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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.

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