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The sky’s the limit: Why pilots make great start-up employees, and why so many are entrepreneurs

By Ron Wiener, CEO, Earth Class Mail

I’ve been flying airplanes since 1984, and it is the greatest passion in my life outside of my own family and my addiction to start-up companies. For some pilots it’s about boring holes in the sky. For others it’s about just getting from Point A to Point B more efficiently. For me, it has always been about associating with ordinary people who have chosen to do an extraordinary thing – getting their pilot’s license, and beginning their never-ending quest of improving their skills and racking up their extraordinary experiences.

In this brotherhood of aviation I’ve met Fortune 500 CEOs and musicians, generals and housewives, astronauts and college students – all of whom share a common passion and were able to focus and achieve something special that 99.5% of the rest of the population hasn’t or isn’t even interested in attempting.

One can find many parallels between the kinds of people who fly airplanes and the kinds of people who succeed in entrepreneurship. But my first observation about these two populations is that aviation, like entrepreneurship, takes people from different walks of life, different educational and work experiences, even different cultures, and puts them all on a level playing field. It has always been amazing to me to watch a high-powered CEO taking lessons from a 20-year-old certified flight instructor (CFI) and bowing to her superior knowledge and experience, cowering at her admonitions and begging for her praise for any maneuver well done. What you do or have done in your business, medical, legal or other career, or in school, will have little bearing on what you’re about to do when you first start learning to fly airplanes. Anyone with more hours, more pilot ratings, more experience flying than you have under your belt is your de facto mentor in the air, and valued comrade on the ground.

The correlation to entrepreneurship is quite subtle. I’ve seen veterans of large corporations – with amazing two- or three-decade résumés filled with executive titles and major accomplishments – arrive at a start-up only to fail utterly within weeks or months. Since the skills that allowed them to be highly successful in large bureaucracies are largely non- transferrable to start-up culture, the key question is whether they recognize what they don’t know and can they lower themselves to learn from younger, “less accomplished” folks who actually have more experience than they do in surviving and thriving in a start-up?

This is but one reason that, all other things remaining equal, I always hire pilots into my start-ups whenever I can, at all levels of the organization, and especially in the top ranks. Where a non-pilot may take a superior attitude to others on his or her team who came to the company with less impressive résumés, good pilots know that there is something valuable to be learned – possibly something life-saving - from even the youngest person, way low on the totem pole, who has nevertheless been at the entrepreneurship game longer. Non-pilots (and especially their spouses) often misunderstand why we spend so much time “hanger flying” with our fellow aviators, and reading magazine articles about harrowing experiences of other pilots – some living to live to tell about it, others written by accident investigators. They do this because it is easier and ultimately more prudent to learn from others’ mistakes rather than learning by making your own mistakes. As we know, man is the only creature with the ability to learn from others’ mistakes, yet often refuses to do so, bound and determined to create his own lesson plans by repeating avoidable missteps.

In a nutshell, this boils down to whether your ego is stronger than your instinct for self-preservation. As the saying goes, “there are old pilots and there are bold pilots, but there are no old, bold pilots.” Same goes for entrepreneurship. Look around the scene and you’ll find a common trait among successful entrepreneurs is their ruthless determination to learn from others’ experiences rather than assume they already possess everything they need to know to run a successful business because they attended an Ivy League college or worked at a well-known major corporation. Great entrepreneurs spend a lot of time meeting with other entrepreneurs, reading books and attending speeches by other entrepreneurs, and spending a lot of time listening to people in their own organization. They surround themselves with good advisors – board members, mentors, and paid professionals – and they take in as much advice as they can before making critical decisions.

