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

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An insightful & humorous narrative about a Silicon Valley Insider's search for deeper meaning in business. The Monk and the Riddle tells of how one Silicon Valley insider has blazed a path of professional, and personal, success playing the game by his own rules. It offers insights into how to lead and mentor and how to pace a start-up business.

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Editorial Reviews

Kathleen Doler
The Monk is well written and it keeps the reader wanting to find out what’s going to happen with those entrepreneurs. It’s much more engaging and amusing than your average 10-step-plan management tome. Bottom line: It's worth the cover price for a short, thought-provoking read.
Electronic Business Magazine
USA Today
A timely book.
San Francisco Examiner
Belongs in a category by itself . . . The best thing I've read all year.
Times London
A self-help manual and business fable rolled into one.
Publishers Weekly - Publisher's Weekly
Not your typical how-I-made-my-Internet-millions screed, Komisar's look at the "riddle" of making work meaningful offers a healthful but not always compelling dose of wisdom for Silicon Valley entrepreneurs. You might call it Zen and the art of venture capitalism, a blend of off-the-shelf business nostrums with a more searching inquiry into the meaning of success in today's supercharged New Economy. The action opens at a Valley coffee shop where Komisar greets his first pitch of the day--from, an online purveyor of funeral goods--with due skepticism. But he soon comes to feel that the pitchman might have hit upon a brilliant idea, if he would only surrender his bottom-line attitude for a more personally fulfilling vision of what his company could become. Komisar, one-time chief of LucasArts Entertainment and currently a "Virtual CEO" for a variety of Silicon Valley firms, uses the pitch as the occasion for a journey through the mechanics of successful Internet ventures. Along the way, he examines pairs of opposing business paradigms--passion and drive, romance and finance, leadership and management, even inspiration and perspiration--and argues that the "big idea" will win out over the "business model" in Silicon Valley, because passion ultimately matters more than price cutting or market valuations. While well-meaning, Komisar's insistence that entrepreneurs "strive for excellence" can seem trite. On the other hand, his advice for people in any business to junk the "Deferred Life Plan" and live for the moment is a message everyone can appreciate. $50,000 ad/promo; 35,000 first printing. (May) Copyright 2000 Cahners Business Information.|
Kirkus Reviews
Silicon Valley is the backdrop for this helpful book, written by a successful professional business adviser. Komisar's experiences have included working with LucasFilms, Apple, WebTV, TiVo, and Claris Corporation. Devoting himself to a handful of startup companies at a time for about a year or two, Komisar is regarded as a `Virtual CEO` who provides planning and decision-making advice and is not involved in day-to-day operations. Here, Komisar demonstrates his expertise through his conversations with potential entrepreneurs interested in starting an online funeral business. However, while the book does deal with the specific wheelings and dealings of Silicon Valley (such as the role of venture capitalists) Komisar for the most part offers the type of general advice that can be helpful for any entrepreneur. He mixes lofty opinions about business (`Business is one of the last remaining social institutions to help us manage and cope with change`) with practical advice (`Business conditions are forever changing. You need to reconsider your strategies and business models constantly and adjust them where necessary. But the big idea that your company pursues is the touchstone for these refinements`). One key issue that Komisar writes about is the danger of the `Deferred Life Plan,` where one is led to believe that you need to `do what you have to do` before you `do what you want to do.` As Komisar tries to explain, time is the only resource that matters, and what will make an entrepreneur truly successful is the ability to combine both the drive with the passion. The intriguing title refers to a February 1999 incident when Komisar encountered a monk in Burma, an incident that confirmedhisbelief that `the journey is the reward.` While perhaps not written for those interested in get-rich-quick schemes, Komisar's account provides enough business tips and Zen-like ideas to inspire would-be entrepreneurs.
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Product Details

  • ISBN-13: 9781578511402
  • Publisher: Harvard Business Review Press
  • Publication date: 4/1/2000
  • Pages: 192
  • Product dimensions: 6.02 (w) x 8.60 (h) x 0.78 (d)

Meet the Author

Randy Komisar is a Virtual CEO who has worked with companies such as WebTV and TiVo. He was CEO of LucasArts Entertainment and Crystal Dynamics, CFO of GO, and one of the founders of Claris Corporation.

Kent Lineback is a writer, producer, and consultant. He has produced seventeen film and video programs for Harvard Business School and is currently collaborating on a book about L.L. Bean and writing a screenplay.

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Read an Excerpt

Chapter One

The Pitch

"We're going to put the fun back into funerals."

    With that declaration, the meeting began. It was a curious elevator pitch.

    "The fun back into funerals?" I asked.

    "Absolutely. We're going to make it easy to make choices when someone dies. You know, the casket, the liner, flowers, that kind of thing."


    "Sure. All those decisions. It's not easy. So why not use the Internet?"

    "But fun? Why fun?"

    "Come on. Catchy marketing. You know, a play on words."

    "Ah, the fun in fun-erals."

    "Right. That's it. How many hits do you think you get now if you put the words `fun' and `funeral' into Yahoo!? Hundreds? I doubt it. You'll get one, just one. Us."

    Giving the pitch is a fellow named Lenny. Something about using the Internet to sell items most people buy at a funeral home when someone dies, items that arouse as many varied and complex feelings as sex toys.

