• Learn from Christopher Columbus

What Entrepreneurs Should Learn from Christopher Columbus

by Noel Bagwell
for ExecutiveLP®

October 10, 2016

Happy Columbus Day!

“Following the light of the sun, we left the Old World.” — Christopher Columbus

Say what you want about Christopher Columbus; the man had courage. He did something no one else had ever achieved. He crossed the Atlantic Ocean in an organized, intentional way; he reached the West Indies; he established trade with the indigenous peoples, there; and he returned to Spain, where his expedition subsequently improved the lives of the nation’s subjects. Christopher Columbus was an adventurer, an entrepreneur, and a hero.

Imagine Christopher Columbus going on Shark Tank. What would that pitch have sounded like? Would Barbara Corcoran or Lori Greiner have given him a deal? I’m thinking probably not. For one thing, the risk he was taking was insane.

Enrique Pareja, a well-travelled Spaniard, estimates “the provisioned amount for

[Columbus’s] first voyage was, in today’s ‘purchasing power parity’ terms, ~40 MM USD,” that is, approximately US $40 million. Then, as now, only governments or the world’s wealthiest Adventurpreneurs, like Elon Musk or Richard Branson, would take such a risk (and only they are).

But risk and reward often have a strong connection, if not an outright correlation. As an entrepreneur, like Columbus, you have to be willing to take huge risks if you want to make a world-changing impact.

Columbus wasn’t just a risk-taker. He was a team-builder. He put together three ships’ crews–three whole teams–just for his first voyage. These were guys going into a part of their map which said, “Here, there be dragons.” They were prepared to die. Some probably expected to die. Nevertheless, Columbus was able to persuade them to join him. He had to have one hell of a pitch! (Okay, well… Gomez Rascon and Christoval Quintero, owners of La Pinta, were pressed into service against their will. So, maybe he didn’t have to try that hard in every case.)

Columbus didn’t just have a dream and a good sales pitch, though, he had powerful backers. Queen Isabella of Spain was one of Europe’s top “influencers.” With her husband, Ferdinand the Catholic (King of Castile jure uxoris), she enjoyed an incredibly effective monarchy on notably equal terms. Their motto was, “Tanto monta, Isabel como Fernando” (“They amount to the same, Isabel and Ferdinand”). These were people who knew how to cooperate to get things done.

Columbus persuaded these effective leaders to sponsor his expedition to reach the Indies, sailing west. Interestingly, as pointed out by John Edwards in Ferdinand and Isabella, Spanish treasury records indicate no royal payments were made to Columbus until 1493, after he completed his first voyage. This means Columbus either had to work out some seriously insane credit deals, or he had to put his money where his mouth was. There is a lesson, there, your risk has to match your investors’ risk. Why would your backers be willing to risk more than you?


To persuade Isabella and Ferdinand, Columbus had a great plan. Even when things didn’t go according to plan, he was capable of adapting to his circumstances, and always moved forward. He never would have reached the New World, if he had given up when the rudder on the Pinta broke. (Remember Rascon and Quintero? They were suspected of sabotaging La Pinta‘s rudder.) Columbus also braved the threat of Portuguese capture, and, of course, getting lost. On September 13, 1492, Columbus observed that the needle of his compass no longer pointed to the North Star. Once his crew found about this, some of them threatened to sail back to Spain, homesick and terrified. Columbus reassured them that he could still navigate, and they continued their journey–ultimately to great success.

Starting a new venture is always an adventure, and there is always some risk involved, if it’s an enterprise worth pursuing. You have to have a plan, a great pitch, and strong backers. You need to be a team-builder and a risk-taker. You have to have confidence in your own abilities. We’re privileged to work with and support these kinds of entrepreneurs. It’s what we love doing.

As an attorney–a lawyerpreneur, myself–my role is that of strategist, helping you form your plan, and supporter, helping you navigate and confidently sail your business through waters unfamiliar to you. Helping to form and guide businesses is always an adventure, and no two are exactly alike. I hope if you’re planning a new venture, you’ll let me help you with the planning. I can be with you, supporting your business with General Counsel services as you strive for every milestone along the way. Let’s be like Columbus, and discover something great, together: your potential.

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