On Airline Crashes and Becoming CEO of a Start-up…

I hate reading about airplane accidents. I know that statistically planes are safer than cars, but I fly often these days and stare out the windows on take off and decide to trust laws of physics and ignore the vagaries of life involving hung over pilots, underappreciated maintenance workers, and metal fatigue…

When there is an accident, particularly a deadly and tragic accident like last week’s Tesla motors Cessna crash, I am unnerved. I’ve watched numerous documentaries and news reports about airline crashes – and the same story repeats itself. It goes like this:

"Accidents occur when a chain of unfortunate events all line up exactly right," said Paul Weihs, an FAA Safety Team representative for the San Jose region, whose company, Aviation Training Curriculum, teaches pilot safety at local airports. "One thing rarely causes a crash. But when you line them up, something is going to happen."

Crashes are totally improbable. There are systems, and backup systems, and the odds of a random set of bad things lining up in just the wrong way are astronomical. But apparently, it happens. Try as we might, you just can’t protect from every odd permutation of events that can lead to a crash. According to flight statistics, the odds of being killed in a plane crash are somewhere between 1 in a million and 1 in 10 million, depending on airplane and airline…

Now that I’m leading a start-up company, I’m beginning to imagine another completely improbable event: utter success. From another body of research, the likelihood of a start-up company becoming an “out-of-the-park” success is also about 1 in a million. Most start-ups fail. Survivorship bias makes us all think that if you’re just smart you can build a Google or a Facebook. But the restaurants of Palo Alto are littered with the bodies of dead start-ups. Talk to any entrepreneur and the story is vaguely familiar:

Successes occur when a chain of remarkable events all line up exactly right. One good idea or one great employee or even an incredible product doesn’t always lead to financial success. You can do a lot of work to line up the right elements to improve your odds. But in the end, there is an enormous part that is luck. Malcolm Gladwell, in his book Outliers, describes in researched detail how unexpectedly random events and environments tend to make the difference between outrageous success and typical failure. It’s not just genius of Bill Gates or John Lennon. It’s a little genius, hard work, and a lot of other crazy stuff: Who you went to school with. The year you were born. An odd law on the books that suddenly made one set of opportunities viable.

Venture Capital firms will often bet on an untested management team with a killer idea, or an accomplished management team with a sketchy idea… but rarely both. The odds just get uncontrollably bad when you don’t have some basic things lined up.

I tend to think of entrepreneurial ventures as a roulette game: there are lots of spaces on the wheel, only one leads to success, and you have maybe one spin or, if you’re lucky, two, in any given game. All you get to do as an entrepreneur is cover over some of the spaces with tape to reduce the chances of a miss. Got a great idea? Cover over two spaces. A fantastic CEO? A couple more. A lucky break in the press? A few more. Bit by bit you do what you can to control the things you can control, lower the number of spaces on the wheel. And when the spin comes, while it’s still going to be luck, at least you’ve moved the odds more and more in your favor. That’s the best you can hope for.

Reed Hastings, founder and CEO of Netflix, (and considered one of the top CEOs in the country) occasionally will describe the lucky moments in the past that helped get Netflix where it is today. No matter how famously strategic and innovative as Hastings has been, it was luck that Blockbuster didn’t realize the opportunity in DVD-by-mail one year sooner, even after tiny Netflix tried unsuccessfully to convince Blockbuster to work with them. That inadvertent Netflix head start made it impossible for Blockbuster to catch up. This, like numerous other little elements that no one could imagine or control, just fell into place; and when combined with vision, competent strategic thinking and a good team, lead to the multi-billion dollar business Netflix has become.

So whether it leads to a good outcome or a tragic one, those extremes are results of the same kinds of improbable lining up of events. Perhaps an entrepreneur should be no more confident of success than he is terrified of flying. (Ironically, however, fear of flying is somewhat pointless. But confidence in the successful outcome in your entrepreneurial venture, well, that is actually one of the attributes necessary in the lining up of random items that builds to success. It IS causal, or at least a positive contribution.) In the end, I try to be realistic and measured – both in my fears as I board the plane, and my expectations of changing the world with a company. But hey, come on… hope springs eternal. Buckle up, and cross your fingers.

Serendipity vs. the Act of Will

What are the relative merits between being a master of serendipity and the opposite: making things happen for yourself that you want to have happen - of goal setting and producing desired results from a superhuman act of will.