    We are seated in the Konditorei, a comfy coffee shop nestled in bucolic Portola Valley. With the Santa Cruz Mountains to the west and Palo Alto and Route 280 to the east, we are but one exit away from Sand Hill Road, the famous home to Silicon Valley venture capital. The Konditorei is where I meet people like Lenny, the pitchmen of the Internet era. Here, or in a couple of restaurants in the same rustic strip mall. This is my office. (Forget Buck's Restaurant in next-doorWoodside. That's where venture capitalists prefer to meet supplicants and huddle around deals under a giant painting of Roy Rogers on Trigger rampant. If you sit in the corner of Buck's all morning, starting with the power breakfast crowd, you can quietly observe who is funding whom. It's a voyeur's embarrassment.)

    Every morning a stream of humanity stops at the Konditorei for coffee—joggers fueling up, businesspeople in a rush, Stanford students on their way to class, and a handful of deal makers en route from hillside homes to Sand Hill castles. It's also, ironically, a stop for the parade of incoming workers who saw, mow, paint, rake, and hammer away busily at the homes of the Valley shakers. Porsches, Mercedes, and BMW's queue up to enter the freeway, indifferent to the oncoming line of pickup trucks that replace them each morning.

    I had arrived a few minutes earlier, and Lenny was waiting for me.

    "You're Randy," he began. "I'm Lenny. Frank said you'd be easy to spot."

    Shaved head, cowboy boots, jeans, motorcycle jacket—I seldom get mistaken at these blind dates.

    With a solid grip, he shook my hand; then, his left hand on my elbow like a politician, he guided me to the table where he'd already set up shop. I could tell by his amped up confidence that he was probably not an engineer. Too outgoing. Too well dressed. So it's not a technology pitch, I said to myself.

    I looked at my watch on the arm he didn't have in a power lock. Nine o'clock exactly.

    "I hope I didn't keep you waiting," I said. "I had this down for nine."

    "Nine is right. Come on," he commanded. "I'll get you some coffee. My treat. You take cream, sugar?"

    "Thanks. I don't know what I'll have. Why don't you sit down while I decide."

    He started to resist, but I retrieved my arm and walked to the counter. He took one step to follow but then turned and sat down. I let out the breath I'd been holding since he grabbed my arm.

    I watched him askance as I waited for my low-fat chai latte, putting his age at twenty-eight. I took stock of his thick, blue-black hair and his pale and drawn face. He looked like he'd been pulling some all-nighters, and by noon he would need another shave. Beneath two smudges of eyebrows, his dark eyes gripped his target like his double-lock handshake—no gazing off and gathering his thoughts. He sat with his body coiled, tense, ready to spring. At me.

    Lenny's standard-issue corporate uniform—navy blue suit, crisp white shirt, tie a rich mosaic of reds and yellows—pegged him as not from the Valley: sales guy, I'd guess. The only one in the Konditorei wearing a suit and tie. Personally I hadn't worn a suit in years. When I was at GO Corporation a few years ago, spending several months negotiating an investment in the company by IBM, my opposite number was one of their seasoned negotiators, Dick Seymour. He was a classic IBM fixer. The equivalent of Foreign Service diplomats, these fixers knew how to manage both the internal IBM organization—all the different inside stakeholders whose interests could often be at odds—and the outside oddballs like us at GO. Seymour was probably in his fifties, fit, highly articulate, utterly professional, and impeccably dressed in a blue suit and crisp white shirt. There I was, in my thirties, in my jeans and T-shirt and florid socks and skateboard shoes, going nose to nose on complicated deal points. Dick treated me like a professional through all our wrangling, not as if I were a creature from a valley of lunatics. GO accepted some tough terms to get IBM's support, but I came away with nothing but admiration for Dick. He had class. He was the consummate deal guy. For all his professional savvy and maturity, though, I couldn't ever imagine a guy like Dick founding a startup.

    Now I'm wondering whether Lenny is the corporate type, just younger than Dick and not yet so polished and accomplished.

    Connie leaned over the register as she handed me my chai.

    "Your friend want another cup of coffee?" she asked.

    "I don't know. Sure. You know what he takes?"

    "You bet. French roast, black." She whispered, "He's had five cups in the last hour. I'm surprised he can sit still at all. I hope you're wearing your surge protector today." With her sleeves rolled up to handle the morning onslaught, Connie still had time to offer some neighborly advice.

    When I rejoined him at his table, Lenny glanced at the coffee I put in front of him and laid a black three-ring notebook in front of me. "Thanks" was obviously not in the script.

    "I usually make the presentation on a computer, you know, throw it up on a screen, if I can. That's how Frank saw it. But I checked it out earlier. Too much glare in here. So we'll use the dead tree version."

    Here it comes. The pitch. People present ideas for new businesses to me two or three times a week. If I chose to, I could hear a pitch every day—all day, every day. Just as everyone in L.A. has a screenplay, everyone in Silicon Valley has a business plan—most of them nowadays for Internet businesses. I've been around Silicon Valley and involved with young companies since the early '80s—startups, spinouts, spin-ins, what have you. I'm not in the phone book or listed in any professional directory. If you don't know someone I know, you can't find me.

    I wonder what Frank had in mind when he set me up with Lenny. I prefer to riff on ideas, brainstorm, prod and provoke, have some constructive give-and-take around a business concept. It didn't feel like there was going to be much of that with Lenny. I gazed out the picture window at the bright California day, the eucalyptus trees rustling in the breeze.

    "Before you get started, Lenny, tell me how you know Frank," I said.

    "He's, uh, a friend of a friend. We presented to him Monday, and he sounded interested. He wanted us to meet with you right away."

    Sounds like the early bird special, a quick chat before Frank and his partners hold their weekly gathering to talk shop and audition new deals. Obviously Lenny didn't know Frank at all. Thanks, Frank. You owe me.

