Met a girl, left a career in Toronto, moved to a city where I knew no one, and started over from scratch — no license, no connections, a pandemic on the way. I wouldn't change a thing.
In 2017, I packed up my life in Toronto and moved to Seattle for the most straightforward reason in the world — I had met Lizzie, and we wanted to build our lives together. What I didn't fully account for was what I was walking away from. My Canadian securities licenses didn't transfer. My professional network didn't transfer. Immigration took years, and just as I was getting settled, the world shut down.
Back in Canada, I had been fortunate to build a career in investments — raising capital, managing client relationships, and analyzing opportunities across mutual funds, hedge funds, and venture capital firms. But none of that came with me. I had to figure out what came next. That's when real estate started to make sense. For most people, their home is their biggest investment, and my background in economics and finance gave me a way to be genuinely useful — helping people think about their homes not just as places to live, but as assets that shape their futures. It felt like a natural fit, especially as Lizzie and I were thinking about growing our family.
I've been lucky to have experiences along the way that shaped how I connect with people. Growing up in London, Ontario, hockey was everything. At 19, I left home and spent a year traveling the Australian coast, selling wetsuits to surf shops out of an old VW Combi — and a few unforgettable weeks living with villagers in Fiji. It taught me that you can walk into almost any room and find common ground if you're genuinely curious about people. I was also fortunate to serve as President of TEDx Vancouver (Canada), organizing large-scale events where we curated speakers with messages and ideas that could actually move people — and it deepened something I already believed: the most important skill in any room is knowing how to really listen.
When Lizzie and I were house hunting, we stumbled into Burien/Normandy Park almost by accident — desperate to get out of our tiny downtown apartment before our lease ran out. We didn't know much about the area. What we found was something we hadn't expected: a real community. Young families, kids playing together, neighbors who actually know and socialize with each other.
We found out just how real that community was when our oldest son had a serious accident. We were terrified in the way only parents understand. And then the neighborhood showed up — people checking in, families offering help, folks from the nearby church keeping us in their thoughts. We hadn't even lived here that long. That moment meant everything to us.
Everything I've experienced — the career pivots, the relocations, raising kids, finding community — comes together in how I approach real estate. I understand what my clients are going through, whether they're just starting out, growing a family, or relocating somewhere new. My business has grown simply by making real connections and showing up as a person first. It's never been about sales — it's about making sure the people I work with feel protected and confident.
As a Partner at Holiday Road Hospitality Investments, I remain sharp on the investment side of real estate in ways that directly benefit my clients. Holiday Road is a 506c Registered Securities Offering that acquires and converts outdated hotels into technologically and operationally efficient properties and generates a handsome yield to our shareholders.
Now, with two young boys, most of my free time is spent coaching their hockey teams, taxiing them to their other sporting events, and spending time with the family in this wonderful neck of the woods that we are so lucky to call home! It's a pretty great life — and I don't take any of it for granted.
One of my favorite things about real estate is how personal it is. Every client, every home, every situation is different — and I genuinely love that. I try to make the process educational and even enjoyable, because buying or selling a home should feel exciting, not overwhelming.
I believe in being completely straight with people. If a home has real problems or doesn't make sense as an investment, I'm going to tell you. If it's a hidden gem with real upside, we'll talk through what that could mean for you if we put the work in. My job is to take the complexity off your plate, coordinate all the moving pieces, and make sure you feel informed and confident every step of the way.
My whole professional background has been about evaluating opportunities and making sure money is well spent — that translates directly into how I approach real estate, whether we're structuring an offer, negotiating terms, or finding value before a listing hits the market. When the transaction is done, I'm still here — a resource and a friend long after the closing table.
Sincerely,
Wesley Ollson
