An experiment in heartbreak: PIE Demo Day 2020 moves to online, only

I thought I was going to have to cancel the very first PIE Demo Day.

Not in one of those, you know, hollow-threat-coach-voice-yelling “If you startups don’t get your acts together, we’re going to have to cancel demo day!” kind of way. Not at all. I thought we were going to have to cancel it because of forces beyond our control.

I can remember it clearly.

Back then, the first PIE Demo Day was slated to be held at the Bagdad Theater on Tuesday, January 17, 2012. Honestly, I have a hard time remembering why we even picked that date. But I can remember every single moment of it. Vividly. Especially waking up.

I’d given myself permission to sleep in. Since we didn’t have to be to the venue until 9:00AM or so. And as the morning light filtered in, I started to wake up. Squinting contactless into the white blur that was my bedroom window. Seeing movement in that blur. Squinting a little harder before rocking up onto one elbow. Enough to notice flakes of snow drifting by.

“Oh snow,” I thought. “That’s nice.” And rolled over to snooze a little more.

Cue cold sweat. Eyes snapped open wide. Bolt upright. Snow? SNOW?!!?

My next thought? “We’re going to have to cancel PIE Demo Day.”

Now, for those of you not in the know. Or who are new in town. Portland freaks out when it snows. Freaks. Out. Like crazy freak out. Like mass hysteria. Completely illogical. It’s a thing.

But despite that initial trepidation. And the portending snowpocalypse. We didn’t cancel. And it stopped snowing. And folks made it to PIE Demo Day safely. And the startups pitched. And PIE managed to get its inaugural demo day in the books.

But it would have been so much easier to cancel back then.  Because I was naive. And didn’t even truly comprehend what a demo day was. At all.

Back then I mistakenly assumed it was all about raising capital. Because I didn’t know any better. 

Now I know that startup accelerator demo days are so much more than that. And PIE Demo Days are way more than that.

And yet, oddly enough, even with that knowledge today, this type of pandemonium feels familiar. Especially right about now. Especially in the context of PIE Demo Day.

Because I’ve just had to cancel PIE Demo Day 2020 due to concerns about COVID-19 Novel Coronavirus.

Those who know me, know I don’t relish standing up in front of folks. They recognize that I have an overly aggressive reticence for taking to the spotlight. Or to being handed the microphone. They know I’d much rather be behind the scenes. Helping speakers find the right words. Or suggesting the appropriate image for a deck. Or working to find the turn of phrase or gimmick that helps a speaker more effectively connect with the audience. That’s where I thrive. Behind the curtain. Not in front of it.

And as such, those folks are probably imagining that this cancelation has me breathing a sigh of relief. Or my face contorting into a familiar emoji like 😅 or something. Or feeling like I’ve had a weight removed from my shoulders.

Admittedly, with any number of other events, this would be absolutely true. I’d be relieved. Calmed. Perhaps, even happy. But right now at this moment, I’m far from that. In fact, if I’m being honest, I’m currently sitting here trying to not ugly cry at the prospect of shuttering this live production for these folks I’ve come to know, appreciate, and cherish over the last few months.

I may hate being on stage. But I love this event.

Because PIE Demo Day has become a quintessential part of the PIE experience. For both founders. And staff. And the fact that both of those groups of people have to miss this opportunity is depressing and utterly heartbreaking.

For PIE founders, they’ll be missing out on the one true shared experience that every single PIE founder has. The keystone. The one instance where every single founder who takes the stage gets to experience something in common. Which is a rarity for PIE founders.

But they all go through the same class, you say, how can that be? Well, for the most part, the founders have similar experiences. Sympathetic experiences. Where they have some semblance of doing the same thing. But PIE is an independent study. With different paths and benefits. Support that comes on a company by company basis. Almost on a founder by founder basis. And because of that very few founders happen to experience PIE in exactly the same way.

But demo day — and the weeks of pitch practice leading up to it — are a commonality among every founder who has been part of the PIE accelerator family. It’s the one singular thing on which every single PIE founder can truly empathize.

It’s a rite of passage.

But it’s not just the startups who lose in this situation. It’s the staff. From our perspective, we’ve always treated demo day as a platform for experimentation. We’ve always tried to push new ideas. And think about the experience differently. What if we provided movie snacks to attendees? What if we livestreamed it so more folks could attend? What if we brought in a live band like some wacky late night talk show? What if we simulcast the event in various venues around Portland? What would happen if we used a DJ instead of a band?

Truth be told, PIE Demo Day has always been a place for experimentation. I just didn’t expect the experiment to take this sort of turn.

And maybe that’s because this event was shaping up like every PIE Demo Day before it. It had already sold out. And a waitlist had started. The chatter about the event was beginning to build. Founders had moved from the “pitching is easy; I pitch all of the time” to “what have I gotten myself into?” to “I’m starting to think I can do this.”

