Knowing when to quit
PIE Demo Day 2023 will be our last
tl;dr It is time to end the software/SaaS flavor of PIE in an effort to refocus limited resources on opportunities that have more significant impact on the broader PIE community. But not before we take the opportunity to celebrate our software community by hosting one final PIE Demo Day.
Quitting is never fun… but it’s easier when you’re doing it for the right reasons.
Over the years, PIE has had the opportunity to work with any number of founders. Some of those founders were working on the right idea with the right team at exactly the right time. Still others, conversely, were pursuing something that wasn’t quite right. Something that was just slightly off — or completely mistimed, underresourced, or far too audacious.
It was with these founders — the founders who were most likely on the path to failure — that PIE most prided itself in helping. Not in helping those founders fix those problems or find more talent or secure funding. Not in helping them pivot. But, rather, in helping those founders stop. And quit.
And while coming to that decision — a clearly painful and potentially embarrassing decision — was likely for the best. And would save those people — those humans building those companies — undue stress, anguish, heartache, lost time, and possibly financial ruin. It was still always a difficult decision. Each and every time.
Yet we realized that quitting was helpful. And compassionate. And with practice and repetition, PIE developed an acumen for supporting those founders as they made those difficult decisions. For all of the right reasons.
Now, 15 years into the experiment, it should come as little surprise that we are once again engaged in convincing a founder to quit. Only this time, it’s the remaining founder of PIE.
This is not new. Or spur of the moment. It has been the topic of thoughtful — and sometimes heated — discussions with participants, alums, and mentors for several years. As the pandemic wore on. As the dissatisfaction of a “virtual accelerator” took its toll on staff and participants. As the economy once again tightened its belt. The community that surrounded PIE — that fueled the original version of the startup accelerator — became exhausted, spent, and completely burned out.
Because accelerators don’t create community. Quite the opposite. Communities create accelerators. PIE, itself, began because the community willed it into existence. It was a manifestation. And that manifestation was meant to focus the community and its resources in a way that multiplied the impact of each individual contribution.
PIE was designed to scale the potential of the community for the benefit of the community.
But at some point in that pursuit, PIE tipped. It no longer served as a means of enhancing the software startup community. It became an entity that seemed to exact a toll. Something that was extracting more from the community than it was contributing. PIE no longer felt like an opportunity for members of the community; it felt like an obligation. And, at times, a chore.
(To be fair, this is not a condemnation of — or even a slight toward — startup accelerators. Or the startup accelerator model. This is a unique moment in time where PIE is experiencing something within the Portland software startup community that gave us pause. And out of appreciation and respect for that community, we had to interrogate it.)
We’re concerned that the software community — the very community that manifested PIE — is fractured. It is no longer as cohesive as it once was. And we care too deeply about that community to leave it in disrepair. Our community deserves more than that. And the broader tech and startup communities deserve more than that.
Many of us — your humble author of this missive included, gentle reader — feel like we’ve lost our connectivity. And are struggling to find pathways to rekindle critical relationships. We’re hungry for opportunity. Opportunity to reconnect with old colleagues and friends. Opportunity to make new connections. Opportunity to feel grounded and at home in a place that — once familiar and vibrant — now feels increasingly foreign and lonely.
In our experience, a startup accelerator is not the right pursuit in that type of environment. PIE was built to do a different job. In a different community. But we now find ourselves in a new — and in many ways better — community. And so we need to rethink PIE. And its place in that community.
To put it in startup parlance, PIE has lost product market fit. And it’s time to reassess the market to figure out where PIE fits. And where it can do the most good.
We have work to do. We have bridges to repair. And relationships to mend. For everyone in the PIE community, new and established. Because we’re all suffering from the malaise of disconnection.
We have work to do. And that work involves facilitating connections. Establishing relationships. Fostering interaction. Inciting discourse. Inspiring creativity. Sharing knowledge. And creating space for serendipity to occur. Because it’s only through those connections that a vibrant new version of the PIE community will form.
We have work to do. In celebrating new voices and perspectives absent from the previous versions of the PIE community. In celebrating new organizers and leadership. In celebrating new examples, archetypes, and heroes — not just embracing the stereotypical examples from days past. And in continuing to support and encourage a more robust and diverse PIE community than we’ve ever had the potential to create.
We have work to do.
And all of that has to happen before we think about another accelerator program. Because accelerators are built on the foundation of community. And continuing to attempt to run an accelerator program on that faulty foundation doesn’t do anyone any good.
So we’re quitting.
But before we do… we’re hosting one last PIE Demo Day. To celebrate the current companies who are growing into the startup community. To celebrate the alums who continue to pursue new ideas and concepts. And to take a moment to bid farewell to the PIE program that started it all.
Because in many ways this ending is simply a new beginning for this ongoing experiment.
Maybe, just maybe, this final PIE Demo Day will be the start of that next phase. Maybe, just maybe, this will be one small spark that helps ignite the beginning of the next great version of our community. Maybe this event is the opportunity that connects the founders of the next great software startup in our community. Maybe this is the opportunity to reunite members of the community and repair those fractured relationships.
Yeah, maybe. But to find out, we have to quit.
