WTF is wrong with the Portland startup community?

I get one question, consistently. The same question that I get asked — time and time again — exponentially more than any other question. It doesn’t matter if it’s someone who was born and raised in Portland or if it’s someone who just moved here. It doesn’t matter if they are super well connected or don’t know anyone. It doesn’t matter if they’re employed at a major corporation or if they’re out starting their own thing. And it’s one of those questions that seems to confound practically every single person who has an interest in entrepreneurship or startups around here. And that question stuck on incessant repeat is this: How do I get connected with other people in the Portland startup community…?

Honestly, I get this question so much, I sometimes wonder why I even refer to it as a “community.” At times, it seems to be more of a loosely amalgamated group of individuals banging about in discrete silos — or worse yet, all alone — who just happen to share a particular geographic region in common. Like an office building full of people in different businesses who vaguely recognize one another from the elevator but who never talk and never collaborate and never connect. Who for all intents and purposes lack the actual connectivity to make the community an actual community.

And that’s frustrating. Because I know all of these organizations and event organizers and mentors and investors and individuals who are all doing their part to connect people to the local startup community and other resources and one another. People who volunteer their time to make the community a more accessible and collaborative place. People who are paid to create the programs and infrastructure to support founders and startups. And a plethora of people who are always willing to jump on a Zoom call or grab coffee with anyone who asks. All as part of an effort to ensure that startup folks or the startup curious can get access to the support and resources they need.

And I know that these individuals who are asking me this single question have somehow managed to find their way to me. That they’ve at least found one toehold or access point in the proverbial community. That they’ve at least figured that much out — likely with way more effort than necessary. And more roundabout and inefficient way than need be.

But I also know — even with that connection point — that I can’t provide all of what they need. Often, I can’t even provide a semblance of what they need. As much as I want to. I need all of those other organizations and individuals and all of the value they provide. I need a safety net for the people who have found me. Rather than a laundry list of other organizations and people they need start working to chase down.

Because for a community to actually work, it takes collaboration. Not some semblance of collaboration. Not talking about collaboration. Collaboration. Intense collaboration. And committment to that collaboration.

But most of all, it takes something to align and aggregate those collaborators. It takes a front door. Or a campfire. Or a hub. Or some other platitudinal analogy that speaks to being the first stop that anyone, anywhere recognizes as the starting point of their journey. And that everyone in town knows and promotes and shares.

But for all of our talk about collaboration and connection and collegiality, that does not exist for Portland. I could write a dissertation on why I think that is, but that’s not really the point. (And if you want even more of an earful about how frustrating this is, grab some time with Stephen Green.)

Instead, people enter — or struggle to enter the community — through a variety of sidedoors or random connections or disorganized bandying about. Sometimes they make it. More often than not, they get frustrated. Or they give up completely.

And I don’t blame them. At all. It’s an inefficient and frustrating morass. And it’s a study in making something much harder than it needs to be. Worst of all, it’s not conducive to community. In the least. It’s corrosive.

That’s why I have been somewhat heartened by some recent efforts at the state level to start to resolve some of these issues. To fund collaboration and infrastructure to make “getting connected” less of a chore. And to ensure that organizations and individuals alike have easy access to the support that they need.

You know, like actually have a community. Who knows, someday we might even gasp have a “startup ecosystem.” But I’d settle for community at this point.

Yes, we’ve been here before. Likely multiple times. But you know me, crazy optimist. It’s just at its beginning stages. And there’s still a long, long ways to go. But it’s a start. And your input is critical. So I’d like to ask for your help.

I know we’re all survey weary. I get that you’ve been asked these same questions time and time again. And I think I’ve managed to intimate that I share in your frustration. (If not, I can rant for a lot longer.) But if you’re willing, I’d love to hear from you one more time. Or the first time. Or the last time. With the hopes that this time we actually do something with your feedback.

If you’ve got a couple of minutes — maybe this weekend — I implore you to share your thoughts about what’s right with the Portland startup community and more importantly what’s wrong and needs to be fixed. And ask your peers — or your limited connections with the community — to do so as well. Because I want you to have access to the community you need. And a bunch of other people do too.

Or don’t. And we can just continue fumbling through the frustrating status quo for generations to come.

Please and thank you.

[Full disclosure: PIE is part of a working group that is focused on creating an “innovation hub” for the Portland metro area. I am the cofounder and general manager of PIE.]