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

by Randy Komisar

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)

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.

No matter how hard we work or how smart we are, our financial success is ultimately dependent on circumstances outside our control.

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.

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.

I am reminded that finding meaning and fulfillment in one's work should not be an elitist notion.

the answer lies not in dollars and cents, but in who we are and what we believe.

I admire people who are willing to bet everything on a belief. Some of these risk takers, whether immigrants or entrepreneurs, have a profound impact on what happens in the world. They place bets on the future, often against fantastic odds. I see heroism in that.

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?

But how would he react when reality swept over his PowerPoint slides?

in a Brave New World startup, where there's no existing market, no incumbent competitors, and no economic model, you're literally inventing the business as you go along. It was absurd, I told him, to hold the team to the original plan.

“Lenny,” I said, “I doubt your plan will take you all the way. There are too many unknowns. You'll need people capable of navigating without street signs. The composition and experience of the team are something VCs will look at hard.” 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 capable 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 the fly. Refine the strategy, maybe even radically. This team 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.

Venture capital firms have a great business—the investment business. They bring in money from limited partners, and it's their job to give back to those limited partners a return that reflects the risk taken with that money and exceeds what they are likely to get from other investments. For that effort, the VC gets a fee and a carry, a percent of the deals gratis.

With frenetic energy and a natural penchant for risk taking, these armies of prospectors are smart, hardworking, and aggressive. They do bring connections and contacts to the aid of the companies they fund, in addition to money. Often stereotyped as “vulture” capitalists who drive expensive cars, drink pricey wines, collect extravagant toys, and wish they had the time to indulge in their expensive hobbies, they are reminiscent of Wall Street masters of the universe, or L.A. players—except for one thing: their bets build the future in remarkably tangible ways. While their N.Y. and L.A. counterparts feast on marbled steaks from the corner butcher, VCs birth, fatten, and butcher their own steers before the barbecue. Take them out of the picture, and the Valley and its financial boom collapse. A few of the venture capital firms are beginning to recognize the limitations of the current “stretched thin” situation, and there are, of course, some notable exceptions to the present trend. Regardless of the amount of attention they can spend on any single company, they are still some of the heroes of the new economy.

for a large valuation so he could raise his financing by selling the smallest percentage of the company possible, thus maximizing his ownership. The Valley calls that minimizing “dilution.”

I had to explain. Valuation is all about risk and reward. Sure, $50 million is a sizable business, but what are the chances for failure or delay? And how much money would he ultimately need to be successful? Future dilution would have to be figured in the mix. The lead VC is more likely to want around 40 percent of the deal for his money at this stage. If Lenny were to raise $5 million, 40 percent would mean that the post-money valuation, the value of the company plus the new money, would be more like $12.5 million. Subtract the investment, and you have a $7.5 million pre-money valuation, the implied value of the business. Nowhere near the $25 million Lenny was suggesting. Everybody here brags about valuation, but Silicon Valley really operates on momentum. Many times I caution a company not to take the largest valuation they can in a financing, because it sets the wrong expectations and probably attracts the wrong investors. Peg the round at the highest reasonable price necessary to raise the desired amount from the right investors. The right investors bring credibility, experience, and networks. They support you with enthusiasm in later rounds. They raise your valuation merely by their presence in the deal.

The right amount to raise is a range with a minimum, but seldom a relevant maximum. In a fiery market like ours, raise enough for a year's burn rate, or net loss, assuming the worst. Then add on enough for another six months, and take anything reasonably offered above that. I have never seen a company fail for having too much money. Dilution is nominal, but running out of money is terminal. Set reasonable expectations among your investors, don't gouge them, and then out-perform expectations. Future rounds will be much easier if you are seen as having positive momentum.

SOME PEOPLE CALL ME AN ANGEL. In the world of startups, angels invest in seed or early-stage deals, and with their money they lend a bit of advice. They pay for the privilege of helping the company. But I'm no angel.

I explained to Lenny what I do: I incubate startups. To that end, I provide the scarcest commodity of all, leadership and experience. I help the people build their ideas into successful businesses. Neither an angel nor a consultant, I support entrepreneurs as a kind of junior partner, a full member of the team, an owner and a decision maker, not a hired hand. I invest my time, and, in return, I receive an equity stake in the business. With that stake, I think like a team member, and sink or swim with the founders. Some people call me a virtual CEO.

