News from Pickathon HQ over the past year has been almost entirely positive. The 2024 edition of the festival was another success thanks to killer performances from another impressively diverse lineup that included Bonnie “Prince” Billy, jazz explorers Irreversible Entanglements, psych rockers JJUUJJUU, and folky singer-songwriters Jess Williamson and Joanna Sternbert. Additionally, the fest’s organizers secured a permit last February that will allow the event to remain at its current home at Pendarvis Farm for another decade. 

The overall good vibes that tend to exude from the annual gala is perhaps why it felt so alarming to see a recent blog post on their website that carried the headline, “Pickathon Is At A Crossroads.” Then came an emailed survey asking previous attendees if they’d be willing to suffer the presence of visible corporate sponsorship or the arrival of single-use cups and dishware, followed by an email appeal asking folks to help the festival’s offshoot nonprofit Creative Neighborhoods raise $1 million by the beginning of March. 

If this has started alarm bells ringing in your head and heart, Pickathon founder Zale Schoenborn would like to quiet them. 

All of the above is a systematic approach that Schoenborn and his team have been taking to stress test some new ideas that might help the festival survive long enough to enjoy another 10 years at Pendarvis Farm. And as with many 12-step programs, the first move was admitting that they had a problem. 

“That caused a lot of ripples in the water,” Schoenborn says. “We really needed to let everyone know that we had some decisions to make. We knew our expenses were wack, and we couldn’t continue to go down the same path. The options were: Do we jump in and assume everyone is on board and we need to do a fundraiser, or do we start at the beginning and walk through this step-by-step and see what everyone’s values were?” 

The bottom line is that Pickathon is carrying a lot of debt. Due to the pandemic, the festival managed to survive having to cancel the 2020 and 2021 editions with money in the bank. That gave the team enough confidence to develop the Neighborhoods concept that brought art installations, a farmers market, an area for massages and sound baths, and various hang out spaces. It all helped add greatly to the appeal of an already appealing event, but it also added a great deal of stress on Pickathon’s finances.

“Over the last three years, we’ve accumulated close to half a million in debt,” says Schoenborn. “If we just kept it going this year, we’d be pushing another $350-400,000.”

How to make sure that Pickathon doesn’t get sunk deeper in the red? That’s where the survey came in. Sent out to a few thousand folks who have attended the festival in the past, the inquiry set out to find if the event should stay as it is or if folks would be willing to accept cost-cutting changes like more generic stages, a smaller festival-friendly lineup, or pricier food and beverage options.

Surprising no one, the 1,600 people who took the survey overwhelmingly preferred to keep Pickathon exactly as it is—something that Schoenborn and his team assumed would be the case. 

“We hoped,” he says, “but we didn’t want to pollute it. We needed this to tell us one way or another. We weren't going to be offended if things went the other way. It’s way too much work to fight for something if not everybody wants you to fight for it.” 

All well and good, but that doesn’t solve the problem of how to make the festival happen without losing money on materials for building the neighborhoods and the many, many free passes they give away to the volunteers and mentees that bring those stages and experiences to life. Hence shining a brighter spotlight on Creative Neighborhoods and looking to raise funds for the nonprofit to defray some of those overhead costs for Pickathon 2025 and beyond. 

So far, it’s been a bit of a tough sell. In the three weeks since they announced the fundraising campaign, they’ve only netted just over $14,000 in donations. That number could tick up more now that early bird tickets to this year’s event have gone on sale, with a “Support Creative Neighborhoods” option that will funnel your payment for a weekend pass to the nonprofit. 

The only unknown is what happens if Creative Neighborhoods doesn’t hit that $1 million mark by March 1. Schoenborn isn’t worrying about that just yet, but is prepared to beat the bushes as the deadline begins to loom larger and larger. 

“We have to stay hopeful,” he says. “We’re really hoping to tap into the folks with means that think Portland needs a win. We’re in a renaissance, right? We’re coming back and institutions like Pickathon absolutely have to be a part of that. If we became hollowed out, we’d be just another concert that could happen in any city anywhere.”