More than half of the telephone calls Hollyanna McCollom receives are from friends, family and colleagues asking her for advice on Oregon. The questions vary—everything from “My mom is in town. Where should I take her to dinner?” to “What’s the best strip club in town?” So far, she hasn’t been stumped.

A native Oregonian, Hollyanna was the editor-in-chief of PDX Magazine (a “where to go, what to do” publication for the city of Portland) for two years before leaving to pursue a career as a freelance writer and full-time advocate for the city. The mother of two rambunctious, sword-obsessed boys, Hollyanna is a part time poet and part time pirate who spends her free time shopping in thrift stores and singing terrible karaoke punk songs. She lives in southeast Portland.