So, here we are

We’ve wanted to put The Timmy Times together for a long time. I kept collecting ideas, tinkering with sections, and telling Kerry, “Okay, I think this is it.” At some point, you have to go for it. So here we are.

Once a month, you’ll get a little of our world. A neighborhood discovery, a person or small business worth knowing, a few things to do, and one useful thought about real estate. There will probably be a cat photo, but I make no promises that the cat will be helpful.

Montavilla is where I say hello to my neighbors, but our community lives all over the Portland area. With your help we will wander from Multnomah Village, to St. Johns, to Sellwood and beyond. This issue is the jump off, but from here, you’ll help to shape it.

A big shout-out to my wife, Kerry, for coming up with the name The Timmy Times and helping bring this newsletter to life.

Behind the Sign is where I share what happens between the real estate showings, contracts, client calls, or occasional unrelated Timmy side quest. I call these Timmy Tumbles, and here’s a little preview of the stories to come:

• Trying to get into a condo showing through a gated parking garage like it was Mission: Impossible.
• Getting my ninth buyer’s offer accepted to stay on track with my goals this year. Every day I’m hustlin’.
• Dropping everything to fix a friend’s malfunctioning automatic kitty litter box while he was at Burning Man. Real estate was somehow the easier part of that day.
• Meeting the people doing good work in neighborhoods around Portland through my role on the METBA board.
• Discovering one of my newest clients found me through a Reddit post. Thanks, internet.
• My ongoing attempt to understand AI so it understands me.

Never a dull moment.

These are the moments, though, that make every day unique.

Average sale price as a percent of list price. Same neighborhood, two windows.

If you’re thinking about selling next year, the useful question right now isn’t what your house is worth. It’s what needs to happen between now and then.

Source: RMLS, Montavilla closings, March 4 to May 27 and June 2 to August 31, 2026.

Tattoos, local art, and an all-ages storefront on Stark. Coming up: Montavillains, a monsters and villains art show, Saturday, October 10, 6 to 10 p.m.

Of all the places you could have opened your business, what made you choose Montavilla?

My wife lived here about six years ago, and whenever we walked this stretch, we’d say that if we ever opened a business, we wanted it to be here. It has a small-town feel within the city and still feels like a part of Portland people are discovering. When this space became available, it was exactly the block we wanted.

What do you love about being part of this neighborhood?

The businesses are really supportive and look out for each other. Between the bars, vintage shops, and farmers market, there’s so much good stuff packed into just a few blocks. A lot of what people love about Portland is represented right here.

What’s something about your business you wish more people knew?

We’re more than a tattoo shop: we have seven tattoo artists with different styles, cosmetic tattooing, hand-painted nail art, and tooth gems. There’s also a little shop with art, thrifted finds, and T-shirts, plus a gallery where we aim to host a show each month. Kids are welcome to come in, too.

• Southbound I-5 at the Rose Quarter should reopen around mid-October. Your 405 detour is almost over (KPTV, Sept. 24).
• Leaf Day runs Nov. 9 to Dec. 21. Look up your date on PortlandMaps and move your car, or pay $422 for the tow (Portland.gov).
• The Portland Fire drew about 14,000 fans a game in year one, fourth in the WNBA. Portland showed up (OPB, Sept. 26).

Here’s a sneak peek at the November issue:

• Why winter could be a strategic time to look for your next home.
• Local gifts, neighborhood shops, and markets worth exploring.
• A holiday favorite.