Statistically 80% of start-ups fail because they run out of capital. Okay, but why did they run out of capital? What could they have done to not run out of capital? Ask anyone who has shut down their start-up why it failed and they will often tell you exactly why – hindsight being 20/20 – that failure could have been avoided was it not for “just one thing.” That one thing may have been an underestimated time to market, or a dispute among co-founders, or a product failure of some sort. If you ask them “did anyone ever express concern to you over the issue that ultimately killed your business, which you chose to disregard at the time they mentioned it?” candid entrepreneurs will usually confess that indeed they were warned in advance but went ahead with their business launch anyway.

Guilty as charged. Most successful entrepreneurs fail with the first one or more companies before they strike gold. My first two companies – ironically, aviation companies – in fact didn’t make it. I don’t look back and think “gosh, I’ve wasted seven years of my life and all my capital on those ventures.” I look at it as valuable experience gained that increased the odds of success of the next ventures. And indeed that is how things worked out, but if I have to be candid about it I could have listened more to investors (including those who chose not to fund us), board members, colleagues and employees who predicted the ultimate cause of death before it hit us.

Flying airplanes or even flying in airplanes as a passenger requires a suspension of disbelief – without an education in basic physics an airplane sitting on the ground doesn’t look like it should be able to fly. To most people, launching a start-up is as scary a prospect as it was for people to climb inside a Curtiss Jenny a century ago and believe it will defy the laws of gravity. As millions of people get on airliners routinely these days, society has also slowly become more respectful and encouraging of people starting their own businesses. But what we want to know about the pilot in the cockpit is what we want to know about the CEO of any start-up – that they’ve had experience at the controls, that they have good training (including good mentors), and that they’ve put their own skin in the game. (Would you get on board an airliner if the pilot were flying it by remote control from the safety of the control tower? Probably not!)

One other aspect of being a pilot that pays great dividends in any fast moving organization, and especially in startups, is the discipline of clear, concise, and appropriate communications. A student pilot learns early on that we say “one-two-niner” on the radio because “nine” can be confused with “nein” to a German, and “one twenty nine” can easily be misheard as a compass bearing 100-degrees off and headed straight for granite on a heading of “twenty nine.” While the FAA says that the person at the controls is the “pilot-in-command” (PIC) of their aircraft, they have a responsibility to communicate their progress points to air traffic control and other pilots in the air around them, and to request approvals from air traffic control before taking certain actions. This discipline is very helpful in start-ups. I find I work best with people who take charge of their own tasks and don’t require me to micromanage or nag them for details because they communicate too little of their progress, or are reticent to call me if they need help or should get approval before taking key steps forward. The efficiency in communications between pilots is not just about limiting airtime by using special lingo, it is about knowing when you should or must communicate, and not to pollute the airwaves with over-communication. Think of airwaves as your email and voicemail inboxes and your time spent on calls and in meetings. At the speed of a startup communications efficiency is hypercritical.

Unfortunately only one out of 200 people you’ll find in the workplace are likely to be or have been at some time a pilot. I wish there were more of them to hire. But when you take a look at the statistics of highly accomplished business people, professionals, and especially entrepreneurs, you will find a much higher percentage of pilots than in the general work force. In fact, CEOs, doctors and lawyers make up the top three largest segments of the private pilot population. I’m not saying you have to be a pilot to be successful in start-ups, or that you need to be particularly smart to fly an airplane (any sufficiently trained monkey can do that), but the character traits of someone who has previously taken on – and achieved – bold initiatives like getting their pilot’s license definitely pays dividends in a rapid-paced start-up company. It’s because they are willing to learn from their own failures (learning to fly an airplane is accepting that you will make many mistakes in the process of becoming proficient) but are also apt at honing their own survival skills by benefiting from the mistakes of others, because the cost of utter failure (a plane crash, or a business collapse) can be very real and painful.

If you’ve read this far and decided that you want to go earn that pilot’s license you’ve always dreamed of since you were a kid, check out www.beapilot.com. By the way, you’ll find that the VC and angel investor ranks are chock full of pilots – and whether they consciously think about it or not, they’re probably more likely to back you if you’re a pilot, too. One more incentive to get ‘er done!

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