The title stuck. I started working with a handful of companies at a time. I generally devote myself to each for a year, perhaps two. In that period we should be able to raise money, develop the product or service, identify the market, create a business model, prove out its basic tenets, and hire an operating team. With that team in place, I retreat to an advisory capacity and give more hands-on attention to the next startup. My specific work in each of the companies depends on the backgrounds of the founders and the particulars of the business. My work is improvisational. Though involved in all the planning and major decision making, I don't play any day-today operating role. On the org chart I'm a bubble around the management team. Startups require frenetic execution and relentless perseverance. My role is to keep my head out of the cyclone and provide insight, direction, and stability. I try to bring to each company the experience I've gained—raising money, setting strategy, building and leading teams, establishing strategic relationships, developing products and services and bringing them to market, doing deals. And I make available to the startup all my contacts in the industry. Good entrepreneurs are passionate visionaries, usually with one or more exceptional talents, but rarely have they actually built a company from scratch. I fill in the gaps in their experience. The actual CEO is ultimately responsible for all the company decisions. As a Virtual CEO, I simply pro...

“Not at all. I never tell anyone to quit,” I said. “I may not want to be involved, or I may think your idea is likely to break your heart and your bank account, but I never say quit.”

Fill each startup with rocket fuel as fast as possible and blast it into space. The ones that fly, fly, and if the rest of them blow up, c'est la vie.

You have to 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 after all, we won't have wasted truckloads of money.

business isn't primarily a financial institution. It's a creative institution. Like painting and sculpting, business can be a venue for personal expression and artistry, at its heart more like a canvas than a spreadsheet.

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

Business, however, has a tendency to become tainted with the greed and aggressiveness that at its best it channels into productivity. Left to its single-minded pseudo-Darwinian devices, it may never deliver the social benefits that the other fading institutions once promised. But, rather than give up on business, I look to it as a way, indirectly, of improving things for many, not just a lucky few. I accept its limitations and look for opportunities to use it positively. In the U.S., the rules of business are like the laws of physics, neither inherently good nor evil, to be applied as you may. You decide whether your business is constructive or destructive. I help people understand this and express themselves in what they do, trying to make a difference through business.

What looks like a cloud to one person is a chance to sell umbrellas to the next.

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.

If, after careful consideration, he were to pursue a business he truly cared about—well, that would have been understandable—but reflexively hopping back on the carousel seemed like a waste. I could only hope that with a little more time, he would rethink things.

No, I explain, my heart was in everything, in all of it together. My Providence was this: What started as a way to fill time and pay my way while I figured out what career to pursue turned into something unexpectedly rich and fulfilling. But it wasn't any one single part of this life that excited me. It was the aggregate. All the pieces fitting together gave me satisfaction and energy. I was passionate about the whole: No one particular part attracted me to the exclusion of everything else. Each part excited me fully while I was doing it, for the moment I was doing it. My passion was for exploring everything. I was beginning to see how creativity could thrive in the context of earning a living.

never doubted Lenny's drive. It was obvious from the very beginning, even in the armlock he laid on me at the door of the Konditorei. Drive, commitment—those weren't my concern. I wanted to know what he really cared about. I wanted to know his passion. Lenny didn't seem to understand the question. He was beginning to nettle me.

So why were they doing this? Why was it worth their time? I am always amazed that venture capitalists don't ask that question.

It is too easy to get lost in the hype and swallowed up by the casino economics of it all. It bothered me to see talented young people give up, or defer, their ideals in the hope of a fast buck that was unlikely to ever arrive.

As he already pointed out, the one thing we can count on is change. But knowing what we require to be willing to do something lifelong provides invaluable self-knowledge.

It's not, as I've learned from my own experience, that the deferred life is just a bad bet. Its very structure—first, step one, do what you must; then, step two, do what you want—implies that what we must do is necessarily different from what we want to do. Why is that the case? In the Deferred Life Plan, the second step, the life we defer, cannot exist, does not deserve to exist, without first doing something unsatisfying. We'll get to the good stuff later. In the first step we earn, financially and psychologically, the second step. Don't misunderstand my skepticism. Sacrifice and compromise are integral parts of any life, even a life well lived. But why not do hard work because it is meaningful, not simply to get it over with in order to move on to the next thing?

