October 7, 2021
Next week we observe Columbus Day. Say what you will about the man’s skills as an explorer—even after four trips to the New World, he died believing he’d discovered a new route to Asia—or his mixed record dealing with Native peoples, one thing we can all agree on is that Christopher Columbus was a gifted pitchman and entrepreneur.
There are a few important lessons that every aspiring entrepreneur should know.
Perhaps some of you have been there before—standing in front of a roomful of potential investors, pitching your $1 billion business venture.
Now imagine the same scenario, except you’re standing before two of the world’s most powerful monarchs, seeking financing for a dangerous expedition into the unknown at a time when a good chunk of the population still believed the world was flat.
That’s precisely what Columbus did, of course, but did you know it took him seven years to convince King Ferdinand and Queen Isabella to support his crazy idea? And before going to the king and queen of Spain, the preeminent venture capitalists of the 15th century, he had already been turned away by England and France.
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That brings me to the first lesson:
1. Be persistent
Being persistent doesn’t mean never taking no for an answer. But facing rejection, while initially discouraging, can help aspiring entrepreneurs steel their resolve and motivate them to do better.
It’s hard to believe now, but many beloved films almost never saw the light of day. Raiders of the Lost Ark, Chinatown, and Pulp Fiction are just a few examples of movies that were repeatedly rejected by studios for a variety of reasons. Fortunately for cinephiles everywhere, the filmmakers didn’t give up.
Similarly, Columbus showed superhuman persistence despite one setback after another, and for that, he got to command not one but four historic expeditions.
On to lesson number two:
2. Be a disruptor
We’re taught that Columbus was interested in finding a new trading route to China, Japan, India and the rest of Asia. But it’s more complicated than that.
You see, there was already a perfectly fine trading route to Asia at the time: the Silk Road. However, in 1453, the Ottoman Turks took control of Constantinople, after which they forbade Christian traders from traveling the road. The Portuguese found a workaround via a new ocean route that took traders around the southern tip of Africa, but Spaniards were blocked from using this route without Portuguese license due to a treaty signed between the two nations in 1479.
Solution? Disrupt the playing field. Instead of confronting the Turks and Portuguese head-on, Columbus proposed beating them at their own game by finding a faster, better, more direct trading route, one that would eliminate the need to use the old way ever again. Consider it the equivalent of landline phones vs. 5G cellular technology.
3. Know your worth
Good ideas are a dime a dozen; great ideas are priceless. As such, you shouldn’t have to settle for less than what you believe your idea is worth.
Take Columbus: As part of his pitch to the Spanish monarchs, he asked to be named governor of all lands he discovered, to be given the office of Admiral of the Ocean Sea and to keep 10% of all gold, silver, jewels and spices he managed to bring back.
At first, Queen Isabella believed Columbus’s requests to be too extravagant and so turned him away for the umpteenth time. But as he was packing up to leave Spain, one of the queen’s advisors stopped him to say that she had changed her mind. Columbus, then, got everything he asked for.
I agree with Isabella. Columbus’s demands were excessive, and I don’t recommend you ask to be made governor of California during your next sales pitch. But you get the point.
4. No risk, no reward
This final lesson seems obvious, but rarely has it been expressed so emphatically as when Isabella finally agreed to finance Columbus’s expedition. Indeed, if he represents the startup in this scenario, then the queen is an angel investor who took a risk and was rewarded handsomely for it.
By the end of the 15th century, Spain had become the world’s largest economy. The unification of the kingdoms of Castile and Aragon contributed to this, but it was Spain’s claim on land and gold in the New World that pushed it to the very top.
Isabella could have let Columbus leave for good and seek financing elsewhere, but she took a chance on the son of an Italian weaver. As a result, capital flowed into Spain’s coffers.
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