Your Art Can Go in This San Francisco Alley

Last year, a couple in San Francisco accidentally paid way too much money for a dirt road. On an auction bid starting at $1, they put down $25,000, thinking they were getting a screaming deal on a parcel of developable land right next to their house.

They won their bid, but quickly learned that what they bought was actually just a narrow 82-foot long easement alongside the house that nothing could be built upon. They had paid all that money for a dirt path.

“I couldn’t insure it,” says JJ Hollingsworth, the alley’s then-reluctant owner. “It was just a big liability hanging over my head, and it caused me a lot of concern and stress, oh my gosh.”

After reading about Hollingsworth’s story in the San Francisco Standard, three local “tech pranksters” offered to buy the alley from Hollingsworth. The trio includes software engineers Patrick Hultquist and Theo Bleier, along with Riley Walz, a recent OpenAI employee who helped create Jmail, a repository of all the emails in the Jeffery Epstein files formatted as a more user-friendly Gmail-esque inbox. The three of them have also worked on Pursuit, a citywide scavenger hunt that has taken place across San Francisco for the past two years.

Together they paid $26,000 for the property, then put up another $10,000 to pave the road. Now, they intend to put some art on that ground. For help doing that, they are enlisting any and all online artists they can.

Announced today via a tweet by Walz, Paint a Street is a website that lets users submit low-resolution digital drawings for use in the project. The submissions will eventually be arranged in a collage made up of 6-by-6-inch squares per art piece. Users can then vote on the different art pieces, upvoting or downvoting them to rank them in the collage.

Submissions and voting starts today and ends on Tuesday, April 7. The top 1,280 squares will be the ones officially placed on the pavement, and the entire installation will stretch the length of the 80-foot paved road.

“We want to let everybody, the whole internet, paint this street,” Hultquist says. “It's going to be this supercool sort of collaborative art project.”

The project is inspired by Reddit’s r/place, a 2017 April Fools’ joke turned community art project that allowed users to change a large digital canvas a single pixel at a time. The result was a chaotic canvas of images, memes, and inside jokes.

Paint a Street will be more tightly curated. Images show up on the website as small tiles, and user votes serve as the mechanism to move them around and determine the final order. Each submission will also be reviewed by an AI content moderation program that flags inappropriate images. Anything that gets flagged will then go through a manual review.

Technically, the resulting collage will not actually be painted on the pavement but will be placed as a large sidewalk decal. Hultquist says the ultimate goal is to make the alley a place people want to go, potentially becoming an SF tourist attraction.

For Hollingsworth, this art project is the best-case scenario for her expensive dilemma. “They told me that the art was intended to bring people together, so that's a good thing,” Hollingsworth says. “I want to be part of that.”