By all previous experience, we were on track. Right were we should have been at this point in time. And yet, something was off.

It had started as a murmur. With talk of delays at factories and the like. And then it continued to swell into a dull roar as local events like WordCamps started to cancel. Then global events like Mobile World Congress decided to cancel.

And then we started contingency planning. Exploring the very real possibility that the in person PIE Demo Day tradition could be in jeopardy.

And then Google I/O and f8 and a number of other events canceled. And we ramped up those contingency discussions. As we realized that the odds of canceling PIE Demo Day were only continuing to ratchet up.

And then SXSW was forced to cancel. And then the Oregon governor declared a state of emergency. And that one—the latter—also just happened to be one of the triggers I had pegged as something that would move PIE to DEFCON 1.

And so we made the decision. It wasn’t easy. But we made it. PIE Demo Day 2020 will be an online only event. No in person. Because that is the best and most reasonable course of action to ensure the safety of our founders, mentors, investors, media, and the community at large.

And so, with that in mind, I began processing. By typing…

In the wake of the COVID-19 Novel Coronavirus outbreak, PIE and its partners have made the decision to cancel the traditional in-person PIE Demo Day, slated for March 19, 2020, at Revolution Hall.

There are any number of reasons for making this decision. The primary reason is our effort to ensure the safety of the Portland startup community. Of equal concern was — given the current atmosphere of anxiousness and fear in which we find ourselves -an ever increasing lack of ability to create an event that truly reflects the positivity and support that has become the hallmark of PIE Demo Days. We truly didn’t feel we could achieve the tenor to which our community has become accustomed…

And then my marketing lizard brain went into overdrive. “This isn’t a negative,” I lied to myself. “Far from it. In fact, if we livestream it and promote that heavily, it could be the biggest PIE Demo Day ever.”

But then reality kicked in.

Livestream is a challenging format. At best. And I couldn’t put our founders in that sort of situation. It wouldn’t be the right thing for them. It wouldn’t build them up. In fact, it was more likely to create additional stress for them. And as an organization that had prided itself on “Building better founders” for more than a decade, that proposition suddenly felt disingenuous. If not outright wrong.

And so I suddenly knew what we had to do. We had to cancel in person PIE Demo Day—and any semblance of live PIE Demo Day—because there is no way that it could have ever managed to be a PIE Demo Day. Let alone the PIE Demo Day that these founders—whom I’ve had the privilege of getting to know—deserve.

And that realization crushed me.

Without mincing words, PIE Demo Day is one of the most beloved activities I get the opportunity to share with the Portland startup community. I’m really fucking precious about demo day. Truly. And this was an incredibly difficult decision for me. It broke my fucking heart.

And for all of the things I’ll miss about the in person event. For all of the great in person connections. For all of the happiness. For all of the joy. And support. For the whole vibe of that room when for one brief moment in time everyone wants to support one another. And for that rare moment where the Portland startup community truly gets to celebrate itself.

For all those amazing and magical things I’ll miss, the one thing I’ll miss most is being backstage. Behind the curtain. Supporting startup founders.

If only for missing the pep talk I’ve had the opportunity to deliver to presenters over the years. It’s become a bit of a weird tradition. And as a dumb jock and former soccer and lacrosse coach, I practically can’t help it. Big events call for pep talks.

It’s like a rule or something.

And so, the pep talk that begins “Stop. Take a moment. Take a moment to enjoy this. Because this will be the most fun you will ever have with your startup. Seriously. Everything else will pale in comparison to this. This is the only time in the life of this company where you will walk into a room filled with hundreds of people who are truly invested in wanting you to succeed and who are waiting to hear how they can help…” will have to wait for another demo day.

And that hurts.

But, I still believe it is the right thing to do. And I’m sorry if it causes any undue stress, anguish, or conflict for any of our founders or anyone in our community. It was the call I had to make.

And so that’s that. We’ll move to an experimental online version of demo day. And our founders will share their amazing stories. And our community will most definitely tune in. And we’ll all definitely learn something along the way. Portland Incubator Experiment indeed.

In closing, I find myself motivated to write this piece—venting my spleen, as it were—for two important reasons. Selfishly, writing is a form of catharsis for me and—despite any verbal bravado I might project—I’m still very much working my way through this decision. But I remain hopeful that the other reason carries equal weight. I know for a fact that there are thousands of other event organizers struggling with very similar questions and decisions in this new reality. And if my sharing the pain of canceling this event helps give the courage or insight to act, then all of this has been worthwhile.

Take care of yourself. And your people. And I sincerely wish you the strength and insight to make these kinds of hard decisions that ensure a more resilient and sustainable community for all of us. I’m sorry you have to make these decisions, but I have the utmost respect for those of you that do.

For more information about preventing the spread of COVID-19, please visit the official CDC Prevention Web site.


I always hate when I come up with better headlines in my tweet to share the post 😂