Outside the Rat Race: 2026

If 2024’s theme was survival (with Jessi’s brain tumor and saying goodbye to our dog). 2025’s theme was new growth! I grew a new business, learned new skills, grew our rental portfolio, watched our new dog grow, and visited new places. Lots of new, exciting growth areas!

Property Management

At the tail end of 2024, I started a property management company, but didn’t get my first owner/client until January 2025. Since then, I’ve been on what feels like a steep growth curve with 87 units under management (in addition to managing 105 of my units). I spent considerable time building out my systems and team to keep up with growth (while occasionally going to fix something). It’s been fun solving new types of problems (like setting up payroll), but finding the balance between working in my business versus working on my business is challenging.

All of my growth has come through word of mouth, and this year I’d like to be more intentional about generating leads. One idea is to provide valuable rental tools/insights for real estate agents, since they’re often the ones making recommendations to investors. The goal is to build a liking/trust with them so they recommend my company.

I’m excited to keep growing here!

Drone Pilot License

I like flying, but it isn’t the best use of my time or money to learn to pilot airplanes. So, a second choice was to get my Part 107 license so I could fly my drone. I took the class through the Pilot Institute, and it was fantastic. I enjoyed learning about the different airspaces, how to read aerial maps, and so much more. And now I can legally take photos for my business.

CCB License

It turns out that in Oregon, if you build a house with the intent to sell it, you’re required to have your contractor’s license. So, I got my general contractor’s licence from the Construction Contractors Board (well... almost, I’m still waiting for final approval from the CCB). Beyond letting me do development projects, it might also be useful for my management company.

Baker Tower

I syndicated my first deal, and it’s awesome. At 10 stories, the Baker Tower is the tallest building in Oregon east of the Cascade Mountains. It’s a historic mixed-use building (built in 1929) with residential, commercial, and a ballroom. It’s just cool. The only downside is that it’s a six-hour drive from my house.

I syndicated the purchase to five investors, each of whom owns an equity stake, and the plan is to hold it for a while. We visited in November and plan to visit regularly as a family. My not-so-secret hope is that this becomes a place with many family memories.

Raising the funds and structuring the deal is significantly more complicated than offering private money loans on short-term flips, but the upside and impact are worth it.

Chuck!

As I wrote in June, we got a new dog this year. Chuck has been a genuine joy... despite his fondness for chewing our clothes. We all love having him around the house, going on walks, and playing fetch. It’s so fun having a dog who actually listens and does what you want (85% of the time).

One funny thing: when I’m on the couch, he’ll lie down beside me... Then he’ll put his head on my lap... Then his front paws... until he’s slowly wiggled his entire self on top of me! I think it’s hilarious and reward him with plenty of pets.

Travel

We traveled a bunch, which I love. Here are some pictures of places we visited.

Spain

As part of Jessi’s sabbatical, we visited Barcelona and Málaga. It was so wonderful speaking Spanish and enjoying some sun.

Alaska

A friend from college wanted to visit, so we went for it!

Camping In The Redwoods

We spent time with my side of the family during an extended camping weekend. So much fun. We had Chuck for about a week at this point.

Backpacking Part of the Corvallis To The Sea Trail

The kids did amazing! We hiked 5 miles each day for 2 days. I’d like to keep exploring parts of the 60-mile trail.

Tucson, Arizona

We finished the year with my family in a vacation rental. My favorite part (besides being with family) was swimming in the heated pool each day. We also got some nice family photos.

Looking Ahead

2025 was a great year, and I’m looking forward to 2026. The kids keep growing and becoming more independent (like staying home alone). We also have more travel planned (like Uganda, Mexico, and Boston) which all of us enjoy.

I'm also having a blast growing my property management company and have a great team helping me. Growing it is major focus this year because I believe we can help lots more owners and renters.

Finally, I’m listening to books that collectively span American history to celebrate the US’s 250th birthday. Right now I'm listening to George Washington's biography and next will be about Lewis and Clark. I have to listen to 40 minutes a day on average to hit my goal, and so far it's been fun.

I'm excited!