PIE failed. But it’s a failure worth celebrating and learning from.

After posting an official company perspective about the end of the original PIE early-stage startup accelerator concept — the one focused on SaaS, mobile, and other software-specific products — and revealing that PIE Demo Day 2023 will be our last demo day ever, I got a ton of feedback from folks. The majority of that feedback was, in a word, humbling. I took it all to heart. And I believe the kind things that folks have said about that program and its impact on our community to be largely true. 

So I thought I would sit with that feedback for a while. Before sharing a more personal perspective. I’m ready to do that now. With my perspective on why we need to shut down the original PIE accelerator program. And why that version of PIE was a failure. But also to share a bit more about — as many people have asked — what’s next.

Wait… What’s that? You can feel that can’t you? It’s that feeling like you’re going to get some diatribe tinged with remorse and regret. There’s just a twinge of it. A whiff. Like when a professional athlete “retires.” Or when the concert “ends” even though the band hasn’t yet played their most popular song…

That’s fair. Because usually at this point in these “I’ve decided to quit doing this thing…” sorts of posts, you, gentle reader, would expect the author to pause. To reflect once again, awash in a wave of emotions fueled by the warm glow of hazy nostalgia. Opine on the history, magnitude, and relevance of the work that had been done. And dare once again to dream about the potential of the project in the future. If only it were to continue. If only. And then to equivocate. To backpedal. And to maybe give some glimmer of hope that the decision to shut the doors was wrong. And to ultimately unquit. 

Given the world we live in, you’d expect that. But you’re not going to get that. That version of PIE is done. Done done. 

[NOTE: What follows will be a bit rambling. And may lack depth in spots. But I wanted to get it out rather than continue to dwell on it. And I feel like you’re probably comfortable with rambling from me at this point.]

The PIE software accelerator had a good run — with eight (soon-to-be nine) demo days. It was a pretty good project. And it was an inimitable learning experience. But it’s time to tie it off. It’s done. 

Why? Because it failed. It never became a sustainable business. And that’s entirely on me.

Personally, I always feel like owe it to you and to the community to be as open and honest as I can be. So long story short or tl;dr or whatever, I keep can’t help but keep coming back to this single thought: If PIE were a company going through PIE, what would we have done with it…? Would it be one of our darling case studies like AppThwack or Cloudability or Lytics? Or would we have encouraged it to simply shut down? 

To put it another way, if I were to step back and subject PIE to that same blunt and straightforward feedback I always strive to give the founders we serve, what would I say to myself?

It’s not pretty.

But it’s not just my perspective. What else would I do for PIE if it were one of our startups? I wouldn’t just take my word for it. I’d ask the community around PIE for advice. Our mentors. Our advisors. Our alums. 

So I did. I spent months doing exactly that. Throughout the pandemic. So many Zoom calls. Talking to everyone I could about shutting PIE down. Arguing really. Because practically every person I talked to encouraged me to keep PIE going. Not because it was a good business, but because it was a necessary part of the community.

Even they knew PIE was never a good business. 

So like the startups we mentor, I did what I encourage the founders to do. I graciously accepted the feedback and guidance. I assimilated the perspectives. I distilled everything down to a series of choices. And then I, as the cofounder and general manager, made a decision about the most appropriate path forward — even if it ran contrary to the feedback I had received.

I decided it was time to shut down the software-focused accelerator. And then I asked our board for approval to do so. And they validated that decision.

You see, in my mind, that version of PIE was very much a moment in time. That only appeared to work. Because of all of the other dynamics at play. It had a strong beginning. Coming out of an economic downturn. Fueled by an incredible and vibrant community. Addressing a specific need. Launching with undeniably strong partnerships. The early days of the coworking space and the accelerator program showed promise. Immense promise. 

But that didn’t make it a good business.

When I talk to folks about PIE, I often say it’s a “Benjamin Button business.” We started out moderately successful, thoroughly resourced, and well-funded. But eventually, as time went on, those partnerships ran their course, money became tight, and resources were far less available and accessible than they had been. 

In the end, the PIE software accelerator became a project that became governed more by “where we could find money” than “what we were hoping to accomplish.” It fell prey to the “culture of scarcity” in which nonprofits exist. Where there is a constant unhealthy and exacting tension between talking about the work in order to secure capital and actually carving out time to do the actual work. (Spoiler alert: Both sides of that equation failed.) It was kept alive by sheer force of will as it scraped by and struggled to make ends meet. 

And to be clear, this wasn’t a failure of our community. This wasn’t a failure of programming. This wasn’t a failure of the participants. This wasn’t a failure of the mentors. This wasn’t a failure of the conceptual model. All of those things worked exceptionally well. Throughout a variety of iterations. 

What didn’t work was the business, itself. And as with any business failure, that, my friends, was a failure of leadership and management. This was a failure of basic business.

In short, the original version of PIE — the software accelerator — never became an actual business. It waffled between a philanthropic project and an experiment in the greater good. But more than anything, it became an expensive nostalgic hobby. Something we kept doing because we’d been doing it. Something we believed we wanted to exist. A habit more than a pursuit. A habit that required me to exhaust my own personal resources, take on significant debt, engage in innumerable side hustles, and pare the program down to some bare-bones semblance of the original model simply to keep it alive. 

Not productive. Alive.

That is not good business. And if it was, clearly I lacked the vision and wherewithal to realize that potential. But I fully embraced the opportunity to drive it into the ground.

And, as such, the original PIE software accelerator is done.

But it’s not all bad. As with any failure, the primary outcome is knowledge. And that’s where the “what’s next?” comes in. We’ve been able to apply those learnings to the programmatic elements of other work we do. Those learnings from PIE will continue to live in our collaborations with Autodesk and in the Built Oregon accelerator programs continuing to, ahem, build upon what we’ve started — in very different verticals. And new versions and concepts will continue to bloom from the insights we’ve been able to share with startup communities around the world, from Leicester to Kobe.

(And if you’re thinking about starting your own accelerator program or you want to improve an existing program, I clearly have a thing or two that I can share with you about what not to do. It might even be time to work on a second edition of that PIE Cookbook.)

So a failure, undoubtedly. But a failure worth celebrating. 

With that in mind, I hope that you’ll take a few minutes out of your overly busy schedule this week to join us for the final PIE Demo Day ever. To celebrate the companies who have completed our most recent accelerator program, to reminisce about the program that was, and to engage with the community that made the entire project work — despite its best efforts to fail. 

Let’s celebrate all of those things. Because they deserve it.

Come celebrate the PIE that was. Bask in the community that is. And help us think through what the next version of PIE — or a more viable business — has the potential to be.

  1. Astrid J Scholz August 13, 2023 at 8:10 pm

    You’re both overly harsh on yourself and refreshingly clear eyed about the challenge: if we can’t build a business accelerating the things we want to see in the world, we don’t have business accelerating the things we want to see in the world. Your reflections only resonate too well!

  2. PIE was such an inspiration. Too bad.

  3. […] yeah. During this year, I took a sabbatical. I shut down the original PIE accelerator. And I started a new side project. (You know I always need a couple of cockamamie schemes I’m […]

  4. As always, a thoughtful & incisive look at the good and bad of a grand experiment. Love ya, Rick!

  5. […] PIE failed. But it’s a failure worth celebrating and learning from. […]

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