By Matthew Gerring

If you’re a regular reader of Street Sheet by Coalition on Homelessness, you might be surprised to hear that the paper’s recent upgrades — full color front pages and a new website — were sponsored by the same people who brought you AirBnB: Silicon Valley’s preeminent startup incubator, Y Combinator.

But donating to the Coalition on Homelessness was definitely not Y Combinator’s idea.  They were compelled  to give a $20,000 donation to an organization that actively helps homeless and low income people, as a result of a prank played by tech CEO, noted internet troll, and self-described “stirrer-up of shit”, Maciej Cegłowski.

Cegłowski is the founder of an internet bookmarking service called Pinboard, and aside from paying his own bills, the company is a standing protest against the venture capital funding model, in favor of what he describes as “long-term sustainable businesses that aren’t trying to take over the world.” 

He frequently criticizes startup culture through his blog, public speeches, and by trolling tech industry figures via the official Twitter account for his business.

Cegłowski doesn’t mince words. At a recent public appearance, he told his audience: “Tech companies are run by a feckless leadership accountable to no one, creating a toolkit for authoritarianism while hypnotized by science-fiction fantasy.”

“[There’s] so many fish in that barrel,” he said. “Someone’s gotta do it.”

Maciej Cegłowski

In 2016, Y Combinator ran an experiment on Hacker News, a message board it runs, where the community voted for three very early-stage startups to receive funding. Cegłowski entered Pinboard into the running, in spite of it being 7 years old, profitable, and having no plans for expansion.

“I thought it would be good to have a viable protest vote,” he said. “And I succeeded a little too well.”

In fact, Pinboard received nearly twice as many votes as the nearest runner-up. He said he has no idea why.

“Some people just wanted to see what would happen if they kicked the beehive, including me,” he said. “Maybe some people thought the business was a genuinely decent beneficiary of that sort of funding, or they wanted to see me grow — that last group I feel bad about.”

Y Combinator tried to disqualify him for violating the spirit of the contest, but after an outcry from the Hacker News community, they agreed to give him the money. Which left him with a dilemma.

“[If] I take the money and put it in my pocket, I look like I’m just an asshole,” he said, so it was obvious to him that the money should go to helping homeless people, and in particular, the Coalition on Homelessness.

Street Sheet by the Coalition on Homelessness

“[I’ve] been frustrated with how little of the startup wealth that gets made has gone back into the actual physical community,” he said.

“I lived in the Tenderloin, and I’d take the bus through, and… that transition from tech land to the Tenderloin was so abrupt and painful, and it never got better. All the companies I worked at got huge, but it never changed.”

www.ycombinator.com

So Y Combinator cut a check for $20,000. It arrived at the Coalition looking like an automated payroll check, without any note, explanation, or even contact information.

To the the Coalition, it was a complete mystery — none of its staff or volunteers had ever heard of Y Combinator, despite its heavyweight status in the tech industry. Development coordinator Lesley Haddock said the name “sounded made up, or like, a typo.”

The Coalition rarely gets donations that big, and almost never from tech companies, much less VC firms — at most, Haddock said they receive small amounts through employee matching programs. They looked up Y Combinator, and despite not really understanding what it is or what they do, sent them a thank-you note, and tried a few more times to follow up. To this day, more than a year later, they said they haven’t received a response.

Cegłowski, who’s lived in San Francisco since 2006, said he learned about the Coalition just last year after reading about the meeting between its executive director, Jennifer Friedenbach, and Greg Gopman, a startup founder who achieved infamy in 2013 with a vicious rant against homeless people in San Francisco.

Gopman returned in 2015 with a plan to rehabilitate his image, by building a tent camp with geodesic domes, but only for “highly employable” homeless people with no substance abuse or mental health problems, and met with organizations like the Coalition to pitch the idea.

Friedenbach said their meeting didn’t go well.

“I was explaining to him that there’s all these people in the community that are already working on these issues, [and] the best thing to do is to support what’s happening,” she said. “That did not seem to resonate with him — it was very clear that he felt like he knew that he could do things better.”

Cegłowski said when tech companies get involved with trying to solve social problems, they’re too often not willing to do the “scut work” of engaging with institutions that understand the problem well and have been working on it for decades.

He calls this mindset “programmer’s disease” — “The problem with programmers is that we’re used to these deterministic environments that we fully control, and we can do clever things with them,” he said. “We start to think that the whole world operates that way, which, it’s not, it’s a much messier and less predictable place, and there’s a lack of humility as to our own capacity.”

He cited Y Combinator’s research into building new cities from scratch as another example.

The nonprofits funded by Y Combinator also tend to be young organizations trying to invent novel technological solutions to social problems from scratch, though there are some exceptions, like the ACLU.

But Sam Altman said the tech industry is absolutely engaged in trying to solve problems in the Bay Area. He cited Y Combinator’s pilot basic income program in Oakland, as well as an organization called Rise San Francisco as an example of direct engagement with existing organizations in its own back yard.

Image: Quartz

Rise San Francisco (not San Francisco Rising, which is totally different) was a political action committee that existed from September 2016 until April of this year. Altman sat on the steering committee, along with representatives of several tech companies and conservative real estate and business interests.

The group’s activities consisted of creating a website, writing a few press releases, commissioning a poll, and holding several meetings before it was dissolved, according to SF Bay Area Renter’s Federation founder and former steering committee member Sonja Trauss.

Its two stated goals were “building more diverse types of housing and investing in transportation improvements”. The organization didn’t spend any money itself during the 2016 election, but many of the organizations its members belonged to did — collectively, organizations whose members sat on the Rise SF steering committee (neither Y Combinator nor its employees among them) contributed $554,500 to the campaign for Prop Q, the ban on tent encampments.

Increased sweeps of tent camps have kept the Coalition on Homelessness busy this year, but Friedenbach said they’ve been able to put the $20,000 to good use — aside from upgrading the Street Sheet, they used the money to bring more of their staff from part time to full time, and they’ve leveraged the extra staff time to bring in more volunteers and even more funding.

She said that helped them win some concessions from the city in the last year, like increased housing subsidies to get homeless people off the street and into housing, and funding for lawyers for low-income tenants facing eviction.

She said she understands why people are frustrated with the homelessness problem in San Francisco, and how it seems like it’s not getting any better. But she insisted that the right thing to do is listen to homeless people themselves about what the solutions are.

“The business community isn’t asking the homeless community to solve their software problems,” she said. “They’re getting software experts to solve software problems. So, you know, why the fuck would you think that the business community has the answer to the homeless issue?”

As for Cegłowski, he started an organization called Tech Solidarity immediately after the election in November to connect tech workers to ongoing social justice efforts in tech hub cities around the country. Its first meeting was held in San Francisco, and Friedenbach was invited to speak.

He never mentioned he was the source of the mystery donation. He said he couldn’t think of a way to take credit for the donation that didn’t feel “smarmy or self-serving”, especially since he said his ego was already inflated from causing the donation in the first place.

He was less reserved about purchasing and shutting down one of his company’s biggest competitors last week though — his statement to the media just said “I am the greatest.”