The Digital Skeptic: Why We Have to Love This Total Loser

NEW YORK ( TheStreet) -- Alessandro Di Benedetto just finished last in the race of his life. Not merely last, but dead last, more than 5,000 miles behind the winners as they sailed into fame and glory. He was wet, alone and injured, slogging along with piddly, outmoded technology.

Which by rights, In our dog-eat-dog digital age, should make Di Benedetto a role model to exactly nobody, and most certainly not a bankable metaphor investors can use to suss out value in a complex marketplace that can be as unforgiving as the cold Antarctic seas.

But, over the past few months I -- and millions of others -- have followed this Franco-Italian's exploits via his on-board Web clips, emailed messages and wacky French media coverage as he circled the globe in a long-distance sailing race called the Vendee Globe.

It turns out this man is a veritable pirate's chest of investor inspiration.

"You know, before the race, I once took patients from a psychiatric hospital at sea. And the strongest on board were not the accompanying nurses, they were the patients, people we call crazy," was the translation I read from Di Benedetto's speech in French to a delirious throng of thousands after his finish in Les Sables-d'Olonne, the French sea resort town where the Vendee begins and ends.

This same crowd carried him over their heads for no other reason than they adored him so -- an honor I've never seen any sports hero get from the otherwise cranky French.

"We have one of the smallest budgets in the race and yet we finished," he told journalists.

This former engineer -- essentially a sailing amateur -- became the star of this year's Vendee, a 26,000 mile single-handed, around-the-world sailing marathon, an event that is bigger than the Olympics in many ways in Europe. Its winners accomplish this feat in almost absurdly powerful, high-tech and heavily funded 60-foot sailboats.

With a fraction of these dollars, Di Benedetto built a Web brand to match any of his rivals. Di Benedetto's on-board videos and content were wildly popular and, unlike most other racers, his finish was covered live over the Web. In the process, he turned his sponsors -- a handful of otherwise forgettable European plastic parts makers calling themselves Team Plastique -- into a European household name.

At least in my mind, all this makes Di Benedetto the rarest of rare commodities: a kind of investor's rudder for navigating the stormy digital economy.

Far from first
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.

Disclosure: TheStreet's editorial policy prohibits staff editors, reporters and analysts from holding positions in any individual stocks.

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