The Pilot Who Wanted to be Steve Jobs

The scientific and unscientific proof that success in entrepreneurship is innate talent and choice, not the result of an MBA or mentoring.

Great entrepreneurs have four key qualities that they are born with.

Photo credit — AP

Recently I met a airline pilot who has been flying for more than 20 years. Now in his early fifties, he confessed to having a mid-life crisis. He wasn’t sure if he had spent his life doing what he wanted. He felt very inspired by Steve Job’s famous Stanford commencement speech. He quoted to me, “Stay hungry, stay foolish.” He wanted to quit and start a business. But he didn’t know what in…

And so I asked him, what are you passionate about. He said, “I don’t know”. Our conversation last 40 mins. I asked him that question three times. Each time it drew a blank.

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Some people love money. They become successful at sales or business because of it. That’s fine. Some people are obsessed with solving a particular problem. They become a scientist or start a company to provide a solution because no one else would or has. Some people believe in their ideas or products. They want to sell it to the world.

But many founders start a business today and they immediately think about how to secure venture capital; millions of dollars of it. As an angel investor I make it a condition that anyone I fund would have to put most of their savings into their startups. Or if they had no money to begin with, they had to be prepared a take a meager salary for years.

Any startup founder who wanted to pay themselves a market rate salary isn’t passionate about what they’ve started. They’ve obviously started the business to secure a job and pitched an idea just to raise money! I would only believe in those who sacrificed their jobs and their pay checks to start a business.

And I would only support those who raised capital to pursue their passions, not because they think their idea could become the next billion dollar ‘unicorn’.

Success is relative. If you love what you do the money will come.


Many entrepreneurs love to quote this statement from Jack Ma, but they always leave out the last part of what he actually said, “…but most die tomorrow evening.”

Still not convinced? Perhaps the richest man in China today can say whatever he wants and it will sound credible?

Watch this TED talk by Angela Lee Duckworth which had 15 million views at this time of writing. She studied both children and adults in various endeavors and found that only one quality was a reliable predictor of success. “It wasn’t social intelligence, it wasn’t good looks, it wasn’t physical health, and it wasn’t IQ. It was grit. Grit is passion and perseverance, for very long term goals.”

I rest my case on grit.


If you landed up on a deserted island with three other survivors, this might be the scenario you are faced with. One survivor will sit down and cry, mumbling over and over why she had to land up wet and cold and hungry on this desolated beach. Another may start to think about setting up a SOS signal and how to get rescued as soon as possible. And then the third may scout the island and figure what he had around him for food and shelter to stay alive first. If you had to follow just one, who would you go with?

Entrepreneurship is often described as a lonely, 24/7 endeavor, in a jungle where things often go wrong and people around you doubt you. Passion and grit will keep you going, but it doesn’t solve the problems you’ve encountered. Resourcefulness will — the ability to stay level headed and find different ways and means to help you survive and overcome obstacles.


In my first startup I had a business partner who worked for many years as a casino VIP manager. He remarked that most of the ‘whales’ in a casino were businessmen. There seemed to be a lot of entrepreneurs who also loved to gamble.

Many so called gurus and academics describe this trait of successful entrepreneurs with a more palatable terminology: risk-takers. The very definition of ‘entrepreneur’ by the Oxford Dictionary says “a person who sets up a business or businesses, taking on financial risks in the hope of profit.”

I once read in a book that doctors usually make bad stock investors. Because doctors are trained not to make mistakes. When they do make mistakes, they are often reluctant to admit it. Read “ Medical Culture Encourages Doctors to Avoid Admitting Mistakes”. On the other hand, any good trader or fund manager will tell you that making mistakes in judgment and recognizing them as quickly as possible are a natural and immutable part of their craft.

Towards the end of that conversation, the pilot who confided in me also remarked that based on his observation, most of his pilot friends did not succeed in business, save for a couple who ran modestly successful pubs.

He didn’t have an explanation as to why. I kept silent but I was suddenly reminded of what I read about doctors and investing. Civil aviation pilots are trained to perform a tried and tested routine, follow permitted routes, adhere to strict rules, and take no gambles in their jobs given the lives they have at stake.

Entrepreneurship is pretty much the complete opposite… Entrepreneurship can’t be taught.

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