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Add mentionIn 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.
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Join the GridAbout 21 Hats Podcast
The 21 Hats Podcast presents an authentic weekly conversation with small business owners who are remarkably willing to share what’s working for them and what isn’t. Unlike many business podcasts, which tend to talk to highly successful entrepreneurs whose struggles are in the past, the 21 Hats Podcast features a rotating cast of business owners who are still very much in the trenches fighting the good fight. Every week, our regulars gather to talk about the kinds of important issues many owners won’t even discuss behind closed doors: whether their businesses are as profitable as they should be, whether they are willing to give up some control to an investor in order to grow faster, why they had to lay off employees, how they wound up with way too much inventory, why they don’t have a succession plan, and even why they are concerned about their own mental health. Visit to hear all of our podcast episodes, read episode transcripts, and learn more. The show is produced by Jess Thoubboron, founder of Blank Word.
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