3 Oregon Substacks Worth the Space in Your Inbox

From hot Blazers topics to Dear Sugar to Oregon deep dives, these newsletters are worth the subscription. (And one of them is completely free!)

By Julia Silverman August 17, 2021

The age of the subscription-based email newsletter is upon us all, Portland. 

Close observers of the media kind are likely already familiar with Substack, the newsletter platform that cuts out the middleman between writers and their would-be readers.

Like the innumerable mattress-in-a-box companies who ship directly to your house, or Airbnb allowing you to bypass hotels and rent directly from homeowners, the idea is to create a direct-to-consumer situation (that unlike the blogs of yore, makes it possible for its creators to earn a living). Substack makes it a snap to email thousands of people at once, for free; if writers want to charge people a monthly fee for the privilege of reading and/or listening to their musings, the company takes a relatively hefty 10 percent cut.

The dawning age of the subscription newsletter has produced a handful of superstars already, from former Buzzfeed tech and culture writer Anne Helen Peterson who dissects everything from the Portland BLM protests to the mysterious popularity of the nap dress to progressive historian Heather Cox Richardson, who meticulously, patiently explained the waning days of the Trump administration to a bewildered nation. 

Now, a handful of notable Portland/Oregon based writers/collectives have begun making inroads on the platform too. Here are three notable local newsletters that deserve a place in your in-box.

The Oregon Way

A rational exploration of Oregon’s common underpinnings in a time of extreme polarities (for an example, look no further than the vaccination rates in Southern Oregon versus the metro area, and the resultant compassion fatigue as Portland-area hospitals fill up with patients from far outside the Willamette Valley.) There’s not a lot of partisanship here; the tone is more collaborative and straightforward, and the contributor’s list is a who’s who of the Oregon political scene. Come for the weekly round-up of behind-the-scenes political news; stay for the searching, thoughtful analysis like longtime pollster Adam Davis’ recent ode to once and future Portland. Cost:$10 a month/$110 a year gets you bonus content, like the thorough weekly newsletter and invites to events. You can read all opinion articles and the weekly digest for free, though.

Dear Sugar

Maybe Cheryl Strayed, author of Wild and the constant giver of the sagest advice via her long-running Dear Sugar column belongs to the world now, but she still lives here in Portland. She took a break for a bit, but Dear Sugar is back now, and in your inbox. The queries are instantly recognizable to most people—should you in fact send a birthday card to the family member who is a clinical narcissist?—but the answers are, as always, what sets Strayed apart from the world’s garden variety Dear Abby wanna-bes. She gets personal, provocative, elliptical—there’s an answer in there, sure, but it needs to be teased out, and that’s half the fun. You can also find more intermittent new writing from Strayed.
Cost: $5 a month. And if you’ve got a burning question for Dear Sugar, email her at [email protected]

Blazer Banter

Yes, it’s true, even in our small market, everyone has a take on the Trail Blazers. There are no shortage of podcasts, radio shows and armchair quarterbacks eagerly dissecting Dame and friends. So why pay for this one? Writer Erik García Gundersen, the former Blazers beat reporter for The Columbian,  has real chops—he’s written about basketball for the New York Times, the Associated Pressand USA Today, and his approach to the team is refreshingly free of hyperbole or hype. Don’t miss his portmortem on the Blazers’ disappointing summer.
Cost: Free! (For now.)

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