It was gradual and very organic, and I never really left music–I still play whenever I can. For me, though, the move into cigars as a real business had a lot to do with scrutinizing opportunities and figuring out what was best for the moment. In 2002, I moved to New York and went to work as a salesperson for Davidoff on Madison Avenue. I was still juggling sales with being a musician, and for a while I could pull everything off.
In 2006, however, Davidoff bought a store in the Time-Warner building, and I was offered a gig there as a general manager. This wasn’t just sales; it was a real gig, running the place. I knew that I would have to put my music career on the back burner, but I went for it. Two years later, I was asked to run both Davidoff stores. I was 28 and I had a serious girlfriend, so I decided to I had to do it. I took a few more chips out of the music pile and put them in the cigar pile.
A few years later, in 2011, the Sherman family reached out and talked to me about running their store in New York–the Townhouse, as we called it. I loved the Shermans, but I loved Davidoff, too, and it didn’t make sense to go from running two stores to running one. But the Shermans were persistent, and they put it to me that they didn’t just want to build up their store; they wanted to rebuild the cigar culture and community, making their products more relevant, getting them into brick and mortar stores.
I was honest with them and said that I was happy where I was, but they put it to me directly: They wanted me to come in, and they would trust me to run the place how I wanted. So I went with them, and over the next 10 years I helped them polish and fine-tune the final chapter of the Nat Sherman International story.