In a few weeks, I’ll be in Portland, Oregon, for Shawn Busse’s always terrific Catalyst event. That trip has had me thinking about the city’s keep-it-weird ethos, the spirit that’s made Portland a hotbed for creative business building. My upcoming trip has also inspired me to revisit a podcast conversation Shawn and I recorded in early 2024 with Jenelle Etzel, who is founder of Living Room Realty. The boutique real estate agency has more than a hundred brokers and a reputation for doing things differently, but Jenelle didn’t set out to be a business owner. In fact, she majored in weaving (Shawn, for the record, majored in ceramics). She fronted a punk rock band. She lived out of a van. And yet, those experiences—especially learning how to manage people who didn’t technically have to listen to her and how to serve customers who’d been ignored by the mainstream—turned out to be perfect preparation for building a thriving business in a quirky city. It’s a story that says something about Portland, but even more about the unconventional paths that can lead to successful entrepreneurship.