    Frank is a headliner in the VC world, whom I've known since I raised money for GO. His firm is "top tier," a term reserved for firms with such a long wake of winners that the mere mention of their names imparts instant credibility and a whiff of inevitability to a startup. We stay in touch. A few days ago he'd called to say he was sending me a prospect. "Intense guy," he confided, "unusual idea but may be `interesting'. If you like it perhaps we can work together on this one."

    "What do you do, Lenny?"

    "I sell group life insurance to companies, part of the employee benefit package. National accounts. So I'm out to the West Coast every two or three weeks. I'm the company leader in new sales the last two years. Millions of dollars in value."

    Lenny paused a split second and slid some kind of legal document across the table.

    "I brought along an NDA. Could you please sign it before I go on." For a second his supreme confidence faltered.

    Without a glance, I pushed it back at Lenny.

    "I see dozens of companies each month, Lenny. I can't sign a confidentiality agreement. It exposes me to inadvertent liability. My integrity is my stock in trade. If Frank referred you, he can vouch for me. If you're uncomfortable with that, don't tell me anything you think is a trade secret. Frank didn't sign your NDA, did he?"

    "Ah, no. I just thought ..." Lenny said, skidding for a split second. "OK. Let me start."

    He flipped open the binder. It was a professional presentation, the kind you see in boardrooms all the time. From his pocket he extracted an extendable pointer. He pulled it out a few inches and tapped at the title page.

    "We want to call this business `,' but some undertaker in Oklahoma already has the URL," he said. "When we get funding we'll buy the rights to the name." Oh, brother. What next?

    "I understand," I said. Below the title were the date and the words "Presentation to Randy Komisar." He would probably read aloud all the words to me.

    "Presentation to Randy Komisar."

    "You don't need to read it to me, Lenny," I said. "Just tell me about it."

    "Sure, if that's what you'd prefer." He flipped to a page that proclaimed, in a blaze of black type: "The of the Funeral Goods Business."

    Now that's a new one.

    "This window of opportunity is going to close soon, but if we act now, we can make this the Amazon of the funeral business," Lenny began. "It's going to be big. The world is moving to the Internet—I'll explain that in a minute—and these products will move there too. The Internet's changing the way we live, and it will change the way people die. Someone's going to ride this opportunity all the way to the bank"—or the pearly gates, I said to myself—"and we think we should be the ones."

    Next page: "Projected Revenues."

    "In the first full year after we're up and running, we expect $10 million in revenue. Fifty million the second year. The third year we really hit our stride—100 million." Lenny paused for effect. "Exciting, right? It's big." He waited for my response, then leaned forward and whispered conspiratorially, "Most people don't like to talk about this. Death, dying. Loved ones passing on. But that's part of the opportunity. You understand that, right? It's a competitive barrier, a hurdle to entry. Most people won't want to do this. Would you?" He looked at me but didn't wait for an honest response. "I wouldn't, if I weren't so damn excited about it."

    Until this last line, Lenny's pitch sounded like dozens of others I've heard. Everyone's going to be the Amazon, or the Yahoo!, or the eBay of the you-fill-in-the-blank business. Manifest destiny. Millions—billions even—of dollars overnight. Then sell out, or do an IPO and cash out.

    "You know what makes this business so exciting?" he asked.

    I waited. The warm spring air wafted through the open doors of the Konditorei.

    "People are dying, that's what. It's inevitable. Death and taxes, right? Doesn't matter, rich or poor, what you believe, where you live, how you live, what you think. In the end, everybody has to die sometime, and we're going to be there, ready to provide the goods that people have to buy. They must buy! That's the point. You understand? This isn't about eyeballs visiting your site. These aren't eyeballs. These are people who need what has, because everybody dies. And when somebody dies, there has to be one final shopping day to assuage a life of guilt. To buy all these things, expensive things, high-margin things" — he thumped the table and stressed "things" every time he said it—"all these things, expensive things. And there's no getting around it. These are necessities aimed at the biggest aggregate market in the world—biggest because it includes everyone. Everyone." He paused again for effect. "That's the business, and it's a dream business, because you don't have to convince anybody they need what you have. They know it, brother, they know it. We sell the solution everyone ultimately wants. No demand creation, just redirect it, to us."

    I looked around the coffee shop sheepishly. Lenny should have asked everyone in the Konditorei to sign nondisclosure agreements. Sure, he might never see these people again, but these are my homies. Connie rolled her eyes. Having overheard so many pitches herself, she knew the drill cold.

    Next page: A shaded graph probably sold ready-made in any office superstore in the country. The shameless "Projected Growth" chart inevitably traces the outline of a hockey stick and assumes that a short period of investment will be obliterated by years of exponential increases in whatever—revenues, net income, profits, customers, corpses. Lenny's chart was all about revenues, certainly not profits, because this was, after all, an Internet business.

    "Hundred million, three years, easy." Lenny poked his pointer at the highest end of the graph. "Who knows how far it can go. The potential is unlimited, and in three years the exit strategy kicks in. May be an IPO. Depends on the stock market. Probably a buyout."

    "Getting to $100 million annual sales in three short years is no small task," I cautioned.

    I went on to explain that in the late '80s I'd been one of the founders of a software company, Claris Corporation, that grew to nearly a $90 million annual run rate in three years, and we were profitable to boot. That was when $90 million was $90 million, not like today when $90 million in stock options alone is chump change. I remember all too well how much hard work and good fortune must come together to make that happen.

