The Investment Opportunity

As soon as Ugolino burst through the door, his brother could tell he was up to something.

"What is it this time?" Vandino asked. Ugolino only smiled in response, not yet ready to lay out his idea.

"Open the cask," he said, "this is best discussed over some wine."

Vandino rolled his eyes. His brother was constantly coming up with schemes that promised fabulous wealth.

"Is this anything like investing in the County of Tripoli?" Vandino sighed. "We lost a fortune there."

"Hey, that would have worked. It was Zaccaria's fault," Ugolino said. "He got greedy."

Vandino poured the wine, two cups worth, and set them on the table.

"No, no," Ugolino said. "We need four."

"Four?"

"Yeah, Doria and Guido are coming over," Ugolino answered. 

"I'm surprised," Vandino said. "I thought you'd burned Doria one too many times. And Guido? What money does he have?"

"Not to worry, fratello," Ugolino laughed. "They don't know about it yet. And we'll need Guido for this one."

Vandino could not possibly imagine what they would need someone like Guido for. He was just a modest weaver, who occasionally dabbled in making sails.
 
The two men arrived just after Vandino had finished setting places for them.
"This had better be good, Vivaldi," Doria warned Ugolino as he took his seat. "And don't ask for money."

"Who said anything about money?" Ugolino said, his voice dripping with feigned innocence. "Just a few drinks among friends."

The group chatted through nearly the whole cask of wine, covering everything from the Pope to the wretched villains from Pisa. Ugolino bode his time, waiting for the right moment to break in with his proposition. Making sure his brother and guests were sufficiently drunk was part of the plan.

“It makes no difference," Doria boomed to Vandino. "There isn't a man in Pisa capable of sailing to Genoa, let alone leading an army against us."

"You're right, Doria," Ugolino agreed. "We've got the best sailors around. We could sail anywhere. Even across the Ocean Sea."

Vandido shook his head to take exception with his brother's outlandish claim. No one could sail across the Ocean Sea.

"You've had too much wine, my brother," he scolded. "The bravado of the spirits is speaking now."

"I bet we could do it," Ugolino insisted. "You and I."

"You two?" Doria cackled, coughing on his wine. "You two can't even get through a month with needing to borrow money."

Ugolino's face stiffened.

"I could change all that," he said. "I've got an idea." Everyone else at the table groaned.

"No, no, hear me out," Ugolino begged. "This could make all of us rich."

"That's what you told me the last time," Doria protested. "And the time before that. And the time..."

"I get it," Ugolino snapped. "Just listen. There have been some developments that make this a better bet than most."

Vandino turned flush, embarrassed that his brother was in the midst of yet another scheme, waving his hand to shut Ugolino up.

"Let him speak," Doria said. "I'm sure we'll all have a hearty laugh at the end."
Ugolino was unfazed, determined to pitch his idea.

"Look," he said. "I have it on good authority that we can get through the Straits into the Ocean Sea. No trouble, no pirates."

"And?" Vandino interjected, with a crisp edge of doubt that thoroughly annoyed Ugolino.

"And I'm saying we can sail across it and get to India," he leaned back in his chair, pausing for effect. "Imagine a boat full of spices, free of customs, no Venetians or Pisans after our loot."

Doria didn't say anything. He sat searching for his better judgement to talk him out of it. Alas, he washed down his good sense a few glasses of wine prior.

"Guido here, he can make us some sails, sails built for some grand galleys, and he can rustle up some sailors through his contacts at the port," Ugolino explained. "All we need is some money to outfit the trip."

Doria put his fingers to his lips with the intention of blocking any agreement from escaping. It didn't work.

"It's interesting," he said. "As long as Vandino goes too. I've got to have at least one brother on the trip with his head screwed on straight."

"You in, Guido?" Ugolino asked excitedly. "Think you can help us out?"

"The Ocean Sea, you're nuts," Guido said. "Even the most desperate sailors would laugh me off the dock for such an undertaking."

"Why's that?" Ugolino asked sharply. "Because no one has ever done it?"

"Who knows if the ocean even reaches the whole way to India?" Guido said. "No one will ever sail to India, especially not heading west."
​
"You're just a weaver, Guido Colombo!" Ugolino shouted in drunken anger. "No one in your family will ever sail across a pond, let alone the ocean!"
 
The Real History:

The Vivaldi brothers, Ugolino and Vandino, set sail from Genoa in the spring of 1291. They headed down the coast of Africa, never to been seen again. A little more than 200 years later, the son of a Genoese weaver, proposed heading west to India and discovered the New World.