In Portland, the person who helps you find your next home might have been an indie rocker or a news anchor whose voice on the 11 p.m. newscast was the last thing you heard before going to sleep, or a local athlete who has hung up their pro gear for good after covering themselves in glory on their field of choice. We checked in with some of the bold-faced names who’ve found second careers in the greater Portland real estate scene to see how they made the jump.
Then (and, on and off, now): Keyboards, percussion, and bass guitar for the
Dandy Warhols, the seminal Portland-based alternative rock band, also has side hustles fronting country band Brush Prairie and performing as DJ Rescue
Now: Broker at A to Zia Real Estate, via Windermere’s Westmoreland office
Why: “[All the band] had kids, and wanted to be at home [in Portland] more. I made a list of things that I could do that would dovetail with my music career, even as we decentralized touring. I didn’t want to be a bartender. I wanted less nightlife, not more. I have a good head for numbers, and I really love and know Portland—and I know a lot of people. The list was really short.”
Next: Cofounding Happy Dance Properties to invest in multifamily residential and commercial properties
Then: KATU news anchor for two decades
Now: Broker with RE/Max Equity Group, based in Lake Oswego
Why: “When my contract ended [at KATU, I thought], ‘Where am I supposed to be?’ I grew up in a real estate family. I had this inherent knowledge. I was comfortable with it. I thought, ‘I can go meet with people, help them, organize things and plan, research, and present them with ideas—OK, that could be my full-time job.’ I got through the real estate exam in three weeks. All those years of really learning how to listen and talk with people transferred over beautifully. People in the past invited me into their home. Now I’m not staring at a lens. It’s not a one-way conversation anymore.”
Next: Keeping a foot in TV by hosting “Eye on the Northwest” for KOIN
Then: A fearsome defender who helped the Timbers win the MLS Cup in 2015; known for his signature red beard
Now: A real estate investor who specializes in buying multifamily and commercial properties in Salem; still a local sports TV personality
Why: “In 2005, I had just gotten a very small bonus for playing professional soccer, about $5,000. I wasn’t quite sure what to do with the money, but I had a good friend whose mom was a real estate agent and she said we should try to buy a house. I drove up and down the streets of South Denver for three or four months, looking for houses. Finally, there was an estate sale for a house in a state of disarray, like the 1950s threw up all over it—pink and lime green everywhere. We put together a decent offer, bought a $200,000 house and put the sweat equity in. That was my first experience and I loved it. I was always going to be able to play professional soccer for a finite amount of time. So every time I got bonuses, I would buy a property. When I was traded to the Timbers, I tried to figure out which market I should get into. Portland was way too expensive. So was Vancouver. I didn’t feel Gresham. Eugene was too far. But Salem—wow.”
Next: Launch Pro-Active Investor, an online platform designed for professional athletes who are interested in learning the ins and outs of real estate investment
Then: Former TV studio host for the Portland Trail Blazers
now: Works in titles and escrow for Lawyers Title in Northeast Portland
Why: “In 2014, I posted on Facebook. I was working game nights 90 nights a year, the regular season and playoffs. I had to find something to take up my time more. So I asked, ‘Does anyone have any ideas for me for a part-time sales job?’ I had an friend from years and years ago at PSU who said, ‘Have you ever thought about title and escrow?’ I thought, ‘Sounds so boring, I would never do that.’ I’ve been doing it now for seven years [and I love it]. If a Realtor or lender talks to me, they have a little bit of a background on who I am and it’s a great conversation. Maybe a third of the business I’ve brought in is because people know who I am.”
Next: Still holds down a nighttime gig as sports director for KOIN and keeps a line open to Blazers star Damian Lillard.
Three more familiar faces: Jenelle Isaacson, founder of local juggernaut Living Room Realty, pivoted from a career fronting all-female indie-punk band Spread Eagle | Timber Joey, a.k.a. Joey Webber, the chainsaw-wielding Timbers mascot by game day, mild-mannered real estate the rest of the time | Kyle Huckabee, famously wed via 90 Day Fiancé and featured on multiple spin-off shows, and a broker with eXp Realty in PDX and Vancouver.