The Deferred Life Plan also dictates that we divorce who we are and what we care about from what we do in that first step. By distancing the real person from her actions, all manner of bad behavior is justified in the name of business. “Sure she's an SOB at work, but that's not who she really is. It's only business, nothing personal.” Fueled by ambition, we hope that in the end we will be judged by our accomplishments, not by who we are. Silicon Valley is a ...

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 a modicum of self-knowledge, you can express your passion. But it isn't just the desire to achieve some goal or payoff, and it's not about quotas or bonuses or cashing out. It's not about jumping through someone else's hoops. That's drive. In the Deferred Life Plan, drive pushes us through the first step. The second step, the deferred life itself, is the home of passion. We hope and suppose that when we get there, we will be able to resurrect our passions on our own terms. If we get there.

I had passion in Providence but didn't appreciate it. I drove myself through law school and the practice of law, seeking and hoping and groping for passion but never finding it. Then in Silicon Valley—at Apple, Claris, GO, LucasArts—I discovered passion in my work. But I didn't understand the crucial difference between drive and passion until I found them at war inside me.

My instincts, reinforced by my experience at LucasArts, said we should take a step backward and do this right: Cut back the sales side of the business, and retreat to the core of the company—the creative organization. Focus all our resources on developing a small number of high-quality games. Sell these games through outside publishers. Then, when we had a stable of successful titles, rebuild Crystal's own sales organization, and recapture the control and margin given up to the distribution partners. We would likely wind up in the same place sought by the founders, but by a different route and with less risk at each step.

Crystal was not a place I could see myself working the rest of my life. That meant I needed to get out, now.

Don't confuse drive and passion. Drive pushes you forward. It's a duty, an obligation. Passion pulls you. It's the sense of connection you feel when the work you do expresses who you are. Only passion will get you through the tough times.

it's the romance, not the finance that makes business worth pursuing.

Good management must remind people constantly to ignore the jerking and lurching of the market and focus on the horizon. Stay.com.

The chance to work on a big idea is a powerful reason for people to be passionate and committed. The big idea is the glue that connects with their passion and binds them to the mission of an organization. For people to be great, to accomplish the impossible, they need inspiration more than financial incentive.

Impatience wasn't Allison's problem. Finding something in Funerals.com to care about was.

Sculley's Apple subordinated the company's big idea to the business model. That model was not the essence of Apple. It was simply that moment's best means of realizing value from the big idea. The business model can and should change over time, as the world changes. Ultimately, when the big idea was lost, the market and Apple's employees could no longer find a reason to support Apple's business. Their fanaticism faded to ambivalence. I was curious about whether Lenny was following the example of Sculley's Apple even before he'd been able to start the business. Was he selling the business model rather than the big idea—whatever it was—that had attracted Allison and him to Funerals.com in the beginning?

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. Ditching the big idea in order to deal with business exigencies leaves you without a compass. I always advise companies to define their business in terms of where it's going, what it's becoming, not simply where it is. Set the compass, then work hard to clear a path, knowing that you may meander as you stumble upon obstacles but will always keep heading toward the same coordinates.

“Al, I'm not saying we will never do what you want,” he offered finally, in what sounded like a closing. “I think we can do it eventually, but I don't believe we can get funded by promoting a business aimed first and foremost at helping people. We have to focus on products, revenue, growth, profits. Your ideas are too squishy. You see this utopia, this company with no structure and a bunch of eager beavers who work for the love of it. What you want is unrealistic. If we win on the bottom line, then we can consider new ideas and directions. Hey, if we're a big success we can even endow a foundation to deal with the virtuous, people aspect of death and dying.”

“Besides,” Allison continued, “I'm not interested in funding a service. I want to spend my time being involved. I want to work in an organization that cares about people in trouble, that”—she waved her arm—“that cares about people, period. This is a chance to change what we don't like.” She paused for a moment. “And you're right. I want to build a legacy company, a place we can be proud of, where people work hard, and care about what they do and respect each other. I want a place I can believe in, in every way—what it does, what it stands for, how it works. I don't want to wait for my ship to come in before I can afford to start. Why wait when we can do it now?”