    "Selling software? No offense, but what was that? Hundred dollars a pop? Two hundred? This is thousands of dollars a sale. Thousands. I'm talking about an order of magnitude difference. No comparison. Besides, the numbers here only include the U.S. You understand that? The U.S. alone. But, people die everywhere, right, not just here? This is truly global. The world market for these goods is at the very least triple, quadruple the U.S. market—tens of billions of dollars, easy."

    I pictured some Tibetan ordering the hack-into-small-pieces-and-feed-to-the-vultures economy option. How would Lenny price that?

    "Let me tell you something that I absolutely, positively, sincerely believe is the gospel truth." Lenny leaned forward and focused on me with his dark gaze. "You would have to convince me"—he tapped on his chest every time he said "me"—"convince me that these numbers are a stretch. A stretch? I don't think so. Listen, somebody's going to do this. No doubt about it. And I say, why not us? Why not us?"

    Lenny obviously didn't ask questions to get answers, and so I waited through his dramatic pause.

    "And I'm not alone in this." He flipped to a page of quotes from analysts and forecasters.

    He started to read the first aloud, from Jeff Bezos, founder of, something about "the migration of the $4 trillion global economy onto the Internet."

    I held up my hand so I could read in silence. In a world inhabited by people who think the Internet and the universe are converging, no shortage of proselytizers are willing to endorse any kind of cockamamie scheme as the next big thing. But Bezos deserved to be read. I noticed that he made no mention of funerals or caskets.

    "Have you been in a funeral home lately?" Lenny said suddenly.

    Well, no, I confessed, I hadn't.

    "Most people, they'd rather have a root canal. Research reveals that people think funeral homes are creepy places. Not good places for making decisions that can add up to the price of a small car. You're not there because something pleasant is happening in your life. You're there to see someone off, say good-bye. All the queasy questions you never ask yourself in daily life seem to be lurking in the next room, waiting to leap out and grab you by the throat. You know: What happens when you die? Is there life after death? Am I going to be called up next?"

    "If you could answer those questions on the Internet," I advised, "that would be a great business."

    "Oh, there are sites that claim to have the answers, but that's not what we're doing."

    Lenny would not be deterred, not with humor, not with questions, not with sidelong glances from strangers at the next table.

    "Then there's the guilt: You didn't call enough. You didn't stop in enough. You didn't help enough. Whatever you did, it wasn't enough. Now, by God, your dearly departed dad is going to have the casket of his dreams."

    He paused and glared at me, slightly indignant. Was I supposed to be the grieving fool about to spring for the most expensive casket or the conniving funeral director profiteering from human suffering?

    "Have you ever heard the pitch?"

    "Your pitch?"

    "No, no. The spiel you get in a funeral home."

    "No, I never have."

    He brightened. "All right, let me set it up for you. Imagine suddenly somebody's dead."

    Again, Lenny had everybody's attention.

    "Somebody important to you. You're in shock. Grief has you on your knees. But you're the one who has to make all the final arrangements. So, first, you have to figure out where to go. You've never done this before. It's all new. If you belong to a church or synagogue, you could ask the priest or rabbi. They would probably steer you to one or two homes—and it's not unknown, you know, for the funeral home to give the church a little something in return, by the way—and so you go there. Or you look up the Yellow Pages. Or an acquaintance says she knows somebody had a nice time over to Joe Blow's place. So, tears in your eyes because a light is gone from your life, you head over there. You figure they're all the same anyway, right? First thing, they say, `We're here to help you.' Help you? I doubt it. They're thinking when you walk through the door, before you walk through the door, about everything they can sell you. Cremation? Sure. How about a $12,000 casket? Let's burn that up too, show some respect. Oh, then there are sealed caskets. I love this. Buy one of those, just a few bucks more, so you can seal the old guy away from all that water and dirt underground. But when you seal it, the anaerobic bacteria can have a feast. Putrefaction sets in...."

    A little far, I thought, for an eating establishment. They'll never let me back in.

    "Lenny," I interrupted, "it doesn't make sense to go down this road. Just give me the conclusions." I didn't feel like hearing any more of the standard funeral home pitch.

    "Wait a minute," someone two tables over called out. "What about those anaerobic bacteria?" Connie shushed him.

    "But you've never heard the spiel," Lenny continued. "That's what you said."

    "I don't need the experience. Most of your customers won't have had the experience either. If your market is only people who've been suckered in their first funeral, that's not a ready market."

    He was undeterred. From his file he pulled out a four-color brochure and spread it in front of me. I suppressed a grin. Even if I did seem to be the sole focus of his sepulchral sell, I had to admire his spirit. He knew what he wanted, and nothing was going to stop him.

    I could more than relate to Lenny's single-minded sincerity. Years ago, when I was a young lawyer new to Silicon Valley, I represented a client in an arbitration hearing. Contrary to what you see in the movies or sensational TV trials, many legal proceedings are blandly cordial affairs conducted by lawyers who know each other socially, belong to the same private clubs, and break bread together. Trial histrionics can be as phony as professional wrestling. But I cared very little back then for the lawyer's code of civility. My job was to win for my client, and I was willing to do whatever that took, even if it irritated everybody else in the courtroom. I challenged nearly every one of my opponent's assertions and failed to show respect for my esteemed adversary, a friend of the arbitrator and, unbeknownst to me, a pillar of the local bar association. At the end of the hearing, my boss, the lead partner in the ease, turned to me shaking his head. "You're a lawyer's worst nightmare. A guy works all his life to rise above the fray, and you go for the jugular. You don t give a damn, you just want to win." He was bemused and dismayed at the same time. I suppose it's a privilege of youth to be admired and admonished by the wise guys who have gone before.