It is a rare skill to surf the natural energies of life, (of business, of everything) – with deft grace and Zen-like acceptance. If the world gives you lemons, make lemonade. From my home I can watch “real” ocean surfers paddling out to put themselves in just the right position with respect to how things are moving around, being patient and watchful, and then knowing how to move themselves to quickly capitalize on an unimaginably enormous surge of energy, leveraging it for their own purposes. You don’t control the wave. At best you just get to ride it, not to be afraid of its power, balancing on an unstable surface in motion, gliding wherever it’s going, and perhaps dropping off when you don’t want to go there…

Knowing when to let go. That seems to be key too. I have long been inspired by the simian locomotion called brachiation. Swinging through jungle canopies, new world monkeys let go of a branch and fly through the air, hoping to catch something safe on the other side. They’re built for it, not only with prehensile feet—feet that grab like hands--but prehensile tails. And yes, occasionally they actually miss and hit the ground. But not often.

Personally, I like this serendipity camp and try to be a full-brachiator in my life. Watching the forces swirl, looking for a rising wave and enjoying a ride. Often this is manifested where two remarkably improbable events coincide, making an even more unlikely event spontaneously feasible. There is an adage that what appears as “luck” is simply the union of preparation and opportunity. To me this is where entrepreneurship, like surfing, resides – those who look lucky are simply highly skilled, they put themselves in the right place, they are unafraid of trying multiple times and unafraid of failing… and they know how to wait…

To some being a master of serendipity looks like magic. And we think it’s easy mostly because of a phenomenon called “survivorship bias” – where we tend only to see the winners, and all the monkeys that fell to the dirt disappear – and we are left with the false impression that all who play will win. To others a trust in serendipity seems lazy, unfocused, and unambitious -- as if you were adrift on an ocean, going wherever the winds might blow you. A vagabond, a drifter. But sailors can also tell you that regardless of where the wind blows, you can go wherever you set your sights.

And even gamblers, those people who roll dice and put their trust in the universe to deliver for them, tend to “fish their wish,” and try through an act of will to change the chaotic order towards their goal. Impossible, certainly – and yet when my dice "crap out" with an 11, I’ve been chided more than once that I wasn’t focusing…

The killers of serendipity are inertia and fear. Inertia is the tendency to move because you’re moving, or stick because you’ve been stuck. The first law of thermodynamics is powerful on our molecules, and seduces all evolved humans to behave more from habit and less from instinct. We tend to do what we’ve always done. We settle into routines. We prefer familiarity. Similarly it is fear that keeps us in bad marriages (fear of loneliness) and out of start-up companies (fear of poverty), or more generally, a fear of the unknown –jumping from a dull stable job to an exciting risky one has such an unpredictable outcome, the uncertainty is unnerving. The devil you know is better than the devil you don’t. So people stay put, they don’t let go of vines until they have another vine firmly in hand. In the animal kingdom, this is known as semi-brachiation: old world monkeys and apes move this way. Clearly, we are evolved from them.

So this brings up the opposite lesson: to pick a goal, and drive toward it. You don’t improvise building the pyramids or painting the Sistine Chapel. Plan your work and work your plan. Persistence in the face of adversity. Sailors go where they set their sights through skill and work. They leverage the powers of the wind but aren’t a slave to them. They make the winds take them where they want to go. The adage that always motivated me here was “Success is largely a matter of hanging on after others have let go.”

I know many writers and they’ll tell you that as much of an artform as writing is, you cannot only write when you’re inspired. You’re not always inspired. When those magic forces coalesce and a great work is produced, it’s nothing short of spiritual – the writer often feels just a vessel for some creative product that seemed to come from somewhere other than their own mind. But professional writers will simply tell you that writing is a discipline, it’s work, and you do it every day whether you’re inspired or not. Writers write.

So where does that leave me? Am I a serendipity ninja? Floating through the decades in a practice of preparation - and watching for all the trajectories of opportunity, calculating subconsciously where to stand to catch the ball. Am I the architect of my future? Where fate cannot be trusted to get the right supplies and right workers aligned to build that wonderful edifice – where to the greatest degree, each detail must be worked out in advance, and built on plan. I feel both, and neither.

And what of love? Is it magic, effortless, transformative art? Powered by serendipity, of chance meetings and funny coincidences telling us to pay attention? Or is it work, of patience and understanding and frequent pain, with some far off goal that we must apply ourselves to. When is it time to let go? and what is the goal?

And so perhaps there is a lesson.
We plan. We dream and design our lives, and we work tirelessly to construct them… but we learn not to pound square pegs in round holes, we learn to notice resistance when it occurs, and to stop pushing: we are sensitive to the forces that even we cannot control, and when we feel the wind coming around from the other side, or the wave rising that would be foolish to imagine we could divert, we have to know how to let go of the vine, flex like a tree in a storm, and drift naked and unknowing into a future, draped only in confidence in ourselves, in our ultimate impotence, and simply try to enjoy the ride.