“I’m all in,” he said, slathering horseradish on a steak sandwich at Morton’s last week.
Paley, 63, was a bit thin when it came to divulging the financial details of La Palina. But I decided to write about him anyway because his story is more about rebirth, self-expression and dogged entrepreneurship than it is about making money, of which he already has plenty — thanks to his dad.
I like cigars, having been a loyal customer of Nat Sherman’s Metropolitan University series for 20 years. Besides, Paley is likable. He is straightforward and, for a man who says he avoids small talk, is a great conversationalist, sliding easily between various topics, from the intricacies of jazz to the inner workings of the brain (his maternal grandfather was a brain surgeon).
Born to great wealth, Bill spent much of his early life having fun, although I would not call a one-year Army tour in Vietnam “fun.” He studied film, lived in the Everglades, sold yachts, lived on a yacht and bounced around before bankrolling some bars in Washington and Baltimore during the 1970s.
His bars included the popular Gandy Dancer on Capitol Hill, the Brass Elephant in Baltimore (where he lost $250,000), the Biltmore Ballroom in Adams Morgan and a profitable teen disco called Little Feet in Fairfax County, housed in an old Hot Shoppes that was due for demolition.
After a stint in drug and alcohol rehab, Paley found his calling as an addiction counselor, which he pursued for nearly two decades. It engaged his mind and centered his life. He was good at it.
“I was just having fun up until then,” he said.
He also began thinking about reviving the family’s cigar business, which his immigrant grandfather, Sam Paley, had begun in Chicago in 1896.
“My dad’s father came home and talked about the cigar business all the time,” said Paley, smoking a La Palina on the restaurant’s terrace above Connecticut Avenue and L Street. “Dad spoke of the cigar business warmly, so I imagined it warmly.”
Over the past decade, he started buying cigars, studying the subject and collecting them.
“The moment clicked when I suddenly realized that because of my heritage, I had a product that I could really market. I had a narrative. I got back to a passion which the family had. It felt right.”
He called a patent lawyer about 2006 and bought the rights to the La Palina (La Palina is a play on Paley) brand for $5,000.
Early on, Paley made a decision that went against advice. He would start with a super-premium cigar, with high-end tobacco, a spare-no-expense band, all wrapped in a cigar box that could become a keepsake.