    Lenny pressed on. The brochure showed the latest fashions in caskets: metal caskets in pink and blue with matching satin lining, walnut caskets lined in white satin, and even some Greek sarcophagus-looking numbers. They all had model names, like cars: Peaceful Rest, Solitude, Heavenly Gates.

    "Is there one called Hand Basket?" I asked.

    "Hand Basket?"

    "As in `Go to hell in a hand basket'?"

    He didn't even blink.

    "Look at this. Look at this."

    He took out two pens and began writing—upside down so I could read what he wrote—dollar numbers next to each casket. It's a trick used by presenters to keep your attention while they write. So far Lenny had shown me his mastery of the Inevitable Growth Curve, and now the magic Upside-Down Writing Trick. Somewhere in his pitch, if I could wait long enough, Lenny would surely reduce the entire world to a four-cell matrix.

    Granted, Lenny struggled a little in writing the upside-down numbers, switching back and forth between red and black pens. He wrote two shaky but legible numbers by each casket.

    "The red number is the price typically charged by the funeral home," he said finally. Those numbers ranged anywhere from just under $1,000 to several thousand dollars.

    "The black number is the cost to the funeral home." Those numbers were all in the hundreds of dollars, some in the low hundreds.

    "The margins these guys get are unconscionable. Markups of thirteen, fourteen times cost. They get away with it because nobody feels like shopping around. Everybody thinks funerals have to cost thousands and thousands of dollars. But they don't."

    If no one felt like shopping around, I wondered what that meant for his business.

    "What margins are you taking?" I asked.

    "Good margins, but not rip-offs like many funeral homes. That's the opportunity. We can beat the funeral home prices and still make a tidy profit."

    "So this is a price-cutter's business. You're competing on price."

    He reached out again and flipped back a few pages.

    "Price, convenience, and information. It's the Information Age, and information is what sells on the Internet. We give you the information you need about the product in the quiet of your home. We'll do the price comparison shopping for you in every major city, eventually every city and town. Federal regulations require funeral homes to quote prices over the phone. You don't have to go in person. So we can call them all up and compare what they charge."

    He paused. "Sometimes they try to refuse, make it tough, imply you really have to drop by. Those are the sneaky ones I love to get. I used to blast them on the phone, ream 'em. Now I play along, let them refuse. Then I write the FTC and send a copy of the letter to the home. Afterwards, I call up and blast them, only now they got me and the FTC together, kind of a one-two punch, you know?"

    Nice business practice. Obviously, something about the funeral industry had gotten under Lenny's skin.

    "Pretty compelling, right?" he asked.

    One of the regulars at the next table smiled as he rose to leave, carefully folding the business section of The Merc and cradling it under his arm. "Very compelling, kid, can I invest?" He winked at me as he walked into the sunshine, offering what was probably the only bite Lenny had gotten on the fundraising trail.

    "How do you know people want to make these decisions on the Internet?" I asked.

    Lenny beamed. Here comes the Internet pitch, I realized just a second too late. He gathered himself and once again reached over and flipped several pages in the "Presentation to Randy Komisar" binder.

    "The Internet changes everything. Why drive to the bookstore to buy a book when you can order it from your couch and receive it FedEx the next day? Why buy airline tickets from your local travel agency when you can take control of your schedule and pricing on-line and accept your e-ticket at the gate? Why buy milk from the local market when you can check off a box on your screen and have it delivered by noon?"

    Lenny's rendition of the future made me feel like a prisoner in my own home. "Do you have a graph of Internet profits?" I asked.

    Lenny glared at me.

    It was a joke. Few Internet companies are willing to discuss profits, let alone produce them. No one knows what a piece of the Internet is really worth, or which economic models will ultimately produce profits, but everyone's betting their patch is rich bottom land, and they're willing to place their bets before anyone has shown they can grow much of anything on it. The market will eventually sort it all out, but the land grab is on.

    "You don't get it, do you?" Lenny said. "Let me explain."

    With that he launched into yet another rehearsed speech. Obviously he had developed micro pitch modules, and now I was getting the one on the current economics of the Internet, or the lack of them, and why the really smart companies were building brand and staking out territory, at the expense of profits. He said he'd never invest in a company that expected to make a profit in the near future on the Internet. Soon as they make a profit, they've fallen behind. It's growth or profits, etc., etc., etc. I wondered whether there could ever be enough day traders to keep these leaky boats afloat.

    While Lenny blasted on, I imagined myself standing outside the Konditorei, looking in through the picture window to see the Pitchman wind up for another inning and wondering how the other guy, me, managed to sit so still as the ball came toward him. My secret was counting my breaths—in, out, in, out—as I planned my escape.

    His idea was intriguing in some ways, but it was mostly just another plan for flogging merchandise on the Internet, and esoteric merchandise at that. It wasn't his intensity that irritated me. I expect that in people who found companies. They have to be a little irrational, passionate beyond analysis. If they don't believe in the face of doubt, they'll never make it. But Lenny was operating on automatic pilot set all the way to frantic. I d have to tell Frank that Lenny and I talked but we never really connected. Frank would have to come to his own conclusions.

    A cell phone rang. It wasn't mine—I don't own one. Lenny paused midsentence. For future reference, here was one way to interrupt his relentless pitch. It rang again. He opened his briefcase on the table, snatched out his phone, and snapped it open. "Lenny here," he said, as he strode out the door without a word to me.

