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Investing $125M in downtown Portland garners Jeff Swickard two buildings… and a new UpStart tenant

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.

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Marshall Kirkpatrick is back with a new offering to help you make sense of the Web

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.

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Silicon Florist links arrangement for February 26, 2026

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.

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Silicon Florist links arrangement for February 25, 2026

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).

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