Richard Millard’s impression of American hospitality didn’t start out great in 1965 when he arrived in NYC, having spent the first 16 years of his life in Norfolk, England. His taxi driver turned off the meter and charged him $75 for the ride in from Idlewild Airport, barely leaving him enough to pay his $1 nightly rate at the Y. He needed a job—and the first one he found was at the NY Hilton working the desk from 11pm to 7am.

That turned out to be a lucky break, and 50 years later, when we snapped Richard in his Coral Gables office this week, that colorful pocket hankie is a tip-off to how much fun he has every day as founder of the 25-year-old Trust Hospitality, now one of the premier boutique hotel operators in the country. With contracts to run 42 hotels in the 3.5 to 5 star range from Portland, ME, to Brazil and Colombia, Richard’s world includes spiffy local places like Villa Bagatelle, Stiles and Edgewater, and others like the famous Postcard Inn of Islamorada, and the luxurious new Zemi Beach opening next month in Anguilla.

Here’s how Richard rolls, having lunch at iconic old world Caffe Abbracci on Aragon Avenue where on Tuesday we snapped owner Nino Pernetti checking in a patron whom Richard describes as “one of Nino’s favorite gringos in the land of Latins.”

This is Richard’s motto, seen in a close-up of that picture hanging behind his desk in the first shot above: Done in the mid-90s, it symbolizes his philosophy that life is short, so you should have fun. His wife and daughter (a TV personality in LA) oblige, as do all local golf courses. And the weather—the reason he came to Miami after only a year in NY. In 1966 he was a bellhop at the Key Biscayne Hotel, handling Richard Nixon’s bags on the then ex-VP’s many visits. That other Richard may have left the Florida hotel scene, but our Richard is going strong.