    Rudeness is as good an excuse as any for an exit. I pulled my jacket off the back of my chair with one last look at Lenny's open briefcase. It revealed a stack of files, an assortment of pens, a family picture stuck on with a paper clip, an economy-size bottle of Pepto-Bismol, and some kind of homemade sandwich—tuna salad?—oozing around the edge of the plastic wrapper. Well, I thought, somebody loves him enough to make a sandwich. Or, maybe he's brown-bagging to save money.

    I told Connie I would be back later. She promised to hold my regular table. We both watched Lenny as he sat at one of the tables just outside the open door. Still oblivious to the possibility that someone might overhear, he argued and pleaded into the phone. "Wait! You didn't accept, did you? You said ... six months. No, one more month ... we made a commitment."

    "Sounds like trouble," Connie said to me.

    "Sounds like someone is bailing out," I said.

    "No, no, it's too important," Lenny yelped. "Remember what we said after my dad's funeral."

    "Aha!" Connie said. "Someone did die. I knew it!"

    "No, not a hundred," Lenny argued. "Komisar's only number twenty-six."

    "Well," Connie said. "twenty-six? You've moved up. You deserve a better table."

    "No, he loves it," Lenny said. "I can see ... he's in ... Frank ... fund it."

    "I get it," Connie said. "You're rushing home to get your checkbook, right?"

    Now I rolled my eyes.

    "Listen ... one more month. Just a month ... please. Please. Give me ..." He was still talking, but, to my surprise, his voice had downshifted, so we couldn't hear him, even as we both strained toward the door. He slumped, wordless, as though the wind had been knocked out of him.

    "Is he all right?" Connie whispered to me.

    He sat still, his head down, the phone dangling in his hand.

    I had to admit this was a different Lenny. For a second, I was a bit worried about him.

    Slowly, Lenny sat up and gathered himself. He put the phone back to his ear and spoke again. The words "two more weeks" were clear enough.

    "So, Mr. Last-Chance Twenty-six. You were leaving?" Connie wanted to know. She looked at me hard. "How about another thai?" she asked finally. "On the house."

    Perhaps this wasn't the most opportune moment to sneak out. I still had some time before my next meeting, and for all his bravado, this kid could really use a clue.

    I took my coat off. "My friend out there," I said, "he'd like a decaf."

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Table of Contents

Prologue: The Monk and the Riddle
1. The Pitch
2. The Rules of the Game
3. The Virtual CEO
4. The Deferred Life Plan
5. Romance, not Finance
6. The Big Idea
7. Beyond the Bottom Line
8. Who Will Lead?
9. The Gamble
10. The Whole Life Plan
Epilogue: The Road
About the Author
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Preface to the New Edition


It 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.

Don't be mistaken. Following your passion is not the same as following your bliss. While passion is a font of expressive, creative energy, it won't necessarily deliver pleasure and contentment at every moment. Success, even on your own terms, entails sacrifice and periods of very hard work. Following your passion will not necessarily make you rich, but then again it won't hurt your chances either, since most people are far more successful working at things they love. You have to engage passion realistically, with an eye toward what is achievable given your circumstances.

I have been delighted and gratified by the ardent response to the messages in The Monk. I heard from a young woman who had pursued the big payoff by working at a series of failed startups. The Monk reinforced her feeling that life is too short to spend it chasing elusive riches, and she left her job to try her hand at her passion, writing. A professor in Texas wrote and produced a marvelous short performance piece, a monologue, exploring the Deferred Life Plan. A number of entrepreneurs on the money-raising trail told me that after reading The Monk they had been emboldened to focus on the lasting value they wished to create rather than on their exit strategy. Many educators have included The Monk in their courses to encourage their students to think more holistically about their careers. And a few of the most respected venture capitalists let me know that The Monk captured the underlying passion and reason for doing what they do?the chance to turn ideas into viable enterprises that can change the world and to prosper in the process. I have also heard from people who agree wholeheartedly with the messages of The Monk but question whether they apply only to a select few privileged with substantial options regarding work and career. Surely things are different for an underskilled single mother of three barely scraping by on minimum wage. But even so there are people who tell me that The Monk has inspired them to improve their circumstances?to find jobs that are more consistent with their interests and values, to learn new skills that provide satisfaction and growth, to reach for more rewarding opportunities and engaging challenges.

I am reminded that finding meaning and fulfillment in one's work should not be an elitist notion. A few readers were disappointed that The Monk never attempts to address specifically how to create a successful business. I don't have a prescription for financial success, nor do I think one exists. In truth, The Monk is not primarily a business book; that is, it is not about buying low and selling high, but rather about creating a life while making a living. It is about the need to fashion a meaningful existence that engages you in the time and place in which you find yourself. It is about the purpose of work and the integration of what one does with what one believes. The Monk is not about how, but about why.

Since The Monk was published, I have ridden my bicycle across the extremely challenging Himalayan landscape of Bhutan, a country that measures its prosperity by Gross National Happiness rather than Gross National Product. Things are different there. The volume is turned down; the clock, slowed. The pace of life is gentle. Fancy things are few and far between, but those precious qualities of life that seem to vanish in a Western society intent on measuring everything are not forgotten in Bhutan.

It was a gorgeous adventure. As I am wont to do, I spent some time visiting several Tibetan-style Buddhist monasteries that are home to communities of friendly monks in crimson robes. At one point, I had the rare privilege of an audience with a distinguished eighty-year-old lama who practiced the art of medicinal Buddhism. His nephew made the introduction and interpreted for us.

