For a long time, Daniel Shoemaker didn’t think of himself as a Pearl guy.
In 2006 Shoemaker came to Portland from San Francisco, where he’d worked for microbreweries for about 14 years, with the intention of opening a cocktail bar. He and his business partner, Ted Charak, considered various locations and settled on the Pearl for its central location and walkability.
Teardrop Lounge opened in July 2007, and it was already a conceptual gamble: Although Portland had a nascent craft cocktail scene, a lot of customers when asked what they liked to drink seemed to just answer, “Anything sweet.” “It felt a little bit like we were yanking people along,” Shoemaker says…