21 for ’21: Sibley Simon building a plan around affordability, homelessness

Sibley Simon
(Kevin Painchaud / Lookout Santa Cruz)

Sibley Simon, president of a nonprofit housing development company, is building 120 units of permanent supportive housing on the Housing Matters campus in Santa Cruz. It’s yet another step in his mission to achieve ‘functional zero’ on homelessness.

Six years ago this week, tech entrepreneur Sibley Simon had a Thanksgiving Day realization: He needed to turn his work as an activist who helps the homeless into a business venture.

He had spent years trying to eliminate chronic homelessness through a grassroots movement called 180/180, which he founded. That campaign aimed to find homes for 180 of the most medically vulnerable, chronically homeless people in Santa Cruz County — and turn their lives around 180 degrees.

By fall 2014, the group had exceeded that goal, housing more than 200 people. A subsequent initiative — 180/2020 — has housed hundreds more.

But Simon concluded on that Thanksgiving in 2014 that it still wasn’t enough. “We’ve done the same things here that some cities across the country have done to reach ‘functional zero,’” a term describing the effective end of homelessness, “but we’re not remotely there,” he recalls.

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If he wanted to change the trajectory of the region’s intersecting homeless and affordable-housing crises, he would need to step into the arena as a key player — a developer.

He had the business background: On his LinkedIn profile, he calls himself “a serial entrepreneur,” having founded or co-founded companies including StreamSage, a natural language processing company acquired by Comcast.

Now, as 2021 approaches, Simon is ready to take big swings.

His company, New Way Homes, received approval from the Santa Cruz planning commission last week to build a five-story building with 120 so called supportive-housing units on Housing Matters’ Coral Street campus. If approved by the full City Council, that project dovetails with Santa Cruz County’s three-year strategic plan for reducing homelessness by 30 percent in three years.

So what’s supportive housing? It not only involves providing shelter, but also expanding “wraparound services,” for the unhoused, including health care and counseling overseen by Housing Matters.

It’s a distinctly 2020-ish endeavor, both in its approach to holistic care for vulnerable people — and because it couldn’t have happened before now, Simon said.

The severity of California’s housing crisis and corresponding changes to state law — including AB 1851, a bill Simon helped write — have forced local governments to become more open to residential development, he said.

“This would have been great to do five years ago, but the local rules didn’t allow it. And they didn’t even try to allow it,” Simon said. “So the state had to step in and force cities to allow things like this. Now we can do it, and now they love it.”

Sibley Simon
(Kevin Painchaud/Lookout Santa Cruz)

Simon hopes to finish the apartment building project by the end of 2022. He’s optimistic that changes to come in the next several years will allow for bigger solutions to the region’s massive housing problems.

“Helping one more person out of homelessness? That is good . . . but it’s not good enough,” he said. “We’ve got to analyze, look at the end goal. And the end goal is a full solution, and a full solution not vaguely 100 years from now.”

Lookout's 21 for '21

EDITOR’S NOTE: We’re profiling 21 individuals who made a difference in pandemic-and-wildfire-ravaged Santa Cruz County in 2020 — and how they’re looking toward recovery in 2021. Have suggestions about others we should pick? Email us at news@lookoutlocal.com

Santa Cruz Salutes: Shoutout someone doing good things for the community


The Santa Cruz community comes together in hard times, which was especially evident in 2020. Do you know of someone who volunteered, donated, or helped the community in some way this year? To give someone a Santa Cruz Salute, fill out the form below with a photo of them and a short description to describe how they are trying to make the community better