Two friends and I sat in a semicircle at the foot of the lama's raised platform. The temple was dark, streaked with smoky light that gave the room a mystical air. Behind us was an altar of large sitting Buddhas. Yak butter lamps sputtered in the foreground. The main walls were covered in beautiful paintings detailing Buddha's life and the introduction of Buddhism to Bhutan by Guru Rimpoche some 1,300 years ago. Many of the images were Tantric, depicting the struggling union of wisdom and compassion in the orgasmic joining of man and woman. The paintings were covered by colorful wall hangings to protect them from the elements and untrained minds.

Elephant tusks arced heavenward at the corners of the altar, a reference to the crucial role of the white elephant in the birth of the Buddha. Before us sat this lovely old lama. A few days' growth on his chin and head, he constantly stroked his scalp, luxuriating in the feel. His teeth were obviously not all there, and he scrunched his lower jaw in the fashion of an old man who has forgotten his dentures. His once-white long johns showed under his heavy robe, insulating him from the early-morning chill. Behind him, the light penetrated through the filthy old windows that looked out fourteen thousand feet over the valley and beyond. All around the windows were piles and piles of bright red chilies?hot chilies?to warm the Bhutanese bellies and hide the blandness of their cuisine. Each member of my party was permitted to ask the lama one question. I would come last. As each query was made in turn, I used the time to come up with a question worthy of such an eminence. What could I possibly ask that would not embarrass me by its triviality? How could I tap this holy man's wisdom?

Finally it was my turn. The lama looked down at me with compassion and perhaps a little boredom. His nephew stared at me imploringly. I sat, quiet. After a long moment, I asked softly, "Your holiness, with your great age, experience, and wisdom you have encountered many things. You have certainly answered many questions. What question still perplexes you? When you sit in meditation, what question do you still ask yourself?" The lama's nephew wrinkled his brow and haltingly translated my question. He launched into an explanation far lengthier than my own while the old lama nodded, peering occasionally in my direction. I feared I might have crossed a boundary, perhaps offended him. But after an instant of contemplation, the old lama turned to me and fixed his eyes on mine. Then he spoke gently, and ended with the lilt of a question in his indecipherable Bhutanese. He continued to stare into me as his nephew said simply, "The lama says he still doesn't understand why people are not kinder to each other." That was it. We got up slowly, made our bows, and climbed down the steep ladder to the dark, cold living quarters and the walled open-air courtyard.

As we entered into the bright morning light, we could see the clouds dispersing from the valley. The young monks went about their business, sweeping the grounds and cleaning the morning dishes, smiling at us whenever we caught their eyes. As we left the compound and started down the mountain, we turned to see the old lama staring at us and waving from his dirty, chili-festooned windows, still fondling his scratchy scalp and munching down on his toothless jaw. Another monk, another riddle. And, as with The Monk and the Riddle, the answer lies not in dollars and cents, but in who we are and what we believe.

Randy Komisar,

March 2001

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Interviews & Essays

Randy Komisar, the Author Interview
April 2000

Ever since venture capitalist superstar John Doerr began offering public kudos to Randy Komisar's The Monk and the Riddle, the buzz surrounding this new Silicon Valley business narrative has been getting louder. Our business editor recently interviewed Komisar about the message behind the monk. I knew your book was getting a lot of prepublication buzz when people were trying to steal my early copy. That's always a good sign.

Randy Komisar: When you start one of these things -- and I started this book a year and a half ago -- you don't know where it's going to go and what world it's finally going to come out in. It seems to be timed well with a sense of introspection about what's going on in Silicon Valley. How did the book originally come about?

Randy Komisar: Hollis Heimbouch, my editor, called me up one day. I didn't know her. She asked if I'd ever consider writing a book. Of course, in the back of my mind, I always considered writing a book but I always thought it would be a novel or something. I hadn't considered writing a business book. I wasn't interested because I only knew of two types of business books: The how-to books and the ego books. And I didn't feel comfortable wtih either one of them. So my answer was no. The nature of what I do suggests that there is no "how to" other than to really have a strong sense of who you are. There aren't 200 pages on that. And an ego book is just inconsistent with the way I think of myself. So when I pushed back on her and said, "Yeah, maybe I would write a book but but it would have to be something like this," she was receptive. I was shocked because there's real precedent for this type of book. That's really true. In all of other books that have been written about the Silicon Valley business world, you don't come away from it knowing the author loves dogs, Merlot, and traveling and has a passion for passionate business ideas.

Randy Komisar: The notion of what I was trying to do in the book has to do with the fact that I'm a great reader of travel books. And in the mid '70s, travel writing changed with Theroux and Chatwin and a few others who made travel books less about place and more about the people and characters in those places. What I wanted to do with a business book was write less about the business and more about the characters and people within business. So my very ambitious goal was to do something similar to what Chatwin and Theroux did early on. God knows we didn't come close to it. But, I wanted business to be the milieu rather than the focus. It feels like part memoir, part career guide, part Valley sociological study, and part leadership guide. If you had to pigeonhole it into a genre, where in a bricks and mortar B&N would you shelve this thing?

Randy Komisar: My answer to that is the same answer about myself. I use the moniker "Virtual CEO" because it is meaningless. It forces people to have to deal with me for whom I am. My feeling about this book is if you put it in a genre, you don't do it justice. I"d love to see it sprinkled around bookstores so that people interested in travel and life and business would all be able to come across it. It was never intended to fit cleanly in to a genre. That's both a strength and a weakness -- weakness in terms of marketing it easily, and a strength in terms of its read. You say that what you love about your work is the "blank piece of paper" phenomenon. Explain what that means and what it can mean to your readers both inside and outside of the high-tech industry?

