Portland Oregon startups, tech, news, events, jobs, and community

If you live in the Pacific Northwest, you can’t escape the news cycles about downtown Portland. Sometimes, you can’t even escape the news cycles nationally — depending on who is carping about the Rose City. But it’s not all doom loops, my friend. Any number of folks are hard at work, reinvigorating Portland’s city core. Like Jeff Swickard. Who snapped up the iconic Big Pink. And the building next door. In a big vote of confidence for downtown Portland. (And spending about $125 million to do so.) And now, thanks to those efforts, he’s landed a very startuppy UpStart tenant for his property.

I’ve had the pleasure and privilege to follow Marshall Kirkpatrick through any number of his online chapters. First, as a fan of his blog. Then following his career as the first hire at a young upstart blog called “TechCrunch.” Then I had the opportunity to work for him at Read Write Web (RIP RWW). And finally, I had the chance to hang out with him every single day as his startup Little Bird went through PIE.

Here’s a roundup of interesting startup links I came across today:

The 2026 Global Intelligence Crisis – Citadel Securities

Despite the macroeconomic community struggling to forecast 2-month-forward payroll growth with any reliable accuracy, the forward path of labor destruction can apparently be inferred with significant certainty from a hypothetical scenario posted on Substack: The 2028 Global Intelligence Crisis.

Here’s a roundup of interesting startup links I came across today:

What I Learned from Turning Myself Into an AI Chatbot | Jane Friedman

Soqratic took care of creating a simple interface so my potential clients could easily sign up. As it turned out, one of the biggest challenges was to make sure that the virtual coach’s answers were limited to my content. I didn’t want it pulling writing and publishing advice from Anne Lamott or Jane Friedman and passing it off as my own. The solution to this is a technique called RAG (retrieval augmented generation), which limits answers to content from a bounded data set (in this case, my books and blog posts).

If you’re a startup founder in Washington County, one of the best ways to get rapidly connected to the community is to participate in TiE Oregon’s Westside Pitch, now in its fifth year.

Here’s a roundup of interesting startup links I came across today:

The Fundraising Tactic AI Startups Are Using to Juice Valuations – WSJ

But several VC investors and outside accounting professionals said the back-to-back or multitiered deals are novel and raise questions about how much startups are really worth in an age of frenzied artificial-intelligence investing.

Here’s a roundup of interesting startup links I came across today:

The Last Durable Moat: Emotional Market Fit

Moats that depend on speed, optimization, pattern recognition, and scale are dying, thanks to AI, automation, and rampant access to everything all the time. Advantages based on trust, community, identity, and transformation have more staying power.