At a guess, I'd hazard these guys were never really sailors at heart. The boats they commissioned were monuments to their own egos, something complicated and tangible to spend money on, markers in the pissing contests the rich have always engaged in. Palaces and pyramids. Perhaps at a deeper and more charitable level, they see a sailboat as objects of liberation and calm, something to might balance the frenetic,cut-throat, greed-driven pace of their business lives. "Just get me out of this boardroom and onto a sailboat, kicked back listening to Jimmy Buffet and drinking milk outta coconuts."
Of course they get it all wrong, falling straight back into their Type A habits. Gonna go for a sail? Then by God build me the biggest, gaudiest, most high-tech and expensive mega-sailboat ever! I want swimming pools. Tennis courts. A minisub. Two. A crew of hundreds.
Then it turns out to be expensive to own, not very much fun, hardly relaxing at all. The very rich have short attention spans and are never satisfied. So it's on to the next monument. What about the giant sailboat, sir? "Sell it. I'm on to the next pissing contest." Not sure they ever really understand, It's Not About the Boat.
There are some big, splendid, expensive sailboats represented on this forum. But the difference between their owners and, say Tom Perkins? I bet if all they could afford was a 25' Catalina circa 1985 ... they would still sail the hell out of it. Not to impress anyone, not to salve something missing in their life, but out of sheer love for the wind and water. They are sailors. Joe Vittoria's just a guy who made a bucket of money renting out cars and wants everyone to know it.
Albin Ballad 30, Fionn