No question, at first glance Di Benedetto appears to be a miserable investing metaphor. He was far from the most efficient. That honor went to sailing pro Francois Gabart, who set a course record of 78 days and a single-day sailing distance record of 545 miles. His story isn't the most dramatic. Jean-Pierre Dick lost the critical ballast needed to keep his boat upright a full 2,400 miles from the finish but still managed to finish fourth, only six days behind Gabart. And Di Benedetto was not the cleverest. Boat builder Tanguy De Lamotte hit not one, but three, submerged objects and kept from sinking deep into the South Atlantic only by executing complex composite laminates in short shifts while pumping -- sleeping no more than 45 minutes at a time. Money in the hold
But what made Di Benedetto a people's champion -- and his competitors amateurs by comparison -- was his pro-level passion for the sea, wind and stars. Like the greatest entrepreneurs, Di Benedetto showed over and over an uncanny ability to manipulate the world around him to add value. If you study him as I did, you'll see a man who seemed to enjoy being cold, hot and/or terrified. After a fall broke his ribs, he kept making extravagant crepes flambe meals from freeze-dried food, all the while blasting along at 20 knots far south in the Indian Ocean. He shot hilarious Christmas videos, including a visit from Santa. He crooned along to Puccini MP3s 1,000 miles off the Australian coast. He interviewed a pelican in the Atlantic and an albatross in the Antarctic seas. "I never pushed the boat too hard," he told reporters. "I never even pushed her at 100% of her potential. Because the most important thing for me was to finish." And in the process he did much more than that: To these tired eyes, he showed investors how to profit from technology. When you seek to create value by harnessing what is new in the world's tools, sure, the tech developed is important. But it's the person using that tool that's the money in the bank. Which draws this investing parable: The trick in this dark digital age is not finding the next great technology, but finding the next great Di Benedetto. That Steve Jobs or Henry Ford kind of doer that distills humanity from metal, plastic and the wind. And then finds a way to share it with the world. Because if Alessandro Di Benedetto is considered a loser, I'd hate to see what winning looks like.