Iin Portlandthe person helping you find your next home might have been an indie rocker or news anchor whose voice on the 11 p.m. newscast was the last thing you heard before you went to sleep, or a local athlete who has definitely hung up his professional gear after covering himself in glory on the court of his choice. We caught up with some of the bold names finding second careers in Portland’s big real estate scene to see how they made the leap.
Then (and, intermittently, now): keyboards, percussion and bass guitar for the
Dandy Warhols, the seminal alternative rock band based in Portland, also has side hustles fronting country band Brush Prairie and performs as DJ Rescue
Now: Broker at A to Zia Real Estatevia Windermere’s Westmoreland office
Why: “[All the band] had kids and wanted to be home [in Portland] After. I made a list of things I could do that would fit in with my music career, even though 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.
Following: Co-founded Happy Dance Properties to invest in multi-family residential and commercial properties
Then: KATU news anchor for two decades
Now: Broker with RE/Max Equity Groupbased at 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 that. I thought, “I can go meet people, help them, organize things and plan, do research and present ideas to them – OK, that could be my full-time job. I passed the real estate exam in three weeks. All those years of really learning how to listen and talk with people have transferred beautifully. People from the past have invited me to their homes. Now I’m not looking at a lens. It’s no longer a one-way conversation.
Following: Keeping a Foot on TV Hosting “Eye on the Northwest” for KOIN
Then: A formidable defender who helped the Timbers win the MLS Cup in 2015; known for his signature red beard
Now: A real estate investor which specializes in buying multi-family and commercial properties in Salem; still a local sports TV personality
Why: “In 2005, I had just received a very small bonus for playing professional football, about $5,000. I wasn’t sure what to do with the money, but I had a good friend whose mom was a real estate agent and she told me we should try to buy a house. I roamed the streets of South Denver for three or four months, looking for homes. Finally, there was an estate sale for a house in a mess the way the 1950s spewed everywhere — pink and lime green everywhere. We made a decent offer, bought a $200,000 house and invested in it. It was my first experience and I loved it. I was always going to be able to play professional football for a limited time. So every time I got bonuses, I bought property. When I was traded to the Timbers, I tried to figure out which market I should go into. Portland was way too expensive. Vancouver too. I didn’t smell Gresham. Eugene was too far away. But Salem, wow.
Following: Launch Pro-Active Investor, a online platform designed for professional athletes who want to learn the ins and outs of real estate investing
Then: Former television studio host for the Portland Trail Blazers
now: Work in titles and receivership for lawyers Title in northeast Portland
Why: “In 2014, I posted on Facebook. I worked game nights 90 nights a year, regular season and playoffs. I had to find something to take more time. So I asked, ‘Does anyone have any ideas for me for a part-time sales job?’ I had a friend from years and years ago at PSU who said to me, “Have you ever thought about title and escrow?” I thought, ‘That sounds so boring, I would never do that.’ I’ve been doing it now for seven years [and I love it]. If a real estate agent or lender talks to me, they know a bit about who I am and it’s a great conversation. Maybe a third of the business I’ve won is because people know who I am.
Following: He still holds a nightly gig as KOIN’s athletic director and keeps an open line with Blazers star Damian Lillard.
Three more familiar faces: Jenelle Isaacson, founder of local juggernaut Living Room Realty, transitioned from a career leading female indie-punk band Spread Eagle | Timber Joey, aka Joey WebberTimbers mascot wielding chainsaw on game day, mild-mannered real estate the rest of the time | Kyle Huckabeefamous married via 90 day fiance and featured on several spin-off shows, and a broker with eXp Realty in PDX and Vancouver.