Month: June 2025

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

Prosper Portland announces Cornell Wesley as agency’s next Executive Director – Prosper Portland

Following an extensive national search, Prosper Portland is pleased to announce that Cornell Wesley has been selected as the next Executive Director of Prosper Portland. Prosper Portland’s Board of Commissioners will consider his appointment at their Wednesday, July 9 Board meeting.

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

“We Are Still Underreacting on AI” – Pete Buttigieg

Over the last few weeks, I have been spending more time studying artificial intelligence, the people working on it, and the activity around it. As I’ve done so, it has become clear to me that—even with all of the media attention and public interest in this topic—we are still profoundly underreacting, and we are dangerously underprepared.

I’ve talked to a few folks about this. And maybe mentioned it on the show. But I wanted to be sure that you knew about it, as well. The gist is this: I wanted to revisit all of the Portland and Oregon startup news that’s happened so far in 2025. And so I was going to rewatch all of the 2025 episodes of my weekly recaps to catch up. And then I thought… why do that alone…?

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

The Founder’s Communication Cadence: Weekly, Monthly, and Annual Habits That Drive Results

I believe it’s critical for a CEO to be an effective communicator. They must convey their vision and strategies externally to customers, influencers, and investors, as well as internally to their teams. One of the most impactful ways to do this is through written communication, such as monthly investor updates, internal goals, project updates, or annual shareholder letters. This becomes especially vital during times of change when alignment and motivation are paramount.

I’m glad you asked. Otherwise, sharing this information that I have right in front of me would seem a little weird. But since you want to know. I’m happy to share who won the 2025 edition of TiE Oregon Columbia River Pitch, the competition among startups in Multnomah County, Oregon, and Clark County, Washington.

If I’ve heard it once, I’ve heard it a thousand times: “Why is it so hard to connect with people in the Portland startup community…? Am I missing a regular event or something.” Unfortunately, no. The answer isn’t as easy as that. But it does stem from the sort of secret hack that people tend to meet one another one-on-one for conversations. Rather than leaning on traditional “networking” events.