Randy Komisar: For me it means to take a look at whatever situation I'm in, whatever opportunity is in front of me, and to see it as a clean set of choices, rather than meet it with some set of expectations that don't allow me to understand it for what it is. In the context of any business situation, that means being able to work a great idea into a viable business that can have impact. The centerpiece of this narrative is your mentoring the aspiring e-commerce entrepreneur, Lenny. Is Lenny an amalgamation of all the naive start-up dreamers you've encountered in the Valley?

Randy Komisar: He's both an amalgam of people that I've come across and also a reflection of parts of me. The education of Lenny is my education. Lenny is an extreme character because I wanted to bring a lot of these issues out in the course of 200 pages. But a lot of what's in Lenny, I've confronted in myself over my career. You can look at that conversation with Lenny as my conversation with myself, to some extent. When you're explaining your work with Steve Perlman at WebTV, you describe the very overwhelming (almost paralyzing) moment when you both realized what an enormously high-impact idea you were embarking on. You even liken that moment to a scene from the horror movie "The Shining." How did you cope with the magnitude of that work and so many other major projects that you've been involved with, from your time at Apple to working with George Lucas?

Randy Komisar: That's a tough one. In part, it's about being clear about what the touchstones are for you and for the business and having a very clear set of priorities. Both in terms of the execution at the business level and on the personal level. You can't allow yourself to get caught up in the whirlwind and myopic. Keep yourself slightly detached, slightly objective, so you are alert to the fallacies and the changes that you need to cope with. That's a real skill that is very very difficult to keep honed, but it's very important in the start-up world. I was recently talking to Donna Dubinsky, the founder of Palm [Computing] and now Handspring. She was saying that she adopted a child as a single mother and started the business. She tries to keep a relatively balanced life because she feels that putting all of her time and energy into her work won't make her better at it. It won't allow her to be as creative or incisive as she needs to be. So some level of detachment rather than total immersion makes you more effective. Another part of that detachment is knowing when to depart a company. In your career, you've done that pretty frequently and embraced the constant changes.

Randy Komisar: I'm always saying goodbye. You'd be surprised how many of those goodbyes are more like au revoirs. The reality is I'm never totally disappearing. I'm always a phone call away. And every single company still contacts me. Some infrequently and some more frequently, even though I'm no longer officially attached to those companies. But, as you point out in the book, there are complications for leaders when it comes to knowing when to stay and when to go. You point out that a Silicon Valley startup really needs three different CEOs for the three different phrases that it will go through. This concept is still pretty foreign, and difficult, for leaders in mainstream industries.

Randy Komisar: Outside of the technology industry, it may not be exactly the three-leader format, but just the basic notion of recognizing the different elements of leadership and how they apply to your business at any single moment. I think understanding that can lead you to think about structuring the leadership role so that it's sharing with a set of individuals. These are questions that I tend to see addressed more logistically in large companies than strategically. Part of the reason for that is, leaders often think of themselves as kings of a fiefdom rather than as a component of the overall leadership structure. It's threatening to people when they are in that CEO role to admit to themselves and certainly to admit to their organizations that they are not complete. You see people like Eisner and others who sort of resist bringing on additional leadership talent. And it is threatening because most of the emperors know that they're not fully clothed. So this idea does apply to large organizations as well as to small start-ups. That reminds me of the portion of THE MONK AND THE RIDDLE where you're describe seeing Rembrandt's painting of "elaborately attired" movers and shakers of Holland's economic golden age, and you liken them to the champions of todays economic boom by saying "Think about The Night Watch today, when so many people push and shove with their wealth, fame and power. In a few hundred years, all of today's movers and shakers may be reduced, at best, to another group of supporting characters on a canvas." Could you elaborate on that a bit?

Randy Komisar: This book has many levels, but the overarching theme of it is that time is all that matters. We can look at tactical issues about how to put together a start-up. We can look at complicated issues about how to balance and integrate your work life and your personal life. But principally, what puts all of it in perspective is time. And once time becomes the most important factor in deciding the things that you do and how you live your life, you live your life differently. You realize that Sam Walton died the richest man in the world, and it didn't matter to Sam, because he died. Ultimately, once you come to grips with that, hopefully you begin to think differently about what's important. For me, when I sat in front of The Night Watch, it just became so apparent to me that I was looking at the movers and shakers of Silicon Valley 300 of 400 years ago. I didn't know any of them. They didn't matter. I'm sure they mattered to their families, and there may be some small business or heirloom that they're still remembered for, but [compare them to] Rembrandt. Rembrandt was penniless, but he had a way of expressing what he saw around that makes him everlasting. He's eternal in those paintings and those people are not. So, from my standpoint what I'm trying to do with that little piece is to give everybody a bit of a nudge and a bit of a wake-up call and say, "Let's get real about what's important here. I think it's great to have money. But it's what you do with it and how you get it that's important."

About the Author

Randy Komisar is a "Virtual CEO" who has worked with companies such as WebTV and TiVo. He was CEO of LucasArts Entertainment and Crystal Dynamics, CFO of GO, and one of the founders of Claris Corporation.

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  • Anonymous

    Posted April 30, 2000

    An extraordinary work

    This book makes you laugh. It makes you want to cry. But most important, it makes you stop and think. I am recommending 'The Monk and The Riddle' to everyone I know who hopes to succeed in the emerging business climate.---Bruce Judson, Author, 'NetMarketing' and 'HyperWars'

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  • Anonymous

    Posted April 7, 2000


    This book is so inspirational!

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  • Anonymous

    Posted August 31, 2009

    No text was provided for this review.

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