William C. Paley — more casually known as Bill Paley — is a scion of a storied family. His father, William S. Paley, founded CBS. His mother, Barbara “Babe” Paley, was a style icon. Less well known is the fact that in 1896 his grandfather, Sam Paley, founded the Congress Cigar Company. When Sam retired in 1926, Congress Cigar shut its doors — until 2010, when Bill revived the business, naming it after his grandfather’s La Palina brand.

01 Best cigar you’ve ever had? A 1995 Montecristo A. I have one a year.

02 Favorite place to smoke? The Grand Havana Room in New York. It’s a beautiful private smoking club with a great view of the city.

03 Favorite restaurant? Le Zinc, a French bistro in Washington, D.C., where we’re based. It’s owned by a friend, and I always see someone I know or want to know.

04 Wine, beer or spirits? I don’t drink. I prefer green tea, Coke Zero and espresso.

05 Favorite city in the U.S.? New York. Not only can you find everything, you can find everything new. Abroad? Havana — just for the beauty of it. I’ve been about a dozen times.

06 Favorite getaway? Nantucket. I love the air. It’s the only place I go where I don’t think about someplace else.

07 How many days a year do you spend on the road? More and more each year. I’d say 60.

08 Motorboat or sailboat? Sailboat. I lived on a Te Hong II schooner for years, docked in Key West.

09 How much do you sleep? About nine hours. It’s a healthy amount.

10 What’s on your nightstand? My iPad, iPhone and glasses.

11 What are you reading? 1Q84 by Haruki Murakami.

12 Last listened to? Dave Mason, a wonderful musician who reflects the whole range of rock and roll. He played at my 50th birthday party.

13 Favorite piece of clothing? A nautical tweed bespoke suit made by Norton & Sons in London. I’ve had it about 30 years.

14 What do you wear to work? A polo shirt, jeans and Brooks Brothers cordovan loafers with yellow socks.

15 Unjustifiable extravagance? iPhone apps — I go crazy with them — and luggage. I’m always trying to find the right bag for the right trip.

16 Your watch? I wear a Rolex GMT-Master. My wife gave me a Rolex Daytona for Christmas, so that’s my new favorite.

17 Your business philosophy? If you pursue quality, profits will follow.

18 Best management tip? Listen.

19 Your investment philosophy? Buy low, sell high? I don’t know. I trust the people who are more experienced than me.

20 What charities do you support? Among others, Oxford House, which sets up sober-living houses, safe places for addicts and alcoholics to recover in. The Thelonius Monk Institute, which educates children in jazz. And the Washington Project for the Arts, a resource for local artists.


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