Turns out, when I said Portland Startup Week had “a whole bunch of AI stuff in a variety of flavors” and then didn’t list any of it that — surprise — people actually wanted a list of AI events that are happening next week. Fair. Happy to oblige.

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

AI best practices: If at first you don’t succeed, prompt, prompt again – GeekWire

What follows is practical advice on how to use AI as a power tool rather than a slot machine. For a simple request, it’s overkill, but if you’re serious about prompting, read on.

Our friends at Latino Founders just opened applications for its Next Wave Startup Lab — Climate Edition — a 3-day crash-course-style workshop running May 29–31, 2026, in Portland. Applications are rolling, but they close the same day the workshop kicks off.

I have a habit of forgetting things. Especially big things. The kind of things that you’d think should be hard to forget. Like nine-figure funding rounds. But that, kids, is why I write things down. So when Panthalassa raised $140 million today, it got me thinking — how does that actually stack up against the largest rounds I’ve covered on Silicon Florist over the years…?

I have a habit of asking around about startups in town. Who should I be tracking…? Who is the most underrated startup…? What’s going to be the most impactful startup…? And time and time again — over the past few months — one startup has consistently come up: Panthalassa. Now, we have more context as to why. They just raised $140 million.

Portland Startup Week 2026 takes place May 11–15, 2026. With 50+ startup events across the week in Portland and throughout the Portland metro — and the calendar still growing hour by hour — this is the moment to figure out which Portland startup events you’re actually going to attend. If you’re a Portland startup founder, an investor curious about the Portland startup community, or a startup curious type who just wants to know where the energy is during Portland Startup Week, here’s your cheat sheet.

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

Connecting the wisdom of Yoda to the building of startup communities | by Mitch Daugherty | Built Oregon | Medium

Most startup communities are open, willing, and collaborative by nature. No different Oregon is. There is a passion amongst the founders and support organizations to work together and accelerate their local and regional economies. But creating change, and being able to determine how best to engage and accelerate, is something that requires several commitments.