The Monk and the Riddle: The Art of Creating a Life While Making a Living (9 page)

I
ARRIVED BACK HOME LATE
that evening after dinner with some old friends at the Iberia, another of my local spots. It was a bit of a “My Dinner with André” gathering. We postulated, between the paella and a few bottles of Spanish wine, on just how high the market could go and wondered whether there would be a bottom if things deteriorated. By my second glass, I was holding forth on the metaphysics of business, the human and social dimensions of commerce. My companions—all variously involved in the Valley as founders, funders, or functionaries—had heard this bit so many times, they just nodded in faint agreement and tried to steer the conversation back to the practicalities of buying low and selling high.

My afternoon had divided neatly into two parts: First back at the Konditorei for another pitch from a group of upstarts proposing to use the Net to improve customer service, retention, and recovery. Then a board meeting at which, depending on how you wanted to look at it, we wrestled with an impending cash crunch or we readied the company for a public offering. What looks like a cloud to one person is a chance to sell umbrellas to the next.

My wife, already off to bed, had left a light on. Debra is a high-powered senior executive at Hewlett-Packard, now one of the Valley's most venerable companies, decades beyond its scrappy start. Tika and Tali, our more-or-less Rhodesian Ridgebacks, shoved their muzzles through the door as I opened it, their tails drumming the wall in unison.

I ditched my boots, poured myself a Calvados, and headed to my office for the final task of the day: clearing phone messages and e-mails. Through the window, the distant lights of San Francisco twinkled like the Milky Way.

A sandy-haired, softening, former fraternity boy out of UCLA, Frank is a genuinely nice guy. But his easy affability hides a fierce competitive streak. On the brink of forty, he's been in the business for more than a decade. He knows as well as anyone that it is important first to evaluate every aspect of a new idea with analytical precision but that, in the end, the decision to fund or move on is a matter of instinct. Frank can apply all the right metrics, but it is his nose that gives him his edge. He has a deep respect for entrepreneurs, coupled with a no-nonsense attitude toward performance. He would pull his support in an instant if he felt a founder wasn't cutting it.

Until Frank's note, though, my morning with Lenny had become a distant memory. Funeral goods. Bacteria. Make it big, then cash out.

I hit “Reply” and tapped out an answer:

I looked the note over. I wanted to be honest and fair. Lenny was hard to read. His drive and desire were plain to see, and he had the makings of a good promoter, but something was missing.

Yawning, I hit “Send” and then deleted Frank's e-mail. Case closed.

I worked through the remaining messages one by one— FYIs from some of the companies I work with, a few queries from friends of friends suggesting we meet to discuss new ideas, and one from my sister the accupuncturist in Boston letting me in on a new herbal remedy. Then an e-mail from Lenny. I noted the time; he'd sent it well after midnight in Boston.

I replied:

I finished off the remaining three e-mails and thought, finally, I was done for the day. Then a ping—a reply from Lenny. I looked at my watch. It was almost 3:00 A.M. in Boston. The guy must not sleep.

I had indeed pegged Lenny as a greedy opportunist, but I hadn't expected, in the heat of all his bluster, that he was astute enough to register my impatience. Curiosity overpowered sleepiness. What the heck—I checked out his URL.

Adorned with digitized Polaroids of parents and siblings, Lenny's Web site took me back to the early days and all the commotion over the vast and messy democratizing eloquence of the Net. Every voice and community would have a place in cyberspace. The Web would foster paeans to the special talents of the family hamster, hipper-than-thou e-zines run by semiotics students, and gritty neighborhood joints for all manner of hobbyist. Shoot the middleman, free the masses.

All these highly charged, highly personal sites left you feeling a little strange at first, as though you were picking through the effects of another's life, peeking at someone's diary. I felt the same way looking at Lenny's site, even though he had invited me.

Lenny had quite a family—three brothers and a sister— each lovingly accounted for with pictures commemorating major life events: grammar school with its annual, grainy head shots; Scouts; the goofy haircuts of the seventies; high school proms; weddings; cheery toddlers with arms outstretched toward the camera. Nothing special here—just another family with its intimate history frozen in an uncomfortably public way.

About to call it a night, I noticed another picture. The characteristic black hair gave away the man's identity-Lenny's father, Jack Dolan.

Clicking on the photo opened a memorial site for Lenny's father, who had died almost eight months earlier. I recalled what Lenny had told me in the Konditorei. There were more family photos—Jack with each of his children and his wife—some pages of text, and, under the heading “At Play,” a group of pictures showing Jack Dolan working in a garden that was a riot of color. One photo showed him standing by a stretch of forsythia. Another showed him with spade and hoe, crouched over a flower bed, planting seeds in this suburban Eden. He was always smiling, hands working the earth in front of a small, one-family Cape Cod. Every corner and window was festooned with flowers like some intricately designed English garden. This house must have been the neighborhood attraction. Under the heading — “Taking Care of Business” — I came across a few more photos: Jack Dolan posed soberly behind a tidy desk or engaged in serious-looking work, his dark jacket framing a white shirt and a quiet tie. He was described variously as a “dedicated public servant” and a “faithful friend of the Commonwealth”—by the Governor, no less—and commended for more than forty years of service on his retirement, which the dates showed came less than a year before his death.

Connie's prescience scored again: she had rightly guessed that someone's death had given birth to Funerals.com. Jack's demise, so soon after retirement, and Lenny's decision to break out of his nine-to-five and go for the pot of gold at the end of the startup were probably not unrelated. Whatever Jack's true interests, it was clear from Lenny's site that he saw his father as a frustrated gardener, not a happy bureaucrat.

No question: Lenny was his father's son, taking care of business first. In what I presumed was Lenny's wish to avoid his father's fate, he had subjected himself to the same unforgiving compromise. There's no official name for it, but given his background in insurance, Lenny might call it the “Deferred Life Plan.” For the promise of full coverage under the plan, you must divide your life into two distinct parts:

Step one: Do what you have to do.

Then, eventually—

Step two: Do what you want to do.

We hear variations on this theme from childhood on:
Walk before you run. No peas, no pie. Pay your dues.
Or, perhaps in the case of Jack Dolan, as Lenny saw him, work,
then
retire —assuming you live long enough to retire — and then devote your time to your passion.

The Deferred Life Plan certainly dominates Silicon Valley. Most people think getting rich fast provides the quickest way to get past the first step — and where can you get rich faster than Silicon Valley? The problem is that, despite the undisguised affluence, the verdant hills, and media-generated mythos, the vast majority of people in Silicon Valley will not get rich. Most business ideas do not find funding. Even the majority of those that are funded—that is, vetted by very smart people who think enough of the ideas to invest in them — ultimately fail. And the lucky winners may get to step two only to find themselves aimless, directionless. Either they never knew what they “really” wanted to do or they've spent so much time in the first step and invested so much psychic capital that they're completely lost without it.