
M
ONK
AND THE
R
IDDLE

 

 

T
HE
A
RT OF
C
REATING A
L
IFE WHILE
M
AKING A
L
IVING

 

R
ANDY
K
OMISAR
WITH KENT LINEBACK

 

For D2 and T
2

 

Every moment some form grows perfect in hand or face; some tone on the hills or the sea is choicer than the rest; some mood of passion or insight or intellectual excitement is irresistibly real and attractive to us—for that moment only. Not the fruit of experience, but experience itself, is the end. A counted number of pulses only is given to us of a variegated, dramatic life. How may we see in them all that is to be seen in them by the finest senses? How shall we pass most swiftly from point to point, and be present always at the focus where the greatest number of vital forces unite in their purest energy? To burn always with this hard, gemlike flame, to maintain this ecstasy, is success in life.

—Walter Pater,
Studies in the History of the Renaissance
(1873)

 

Preface to the New Edition

 

P
OSTMORTEM

 

I
T HAS
been only two and a half years since Kent Lineback and I sat down to write
The Monk and the Riddle
and a short year since its release, but things have certainly changed dramatically.

The millennium celebration marked a decade of prosperity that had boiled over into giddy enthusiasm for a future limited only by our imaginations. The Internet epitomized this boundless optimism and permeated every corner of the media. The stock market became the barometer of our exuberance. But today people fear the future with the guilt of a child who has had too much fun and expects to pay the price.

A year ago, the NASDAQ was soaring at over 5,000; now it sulks at less than 2,000. Last year, dot-coms were proclaimed the monarchs of the so-called New Economy; now even the blue chips of the technology industry such as Cisco, Oracle, and Microsoft are trading near fifty-two-week lows. In 1999, venture capitalists could not get their fill of dot-coms; today promising teams and ideas starve without capital. A year ago, carpetbaggers and speculators poured into startups pronouncing themselves smart and rich; but in the wake of today's dot-com bankruptcies and layoffs, many young wannabes are slinking off to work their way up the corporate ladder instead. Day traders once exchanged suits for T-shirts and tasseled loafers for sandals, making money thoughtlessly as they clicked away on keyboards; today they are all but washed out. And it seems like an eternity since Amazon's Jeff Bezos smiled at us triumphantly from the cover of
Time
as 1999's Man of the Year. This year, he is downsizing and jettisoning unpromising business units just to stay afloat.

What the heck happened?

I
WISH
I could say that I saw all of this coming. Like a few other skeptics, I felt certain that the dot-com bubble would burst.
The Monk
in fact employs the metaphors of death and funerals not just to poke fun at the silly excesses of the mania, but more importantly to foreshadow its demise. Still, the severity of the boom and bust, the polarity of investor optimism and pessimism, and the devastating impact on the best of companies surprised even me.

When I started to write
The Monk
, I was unsure of how the book would be received by my close friends and associates as well as by the market at large. I felt distinctly alone looking the dot-com gift horse in the mouth. I had partaken of its gifts most willingly and was not happy to conclude that they were unsustainable. But people I greatly respect were certain that I was being alarmist.

I wrote the book anyway.

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.

Business is tough. Tenacity and endurance are key to business success. But tenacity is seldom sustained simply by the drive for riches. Endurance most often wanes in the face of persistent obstacles if money is the overwhelming objective.

During this time of reflection and commercial penance, the messages of
The Monk
seem more applicable than ever. No matter how hard we work or how smart we are, our financial success is ultimately dependent on circumstances outside our control. (Ask any once high-flying startup that is currently looking for a life-saving round of financing in these bleak times.) In order to find satisfaction in our work, therefore, we should train our attention on those things that we can influence and that matter to us personally.

The Monk
encourages us to consider how we spend our time, not our money. Marrying our values and passions to the energy we invest in work, it suggests, 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. 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 money ultimately cannot buy much of life's total package anyway, why waste precious time earning more for its own sake?
The Monk
encourages us to make work pay, not just in cash, but in experience, satisfaction, and joy. These sources of contentment provide their own rewards and are durable in the face of adversity. We still have an opportunity to retune the balance between passion and drive—to express ourselves holistically in what we do, rather than to defer what is important until it is too late.

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