The Digital Skeptic: Standing at The Edge of The Internet

WALDOBORO, MAINE (MainStreet) -- Anybody with skin in the big-time technology game might want to pay a visit to this small town.

You won't find much here. Waltz Pharmacy. The hippie bakery that can't seem to stay open. The Narrows Tavern, which my mom says has the best burgers around. And over at the mouth of the Medomak River, I see only a few boats. Two are filled with rainwater.

Thing is, not too long ago -- my father could have seen it when he was a kid -- this place was the white-hot ground zero of a technological revolution. And not for goofy stuff such as computers or networks or smartphones, but something far more important to investors: the delicate, marvelously profitable balance of human ingenuity, commerce, physics, information systems, construction, wood, glass, metal, wind, sky and sea.

That is, commercial ship making.

From the mid 17th century until about 1910, when the network of global commercial sailing ships finally fell off the earth, this part of Maine was this country's Silicon Valley -- where the world came to see how the present met the future. In 1856, according to the Maine Maritime Museum, Maine built more shipping tonnage than Massachusetts and New York combined. And if nearby towns such as Belfast, Bath and Rockland were the Mountain View, Los Gatos and San Jose, Calif., of that era, Waldoboro was its Cupertino: the very apex of the art and science of commercial sailing craft. This town pioneered the construction of two-, three-, four- or even five-mast sailing schooners, brigs, barks and full ships. These fabulously lovely boats had names such as the Governor Ames, the James W. Fitch or the E.O. Clark and could carry massive cargos, but needed only a few men to crew them.

And the media -- let's say newspapers -- marveled at the money these boats took down for investors. Local farm boys such as Joseph Clark or Henry Kennedy, who were penniless as kids, went out as rich as anybody. When Clark went into the ground, it was reported, he left a fortune of nearly $750,000 -- and that's when 10 cents bought a nice lunch.

Yet historians still gasp at how swiftly the end came for Waldoboro's technological and business prowess.

"How would anyone guess," wrote Mark W. Biscoe in his definitive history of the period, Merchant of Medomak, "that after reading the optimism, that this industry would be dying in just a few years."

But like many waves of innovation before and since, die it did.

What happened? Like what's happening today. The markets finally figured out that the business of networking the world with low-cost packets of cargo -- sailing ships -- powered by a free-to-all resource -- the wind -- was a crap business. Much more lucrative was investing in 10 or 100 times more complex and expensive ships made of steel and powered by steam and running those massive craft on a razor-tight schedule.

Sure, sailing's technological legacy lurks here in Maine -- if you know where to look. The legendary yacht design firm Stephens Waring still operates out of Belfast. Bath Iron Works is now a "surface combatant builder" -- that is, it makes things that float for the Navy. But mostly, the once surefire technologically driven market of commercial sailing -- which, without exaggeration, made this country rich -- is gone.

They say a single iron ring from Kennedy's great shipyard is still hidden next to the Storer Lumber yard. But I couldn't find it. And as I looked, I realized what investors' biggest worry really is in the information age. Not what the next Google (GOOG) or Facebook (FB) or Twitter will be. But what the next Waldoboro will be.

That is, being utterly on the wrong side of history.

Stand here -- and taste the emptiness -- and you will see by just how terribly easy that is.

This commentary comes from an independent investor or market observer as part of TheStreet guest contributor program. The views expressed are those of the author and do not necessarily represent the views of TheStreet or its management.